Ash's New Career Pt. 04

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"Did you like the shoot, did you have fun?" Jessy asked interrupting him. Asking a straightforward and simple question.

"Yes, I did, I loved it, it felt so good, hell I felt better and more confident than ever, but..." Ash started, as soon as he sad but however Jessy cut him off once more.

"But did you hurt someone?" She asked keeping a straight face as she saw Ash's confusion.

"No, of course not, how the hell would that hurt someone?!" Ash exclaimed confused and some annoyed at the insinuation that he might have hurt someone.

"Well if you had fun, felt better than ever and didn't hurt a soul, then please enlighten me about what was so wrong about what you did and why it should remain hidden from everyone?" Jessy asked him.

Ash's annoyance went back to confusion then to realisation as Jessy's previous questions suddenly made sense. Still he tried coming up with a way in which it was wrong, but when he took to long Jessy took the word once more. "It shouldn't remain hidden from anyone because you didn't do anything wrong. If you felt better than ever then letting that side of you out, showing it to the world is the right thing to do and don't let anyone ever tell you otherwise, most importantly don't tell yourself otherwise." Jessy exclaimed.

It made sense what Jessy said, and still Ash couldn't shake that nagging feeling that it was wrong. Jessy realised full well what was happening. Coming out, changing your life up so drastically after years of keeping it secret down to some pretty extreme lengths with the black-market hormones wasn't a process of a day. Doubts, being scared, it was all completely normal but she couldn't let Ash spiral down to thinking it was wrong. No today they had made a very important step forward to Ash's self-acceptance and she wasn't going to let it get ruined by negative thoughts. He would get there someday after building enough confidence. She was sure of it.

Wanting to distract him from thinking to much on it, Jessy asked her question again. "So what outfit did you like modelling most?"

"Uhm, well that's hard to say actually. I liked them all a lot actually. I guess if I had to pick one it would be the bikini though. It has always been my dream to model in some kind of sexy surf swimwear shoot so it was definitely a dream come true and an experience that was hard to top." Ash said.

"Well I can tell you one thing. You looked really spectacular in that bikini. There's no doubt in my mind that the pictures from that setting will be fitting for pretty much any magazine cover." Jessy agreed, helping boost his confidence back up as they entered the house and the changing room once more.

"Let me help you get off those breast and hip forms as well as your makeup. I know you might want to keep them on, but trust me, after wearing them all day your skin will thank you for being able to breath again. We wouldn't want you to develop a rash now would we?" Jessy asked playfully as she helped Ash out of his towel and bikini top, going to work with the glue solvent and the makeup remover.

It was somewhat weird and in a way it also was a bit concerning to see the 'breasts' he had had all day suddenly fall of his chest bringing him further back down to reality. "You can take them home with you, and when you want you can always give me a call to put them back on for you." Jessy said, a little concerned, knowing full well what the impact can be of seeing yourself get stripped from that perfect body again.

After removing the hip pads and makeup Jessy said. "I believe you can do the rest yourself in the bathroom. Here are the clothes you wore here, oh and about the nails and the hair let's just act as if I didn't notice those shall we? It looks really good on you." She complimented with a playful wink helping him deal with the going back to normal.

Ash couldn't help himself from embracing Jessy in yet another tight hug. She was so sweet to him and even now after watching his breasts disappear she refuelled his confidence. "Thank you so much Jessy, you are the best." He exclaimed before taking the clothes he had arrived in. The ones Keira had selected for him to humiliate him, but after how everyone had just seen him he wasn't too bothered to put them back on.

While Ash was in the shower Beatrice went about seeing that everyone was paid correctly. She did pull Dean to the side though. "Hey Dean, I know it isn't really usual when I ask for you work, but could I get all unfiltered and non-altered pics on top of the finished collage? It would mean a lot to me." Normally she wouldn't really care about the non-filtered pics, but these would make a nice memory, a memory of the kind of daughter she had always dreamt off.

There were times at which she could have sworn that all of it seemed very natural to Ash, too natural for this to be new to him even. There were times she thought he was having a little too much fun for this to be really forced for him, but the fact remained that Ash had been pressured into this shoot. She couldn't be sure whether or not he wanted this and she was afraid that straight up asking him would put him on the defensive. That Jessy girl and him seemed to get along fine. Maybe she could ask her, or ask Ash some subtle questions in the hope it would clear things up.

Besides Beatrice couldn't risk Ash crashing and potentially doubling down on the denial. Not only would it be a real pity to see him lose his self-confidence and potentially miss the chance at telling her about how he felt if her suspicions were right. It would also risk her plan of pitching Ash as the substitute model getting ruined. No whatever Beatrice did she had to be careful and let this come from Ash himself.

As Beatrice rounded out payments and bid everyone farewell Ash moved out of the bathroom. His very long wet hair was wrapped into a towel and he was back to wearing the dress and lingerie his sister had selected for him. Even though he had to do it without breast or hip enhancements it still looked pretty good on him even if he did say so himself. Moving back into the dressing room he was instantly met by Jessy who gave him a quick wolf whistle, further boosting his confidence. "Look at our natural beauty." She exclaimed, letting Ash know that he didn't use those silicone forms or makeup to look good.

"Now remember what I said about those black-market hormones. You really have to stop taking those. I wouldn't want to see you ruin yourself like that. If you want to use hormones and you are serious about it, my offer to take you to that doctor still stands. If you need me for anything else don't hesitate to call me at all." Jessy once again urged, she really wanted to let it get through to Ash just how important that it was that he stopped those hormones which could have dangerous consequences as their exact composition was unknown.

"I won't Jessy, I promise." He once again said as Jessy pulled him into yet another quick hug, just as his mother arrived in the dressing room to check on them. Realising his mother was there, looking at him in this dress Ash couldn't help but blush a little. Like Jessy had said though, there was nothing wrong about this even if it was hard to express that in front of his mother.

"Jessy, thank you so much again for your service and if we ever need you again in the future I'll make sure to call you. Now it's getting late and I think it's pretty much time for all of us to go home." Beatrice said as she paid Jessy and she and Ash said their goodbyes. She then remained quiet as she walked to the car with Ash, not wanting to jinx anything. In fact it just once again amazed her how natural Ash moved in his dress and heels.

12
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
4 Comments
sissyboi69Aricsissyboi69Aricabout 2 years ago

I love this story; I hope that his sister comes around and excepts him.

Joann69Joann69almost 3 years ago

I'd love to see more

AnonymousAnonymousabout 3 years ago

It would be cool if there is ob top of each part a quick summary of who is who. It's hard to keep track, if each part of the story releases a month apart

FibaroFibaroabout 3 years agoAuthor

Hello everyone,

I'm going to use this oportunity for a shameless plug in,but if you want to help me and my stories you can support me on Patreon. On there I post a minimum of 4 story parts a month, one which can be voted for each month. I also post up to 4 comissioned artworks a year. In reality I post more like 6 or even more story parts each month.

It's thanks to my Patreon that I've been able to incease my upload speed on here to 3 parts a month. If you can't or don't want to support me on Patreon everything there will eventually be posted for free. It'll just take longer. https://www.patreon.com/Fibaro

Kindest regards,

Fibaro

Share this Story

READ MORE OF THIS SERIES

Similar Stories

The Agency Mike finds a job, which may be much more than he expected.in Transgender & Crossdressers
A Boiled Frog Pt. 01 Wife slowly brings husband into feminine lifestyle.in Transgender & Crossdressers
A Model for CC's Linda tricks a guy into becoming a model for CC's.in Transgender & Crossdressers
Secrets and Surrender High school can be lonely, but shared secrets can help.in Transgender & Crossdressers
Popping His Cherry She finally makes him her woman.in Transgender & Crossdressers
More Stories