(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.