Category: Transsexuals & Crossdressers Stories

A Job in the Theatre Ch. 14

by BothWorld©

Chapter 14 – Playing with the boys...

Paula couldn't believe how wonderful the car handled. They had the top down and were turning more than a few heads on the way to work. Paula loved it and so did Sarah. But the closer they got to the theatre the more nervous Paula became.

This would be her first appearance with real breasts. And now they were showing up in a Ferrari which was sure to start tongues wagging. Would people notice her breasts were real? If they did, what would she say? She found it curious that she hadn't given it much thought before then. She decided to put the thought from her head. For now, she would just cover up enough so nobody could tell. She knew that ultimately the word would get out, but she would deal with that later.

They walked into the theatre and Sarah headed off to the office. Paula headed for wardrobe to change into her costume. And who should be waiting for her by the curtains but horny little Billy with a nice bulge in his jeans.

"Hey Billy" Paula said stopping to talk.

"Hi Paula." She could see he was still so very shy with her. It dawned on her that she had asked him to shave last time. She was dying to find out if he complied with her wishes.

"Well Billy...did you do as I asked?" she asked slyly.

Billy's ears turned red as he nodded yes. She couldn't keep the grin from her face. She looked around, but they were alone. She pulled his jeans out and drove her hand down to his crotch. Sure enough he was bald as a new born babe. Her grin turned into a smile as she pulled him back between the curtains. "I like a boy who follows instructions."

Once secured behind the curtains, Paula dropped to her knees and pulled his jeans down around his knees so she could give him a proper inspection. Billy watched as she ran her hand over his smoothly shaved crotch.

She grasped his balls and ran her tongue over them causing Billy to howl. "Do you like that Billy?" she asked knowing the answer. She did it again several times causing poor Billy's cock to dance with excitement. Then she took him in her mouth and slurped on his cock while she continued to massage those clean shaven balls.

He had spent hours debating if he should actually shave his pubic hair off. How would he explain his "condition" to anyone? He realized that if he didn't, there might not be a next time. Now he was so glad he did. This time was even better than last time.

She thought about the power she had over men as she felt his smooth crotch. She would reward Billy for doing exactly as she had asked. Who knows what else she might ask him to do?

She loved sucking his cock. Poor Billy was rocking back on his heels trying his best to be quiet while she was doing her best to make him moan. Billy was so freaking horny he couldn't stand it. The things she was doing to his cock were unbelievable.

He didn't think he could last much..."Ahhhhhhhh" he blurted before catching himself. He hoped no one heard him, but didn't really care. For at that moment he was filling Paula's mouth with cum.

But someone did hear. Helen heard something and stopped in her tracks. She turned and looked, but saw no one. She listened for a moment, but heard nothing else. Must have been her imagination, she thought, and went along her way.

Billy stood there frozen with his pants around his knees. He had heard Helens heels clicking on the floor just before his orgasm. That would have been his job for sure. They needed to do this someplace else next time, because this was just too...

Suddenly Paula's lips were on his, then her tongue, then all that warm, thick sperm flowing into his mouth. He was powerless to resist her. There was just something about her, he thought, as he swallowed. There was so much of it. It didn't matter.

She pushed her finger against his lips, smiled and left.

Billy stood there with his pants around his knees, his cock limp, and his mouth dominated by the taste of cum. He was so glad he shaved his crotch!





Paula changed into her first costume, but still had almost an hour before the curtain call. She would have plenty of time to "relieve" Gary's nerves she thought as she walked next door.

Naturally Gary was pleased to see her. He wasn't sure if last time would be the only time or not. Of course he had thought about it way too much. Did he want it to be one time only? After all, they had really progressed past any thing they had discussed before. He was finding it increasingly difficult to explain her actions away as "part of the job." But who was going to turn down a great blowjob?

Paula watched as the makeup girl finished Gary up and left. Gary swung around in his chair presenting himself to Paula. She noticed the bulge in his pants and smiled. Rarely did she see him when there was not a bulge.

She sank to her knees and unzipped Gary's pants. Unlike Billy, she knew Gary would be shaved. She pulled his pants down marveling at her growing list of shaved groupies all of whom were supposedly straight. She took Gary's cock into her mouth and proceeded to deliver her second blowjob for the day.

Gary loved the way she sucked his cock. She was simply the best he had ever experienced. He felt himself growing closer to orgasm. Would she make him swallow his cum? It had been so nasty, so perverted last time. The very thought pushed him over the edge and he exploded in her mouth.

He always had such a powerful orgasm with her. Coming back down to earth he focused on Paula. Was she going to do it? Was she going to make him swallow his sperm? He watched intently as she released his cock. He could see driblets along her lips. She was keeping her mouth closed. Was that because it was filled with cum?

She looked him in the eye. It was a devious look. His eyes kept darting back to the sperm on her lip. She rose to her feet. Now she was standing between his legs, towering over him. He could feel the last drops dripping from his cock.

She moved her hand behind his head, grabbed a handful of hair, pulled his head back gently, forcibly. He was staring up at her, up at her mouth, the sperm along her lip. She gazed down upon him. She so owned him.

She reached up with her other hand and worked her fingers inside his mouth. At first he thought she wanted him to suck them and started rolling his tongue over them. But that's not what she wanted. She stretched them out between his lips indicating that he should open his mouth. He did as she wished. She pulled gently on his lower lip indicating he should open wider. And he did.

He watched as her eyes darted to his open mouth...as she opened hers. His eyes went to her mouth as cum started drooling of hers falling straight down into his. He watched as more and more sperm flowed from her mouth straight into his. There was that taste again. It was all so wrong, so wonderful.

Her eyes went to his, saw the erotic haze that covered them. Yes, she owned him. He had never felt more submissive in his life as he sat there, mouth stretched wide open, being fed his own cum.

She stared down at his sperm covered lips as he swallowed the last little bit like a good little boy. She took Gary's hand and pushed it up her skirt and watched Gary's eyes as he felt his very first cock.

Gary was stunned once again. He could feel his face flush. It was so different feeling someone else's cock! But there it was, hard and throbbing.

She held his hand firmly against it until he took over. That's right little boy, play with my cock. He started massaging her much like she had been doing to him for the last several weeks.

It was much easier with her standing there in that cute little skirt. And the silk panties made it something more feminine. What he saw was a girl and that's what he wanted to believe even though he was playing with a hard cock! So many thoughts went through his mind. The things she made him do were so wrong. Why did he always find them so exciting?

She could see the thoughts running through his mind. She was in his brain now. Her cock was in his brain. She pulled his hand off and smoothed out her skirt. She looked him in the eye, "Try not to think about that tonight...later...when you are lying in bed...all alone." She turned and left.

Thirty minutes later the curtain went up. Paula was beguiling as ever. Gary was like a deer in headlights.





"Did you notice anything strange about Gary this evening?" Sarah asked later that evening sipping her wine on the couch across from Paula.

"Well, he did seem a little preoccupied" Paula said with a straight face. It was one of Gary's worse performances and everyone knew it. They just didn't know why. Of course Paula did but was not about to admit it. "I'm sure it's nothing. Everyone has an off night" Paula said smiling into her wine glass.

The phone rang and Paula answered it. Of course it was Ted.

"Great show tonight" he said, "although Gary seemed a little lost."

"Yes, we were just talking about that. Poor guy had an off night. And how are you doing Mister?"

"Well to tell the truth I have a slight problem. But I think you can help me with it."

"Oh really? That sounds interesting."

"I have a guy in town and we just finished up a deal we have been working on all week. Now it is time to celebrate. And I was thinking to myself, who could help us celebrate better than Sarah and Paula."

"Mm...is that right?"

"To tell the truth I have been bragging about you and now he is dying to meet you."

"Is he now?" Paula said. This was it. Sarah said it would be coming.

"I have known him for years. But here's the problem. He is very quiet. Hardly says a word. You are just who I need to entertain him."

"Entertain him? Tell me...how much entertainment are we talking about? I don't want the poor thing to be too exhausted if you know what I mean. For instance...I don't want to take him to the academy awards if all I am allowed is a movie and popcorn."

Ted laughed into the phone. It was never a dull moment with Paula. "You may take him to the academy awards...if you so desire. I'm sure he would love that. But save the Oscar for me."

"Whatever you say handsome."





Gary lay in bed staring at the ceiling. His performance had been completely amateur. And it was all because of Paula. Every time he laid eyes on her he thought about her stiff cock inside those silk panties. It was all so wrong. He remembered how she had throbbed in his hand. She said not to think about it. But how do you forget something like that?

Now he was trying to go to sleep, but it was impossible. His cock was so hard. He wrapped his hand around it and started jacking off. It was the only way he would get any sleep. The more he pulled on his cock, the more he thought about hers. He still couldn't believe he did it. But it was so damn exciting. She literally throbbed in his hand.

She was the most confusing lover he had ever had. And there it was. Lover. His current lover was a woman or a man, or both, he was no longer sure.

The things they did were so gay. But she denied it, said they weren't gay at all. It was just something that happened, something they were doing for their jobs. But she was sucking his cock now. Isn't that gay? And she fed him cum, his cum. Isn't that gay? And now he was playing with her cock. That had to be gay.

"SHIT!" he screamed covering his fingers with sperm. Once it was completely over, he raised his hand to his mouth. He licked his fingers thinking how he was jacking off two, three time's day and swallowed every drop. And it was all because of her. It was all so wrong.





To be continued...

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Written by: BothWorld

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Story Tags: transformation, feminization, panties, gay swallow, gay blowjob

Category: Transsexuals & Crossdressers Stories