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.

(If you like my story, 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.)