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.)