Ash's New Career Pt.2 (Patreon)

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?