A little late night show

Aiden could barely finish his meager dinner. He didn't know if it was because of the corset, the video he just received or the fact that he would be participating in a live session in just a few short hours. All he knew was that he was sick to his stomach. Eventually he was able to **** down what little food had been provided to him. The rest of the meal with his ex consisted of mostly just small talk. Him having to act excited about finally getting a GED and going on a date Monday evening and a chance to get back out into the workforce.

“I know you must be so excited Amber. Ever since your divorce you have spoken about wanting to be more open with your sexually after you were **** to repress it for so long. I know society likes to view women like you…. negatively. But I say there is nothing wrong with being a slut! If men can sleep around and be praised for it, then why not us women.” The way she looked at him, the little smile, the raised eyebrow, he knew she was waiting for him to respond.

“ I ah, ah, I know, Right! Thanks like, sooo for your support!” So supportive you are literally pushing me into sexual activities I don’t want to be part of.

“Are you excited for your little cram sesh with that waiter boy?” Cram sesh? Vicki had been one of the smartest people he knew, hearing her talk like… well like how she wanted him to talk felt odd, but he supposed she was talking to her supposed bestie so he would have to reply in kind.

“Oh.Like.Totes!” Aiden said, taking a small pause between each word and adding emphasis on the last one. “He is such a little hottie. I can't wait to see him… In action.” He choked on those last few words. Barely able to **** them out.

“Goodie! I know you are going to be so encouraging to him. I don't know how guys can get off to that. My ex-husband, you remember him. The horn dog that could hardly keep his eyes off any woman's chest. He used to have cam sessions with his whores…I mean girls, sorry no offense.” she said with a wicked smile, enjoying talking about Aiden like he wasn’t in the room. “He did it all the time behind my back. I mean, if he didn’t hide it his ass would have hit the pavement long ago. If only I didn’t keep making excuses for him. Well they used to talk dirty to him to get him to finish. Touching themselves. It just seems so dirty to me. But if you find it hot Amber. Then you do you girlfriend!”

“It is like, so hawt to like to watch a guy cum for me. I just love helping him get all hot and stuff.”

“Oh wow. Look at the time you have a zoom date to get to. I have an old laptop you can use too, sweetie.” She said as she got up from her spot disappearing into her room only to return shortly with an older macbook pro. “Now Aiden.” Victoria said seriously, dropping the act. “I expect you to give him a good show. Or there will be hell to pay. Understand?”

“Like of course Vicki!” Aiden stated, deciding to not drop the Amber persona, he didn’t want to get lured into some trap. Not with how she had been acting. He wasn’t sure why she wanted him to use this old laptop instead of his much newer and better one, but arguing wasn’t going to get him anywhere. Not doing this on his own laptop actually sounded better to him when he thought about it. Taking it he walked to his room with as much real excitement as a man walking to the noose, while outwardly he kept a smile on his face big enough to just show off his pearly whites.

Sauntering over to the small desk he sat down, trying to get into the right headspace he thought of Amber as a different person, like she was just a character in a video game that he was controlling. It wasn’t him, just a character, he was just controlling a character, it wasn’t him… he repeated mentally, hoping the repetition would make things easier. It was Amber who was sitting down in this dark room and it was her opening the laptop he thought as the glow from the screen added a little light to the room. He could have turned the light back on, but what he was about to do felt much more tolerable in the dark.

Double clicking on the zoom app he noticed it was alright signed in as SweetAmberGold, the same as the email address Vicki had set up for him. He looked back towards the open bedroom door, wondering if he should close it or not. He considered closing it and then not following through, but he also knew she had the ability to text as him with some parental control feature for the phone she got him and that could cause trouble if he didn’t follow through. Vicki hadn’t told him to keep the door open he thought again and the small measure of privacy would be welcome. Getting up to close the door he sat back down, the cursor for the mouse hovering over the screen name Collin had given. Aiden considered getting up to get a drink, but he knew he was just trying to put it off as long as possible. Taking a deep breath Aiden, or as deep as he could with the corset squeezing him like a vise, he joined the meeting.

A few notification screens popped up. He was too nervous to read them, so just clicked accept. His education and career experience told him he shouldn't be accepting anything without reading it, but also not accepting meant he wouldn't be able to use the application, so he didn’t bother. The next thing he saw was the young man from the restaurant, the only difference was he was now shirtless. He had a confident smile on his face, a smile he would often wear when talking to a beautiful woman, except now the heel was on the other foot, so to speak. Aiden’s eyes drifted to Collin’s abs, a spike of jealousy filled him, silently wishing he would have kept up with his physical health during this trying time. Not that he ever had a full six pack like Collin did.

“Like what you see?” Collin asked the knock out who was clearly enjoying the view as much as he did when looking at her.

“I got to be honest, you're making me feel a little underdressed.” Aiden let out a nervous giggle, knowing what he was getting at.

“Oh yeah sorry...I just finished eating with my wif...my ex.” He said nervously not having a clue about what to do or how to proceed. Suddenly a chat box appeared on his laptop with the screen name BossVicki.

BossVicki: It sounds awfully quiet in there. Do I have to remind you what will be expected of you so that you do not blow your cover? Come on girl get the show on the road. Or I will just invite him over for you to blow him instead of your cover.

Realizing he had little to **** he took another deep breath thinking of his experiences on Collin’s side of things when he was doing things with his mistresses.

“But anyway baby I guess I could get a little more comfortable...would you like that?” Aiden asked slowly, removing the strap of his dress showing this young man the top of his bra and even more of his delicate cleavage. Aiden cupped the fake breast, running his thumb over the nipple through the bra. In the top left corner of the screen was a smaller image, showing what the camera on his macbook was showing. His member maybe have been tucked back between his legs, but it started to wake up seeing the hot redhead start to touch herself.

“Oh babe, I would love that! You are so sexy!”

“You're like, not so bad yourself… stud” He said, giving him a sexy little smile and wink removing the other bra strap. He then shimmied the dress further exposing his corset. “Ohhh this corset is like sooooo tight… can you like, just imagine your hands around me instead?” Amber, Aiden repeated the name it was Amber doing this. It was her that started to run her hands up her sides, cupping her breasts before moving them above her head as she leaned back in the chair. Aiden licked his lips, his full attention on the tiny window showing himself instead of Collin.

“Well then take it off!” She, right now he was just Amber, Amber was a she. So it was her who heard Collin tell her to take it off. It was Amber who gave the young man a flirty smile. A small whimper came to his lips as his mind tried to reconcile things.

The whimper turned into a giggle, Amber biting her bottom lip before replying. “OK if you insist.”

“I do.”

Pushing her chair away from the desk and standing up to give the young man a complete view of this redheaded goddess that he was… pretending to be. Amber looked at him again as he moved his arm lowers off screen moving them up and down. Knowing Collin would be watching Amber turn around to show off her skirt covered ass, the dressing falling to the floor, showing off her panties now that she was standing and the straps no longer held it up. He knew the sight had to be driving the young man wild as she unclasped the corset, slowly letting it drop to the ground. With the corset gone and his backside to the camera he had Amber bend over so the man on the other end of the lens got a good view, while he finished taking off the next article of clothing, the bra.

Not having the bra straps dig into his shoulders felt good, women complained about wearing heels, but he wasn’t sure why more didn’t complain about bras. It felt good, and while he would love to enjoy the freedom from the garment, right now he had to have Amber continue the show, to do her best to copy the same moves he had seen girls do on calls l like this or things strippers did. He had missed something with the dress falling, he knew he could have teased it more. Bending down at the knees Amber pulled it back up, covering her rear once more. He had her shimmy around in a slow circle in front of the camera. Giving Collin a bright smile before turning back around, catching the excellent view of what he was seeing in the small window.

Collin watched the girl hook her thumbs in the dress that now wrapped around her waist and hips as she began to lower it down slowly, bending over in the process to give her audience a perfect view of her pert and juicy ass.

Slowly stepping out of the dress she let out a breath, reminding herself that right now she is Amber, a recently divorced slut looking for fun. The thoughts slipping from Amber being a third party, to a character he inhabited as she turned around showing Collin her big exposed tits before sitting back down in the chair. As she sat down, legs pressed together she slid her long nailed fingers across her upper thighs, before slowly spreading her legs to expose the front of the white lacy panties. Not giving a single sign of the semi hard dick that was between her legs, pressed against the hard surface of the chair. “That's better wouldn't you say?” Amber said with a slight teasing tone, seeing for the first time that Collin had gone from just watching to learly masturbating at the sight of her.

“Much better, My god you are the sexiest woman I have ever seen!” Collin said without making eye contact, his eyes clearing staring at the now exposed tits. “Oh right you probably want to see huh?” Aiden wasn’t sure what he meant, adding a little confusion to the situation that had already started to mess with his head. See what? He wanted to ask, but before he could the question was answered. The screen shifted, no longer could Aiden see the face of Collin as the camera tilted down showing his rather impressive dick that Vicki had said or implied it made him gifted. The screen was at that point dominated by the sight of the man’s stomach and cock as he stroked the thing that looked more than two handfuls.

“Oh wow it's like sooo big!” Amber said it knowing it would play well, but Aiden knew it wasn’t a lie. Collin was bigger than him, he wasn’t exactly small, but not… gifted like him.

“Thanks doll. What do you want to do with it?” He asks expectantly. Amber knew what he wanted.

“Oh I want to suck on it baby. I want to wrap my warm lips around it!” Amber said as she moved the fingers of one hand to her mouth. Pressing her index finger to her bottom lip she opened her mouth, biting down gently on the long red nail, while the other hand came up to touch and squeeze her breast. The sight turned Aiden on enough that he unconsciously started to rock his hips, causing his inflate member to rub on his panties.

“Oh you can suck on it babe. Right after I fuck those titties!” Collin said increasing the speed of his hand.

“Oh these titties?” Collin heard Amber ask as she began to squeeze and rub her tits like the women on so many porn videos he had watched.

“Yeah Mmmm… those tits baby. I want to fuck those tits… and your mouth. God your lips look perfect for sucking cock, I want you to suck on my cock so I can cum all over that hot little face of yours! Mmm mmm!”

“OOOOOO cum on my face Collin baby, I want it so bad” She squealed even louder. Aiden’s eyes glued to the little window, seeing the girl dry humping the air as she played with her chest, her finger touching her tongue. He was unable to not see what was displayed across most of the laptop screen, he tried to focus on her, but knowing she was doing that, what she was doing to the other man he had to agree it was hot.

Amber began to speak louder, Aiden’s own excitement playing a part now as she continues to play with her chest. He watched on the screen as she moved the hand away from her mouth down to her panties and began rubbing her hidden member. Thinking how she used to love watching women rub themselves… like he was doing now, hoping Collin would love it too so this nightmare of an evening could finally end. Amber pressed her lips together, stifling a moan she noticed on the bottom of the screen an icon of a camera with a little red dot on it. Paying it no mind Aiden looked back to the little window of Amber, his eyes sliding across the now precum covered dick of Collins as he worked his shaft. The image didn’t linger in his mind as he looked at a hot redhead squeezing her tits and rubbing her pussy through her panties, the erotic sight made him start to feel his a build up of his own.

“Almost… almost there...so close!“ As Collin said those last words he grunted loudly, finished blowing his load all over the camera blurring the image so Amber couldn't see Collin, only the dripping of something slimy and white. “God babe that was so hot. I can't wait to do that to you in person!” The reminder that his wasn’t the end, just the first act in his time with Collin brought an end to the erotic feeling. Aiden had been close to cumming again, but now he felt himself deflating at the knowledge he would be meeting up with the young man again after the weekend.

“Yeah baby it was like soooo Hawt! I cant like wait to see you on Monday!” Aiden said the words happily with a chipper giggle, but there was no real feeling behind it. He wasn’t angry, disgusted or anything, at that second he just felt hollow.

“So yeah I got to head out but I will talk to you later. Good night beautiful! Rest well, I know I will thinking of you.”

“Good night stud.”

Clicking the end call button he felt himself tear up, an emotional response that often came with pain, sadness and sometimes joy. He felt none of those things at the second, only shame. The tears in his eyes were tears of shame. This was by far the worst thing he had ever done in his life, worse was he had gotten turned on by it. Something he was not going to mention to anyone, ever. Vicki expected him to do this, be this person, but for how long? Until he could find work again? Until this agency was able to work him up a decent reference? The walls felt like they were caving in. He wanted to crawl into bed and let it all pass, but soon as he turned in his seat a knock came to the door, it opening right after.

“My,my,my that was a hot little show you gave that boy wasn't it? You hot little slut.” Vicky teased the feminized man as he tried to cover up his exposed new breast. “I got to say I am proud of you honey, are you excited for Monday? I bet he is.” Knowing what she expected him to say, Aiden, as Amber perked herself back up.

“Like totally I can't wait to see that hunky man!” He tried to act enthused, even as the tears in his eyes refused to go away.

“Well we better get to bed. Today was a long day and you have even more training tomorrow.” Leaning closer, Victoria kissed the forehead of her pretend best friend. She had been so powerless in their relationship and even at work her job was to facilitate people for their problems and the companies problems as an employee of the HR department. There she couldn’t even do anything to protect some of the innocent girls that got harassed if the person harassing them had enough clout. Now she had a piece of power, and it not only felt good to have it, the power made her feel like she was going to need to use one of her toys tonight.

For Aiden that little bit of affection when he felt so low made him feel warm, that she cared, that all of this was just passing. He questioned himself asking if she actually made him do this was to pay some sort of penance for his behavior? Was she actually going to forgive him? She had said she wanted payback, and the addition of affection made him think the answer was yes. These thoughts swirled in his mind as he got up from the chair and lowered himself down for some blessed restless sleep.