(This story was commissioned by a dear Patron of mine, Julia Michelle. For more of my stories or if you want to see me write out your story idea you can check out my Patreon: https://www.patreon.com/Fibaro )
Intro
Ash was a regular though somewhat effeminate looking 19-year-old guy with a not so regular wish as far as guys were concerned. He had always dreamt of being a model, a surf model to be precise. There was just something so powerful about those images from surfer models that had struck him from a young age. The way in which they stepped out of the water their long wild hair neatly folded back by the water, with their board under their arm. It had something magical for him.
What he would never admit to anyone however was that he truly desired to be one of those babes on the beach. He had always admired the tons of supermodels his mother worked with, their beauty, their elegance and just the sheer confidence that radiated from them. Of course he wouldn’t want to be caught dead dressed in a bikini like one of those girls so it was a desire he strictly kept to himself and even he barely dared think of it. It wasn’t even that he truly desired to be a woman, he was happy as a guy, but the feminine grace and outfits just looked so much better.
Having adopted a lot of his mother’s good genes, who once was a model herself and now ran a modelling agency it looked like he could make it. He had spent lots of time in the gym to get some visible muscle showing. Sadly, it was a hard thing for him to achieve, but through hard continued work he managed. His dirty blonde hair was about shoulder length and went well with his bright blue eyes and great tan. Standing at about 5’9” he was pretty much average in length.
With the aim to match those pictures he Idolised Ash often raided his sister Keira’s skin care products. If he wanted to shine in the role of a hunky surfer, he needed a smooth and spotless torso and complexion. As he had found out rather early nair and moisturisers seemed to do that job perfectly that’s why he used it all over his torso and even his chin. Sadly these products that yielded the best results were aimed at women.
His sister would always get mad at him when she found one of her expensive products missing or drastically depleted. Not that he really cared. Him and his sister had never gotten along. She was three years older than him and had always been able to get the better of him when it got physical. Unlike Ash she took a bit more after their father who was out of the picture.
Her hair was raven black yet she had the same bright blue eyes as him and their mother. She was built more athletically, only an inch taller than him, but her shoulders were wider and where he had to stick to his training schedule to maintain his muscle tone, building muscle seemed to come natural for her, she could bulk up without much effort.
Keira was a huge feminist and tried her best to break stereotypical gender norms. Unlike her brother she actually had modelling contracts a plenty. They weren’t the contracts their mother had hoped for though. Their mother had loved it when she first had a girl, someone to follow in her footsteps, but from a very early ages already Keira had started rejecting the dresses and pretty outfits her mother had tried to force on her.
The contracts Keira got were nearly always aimed at her looking though. Something that came natural with her athletic figure and short pixie cut. When shooting she aimed to show girls around the world that girls could be just as tough and even tougher than guys. Something which she liked to carry through in her day to day life.
It was her brothers favourite spot of attack. Ash simply loved pointing out that Keira was just a girl while heavily insinuating girls were weak. Afterwards he would have to rush away since Keira could very well beat him up and wasn’t scared to do so either. She had proven so time and time again. Yet seeing his sister pissed was worth it time and time again.
She on the other hand always loved teasing her brother for being a wimp. Although she knew fully well that he was a hundred percent hetero she loved asking him if he was gay. It was just too easy as well the posters of the models he aspired to be hanging in his room as well as his always completely smooth torso and face were pressure points she loved to exploit. He would always get furious, telling her she didn’t understand. Getting furious and yelling at her was pretty much the best he could do since he knew full well that he couldn’t physically take her on. The times he had tried she had simply overpowered him and made even more fun of him.
Their mother Beatrice had long ago given up on trying to keep the peace in the house. Being a businesswoman suited her a lot more than being a mother did. She spent more time looking for the next big contract than she did worrying about her children, after all they were old enough to care for themselves now. On the rare occasion that she did bother with her children’s quarrels, she nearly always sided with Keira, she might not be the daughter she had always wanted, but she did bring in great contracts and her boyfriend Daniel and his family were one of the main investors in her company.
For a woman in her mid-forties Beatrice didn’t look like she had aged a day. At least not when she was fully dressed. Her body was toned and curvy, her hair honey blonde and she had bright blue eyes and a fairly tan skin. Over the course of the years she had had some minor plastic surgeries, together with her strict workout regime, a healthy diet, and a little help from outfits and makeup to accentuate her best features she could easily pass for someone who had just hit thirty.
Chapter 1
Today was a day like any other Ash had just finished his weekly hair removal and moisturiser ritual making his torso shine like never before. He had stolen a new moisturising cream from his sister and he had to admit it was the best one he had ever used before. He certainly hoped she would be buying it more often as he stood in front of his mirror admiring the results in nothing but his boxer shorts.
“Argh you little shit, you’ve been snooping in my room again haven’t you? Now where the hell is my Essence of the Himalaya wonder cream? I swear you’ve better not touched the damn thing or you’re going to be so sorry. I was paid good money to do an unboxing and review on Instagram. Now where is it?” Keira asked clearly pissed, still dressed in her light blue leggings and tight black sports bra, sweaty from her morning jog.
A nervous sweat instantly broke out across Ash’s face. His sister was more pissed than usual, it would only grow worse as well once she found out that he had opened it and used most of the small pot already. With her in his room already he had no where to escape to either.
“Well where the fuck is it you little faggot? I’m not going to ask again.” She said threatingly raising her arm when she suddenly spotted the pot of cream on his desk, still open and next to the packaging that was ripped to shreds. Instantly she rushed over to it, her anger rising as she saw it was nearly empty.
“What the hell did you do you little shit? Do you have any fucking clue how much money you just lost me and mom? Oh your fucking ass is going to be so fucking sorry for this.” Keira screamed as she charged at him.
“I… I’ll give you money to buy a new pot. Besides why do compagnies even pay you to advertise, it’s not like any amount of moisturiser could ever manage to make you any prettier. You might be just a woman, but hell I bet you know everyone knows I am a more beautiful woman than you are.” Ash screamed, holding his arms in front of him to try and defend himself.
Ash wanted to kick himself as soon as he said it. Seeing Keira’s triumphant smirk told him it was a big mistake. In his zeal to get in a painful zinger and win this argument, he revealed his biggest secret to her and now she knew. How could he had been so stupid.
Much to his horror the hits stayed out and Keira stopped her charge, a triumphant smirk suddenly appearing on her face. “Oh yeah? Well bet accepted, now put your money where your mouth is and fucking prove your claim. Tell you what if you manage to prove your claim, I let you off with just repaying the money I missed out on. If you can’t then I guess I’ll just have to beat you and film you for my Instagram story. I bet the whole world would the story about my faggot brother beaten by a girl as his moisturised torso and face are in full view to promote the product. I can already imagine it. Something along the lines of buy this product and your skin will look so good that no guy will be able to keep his hands off you. Tested and approved by my brother who’s just getting ready for his date with a big hunky man.”
“Nooo! You can’t be serious that was just a figure of speech. Not a real bet! Besides if you just buy a new one the problem is gone.” Ash protested his face going pale at the thought of being exposed like that along with such lies for the whole world to see.
“It isn’t yet on the market you dimwit, I can’t buy a new one. This is meant to be a pre-release advertisement. I do bet they would give me a bonus however if this video I would make went viral which I’m sure it will. Figure of speech or not, a bet is a bet or do you want to fight over it?” Keira asked with a smirk, knowing full well that there was no way in which her brother could beat her.
Seeing an opportunity to make it to the door. Ash dashed out still clad in only his boxer short shouting, “I’m telling mom!” While his sister instantly ran after him, not able to catch up with him before he made it to his mother’s office, barging in without knocking.
“Mom, Keira has become crazy. She…” Ash started off his defence as pissed Keira quickly appeared behind him, but before he could really say all that much his mother silenced him with a quick finger to her lips and a near deadly stare.
“Yes, I know it’s unfortunate, but she really is in no state to appear for a shoot any time soon. Yes I understand, we’re approaching the deadline and I’m trying my best to find a suitable replacement, but models just don’t grow on trees. A fine if I have to break our contract, but…” His mother spoke over the phone when the line was abruptly cut off. “Jack ass!” She shouted in the now dead phone before putting it down.
“Ash you know I don’t want to be disturbed when I’m in my office. You just interrupted a very important call so I better hope you have an extremely good explanation for this.” His mother said annoyed, rubbing her temples. Her mood was already at an all time low. One of her most asked for models had had an accident with her bike this morning. She had fallen flat on her face and skinned one of her cheeks pretty badly. It wasn’t a serious injury, one that would heal eventually, but it would take time for that wound to completely disappear and with such a wound in the face pitching her as a model was out of the question for now.
The firm who had specifically asked for her to be on the packaging of their newest hair products was one they often worked with, and if she wouldn’t be able to find a replacement for the shoot within the week she would be screwed. This was a very competitive business and this firm had many contracts with her agency. They had just threatened to pull them all while also fining her. This disaster could mean she lost a quarter of the yearly income.
Her son stood there lost for words, he knew he had just screwed up big time. He could tell his mom was already in a foul mood, and he doubted she would find his reason for barging in here acceptable. Shit he was in so much trouble.
Eventually he spoke up, hoping for the best as he started explaining the situation. “Keira here threatened to beat me up and expose me for the whole internet. She has really become crazy. You have to stop her.” Ash whimpered.
Keira immediately objected. “He fucking snuck into my room and stole that pot of Essence of the Himalaya wonder cream that I was supposed to unbox and promote on my Instagram. It’s completely destroyed and empty and isn’t yet on the market either so there is no way I can do this contract now. He then bet and these are his exact words that everyone knows he makes a more beautiful woman than I do. I took on his bet and told him to put his money where his mouth is, or that I could just film him for my Instagram story to show of what their product can do on his chest. I bet that would go viral and would earn some extra on that contract.”
She knew contracts where sacred for her mother and since not only she but also her mother could lose money over this she already knew her mother would side with her. She could see on Ash’s scared face that he knew it as well.
At first Beatrice’s blood started boiling. That contract her daughter had been talking about was one with the same firm that she just got off the phone with. They were already threatening to cut all their contracts for not being able to deliver with the model they requested. If she had to tell them there was yet another problem her income would be screwed and the reputation of her agency could get severely damaged. She really couldn’t afford this right now.
Then all of a sudden the full extend of the story hit her and slowly but surely an idea started to form. She had always known her son was somewhat effeminate. Hell he was pretty rather than handsome, one of the main reasons while his so claimed dream of being a surfer model would never work no matter how hard he tried to get in shape. He just didn’t have that handsome manly face to go with the smooth torso, and no where near the muscle mass required either, no matter how much he trained.
With some makeup, as well as good poses and the right angles, she believed that her son could probably convincingly pass as a pretty girl. In fact she was quite sure of it. He also had full well taken care of blonde hair like the model who had fallen on her face. Maybe just maybe she could manage to pitch him for that contract, it would safe her agency from a big loss and maybe she would even be able to make a good profit out of it.
After all in this present time there was a big demand for models of all sort, transgendered, full figured, hell even butch ones like her daughter. All sorts of companies tried to diversify the models they used in their advertisements as much as they possibly could. Having a pretty “trans model” under her agency could give her a big boost in contracts. This could prove to be a perfect opportunity if she played her cards right.
In a matter of seconds Beatrice’s ready to explode look changed to a big smirk. Although it should be a relief that smirk was scarier to Ash than the anger had been. What the hell had made his mother suddenly change like this?
“Well Ash, I think your sister is right. You should put your money where your mouth is if you’re making bets like that. You should pay up by either winning or taking the consequences of losing. We are no family of losers though so I insist you’ll first try to win.” Beatrice said looking into her shocked son’s face while her daughter was smirking broadly in the background.
“You are right on one thing though Keira is crazy to just expect you to prove your claim right on the spot. We women have had years to figure everything being a woman entails out. It would be crazy to think you could just show your claim right away. The least we should do is give you all the tools and help to prove your claim.” Beatrice continued
“We’ll help you with your makeup, your outfit, then do a little shoot to compile a modelling portfolio and put it next to that of your sister. We can then ask some of our models and photographers who work for us their opinion on who they think makes the more beautiful woman. Of course won’t give away your identity so their opinion won’t be biased. I think that’s the fairest method of approach. Of course since you made the bet with your sister we should ask her if she agrees to these terms, or if she really believes you should just prove it now or appear on her Instagram.” Beatrice finished.
Ash was shocked, sure being a gorgeous model had always been a dream of his, but he was too ashamed to tell anyone. He sure as hell didn’t want his mother and especially his sister to see him like that. He simply wouldn’t hear the end of it. Let alone letting others see him like that or worse take pictures. His mother hadn’t even asked if he agreed to those terms. In the bigger picture this sure would be preferable than being beaten up by his sister and called a faggot for the whole internet to see. It was something that would haunt him for the rest of his days. Everyone would only know him as that faggot who got beat by his sister. Compared to that a semi anonymous portfolio was definitely the lesser of two evils.
Keira’s smirk had only grown during her mother’s explanation. Giving her brother a make over would be so much more fun and satisfying than just humiliating him on Instagram. Hell if she could get her hands on that portfolio as well then she had him right where she wanted him. There was no way he would ever be a nuisance to her anymore if she could threaten to spread that thing.
In fact she could use that portfolio to push her own agenda as well. One of the photographers had been bugging her for ages to do a ‘special shoot’ with him. Everyone knew he was a big perv though and there was no way she would ever agree to his offer. An offer he made to pretty much every model in the agency except for the male ones. He was such a perv that most models were reluctant when they knew he would be shooting, sadly he was a genius with his camera and so her mother wouldn’t even think of firing him. Maybe if she could make Ash appealing enough she might be able to switch his focus to him, have Ash agree to his ‘special shoot’ so maybe he would leave her and the other models alone.
If she managed to make her brother really pretty she might even manage to get her asshole of a boyfriend Bruce to develop an interest in him. He was an asshole from a rich family who her mother had hooked her up with. His family was one of the big investors in her agency so she couldn’t just break up with him or her mother would be angry out of her mind.
Sadly she and Bruce had very different ideas of what a woman should be like. While she was all for the butch look, female empowerment and independence, he thought a woman should just look pretty and be obedient. His mindset was still stuck in the 50’s and the only reason he got away with it was because his family was rich. Oh how she wished she could beat him up. Her mother would probably kill her if she did which was the only thing stopping her.
Up until now she had managed to keep true to her ideals and looks for the most part. It wasn’t something she was willing to change either, but Bruce was getting more and more impatient and demanding. She was pretty certain she soon would have a choice to either give in or breakup, and a breakup was something her mother would never allow. Unless of course she could make Bruce fall for a prettied-up Ash. She was certain that her mother didn’t care about who exactly was with Bruce, just that his family stayed tied to hers for their investments.
Keira was extra motivated to make Bruce fall for her brother. Not only would she be rid of the asshole, she would also finally be able to bring her secret relationship with Ellen, another one of her mom’s models out in the open. With that in mind she replied. “Oh you’re absolutely right mom, It was crazy of me to be expecting him to just prove it. We have to give him all the chances we possibly can to make him the prettiest possible girl before we pass judgement.” Keira eagerly said playing right into her mother’s cards.
“Of course we do need professional help to give Ash the best possible chance. So Keira while I fix a photographer, a makeup artist, a stylist and a hair dresser why don’t you teach your brother the basics? The shoot probably won’t be for today anymore, but that way Ash can get into the role a little already. “Beatrice said with a smile before waving her kids away as she started dialling on the phone, making clear no discussion would be had about it. Keira was all smiles and a stunned Ash was too afraid to interrupt his mother again.
Looking forward to having some fun at her brothers expense as revenge Keira grabbed Ash’s hand and started leading him down the hall again. “Oh mom is so pissed, she sounded like she was about to lose a big contract and then you barge in screaming and basically admitting you screwed another one of her contracts. I don’t know what mom will do if you screw up again, but I’m sure it won’t be pretty.” Keira said with a huge smile, rubbing the situation in further to ensure Ash would be very compliant when she got to work.
On the short walk to their rooms Keira was thinking about what kind of style she wanted for her brother. One thing was for sure, it should be a rather extreme style as she really wanted to get the most out of embarrassing her brother now that she had the chance and her mothers blessing. There was no way Ash would normally agree to let her do anything to him, but being able to threaten with telling their mother would prove a powerful tool right now.
Keira choose to march her brother into her own room simply because she had a vanity table an he didn’t. If she wanted to teach him all the tips and tricks of using makeup then a good mirror would simply be a necessity. “Alright little brother of mine, let’s start with your very first makeup lesson shall we?” Keira asked as she forced her brother to sit down in front of the vanity table, still clad in nothing but his boxers.
“First and foremost, we need to get you makeup ready. The first step would be to use a good hydrating facial cream, but since you already used one of mine, even on your fucking torso I guess we can skip that step which leaves us only with those bushy brows of yours.” Keira said with a broad smile as she picked up a pair of tweezers.
“Keira, please don’t, just be reasonable for a moment they won’t just grow back after you gave this stupid bet of sorts which you know was just a joke it’s best try. God knows how long it would take until that damage is gone.” Ash spoke nervously and genuinely scared of his sister.
“Joke or not, you shouldn’t have said that if you didn’t mean it, besides as I recall it, it didn’t even sound like a joke at all. I know those brows will take time to regrow, but just think about it, we can’t give this our best shot if we leave your brows as they are now can we? If you really think I’m being unreasonable we could go back to mom and interrupt her phone call again. I bet she will be thrilled to confirm that we really should take care of those brows of yours.” Keira offered with a smile knowing full well she had the upper hand.
Ash realised full well if they went to interrupt their mother once more he would be into a world of trouble so he nervously stammered.” N…no, that won’t be necessary.” He was more scared of his mother than he was of how visible this change Keira might make would be. It wasn’t even that he was against getting his eyebrows plucked. He was just scared that everyone who would see them would know of his deepest most secret desire.
“Good, then sit still as this is only going to hurt a bit.” Keira smiles as she moved Ash’s head back none too gentle, a bit surprised as she gave his eyebrows a closer look to find in a pretty neat state already. There were no stray hairs to be seen, yet they were rather full and thick. Too thick for the look she wanted her brother to have so she started plucking away. Her brother was a bit of a freak when it came to immaculately maintaining his appearance so the neat brows weren’t that out of the ordinary.
By the time Keira was ready allowing him to look down Ash was horrified. There was nearly nothing left of his eyebrows, nothing but two extremely thin high arches. Although he had secretly like the thought of having a bit more shapely eyebrows he really didn’t like what his sister had done with them. Eyebrows this thin had been out of fashion for ages, they were simply horrible.
“I’m so glad you like them. Ash, they are so you, now watch carefully as I apply your foundation, cause once I’m done with your makeup you are going to redo it yourself.” Keira said with a big smirk enjoying the shocked look on her brothers face. Revenge was so sweet.
Ash’s horror only grew as he witnessed how his sister completely ruined his face with the tasteless tarty sissy makeup she applied while telling him how he had to replicate the look. The foundation she used was way to pale for his skin making it look nearly porcelain white. It was followed by colouring his newly plucked arches in way too dark, the pink lip liner she used deviated way too far from his actual lips looking fake as hell instead of just enhancing the lips. The bright pink colour lipstick and overdose of gloss only made it worse. For his eyes she chose exaggeratedly large wings paired with mascara and a solid colour of pink eye shadow over his entire eyelid before finishing the look with two deep pink circles on his cheeks. Ash ended up looking like a weird combination between a hooker and a porcelain doll and he simply hated it, something Keira delighted in.
“Tada, you’re all ready. Just look at you such a pretty doll, Maybe you are right and you do make a prettier girl than me. What do you think should we take a selfie and ask my followers?” Keira taunted giving Ash the scare of his life there was no way he ever wanted to be seen by anyone like this.
“Maybe we better wait though cause I don’t want to get banned for indecency because my pretty little brother is showing some nipple. I bet you look so convincingly that they would think you are a girl and we all know girl’s nipples aren’t allowed. Just wait here while I find you a fitting outfit to go with your new look. While I’m busy with that I want you to try and replicate this look on your own, after all a girl needs to know how to do her makeup. There are some wipes over there, just follow what I thought you and you should be fine.” Keira taunted as she was already looking forward to the final result. Surely it would be badly applied on top of being tarty making it look even worse. She couldn’t wait to see that.
As fast as he could Ash grabbed the wipes and started carefully removing every trace of the makeup his sister had slathered on. He just couldn’t stand the tarty face starting back at him and he couldn’t be rid of it fast enough. Expertly he wiped his face clean in less than a minute. A skill he had picked up when he sneakily tried to put on makeup before, but had to get rid of it quickly not to get caught.
With that horrible makeup job finally gone Ash started reapplying the make up as he had been ordered to by his sister. He knew he couldn’t deviate from her look too much so he had to use the same products in order not to raise too much suspicion, but there was no way he was going to allow his face to look that tarty again.
The foundation still was way too pale for his skin, but he kind of fixed it by applying a way lighter coat, making his own skin shine through way more giving him a darker toned end result. The brows were pretty much a lost cause having been plucked way too thin, yet with the help of the eyebrow pencil his sister had used to turn them really dark he managed to outline new fuller brows, going easier on the colour to make them appear more naturally again.
His sister who turned around with a smirk from her closet, looking for the perfect outfit, but not wanting to miss the chance to see her brother struggle and fumble with his makeup ended up being rather surprised. Ash in fact looked rather calm and collected applying the makeup not perfectly, but certainly with a certain skill. From what she could see now he was also doing a better job or at least a less tarty job of his makeup than she had given him.
This made her think back to her earlier confusion about his neat brows, and the confident way in which he had said he would make a prettier girl than she did. The previous two things she had been able to explain for herself, but for this makeup there really was no explanation. Her earlier suspicion’s returning in full force Keira decided to sneak off to her brother’s room instead to look for some confirmation for what she suspected.
Ash was so focused on his makeup job that he didn’t even notice Keira leaving the room. Instead he redid his lips, simply outlining his lips with the pink lip pencil, giving the illusion of being slightly more voluminous before applying the same bright pink lipstick but only using a hint of gloss giving his lips a healthy shine. For his eyeliner he resorted to simple top and bottom lines with tiny wing as an accent before applying the mascara. For his eyeshadow Ash resorted for a deep intense colour close to the eye which grew gradually lighter the further from the eye it went making it look far classier. Finally for the blush Ash carefully applied a little dusting highlighting his cheekbones more than anything.
Leaning Back Ash was rather pleased with himself. While the colour scheme was not something he would have personally chosen he had managed to turn the look his sister had insisted on into something somewhat more classy and definitely more natural looking.
What Ash didn’t know however that his sister had gone up to his room and had actually found the outfit he had carefully hidden away. It consisted of a simple dress, a very sexy lingerie set that Keira had once worn for a photoshoot she had wanted to refuse, but her boyfriend had insisted she’d do because it looked ‘hot’ and a pair of strappy sandals.
Her suspicion that Ash might actually secretly like this was confirmed, but seeing how strongly her brother kept denying it she could definitely tell that he didn’t want it found out at all. This was even better than she had initially thought as it meant she could now use that secret as leverage over her brother to push her own double agenda she had with the photographer and her boyfriend.
With proof of his secret in hand Keira walked back to her room with a big smile. Ash certainly had a lot of explaining to do, and he had a good reason to stay in her good graces as his secret staying a secret now entirely depended on her silence.
Chapter 13
Keira was feeling on top of the world and it felt like nothing could spoil her mood ever again. She had full control over both her brother and her boyfriend, the two biggest annoyances in her life. Now they provided her with more of a thrill than an annoyance though. There was just something so powerful about keeping them both under her thumb. Her brother might have wowed everyone and gained their mother’s favour, he might actually have been happy with how passable of a girl he made, but now she had him back under her thumb. As for Bruce now it was her time to fuck around, and she didn’t hesitate to place a personal ad looking for a girl who was into cucking her boyfriend.
In the meantime she didn’t really care about Ashley, she stayed out of her way afraid to make a wrong move as far as she was aware and she was perfectly happy with that. The only thing Keira wasn’t aware of was how Ashley was undermining her control at this very moment. The day of her date with Bruce and the following blackmail she hadn’t left her room at all. Only the day there after, after making sure her mother was already downstairs, she finally emerged form her room.
Ashley had treated herself to a nice long bath this morning after sleeping in lavish satin pyjamas for the second night in a row. She had put on a nice flared burgundy coloured skirt. For a top she had chosen a nice cream form fitting turtleneck. It showed the curve of her breast forms off perfectly while simultaneously hiding the silicone so no seam would show as she was no where near as good as blending the makeup there as Jessy was. On her legs she pulled a pair of sheer black pantyhose and finished the outfit off with a pair of brown leather ankle boots with a three inch tall chunky heels. In order to add some extra style and cuteness to her lovely outfit, she had applied some light natural looking makeup, and tied her hair off in a high ponytail with a burgundy coloured satin bow.
She was a bit nervous to encounter Keira as she stepped into the hallway, getting on a hurry to move downstairs only to relax when she met with her mother down in the kitchen. She was staring right at her over her morning cup of coffee. It felt a little awkward for Ashley as she walked over to her mother’s side and greeted her with a peck on the cheek before turning to the coffee machine for a coffee of her own. “Uhm hi mom, good morning.”
“Good morning to you too sweetie. I’m sorry for staring, I just couldn’t get over what a gorgeous girl you make. I’m afraid it’ll take some getting used to. Great choice of outfit as well, I love it.” Beatrice mused in awe of what a pretty passable girl her new daughter made, it was weird, especially since she hadn’t seen it coming at all, just a few days back she had still seen Ash as all boy. It was lovely to have one of her children who inherited her style though.
“That’s okay mom, I guess I can’t really expect you to act as if I’ve always been your daughter, it has been a rather radical change after all. I’ll admit it felt a bit strange for me too, to come down wearing a skirt, but it just feels so right you know? In any case what I’m trying to say is that I am truly grateful that you make the effort to accept me for who I really am. It means the world to me. Coming out to you has made me realise just how much I have been repressing and it made me realise that I can’t go back to being Ash. I kind of wanted to wait to come out to my friends, but I can’t put on that façade again so it can’t really wait I guess. I was actually thinking of meeting up with Jessy today to have a talk about how I could come out to them. She has some experience with people like me after all, maybe she has some tips to make it easier?” Ashley said as she joined her mother at the table.
“I think that’s an amazing idea sweetie and if there is anything at all I can do for you to help you out I will be more than glad to. You just let me know okay? By the way, would you like to know how my contract negotiations for you went yesterday?” Beatrice asked with a sweet smile, hiding her slight nervousness. She was afraid that some people might react poorly to Ashley’s coming out, that they would hurt her. Things were moving very fast and rapidly so. If it had came as a shock to her, she imagined it might be the same to her friends and girlfriend. She tried hard not to let her nerves show however, if Ashley would be hurt then she would be here to take care of her, the last thing she needed were extra worries. Besides going to Jessy sounded like a superb idea, that woman had been a great help already and had done wonders for Ashley.
“Oh yeah sure, I would love to mom, sorry that I haven’t asked, but I’m dying to know. It’s just that I’ve had a ton on my mind these past few days so that bit kind of slipped my mind.” Ashley said somewhat nervously. She could hardly tell her mother what had happened yesterday as it would probably break her heart, but it had caused her to have a lot on her mind. As curious as she was about the results of the negotiation, she was also kind of scared of the outcome, fearing that she would be rejected because she was no real girl, something that Keira had tried to make awfully clear, yet her mother’s cheerful mood kind of gave her hope.
“That’s completely understandable Ashley, don’t worry about it at all. It’s just that I have some exciting news and I bet you would love to hear it. The company would love to work with you. They adored your portfolio and they would love working with you to become the face of the new hair product line they want to roll out. They thought you would be an even better fit than the model originally supposed to take the job. Hell they even threw in a bonus just for you and if the shoot goes well, they would love you to model for their skin care lines as well.” Beatrice said enthusiastically, loving the amazed and excited look on her new daughters face.
“It should take a month or two for the first products with your face to be published. So if you would rather wait with your coming out you definitely have time to think things over. That being said just do what you think is best. I love you sweetie and that won’t ever change.” Beatrice spoke, grabbing a firm hold of Ashley’s hand in support.
“Thanks mom, that means the world to me, and you can’t believe just how happy I am that a company wants to sign me on as a genuine model. I can still hardly believe this is real, I mean wow, I really don’t know what to say.” Ashley said mesmerised, touched by her mother’s support and the unbelievable outcome of her mother’s negotiations. She really couldn’t believe that a company actually thought she made a pretty enough girl to become the face of a new line of products they were about to roll out. It was a huge compliment, one that meant so much more than her mother telling her how cute she looked. After all her mom might just say it to make her feel good, companies didn’t do that. It gave her such a confidence boost which made her feel a little more at ease with her plans to come out. This was exactly what she needed right now.
“You don’t need to say anything sweetie just remember this when you are struggling a little. You are a gorgeous amazing girl I am lucky to be able to call my daughter. Never forget that sweetie, I’m proud of you.” Beatrice spoke as she got up and gave Ashley a tight hug. It was a bit strange to feel the bra straps, and smell the flowery shampoo in the hair of who she had considered her son just a few days ago. None of that mattered though, Ashley was her daughter now and that was great just the way it was.
“I really appreciate it mom, thank you so much for everything. I never thought this whole bet with Keira would get so out of hand, but I’m glad it did. It was the push I needed to finally be open about who I really am, and I’m infinitely grateful for your amazing support mom, I mean it. Oh I bet that is Jessy.” Ashley said, interrupting her heart fell speech when a text message rolled in.
Beatrice stepped back with a big smile. It warmed her heart to hear Ashley say that. It made her feel so much better knowing that Ashley didn’t really blame her for not having seen her for who she really was all along. Seeing the smile creep onto her new daughters face as she read that message made her feel even better. For as much as she feared for Ashley and how her friends would deal with her coming out. She had a feeling that everything would be alright. This Jessy sure seemed to be able to put a smile on her daughters face so in the worst case she had a new friend if things wouldn’t work out with her old friends.
“I’ve got to go mom, Jessy has some time on her hands for a quick brunch now, but then she has to go do some work. I hope you don’t mind me rushing out, I appreciated our talk, I really did. I just want to see to see this whole coming out situation resolved as soon as possible.” Ashley explained apologetically not wanting to offend her mother who had done so much for her these past couple of days.
“I don’t mind one bit sweetie, I hope she’ll be able to give you some sound advice you feel happy with. Oh and while you’re at it don’t forget to have fun. I know I always enjoy my brunches with my friends.” Beatrice smiled, giving Ashely a tight hug before waving her out at the door. Things sure did look like they were going to be alright going forward, she only hoped that Keira would come around as it did hurt how her other daughter couldn’t seem to be happy for Ashley. She loved both her children after all.
Chapter 14
The drive over to the address Jessy had given her was a relatively quiet one where Ashley was more happy than she was worried like before when she was about to head out in public. Having passed on the shopping trip with her mother, the date with Bruce and especially now that she had actually gotten that modelling contract which she could still hardly believe she had gotten, gave her such a confidence boost. If all those things proved one thing, it was that she didn’t need to be afraid to be who she was among strangers.
Nevertheless she was pretty happy to arrive at a rather quiet cosy place outside the city, not because it was more private and had less people, but because it showed that Jessy cared greatly about her comfort, not knowing the progress she had made yet. She was already excited to tell her friend all about what had happened on that shopping trip with her mom, about the modelling contract and about the good things that had come out of that date with Bruce. She just knew Jessy would be happy for her.
Making her way into the cosy building Ashley took a few moments to spot Jessy in one of the more private parts of the establishment. With a big smile she instantly headed over to her, only for her smile to get even bigger when Jessy looked right at her and still took a few seconds to recognise her at which point a look of sheer amazement crossed her face. “Oh my god, Ashley is that you? You look spectacular.” She gushed, instantly getting up to embrace Ashley in a tight hug as she arrived at the side of the table. She knew how good Ashley could look after she had made her up for the shoot, but given how shy she had been only a few days ago, Jessy didn’t expect to see such a gorgeous and even confident girl back. She had expected Ashley to have taken out the extensions, removed her acrylic nails, left out the breast forms and to have worn her old male clothes. She had been expecting to meet Ashley looking more like Ash.
The long and tight embrace ended when Jessy took a step back only to give Ashley a thorough once over, admiring her look. “Damn girl, do you happen to have some style tips, cause I could definitely learn a thing or two from you, your outfit and makeup are simply lovely. You can’t believe how happy I am to see you as the real you with confidence and pride at that. Then again, I imagine you should feel proud when you look in the mirror.” Jessy gushed, further boosting Ashley’s confidence. She was definitely underdress compared to her friend wearing a simple pair of pale skinny jeans, a white tank top and a black leather jacket.
“I’m very happy to see you as well Jessy. As for that confidence you have yourself to be proud of for the most part. My mom has been very supportive and has taken me out shopping, but without you bringing out Ashley and giving me the confidence to be myself, I would have never dared go with her. A lot has happened these past few day. Like you wouldn’t believe it. I think it would be best if we sat down cause I have so much I want to tell you.” Ashley said as she took a seat with Jessy eagerly doing the same thing, all to happy to hear about this true metamorphosis Ashley had gone through since she had last seen her.
After their ordered some drinks and food Ashley went on and on about the amazing shopping trip with her mother, sharing a little about Keira’s blackmail that had led to a scary, yet somehow wonderful date with Bruce. A date that had definitely sparked something between her and Bruce as she talked about their plan only to conclude everything on a wonderful note with the contract her mother had just told her about. Throughout Ashley’s story Jessy had felt everything from warm and fuzzy to blood boiling rage at Keira, she couldn’t believe that bitch of a sister still hadn’t stopped tormenting Ashley, especially when hearing how extremely far she had taken it. At least it was a relief to hear how Ashley was taking it relatively well considering the damning circumstances.
“So I guess what I’m trying to ask is if you could give me any tips as to how to come out of the closet towards my friends. Also if you still want to help me with that I would greatly appreciate it if you could accompany me to a specialist on the front of transitioning. I’ve stopped using those unregistered drugs like you insisted, but I’m certain I want to embrace who I really am.” Ashley concluded her story, kind of surprised about how emotional it left her. Recounting it all to someone she truly trusted really made her realise just how much she had been through in such a short time.
“First of all let me say how truly sorry I am that you have such a shitty sister who has put you through such horrid things. I would love to give her a piece of my mind, but I fear you are right about the trouble she might cause. No one should be forced to come out, but I’m afraid you are right that time is ticking if you want to come out on your own terms despite how much I despise that. Secondly I can’t tell you enough how much I respect this great confidence and drive you are showing despite all that has happened.” Jessy spoke, affectionately grabbing onto Ashley’s hand across the table.
“But those weren’t your questions. My answer is yes Ashley, I admire you greatly and I’ll do whatever I can to help you. As far as coming out is concerned I suggest you do it slowly, give them a chance to ease into a it a little. You make a gorgeous girl, but I would suggest wearing a pair of feminine jeans and a t-shirt when taking that step. Maybe don’t wear your breast forms either. I suggest you go for a slightly feminine look leaning more to androgynous. It will be easier for them to grasp and accept that way rather than blowing them away with what a stunning girl you make. I know it might feel wrong, and I do advise you to feel what you think will be best, after all you are the one who knows your friends best. Toning down your look a little will make it an easier pill for them to swallow though.” Jessy advised.
“As far as the specialist is concerned I’ll contact her and let you know when she’ll be available so we can put our agenda’s together and make an appointment. I’ll call in a favour to get it done as fast as I can, so don’t worry about that, I’ll contact you when I now more. In any case, tell me about Bruce, is he cute?” Jessy asked cheerfully trying to lighten the mood with some regular girl talk, to take away some of Ashley’s obvious stress.
Despite the fact that there were some bad memories connected to her date with Bruce thanks to how Keira had forced it upon her, Jessy’s tactic worked wonders. Ashley thought Bruce was quite hot and as it turned out he was quite nice contrary to what Keira’s bitching made believe. She talked on and on about Bruce with Jessy asking the occasional question to keep the talking going seeing how excited Ashley was about the subject. It was very nice to hear Ashley so passionate and happy, besides, Jessy was also happy to give her some genuine tips about dating guys, tips specific to Ashley’s situation rather than the horrid advise Keira had given her.
By the time they finished with their brunch both Jessy and Ashley were surprised to see how much time had flown by. “Oh damn, I’m very sorry about this Ashley, but I have to get a rush on as I have an appointment to make. Looks like the time really flies when you are having fun. We should definitely do this more often. In any case best off luck and I’ll catch up on you sometime soon okay? Remember Ashley, you can always call me if you need me and if you ever doubt yourself remember what an amazing, strong young woman you are.” Jessy rattled giving him a quick hug and a peck on the cheek before nearly jogging out.
The ending was a little abrupt for Ashley’s liking, but then again that was just because they had been having too much fun so she didn’t mind at all. She had known from the start that they only had limited time, quite a bit of it, but so it seemed still too little. In any case Jessy had once again come through splendidly for her, she was such a valuable friend and she didn’t know if she could ever have been Ashley, or at least not so soon if it wasn’t for her. Once again she had taught her so much and boosted her confidence beyond believe. So it was with a bright smile she left the brunch place. A smile shared with Jessy who was more than happy that she had been able to help Ashley out. She was still mad that Keira would do such a thing, but she was confident Ashley would get through this.
From the cosy brunch place Ashley quickly headed back to the mall. All her excitement to finally be herself on her shopping trip with her mother had left her neglecting to buy anything that could be remotely androgynous, but Jessy was right, it was best not to shock her friends and girlfriend at full force so something more androgynous was exactly what she needed, something girly for sure, but less extremely so than what she was currently wearing. She already missed it just thinking about it. Pantyhose and a cute skirt just made her legs look so fantastic. Seeing how she felt about her search Ashley was once more convinced that she was really made to be a girl.
While she was a bit nervous to head out in the mall all on her own she forced herself to take the leap and in the end she was happy she did as roaming through the halls of the mall alone only fuelled her self-confidence. Jessy and her mom could reassure her that she looked perfectly passable and gorgeous all they wanted, but that just wasn’t the same. Ashley knew they would say that no matter what. Seeing the looks complete strangers gave her however did help reassure her a lot. No one looked at her like she didn’t belong. Some girls were subtlety checking out her outfit while nearly all the guys she passed checked her out in a not so subtle manner. The stares some older men fixed her with were a bit unsettling at moments, but she just tried to ignore those with her head held high. It was something that sadly came with the territory and while she would have rather missed that part she guessed there was a silverling there that she was worth looking at.
Unlike last time Ashley shopped more targeted, going straight to one of the lower end stores rather than doing every single one of the stores. She figured that if she had to wear pants and a t-shirt it might as well be a cheap set as she didn’t plan on wearing them for than a few times for introductions sake. Even so she had a way harder time figuring out what outfit to actually buy. Unlike with her mom, she wasn’t looking for her hearts desire, the cutest outfits she loved most. She had to like it to some degree for sure, but this time appearance sake towards her friends and girlfriend was more important than her own style was.
The last thing Ashley wanted was to go back to looking like a guy making it exceedingly hard for her to settle on an outfit. An outfit that looked both cute enough to feel comfortable in, yet plain and unisex enough not to create too big a shock among her friends and girlfriend. In the end she settled on a pair of light denim skin tight jeans that fit like a glove, accentuating her nice bottom and long legs, stopping an inch or two above her ankles. They felt like a sturdy pair of leggings and none of her friends ever wore pants like this where her girlfriend sometimes did. They were plain without any decorations, only the style setting them apart as effeminate. The t-shirt she settled on to go with it was a plain white one with a tiny logo on her left breast. The waist of the t-shirt was subtly nipped in, it had a v-neck and the sleeves were on the short side. It did once again convey a more feminine style without being too obvious.
To try it on Ashley had taken off her bra and breast forms leaving her completely flat chested. She kind of missed having breasts already, but she needed to see how it would fit without. If she thought away the long painted nails and the more elaborate makeup she guessed she could pass as a plain yet cute looking flat chested girl. She wasn’t all that confident in her own ability to judge whether or not this outfit was good enough though. So instead of simply buying it she snapped a quick picture in the changing room’s mirror and sent it straight to her mother and to Jessy. “I need a second opinion, do you think this is plain enough to meet my friends in? Isn’t it too much? Or maybe a little too plain?” She asked.
As strange as it was, seeing Ashley in her jeans and t-shirt combo, did put Beatrice’s mind a little at ease. She was exceedingly happy to have a daughter as smitten by fashion and modelling as she was, and she wanted nothing more than for Ashley to be happy, yet the thought of how others might react to her coming out was a little unsettling. She didn’t want Ashley to hurt after having to hide the real her for so long and she sincerely believed that this more modest outfit would be a good way to take it a little easier. “You look wonderful Ashley, I think it’s a perfect outfit choice and I am more than happy to give advice whenever you might need some. X Mom” she replied.
Just like her mother Jessy was also sold on the look. “It looks perfect Ashley, I love it! While it’s a shame to see such great legs as yours in pants I think you still make the outfit look amazing. You can pull just about anything off can’t you? Then again, that’s no surprise with someone as cute as you. Go for it Ashley, you got this, I believe in you, and like I said, feel free to call me whenever!” Jessy replied enthusiastically, both positive advices giving Ashley the confidence she needed to settle for this outfit.
Feeling a little more confident and comfortable with her choice Ashley quickly changed back into her skirt which still felt many times better than the pants no matter what. Having her chest back was also nothing but a joy as she quickly collected the jeans and t-shirt only to head for the counter, happy to get this settled as well. Although deep down she knew this was the easy part. Actually breaking it to everyone she knew would be the hard part.
Having successfully shopped for something she didn’t necessarily like, at least not as much as all her other purchases, but nevertheless something she sorely needed, Ashley decided to treat herself to a smoothie at one of the hip bars in the middle of the mall. She sat out in plain view, not even attempting to hide herself from anyone, she didn’t feel like she needed to do that anymore and she really wanted to conquer what inhibitions she still had left about this new her, the her she was more and more certain she wanted to be on a permanent basis.
There was only one real obstacle left for that to happen, and that was telling her friends and girlfriend. She had been avoiding them these past few days ever since that shoot was forced upon her by Keira, the shoot that had in the end proven to be the catalyst she needed to finally discover the real her. She couldn’t continue to avoid her friends for very long and she didn’t want to go back to being Ash so she would have to show them Ashley in short notice. As it turned out she wouldn’t need the old male clothes she had saved after all as she was very determined to come out, to save herself and Bruce who all in all was a pretty great guy from Keira’s clutches.
Unbeknownst to her sister she had once again given her the courage and the strength she needed to force through another big leap in coming out. All in all despite the plots Ashley was pretty much feeling as if she should thank Keira for all she had done, even if only to see the look on her face when she broke it to her that she was the one who had allowed her to find true happiness in life all while trying to get back at her. It was bound to be precious, but that had to wait a couple of days until she and Bruce were safe.
Right now she just basked in the moment of peace she had, enjoying her freedom as the true her while she got nothing but confirmation from those passing by, checking her out in subtle and less subtle ways, further fuelling her confidence as Ashley. It felt down right amazing just to be able to go to a nice bar as a girl with no one judging her like she had always feared they would. It was amazing to be accepted even by complete strangers.
While she enjoyed the reaffirming attention she was getting Ashley turned to her phone and started texting her friends to apologise for not being available for a couple of days and asking to meet up tomorrow. She only had a small circle of really close friends she wanted to announce it to in person as soon as possible. For the others she cared less if they found out through the talk that would surely spread, or when they happened to hang out at some point after she came out as Ashley. Nevertheless arranging everything for tomorrow was one hell of a chore as she wanted to talk to all her friends and her girlfriend within the same day to prevent any of them from hearing about it from someone else. Her heart was nearly beating out of her chest and her nerves were raging inside as the plans started to form. This was all becoming very real, and she couldn’t help but feel scared for their reactions, nevertheless she continued planning.
( If you liked this story and would like to read way more along with a ton of other stories then please check out my page on SubscribeStar: https://subscribestar.adult/fibaro I have ran into trouble with Patreon, but since SubscribeStar doesn’t accept PayPall you can still follow me there, just make sure you connect your discord account to your Patreon account if you do so you don’t miss out on my content. https://www.patreon.com/Fibaro )
Chapter 2
Standing back in the doorway of her own room Keira was surprised to see the wonderful job Ash had done with his makeup. It looked nearly as good as her own best effort despite the colours she had given him. She smiled watching how Ash applied the last touches to his makeup look before coughing loudly just when he was putting the brush down.
Ash who had been so absorbed in applying the makeup as good as he could shook out of his concentration and looked over to his sister in the doorway. His facial expression instantly turned to one of shock as he recognised the outfit Keira was holding perfectly. It was the very same outfit he kept hidden away in his room.
With Ash looking at her it was her turn to be surprised. If you only looked at the head he actually looked shockingly girly, he had never looked the most manly with his clean shaven babyface. The makeup paired with his longish hair really had something cute though. He looked almost like their mother did, although in a way younger, way less curvy version. The boxers and his slightly visible abs kind of ruined the cute girly look, but that would instantly be solved by the outfit Keira had with her.
“My my Ash, don’t you look pretty? If I didn’t know any better I would believe I had a sister. Maybe there is something to you making a prettier girl than me after all. I mean especially with the way you so skilfully applied your makeup and with this cute outfit I found in your closet. Guess I was right and you have always been a big sissy after all. I wonder what mom would think, or your friends if I showed them this.” Keira smiled playing on Ash’s insecurities. From his reaction she could see that the fear of exposure was indeed huge. It told her she had him right where she wanted him.
“Please Keira, don’t I beg you. My life would be over, please don’t tell anyone about this I beg you.” Ash exclaimed in panic. He always felt happier when dressed as a girl, it was one of the reasons he had taken the risk of keeping an outfit stashed away in his closet. Yet the thought of how people he knew would react if they found out about this side of him terrified him.
“Well I don’t know Ash, this is actually a pretty huge deal. Don’t you think people have a right to know? I bet they would be so very shocked, god I wouldn’t dare face anyone if I had such a secret.” Keira said slowly, deliberately fuelling his fear so Ash would be easier to control.
“Although I guess I can help out my little brother, or should I say sister? I’ll keep your secret, but in exchange I’ll expect you to be a very good b… girl for me. One misstep and I won’t hesitate to expose your little secret to everyone. For starters you can put on your pretty outfit for me, everything including those racy lace panties.” Keira said with a smirk as she handed the clothes to Ash.
Still shaking that his sister had found out his secret Ash took the clothes and nervously put them on. He had put on this very outfit countless of times but doing it now to be seen it felt so very wrong and bad in a way. It was his secret guilty pleasure, no one was supposed to see him like this it made the oh so familiar outfit feel almost alien to him.
At least his sister did give him some privacy to get changed, turning her back towards him. Just in case she would turn back around Ash quickly switched his boxer shorts for the white lace thong that came with the outfit. It always made him feel sexy, but now he felt more exposed than anything else. The panties were quickly followed by the matching white lace garter belt, the sheer white stockings with white lace tops which Ash was able to attach to the garters without much effort at all. Even the push up bra that came with the outfit went on without effort.
Once Keira felt somewhat certain that her brother would at least be partially dressed already she turned around, unable to wait any longer to see what he would look like. The slight hint of abs Ash had were still a bit of a distraction from the overall girliness, but the sexy lingerie did form a great distraction from them making Ash look more like a cute girl than a guy.
Keira’s grin only grew when Ash put on the light pink summer dress with a skater skirt reaching till right above his knees. His abs covered and the sturdiness of the cups of the push up bra, tenting the dress a little at his chest really completed the look, covering up the last giveaway’s rather decently. The white strappy high heeled sandals just finished the look.
“My my, just look at you Ash, or wait. Ash doesn’t sound right for a girl this cute. Ashley, yeah let’s settle on that. Just look at how cute you are Ashley now why don’t you give me a twirl so I can have a better look?” Keira asked with a smile watching as Ash nervously preformed her command.
“Awe, just like a prima ballerina. Now let’s go and see mom. I bet she’ll love to see her new daughter.” Keira said with a big grin as she walked over to Ash and put a hand on his shoulder just in case he would try to run.
“Nooo! Keira, mom can’t see me like this. You promised that you would keep my secret if I did as you said. Mom can’t see my like this.” Ash instantly blurted out in panic as she looked back at his smirking sister.
“Of course mom can see you like this Ashley. That’s the whole point, especially since you made a point out of involving her in that bet you made. Now the choice is yours, either I’ll go show you to mom like this showing her what a good job I did on your makeup and what a cute outfit I selected for you.” Keira said sternly leaving a long pause.
“Or I could force you along to mom’s office and show off what a well-practiced makeup look you pulled off. Then I can inform her that I found this cute outfit with this sexy lingerie in your closet, telling her you must really be one big sissy and see how she reacts then.” Keira said threating using Ash’s fear against him.
Giving her words a moment to sink in she then asked. “So what is it going to be? Are you going to follow along quietly and let me take the word or are you going to interrupt and protest, so I’ll have to expose your little secret?” Keira asked already knowing what the answer would be.
Ash was stunned. His sister was right though her mother had approved of Keira dressing him up so if he showed up like this she wouldn’t really think much else about it, not unless Keira gave away his secret and he didn’t want to risk that. “I’ll come along quietly.” He eventually softly replied.
“There’s a good girl, I knew you were going to come to your senses. Now let’s go show mom her cute new little daughter. I’m sure she will simply be delighted.” Keira grinned as she pushed Ash in front of her, guiding him to their mother’s office where she knocked on the door. A quick come on in followed soon after.
With a proud smile Keira opened the door pushing her prettied-up brother in front of her in front of their mother. Beatrice instantly looked surprised she had seen the potential in Ash to make a pretty girl, but she hadn’t expected her son to make such a pretty girl with just some makeup and an outfit. It gave her very high hopes that he would make the ideal replacement for her model who was currently out after her accident. If she could launch her son as such a gorgeous trans model she could get tons of big contracts for her agency. This could turn out to be really profitable.
Giving Ash a thorough once over she had to admit that Ash did make a prettier girl than his sister did, way more of a girly girl, like the daughter she never had. Of course she wouldn’t say that, not yet at least or Ash could claim he had won the bet already and her chance of turning him into one of her models would be ruined.
“So mom, what do you think? I tried doing his makeup and to find him a nice outfit. Oh and before you say anything. I don’t think Ash is a really suitable name for him or should I say her? Ashley is a way better name don’t you agree?” Keira asked proudly, keeping her word and taking credit for his makeup and outfit so their mother wouldn’t expect a thing.
Ash was only slightly relieved that Keira held her word, but at the same time he was worried. He didn’t want to be called Ashley yet he also knew that what he wanted here wouldn’t matter. Making a fuss about it might end up making Keira reveal his secret after all and with how helpful his mother had been so far he could only guess she was all for the name Ashley.
“Well Keira I have to say you did a great job already, Ashley looks quite good. If I were you I would be worried cause with some professional help like for the shoot tomorrow Ashley could really end up looking prettier than you.” Beatrice said, trying to limit her praise of Ashley’s looks so it wouldn’t ruin her plans.
To Ash it came as a big surprise, unknowingly his mother had complimented his makeup skills and he didn’t know how to feel about it. Somewhere deep down he was proud of it, but he shouldn’t be right? God this was so confusing.
While Ash was confused about their mothers small compliment Keira wasn’t all that happy. She didn’t actually want her brother to make a prettier girl than she did, no she wanted to humiliate him and pay him back because it was unfair how easy his life had been up until now. It was unfair how he could do as he pleased while she was pressured into being a model and a girlfriend to that jerk of a Bruce.
“Just a quick dress up doesn’t really prove much though. There is so much more to being a woman than just putting on a dress and makeup. I think Ashley should at least stay a girl until after the shoot so I can teach her some more about what it is like being a woman.” Keira said tightening the control she had on her brother.
“I think that’s a great idea. Ashely for your own good you should listen to your sister. You do want to win that bet don’t you? In fact after your claim I think it’s only fair that you do your very best to prove it or I’ll be angry. Now the two of you can go, I still have work to do.” Beatrice said agreeing to Keira taking full control like Ash had feared.
Quietly they left the office, closing the door behind them as Keira whispered in Ashely’s ear. “Did you hear that sis-sy? You get to be my sister all day long and I will personally see to it that you learn all there is to learn about being a woman. Now you better play along nicely or I might just let your secret slip to mom.” Keira grinned, even though Ashley couldn’t help it she was going to regret being complimented by their mother.
Back in her office Beatrice was smiling. While walking out she hadn’t been able not to notice how good Ashley actually walked in those heels. It was quite surprising to be honest. Anyways, it was time for her to call the company behind that big contract to let them know she most likely had a replacement model. If she played her cards right, she might even pitch a better price since she could give them a transgendered model. After all diversifying your brand was key these days and rightfully so.
While Beatrice was making numerous phone calls to hairstylists, makeup artists photographers and editors to get everything ready for Ash’s shoot tomorrow. Keira was having some fun at her brothers expense. She had to admit that Ash looked very pretty, possibly prettier than her even and while it would be perfect of coupling him with Bruce and that asshole photographer, she couldn’t stand it. She had hoped he would look more like a clown with his fully made up face, that he would look ridiculous but since that wasn’t the case she would have to find another way to make him look ridiculous.
That new way to make him look ridiculous was an exaggerated mannerism training. While Ash knew how to walk in heels decently well from learning to do so in his room, she still insisted that he adopted a swishier mincing step. She wanted to make him look like a caricature instead of a real girl. At first Ash protested heavily, but under threat of his secret being revealed he eventually caved in, following along with his sisters mincing and curtsying training.
He knew that this was not how a girl walked, just like the makeup Keira had applied to his face was outrageous, but under threat he had no choice but to follow along. He wouldn’t stand for this though. As soon as Keira wouldn’t look he would go back to walking graciously like he had taught himself, just like he had redone his Makeup way better than when Keira had applied it.
Sadly for him Keira watched him very closely most of the day. She was enjoying this way to much not to do so. When she eventually grew tired of playing with her dolled up brother she decided it was time for him to go to bed, not caring that it was way earlier than he usually went to sleep. “Alright Ashley, time for you to go to bed, tomorrow is a big day after all and you’ll need your beauty sleep. Besides such a prissy girl like you needs time to get ready for bed.” Keira teased.
“First things first, strip out of your dress and heels. Then you can clean off that makeup, give your face a nice scrub, then use this moisturising cream and finally apply this paste for your night-time beauty mask.” Keira instructed handing Ash an arm load of products to get everything done as required. This part wasn’t actually so bad for him. He had used that scrub before and that moisturising cream as well, but never the mask. He had always kind of wanted to try it, but he had been too scared of being found out. Afterall the green mask needed to stay on for a while to have an effect so if anyone would enter his room for any reason he would have been screwed.
Now was the perfect opportunity though. Although it was still somewhat embarrassing to be seen with such a facial mask his sister had just given him the perfect excuse to fully indulge in a night-time skin care treatment. He tried not to show it, but he eagerly put the products to good use.
Once he was done Keira was right back with her next demand. “Alright, now for the final piece, your nightie. It isn’t really part of the set, but Bruce bought it for me once, demanding I’d wear it with this set. I never did and now it’s yours.” Keira smirked handing Ash a sheer white nylon baby doll nighty with a feathered top and bottom hem. Although it went from his upper chest to his upper thigh the nightie didn’t hide a single thing. His lingerie was still perfectly visible underneath.
To ash it was embarrassing and way too sexy to wear here with his sister, but he gave in either way. At least alone in his room he wouldn’t mind wearing this and his room was right where Keira took him. “Now my sissy brother, it’s bedtime for you. Afterall it’s already 8 o’clock. Now if I hear or see you get out of bed then I’ll be marching you straight to mom like this and you can tell her goodnight. I bet she’d love to see this.” Keira threatened making sure he would be staying in bed even though it was way to early.
Her threat worked wonders as Ash remained in bed during the entire night even if sleeping in had been difficult. Not only had it been way too early, he was also secretly excited yet worried about his shoot. It was a secret dream come true to do such a shoot, but he desperately wanted his secret to remain secret as well.
Chapter 3
The following morning Keira enthusiastically entered his room without knocking. “Oh Ashley, it’s time for your big day. Now we have no time to lose. I want you looking and smelling your Sunday’s best when we arrive at the shoot. I already ran your bath for you.” Keira said as she pulled the sleep groggy Ash out of bed, leading him to the bedroom clad in nothing but his sexy lingerie.
Helping him remove the face Mask Keira demanded him to strip completely naked after handing him a simply white bikini’s bottom. She really didn’t want to even see her brother’s genitals so he would just have to bath in the bikini. “We’re leaving for the shoot in two hours mom informed me last night. We still have to properly wash you and your hair, and of course pick you something to wear. Luckily we don’t have to do makeup or anything. They’ll be doing that on site.” Keira said as she barely left Ash any time to process things. Once he was in the bikini bottoms she pushed him into the bath which smelled strongly like strawberries.
“I hope you like the scent, I specially selected it for you. The fruitiest products I could find so you can smell like just as big of a fruit as you are.” Keira laughed as she let Ash soak for a while, allowing the scent to permeate his skin. She then took the shower head and started washing and conditioning his hair using strawberry scented products just like in the bath. She loved treating her brother like a helpless doll.
Pulling Ash out of the bath she blow-dried his hair adding a lot of volume and making the already long hair for a guy look extra girly. It didn’t really matter that much since the hairstylist would be taking care of it, but Keira really wanted her brother to look as girly as possible upon arriving at the shooting location already.
“Normally models just arrive in something comfortable for the shoot, but you aren’t just normal right. You should look your girly best Ashley, follow along.” She said before walking off to her own room with Ash in tow. Laid out on her bed was a set of sexy lingerie paired with his white high heeled sandals and a rather revealing outfit.
The lingerie consisted of sexy white lace thong cut panties, a matching bra and a garter belt paired with nude coloured stockings. Accompanying it were his white high heeled sandals, a soft pink skater skirt and a white crop top. Obviously his sister wanted him to wear different clothes than yesterday. With how tomboyish her usual wardrobe was it was also obvious that she had gone out of her way to find one of the girlier sets of clothes she owned. She never bought any skirts or dresses and doing shoots for those was pretty rare as well. Most of the time she could appease Bruce’s demands by taking lingerie shoots he liked those more anyways and they shut him up for longer.
“That’s too much Keira. Isn’t it bad enough that you made me smell like a fucking strawberry already? What would the shooting team say if I arrived in a full set of lingerie while you claim that models always arrive in something comfortable. Don’t you have a pair of leggings or such? Something more you know, casually comfy?” Ash complained.
“Oh absolutely not Ashley, you are going to wear these clothes and nothing else. They are going to think you’re a big sissy, and rightfully so. Of course mom will know I dressed you so your secret will remain safe, unless you keep being so difficult. I can always lay out a couple more lingerie sets and go complain to mom that you are going to make us late because you can’t decide which set looks sexier. Of course after letting her in on your secret that is.” Keira said with a smirk, knowing her brother would give in.
“Alright, but only when you make it very clear to everyone that you picked out this outfit.” Ash tried to bargain. If Keira took the blame then maybe he could save his secret, at least for now. He didn’t like having to appear like this in front of his mom and the full shooting team, but only out of fear of being found out. If he had been alone he would have loved putting on this outfit.
“Well of course Ashley as you wish. Now just get dressed, I’ll turn around for a moment, but it is almost time to leave.” Keira said loving her control. She could hear here brother groan which was a delight to her. She wanted her brother to suffer the same things she had had to suffer all these years. Having to dress up way girlier than you’d want or doing stupid shoots you don’t want to do. Her brother had always had the easy life as far as she was concerned.
Turning back around after she was confident that her brother was at least wearing the panties already Keira couldn’t help but notice how skilled he was at attaching garter straps to stockings, he was even better at it than she was. “My my, you sure are pretty skilled at that, it looks like a well-practiced move, not that it’s all that surprising after what I found in your room.” She mocked making him blush as he connected the last straps to his stocking top.
Once he was fully dressed Ash’s nervousness only grew. He feared being seen like this by others, the fact that Keira would take the blame was only a small relief. After all, what brother let his sister do this to him? With Keira’s threats and the fact that she was simply stronger than him he didn’t have much of a choice but to go along with her antics.
No one knew it, but the fact that his sister was stronger than him despite all the exercise he had gotten in, accomplishing nothing but some lean muscle were all testimonies to the great extend he had gone to to hide his secret. The lack of muscles and a lot of body hair were blamed on very late puberty and genetics. With how Ash exercised and even the fact that he had found himself a girlfriend. He had covered up the fact that those so-called genetics were his own doing. He had been taking underground hormones for a while now, not wanting to bulk up or get dark hair all over, mainly testosterone blockers as he didn’t want to start developing in a more feminine way either. That would have brought out his secret for sure.
He had noticed a slight swelling and increased sensitivity in his nipples lately. The change was a very subtle one, but it made him worry that those underground hormones he got might not be exactly what they said they were. After all with the unlabelled canisters of pills he couldn’t be sure. He had taken the risk however since they had so far proven to work at preventing his bulk up and delaying the growth of big amounts of body hair.
“Come Ashley it’s time to go!” Keira suddenly exclaimed yanking Ash out of his thoughts of how he had gotten himself in this situation. His constant safeguarding of his secret had directly led to it now being brought in the open. It was almost poetic how he was practically forced to live his dream, a dream he had hidden for so long. It was like the universe was forcing him to take the first step to acceptance.
That didn’t make this whole situation any less scary though. As they approached their mother his nervousness came to a peak. “My my Ashley, couldn’t wait to get dressed up? Don’t worry, there’ll be plenty of dressing up at the shoot for you. At least you didn’t put on makeup yet, good, it’s best to leave that to the specialists. You even smell pretty.” Beatrice said with a curious smile having expected her son to wear something simpler to go there.
Ash didn’t know what to say to that, but fortunately for him his sister kept her word. “Oh mom, with Ashley’s claim of how she could be prettier girl than me I couldn’t just let her put on a legging now could I? No, real pretty girly girls should look pretty all the time” Keira explained, it wasn’t the taking the responsibility Ash had hoped for, but it was something at least.
“You’re right Keira, if Ashley makes such claims then she should bear the consequences. Now it’s time to get going, or shooting location is still a little drive away and we don’t want to be late. Those professionals are costly and paid by the hour.” Beatrice said, her amused tone switching to a more serious one. As far as she was concerned Keira had the right to poke some fun at her brother after his claims. Ash did make a rather pretty girl though, even without the makeup for some reason. The chance that she would have her replacement model was looking ever more likely.
Getting into the car they drove off to their lake side house. It was one of the perks of the modelling agency Beatrice ran. Technically the house was company property, a shooting studio with nice settings to shoot all around. That had never stopped them from spending vacations there though. Those vacations had always been memorable unlike for Keira who had done shoots there rather often it was nothing but a vacation spot to Ash.
Upon their arrival there was one car on scene already, the others would probably be arriving shortly. Getting out of the car Beatrice instantly went out to greet the woman who was standing near it. The woman was of average height with a dark blue nearly black pixie cut wearing a pair of simple grey leggings, a black tank top and black sneakers. Getting out with her brother Keira was a little confused. She had done enough shoots to know all the regulars her mother hired or had under her employment. She didn’t know this woman though.
“Ah Ashley, come over here a minute. I would like you to meet Jessy, Jessy, this is my son Ash or as we’ll call him today Ashley. Jessy here will be your makeup artist and we were lucky to be able to get someone with her talent on board for today.” Beatrice introduced them as Jessy subjected Ash to a studying look. Ash was mortified though. Of course the people working on this project would know he wasn’t really a girl, but to be introduced like this was simply embarrassing.
Jessy’s studying look soon went over in a warm smile. “Ah Ashley so nice to meet you, your mother is really big on the compliments, isn’t she? It wouldn’t take much talent to make you look good for the camera.” She said embracing Ash in a quick hug while was simply stunned. She didn’t think this was strange?
It didn’t take long for Keira to interrupt the greetings. “And who are you exactly? You aren’t our regular makeup artist and I don’t know you.” She said a bit blunt in her confussion. She was already looking to introducing her brother as Ashley to the people she frequently worked with and now this new girl showed up.
“Well I’m no regular makeup artist either. I specialise in transformative makeup although it’s a bit more than that, I like to call myself a bit of a body sculptor. I’ve worked behind the scene for drag shows from time to time but I specialise in more realistic transformations. I have my own little studio where I help men, closet crossdressers or closet trans folks realise their dream of looking as realistically feminine as possible. Makeup is one part of that, but there’s so much more to it. For a lot of these people it’s hard that they can’t be who they want to be at least not freely so when they visit me I like making their dream become true, using all the tricks I know. For a lot of my clients it’s amazing to see their womanly potential and during the shoots after their transformation we make some fond memories for them to cherish.” Jessy explained.
“This is the very first time I’m working for a real professional shoot though, but well like I said it won’t take much talent to make Ashley look good for the camera so in that regard I’m more than ready.” Jessy said with a warm smile.
While Keira smiled in delight, hearing that her brother would get a very thorough makeover, Ash himself looked shocked. Not because of what Jessy was here for, but more about the professional shoot. This was just for a portfolio, right?
Seeing Ash’s concern Jessy spoke up again. “Hey don’t you worry, It’ll be fun, I promise. Nothing to be nervous about. We’ll just make you look even better in that cute outfit you’re wearing.” Jessy said trying to appease Ash. This wasn’t to Keira’s liking though, she had hoped Jessy would go more of the drag way. She wanted her brother to look over the top, not like just another girl. It didn’t appease Ash either as it was the professional shoot he was worried about.
The next one to arrive on scene was Dean together with Sarah. They didn’t need introduction as Keira immediately greeted them. “Ah Dean, Sarah, so good you guys are here. I would love to introduce you to my bro… uh my sister Ashley, she’s the model of today’s shoot.” Keira said instantly taking charge as the couple coming out of the small van giggled lightly. Dean was a tall man, with a stylish brown hairdo, short on the sides and longer on top. He would be the photographer.
Sarah his wife was a pretty blonde with straight hair looking like she put a lot of effort in her appearance. She had met Dean through her work with the modelling agency of Beatrice where she was the regular hairstylist.
Keira had only just greeted them when another van arrived. A tall dark-haired woman of middle eastern descend got out. She was here to provide the wardrobe as ordered by Beatrice. “Ah Jolene, good you are here. So with everyone here I think we can start getting Ashley ready for her portfolio shoot.” Beatrice announced, taking the lead to get everyone to move into the lakeside house.
Ash just followed along slightly overwhelmed. He had secretly always dreamt of becoming a model, but he hadn’t anticipated this. He was rather surprised that there were so many people here just for his shoot, and honestly it scared him a little, all these people seeing him as a girl. It might have been a dream come true in the strict sense, but right now it felt more like a bad dream, why couldn’t a shoot just happen with him alone in his room?
(If you like my story and would like to see more and support me please consider joining me on Patreon: https://www.patreon.com/Fibaro . If you don’t want to or can’t then don’t worry, everything will eventually be available for free, but it’ll take a bit longer to become available.)
Chapter 4
Sensing Ash’s nervousness Jessy took charge upon entering the house. She had the feeling that something wasn’t quite right with this shoot, but most of all she wanted to appease Ash a little. “Alright, if you all don’t mind I have a lot of work to do and I rather do so quietly, well at first at least. Once I’m ready with the foundations I’ll call in Sarah to start on the hair, I’m pretty sure the rest of you know how to stay busy setting up the equipment and scouting the best locations.” She said firmly.
It wasn’t much of a problem for Jolene or dean. Jolene just needed to unload the clothes in the sizes Beatrice requested, then go over them with her to select the outfits. Dean had a lot of work setting up all his camera equipment anyways. For Sarah it was a slight adaptation as usually she went to work along with the makeup artist, but she could understand that making Ash look like a proper Ashely required more time and work than just applying makeup on a female model.
The only one not wanting to miss this for anything in the world was Keira, and so she instantly complained. “I have nothing else to do than be here and watch so I’ll join you. I wouldn’t want to miss this at all, I bet it’ll be awesome.” She exclaimed enthusiastically.
Jessy had taken an instant dislike to Keira, unlike the rest of the team she didn’t know her yet, but from where she stood it looked like she wanted nothing more than to mock Ash which was something Jessy couldn’t stand, having seen way to many of her clients scared because of people like this. “You have no business watching anything but the shoot, so unless you go find something else to do in the meantime, I’ll be on my way home again.” Jessy said assertively, applying what pressure she could.
It was enough pressure to get Beatrice involved. “That won’t be necessary Jessy, we’re very happy to have you here and I’m sure Keira will find something else to do in the meantime, now won’t you Keira?” She asked her daughter raising an eyebrow to let her know she was dead serious. From what work she had seen no one in the area was as good at this as Jessy was. If she wanted the best possible chance to pitch Ash instead of that model who had fallen on her face then she needed Jessy. Besides if Jessy left not only would she lose the best for this task, but also the only makeup artist present.
Keira wanted to protest again, she wasn’t happy with how Jessy was ruining this opportunity to further mock her brother at all. With her mother’s stern gaze she could do nothing but give in though and the more she thought about it, the more she realised she had to take a step back. Without Jessy there would be no proper shoot at all. “Alright, I’ll go for a walk.” She finally said reluctantly.
“Great, Ashley, would you mind following along? It’s about time we’d get started.” Jessy said entering one of the bedrooms which had been changed to makeup and dressing room. Quietly Ash followed along deeply grateful for how Jessy had stood up to Keira. He didn’t look forward to being ‘transformed’ in front of all these people, but if it needed to happen anyways then he was glad it would be Jessy who would be doing it.
Jessy led Ash into the room then quickly went over to her car to get her stuff before coming back, locking the door to the room so they certainly wouldn’t be disturbed. “Hey Ashley, don’t worry to much about your sister and her mockery. I think you look gorgeous already and with a little help I’m sure you’ll shine like never before. Now I know that this probably isn’t quite comfortable for you, but I’m going to have to ask you to strip, and that pretty much completely I’m afraid. I was informed that you’ll modelling lingerie as well and there for a gaff is definitely advised, do you know what a gaff is?” Jessy asked patiently and warmly.
It came as a bit of a shock to Ash, but at the same time her tone also put him at ease slightly. “I know what a gaff is.” He replied softly. He had come across it a couple of times during online searches, but he had never actually seen one up close or worn one.
“Great, if you want you can put it on yourself and I’ll give you some privacy to do so, if you need help however you can always call out for me.” Jessy said respectful of Ash’s privacy. She then handed him a small skin coloured thong style thing that looked slightly padded at the crotch before turning around allowing him privacy.
Slightly embarrassed Ash took the garment and first stripped out of his current clothes. He then followed what he had once read online, pushing his balls up in their cavities before tucking his penis back and pulling the tight gaff in place keeping everything flat, giving him a crotch that resembled that of a barbie doll. “I’m done.” Ash spoke softly, grateful for how patient Jessy was being. She managed to put him at least a little at ease in this nerve wrecking situation.
“Alright, up next I’m going to help you with some silicone hip pads and breast forms, once they’ll warm to the skin they’ll feel pretty realistic and with some makeup to blend them exactly to your skin they’ll look real as well. This can be a little shocking to most people as it really does create a nice hourglass shape, but after a little getting used to the sight most people are thrilled with the look it offers them.” Jessy carefully explained the next steps, taking out the silicone forms closely resembling Ash’s skin tone.
“So Ashley, are you excited for your very first shoot as a girl? How comes your sister is being such a pardon the word bitch though? “ Jessy asked making some small talk while trying to get a better grasp of the situation after seeing the interactions with his sister and the slight fear in Ash’s eyes she had somewhat mixed feeling about this project.
Ash remained silent for a few minutes, not really certain about what he should or shouldn’t say to this woman. Jessy didn’t push though. She just casually kept on working, rubbing the glue for the hip pad on the entire area of skin they would cover as if it was the most normal thing in the world.
Eventually Ash decided to open up anyways, if only to break the silence. Jessy was being very nice and non-judgemental. The whole vibe he got of her was one of support and casual acceptance as if this was just a normal situation. On top of that he also just felt the need to vent what had happened and there was no one else he could really vent to without revealing his secret he so desperately guarded.
“Well I wasn’t supposed to be here, this wasn’t supposed to happen. I just kind of stole one of my sister’s skincare products then somewhere in the confrontation I said something along the lines of that even I would make a prettier girl than she did. Then the argument got heated and she drug me to my moms office. My mom basically agreed that I should put my money where my mouth is and prove that I could make a prettier girl.” Ash started.
“This then led to her claiming I shouldn’t be expected to know how to do makeup and such as well as my sister so that for the most objective view we would need professional help and a professional shoot. I guess this is it.” Ash finished.
Jessy looked up somewhat shocked. “So you mean to say that they forced you into all of this because of a stupid bet made during an argument? I’m sorry, but I won’t participate in that kind of thing.” Jessy exclaimed dead serious.
A wave of panic rushed over Ash, what would his mother say if he ruined this, besides, as nervous as he was, there was also a small voice deep inside of him that wanted his secret dream of becoming a model to become reality. “Wait!” he screamed out making Jessy who was already on her way to give Beatrice and Keira a piece of her mind freeze in her tracks.
“It has also always been somewhat of a fantasy of mine, but no one knows, and please don’t tell anyone.” Ash blurted out, shocked that he literally confessed his secret to someone. His sister might have had a glimpse of his secret when she found that outfit in his closet and saw his makeup skills, but now he had gotten the full extend of it out for the first time in his life. It came as a shock to him, but also as a huge relief.
Instantly Jessy’s determination to stop this ended as she made her way back to Ash with a compassionate look on her face. “Oh sweetie, don’t you worry, I’ll keep your secret. I promise. Now I understand why you’re so nervous, but if it’s any help, you do make a very pretty girl. I understand that giving in to your true self, especially one so different than the body you have gotten and the way you have been raised is hard, but please don’t let that get in the way of enjoying this. Besides your secret will remain safe as you have the perfect excuse for this shoot right?” Jessy said compassionate, trying to put Ash at ease so he could enjoy this secret fantasy.
“Now let’s continue getting you ready shall we?” Jessy asked as she went back to work applying the other hip pad before using her makeup kit to make the pads blend perfectly to Ash’s skin. When she started applying the glue for the breast forms she was surprised to feel and see the light swelling that was consistent with some of her clients on hormones. With how badly Ash wanted to keep this secret this raised an alarm in her head though.
“No one knows about this secret of yours, right? Also not your doctor or anyone like that?” Jessy asked trying her best to not sound worried. She wanted an honest answer, but this was too important to let slip so she needed to be slightly persistent as well.
“Of course no one knows about it.” Ash blurted out.
“Oh I just thought that at least your mother or doctor would know since you are on hormones.” Jessy replied casually curious to see his reaction. She didn’t want to upset Ash at all, but wanted his shocked reaction told her all she needed to know. Just like she feared he was on underground hormones. She had seen it happen a couple of times already and while it wasn’t instantly harmful messing with things like that unregulated could cause big trouble.
Before he could speak up Jessy took the word. “Look Ash, I’m not mad and I don’t want to upset you, but I would like to urge you not to take those underground meds, they can really mess with your body in a bad way if you aren’t careful. You’re old enough to go to a doctor on your own and make the decision yourself, but if you want I could come with you. Your family doesn’t have to know, at least not yet, but it’s important that if you want to stay on hormones that you follow a regulated program. Of that I can assure you.” Jessy said voicing her concern.
Ash didn’t really know what to say, he had never really thought about the dangers, only the results, but he realised this woman might be right. He still didn’t know though, what if his mother would find out? “Just think about it okay, and please don’t take those underground meds anymore.” Jessy said concerned but judgement free.
Shocked Ash just stood there. He had been on these things for a while and he had been concerned when he had started feeling the slight lumps form at his nipples. They were still very small and practically invisible. They were most noticeable to the touch which had allowed him to get away with keeping his secret all this time. It was something he wanted to keep this way, but feared he would be unable to if those lumps kept growing. Still he had always pushed it away as worries for later.
Apart from those small but growing lumps he had never really worried about any other dangers, but Jessy was probably right. He’d better stop using these black-market hormones all together. Going to a doctor was probably wise as well, but that would get him an official record and he was terrified that his mom or god forbade his sister would ever find out his secret. It was crazy in a way, that Jessy this girl he had only just gotten to know already knew him on a way deeper, more intimate level than anyone else. He had never confided his secret to anyone before.
“I just took them to keep myself from bulking up while working out, so I could just blame my lack of beefy muscle growth on genetics. You’re right though, I should probably stop, but if I suddenly stop working out it won’t go unnoticed and I don’t want to bulk up.” Ash finally said to Jessy who was sticking the breast forms to his chest now.
She gave him a compassionate smile back. “I’m very glad you agree that those things are bad for you and if you want I know a doctor who’s specialised in these kind of things who knows how difficult it is to be yourself in the face of judgement. She can definitely arrange to make this strictly confidential to the point where even your family doctor won’t know. Of course if you get other meds you would also have to contact her to see if it won’t have a negative effect in combination with your hormone treatment.” Jessy said seeing how Ash remained worried none the less.
“If you’re still worried about those potentially bad side effects, you can stop now. I mean you look very healthy to me meaning that there probably isn’t a problem yet, but one wrong batch could mean a disaster so it’s important to stop it either way. If you decide to continue with this hormone treatment in a regulated fashion however you will have to come clean to your mother and everyone eventually. Those lumps will only grow in time and you won’t be able to hide it forever. It’s not an immediate issue just yet, but you need to be realistic as well.” Jessy said.
“Yeah, I know, it’s just what will they think or say if I tell them?” Ash replied mainly thinking about his sisters Laughter and the way she’d probably try to humiliate him over it.
“Well I can’t talk for your sister as she does seem to have it out for you, but the fact that your mom hired me and set all this up at least means she is somewhat open to the idea already. Of course I don’t know how she’ll react, but I don’t think she would have set all of this up if she just wanted to let your sister make fun of you now would she?” Jessy argued.
Ash had never really thought about it that way, but she was probably right. This was a whole lot of effort just to make fun of him meaning that this probably wasn’t to make fun of him in the first place. It made him feel a little better about this whole situation already.
“Besides just take a look at yourself, you’re gorgeous already. You don’t even really need the makeup to look amazing. You look rather passable already now that you’ve just gotten a more feminine shape.” Jessy commented as she finished blending the hip and breast forms to match Ash’s skin perfectly. Turning him towards the big full-length mirror she giggled lightly when she saw the shocked awe spread across his face.
The shock mainly came from not being able to believe what he was seeing. Jessy was right, he did look gorgeous, his waist might not have been pulled in but the pads definitely provided an hourglass figure. If anything Ash looked pretty much like a barbie doll of sorts, mainly because his crotch was entirely flat. The shock quickly turned to admiration as Jessy just stood there smiling at the side. This was the exact look she always went for, the look that made her job so very worth it. Seeing her customers who often had issues with their bodies admire themselves like this was the best thing ever.
Still amazed by his appearance Ash poked his breast forms. They looked so very real even though he knew and could feel that they weren’t real. It was amazing yet somewhat freaky as well, how would his mother and sister react upon seeing him like this?
“I can imagine you’d want to cover those up before I call Sarah in for your hair right? I was told that these would be part of your first outfit.” Jessy said holding out a soft pink lacey push up bra and matching thong. It was a very sexy lingerie set one Ash took an instant liking to. Weirdly enough, he actually felt somewhat okay imagining having to model it. Seeing the work Jessy had already done had boosted his confidence by a lot. He knew he would be able to count on her to do a magnificent job on the makeup as well. Jessy had been right the best he could do was just enjoy the ride and the shoot. It was after all one of his dreams and Keira forcing him gave him the perfect excuse to still maintain his secret.
In no time Ash was dressed in the sexy ensemble, smiling broadly at his reflected image. Hooking the bra behind his back didn’t give him the slightest bit of problems. With the lingerie he looked even more like a real girl than he had before. Especially thanks to the panties. They covered up the weirdly flat groin created by the gaff in panties it looked nice, without the sexless part just looked rather alien.
“You can also put this on for a bit of extra coverup while getting ready if you want. It’s the way most models are dressed in the make up room so…” Jessy started but was cut short when Ash suddenly pulled her in for a tight hug, giving her a kiss on her cheek.
“Thank you so much Jessy, you have done an amazing job, I was insanely nervous for today, to the point of dreading the whole experience but you have helped me a ton. You’re the best.” He said as he let go an took the white silk bathrobe Jessy had offered him to wear. Throwing it on Ash arranged the garment in such a way that it showed a slight bit of cleavage, the very cleavage Jessy had just created. It still felt somewhat wrong, but it also felt so right at the same time.
His little action didn’t go unnoticed by Jessy who was smiling broadly. Ash had certainly blossomed a lot in the short time they spent together and seeing it really warmed her heart. For a moment she had thought about quitting this job when Ash had informed her that he was forced into this, but right now she was so very happy that he had come clean to her about his own desires and secret after all. Maybe this shoot could prove to be a first step to self-acceptance for him making it worth way more than the money she would make of this for Jessy.
“Alright, can I call Sarah in for your hair while I start on your makeup? Jessy eventually asked after giving Ash some more time to admire himself now that he was somewhat dressed. The silk bathrobe didn’t do much as far as cover up went, but it preserved some modesty at least. That and it actually made him feel slightly sexy.
“Yes, I’m curious to see what I’ll look like once everything is done, I’m sure it’ll be spectacular. Just one request, can you please remain quiet when she’s in here? I mean definitely as far as my secret and these hormones go. If she knows then surely Keira will know shortly after and if she does then I won’t hear the end of it.” Ash requested somewhat nervously yet slightly excited as well.
“Of course, no one will hear a word from me. It isn’t to me to decide when and to who you talk about this. Just know that you’re always free to chat about it with me if you wish. I’ll give you my number sometime later on and if you’re ever in need of a talk and you don’t have anyone to talk about what you want we can always meet up. The same goes if you want to take me up on that offer to accompany you to the doctor.” Jessy said with a kind and reassuring smile.
Put at ease Ash took place in the makeup chair, trying not to show the inner excitement he felt towards getting all prettied up by professionals, afraid Sarah would otherwise pick up on it. Jessy left the room for a quick moment and about a minute later she entered the room with Sarah who had a big grin on her face, a look that quickly changed into a dropping jaw as she noticed the amazing transformation Ash had been through so far.
Quickly recovering she spoke up. “Oh my god Ashley, is that really you? I can hardly believe it, if I didn’t know better I would have thought you were a real woman, I mean that cleavage just looks so realistic that and you don’t have the most manly face either especially not with those thin brows.” She gushed. It was clear that at the start she had entered with the idea of poking some slight fun at him, but seeing the results so far it was hard for her to be anything but amazed;
“Thank you, it took a lot of practice to learn how to play around with blending and shadows this much. Now do you need any help with the hair? Otherwise I’ll get to work on the nails.” Jessy spoke up, diverting the attention away from Ash who looked a bit uncomfortable with Sarah’s excitement.
It worked perfectly as Sarah instantly turned her attention to Ashe’s hair. “Oh no, no help needed at all. Her hair is really well kept and shouldn’t be giving me much trouble. I think the best approach for this shoot would just be adding some extensions and giving it a good brushing and slight curling to add some volume and a slight wave for a seemingly effortless glamourous hairdo.” She said assessing the situation in a way that it would be perfect to pitch in a portfolio destined for a hair product ad.
“Great then I’ll get to work on her nails, I’ll save the makeup for once you’re done with the hair.” Jessy commented mainly staying quiet like Ash had requested. Sarah also became rather quiet once she started on his hair, selecting the right coloured extensions and starting the laborious task of weaving them in with his real hair before cutting it up till his hair now reached his mid back. Ash was rather surprised at just how much extra weight these extensions added.
While Sarah was busy with the hair Jessy gave Ash a French tipped manicure and pedicure. For his hands she applied a set of one-inch gel nails, shaping them in neat ovals instantly making his hands look daintier and more feminine. While Ash was a bit nervous about these changes, he did secretly like the full beauty treatment he was getting. He didn’t show it though afraid of what Sarah might think.
The whole treatment took nearly an hour and when Sarah finished up his hair Jessy addressed her once more. “Could you please leave now while I do the makeup? I want it to be a surprise when it’s done and it’s time for the reveal.” She claimed to the hairdresser, searching for an excuse to get her out of the room so Ash could talk more freely once more.
“Oh okay, sure thing, you’re the artist. I’m really curious to see how it’ll turn out. I bet it’ll look amazing, I mean it already does so I’m sure of it, but I’m still curious.” Sarah said somewhat excited, not bothering to argue. While she did want to stay to watch she was also looking forward to be blown away by the full metamorphose.
Once she was gone Jessy excitedly covered up all mirrors. Ash might not have been turned to one and so he hadn’t seen his new hair just yet, but she had to admit Sarah really knew what she was doing when it came to hair. Ash’s new locks simply looked amazing. She didn’t want to keep secrets from him, but at the same time she wanted to see his reaction once the full effect was revealed. She was certain he would love it.
“Now forgive me for covering up the mirrors, but I really want to see how you’ll react to the full-on transformation effect. Are you willing to allow me that small pleasure?” Jessy asked excitedly as she picked up her brushes and makeup to start working.
“Uhm yeah sure, I trust you. By the way having my hair and nails done like this did feel really nice I have to admit that. Can you maybe explain how you applied everything afterwards so maybe I can take a shot at it if I really like the look?” Ash asked, visibly relaxing now that he was alone with Jessy once more. It was strange but pleasant to be able to trust someone so completely even though they had only just met.
“Most certainly, I’d love to show you for sure. To be honest your face is way easier to work on than most of my client’s faces. You have rather delicate features already so I’m certain the end result will simply be amazing.” Jessy exclaimed excitedly, very pleased to hear that Ash trusted her.
For the next half an hour she attacked Ash’s face with a variety of brushes and tubes before finally stepping back to have a last check up of her work and to see if anything needed to change. Inspecting his face carefully she was very proud of her work. Ash came out looking way better than even she had imagined. One of the trickiest parts had actually been to give his thinly plucked brows a more voluminous yet natural look.
The entire look revolved around keeping things natural while enhancing his eyes and lips a little to really make them stand out. Since Ash would be posing for a variety of vastly different things, ranging from casual to classy and even boudoir shots, Jessy had determined that natural would be the best look. His eyelids were had received a very light smoky coating along with some eyeliner and mascara too make his bright blue eyes really stand out without being too noticeable or tacky. His lips had gotten a slight redder coating with a wet look to them enhancing them in a subtle way.
“Alright Ashely, are you ready for the grand reveal? I’m honestly jealous of just how great you’re looking right now. You can rival the prettiest girls if I do say so myself.” Jessy said excitedly, building Ash’s curiosity. Ever since Jessy had covered up those mirrors his curiosity had grown even though he hadn’t really looked in the mirror after Sarah was done with his hair.
“I’m ready, please just uncover those mirrors, I’m dying to see how I ended up looking.” Ash said sharing in Jessy’s excitement. Her excitement told him that he probably ended up looking rather good, but nothing could have prepared him for the absolutely spectacular end result when Jessy finally uncovered that mirror.
Staring back at him was a girl that looked like she had just stepped off the cover of a magazine, a gorgeous blonde with long wavy hair and a pretty face, just a hint of pink lace teasingly sticking out of her bathrobe’s cleavage. In complete disbelieve Ash brought a hand up to his shocked mouth only to see the woman in the mirror raising a perfectly manicured hand to her gaping mouth. The work Jessy had done nearly felt like magic seeing this spectacular end result. He really did look like a woman, a gorgeous one at that. He knew full well that it was mainly makeup, shading to make his facial features even more delicate, a gorgeous hairdo and of course the prosthetic pads. This was by no mean something he could do on the daily, at least not in this spectacular fashion as everything combined had nearly taken four hours to put together.
It was however a glimpse at how gorgeous of a woman he could make if he followed a real stronger but regulated hormone treatment instead of the black-market testosterone blockers he took now. Overcome with joy he pulled Jessy into another tight hug. “Oh god this is unbelievable, thank you so very much for all of this, this is spectacular, exceeding all my expectations.” Ash exclaimed before blushing and lowering his voice a little, afraid that people outside might pick up on the conversation and figure out his secret.
“You are very welcome honey and If I’m honest you’ve exceeded my expectations as well. You look gorgeous. Now are you ready to show yourself to the others and start your shoot? I know you must be nervous, but just try to have fun. Your mother hired me, your sister set you up, and I just did my job. No one has to know how happy you are with this makeover until you’re ready to tell them.” Jessy told him, it was probably still too soon for him to truly see that he didn’t need to be embarrassed over who he was, but if he could start out enjoying his shoot without worries it would be a huge step in the right direction and Jessy fully planned on making it as enjoyable as possible for him.
Despite her words of encouragement however she could see the nerves and worries return to his face, knowing it was time to show himself to the others. He knew Jessy was right and that it was silly to be embarrassed about this situation he was forced into yet he just couldn’t help it. His new look did give him some increased confidence however and after taking a few deep breaths he finally opened the door and stepped out in the hall, heading to the living/shooting room nervous, but also proud in a way.
As the door opened everyone immediately turned their attention to him and just like his jaw had dropped before seeing the results so did everyone else’s. Even Keira, who had looked bored at first having had to wait for so long without being able to poke fun at her brother like she imagined she could today, looked genuinely amazed. Keira’s amazement quickly soured into a somewhat angry look however. She was jealous beyond believe, jealous that Ash really made a way prettier girl than she ever could and angry that her plans to maker her brother look and act as the biggest sissy freak possible had been soiled. Instead he ended looking like what even she had to admit was a gorgeous woman and she knew everyone else here thought so as well.
Beatrice had to do more than a double take seeing her son all made up like he was. If she didn’t know any better she would have thought that Ash had sneaked out of a window out back and a female model had taken his place. His resemblance to herself when she was young and still a model was freaky for sure, hell Ash possibly looked even more gorgeous than she had been so many years ago.
Ash looked every bit like the gorgeous daughter she had always wanted to follow in her footsteps. In away it was a pity, a pity that he was actually her son and that this was all just for a day. One thing was for sure though, if this didn’t convince the hair product company that she had found the perfect suitable replacement for their original model of choice then she didn’t know what would. Hell Ash looked better than that girl ever did even if she did say so herself.
(If you like my story and would like to see more and support me please consider joining me on Patreon: https://www.patreon.com/Fibaro . If you don’t want to or can’t then don’t worry, everything will eventually be available for free, but it’ll take a bit longer to become available.)
Chapter 5
Beatrice was the first to regain her composure. Not because she was over how amazing Ash looked, but because as the director of this shoot she needed to be professional. “Alright Jolene, I believe you can take it from here. You got the shooting schedule right?” Beatrice asked trying her hardest not to stare at her son too much. The change was shocking to be honest. Never in a million years had she thought Ash would come out looking this good.
“Yeah, right I’ll get my stuff.” Jolene said forcing herself to snap out of it as well. This was her first time working with a trans model and while at first she had been nervous that she would have a hard time selecting outfits for him or should that be her? That nervousness had now completely disappeared. This would be just a job like any other as far as selecting clothes went. Ashely looked good enough to probably even pull off just wearing a trash bag. He job would be very easy.
Ashely herself felt overly excited. Everyone’s reactions had been so much better than she had ever dared dream of. At the same time a slight sadness filled him as well though. This was only for a day. After today he would just be back to his plain normal self. Then there was also a slight nervousness. He could tell that Keira was pissed and it scared him to no end. No matter what happened he knew his sister would come after him. Maybe not right away, but the moment they were alone she would try something.
A few moments later Jolene rolled in two big racks of clothes and pushed them into the room he had just come from. “Alright Ash, follow me please.” Jolene said casually trying her hardest to just make this business as usual. She had to admire this guy doing a shoot like this all dressed up and made up like a girl had to take balls and she wanted to treat him as normal as any other model. No need to make this more awkward for either of them. She was a professional after all.
While Ash disappeared back into the changing room Sarah poked her friend Dean. “Quite staring ass hat or I’m going to become jealous.” She giggled jokingly at Dean who obviously had a hard time wrapping his head around what he just saw. He always tried to keep an open mind, but he never imagined he himself would ever have a crush on a guy. It just felt somehow weird, but he didn’t mind. After all no one could blame him after seeing how hot Ashely looked right, shifting uncomfortably he had to adjust something in his pants.
“See, I told you she looked spectacular right? I mean just wow. Keira your brother really is a hotie I mean wow, just wow.” Sarah spoke in sheer awe. Unlike Jessy she hadn’t been able to see the potential, then again she had never really worked with guys dressing like girls and she was simply blown away by the result.
“I guess he looks okay yeah. I mean Jessy did a really good job that’s for sure.” Keira said somewhat reluctantly, complimenting Jessy as she didn’t want to compliment her own brother. Inside her anger only grew though. This was all so fucking unfair and she hated it. How the hell could that shit head look so much better than her? On top of that it seemed like she had just lost all allies in mocking her brother. Just great.
Jessy who had been observing everything from the side was very pleased. This deep routed fear Ash had wouldn’t just disappear from one day onto the next, but all the positive reactions should certainly help in making him feel a little more comfortable in his skin. She was very pleased that not only had she been able to show Ash what an amazing girl he made, but that she had also been able to show the others, all of whom looked pretty convinced.
Back in the changing room it was just Ash and Jolene. Keira hadn’t felt the need to join them now that she realised she wouldn’t be able to mock Ash anyways. “Alright Ashely, I believe you already put on the base for the first outfit. Would you mind dropping that robe so I can see?” Jolene asked as casually as she could.
When Ash dropped the robe however she couldn’t help but catch herself staring once more. His crotch looked so flat and those breasts so realistic. It was simply shocking. Quickly regaining her composure Jolene spoke up once more. “Alright, Looks like you just need a garter belt, a pair of stockings and a pair of heels to make this first outfit work. We’re going to shoot a number of different things. The first shoot will be in lingerie.” Jolene explained as she handed ash a matching pink lace garter belt, a pair of nude coloured sheer nylon stockings with a broad pink welt, back seam and Cuban heel.
Ash had no problems at all putting on the garter belt. He didn’t have any problems with stockings either, forgetting how this wasn’t really normal for a guy to know after the confidence boost he had gotten from Jessy. He simply rolled the delicate nylon material up in a doughnut which he then expertly rolled up his smooth leg. Stockings were really his favourite piece of clothing. They just felt so sexy and good on a pair of smooth legs.
Jolene was somewhat shocked seeing how easily he managed his stockings. It was something she usually had to help many models with, but Ash seemed to have an appreciation for just how delicate the material was. There was no way that this was his first time doing this. Hell he even took care of the back seam. It was even more surprising after working with Keira who always treated the material rather brutishly. Jolene always brought extra stockings along if she knew they were for Keira. The girl simply did not learn or care.
With one of the stockings rolled up his legs Ash then took the other and repeated the process before attaching the garter straps, front and back with relative ease, once again checking to see if his seams were straight. This baffled Jolene even more. Back garters was something she needed to help nearly every model with, especially if the stockings were seamed, yet Ash put them on perfectly without help. When he looked up and saw the surprised look on Jolene’s face he blushed. There was no way this woman didn’t realise he had had practice at this. In any case it was too late to fix that now.
“Good now all you need are the heels. It’s important to take smaller steps and walk heel to toe when wearing them. If you walk nonchalantly or take big steps you might lose balance and trip. Just keep your back straight and imagine you’re walking a tight rope.” Jolene said helping Ash in a pair of very high lacquered pink heels. She supported him for the first steps which assuming that as a guy Ash wouldn’t be able to walk in heels, especially not ones this high. When he seemed to have no problem with them however she quickly let go, not all that surprised after what she had seen when he put on the stockings.
“Alright, I guess my work’s done for now. You’re ready to go for the first part of your shoot. I just know you’re going to do a fantastic job.” She said encouragingly as she opened up the door for Ash to enter the living room once more. The room where Dean had set up the scene to shoot.
Just like last time everyone went silent once more as Ash, now quite a bit taller and looking just as realistic even though he was now only clad in lingerie emerged. “Damn, I still can’t believe she isn’t like a real girl.” Dean exclaimed a bit too loud.
“Ah Ashely you look fantastic. So are you ready to start shooting? If you need a moment that’s fine as well. We’re ready when you are.” His mother said trying to put her dressed up son at ease. After all it was important for a good shoot that the model felt at ease.
“I think I’m ready.” Ash said somewhat nervously as he trotted forward, stepping on the set Dean had prepared. It consisted of the huge white leather couch usually just standing in the living room. White faux fur blankets and pillows along with a solid pink background screen matching Ash’s lingerie.
Stepping on set Ash stood around quite awkwardly. This was the part he really had no clue about. Sure he liked striking poses in front of his mirror when he played dress up, but now that he was on the set for his first ever professional shoot he didn’t know what to do with himself.
Once again Beatrice couldn’t help but notice how natural Ash seemed at walking in heels. She didn’t comment on it though. No now the shoot was the most important thing at hand. There was no need to potentially embarrass her son. Especially not with how he was slowly starting to feel at ease. “Alright Ashely. Why don’t you sit down in the centre of the couch? About right here. Place your feet slightly apart, rest your elbows on your knees and let your arm hang in between them. Try to give a serious look in the camera.” Beatrice said as she helped position Ash who was feeling nervous but also excited.
Stepping back Beatrice could see the nervousness show on his made-up face. “What’s wrong sweetie? Look I can understand you’re quite nervous about this, but there is no need to be. You look amazing and I’m sure you’ll ace this shoot. Now try to relax. Breath in and out, deep breaths. You can take as long as you want. When you’re ready just try to give the camera a serious look. Imagine Dean just said something clever and deep. Obviously you need to use your imagination for that one, but try.” Beatrice offered, throwing in a joke to lighten the mood a little.
Dean helped along by pouting lightly while everyone shared a giggle. It did help a little, but he wasn’t quite there just yet. It all got ruined when a frustrated Keira tried to push her own agenda through. Fuck all this bull shit she wanted to embarrass her brother and so she suggested. “Why don’t you just make him do a limp wristed wave and a giggle? I’m sure those come much more natural to the sissy.” Keira said viciously as the room fell quiet and Ash’s nerves returned full force.
Beatrice turned around and Keira instantly knew she had fucked up. Her mother looked pissed. Making her realise she had gone too far, at least further than this situation allowed. She would have loved nothing more than to see her brother perform what she had just said, but it didn’t fit with the genuine shoot everyone else wanted to participate in.
“Keira! You’re insufferable today. You were the one who insisted on this bet. As far as I remember you were more than eager to take this all the way, to do this shoot, to give Ash the best possible chance to either win or lose the bet. It isn’t because you are about to lose that you should be a bitch about it. I’m heavily starting to suspect that you’re the sore loser here instead of Ash. One more interruption like that and you can take the bus home. Now get out of here while we do this shoot cause I have a feeling it’s you who are making Ashely nervous.” Beatrice ranted to her shocked daughter.
“But mom!” Keira started trying to build herself a defence.
She was instantly cut off by Beatrice though. “No buts, get out of here right now or go home if you think you can behave you can come back but I don’t want to see you here again for at least the next hour. Go take a walk or something to cool off.” Beatrice reacted firmly, having lost her temper.
Knowing better than to continue arguing Keira just cursed under her breath and angrily stormed out of the lakeside house, taking her mother’s advice and going for a walk. She was pissed out of her mind, but without allies to humiliate her brother there was nothing she could do. Ash should count himself lucky. At least until she had him alone once more. Oh he might be safe now, but he would pay eventually. That’s what Keira told herself as she walked along the lake’s side.
Back in the house the peace had returned. Everyone had gone completely quiet after Beatrice’s outburst actually somewhat scared to face her anger as well. Beatrice was professional enough not to let that anger shine through to others though. “Where were we. Oh yeah, Ashely sweetie. You just try to throw a serious look in the direction of the camera.” She said taking a pleasant tone again. The sigh of relief going through the room was nearly graspable.
To Ash it came as quite a surprise to have his mother stand up for him like she did, and that against his sister who nearly always got what she wanted. It felt good though to be supported like this. Together with the removal of Keira from the room it did really help his nerves. Adding to the support Jessy put her thumbs up and gave him a sweet smile.
Finally feeling a little more confident now everyone present seemed to accept him like this Ash was able to put on the serious look his mother had requested. “Perfect!” Beatrice commented encouragingly as she shot her made up son a bright smile while Dean took shot after shot, narrowing down the best ones was something to be done after the shoot.
“Now lift one hand up to your cheek and imagine Dean told a really fun joke. Yes I now, there’s a lot of imagination involved here.” Beatrice said with a smirk, gently guiding her dressed up son through the poses, directing him in ways that would work best in her opinion.
From sitting on the couch she directed him to lay down, to stand, to act like he was adjusting his stocking,… At the start it had felt a bit awkward to direct her son in how to seductively pose in lingerie, but he was playing along perfectly. Soon Beatrice managed to put herself over her slight reservations and look at her son as if he was just another model and they were trying to sell a product. It worked out great for the both of them when that awkwardness disappeared as it was one less distraction.
Soon Ash was able to forget all about his nerves and just enjoy life as Ashely, the professional model he had always dreamed off being. No one in the room gave him any funny looks. At least not once they had gotten over their amazement of how good she looked as a girl. After that everything just changed into pretty much a normal shoot. Not only Ashely was genuinely smiling, but so was Jessy. This was the entire reason she did what she did. She loved helping her clients on a path to self-acceptance.
After the lingerie shoot the background was changed to a plain white one and Dean took close-up shots of Ashely’s face and hair. Sarah performed a few light touch ups to the hair in between shots, but even from this clos up angle Ash looked amazing thanks to the amazing make-up job from Jessy and his naturally pretty features.
From the close-ups things progressed to the shooting of a long stylish evening gown. Then to a more playful summer dress, followed by a casual pair of pants and a t-shirt. Eventually they changed locations to the home gym looking out over the lake to shoot a workout outfit. Beatrice wanted to add as much variety as possible in this shoot. It would make Ash’s portfolio all that more desirable. It would also make things way easier to pitch Ash for a wide variety of fields in the future. A future that was looking very bright judging from the results they were getting.
“Jessy, quick question. How well will your makeup and work hold up against water? Can we risk a waterside shoot? Maybe even in the water?” Beatrice asked as they wrapped up the workout part of the shoot and Ash went back to the dressing room with Jolene.
“I guess a dip in the water should be possible without ruining the look. The only thing that might fail is the makeup, but unless you use makeup remover or soap I don’t see it getting ruined that easily. Still I would advise to do the in the water part last of all just to be sure.” Jessy suggested, her job here might have been done for a while already, but she was more than happy to stay along for the shoot. It was wonderful seeing Ash blossom like he had.
The shoot might have been going strong for a few hours already, but Keira had never returned. Her walk did nothing to appease her. It only made her angrier. Why did her mother have to ruin this just when she had Ash right where she wanted him? It had originally been a threat from her mother, but the more she had thought about it the more she was in favour of the idea. She had no desire to see all the supportiveness and care for Ash. This was supposed to be her day, her time to shine, her fun at humiliating Ash. Instead it had all been about him.
If she couldn’t have what she wanted then she might as well go home and come up with a way to get what she wanted anyway, maybe not now, but soon. Very soon. Keira didn’t bother to let her mom know that she had gone home.
Back at the lake side house Ash had been dressed in a simple yet sexy neon pink bikini. It looked amazing on him, just like every outfit he had put on had. All his working out, the underground hormones although Jessy had made him realise how dangerous those were and Jessy’s work had made sure of that.
As he was led out Ash was giddy with excitement, seeing the surfboard at the lake side. This was the exact kind of shoot he had always been dreaming off. His excuse of the surfer dude to though hiding his real desire to be the bikini model in a similar setting.
By now Ash had slowly turned out being a natural at modelling. His confidence was way up. All the tips from his mother as far as posing went at the start of the shoot had paid off big time to the point where he now pretty much found the best positions on his own, even improvising from time to time. It had actually turned out being so much fun that he nearly forgot that he was trying to hide the fact that he was actually enjoying this.
Modelling with the surfboard was a blast. It looked extra spectacular with the setting sun over the lake. While the water was on the cold side Ash was simply out of his mind when he got to go in the water, recreating those very same pictures he had idolised over and over again. Although he didn’t spend long in the water it was amazing. Coming out he was cold though. His mother waiting on him with a thick cosy towel.
“You did amazing honey, I’m proud on you. Now why don’t you follow Jessy, ask her to help you with taking everything off and take a nice shower to warm up again?” Beatrice offered nicely. She was very pleased with the results of the shoot and what she had seen today only confirmed her suspicions of these past few days. Ash was a little too good at all of this and he had a little too much fun to supposedly hate it. Not that she minded in the slightest. He seemed happy and it also made for a nice business opportunity for her. Maybe he would be up for more of a career instead of just helping her out with the difficult situation of the model who had fallen.
“That sounds like a plan.” Ash said now a little shyer again. The shoot was over and he realised he might have been acting way too happy modelling all those outfits. The self-doubts and self-consciousness returned once more full force. Jessy was right there waiting for him though. Wrapping an arm around his towel wrapped torso she guided Ash back inside while Beatrice remained behind handling business with the others.
“Your mother is right. You really did amazing Ashely, now let’s get you all cleaned and warmed up.” Jessy said sweetly. Ash might not fully realise it yet, but she had seen that his mother knew something was up. She had seen that she seemed to support it and that made her happy. She would of course keep her promise and not tell a soul about what Ash confided to her, but knowing that he would be met with support when he decided it was time to come out filled her with joy.
“So did you have fun sweetie? What was your favourite outfit to shoot in? It seemed like you manged your nerves really well, but did you? I hope you weren’t too concerned while shooting.” Jessy asked once they were out of earshot, genuinely curious to know whether Ash’s enjoyment had bee a charade or if he had stayed nervous only hiding it well.
“I was so nervous at first, but to be honest after how amazing everyone was during that lingerie shoot I kind of forgot about how weird and wrong this shoot actually was you know? I mean this all shouldn’t have made it out of my room let alone on camera, I…” Ash started ranting, his insecurity after the fact returning full force, but Jessy was quick to silence him with a finger to his lips.
“Did you like the shoot, did you have fun?” Jessy asked interrupting him. Asking a straightforward and simple question.
“Yes, I did, I loved it, it felt so good, hell I felt better and more confident than ever, but…” Ash started, as soon as he sad but however Jessy cut him off once more.
“But did you hurt someone?” She asked keeping a straight face as she saw Ash’s confusion.
“No, of course not, how the hell would that hurt someone?!” Ash exclaimed confused and some annoyed at the insinuation that he might have hurt someone.
“Well if you had fun, felt better than ever and didn’t hurt a soul, then please enlighten me about what was so wrong about what you did and why it should remain hidden from everyone?” Jessy asked him.
Ash’s annoyance went back to confusion then to realisation as Jessy’s previous questions suddenly made sense. Still he tried coming up with a way in which it was wrong, but when he took to long Jessy took the word once more. “It shouldn’t remain hidden from anyone because you didn’t do anything wrong. If you felt better than ever then letting that side of you out, showing it to the world is the right thing to do and don’t let anyone ever tell you otherwise, most importantly don’t tell yourself otherwise.” Jessy exclaimed.
It made sense what Jessy said, and still Ash couldn’t shake that nagging feeling that it was wrong. Jessy realised full well what was happening. Coming out, changing your life up so drastically after years of keeping it secret down to some pretty extreme lengths with the black-market hormones wasn’t a process of a day. Doubts, being scared, it was all completely normal but she couldn’t let Ash spiral down to thinking it was wrong. No today they had made a very important step forward to Ash’s self-acceptance and she wasn’t going to let it get ruined by negative thoughts. He would get there someday after building enough confidence. She was sure of it.
Wanting to distract him from thinking to much on it, Jessy asked her question again. “So what outfit did you like modelling most?”
“Uhm, well that’s hard to say actually. I liked them all a lot actually. I guess if I had to pick one it would be the bikini though. It has always been my dream to model in some kind of sexy surf swimwear shoot so it was definitely a dream come true and an experience that was hard to top.” Ash said.
“Well I can tell you one thing. You looked really spectacular in that bikini. There’s no doubt in my mind that the pictures from that setting will be fitting for pretty much any magazine cover.” Jessy agreed, helping boost his confidence back up as they entered the house and the changing room once more.
“Let me help you get off those breast and hip forms as well as your makeup. I know you might want to keep them on, but trust me, after wearing them all day your skin will thank you for being able to breath again. We wouldn’t want you to develop a rash now would we?” Jessy asked playfully as she helped Ash out of his towel and bikini top, going to work with the glue solvent and the makeup remover.
It was somewhat weird and in a way it also was a bit concerning to see the ‘breasts’ he had had all day suddenly fall of his chest bringing him further back down to reality. “You can take them home with you, and when you want you can always give me a call to put them back on for you.” Jessy said, a little concerned, knowing full well what the impact can be of seeing yourself get stripped from that perfect body again.
After removing the hip pads and makeup Jessy said. “I believe you can do the rest yourself in the bathroom. Here are the clothes you wore here, oh and about the nails and the hair let’s just act as if I didn’t notice those shall we? It looks really good on you.” She complimented with a playful wink helping him deal with the going back to normal.
Ash couldn’t help himself from embracing Jessy in yet another tight hug. She was so sweet to him and even now after watching his breasts disappear she refuelled his confidence. “Thank you so much Jessy, you are the best.” He exclaimed before taking the clothes he had arrived in. The ones Keira had selected for him to humiliate him, but after how everyone had just seen him he wasn’t too bothered to put them back on.
While Ash was in the shower Beatrice went about seeing that everyone was paid correctly. She did pull Dean to the side though. “Hey Dean, I know it isn’t really usual when I ask for you work, but could I get all unfiltered and non-altered pics on top of the finished collage? It would mean a lot to me.” Normally she wouldn’t really care about the non-filtered pics, but these would make a nice memory, a memory of the kind of daughter she had always dreamt off.
There were times at which she could have sworn that all of it seemed very natural to Ash, too natural for this to be new to him even. There were times she thought he was having a little too much fun for this to be really forced for him, but the fact remained that Ash had been pressured into this shoot. She couldn’t be sure whether or not he wanted this and she was afraid that straight up asking him would put him on the defensive. That Jessy girl and him seemed to get along fine. Maybe she could ask her, or ask Ash some subtle questions in the hope it would clear things up.
Besides Beatrice couldn’t risk Ash crashing and potentially doubling down on the denial. Not only would it be a real pity to see him lose his self-confidence and potentially miss the chance at telling her about how he felt if her suspicions were right. It would also risk her plan of pitching Ash as the substitute model getting ruined. No whatever Beatrice did she had to be careful and let this come from Ash himself.
As Beatrice rounded out payments and bid everyone farewell Ash moved out of the bathroom. His very long wet hair was wrapped into a towel and he was back to wearing the dress and lingerie his sister had selected for him. Even though he had to do it without breast or hip enhancements it still looked pretty good on him even if he did say so himself. Moving back into the dressing room he was instantly met by Jessy who gave him a quick wolf whistle, further boosting his confidence. “Look at our natural beauty.” She exclaimed, letting Ash know that he didn’t use those silicone forms or makeup to look good.
“Now remember what I said about those black-market hormones. You really have to stop taking those. I wouldn’t want to see you ruin yourself like that. If you want to use hormones and you are serious about it, my offer to take you to that doctor still stands. If you need me for anything else don’t hesitate to call me at all.” Jessy once again urged, she really wanted to let it get through to Ash just how important that it was that he stopped those hormones which could have dangerous consequences as their exact composition was unknown.
“I won’t Jessy, I promise.” He once again said as Jessy pulled him into yet another quick hug, just as his mother arrived in the dressing room to check on them. Realising his mother was there, looking at him in this dress Ash couldn’t help but blush a little. Like Jessy had said though, there was nothing wrong about this even if it was hard to express that in front of his mother.
“Jessy, thank you so much again for your service and if we ever need you again in the future I’ll make sure to call you. Now it’s getting late and I think it’s pretty much time for all of us to go home.” Beatrice said as she paid Jessy and she and Ash said their goodbyes. She then remained quiet as she walked to the car with Ash, not wanting to jinx anything. In fact it just once again amazed her how natural Ash moved in his dress and heels.
(If you like my story and would like to see more and support me please consider joining me on Patreon: https://www.patreon.com/Fibaro . If you don’t want to or can’t then don’t worry, everything will eventually be available for free, but it’ll take a bit longer to become available.)
Chapter 6
The drive home ended up being rather awkward for both Ash and his mother. Ash was still coming down from the high of having an absolutely amazing time at the shoot. Yet now in the car with his mother all doubts and nerves were hitting him full force again. Jessy’s pep talk had given him a boost, but it wasn’t helping much in this very moment. Did his mother suspect he liked it? What must she be thinking of him if she did? Her only son a sissy? Ash was no sissy, but in the moment those derogatory terms Keira had used instantly jumped to mind.
Beatrice wasn’t feeling any more at ease herself. It had been wonderful to see Ash blossom during the shoot. It was like finding that long lost daughter she had always wanted and she thought she saw the signs that Ash was a little bit to natural for this to be his first time. That he enjoyed it a little too much for this all to be just a punishment. She didn’t know for sure if that was the case though or if she just saw things she secretly hoped to see.
It would be fun to have a daughter she could go to the salon with? A daughter as keen on shopping as she was, the kind of daughter she had never had with Keira. She was scared of bringing it up out of fear of ruining everything though.
Eventually Beatrice was the first to speak up however. She simply felt like she had to say something, that she had to break the awkward silence. “So Ashley, I think you’ve proven beyond a doubt that you do make a prettier girl than Keira. Of course we’ll still need that portfolio to convince her. You know how your sister is a sore loser. That she won’t admit defeat until she has no more choice.” Beatrice said, realising to late that she had called her son Ashley again. He just looked so pretty in his dress. It was to late to correct that slip up now though. It would only make things more awkward if she did.
Ash hadn’t failed to notice his mother’s slip up either. It made him blush. He kind of liked that name despite it being one Keira had forced on him and had forced others to call him just to spite him. Yet the way in which his mother used it so naturally, calling him by a girl’s name gave him hope.
“Uhm thanks mom. I guess Jessy did a really good job teaching me how to walk in those heels and on the makeup and you know that other stuff.” Ash said somewhat embarrassed, trying to cover up his slipups of being too natural this way.
His mother having known him his whole life instantly noticed his embarrassment. Had that natural walk in heels really been because of Jessy? No way. She had noticed it at home as well, before they even met Jessy so that couldn’t be it or was she really seeing ghosts?
“No need to thank me sweetie, you did great and you looked great. A makeup artist can only enhance beauty, they can’t create it. You were prettier than Keira and more elegant at that. Trust me I’ve seen enough people walk in heels and despite all of them knowing how to, not all including your sister can manage them with such natural elegance.” Beatrice said.
Seeing the look of sudden panic cross her son’s face after being called out for being a little too natural she quickly corrected herself. Was she wrong? Did she push this too far? “Anyways, I guess Jessy was a very good teacher then. Being able to teach you in such a short notice while also doing such an amazing job on everything.” Beatrice added.
This time Ash didn’t stop blushing, he could swear his mother knew or suspected. Had he been that obvious? He had really enjoyed himself, so he guessed it had been obvious. If it had been that obvious then his mother seemed very chill with it which was good he guessed. It kind of filled him with hope yet at the same time with a certain fear of the unknown. Maybe he was just imagining things.
“Well I did try my best to look good for the camera, you know since Keira insisted on taking it to a shoot and everything I wanted to own it and show her I could win.” Ash said trying to explain his behaviour while also secretly admitting that he had tried and it hadn’t all been Jessy’s teaching, that he was in fact more natural than he wanted to let on.
“You really did own that bet, hell you owned that shoot like a full-fledged model and I’m proud of you. You did just as good as most of my models and with a little guidance you could really make it to the top. I bet I could even get you on the cover of Vogue.” Beatrice ranted before forcing herself to shut up, now she was really getting carried away.
“I do think I have enough of betting for now, but thanks for the offer. I do admit it was fun, owning that bet I mean.” Ash smiled with his ever-present blush. Slowly but surely he was relaxing a little more and slowly but surely he let go of his reservations.
“Hahaha well if you’re ever up for another bet and want to have some fun owning it I will gladly bet you some contracts. You know so you actually win something substantial from your bet.” Beatrice joked a little although she was really serious about getting Ash all the contracts he wanted if he’d let her.
“Hmmm, I might have to take you up on that someday. I guess it could be fun. Like I said though, for now I’ve got enough of betting for a while.” Ash replied, their conversation just having grown a lot more serious and open under the guise of joking around. Both of them where joking yet they were kind of serious at the same time, touching on that topic that had caused this whole awkward silence at the start.
“Just say the word and I’ll write up a bet with your name on it. Don’t wait too long though. I mean I wouldn’t want you to forget everything Jessy taught you today nor my instructions. You were doing so great on your own by the time our shoot ended.” Beatrice joked back.
“I’ll try my best to remember that mom, thanks.” Ash said quite happy. It was starting to get clear to him that his mother was actually quite okay with this all. It was a huge weight that fell off his shoulders. Maybe he might even discuss that doctors visit Jessy suggested, well maybe sometime in the future. He still feared how she would react when she found out he wanted to take this all the way. It was a way bigger step than just some crossdressing.
Now Beatrice ended up feeling a little bad. Clearly this was about more than just that bet and Ash had jokingly confirmed her earlier suspicions. She felt bad for never seeing it before and about the fact that she had planned to use this brother and sister quarrel for her own gain. Maybe if she could get Ash to accept her offer without slightly forcing the matter though she could redeem herself.
“So Ashley, let’s say I found myself in a bind and could use the help of a natural born model I’m sure would fill the role perfectly. Could I then make you a bet?” Beatrice asked expectantly. It was stupid to still keep up this whole supposed betting thing instead of just saying what she needed to say and ask him for help with that contract and the model that had fallen out.
“Uhm yeah sure I guess if you really needed a bet like that. I mean if you really need my help I would help out.” Ash said suddenly a little more awkward again. Was his mother asking him for a contract? This was suddenly becoming all too real and he didn’t know whether or not he was ready for it. To be entirely honest it frightened him a little. Shooting this portfolio no one would ever see was something completely different than doing a real honest modelling contract.
“I don’t know whether or not you picked up what that phone conversation you and your sister interrupted was about, but just in case you didn’t it was about one of my models who had an accident. She fell on her face and it needs healing that while she was supposed to shoot for a big contract at the start of next week. A contract to become the face of an advertising campaign for a hair and skin care company. That same company you borrowed that sample from your sisters room from.” Beatrice started her explanation.
“Now of course they weren’t happy to have a fall out on such short notice, and they won’t be happy about that social media reveal that’s now delayed as well, but of course if I could offer them a model I know will do just as well and even better as a replacement they would be eternally grateful and continue putting trust in my agency. It could mean a big growth. So I was thinking, could I bet you to fall in and take that contract. Of course they’d have to agree, but I have a feeling they most certainly would.” Beatrice finished in a hopeful tone.
“Well uhm, I guess so. I mean that’s one hell of a bet, could I think about it I mean not to long of course with this urgency, but it’s a lot to take in right now. Especially after today. I mean I don’t know if I’m qualified.” Ash stammered overwhelmed by the offer. It brought his feelings of insecurity right back. No way he would be accepted over something like this. Sure he looked good from afar, but far from good, or did he. He simply didn’t know anymore.
Beatrice couldn’t believe her luck, if she hadn’t been driving right now she would have hugged Ash tightly, but at the same time she understood his hesitance and didn’t want to overwhelm him even further. Instead she went with a compassionate understanding approach.
“Of course honey, tell you what, why don’t you think it over tonight and tomorrow we could discuss things further over lunch. I know this great place at the mall their food is simply to die for, and while we’re there we could maybe even find you something more professional for an eventual business meeting I mean if you were to agree that is. We should also find you something more casual to wear in between shoots. I mean dressing up is fun, but if you need to dress up all day it can be exhausting. Especially when the outfits aren’t always that comfortable. Sometimes a comfortable legging and a loose top can be a blessing.” Beatrice exclaimed.
Ash couldn’t believe what he was hearing. He had been so worried about what his mother would think of him and in such short notice he had basically been offered a modelling contract and to be taken out shopping by his mother. Hell he hadn’t even fully admitted that this was actually a dream come true for him. They had just been joking around a little, but now things had turned very seriously.
“That could be fun.” Was all Ash said, too overwhelmed to really think of saying more. Feeling that she might have been a little too enthusiastic Beatrice decided to just shut up and let it sink in for a while. She could imagine how this was all way too much to take in after such a day out of his comfort zone. They were nearly home, a quite evening in could do wonders, in any case it would offer Ash time to give everything a place.
Her only real worry was that Keira would instantly be on his case. She couldn’t really stop her daughter from dropping things completely from now on. Keira was way to sly to really stop her, but she could see to it that she left Ash alone tonight at least.
Pulling up into the garage Beatrice noticed how Ash looked a lot more nervous than before again. She wasn’t wrong as Ash was in fact way more nervous. Home was where Keira was and he was pretty certain she would be on the war path by now. Her whole precious plan of revenge had failed and Ash knew her well enough to realise she would need to recuperate that time two fold.
Getting out of the car Ash mainly stayed behind his mother, Keira listened to her and respected her so with his mother rooting for him he would be somewhat safe. Keira was lounging on the couch in the living room, watching television as they entered. Nearly instantly she jumped up giving Ash a venomous glare.
“Ash, could you go to your room for a minute? Take a shower, relax do what you want, but could you please go somewhere else for a minute, me and your sister need to talk.” Beatrice said calmly yet in a cold tone, a whole lot different than the tone of the conversation they just had. Ash knew better than to protest, in fact he didn’t want to be a part of this whole discussion. He was glad to move upstairs.
While Ash went to his room, sighing a breath of relief after his very busy scary day that had luckily and against all expectations turned out rather great. Keira and Beatrice were having a very heated discussion downstairs. Keira’s main vocabulary revolved around the words sissy, pansy and faggot. She couldn’t believe Ash got away so easily, with so much support, hell he had looked like he loved it. He had no idea how hard it was being a female model and putting up with all that shit. All she wanted was to bring her brother in discredit, to make him pay and to turn their mothers opinion.
Beatrice was firm and very clear however. She insisted Keira should never use any of those words ever again as they were plain unacceptable. When Keira tried to sway her opinion by exclaiming how he had been dressing in secret, probably for ages she had to swallow once. It hurt that she hadn’t known or seen it as a mother, but she remained firm in her point that if that was so they should support his choice.
The discussion ended with Keira angrily storming off to her room, even more pissed than she had been earlier. Her retreat went hand in hand with a warning from her mother not to give Ash any grief and to leave him alone. Beatrice sighed deeply rubbing her temples as Keira slammed the door of her room shut. She just hoped her threat would hold, at least for a while. She knew how vindictive Keira could be.
Going to the fridge Beatrice grabbed herself a glass of wine and decided to just relax for the evening. Today had been one hell of a day. She was supportive of Ash, but she would be lying if she said it didn’t take a lot out of her. Beatrice was all out of energy for today, as wonderful as it had been seeing Ash blossom it had still been a lot to take in. Especially her inability to really bring it up or discuss it properly out of fear of making Ash shut down was nerve-racking.
While Beatrice relaxed on the couch Ash was up in his room. He had stripped down to his lingerie and was just staring up at the ceiling, wondering what all of this meant. He had felt, great, he had felt anxious, understood, worried, he had pretty much felt it all today and he had no idea what that meant, how would things go from here on out?
In the end Ash just came to the conclusion that it was best to just wait and see. He didn’t know exactly what his mother had in mind for his lunch tomorrow and while he was slightly worried he also looked forward to it. Feeling happy but above all else confused Ash eventually drifted off to sleep.
Keira on the other hand was in no way ready to go to sleep yet. All she could think off was how to get her revenge on her brother. If she couldn’t discredit Ash towards their mother then she would just have to find another way to make him pay. A special shoot with that perv of a photographer could be great. So would setting up a date with her own boyfriend it would fix two problems at once.
Their mother might be supportive of him, and he might not be as scared of her finding out as he was before. Yet Keira was certain she could still blackmail him by threatening to tell his friends and girlfriend. If she got her hands on the pictures of that shoot then she would certainly be able to make Ash do her bidding. All she now needed was an unguarded moment to confront him, a moment where their mother wouldn’t be able to save him. Plotting out a way to get to Ash and get the revenge she had hoped for today Keira eventually fell asleep as well.
Chapter 7
It was still early in the morning when Ash was woken up by a light gentle knock on his door. “Ash it’s me, I was wondering if we are still on for lunch today? I know it’s still early, but well I was wondering whether or not you’d want to get ready so we can get going already? We could grab a breakfast as well I mean. We could make a day out of it instead of just lunch.” Beatrice said a little awkward, maybe this was too much, she didn’t know, what she did know was that she couldn’t wait to go out with the kind of daughter she had always wanted. That and she really wanted to get to know Ash or Ashely better. She couldn’t believe she had never seen this in her son before and she needed to rectify that.
Having only just woken up Ash was a little caught off guard. His first thought was to panic over his mother knocking on his door while he was sleeping in lingerie. That panic quickly faded however as he thought back to yesterday and the talk he had had with his mother, she probably wouldn’t be mad if she saw him like this, hell she had seen him like this during the shoot.
Ash was quite surprised however that his mother already wanted to go out this early, but he was not about to object. It would take him away from Keira for one, and he was excited to see what the day would bring, going out to the mall with his mother certainly seemed like fun and like he had concluded yesterday he would just wait and see how this whole thing evolved. He was still a little worried, but cautiously positive.
“Uhm yeah, mom, I’ll be down in ten minutes.” Ash said as he got out of bed. With a slightly blush he stripped out of his lingerie, it still felt somewhat awkward, to wear lingerie and interact with other instead of alone in his room while no one was watching. Out of his lingerie he put on a pair of boxer shorts, socks a pair of his jeans and a t-shirt. It was pretty much his regular get up. Dressed like this he headed downstairs to greet his mother.
As he arrived downstairs his mother was waiting on him, dressed to impress like always, wearing an expensive purple designer dress she had modelled for herself, along with sheer black pantyhose and a pair of matching purple pumps. Instantly she gave him a once over, looking quite surprised as she did so.
Beatrice didn’t know what she had been expecting really, but it wasn’t for Ash to come down dressed like always, it looked so out of tune with his long extensions which had held their wave pretty well and the one inch French tipped nails applied to his fingers. It was just weird, his lack of breasts, the clothes it looked just like her son like she was used to seeing him, but the long hair framing his face and his nails were decisively girly.
It was a weird combination and Beatrice couldn’t help herself but make a remark on it. “Honey, I don’t mean to be a bother to you, but shouldn’t you put on something else?” She asked as gently as she could manage, not wanting to have Ash shut down on her. She had been expecting him to dress a bit more well girly.
“Or maybe we could take care of those nails and that hair. I understand if you feel uncomfortable heading out as well as Ashely I guess. All I want is for you to be comfortable, and you can of course wear whatever you want, but I think you’ll attract more attention dressed like this with your hair and nails than you would otherwise. Of course if this is what makes you feel best then we can definitely head out like this. I mean what I am trying to say is that you can dress however you want, I don’t want you to feel obliged or anything at all. It’s your choice.” Beatrice rambled some what awkwardly. She realised that she might have sounded judgemental that she might have put pressure on Ash he really didn’t need right now. This was just all so new to her and she really didn’t know how to deal with it all.
Ash blushed, he hadn’t even thought about putting on anything else, going out to the mall with his mother just standardly made him put on his regular clothes. His mother was right though, this was probably how he would attract most attention. He kind of wanted to go out as Ashely, to have a girl’s day out with his mother, but on the other hand he was very nervous as well, maybe getting rid of his beautiful extensions and nails was better.
Still it nearly physically hurt to think about his pretty hair and nails going, that after barely a day. He couldn’t really bring himself to ask his mother to help him get rid of it. He kind of wanted to go as a girl, but he didn’t really dare to, neither did he want his nails or hair to disappear, but one thing was for certain, he couldn’t go out like this. It was a dilemma he tried to solve by making an excuse.
“I uhm, I don’t have any clothes that could be seen as casual enough to go out. I mean that dress Keira forced me to wear yesterday is all I have. Maybe I should just get rid of that hair and those nails then.” He said as an excuse as to why he’d need to go as a guy. It would be painful to see his hair and nails go, but he really had no other option right?
“Oh, if that’s your problem I can definitely help, I do have some things from when I was younger something more fitting for your age and more casual I mean. The outfits might be somewhat outdated, but I am sure we can put something together. Let’s go have a look.” Beatrice said overly excited as she started heading up the stairs to the master bedroom. She had always dreamed of sharing clothes with her daughter, something Keira wasn’t at all open to and so this was like another dream come true for her.
Not knowing how to react Ash followed along. He was scared to go out in public dressed as a girl, but at the same time he was also rather excited. He wanted to dress up for their trip, he just didn’t dare to. Where he had thought that his argument would be the end of this his mother had surprised him. Really surprised him, she had seemed to take it very well, but he would have never imagined she took it this well, to the point of helping him get dressed up for their trip.
As Ash made it into the room a little behind his mother Beatrice was already in full form, collecting clothes from some where in the back of her closet. By the time she turned back around she was carrying an arm load of clothes which she threw on the bed and started arranging in outfit combinations she had often worn when she was young.
Instantly a bright blush appeared on Ash’s face, not only because he was nervous about this whole heading out as a girl becoming very real all of a sudden. He blushed looking over some of the outfits his mother had worn when she was younger. There were some really slutty things between those outfits. Things he didn’t want to imagine his mother wearing.
“I know it’s all a little outdated, but I’m sure we’ll find something you’re comfortable with. You know these things are actually making a return nowadays, you can call yourself the proud owner of some vintage clothes.” Beatrice laughed to lighten the mood a little.
“Now does your eye catch anything right of the bat or should I make some suggestions? You can try some things on to see what they look like on you if you want.” Beatrice exclaimed enthusiastically, but that enthusiasm soon turned to worry as she saw Ash just stare it with a blush. Was she being a little too much again? She really needed to start controlling her impulses.
“Look sweetie I’m sorry for overwhelming you, take your time and if you change you’re mind then that’s totally fine as well, no hard feeling. I just think this might look cute on you. It’ll show off your assets perfectly.” Beatrice suggested holding out a pair of Jeans which looked like they would be kind of tight around the ass, yet wide around the legs. It went with a white long sleeved crop top. It was cute, yet very similar to what Ash was already wearing making her guess it would be closest to his comfort zone.
While it was in fact something Ash would easily and comfortably wear, there was so much choice, so many cute outfits, way cuter than this one. In fact this outfit was one of the lamest of the bunch. Ash had worn pants pretty much all his life and his mother had pulled out some cute skirts. While he was nervous about heading out as a girl the skirts simply looked way too tempting not to at least try on.
“What about this outfit here?” Ash asked shyly as he picked up a tight fitting long sleeved white turtle neck top and a checkered black and white high waisted skirt. “I mean I guess with a pair of tights and my white sneakers it would make a great outfit since I doubt you have shoes in my size.” Ash said tempering his own excitement over picking on of the girlier yet concealing options. He didn’t want to dress in the slutier outfits after all.
Beatrice’s face instantly cleared up as she walked back to her closet and pulled out an unopened pair of black tights. Her suggestion had mainly been out of concern for how comfortable Ash would feel but this was so much better. Way better than she had hoped. She already knew that this outfit would look absolutely stunning on Ash.
Ash blushed a little, what had he gotten himself into? This outfit was very good indeed, but it was oh so girly, then again his mother had seen him in way more revealing things than this yesterday at the shoot, the only difference was that it was his choice now. Slightly hesitant Ash stripped down to his boxers and he was about to open the package of tights when his mother stopped him.
“Oh no, you can’t wear such a pretty outfit with a pair of boxers, here let me help you out.” Beatrice said returning to her closet and coming back with a white satin bra and panty set with subtle lace detailing. The set looked rather innocent, full cut and apart from the fabric and small cheeky details rather normal.
“Here this will be much better, I haven’t worn this set yet and you can have just tell me when you’re done changing?” Beatrice said with a smile as she turned around. Ash blushed, getting dressed in his mothers undies, she couldn’t know it but for him it was all to familiar, a huge throwback to when he had started exploring this side of him. Tucking his penis back he quickly changed into the bra and panty set, the slippery satin feeling amazing. Carrying on dressing he put on the tights, then the skirt and finally the turtle neck top.
“If you need any help with that bra clip just let me know.” Beatrice said as Ash was taking a little long. Yet she didn’t push him in the slightest. Ash waited until he was completely dressed to tell her he was ready though.
Turning around Beatrice’s jaw nearly dropped, seeing her son with his new hair and nail dressed in one of her old outfits their resemblance was eery. Ash looked pretty much like a twin of hers when she had had that age. The only thing slightly ruining the overall look was the fact that the bra looked a little weird under the tight top without anything filling it. “Wow Ashley, you look absolutely spectacular. You don’t mind me calling you that do you? It’s just so much more suiting. Just wow.” His mother exclaimed absolutely stunned.
Blushing Ash had to admit she was right, his naturally soft features, his bright blue eyes and the long wavy hair combined with this outfit really made him look fantastic at least as far as he was able to tell from the image reflected in the mirror nearby. The only thing he was lacking was some filling for that bra. “I guess you’re right, Ashely does sound more fitting. Do you think I should put those breast forms back on?” Ash asked before blushing as he realised what he had just asked. He had been thinking aloud more than anything else.
“If you’re comfortable with it I think that might actually really complete the look, that and maybe a touch of light makeup, but only if you want that is. “ Beatrice said easing Ash’s nerves again. She was so glad that Ash had made the same observation and she was also glad that he was starting to open up a little.
“Okay, I be right back down in a few minutes.” Ash said as he walked back to his room, taking the form Jessy had given along from their box and slipping them into his bra. They might not look as seamless without the glue and makeup, but the bra held them well enough and under the top no one would be able to tell anyways. Brushing out his hair quickly, adding some volume Ash went to work on his makeup, a natural look, just smoothening out his natural features a little, enhancing his eye lashes and giving his lips a subtle touch. He was shock at how much like a real girl he looked and it made him so excited. It even helped his confidence. He was rather certain that while he would get a lot of stares none of them would be because he looked weird. He looked hot even if he said so himself.
When he moved back down Beatrice’s jaw dropped once more. Even without all the professional help it was spectacular how easily Ash passed as a real girl and a looker at that. As he put on his white sneakers the outfit looked instantly casual. A pair of shoes could do so much for an outfit after all, with heels this outfit would be instant chique.
“You really do look amazing Ashley, just wow.” His mother repeated once more, slight disbelieve in her tone as they walked to the car. Time and time again she couldn’t help but feel amazed at just how gorgeous of a girl Ash made. It was a pity that she had never noticed it before, but at least she knew now.
Wasting no more time they got in the car and pulled out on the street, another flare of nerves hit Ash. Now that they had left the safety of the house this had suddenly become way more real. It was strange how his feeling towards this situation changed constantly, but then again this was a huge step.
This would be his very first time going out as a girl. It was so much different than dressing at home with his mother, or even at that shoot which had been a relatively private gathering. At the Mall literally everyone could see him and it was scary. He might feel sure about passing, but that inkling of doubt remained. He didn’t like it, he wanted to get rid of it, but it was stronger than himself.
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Chapter 8
For the first few minutes of the drive Ashley remained relatively quiet as she stared out of the window, pretty nervous about being seen and recognised despite how good she looked. After Jessy’s pep talk she realised it was all just in her head and that she should be proud of who she was. That she shouldn’t fear people getting to know the real her, but it was a task that was easier said than done.
Beatrice who saw how Ashley looked around nervously tried to lighten the mood a little by asking some questions, trying to engage Ashley in some small talk to distract her mind. “So how are you feeling Ashley? Are there any particular stores you want to go to? Did you have a favourite place to eat in mind?” were some of the questions Beatrice asked, all answered very shortly by Ashley who kept looking out of the window somewhat nervously. What had she gotten herself into? Was going to the mall like this really a good idea?
Once they left the neighbourhood Ashley managed to relax a little more. Out here the change was less likely that she would be seen by anyone she knew, at least while they were in the car. It was then she realised that she might have been a little too short with her mother and she felt bad for it. So far her mother had really been amazing, accepting, encouraging even and she was so grateful that she had dealt with Keira yesterday.
“Mom, I’m sorry for being so short, I guess I am just a little nervous. Also I still want to thank you for yesterday, for being so supportive and for dealing with Keira for me. You’re the best and I’m really looking forward to our day together despite it being a little scary.” Ashley softly said explaining herself to her mother, it was the least she could do after her mother had done so much for her.
“It’s okay sweetie, I understand. Well I mean I can’t imagine how hard this must all be for you, but I understand how you’d be nervous. Just know that I think you’re very brave and as far as your sister is concerned you are more than welcome. That girl should control her temper better and be more supportive of you. I’m also looking forward to this day a lot.” Beatrice said as she drove on, her concern exchanged for a big smile. Ashley’s words were heart-warming to her a clear indication that she hadn’t been too overbearing.
“Thanks again mom, as to what kind of shops I would like to do I have no idea. Why don’t you just show me some shops you think have a good style? I mean you’re always so well dressed.” Ashley said. She did have a few ideas, but although her mother was so supportive she still felt a little apprehensive showing just how much she knew about being a girl. Besides the thought of learning about new places was also rather exciting. Her mother did have a great style after all.
“Sounds great sweetie. We can just window shop a little and see where they have a nice collection. Lunch is still a while away and even after lunch we still have all afternoon if you want.” Beatrice excitedly explained. This was going to be so great she thought as she pulled up into the parking lot.
As Beatrice parked she noticed how nervous her son or now her daughter was looking. She couldn’t imagine how hard it must be for her to get out between all these people in the mall, but she was determined not to go back home like Ashley probably wanted now from the looks of it. She was certain she would blossom once she got into the flow of it, just like she had at the shoot the day before.
“We’re here sweetie, what do you say about stopping at this nice coffee place first? A girl can’t shop on an empty stomach right? I bet you’re going to love the place, their coffee is amazing and their croissants are to die for. You simply have to try one.” Beatrice exclaimed with a big bright smile as she got out of the car. Setting a clear first goal might help to get Ashley to open up more. She kind of wanted to push her a little bit because she knew she would enjoy their day, it remained somewhat tricky though. She was afraid of pushing too much.
Walking around to the other side of the car Beatrice opened Ashley’s door. “Are you coming sweetie?” She asked as nice as she possibly could, trying to act as completely normal to put Ashley at ease.
Ashley looked around the parking lot rather nervously. It was still pretty early, and there were lots of cars already. The outfit that had seemed like a dream choice back home now felt awfully exposing, maybe she had better chosen something more androgynous. In any case it was too late to go back now. She couldn’t disappoint her mother who was being so sweet, or at least that’s what she told herself. It was easier for her to convince herself not to disappoint her mother than it was for her to convince herself that it would all be okay. She shouldn’t do this for anyone but herself and she shouldn’t care about what others might think, but that was easier said than done.
Taking a deep breath Ashley eventually got out of the car, surprised as her mother nearly instantly hooked her arm into hers before walking off not leaving much room for hesitation and second guesses. “Let’s go Ashley, our coffees are waiting for us.” Beatrice said as she headed straight for the entrance. While Ashley felt the overpowering urge to hide she was glad her mother took charge like this, otherwise they probably wouldn’t get very far at all.
Since she wasn’t about to ask her mother to go back there was no other option than to at least try and look confident. It was probably for the best as trying to hide behind her mother would only lead to more suspicion. The saying fake it till you make it did hold merit after all. Straightening her back and raising her head Ashley tried her best to look confident like all the girls her age she looked up to. A change Beatrice noticed which she could only applaud.
Keeping this confident walk up was getting harder as the drew nearer to the entrance and there started to be more people around them, but Ashley forced herself to keep it up. Much to her surprise no one really paid her the kind of attention she was fearing. Most of the real looks she got were from guys and not looks that told her they thought she was a freak, but actually looks that told her they were checking her out.
It made her feel strange but good as well, being checked out and admired by these guys, some of them being rather cute. Although she wouldn’t want anything to do with them as they were checking her out while being here with their girlfriends. She had always kind of admired the male physique, not as something she wanted, but rather as something she wanted to be with. It was yet another one of her secrets. She might have a girlfriend herself, but just like her workouts that was more of a cover up than true love.
Surely she liked the girl a lot and they got along great, but not in a way she felt like a boyfriend should love his girlfriend. She didn’t manage to summon those same intense butterflies in her stomach as when a handsome guy checked her out. In all honesty she was kind of ashamed that she had used Kelly, his girlfriend as a cover up.
Their arrival at the coffee bar her mother had been talking about brought enough distraction to go back to the present. They took place at a table near the edge so there was a good view of the people strolling by through the mall’s hall. A girl about Ashley’s age soon arrived to take their order, just like everyone so far she didn’t look surprised or suspicious upon seeing Ashley. She just looked at them as any mother and daughter out for the day. “Good morning, what can I get you girls.” She pleasantly asked.
“We’ll both have a latte macchiato and one of your famous croissants please.” Beatrice ordered for the both of them as the girl politely nodded her head before going off to get their order. Ashley just looked over the crowd of people passing by kind of amazed about how well everything had gone so far.
“So Ashley, how are you feeling so far? As far as I can tell you’ve got nothing but looks of admiration so far. No one thinks strangely of you not even the girl who took or order saw anything but a gorgeous young woman. What I’m trying to say Ashley is that you need to worry a less, just have fun, oh and enjoy breakfast, sorry that I took the liberty of ordering both our breakfasts, but it’s just the best order you can put in at this place you simply have to try it.” Beatrice said trying to get Ashley to relax.
It felt good to hear it from her mother as well, confirmation that she hadn’t been imagining things at all, most people really didn’t seem to car about who she was and how she was dressed, and those that did care to look twice mainly did so in a positive way. “It’s strange mom, I don’t know whether to be relieved or shocked, but things really have been going a lot better than I thought they would have so far for which I’m really grateful.” Ashley said visibly more relaxed than in the car already, despite the fact that they were now in plain view of everyone.
“I might have to hold your arm a little tighter though if I see the way most of these guys look at you. Wouldn’t want you to run off and leave me shopping alone now would I?” Beatrice teased a little with a slight giggle and a wink, the fact that a lot of guys had checked Ashley out hadn’t slipped her observation either.
“Mom!” Ashley exclaimed in a half annoyed mock angry tone before bursting into giggles herself. A light blush spread across her face as it was a bit embarrassing to have such things pointed out by her mother, but if she was honest, she kind of loved the playful teasing. It just felt right for some reason as the both of them shared in the laughter, only interrupted when the girl came back to serve their breakfast.
Taking a bite of the croissant Ashley had to give it to her mother. “This thing is really great, mom, I’m glad you took me here.” She commented enjoying her breakfast already feeling a lot more confident. The more people passed by the more relaxed she started to grow. It was constant reassurance that she fit in rather well which was great.
Beatrice herself was very pleased with how everything had turned out so far. Their day had gone off to a way better start than she had expected. It just felt strangely natural in a way, pleasantly so, then again Ashley looked rather natural as well and she was starting to blossom yet again which was all she could really hope for.
“No Ashley, it’s me who’s glad that you wanted to join me. I’ve always loved shopping and it’s so nice to have a daughter who enjoys it as well.” Beatrice said rather genuinely. Keira had never liked shopping, dragging her along had always been a chore. This really was very nice and refreshing.
It touched Ashley, the way her mother had so genuinely called her by a girl’s name and most importantly how she had called her a daughter. She was so glad she had taken this risk and she was so grateful to her mother for slightly pushing her where she hesitated for a moment.
Breakfast passed by with some small talk as Ashely grew more and more comfortable being at the mall. Eventually they finished their breakfast and it was time to get some real shopping going. The first shop they passed, one that offered sport gear instantly grabbed Beatrice’s interest. “Ah here we are, trust me if I say that you are going to love stores like these if you decide to pursue a modelling career and otherwise if I might add. Workout clothes might not be the prettiest things out there, although I’d say some pieces can be gorgeous. They are definitely the most comfortable clothes out there. Perfect to relax at home or to change into after a shoot. Besides as a model you would need to work out regularly as well.”
“No arguments here, I’m sure a pair of leggings and a sports bra is nicer than whatever you’d encounter in the male section.” Ashley said, a slight nervous tremor in her voice. She was starting to feel more relaxed being around people, but this was the first store they’d do and you couldn’t buy something you hadn’t tried on right? It was exactly that trying on part that worried her. Her breast forms weren’t really attached so she doubted she could really pull off a sports bra for all to see. Her mother didn’t look at all worried though and with how supportive she had been already the least she earned was Ashley’s trust towards this.
Knowing Ashley would probably be nervous Beatrice had come well prepared. She had contacted the stylist from the shoot to get all of Ashley’s exact measurements so they wouldn’t need to search endlessly and so Ashley could avoid the potentially embarrassing process of getting her measurements taken.
As they roamed the store Beatrice left Ashley as much freedom as she could, only suggesting a few outfits herself while letting Ashley pick out every outfit she wanted to try on. By the time they headed to the changing rooms they both carried an arm load of leggings, sports bras, tank tops and sweaters. All in bright colours or with a special design to them, a big difference with the rather dull male workout clothes she had always owned and which all looked the same.
“If you’ve changed into an outfit please just give me a call so I can check it out. I’d love to see how they look on you, I’ll join you in the changing room unless you want to step out of course.” Beatrice offered leaving the choice completely to Ashley, to leave it up to her whether she was confident enough to step out or not.
Just like Ashely had feared the sports bras were a little too tricky to head out in leaving too much cleavage bare and making the detached breast forms way too obvious. She was really grateful to her mother to leave her the opportunity to remain in the safety of the changing room. She did want to show off her outfits and she did want to get a second opinion, but she could bring herself to head out in something that showed cleavage due to the circumstances.
Trying everything on ended up taking quite a while, but it was a blast Ashley was loving the chance to try on so many different outfits in such rapid succession, checking how they looked on her. Like wise Beatrice was loving the opportunity to give her honest opinion on everything, good and bad, pointing out how certain special stylistics didn’t look as nice as they thought they had or how certain thing looked simply perfect on Ashley. She was enjoying herself so much that she even honestly forgot Ashley was anything but her daughter which in turn helped some of her own awkwardness or reservations towards treating Ashley, trying her best not to offend her. Their interactions grew a lot more natural, their bond flourishing just like Ashley’s confidence was.
In the end Ashley had tried on at least two dozen different workout outfits that would work well for all seasons. From those she had selected six different ones to buy. While she didn’t feel comfortable being seen in just a sports bra Beatrice still insisted on buying the matching ones of each outfit. “Think of it like this sweetie, if you workout at our home gym no one will notice, besides even under one of the tank tops you will still need something to support your breasts.” Beatrice said cryptic enough so no one at the store could figure out she meant the breast forms while still allowing Ashley to understand what she meant.
Her mother was right of course, and she couldn’t really pass the opportunity to ger full matching outfits either. She was looking forward to working out now more than ever. While all of her outfits would be nice, her favourites were definitely the summer ones. The short spandex shorts would look simply amazing paired with knee high compression socks and she really did like showing off her legs and butt. Ashley was aware she had a nice pair of legs and a nice bottom. Unlike the breasts they weren’t fake either and since no one had called her out on being a guy yet her confidence had grown to the point where she actually like the idea of showing off her assets a little.
“Thank you so much for the new clothes mom.” Ashley exclaimed, sounding genuinely excited and happy as they left the store, being in public for some time now and their first real store they had done as mother and daughter had really broken the ice. Ashley was getting increasingly comfortable just being out and about and it showed in her enthusiasm. She no longer held back out of fear and worry.
“It’s my pleasure sweetie, I mean it. Our trip has been such fun already. Oh why don’t we go there next? A girl can never have too many pairs of shoes now can she?” Beatrice said as she spotted a shoe store across the hall.
“I don’t know mom, maybe it is better to shop some outfits first so we can pick up shoes to go with them later.” Ashley commented, not that she wasn’t excited about shoe shopping, she just wouldn’t know what to look for just yet.
Beatrice was slightly taken aback by the comment. It did most certainly make sense though, she just hadn’t thought about this. “You’re absolutely right sweetie, silly me. I just forgot you don’t have a wardrobe full of cute outfits just yet. Of course we need to shop outfits before shopping shoes, you’re most definitely right. Lucky me to have you along.” Beatrice laughed as they went deeper into the mall’s halls in search of a clothing store that caught Ashley’s eye.
Once they found one the same process as in the workout store followed, only this time Ashley seemed more vocal and confident voicing which clothes she wanted and which she didn’t want. One thing that really stood out about he choices was how she only seemed to go for skirts and dresses of all sorts. The only pants she selected were some cute shorts. Ashely had worn pants for way too long and now that the cat was finally out of the bag she didn’t want to return to wearing pants. At least not when she got to be Ashley. Sure girls jeans were cuter than the ones for guys, but the came nowhere near close to beating dresses.
Just like with the workout clothes the same trend emerged in Ashley’s choice of outfits each top and dress was a little conservative when it came to showing cleavage, but the skirts were on the more provocative side showing plenty of leg and, just like the shorts which were all tight enough to further enhance Ashley’s bottom. While these could be cold in winter a pair of thick tights and boots could easily fix that.
In the clothing store Ashley’s reservations towards showing off her outfits outside of her own cubicle also changed. None of the clothes she tried on were treated privately. In fact she was proud to show off all the outfits they had selected out in the store where everyone could see her. While her mother carried on with her honest opinions Ashley’s pride and enthusiasm while showing off the outfits radiated to the point where other women shopping there felt inclined to help provide feedback while they were in line for a stall of their own or were waiting for a friend to emerge from her stall.
It was a huge boost to Ashley’s confidence. No one treated her any differently, she really felt like one of the girls here, hell she was even eager for second opinions besides her mother’s and profusely thanked the women who chipped in with their own feedback. Being accepted in such a manner really allowed Ashley to blossom and show her true colours. Just like during the shoot her confidence only increased as time went on.
By the time they had gone through every outfit they had selected just short of two dozen outfits which would provide plenty of combinations when mixed and matched. “Thank you so much for my new clothes mom, you are the absolute best!” Ashley said with a quick peck on her mother’s cheek as they checked out. They each had two full arm loads of shopping bags to carry.
“You’re very welcome sweetie, it was my pleasure. Heavens would you look at the time, I guess we better head to the car to relieve ourselves of these bags. Time has flown by which isn’t that surprising when having so much fun. We can grab a quick lunch after freeing up our arms as we’ll definitely need more arms if we still need to hit up that shoe store.” Beatrice laughed, absolutely radiant herself as Ashley quickly agreed.
Today had been a day Beatrice wouldn’t soon forget. The kind of day she had always dreamed of having with her daughter, little did she know she had always had a daughter who loved shopping for cute clothes just as much as she did. Shopping with Ashley had been an absolute delight.
Especially in that last store Beatrice had been so proud. There were a few other mothers shopping there with their daughters and all had complimented her on what an absolute delight her daughter Ashley was, so radiant she simply put a smile on everyone’s face. As nice as that had been to hear it had also shown Beatrice some of her shortcomings. As the other mothers shared stories about their daughters she couldn’t really join in. She had only know Ashley for about a day and a half so far something she desperately wanted to rectify. She definitely hoped she would get to spend more time with her new found daughter.
The joyous mother daughter pair with their arms loaded with shopping bags quickly made their way through the mall’s halls. Eagerly chatting and laughing as they made notes about all the windows they passed from the stores they still wanted to visit on their way to the car. “It looks like we’ll need a quick lunch mom if we want to stop at all of those stores.” Ashley jokingly said.
“That or we’ll have to come back another day.” Beatrice eagerly retorted.
“Hmm, why not both?” Came Ashley’s reply as they both laughed loudly among themselves attracting quite a bit of attention, but neither of them really cared. While they were joking around Beatrice couldn’t help but notice Ashley paying some more attention to the guys eye her up than before. After how Ashley had softly scolded her for pointing out guys during breakfast she didn’t bring it up again though. She felt as if her new daughter would tell her when she felt ready.
After a quick stop at the car to lighten the burden of all their bags Ashley and Beatrice made their way to the food court where they both ordered a simple shrimp salad, a light, but delicious lunch. It was finally time for Beatrice to breach the subject that they had initially came here to discuss. It was kind of strange how an initial lunch to potentially discuss a modelling deal had turned into such a long nice mother daughter day. Beatrice didn’t mind at all. The potential contract was only an after thought by now, Beatrice now cared more about getting to know her daughter better.
“So Ashley, you remember what I brought up yesterday? Potentially launching your modelling career? Before you say anything, I want you to know that you can choose whatever makes you feel best. This is in no way shape or form mandatory and I won’t love or accept you any less if you don’t feel comfortable with it. I just think you could make an amazing model and if you were willing to try I would love to give you all the support to succeed that I possibly can.” Beatrice said realising that she might have pushed Keira a little too hard on that front, trying to make her something she wasn’t or didn’t want to be. She was a hard business woman, but there were things that mattered more in life her kids being one of those things. She was not going to make the same mistake twice.
“Uhm well I don’t know mom, I don’t think I would make a very good model, or that any company would even want me to model for them. Tell you what though, if you would be able to find me a contract, if that company you brought up wants me I’m definitely willing to try.” Ashley said a little insecure. She did want to be a model, but she was lacking the self-confidence. As much as she had enjoyed herself today, as much as it had allowed her to really feel like a girl, she wasn’t quite confident that she would pass in front of a close up camera.
“That’s a deal Ashley so let me get this straight, I have your permission to be your agent and actively look for contracts. If I find a contract you will happily give it your all to execute it to the best of your capabilities? Most importantly YOU want this? I don’t want you saying you are willing to try because you think that is what I want to hear Ashley, I won’t look for any contracts unless that it what you really want.” Beatrice said, cautious that Ashley wasn’t doing this for the wrong reasons. It was wonderful to see how she had blossomed being a girl out in public and she didn’t want to ruin this by putting pressure on her.
“I really want you to look for contracts mom, I would be happy to model, I just fear that I won’t be any good at it and that no one will want me.” Ashley said firmly with a light blush. She couldn’t believe she had just confessed this to her mom, but in a sense it felt good as well.
“You will do great, I just know it, you have your mother’s talent after all, that much was clear during your trial shoot. We should be able to put together one of the best portfolio’s I ever had to work with, with the results that shoot yielded. You better clear up your agenda cause everyone will want to work with you.” Beatrice only half joked, she mainly wanted to grow Ashley’s self-confidence as that seemed to be what held her back the most. She hoped that in time and with a few success’s Ashley could just start seeing that she had nothing to worry about and have fun with her shoots, just like she had started to have fun with their shopping trip.
“Well mom, as my agent it would be your job to make sure I’m not over worked. I mean if I’m actually going to be as good as you claim you wouldn’t want me to burn out.” Ashley said with a wink, returning the joke. She doubted that her mother was right, but then again she had doubted if going out dressed like a girl was a good idea as well and that had turned out absolutely amazing.
Finishing up their lunch the mother daughter duo continued on their shopping spree, trying literally every store that had caught their interest. There was only a slight break in their afternoon when they needed to make another trip to the car to unload their bags and when they went for a slight refreshment.
They roamed the mall right until closing time. There had been only one awkward moment all afternoon and it was when they hit up the lingerie store. Ashley loved lingerie, but wearing something sexy, nearly naked, especially with how the breasts weren’t properly attached and blended like Jessy had accomplished yesterday was just awkward. Not wanting to push Ashely, Beatrice had respected her wish to stay alone in the dressing room. She had thought about arguing that she had seen her in lingerie during the shoot, but the last thing she wanted was to push her.
By the time they left the mall, Ashley had an outfit for pretty much every situation, a full girly wardrobe which had cost a small fortune to buy all at once, but it was so worth it. It helped a little with Beatrice’s feelings of guilt over never having seen the signs. Besides, with how comfortable Ashley had gotten through out the day she was quite certain that it was a worthy investment, Ashley would surely get a lot of use out of her new wardrobe now that she felt comfortable that she could pull it off in public.
As both women eagerly chatted away on their way home they forgot all about Keira and how they had basically snuck out of the house this morning not to have to deal with Keira. They had had so much fun all day that this morning seemed ages ago.
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Chapter 9
When they arrived both Ashley and her mother were all giggles. It took them multiple trips to bring all of Ashley’s new clothes up to her bedroom by which time the floor was literally littered with. They were so consumed by the fun atmosphere that remained after their shopping trip that they didn’t even think about Keira.
Of course it helped that Keira was nowhere to be seen. The moment she had heard the garage open she had rushed up to her room and locked herself in. If yesterday had proven anything it was that her mother was completely on Ash’s side, hell she and her brother had even embraced the name Ashley she had tried to taunt him with. If she wanted to get back at who she still considered her brother she would have to catch him alone so her mother wouldn’t interfere.
All Keira’s plans to humiliated her brother and get back at him for being the torn in her side, had back fired completely. That would all change soon though, or so she hoped at least. Her day home alone had been spent plotting to get back at her brother in ever growing frustration. If Ash liked being a girl so much she would show him. He didn’t even know half how lucky he was getting to live his best life without having to be that girly model her mother and boyfriend pressured her too be.
She should have dumped Bruce’s ass long ago, and while she could have done so she would have had to put up with way too much bullshit because of it. She didn’t want to ruin her mother’s business by destroying the bond with the biggest investor they had. Let’s see how much her brother would like being a girl if he had to put up with her demanding asshole of a boyfriend. Bruce would certainly fall for it as she knew he cheated on her with more feminine girls. She didn’t mind as all those girls did for him she wouldn’t have to do anymore. Ashley was pretty and girly enough for Bruce to fall for her, that much was certain. Keira thought with a devilish smile as she had already sent a few pictures of Ashley to him, telling him her cousin was in town.
Her brother had a girlfriend so clearly he was straight. Having to go on a date with her boyfriend would most definitely teach him a valuable lesson of how lucky he was to be a guy, it would certainly humiliate the living shit out of him and Bruce alike. Oh he would be so mad when she would reveal he had kissed and dated her brother, surely he would want that news to stay under wrap so she’d have something against him as well. She just hoped that Ash was still scared enough of her to be forced into the date.
While Keira was awaiting the moment to spring her devious trap Ashley and Beatrice were going through the time consuming task of reorganising Ashley’s closet. After spending all of yesterday modelling outfits and today dressed in an old outfit of her mother, shopping for more girly clothes it was a bit awkward to see her closet filled with all guy’s clothes. Her guy’s clothes seemed more like a bad memory after these two long exciting days.
Still it grounded Ashley back in reality as well. No matter how she looked at it she was still a guy, she had friends, a girlfriend and they only knew her as a guy. These last two days had been a dream once she had gotten over the awkward bit, but now the doubts that had plagued her returned. She didn’t know if she was ready to show Ashley to all her friends and her girlfriend yet.
No matter how much Ashley wanted to never end this day, to keep on living her life as nothing but Ashley and throw out all of her old clothes she still decided to keep about a dozen of her favourite outfits from when feeling more comfortable as a girl had been her biggest best kept secret. These dozen guy outfits were pushed to a far corner of her closet while the rest got filled with her new purchases and some of her mother’s old clothes.
It was a dream come true as she opened her closet now, being greeted by colourful clothes, dresses, skirts, lingerie instead of her dull boring guy’s clothes. Those were rather hidden from view now, a lot like his small girly stash had been hidden before. Ashley couldn’t wait to try on all of the new outfits she had bought today, but right now it was bedtime. Having spent their day at the mall until the last possible moment and this big reorganisation of her closet it was getting very late. “Thank you so much for the amazing day mom, I loved it. I’m spent though and I can really use a good night’s rest.” Ashley giggled as she gave her mother a tight hug and a kiss.
“You’re very welcome sweetie, goodnight! Just so you know tomorrow I will probably be out for most of the day, I’ll go to that big client to discuss you replacing our injured model and make some visits to present your portfolio to some other clients I just know will love working with you. Goodnight!” Beatrice beamed before leaving the room with a smile, she had had an amazing day herself, but she too was tired.
Ashley felt great as she was alone now, taking a moment to admire today’s look in the mirror. She looked amazing even if she did say so herself and now that the cat was out of the bag she had the freedom to be her real self a lot more often. Right now when her mother had told her about her work for tomorrow she was excited rather than nervous. The more she thought about it, the more she warmed up to the idea of doing some actual modelling. She was really starting to hope that her mother would succeed.
Feeling on top of the world Ashley decided to take a relaxing bath before going to bed, with all this shopping she had worked up a sweat and she didn’t want to soil her brand new satin sheets straight from the start. At least that’s what she argued, all she was really looking for was a reason to test out all her new bathing products. It was silly really, these were her products now and she shouldn’t have to justify using them. She should just take a bath because she wanted to and so she did.
Pampering herself had been great, after her long fun, but exhausting day. Her bath had left her feeling very refreshed and relaxed, surrounded by all the wonderful smells of the products she had picked from her body wash’s to her lotions. Selecting one of her new pyjama’s, a pair of short baggy blue satin shorts with a blue lace trim and a matching spaghetti strap top, Ashley crawled into bed, she loved the feeling of satin all over her body, and the fact that she was now wearing her very own cute pyjama’s, no more borrowed or stolen stuff, this was all hers. Thinking back on the events of today and yesterday Ashley slowly drifted off into a peaceful wonderful sleep.
Chapter 10
Since her mother would be out all day and she had nowhere to go or to be Ashley hadn’t bothered setting an alarm. Besides these past two days might have been amazing, but the constant battle with her insecurities had also taken their toll, nothing a good long night’s sleep couldn’t help though. Keira had other plans though she had set her alarm very early, not wanting to be surprised by Ash being gone before she could get to him again.
It was still early morning, Keira had patiently waited for her mother to be gone from the house so she’d have free reign. It was clear her mother wasn’t on her side, but she was determined to make Ash pay, so far her revenge on him had backfired so she needed to step up her game big time, oh she was quite positive that he would never come back from what she had come up with.
Barging into his room, not even trying to Keira shouted. “Good morning sissy, rise and shine as you, my pathetic excuse for a brother have a date and you are nowhere near ready yet.” She loved the way her brother nearly fell out of bed, completely startled by her loud obnoxious entrance, just like she had hoped shocking him was just so much fun.
“K…keira, what the hell, what are you doing? Could you please leave my room right now? I’m trying to sleep and I’m done taking shit from you.” Ashley said, slightly bolstered in confidence from the shoot and the shopping trip, yet faced with her mean vindictive sister she couldn’t help but feel a little nervous as well. Shocked out of her sleep and still a little groggy, Keira’s words hardly registered, but when they did Ashley’s face turned to shock, a date? What was that supposed to mean?
“That’s where you are wrong sissy brother of mine, you might think you are done with me, but I am no where near done with you yet. You might have mom on your side, but news flash, mom isn’t here and she won’t be for a very long while, at least most of the day if all her previous contract negotiation are something to go off meaning you are stuck here with me.” Keira announced with a big shit eating grin.
“Now I can be wrong, but does your girlfriend now you’ve always wanted to get into her panties literally rather than as a figure of speech? Or your friend do they know you’ve been more interested in their cute butts and big bulges rather than in their friendship?” Keira asked trying her very hardest to play on all of her brother’s insecurities, his fear of coming out was still her largest bargaining chip and judging from how pale he was suddenly getting she knew she hit the jackpot. This was bound to get him a little more pliable to her demands.
“T…that’s not true, I don’t care for my friends in such a way and I am going to tell Kelly eventually that I feel more comfortable as a girl.” Ashley stammered scared to death, it was true what she said and yet she could already imagine the devastation on Kelly’s face and the disgust and hurtful words his friends would have plenty of for him.
A fear Keira expertly kept playing into. “Yeah, like they’re going to believe that? I don’t even care if your gay or not, what do you think your friends would say if they saw you in your cute pyjama’s? What would Kelly think if I told her you came to me asking if I didn’t know a cute gay guy from one of my modelling job cause you were in desperate need of cock and she simply didn’t cut it for you? If I showed her your shoot and new wardrobe who do you think she would believe no matter what you say?” Keira asked menacingly, going in for the final blow. The look of shocked horror followed by defeat on her brother’s face told her all she needed to know.
“I thought so, now I promise to keep quiet so long as you do exactly what I say, mom will never have to find out about this, you tell her, I’ll tell your friends and girlfriend, it’s that simple. Anyways, we’ve wasted more than enough time, it’s time for action now. Like I said you have a date to go on, a lunch date to be more exact. Now follow along, I readied a bath for you.” Keira said as she held the door open for Ashley like a mock gentleman.
Ashley felt more like a mouse backed in a corner by a cat than anything else though as she got out of bed with her head slumped in defeat. She didn’t want to play her sister’s games, but she could let her ruin thing with everyone she had ever cared about like that. With what she had just said Ashley was convinced that she could and would do just that, she had no choice here, she just hoped that it would be the last of Keira’s shit she had to put up with and although she would never admit it, somewhere deep down she also hoped it was a handsome guy she was set up with.
The bath Keira had drawn for her filled the room with a strong flowery smell. The smell of the products she had bought yesterday. She didn’t really mind taking a bath, hell she would have probably taken a bath anyways, and she had selected these products herself so she didn’t really mind that either. The only thing she didn’t like was that it was a bath with the intention of getting ready for a date Keira had set up for her. It distracted from the relaxation a bath was supposed to be. At least Keira hadn’t entered the bathroom with her, she had just locked the door and told her she had 30 minutes.
In the end the warm water and amazing smell managed to sooth some of her worries, but they came back full force when Keira opened the door. She didn’t look inside, just put her hand trough the doorway and threw some stuff on the floor. “Time’s up sissy, it’s time for you to get that ass out of the tub and get dressed. I’ll be waiting with the rest of your stuff in your bedroom.” She said commandingly as Ashley got out of the bath with a loud groan.
Drying herself off Ashley first lotioned up her body then went over to have a look at what her sister dropped in for her to wear. Much to her surprise it wasn’t nearly as bad as she thought it would have been. A simple pair of white lace bikini styled panties with a matching bra, her breast forms and a pair of glossy nude pantyhose. It was rather modest as far as lingerie went that while she had expected her sister to pick out the most outrageously sexy set she could find. Not that she minded as she put on the lingerie, tucked away her cock and put the breast forms into her bra before returning to her room.
“Alright little brother, time to put on your dress. Put your hair into a nice ponytail and put on some subtle makeup, now chop chop.” Keira ordered as she stood to the side with a big grin spread across her face. On Ashley’s bed there was a simple baby blue summer dress with a white lace Peter Pan collar and a skater skirt next to a pair of white leather pumps.
They didn’t have the tallest of heels and the skirt only came a few inches short of reaching her knees. It wasn’t exactly prudish by any means, but not too revealing either. Paired up with her sister’s instructions for her makeup, some soft pink lipstick, lip gloss, a little bit of eyeliner, mascara and some foundation, but nothing more. That and her hair tied off with a baby blue ribbon left for her, she ended up looking modest, dressed up nicely for sure, a little cuter and more playful than just casual, but nothing too much. It actually was an outfit she was rather comfortable being seen in, even for a date.
Then again all the clothes she had bought yesterday were clothes she wouldn’t mind being seen in after seeing how well she had been able to pass. It was just that some of the sets especially with some sexier lingerie were definitely racier. Paired with heavy makeup she could definitely be made to look like a complete slut, giving any guy she would be set up with the wrong idea. Surprisingly enough her sister hadn’t opted for that which was very strange given how she had made her dress up for the shoot.
Although she was suspicious of her sisters intentions Ashley wasn’t about to complain. After all if she had to go out with a guy she really preferred to be dressed somewhat modestly. The last thing she wanted now was for her sister to change her mind on her outfit.
“You look very pretty little brother of mine, very pretty indeed. I have to give it to you, you did win the bet, you can make a prettier girl than me, but that’s only because I’m not trying, I don’t want to look like some prissy sissy girl.” Keira spoke, her tone betraying that she was still salty about having lost the bet. Under any other circumstance Ashley would have put up a triumphant smile, but not now, now she was too nervous for the upcoming date Keira had fixed for her.
“I do have to warn you though bro, when guys see a pretty girl their blood usually rushes to places other than their brains which leaves just enough blood for them to think about the fastest way into your panties. Guys are animals like that, but I don’t expect you to know, you aren’t a real guy after all. You’re probably more interested in the clothes than the actual girl although I guess that means you are thinking about getting into their panties, only literally instead of figuratively.” Keira mocked her brother loving how his blush was dark enough to shine through the light foundation. He should feel at least as embarrassed as he had made her feel during the shoot.
“On their quest to get into your panties guys can get very pushy, or aggressive even. I wonder what one of those guys would do if they found out you’re not really a girl. I don’t think those guys take the fact that they are tricked lightly. “ Keira continued fuelling Ashley’s fear for her upcoming date. She didn’t want to go anywhere with a guy, especially not the date Keira had arranged for her, but what if the guy would force himself on her like Keira claimed could happen? The thought made her shudder. If she ended up in the hospital because of this, their mother would be royally pissed and Keira screwed, but not as screwed as she would be.
“Luckily there are ways to prevent them from getting into your actual panties. You see if you give a guy a good blowjob and make him cum you can prevent him from going further. That is if the blowjob is good which is a big if. I could teach you how to give a good blowjob just in case you’d need it, but you’ll have to ask me. You need to ask me to teach you how to become a good cock sucker.” Keira said with a huge shit eating grin as she watched the shocked horror on Ashley’s face.
Ashley didn’t want to ask such a thing, let alone be taught such a thing by her sister, but despite that all she feared that it was in her best interest. If it really came down to it then sucking a cock was definitely preferable to potentially ending up in the hospital like Keira had made her fear. She was also kind of curious what sucking cock was like, but she would never admit it, and definitely not to Keira.
It was the fear that inevitably made her give in as she softly spoke up. “Keira, could you please teach me to become a good cocksucker?” The words instantly made her blush and shudder. While she was kind of curious asking it out loud was horrible, but she knew Keira enough to know she wouldn’t yield on that front.
A point that quickly got proven when Keira spoke up. “What was that sissy? I couldn’t hear you? I could swear it was something about helping you become an even bigger sissy, but I couldn’t tell for certain.” She had heard Ashley full well, but teasing her was way too much fun.
Knowing Keira wouldn’t drop the case under any circumstance Ashley groaned loudly before repeating herself in a raised voice. “Keira could you please teach me to become a good cocksucker?” She ask, still unable to ask it without shuddering. God this was embarrassing. Then again better some embarrassment now than real trouble later.
The fact that Keira stated laughing loudly wasn’t helping either. “Of course sissy, of course I’ll help you. I thought you would have been a pro by now. It’s better to start late than never though so lets get started shall we? I had a feeling you would ask me that, typical sissies, tell them they have a date and all they can think of is cock. In any case I put up a training corner, now follow me.” Keira taunted as Ashley momentarily thought about arguing that that was not true. In the end she decided to just keep her mouth shut and avoid the argument though. If thinking that made Keira happy then so be it. it wasn’t worth her energy and she knew it was not true.
With a deep sigh Ashely strutted behind her sister, following Keira to her room only to surprised upon entry by a life sized print of some kind of rugged naked blond haired jock with a rough stubble adorning his face, a muscular body and an ample amount of chest hair. What shocked her most of all however was the eight inch realistic looking suction cup dildo stuck to the crotch of the poster.
A huge smirk broke out across Keira’s face as she saw Ashley’s shocked look. “Tada, I wanted to make your experience as authentic as possible so here you go this is the best I could do without involving a real guy. After all we wouldn’t want a guy to get upset if you do a poor job and try to search your panties instead. Just for your info, this is what a real man looks like, not that you could know unless you got a little too antsy looking around in your gym classes.” Keira taunted.
“In any case let’s get started shall we? If you truly are new to this then we still have a lot to do before your date arrives. So walk up to your lover, pay him a compliment, something about his cock, guys love it when you compliment their cock. While you do that, sensually grab onto the base then get down on your knees before him.” She commanded as Ashley could only look shocked.
“Keira, you can’t be serious, this is going way to far.” Ashley complained as she looked at the poster with he cock attached then back to her sister. Her deep bright blush was shining through her makeup even. She had to admit that the guy Keira had selected on poster was a hunk, but this was too much.
“Oh is it Ashley, is this going to far for your poor sheltered sissy fantasy. I doubt that is going to work on a guy, but you can always try if this is making you too uncomfortable. You don’t have to do this you know, you asked for it, but if you want to try your luck without my help then sure don’t mind me. It’s not my ass on the line after all.” Keira said half irritated only further driving up Ashley’s fear to achieve her goal.
As much as she didn’t want to do it, she realised Keira was probably right, she could walk away now, but that wouldn’t be so easy with a pushy guy. Going through this training was sadly her best bet and while she would have preferred to practice on a cucumber or a banana. She knew like with all thing Keira wouldn’t compromise on this either. She might be the one forcing her to go on that date, but in order for the date not to become a complete disaster she sadly needed Keira’s help now.
Bracing herself Ashley walked up to the poster with a light shudder and exclaimed. “Your cock is big.” She awkwardly said as he blush deepened further. She couldn’t believe she was really doing this, but just like Keira had instructed she grabbed onto the base of the rubber cock. The fact that it felt shockingly lifelike and considerably bigger than her own cock had ever felt didn’t go unnoticed as she slowly sunk down to her knees.
“I’m going to stop you right there, do you even believe yourself with such a tone and word choice? I am certain you can do better, so try again, try so sound surprised, amazed and a little excited. Boys like to feel special so make your imaginary lover feel special.” Keira ordered while Ashley groaned in response. As if what she had just done wasn’t bad enough already.
She was fully aware that Keira wouldn’t go forth until she carried out this first step to her satisfaction so with a deep sigh Ashley got back up and approached the poster again. This time she tried to see it as an act with an audience she needed to convince to make it a littler easier. “Oh my god, it’s huge. I’ve never seen one this big.” Ashley gushed enthusiastically as she once again grabbed onto the base of the dildo and knelt down before it.
“Great, that’s a lot better, now pucker up those lips and give the head a kiss, take your time, make it long and sensual. Look up into the guy’s eyes and add a little moan. Make him believe it’s a pleasure to be allowed to worship that cock.” Keira ordered, loving how mortified Ashely was doing as she did just that. She might have her brother looking like the innocent girl next door, but she was definitely teaching him to suck cock like a slut.
“You can follow that up with a long lap, to catch that pearl of precum which is sure to have formed by now. Make sure to act like it’s delicious and never break eye contact. Once you did that you can kiss it again, but this time part your lips as you press them to the head of his cock, let them slowly roll over the head until its completely in your mouth then proceed to circle it with your tongue.” Keira instructed.
Ashley couldn’t believe her sister’s instructions, but she knew better than to defy them as she gave the rubber cock a lick. It tasted weird and plasticy, making her wonder what a real cock would taste like. She had to admit that she was somewhat curious. “Mmmmm” Ashley said as she licked her lips up at the poster, trying her best to put down a world class act, which was all it was, an act she once again tried to convince herself of just to make it all a little easier to deal with. It was still plenty of embarrassing, but as she slowly wrapped her lips around the head and started circling it with her tongue, it did take the worst edge off the shame.
“There you go, you’re a real natural, are you certain this is your first time sucking cock cause you are suspiciously good. In any case the next part will require some practice. You are going to deep throat that cock, go all the way down on it until your nose is pushing against the pubes on the poster and your chin to the balls on that dildo. Do it slowly and steady, then suck hard when you pull back to the head, but don’t pull off, just circle it with your tongue once and go back down.” Keira instructed, relishing how degrading it all was for Ashley.
Wanting this to end as soon as possible Ashley just went ahead and lowered her mouth on the shaft of the dildo, working it a little over half way down before being unable to continue. With it hitting the back of her throat taking it further down just seemed impossible. How could anyone do this? Ashley wondered as she was just about to pull back up, but that was without taking Keira into account. Without a warning what’s however she pushed down on the back of her head, forcing the about two inch dildo deeper down Ashley’s throat making her gag violently.
Keira Mercilessly kept Ashley’s head down on the dildo to the point where she feared she planned to choke her to death on it. Try as she might Ashley simply couldn’t push back against her sister, but then not a moment too soon Keira luckily released her head. “Not bad for a first try, now do it again, we won’t stop until you can take the whole thing.” Keira said not waiting for Ashley to act as she just once again force her head down, smirking with delight as her brother gagged.
Over the course of the next half an hour this cycle repeated time and time again. Keira kept hammering Ashley’s throat down on the dildo until she could push her nose against the poster. In time even the gagging was slowly going down, but it never quite disappeared. Eventually Keira even let Ashley take back control and she made full use of it by continuing to deepthroat afraid that Keira would take over again otherwise. Luckily she could manage to take it all with no help by now although it remained difficult.
This blowjob training was put to an abrupt end when Keira suddenly got a message ping. “That was your date sissy, he’ll be here in 15 minutes go freshen up your makeup and hair cause it’s really needed. Oh and remember, when a guy cums, pull all the way up so he can cum directly into your mouth, once you are certain that he’s done, pull off, show his load to him, then swallow. Remember all these things and you’ll be fine.” Keira explained.
She didn’t need to tell Ashely to go touch up her makeup twice. She was more than happy to get away from this awful training set up. Her head burned bright red as she noticed Keira hadn’t been kidding. The somewhat innocent subtle look she had applied now looked more suited for a ravaged whore. Shuddering lightly Ashley realised she had no time to waste with only fifteen minutes to her date’s arrival. In a hurry she cleaned up her face and started reapplying the makeup like it had been before.
( If you liked this story and would like to read way more along with a ton of other stories then please check out my page on SubscribeStar: https://subscribestar.adult/fibaro I have ran into trouble with Patreon, but since SubscribeStar doesn’t accept PayPall you can still follow me there, just make sure you connect your discord account to your Patreon account if you do so you don’t miss out on my content. https://www.patreon.com/Fibaro )
Chapter 11
Ashley was just brushing out her hair, the slightly sore throat being the only evidence that was left of her blow job training as she once again looked immaculate. When all of a sudden the door bell rang making her nerves reach an all time high. God she still couldn’t believe this was actually happening, that she was going on a date with an actual guy. Yet she was sure to meet him at any moment now. Hopefully he was at least handsome.
That wasn’t the biggest of her worries however. She worried more about the fact that this guy would actually believe she was a girl meaning that she could under no circumstance let anything on about the fact that she wasn’t really a girl, no matter how much she would like that. The thought of being found out was a terrifying one only enhanced by the fear that she could pass no where near well enough for this. Sure out shopping no one seemed to have noticed or cared much, but going on a date with a guy she would be inspected way closer, that and a guy would definitely care if he found out.
Within seconds Keira barged into her room throwing a small white leather purse Ashley’s way. “it’s time to go and greet your date. I’ve put everything you could possibly need in that purse so I guess that means your ready. If you need to touch up you makeup, there’s some lipstick and powder in there as well. Now let’s go!” She said not really waiting for a reaction as she just grabbed onto her brother’s elbow and dragged him along with her.
“Now remember this well, you are Ashley, you are my niece from upstate and you are just here to visit. If you just stick to that you’ll be more than fine, oh and if a guy goes on about sports or other things you know nothing about, just smile giggle and nod occasionally. You should always giggle whenever he tries to make a joke. Guys love that and it’ll distract from seeing you for who you really are.” Keira said on the way down.
There was no chance for Ashley to reply or verify anything with her sister as they soon arrived at the door which Keira quickly opened, forcing Ashley to drop into her role right away. A role she nearly instantly dropped out of as she instantly recognised the guy on the other side of the door as Bruce the asshole of a boyfriend her sister always complained about. This was so wrong on so many levels, she had been set up with her sisters boyfriend by her sister. Wasn’t that cheating?
“Wow someone doesn’t look happy to see me.” Bruce joked trying to break the ice as he noticed the shocked face of this pretty girl next to his girlfriend. Keira knew he cheated and seemed to be okay with it yet it had still come as a complete surprise to Bruce when she suggested he’d take her niece out for a date. Hell she had even gone as far as to say that if he managed to get her to blow him with a picture as evidence that he’d be allowed to take her ass like he had been nagging her about for forever. She stimulated and even rewarded his cheating and he was all too happy to agree.
He had feared that it would be one ugly girl, after all if Keira was so desperate to get her niece some fun then she had to be one hopeless cause. Still getting to take Keira’s ass in exchange for a blowjob he could just enjoy while he looked away from it would be so very worth it.
Much to his pleasant surprise however that wasn’t the case at all. If anything this girl looked like she was a real catch, she could definitely get a spot among the top five pretties girls he had cheated on Keira with. There was something innocent about her, but that only made her all the more desirable to him. It made him wonder why she wasn’t a model yet, having an aunt with an agency, and Ashley looked way better than Keira, way girlier as well in her heels, dress, hosiery and with her long hair. He was instantly looking forward to this date beyond the prospect of getting to take Keira’s ass.
“Bruce this is Ashley my niece, Ashley this is Bruce. Please forgive her for gawking like that, I’m sure she’s just shocked to see such a handsome guy. She’s a small town girl and she’s always complaining about how there isn’t a single cute guy living anywhere around her isn’t that right Ashley?” Keira casually said covering her brother on this first hurdle.
“Uhm, yeah…” Ashley spoke softly in the feminine voice she had often tried to practice, her cheeks were bright red being put on the spot like this.. She couldn’t believe this was really happening, and then she realised that Keira and Bruce never let on that they had a relationship. Given how she was being set up she could only conclude that Bruce thought she thought he was single. That was one messed up relationship he and her sister had Ashley thought, but she could do nothing about it now. Bruce would probably be as mad as any guy if he found out, and Keira was sure to ruin her life if she messed this up. She was trapped.
“Well in that case colour me flattered Ashley.” Bruce said as she made a deep bow before her, gently taking her hand and planting a kiss on top of it like some sort of gentle man in the movies. Uneasy, but admittedly slightly flattered as she saw Bruce obviously checking her out while he treated her like a lady. Ashley quickly let out a nervous giggle, hoping it was the right thing to do in this kind of situation. Keira just stood off to the side and smirked. Ashley was acting perfectly like the innocent girl next door she was dressed up as, this would show her being a girl wasn’t just fun and games.
“In any case let’s get going shall we? I’ve booked us a restaurant and afterwards we’ll have plenty of time for me to show you what the big city and if the mood is right I have to offer. I’m certain you are going to love it.” Bruce smoothly said, making his intentions clear from the start much to Ashley’s shock, this was shaping up to be a very awkward date, even more so than she had anticipated.
While Bruce was rather good looking, his body a little average in shape, but not muscular, at 6’1” quite tall, he had broad shoulders, short brown hair, brown eyes and a handsome face, Ashley did worry about the asshole his sister had made him out to be. Then again Keira was just as much of an asshole with how she had treated her, and seemingly she was okay and even encouraged Bruce’s cheating so she could hardly use that excuse. She guessed there was nothing wrong with cheating as long as they were both into it, but still if she was in a relationship she would prefer a monogamous one, which sadly wasn’t possible due to Keira. Ashley didn’t want to cheat on her girlfriend even though she knew their relationship wouldn’t last, but right now she had no option.
A quick shove from Keira alerted her to the fact that Bruce had held out his arm for her to take, a hint she hadn’t picked up on as she was too wrapped up in her thoughts. Blushing fiercely she put her daintily manicured hand in the crease of Bruce’s elbow as she joined him at his side. “Thank you Bruce I can’t wait to get to see the city, I’ve heard so much about it, but I’ve never really been out to these parts.” Ashley spoke softly, trying to get into her cover as the innocent small town girl.
She had the feeling that she was the only nervous one here Bruce seemed to be very eager and excited about this date while Keira wore a big grin herself as Bruce guided Ashley down to his car, slowing his pace so she could easily keep up with him in her heels. It’s one thing she had to give to him, he was a real gentle man, slowing his pace, opening her door, helping her in the car and closing the door for her. If the situation had been any different she would have loved to be treated like this, like a real lady, but the stress of having to keep up her cover while going out with her sister’s boyfriend made it hard to really feel at ease.
Bruce quickly got into the driver’s seat and took off as Keira waved them out. Just like that she was on her own. As bad as Keira had been she had proven to at least feel like some sort of support when it came to meeting Bruce, protecting her cover and making her see the hints she’s missed. Now that was gone as well. “So Ashley, what’s it like living in a small town? Doesn’t it get a little boring being around all the same people day in and day out, without any real big events to go to?” Bruce asked casually striking up some small talk as he felt Ashley’s nerves. Having seen Ashley he really wanted this date to work out for more than just getting to take Keira’s ass. He and Keira had an understanding, but he definitely wouldn’t call it a good relationship. They basically wanted opposite things, their relationship just happened to look good to the outside world. Ashley was a lot more his type if he was being honest.
If anything the small talk only made Ashley more nervous though as she had to imagine a whole new life for herself on the spot. “Uhm, it has it’s perks I guess, I mean knowing everyone can be a bit boring and it also sucks if you try to do anything no one should know about, but it’s also nice to really belong to a community I guess. If I’m honest I’m more interested in what you’re doing, what’s life in the city like?” Ashley said, trying to get Bruce to do the talking instead.
It caught Bruce completely off guard as he was used to showing a deep rooted interest in girls in order to charm them. It often worked way better than bragging about himself, but if Ashley insisted then he didn’t mind talking about himself. In fact it was rather nice to get to talk about himself for a change and Ashley seemed to hang on his lips which was nice. She attentively listened to everything he had to say, mixing in an occasional nod of acknowledgement, a giggle or a few words here and there.
The more he talked the more passionate Bruce became, he didn’t think he had ever connect with a girl as much as he connected with Ashley, at least not so straight of the bat. Ashley for her part managed to relax a little more. Just listening was so much easier than having to keep up her femme voice and keeping her story straight while constantly adding to it. besides, it was also rather nice to hear the passion in Bruce’s voice as he talked.
In what seemed like no time at all to the both of them they reached the restaurant, an upscale place that even had a star. It instantly made Ashley worry that she was way under dressed, but then again, with a pair of black jeans and a white polo shirt Bruce was dressed rather casually himself. If anything she looked more formal than him which at least eased her worries a little. Then it hit her, she had been so invested in Bruce’s talk that she had felt relaxed enough to worry more about the way she was dressed than about the remainder of her date. He didn’t seem like the worst guy making Ashley wonder why Keira made him out to be such an asshole.
Bruce carried on being a real gentleman throughout, quickly opening the car door for her, offering his arm to escort her inside, a very welcome gesture considering how uneven the ground was in some places. Without his arm walking through the gravel parking lot in her heels would have been a very tall task. As necessary as it was Ashley blushed fiercely nonetheless when she had to hold on tight to her sister’s boyfriend’s arm. Their conversation had been nice to the point where she nearly forgot about it, but now that realisation came back full force.
He on the other hand was more than happy, it was nice to have a girl really hanging on his arm for support, something that rarely happened with Keira given how she preferred sneakers over heels and even when he got her to wear heels they were always a pair made for comfort rather than to look pretty and sexy like the pumps Ashley wore.
When they got seated and handed a menu Ashley couldn’t help but gasp when she saw the prices of the food. “Oh my god, this place really is expensive isn’t it?” She had never eaten at such an upscale restaurant before as her mother only went to such places for business, business Keira as a model sometimes got invited on.
“It’s definitely one of the fancier restaurants in town, that’s for sure. I would feel bad if I wasn’t able to offer the best to one of the prettiest girls I’ve ever seen.” Bruce cockily replied with a wink, smirking as Ashley instantly buried her head in the menu, obviously very embarrassed. It was kind of cute, he had never dated such a shy country girl before, neither had he ever dated a girl he clicked with this well.
“Well uhm, thank you for the compliment. I can hardly imagine anything when reading all the items on the menu so I’ll be following your lead I guess.” Ashley shyly said after finally regaining her composure. It seemed to please Bruce to no end as he wore a cocky smile ordering for the both of them when the waiter arrived. His view on being the man might have been a bit outdated for his young age, but Ashley didn’t mind one bit. It made her feel like a princess not having to call any shots as she let ‘her man’ take care of her. It was this old-fashioned stance that what a relationship should be like that clashed heavily with Keira’s fight for independence and her loathing of just being a pretty thing though.
Like she had expected she didn’t recognise much of what she found on her plate when it arrived, the dishes looked more like pieces of art and were very tasty. Although she focused more on eating elegantly than she did on the food itself while also trying to carry on the conversation they had had in the car. It all took a lot of multitasking, but she managed quite well, quickly getting the hang of it as she once again managed to relax rather easily, forgetting all about how messed up this was.
As their lunch progressed Bruce was slowly getting more and more insistent about learning more about her making Ashley slightly nervous again. She had liked her time with him so far, but keeping up a lie, especially with potential dire consequences if she failed was hard and stressful to say the least.
Then an idea hit her, maybe she could talk without having to share much on the persona created for her and so she started talking about her dreams instead. “Living in a small town has its ups and downs, but it’s really boring really quickly, after all these years I’ve really had it there. I dream to one day make it big in the modelling world like Keira, to move here to the city and lead a more exciting life you know? My aunt has been great about it, she even helped me create a portfolio and is actually out seeing if she can get me a contract at the moment. I never thought my dream was realistic, but now it might very well happen.” Ashley spoke passionately and genuinely despite how awkward it was to call her mother aunt.
“That’s great news, if you come to live here we might even get to go on a second date some time. I would most definitely like to pull some strings to make that happen.” Bruce said slightly cocky as he winked yet behind his cockiness there was also a genuine excitement for Ashley which instantly got her to blush first then to worry. Shit if her dream really did come true then she would be stuck in the persona of Keira’s niece for forever and she was bound to make a slipup at some point. She had just doomed herself, but she couldn’t pull her words back, the best she could do now though was roll with it and hope for the best.
“In all seriousness though, why do you think your dream is so unrealistic? I mean if Keira can make it as a model so can you for sure, you are definitely prettier, and actually elegant. I’m sure you would be a joy to work with for any photographer, if I see the grace with which you carry yourself I would say you were a natural, camera and catwalk ready.” Bruce continued, gently stroking Ashley’s hand on the table as she turned all shades of red.
The compliments did sound genuine, but at the same time that made them all the harder to deal with. She couldn’t believe that’s really how Bruce thought and if she was honest she was quite flattered as well. If her mother and now Bruce told her she was a natural then there must be some truth to it right? God why was he getting to her head like that? How should she react, she was so overwhelmed that she would nearly certainly slip up or at least stumble over her words like a fool. She really needed to calm herself down.
So with that in mind she awkwardly pulled her hand back. She didn’t want it to stop, but she needed it to before she messed up. “Uhm if you’ll excuse me, I really need to go to the bathroom.” Ashley awkwardly explained, doing her best to keep her voice nice and feminine as she spoke before rushing off as fast as her heels could carry her without waiting for a reply.
Bruce was left behind a little confused did he say or do something wrong? He really thought they were starting to have a moment. Oh well girls would be girls he guessed. He doubted he would ever truly understand them.
Meanwhile Ashley approached the bathroom she nearly slipped up and went into the guy’s room, given how she looked and how she had pretty much everyone fooled that would be a disaster. Then again heading into the girl’s room felt awkward on it’s own. She might look the part, feel the part and want to be the part, but just like in the lingerie store she couldn’t help but feel like she was an intruder of some kind. She really had to think back to Jessy’s words about her worth to push through, at least the girl’s room had private stalls.
Being away from Bruce and the entire situation with him did help ease her nerves at least a little bit. I felt good to have nothing to really worry about for a while, giving her time to get her thoughts straight. Thoughts like why she was enjoying Bruce’s company so much, hell at times she even manged to forge that this was all set up by her sister instead of a genuine date. Bruce his interest in her and his lust towards her seemed rather genuine and if she was honest she was quite liking him as well. He really didn’t seem like much of an asshole aside from the fact that he cheated on Keira, but then again Keira was the one to set this up. He was a little cocky at most, but most of all quite handsome and a real gentleman. If he wasn’t in a relationship with her sister and if he knew she wasn’t a biological girl she could even see herself with Bruce as her boyfriend, but alas he could never find out so that just wouldn’t happen.
After calming herself down and taking care of business Ashley couldn’t help but notice how her lipstick had faded when she went to clean her hands. That simply wouldn’t do she thought as she reached into her purse to grab out a tube of lipstick for a refresher, only to be shocked when she saw a plethora of condom wrappers, lube and tampons alongside her phone, wallet and lipstick. It knocked the fear right back into her, remembering Keira’s words about how guys thought with their cock and only an orgasm would keep them at bay. She really hoped she wouldn’t need any of those things as it would mean her secret would be out and there was no way of telling what would happen then.
Giving her lips a quick touch up Ashley rapidly closed her purse back up, keeping the contents out of sight in the hope they would leave her mind soon after. They didn’t though and suddenly when she saw Bruce throw a big smile at her she became worried all over again. She tried not to show it though as she gave him a polite smile back.
The remainder of their lunch passed by pretty quickly after that, with Bruce paying for their food and leading a slightly nervous Ashley back to the car. He wondered what had gotten into her ever since she went to the toilet, had he really fucked up that bad? It had felt like they had such a good and relaxed connection up until that point only to then settle back into nervousness. Maybe a ride would ease her nerves he thought as he led Ashley back to the car and showed her all the hotspots in the city.
While Ashley knew the city it was still kind of nice to see it from a different perspective, to get Bruce’s input about it all. Yet she didn’t manage to relax fully again, instead she threw an occasional glance down at his crotch to check whether or not she was still safe from getting fucked and found out in the process. If she didn’t have to worry about her secret so much she had to admit that she wouldn’t really mind the prospect of sex. In all essence the date and Bruce had been surprisingly lovely, and she was kind of curious of what it would be like to be with a guy, just one who liked her for who she really was.
Bruce couldn’t help but notice the constant looks at his groin though. They made him think that Ashley might be so nervous because she wanted to ask to blow him. It would explain why she had touched up her lipstick and he would be lying if he said he didn’t want to find her lips wrapped around his cock. In fact it would be perfect. Keira had made a deal with him that if he could get Ashley to suck his cock and make a picture of it as proof that she’d allow him to finally take her ass like he had been asking for for a while now.
He had to admit that he had really been into it for the deal at first as he had no qualms about trying to get a girl to suck his cock. Yet when had seen Ashley and gotten to know her better that had all changed, she was probably the most lovely girl he had ever met and he didn’t want to ruin potentially getting to know her even better for a quick blowjob. If she wanted it though then he had no real qualms about it, it was a win win really. Just thinking about getting so intimate with Ashley made him rock hard.
It wasn’t something that didn’t escape Ashley’s attention either, instantly firing up her worries another notch. Oh god she really needed to do anything to avoid sex so she could maintain her secret was all she could think about as she kept glancing down at his crotch more frequently, willing the erection to go down. If anything it only got Bruce even more fired up and sure she wanted to suck his cock, but was nervous to make the step.
So in order to make things as comfortable as possible for Ashley, he drove off to a calmer lakeside just outside of the city. It was quite a beautiful place and the lake was huge so there wasn’t too much of an issue finding a quite spot where they wouldn’t be spotted. He really hoped that would take away some of the stress Ashley was feeling.
All Ashley could think about however was that Bruce took her here to fuck her. With her stress of being discovered growing to a climax she remembered her sister’s words of guys just needing to get their rocks of so before he could get too touchy she blurted out. “Can I suck your cock Bruce?” Her face instantly turned beet red as she clasped her hands in front of her mouth, not believing she had really just said that, but she needed to protect her secret at all costs.
Bruce for his part was completely taken aback by Ashley’s sudden aggressive request. He had thought he would have needed to ease her into this a little, to tell her it was okay, but the fact that she instantly asked for it the moment they had some privacy had to mean that he was right and her nervousness had stemmed from her dying to suck his cock. “Uhm, yeah sure you can.” Bruce stammered not as smooth as he would have liked.
It didn’t seem to matter much though as after a brief moment of hesitation Ashley went right to unbuttoning his pants. She feared that if she waited too long Bruce might get impatient and try to fuck her instead as she believed Keira when it came to guys. After all she was the more experience one by far and there were plenty of stories on the news as well. No she had to get this over with quickly and hope that Keira’s lesson’s had been good preparation.
As Ashley fished Bruce’s rock hard cock out of his pants she let out an involuntary gasp, it looked slightly bigger still than the dildo Keira had taught her to suck a little bigger than eight inches of cut, clean shave cock and it was scary to say the least. Yet despite the less than ideal situation Ashley also had to admit it was magnificent. She couldn’t believe she was really about to suck a guy off, which was kind of thrilling as well. She didn’t want Bruce to think that anything was wrong though so she covered her shock up with a compliment, after all guys loved that right? “Oh my god, it’s huge.”
The compliment was followed up by a lewd sloppy kiss right on top of Bruce’s swollen throbbing head. Just like Keira had said there would be, a drop of precum had formed at the tip of Bruce’s cock. While his cock smelled pretty much like his bodywash the precum did have a distinguished musky scent to it. It tasted kind of salty as well as she licked it off with a long lap like Keira had told her to do with the dildo.
Keira’s lessons sure seemed to work as it instantly got a loud moan out of Bruce, one that made her heart flutter in excitement. As much stress as it was to suck Bruce’s cock in order to keep her secret, it was also great to hear how he was enjoying it. It made her a little more confident that this would work, emboldening her efforts as she slowly rolled her lips around the swollen head, getting out a series of moans as she circled the sensitive gland a few times with her tongue, making it throb in her mouth, before she forced her head all the way down with her nose pressing into Bruce’s shaven pubes, before slowly coming back up. It was hard to take him all the way in her throat which was somewhat sore still from the aggressive practice with the dildo Keira had put her through, but at the same time it was also very rewarding as she earned herself a loud gasp from Bruce.
Only looking up in Bruce’s eyes was an impossible instruction to follow while giving head in the car, not that Bruce minded at all if his moans were anything to go off of. All Bruce could really do was marvel at just how good Ashley was at this, he couldn’t believe his luck, this was by far the most amazing and eager blowjob he had ever gotten. Ashley really seemed to be loving his cock where most others, Keira in particular saw it as more of a chore. He really couldn’t wrap his mind around how amazing this girl was. If she ever planned to move here then he was sure to try and take her more often, he would rather be with Ashley than with Keira. Nevertheless he did sneak a quick picture while Ashley was in full action before putting his phone away, feeling kind of like an asshole for doing it, but just in case Ashley was going to go away anyways he would have a reminder and a bit of extra fun out of this.
In the end Ashley didn’t need to bob up and down Bruce’s cock all that long as about five minutes in Bruce lost himself to the pleasure. “I… mmmm I’mmmm going to cummmm.” Bruce warned knowing how most girls hated when someone came in their mouth. Much to his surprise however, Ashley was eager till the end, pulling all the way up to his head, but not off his cock as she teased the head with her tongue until he sprayed her mouth full off cum. She just kept it there, taking each and every spurt, only pulling off when she was certain there was no more too follow.
When she did finally pull off she didn’t spit either, she just swallowed and said. “That was delicious, now if you wouldn’t mind, could you please take me home?” Ashley asked, nervous that he might be getting hard again and wouldn’t take just another blowjob. All in all despite the stress she couldn’t say she had really hated it, getting a guy to cum was pretty fun. The taste and texture weren’t great, but not too bad either, and Bruce’s cock looked great with lipstick rings all over it, still one time was more than scary enough.
“Uhm yeah, yeah sure, we’ll go home, that was amazing Ashley, wow.” Bruce replied somewhat stunned, still riding his post orgasmic high as he got his cock back in his pants and drove off while Ashley started retouching her lipstick, really not wanting her sister to know that she had actually had to suck a cock.
( If you liked this story and would like to read way more along with a ton of other stories then please check out my page on SubscribeStar: https://subscribestar.adult/fibaro I have ran into trouble with Patreon, but since SubscribeStar doesn’t accept PayPall you can still follow me there, just make sure you connect your discord account to your Patreon account if you do so you don’t miss out on my content. https://www.patreon.com/Fibaro )
Chapter 12
The ride home was pretty uneventful Ashley was too flustered and too embarrassed over what she had done to continue talking or asking questions about Bruce, and Bruce was still on cloud nine. It was the best blowjob he had ever gotten by far and all he could do was day dream about it as he drove Ashley home. He was too dreamy to really try and strike up a conversation. At least at first, but when throughout the trip he noticed Ashley’s slight embarrassment he really didn’t want to push it anymore, he figured the best thing to do was to give her some time.
Once home, her makeup back on fleek to remove all evidence of the blowjob she had given Bruce, Ashley got out being rather short with Bruce. “Thank you Bruce, it was a lovely date.” She simply stated, and it was, but right now she really just wanted to be alone. As great as it had been, the finish was more stress than actual fun, giving a blowjob was something she would like to do again, but without the fear of getting found out.
Right now she just hoped that Bruce wouldn’t tell her sister about it, she counted on him at least wanting to be a little discreet about his cheating. After all if Keira found out she had actually sucked cock she wouldn’t hear the end of it, it was the whole reason for touching up her makeup despite going home.
This time she didn’t even wait for Bruce to get out or offer his arm to her, she just rushed out to the front door with big steps and rung the bell. In a matter of seconds the door swung open with Keira blocking the path to the entrance, a big grin spread across her face. Clearly she had been waiting for her brother’s arrival and the embarrassed stressed look Ashley’s face was exactly what she had hoped to see. Finally she had had her revenge and shown her brother that being a girl wasn’t all fun and games. That would definitely teach him for making a prettier girl than her.
“What’s the matter Ashley? Didn’t you like your date, isn’t it so much fun to go out with a handsome man?” Keira asked, laughing lightly as Ashley pushed past her inside, clearly not wanting to talk about it. Keira didn’t really mind for now, just letting it slip as she felt too good knowing her plan had worked. The only weird thing however was that Bruce just drove off the moment Ashley was out of sight. He looked a little worried as well for some reason.
Maybe he was just disappointed that he hadn’t managed to get Ashley to blow him Despite Keira’s strong motivation. It was a minor set back to her plan, but acceptable, clearly her revenge on her brother had worked which was the main deal. It had to be that right after all if he had managed to get Ashley to blow him Keira thought that Bruce would instantly be in her face with the evidence, demanding to fuck her ass. Oh well apparently just a date was bad enough for Ashley so taking a soda out of the fridge Keira went to the television to treat herself to some relaxation in celebration of getting back at her brother.
Ashley in the meantime just lay on her bed, looking up at the ceiling. The taste of Bruce’s cum was still strong in her mouth as she tried to make sense of everything that had happened. Overall the date had been lovely and she desperately wanted to go on another date with a handsome gentleman like Bruce, one that did know here secret so there was no need to stress about keeping it hidden or worry about tricking someone, needing to perform a blowjob to keep them from finding out. She had loved even the act of giving a blowjob, but she really wanted to perform one on her own terms some time, because she wanted to, not because she felt like she needed to, maybe that would just be an idle wish though, some that would be left unfulfilled.
Bruce for his part was riddled with doubts as well as he drove home alone. He hadn’t wanted to get out to face his girlfriend Keira. He really didn’t want Ashley finding out he was in a relationship with her niece at that, especially not after how conflicted she seemed to have felt after that amazing blowjob. He wondered if he had done something wrong. At moments their date had seemed like the most amazing date ever, then other moments that amazing vibe seemed to be lost to nerves. It was confusing and he really hoped that he could get Ashley to warm up to him more at some point. One thing was for certain, he hoped this wouldn’t be their last date.
Once home Bruce seriously considered whether or not he should send that picture he had taken of Ashley to Keira, it just felt wrong despite it having been the plan all along. Just looking at it got his cock hard again though. Ashley had just been so amazing. Despite how amazing she had been and how Bruce wanted things to work out between them, his arousal did eventually end up getting the better of him.
He had wanted to try anal for a very long time, but no one had ever let him. Now he had everything he needed to make Keira agree to it. After all she was the one who had come up with the deal so it would be crazy not to expect to have to do it right? His cock speaking more than his head and heart he attached the picture he had snuck of Ashley sucking his cock to a message he sent Keira. “Here you are, I delivered as promised, now it’s your turn to hold up your end of the bargain. I would prefer if you came to my place if you don’t mind.” He cockily sent.
A big smirk instantly grew on Keira’s face as she got the picture of Ashley with her lips wrapped around Bruce’s big cock, sucking as if her life depended on it. It wasn’t ideal, taken at an angle from the back of Ashley’s head, yet enough of her face and outfit as well as the cock was visible for her to work with. With the evidence of Ashley getting ready and the date she had set up between her and Bruce she could prove that her brother had sucked off her boyfriend killing two birds with one stone. It was the perfect piece of blackmail to regain firm control over her brother, after all this was something he probably wouldn’t even want their mom to see. At the same time it was the perfect blackmail to get her boyfriend under her thumb.
With a triumphant smile she started typing out her message to Bruce, one laying out her demands instead of agreeing to give in to his. “You just got tricked into dating my brother and letting him suck you off, here have some pictures of him getting ready if you don’t believe me. I can’t believe you didn’t figure out that Ashley might be my brother Ash. I guess it is true that men only think with their cock. Well unless you want the world to know that you prefer sissies over real women like me to go cheating on me with one, you better get any ideas of anal, blowjobs, or any other sex out of your mind. From now on it’ll be I who decide when and how we fuck. Oh also no more fucking around for you either, you can go back to being the wanker you always were.” Keira texted with venom to her words.
As far as Keira was concerned sex would wait for a very long time. While getting laid was something she enjoyed from time to time, she didn’t need it all that much, at least not with a guy and if it meant denying Bruce that was worth more to her than the pleasure of getting laid. Besides, if she played her cards right she could experiment a little with girls. To the outside world they would just look like an adventurous couple who had an occasional threesome, something that shouldn’t harm her career at all while she could explore her feelings towards girls in private. Bruce would just be there for outward show and appearance even if she didn’t plan to let him play along. Oh her future was looking really exciting and delicious, if she could only see how Bruce was beating himself up right now.
Back at his place Bruce was furious, he was mad that Ash had deceived him like that. Hell he still couldn’t believe he had fallen for that trick or the lengths that Ash had gone through to look so good just to trick him. More so than to Ash he was angry towards Keira, after all she was the one who set this up and given from the elaborate scheme this had been her intention all along. All this anger was only further fuelled by frustration for as much as he hated it he didn’t want Keira to spread such lies, especially not with how she could back them up with proof, proof she had tricked him into providing.
Along with his frustration a certain confusion slipped in as well though for as angry as he was, the date he had had with Ashley was undeniably one of the best ones of his life. Despite everything he still felt like they had connected genuinely, that there had been genuine eagerness when she had blown him. As much as he was certain that he wasn’t into guys, he also didn’t know if he would say no to further dating Ashley now that he knew it was Ash, she had just seemed like such a wonderful person on all fronts, someone he’d love to be with. It only made the fact that she had tricked him all that much more infuriating and harder to swallow.
“If that is what you want then why don’t you just fucking break up with me instead?! There is no need to blackmail me and keep this relationship you obviously don’t like going now is there? I’ve never changed for you and I know I have been pushy on fronts, but I never expected you to change for me either if you didn’t want to. I was just upfront about what I wanted out of a relationship, if that doesn’t work for you then just dump me, there is no need to be such a bitch about it.” Bruce eventually sent back out of sheer frustration.
It kind of took Keira off guard, she had never seen it like that given how her mother always raved on about the importance of sponsors and such. She had only ever seen Bruce as a self centred asshole, but she guessed he had never forced her into anything. Still she quickly shrugged off that thought, she had long since made up her mind about Bruce and he deserved to pay as far as she was concerned. “Shut up asshole, and you better not take such a tone with me again or call me any fucking names or those pictures are getting spread either way.” Keira viciously sent back silencing Bruce who only got angrier.
He didn’t dare further voice his anger to Keira, after all he feared that she might actually follow through on that threat. He did really need a place to vent towards though and so his anger turned towards Ash instead after all he was also to blame. As far as he was aware this was just a ploy by the two of them to get to him and that all for his family’s money. “Hey Ash, or should I say Ashley you fucking asshole? I can’t believe you fucking tricked me like that, both you and your sister are scum. I really fucking hope that you both get what you deserve.” He sent viciously.
Ashley was mortified upon reading Bruce’s message. He reacted mad just like she had feared he would, but most worrying of all was the fact that Bruce clearly knew. She could only guess what had happened. She knew Keira had to be behind this, but she had no clue as to how. It was a terrifying realisation as she didn’t know just how much damages had been done by her sister, but she needed to know so she could do damage control. “What do you mean?” Ashley sent back, hoping to learn more about what Keira had done.
“Don’t you fucking act stupid asshole. You obviously tricked me into dating you thinking you were a hot chick. I can’t believe I bought your utter crap. I should have known that you were playing me when you seemed to fucking eager to blow me, I should have known that was the goal since your bitch of a sister coerced me into taking and sending her a picture of it. There I was thinking you really were just a repressed country girl who was genuinely eager to get to know me and blow me. I should have known that the two of you would just blackmail me!” Bruce instantly texted back seething with rage he had no way out for.
The mortification Ashley had felt only grew as she realised that on top of everything else her sister now had even more potent blackmailing material in the form of a picture of her sucking a guy off. If her girlfriend would be mad if it became clear that she felt more comfortable as a girl and as her date with Bruce for as forced as it had been had proven also more comfortable dating guys. She didn’t want to imagine how she would react to knowing he had cheated on her with a guy. She wanted to make the inevitable breakup as painless as possible. After all she did cherish her girlfriend as a person, and she didn’t want her too hurt too badly, but if she truly wanted to be Ashley she would need to come clean to her friends and her girlfriend eventually.
Just like Keira had blackmailed her into going on that date with her boyfriend, she had no doubts that she would use that picture to blackmail her further and potentially cause a very painful breakup with her girlfriends and even her friends. She hoped that at least some of them would understand and support her, but if she let Keira blow things up before she got a chance to explain herself she feared that would be impossible. She was so screwed and she knew it, she hated how Keira was forcing her hand and she realised full well that she would need to inform her friends and girlfriend as soon as possible with her side of the story, before Keira could do her damage. The problem was that she wasn’t ready for it, not yet, but Keira was really forcing her hand here.
On top of all of that there was still Bruce. She had felt as though they had had a real connection and it honestly hurt that he had betrayed her trust by snapping a picture of her sucking his cock. Despite that she was also aware of how much of a manipulative bitch Keira was and so she blamed her more than she did him. Still it didn’t take away the hurt. Not that she could complain about it, she really needed to defuse this situation as fast as she possibly could, before Bruce could screw things up by making Keira exhibit her blackmail. It was a very stressful situation to say the least.
Feeling completely helpless she decided to just come clean to Bruce with her whole story, explaining everything that had happened so far and how Keira had set her up much like she had done to him. “Look Bruce, I am so very sorry that you got wrapped up in all of this, but I really want you to know I didn’t have a choice in this matter. I was set up and blackmailed into this like you were. The only I was so eager to blow you was because Keira scared the hell out of me telling me how I would probably get beaten up if a guy got too handsy and found out my secret. She told me the best way to get out of that situation was a blowjob to get the guy off before that happened. I am really sorry, but it’s the entire reason I was so nervous. I couldn’t let you find out and I couldn’t back out of the date or Keira would have ruined me. Please whatever you do don’t do anything rash, please at least let me try and break it to my friends and girlfriend before any of this gets out. I beg you.” Ashley sent back in true desperation.
It kind of struck Bruce in a way he wasn’t expecting at all, he had been mad beyond believe, but now he realised that Ashley had been just as much a victim of Keira, if not more so than he was. Despite his anger he couldn’t help but feel sorry for her. In a big part because he had actually felt a real connection unlike any other he had had before on their date. It was one of the things that made him so mad, that apparently that entire connection had been fake. He now realised that Ashley wasn’t to blame though, it only further fuelled his hate and fear for Keira. If she did that to her own brother he had no doubts in his mind that she wouldn’t think twice about following through on her threats towards him and even worse. Even without her pleas Bruce realised that not poking the bear that was Keira was in his best interest. He needed to find a way out of Keira’s scheme, for himself and for Ashley, as he truly believed her story and she proven to be a good person even if it was out of fear. He needed to help them both.
“I’m sorry Ash, or Ashley if you prefer that name. I really didn’t know she was manipulating you, I thought you were in on the whole plan and I truly regret lashing out to you for it. It’s just that I was frustrated, I was outraged that it was all fake, just an act as I truly had a good time, I truly felt a click, betrayed and I couldn’t think of anyone to vent to than towards you. Keira just threatened me when I vented and well I couldn’t really say anything to my friends for obvious reasons. I’m also sorry for taking that picture, and making you feel unsafe, but I truly believed you were Keira’s repressed niece and I figured you would never be any wiser. I thought Keira just wanted proof that I helped you open up and live a little, not thinking she would use that photo for anything but that and she did offer a nice reward. I admit I was thinking with my cock and I am terribly sorry for it. Could you please forgive me? I promise not to do anything without contacting you first.” Bruce sent back realising that if anyone had been an asshole between the two of them it was probably him. He had truly enjoyed his time with Ashley and knowing he had betrayed her like that made him feel terrible.
Ashley was very surprised reading Bruce’s answer back. She had fully expected to hear more profanities before he lashed out to Keira and screwed the both of them up. It was very surprising to hear Bruce’s confession that he had really felt a click with her, but in a way that only made her feel even worse. She had almost enjoyed her time with him, and maybe if they had met under different circumstances it could have been the start of something great. “I forgive you, I know first hand what a manipulative bitch my sister can be, so if anyone is to blame it’s her. It’s fine if you call me Ashley, I prefer being Ashley. In any case thank you for not doing anything rash. I know you probably don’t want to hear this, but it wasn’t all fake. I truly enjoyed my time with you for the moments I could put my worries out of my mind. I truly felt a connection and if I hadn’t been scared for my life for being discovered I think I would have actually like that blowjob. In any case. I understand that you probably don’t ever want to talk to me again. I’ll let you know when I notified my friends and girlfriend. Thank you for waiting on that.”
No it was Bruce turn to be surprised, he had never thought he would be forgiven, much less that Ashley would say that she had also enjoyed her time with him as well. Not only that, but he didn’t know how to feel about it either. The fact that it wasn’t just all fake, that there had been a mutual connection, left him confused. How was it possible that he had the best mutual connection ever with what basically was a guy? He accepted Ash’s wish to be Ashley and he didn’t want to offend her, but still he had only known her as a guy before and so had trouble wrapping his mind around thing. Was he gay? No that wasn’t it, Ashley did make a beautiful girl. Hell he even thought that all his friends would agree and that none would be any wiser if they saw Ashley, she had him fooled and he knew Ash better than any of them. Bruce was certain that Ashley would fool all of them as well.
With that thought an idea formed in his head. “A very odd idea just struck me Ashley, and if you wouldn’t want to have anything more to do with me, I would fully understand it, but I think I found a way for both of us out of Keira’s grasp so please just hear me out for a second. What if we went on a second date, after you had a chance to talk to your friends and girlfriend of course. We could go out with a couple of my friends. With what a gorgeous girl you make I doubt any one would be any wiser and if you fool them before they find out about your secret then none of them would probably give me shit if Keira spread that picture. If your friends and girlfriend know then she has nothing on you either. Of course we don’t have to do anything, but I would love a chance to hang out with you again where you didn’t have to worry as much. Despite what’s in your panties I would love to get to know Ashley better. Please don’t feel pressured or anything. I was just thinking it might be a solution.”
Ashley didn’t know what to think when she read Bruce’s plan. If she could face her friends and girlfriend, bring her secret out on her own terms then Keira truly didn’t have anything on her anymore. Then she could fully be who she wanted to be without fear and she realised that it was probably just a matter of time anyways before Keira outed her and ruined all her friendships anyways.
Beyond that she didn’t have to help Bruce, Bruce’s plan was mainly to safeguard him, but she had to admit that she felt for him, and no one deserved to be under her awful sister’s thumb. Besides the thought of a second date with Bruce, and the fact that he wanted to get to know her better really made her feel warm inside. She didn’t know if he was bullshitting her to save his own skin, but after his apology she believed he was sincere. It would honestly be nice to have a second chance at dating Bruce, one without all the stress that came with the first time. There was only one problem and that was Keira, how would she react to them having a second date?
“Alright, I’ll do it, but I’ll need some time to get out of Keira’s grasp so please be patient. I promise I will get to it as fast as I possibly can and I will certainly let you know the moment it is done. Just make sure that Keira can’t get any wind of this or I fear we’ll both be screwed. I would love to get to know you better as well, all cards on the table, but I need to know. Are you only interested to get out of Keira’s grasp, or are you serious about wanting to date me despite what you know. Please Bruce I need to know and I’ll help you either way, but I don’t want to be lead on and hurt so please come clean with me as well.” Ashley sent back, hoping he would be genuine. It would be a dream come true, but she had her suspicions.
Despite all the amazing boosts she had had, she was still terrified of how people would react when they saw the real her, what hardships she would face and if she could ever find someone who truly accepted her for who she was. She was rather confident she could pass as a girl on the surface, and that she could go out in public without too much worries. When it came to actually finding a love interest or even friends as a trans woman she still felt really insecure. Bruce’s acceptance would be a big boost on that front, but somehow she feared that it was too much to hope for.
“I really want to date you for you Ashley, I meant it when I said I thought you were an amazing girl, and I would be lucky to get to date someone as amazing and gorgeous as you. I truly want to give this a real shot and I will be honest, if we really hit it off and take things a little further than just some nice dates, it might be a bit awkward at first. Please don’t take offense if that were to happen. I’ve never been with someone like you before, but I’m willing to do whatever I can to make it work if you give me a chance. It just might take a little getting used to, not because of you, but because of me and I want to be as honest as possible in order not to potentially hurt or disappoint you which I have done enough of as it is.” Bruce replied genuine but careful as he sensed how much was riding on this for Ashley.
Ashley couldn’t help but tear up a little as she read Bruce’s response maybe there was hope for her yet and people could accept and love her for who she was. She certainly hoped so, and she loved the fact that Bruce wanted to try and give it his all. It meant the world to her even if she remained slightly suspicious. She believed him on his word, especially since he had no more reason to lie, but still her insecurities made her doubtful no matter what.
“Thank you Bruce, that really means a lot to me and I want nothing more than to give this a fair chance, but first we’ll have to deal with Keira. I believe you know her pretty well by now so I don’t think I need to say that we should be very cautious. She can’t suspect anything at all until it’s too late for her to do anything to harm either of us. I think it’s best if we even delete these messages just in case.” Ashley sent back going from joy to serious. No matter how happy she was about Bruce’s revelation they still weren’t out of the woods yet and with Keira they couldn’t be careful enough.
“You’re probably right Ashley, your sister really is one vindictive bitch and I’m sure she’ll do as much damage as she possibly can if she finds out we are plotting this. I don’t even know if she’ll agree to let us go on a date, it’ll be hard to sneak off without her knowing and there is no telling what she’ll do. She somehow seems hell bend on leaving me completely denied and cucked not even just happy to break up with me.” Bruce sent back, the worries regarding their plan over taking the relief he had felt that Ashley really wanted to give him another chance.
“Hmmm, I think I know just the solution to that. We won’t even have to keep it a secret, you can just ask her for that date. I mean I think Keira set me up to go out with you in order to torment me, never expecting me to actually enjoy being with a guy. I looked and I was shocked enough when returning home, especially with how things ended up playing out in the car, so she probably thinks I positively hated every moment of it. Since she seems hell bend on screwing you as much as me we can use that to our advantage. I bet she’d eagerly agree to let you take me out on a date again just to give me a supposedly hard time. All you need to do is lay it on thick. Asking her if you can at least work out some of your pent up needs and frustrations on me. Knowing Keira she probably won’t say no to that.” Ashley sent.
“As much as I hate the idea of selling it like that, you might be onto something there Ashley. Keira would indeed be delighted to agree under such circumstances. I’ll work on my seemingly frustrated request right away and you just let me know when the coast is clear to send it her way. In any case I’m afraid I’ll need to go now. Despite how much I want to keep chatting with you I think it might be best if we keep our chatter to a minimum until we managed to get out of Keira’s grasp.” Bruce replied and Ashley could only agree as they both put their phones down and went to bed feeling a lot better about themselves already. Despite all this hardship and the sheer risk thing were finally looking up for the both of them.
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