Ash's New Career Pt.10

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Chapter 13

Keira was feeling on top of the world and it felt like nothing could spoil her mood ever again. She had full control over both her brother and her boyfriend, the two biggest annoyances in her life. Now they provided her with more of a thrill than an annoyance though. There was just something so powerful about keeping them both under her thumb. Her brother might have wowed everyone and gained their mother’s favour, he might actually have been happy with how passable of a girl he made, but now she had him back under her thumb. As for Bruce now it was her time to fuck around, and she didn’t hesitate to place a personal ad looking for a girl who was into cucking her boyfriend.

In the meantime she didn’t really care about Ashley, she stayed out of her way afraid to make a wrong move as far as she was aware and she was perfectly happy with that. The only thing Keira wasn’t aware of was how Ashley was undermining her control at this very moment. The day of her date with Bruce and the following blackmail she hadn’t left her room at all. Only the day there after, after making sure her mother was already downstairs, she finally emerged form her room.

Ashley had treated herself to a nice long bath this morning after sleeping in lavish satin pyjamas for the second night in a row. She had put on a nice flared burgundy coloured skirt. For a top she had chosen a nice cream form fitting turtleneck. It showed the curve of her breast forms off perfectly while simultaneously hiding the silicone so no seam would show as she was no where near as good as blending the makeup there as Jessy was. On her legs she pulled a pair of sheer black pantyhose and finished the outfit off with a pair of brown leather ankle boots with a three inch tall chunky heels. In order to add some extra style and cuteness to her lovely outfit, she had applied some light natural looking makeup, and tied her hair off in a high ponytail with a burgundy coloured satin bow.

She was a bit nervous to encounter Keira as she stepped into the hallway, getting on a hurry to move downstairs only to relax when she met with her mother down in the kitchen. She was staring right at her over her morning cup of coffee. It felt a little awkward for Ashley as she walked over to her mother’s side and greeted her with a peck on the cheek before turning to the coffee machine for a coffee of her own. “Uhm hi mom, good morning.”

“Good morning to you too sweetie. I’m sorry for staring, I just couldn’t get over what a gorgeous girl you make. I’m afraid it’ll take some getting used to. Great choice of outfit as well, I love it.” Beatrice mused in awe of what a pretty passable girl her new daughter made, it was weird, especially since she hadn’t seen it coming at all, just a few days back she had still seen Ash as all boy. It was lovely to have one of her children who inherited her style though.

“That’s okay mom, I guess I can’t really expect you to act as if I’ve always been your daughter, it has been a rather radical change after all. I’ll admit it felt a bit strange for me too, to come down wearing a skirt, but it just feels so right you know? In any case what I’m trying to say is that I am truly grateful that you make the effort to accept me for who I really am. It means the world to me. Coming out to you has made me realise just how much I have been repressing and it made me realise that I can’t go back to being Ash. I kind of wanted to wait to come out to my friends, but I can’t put on that façade again so it can’t really wait I guess. I was actually thinking of meeting up with Jessy today to have a talk about how I could come out to them. She has some experience with people like me after all, maybe she has some tips to make it easier?” Ashley said as she joined her mother at the table.

“I think that’s an amazing idea sweetie and if there is anything at all I can do for you to help you out I will be more than glad to. You just let me know okay? By the way, would you like to know how my contract negotiations for you went yesterday?” Beatrice asked with a sweet smile, hiding her slight nervousness. She was afraid that some people might react poorly to Ashley’s coming out, that they would hurt her. Things were moving very fast and rapidly so. If it had came as a shock to her, she imagined it might be the same to her friends and girlfriend. She tried hard not to let her nerves show however, if Ashley would be hurt then she would be here to take care of her, the last thing she needed were extra worries. Besides going to Jessy sounded like a superb idea, that woman had been a great help already and had done wonders for Ashley.

“Oh yeah sure, I would love to mom, sorry that I haven’t asked, but I’m dying to know. It’s just that I’ve had a ton on my mind these past few days so that bit kind of slipped my mind.” Ashley said somewhat nervously. She could hardly tell her mother what had happened yesterday as it would probably break her heart, but it had caused her to have a lot on her mind. As curious as she was about the results of the negotiation, she was also kind of scared of the outcome, fearing that she would be rejected because she was no real girl, something that Keira had tried to make awfully clear, yet her mother’s cheerful mood kind of gave her hope.

“That’s completely understandable Ashley, don’t worry about it at all. It’s just that I have some exciting news and I bet you would love to hear it. The company would love to work with you. They adored your portfolio and they would love working with you to become the face of the new hair product line they want to roll out. They thought you would be an even better fit than the model originally supposed to take the job. Hell they even threw in a bonus just for you and if the shoot goes well, they would love you to model for their skin care lines as well.” Beatrice said enthusiastically, loving the amazed and excited look on her new daughters face.

“It should take a month or two for the first products with your face to be published. So if you would rather wait with your coming out you definitely have time to think things over. That being said just do what you think is best. I love you sweetie and that won’t ever change.” Beatrice spoke, grabbing a firm hold of Ashley’s hand in support.

“Thanks mom, that means the world to me, and you can’t believe just how happy I am that a company wants to sign me on as a genuine model. I can still hardly believe this is real, I mean wow, I really don’t know what to say.” Ashley said mesmerised, touched by her mother’s support and the unbelievable outcome of her mother’s negotiations. She really couldn’t believe that a company actually thought she made a pretty enough girl to become the face of a new line of products they were about to roll out. It was a huge compliment, one that meant so much more than her mother telling her how cute she looked. After all her mom might just say it to make her feel good, companies didn’t do that. It gave her such a confidence boost which made her feel a little more at ease with her plans to come out. This was exactly what she needed right now.

“You don’t need to say anything sweetie just remember this when you are struggling a little. You are a gorgeous amazing girl I am lucky to be able to call my daughter. Never forget that sweetie, I’m proud of you.” Beatrice spoke as she got up and gave Ashley a tight hug. It was a bit strange to feel the bra straps, and smell the flowery shampoo in the hair of who she had considered her son just a few days ago. None of that mattered though, Ashley was her daughter now and that was great just the way it was.

“I really appreciate it mom, thank you so much for everything. I never thought this whole bet with Keira would get so out of hand, but I’m glad it did. It was the push I needed to finally be open about who I really am, and I’m infinitely grateful for your amazing support mom, I mean it. Oh I bet that is Jessy.” Ashley said, interrupting her heart fell speech when a text message rolled in.

Beatrice stepped back with a big smile. It warmed her heart to hear Ashley say that. It made her feel so much better knowing that Ashley didn’t really blame her for not having seen her for who she really was all along. Seeing the smile creep onto her new daughters face as she read that message made her feel even better. For as much as she feared for Ashley and how her friends would deal with her coming out. She had a feeling that everything would be alright. This Jessy sure seemed to be able to put a smile on her daughters face so in the worst case she had a new friend if things wouldn’t work out with her old friends.

“I’ve got to go mom, Jessy has some time on her hands for a quick brunch now, but then she has to go do some work. I hope you don’t mind me rushing out, I appreciated our talk, I really did. I just want to see to see this whole coming out situation resolved as soon as possible.” Ashley explained apologetically not wanting to offend her mother who had done so much for her these past couple of days.

“I don’t mind one bit sweetie, I hope she’ll be able to give you some sound advice you feel happy with. Oh and while you’re at it don’t forget to have fun. I know I always enjoy my brunches with my friends.” Beatrice smiled, giving Ashely a tight hug before waving her out at the door. Things sure did look like they were going to be alright going forward, she only hoped that Keira would come around as it did hurt how her other daughter couldn’t seem to be happy for Ashley. She loved both her children after all.

Chapter 14

The drive over to the address Jessy had given her was a relatively quiet one where Ashley was more happy than she was worried like before when she was about to head out in public. Having passed on the shopping trip with her mother, the date with Bruce and especially now that she had actually gotten that modelling contract which she could still hardly believe she had gotten, gave her such a confidence boost. If all those things proved one thing, it was that she didn’t need to be afraid to be who she was among strangers.

Nevertheless she was pretty happy to arrive at a rather quiet cosy place outside the city, not because it was more private and had less people, but because it showed that Jessy cared greatly about her comfort, not knowing the progress she had made yet. She was already excited to tell her friend all about what had happened on that shopping trip with her mom, about the modelling contract and about the good things that had come out of that date with Bruce. She just knew Jessy would be happy for her.

Making her way into the cosy building Ashley took a few moments to spot Jessy in one of the more private parts of the establishment. With a big smile she instantly headed over to her, only for her smile to get even bigger when Jessy looked right at her and still took a few seconds to recognise her at which point a look of sheer amazement crossed her face. “Oh my god, Ashley is that you? You look spectacular.” She gushed, instantly getting up to embrace Ashley in a tight hug as she arrived at the side of the table. She knew how good Ashley could look after she had made her up for the shoot, but given how shy she had been only a few days ago, Jessy didn’t expect to see such a gorgeous and even confident girl back. She had expected Ashley to have taken out the extensions, removed her acrylic nails, left out the breast forms and to have worn her old male clothes. She had been expecting to meet Ashley looking more like Ash.

The long and tight embrace ended when Jessy took a step back only to give Ashley a thorough once over, admiring her look. “Damn girl, do you happen to have some style tips, cause I could definitely learn a thing or two from you, your outfit and makeup are simply lovely. You can’t believe how happy I am to see you as the real you with confidence and pride at that. Then again, I imagine you should feel proud when you look in the mirror.” Jessy gushed, further boosting Ashley’s confidence. She was definitely underdress compared to her friend wearing a simple pair of pale skinny jeans, a white tank top and a black leather jacket.

“I’m very happy to see you as well Jessy. As for that confidence you have yourself to be proud of for the most part. My mom has been very supportive and has taken me out shopping, but without you bringing out Ashley and giving me the confidence to be myself, I would have never dared go with her. A lot has happened these past few day. Like you wouldn’t believe it. I think it would be best if we sat down cause I have so much I want to tell you.” Ashley said as she took a seat with Jessy eagerly doing the same thing, all to happy to hear about this true metamorphosis Ashley had gone through since she had last seen her.

After their ordered some drinks and food Ashley went on and on about the amazing shopping trip with her mother, sharing a little about Keira’s blackmail that had led to a scary, yet somehow wonderful date with Bruce. A date that had definitely sparked something between her and Bruce as she talked about their plan only to conclude everything on a wonderful note with the contract her mother had just told her about. Throughout Ashley’s story Jessy had felt everything from warm and fuzzy to blood boiling rage at Keira, she couldn’t believe that bitch of a sister still hadn’t stopped tormenting Ashley, especially when hearing how extremely far she had taken it. At least it was a relief to hear how Ashley was taking it relatively well considering the damning circumstances.

“So I guess what I’m trying to ask is if you could give me any tips as to how to come out of the closet towards my friends. Also if you still want to help me with that I would greatly appreciate it if you could accompany me to a specialist on the front of transitioning. I’ve stopped using those unregistered drugs like you insisted, but I’m certain I want to embrace who I really am.” Ashley concluded her story, kind of surprised about how emotional it left her. Recounting it all to someone she truly trusted really made her realise just how much she had been through in such a short time.

“First of all let me say how truly sorry I am that you have such a shitty sister who has put you through such horrid things. I would love to give her a piece of my mind, but I fear you are right about the trouble she might cause. No one should be forced to come out, but I’m afraid you are right that time is ticking if you want to come out on your own terms despite how much I despise that. Secondly I can’t tell you enough how much I respect this great confidence and drive you are showing despite all that has happened.” Jessy spoke, affectionately grabbing onto Ashley’s hand across the table.

“But those weren’t your questions. My answer is yes Ashley, I admire you greatly and I’ll do whatever I can to help you. As far as coming out is concerned I suggest you do it slowly, give them a chance to ease into a it a little. You make a gorgeous girl, but I would suggest wearing a pair of feminine jeans and a t-shirt when taking that step. Maybe don’t wear your breast forms either. I suggest you go for a slightly feminine look leaning more to androgynous. It will be easier for them to grasp and accept that way rather than blowing them away with what a stunning girl you make. I know it might feel wrong, and I do advise you to feel what you think will be best, after all you are the one who knows your friends best. Toning down your look a little will make it an easier pill for them to swallow though.” Jessy advised.

“As far as the specialist is concerned I’ll contact her and let you know when she’ll be available so we can put our agenda’s together and make an appointment. I’ll call in a favour to get it done as fast as I can, so don’t worry about that, I’ll contact you when I now more. In any case, tell me about Bruce, is he cute?” Jessy asked cheerfully trying to lighten the mood with some regular girl talk, to take away some of Ashley’s obvious stress.

Despite the fact that there were some bad memories connected to her date with Bruce thanks to how Keira had forced it upon her, Jessy’s tactic worked wonders. Ashley thought Bruce was quite hot and as it turned out he was quite nice contrary to what Keira’s bitching made believe. She talked on and on about Bruce with Jessy asking the occasional question to keep the talking going seeing how excited Ashley was about the subject. It was very nice to hear Ashley so passionate and happy, besides, Jessy was also happy to give her some genuine tips about dating guys, tips specific to Ashley’s situation rather than the horrid advise Keira had given her.

By the time they finished with their brunch both Jessy and Ashley were surprised to see how much time had flown by. “Oh damn, I’m very sorry about this Ashley, but I have to get a rush on as I have an appointment to make. Looks like the time really flies when you are having fun. We should definitely do this more often. In any case best off luck and I’ll catch up on you sometime soon okay? Remember Ashley, you can always call me if you need me and if you ever doubt yourself remember what an amazing, strong young woman you are.” Jessy rattled giving him a quick hug and a peck on the cheek before nearly jogging out.

The ending was a little abrupt for Ashley’s liking, but then again that was just because they had been having too much fun so she didn’t mind at all. She had known from the start that they only had limited time, quite a bit of it, but so it seemed still too little. In any case Jessy had once again come through splendidly for her, she was such a valuable friend and she didn’t know if she could ever have been Ashley, or at least not so soon if it wasn’t for her. Once again she had taught her so much and boosted her confidence beyond believe. So it was with a bright smile she left the brunch place. A smile shared with Jessy who was more than happy that she had been able to help Ashley out. She was still mad that Keira would do such a thing, but she was confident Ashley would get through this.

From the cosy brunch place Ashley quickly headed back to the mall. All her excitement to finally be herself on her shopping trip with her mother had left her neglecting to buy anything that could be remotely androgynous, but Jessy was right, it was best not to shock her friends and girlfriend at full force so something more androgynous was exactly what she needed, something girly for sure, but less extremely so than what she was currently wearing. She already missed it just thinking about it. Pantyhose and a cute skirt just made her legs look so fantastic. Seeing how she felt about her search Ashley was once more convinced that she was really made to be a girl.

While she was a bit nervous to head out in the mall all on her own she forced herself to take the leap and in the end she was happy she did as roaming through the halls of the mall alone only fuelled her self-confidence. Jessy and her mom could reassure her that she looked perfectly passable and gorgeous all they wanted, but that just wasn’t the same. Ashley knew they would say that no matter what. Seeing the looks complete strangers gave her however did help reassure her a lot. No one looked at her like she didn’t belong. Some girls were subtlety checking out her outfit while nearly all the guys she passed checked her out in a not so subtle manner. The stares some older men fixed her with were a bit unsettling at moments, but she just tried to ignore those with her head held high. It was something that sadly came with the territory and while she would have rather missed that part she guessed there was a silverling there that she was worth looking at.

Unlike last time Ashley shopped more targeted, going straight to one of the lower end stores rather than doing every single one of the stores. She figured that if she had to wear pants and a t-shirt it might as well be a cheap set as she didn’t plan on wearing them for than a few times for introductions sake. Even so she had a way harder time figuring out what outfit to actually buy. Unlike with her mom, she wasn’t looking for her hearts desire, the cutest outfits she loved most. She had to like it to some degree for sure, but this time appearance sake towards her friends and girlfriend was more important than her own style was.

The last thing Ashley wanted was to go back to looking like a guy making it exceedingly hard for her to settle on an outfit. An outfit that looked both cute enough to feel comfortable in, yet plain and unisex enough not to create too big a shock among her friends and girlfriend. In the end she settled on a pair of light denim skin tight jeans that fit like a glove, accentuating her nice bottom and long legs, stopping an inch or two above her ankles. They felt like a sturdy pair of leggings and none of her friends ever wore pants like this where her girlfriend sometimes did. They were plain without any decorations, only the style setting them apart as effeminate. The t-shirt she settled on to go with it was a plain white one with a tiny logo on her left breast. The waist of the t-shirt was subtly nipped in, it had a v-neck and the sleeves were on the short side. It did once again convey a more feminine style without being too obvious.

To try it on Ashley had taken off her bra and breast forms leaving her completely flat chested. She kind of missed having breasts already, but she needed to see how it would fit without. If she thought away the long painted nails and the more elaborate makeup she guessed she could pass as a plain yet cute looking flat chested girl. She wasn’t all that confident in her own ability to judge whether or not this outfit was good enough though. So instead of simply buying it she snapped a quick picture in the changing room’s mirror and sent it straight to her mother and to Jessy. “I need a second opinion, do you think this is plain enough to meet my friends in? Isn’t it too much? Or maybe a little too plain?” She asked.

As strange as it was, seeing Ashley in her jeans and t-shirt combo, did put Beatrice’s mind a little at ease. She was exceedingly happy to have a daughter as smitten by fashion and modelling as she was, and she wanted nothing more than for Ashley to be happy, yet the thought of how others might react to her coming out was a little unsettling. She didn’t want Ashley to hurt after having to hide the real her for so long and she sincerely believed that this more modest outfit would be a good way to take it a little easier. “You look wonderful Ashley, I think it’s a perfect outfit choice and I am more than happy to give advice whenever you might need some. X Mom” she replied.

Just like her mother Jessy was also sold on the look. “It looks perfect Ashley, I love it! While it’s a shame to see such great legs as yours in pants I think you still make the outfit look amazing. You can pull just about anything off can’t you? Then again, that’s no surprise with someone as cute as you. Go for it Ashley, you got this, I believe in you, and like I said, feel free to call me whenever!” Jessy replied enthusiastically, both positive advices giving Ashley the confidence she needed to settle for this outfit.

Feeling a little more confident and comfortable with her choice Ashley quickly changed back into her skirt which still felt many times better than the pants no matter what. Having her chest back was also nothing but a joy as she quickly collected the jeans and t-shirt only to head for the counter, happy to get this settled as well. Although deep down she knew this was the easy part. Actually breaking it to everyone she knew would be the hard part.

Having successfully shopped for something she didn’t necessarily like, at least not as much as all her other purchases, but nevertheless something she sorely needed, Ashley decided to treat herself to a smoothie at one of the hip bars in the middle of the mall. She sat out in plain view, not even attempting to hide herself from anyone, she didn’t feel like she needed to do that anymore and she really wanted to conquer what inhibitions she still had left about this new her, the her she was more and more certain she wanted to be on a permanent basis.

There was only one real obstacle left for that to happen, and that was telling her friends and girlfriend. She had been avoiding them these past few days ever since that shoot was forced upon her by Keira, the shoot that had in the end proven to be the catalyst she needed to finally discover the real her. She couldn’t continue to avoid her friends for very long and she didn’t want to go back to being Ash so she would have to show them Ashley in short notice. As it turned out she wouldn’t need the old male clothes she had saved after all as she was very determined to come out, to save herself and Bruce who all in all was a pretty great guy from Keira’s clutches.

Unbeknownst to her sister she had once again given her the courage and the strength she needed to force through another big leap in coming out. All in all despite the plots Ashley was pretty much feeling as if she should thank Keira for all she had done, even if only to see the look on her face when she broke it to her that she was the one who had allowed her to find true happiness in life all while trying to get back at her. It was bound to be precious, but that had to wait a couple of days until she and Bruce were safe.

Right now she just basked in the moment of peace she had, enjoying her freedom as the true her while she got nothing but confirmation from those passing by, checking her out in subtle and less subtle ways, further fuelling her confidence as Ashley. It felt down right amazing just to be able to go to a nice bar as a girl with no one judging her like she had always feared they would. It was amazing to be accepted even by complete strangers.

While she enjoyed the reaffirming attention she was getting Ashley turned to her phone and started texting her friends to apologise for not being available for a couple of days and asking to meet up tomorrow. She only had a small circle of really close friends she wanted to announce it to in person as soon as possible. For the others she cared less if they found out through the talk that would surely spread, or when they happened to hang out at some point after she came out as Ashley. Nevertheless arranging everything for tomorrow was one hell of a chore as she wanted to talk to all her friends and her girlfriend within the same day to prevent any of them from hearing about it from someone else. Her heart was nearly beating out of her chest and her nerves were raging inside as the plans started to form. This was all becoming very real, and she couldn’t help but feel scared for their reactions, nevertheless she continued planning.

( If you liked this story and would like to read way more along with a ton of other stories then please check out my page on SubscribeStar: https://subscribestar.adult/fibaro I have ran into trouble with Patreon, but since SubscribeStar doesn’t accept PayPall you can still follow me there, just make sure you connect your discord account to your Patreon account if you do so you don’t miss out on my content. https://www.patreon.com/Fibaro )

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