tagTranssexuals & CrossdressersA Job in the Theatre Ch. 05

A Job in the Theatre Ch. 05


Chapter 5 - Day two with the cast...

The next morning Paula awoke very aroused. Sleeping in the satin gown all night had kept him hard and throbbing for the entire night. This was now the third night in a row. He quickly removed his throbbing cock and stroked furiously. He came less than a minute later. He wiped himself clean with a tissue and let out a deep breathe. He couldn't remember the last time he masturbated so much.

He went into the bathroom and proceeded to shave his entire body once again. At first he thought it was going to be a real hassle. But doing it the second time was much easier and made his body tingle just like that first day. He had never been hairy, which had always bothered him as a man. It was a real plus now that he was dressing as a woman.

Feeling quite emboldened, he selected a very feminine bra and panty set with matching garter belt. Pink with bows and cute little ribbons everywhere was just what he wanted to compliment his extremely feminine mood that morning. He felt his breath catch as he slipped the bra on and fastened it behind him. His eyes were drawn to the mirror as he slipped his breasts inside. He loved the way his nipples were always hard and just slightly protruding. He reached up and gave his breasts a squeeze. They were just soft enough to feel very real.

The panties were nothing more than a thong that barely held his cock. He didn't think twice about his red toenails as he slid his feet into the sheer stockings. The garter belt featured a little pink lace skirt with pleats. It was so pretty. He wasn't used to pretty clothes. Maybe that was it? Whatever it was, he liked it.

Sarah ducked her head inside his room to ask a question and caught him wiggling his hips playfully at his reflection. "My...that is beautiful...and very sexy. You look good enough to eat" she said staring.

"Thank you" Paula said in his female voice with a cute little blush filling his cheeks. For the slightest of moments he felt embarrassed from being caught. But that was quickly replaced with feeling desirable.

Sarah was surprised at how good Paula looked in his underwear. She had not been kidding when she said he looked sexy. She couldn't see, but guessed his little cock was quite hard. She had been so taken by his sexy look that she forgot what it was she was going to ask.

He selected a nice pink blouse made of some fuzzy material that was nice and soft for his top and lovely pink and black skirt. Of course, he wore a nice pair of heels to compliment his legs. Mustn't forget that, he thought. And while looking at himself in the mirror, he decided to leave the first button undone, as it looked much sexier. He rolled his shoulders making his breasts stick out and felt his cock throb with pleasure.

Paula and Sarah entered the theatre that morning and Paula was instantly aware of the stagehands staring at him. Now they knew he was a man dressing in woman's clothes, but they stared anyway. Paula could see them making remarks to one another. However there was one who ignored the others and stepped away from them.

Paula threw his shoulders back, thrust his breasts out and headed right for him. The closer he got, the more nervous the guy appeared. Paula continued to look him right in the eye as he approached. The others realized that he was ignoring them and suddenly felt rejected. He gave the one guy a great big smile and said, "Good morning handsome" in his slow, sensuous female voice. The guy nearly lost it. The others made fun of him, but they clearly wished it had been them.

Paula learned quickly that wearing something sexy really got you noticed. He also learned that he liked making guys horny. It was fun to tease them, make them nervous. Only a good looking woman could do such things. And he liked being a good looking woman.

Then Paula saw Gary. He could tell that things had changed between them. He noticed the way Gary looked at him now. He could see it in his eyes. Paula hadn't had a chance to speak with him the day before. He wanted to make sure everything was alright and cornered him by the stage stairs.

"Hey Gary, how's it going?" he asked. He was using his male voice which sounded strange to Gary after a week of hearing something completely different.

Gary found it hard to make eye contact. He was obviously feeling guilty about something. Paula assumed that he had indeed spent the night jacking off as Sarah suggested. And it was pretty obvious that Gary had been thinking about him.

"Hello Paul." Gary's eyes traveled up and down the pink fuzzy top that Paula was wearing. He tried to hide it, but Paula could tell he liked it. "I'm not sure how to say this...but I wanted you to know...about yesterday and all...well, I was hard too" Paula said honestly.

Gary's shoulders immediately loosened up and a faint smile crossed his face. Paula knew then that speaking to him was the right thing to do.

"I don't know what got into me" Gary said looking around to see if anyone could hear, "I just got horny. Sorry man...I guess it just happened."

"Yeah, pretty weird" Paula said finding it hard now to look at Gary. "But it wasn't that bad, not really. I've never touched another guy before." Paula found her courage and looked at him, "The things we do for a living, right?"

"Right" Gary said relieved. He had spent the night jacking off and feeling pretty weird about it. He was glad to hear Paula wasn't gay. Somehow that made it better. He wasn't gay either.

Now it was Paula's turn looking around to see if anyone was within hearing distance. It was just the two of them. "Of course I will deny it, but I couldn't wait to get home and jack off."

"Wow, me too" Gary said without thinking.

"Man I came all over the place!" Paula said giving a quick smile.

"Man, no shit. Me too."

A moment passed in complete silence. But it had been a bonding moment.

"Just between you and me...right?" Paula asked in a serious tone.

"Right!" Gary said feeling better now knowing his secret was safe.

That night he wore the sexiest see-through black baby doll trimmed in white lace that was split in the middle and stopped just short of his crotch. His panties were see-through as well, held by two dainty little strings tied in bows at the hip and trimmed in matching white lace.

It did nothing to hide Paula's manhood. Sarah stole several glances at his bald crotch and thought how cute his diminutive size looked held gingerly behind the see-through frills.

She watched as Paula moved so sensuously from one room to the other, complete with feminine gestures, and thought how relaxed he had become in his new role. It occurred to her that he must have been really enjoying himself. He was certainly putting in much more effort than was necessary. She watched as he curled up on the couch to paint his toenails and wondered; could this be the same man who complained a few days ago about frilly pink panties? Not hardly!

She watched as Paula got up the next morning and slipped into a sexy pink bra. His cute little cock hung uncovered and it seemed to her to be thickening. He followed with matching garter belt and stockings. He pulled the stockings up in the most sensual way. By the time he was through Sarah could see his cute little cock pointing straight up. She watched as he expertly tucked in between his legs and pulled his panties tight. Poor thing, she thought, even hard his cock couldn't have been more than four inches.

She continued to watch as he slipped on an extremely tight skirt that was a good six or more inches above the knee. Sarah thought the skirt was quite short, if not problematic. She was sure she would never wear anything so short. He slipped on a corset top that matched the skirt followed by a pair of heels with straps around the ankles. It occurred to her that she had not seen him wear any other style of heels that since this began. She also noticed that his eye shadow was a little darker than usual too.

They made their way into the theatre and said their hellos. Paula and Gary exchanged looks and Sarah could sense a private conspiracy between them. She wasn't sure what that was about, but decided to let it take its own course.

The rehearsal started with scene five again and both boys performed magically. Paula didn't have the slightest hesitation massaging Gary's cock under the spotlight. And Gary rose to the occasion as if on cue.

Sarah was quite pleased. Everything was going according to plan.

"OK everybody, that's a wrap. Have a good weekend and we will start again Monday" Sarah announced. She could not be happier with the way rehearsals were going. Paula's transformation was definitely the turning point and had a profound effect on the rest of the cast. Living as a woman had done the trick.

"Paula, could I have a word with you?"

Paula walked gracefully to a chair next to hers. He sat down and she noticed that his skirt was so short that there was no way of hiding his panties from her view. Of course the first thing she wondered was if he was hard.

"You were absolutely perfect today! You have really been great this week. And to celebrate, I have a surprise for you" she said. Paula was glad to hear his hard work was paying off.

"Oh how sweet" Paula responded sounding appropriately feminine.

"You and I are going out on a date tonight. I thought it would help you get a handle on scene six." That scene was Paula's worst. It required him to kiss Gary and he always tried to avoid it during rehearsal.

"With men?" he asked in horror suddenly using his male voice. He quickly realized how strange it sounded and unconsciously darted his head in both directions to see if any one heard.

"Well of course with men, silly! Oh Paula, don't be such a prude" Sarah said using his female name. Sarah always used it when it was just the two of them. "It will be a perfect time for you to explore and get comfortable with your feminine sexuality. Now don't worry, they both are good friends, and whatever happens will be just fine. I will introduce you as a woman... so the rest will be up to you."

Paula was hesitant. It seemed like such a big move. Sure, if the truth were known, he had had fun flirting with some of the guys there at the theatre, but this was different. This was a date for god sakes. And they wouldn't know he was a man!

Hmm...they wouldn't know he was a man. He thought about that for a moment. Suddenly the idea appealed to him. This was his chance to really play it up big. He thought about the delivery man and what a kick that was. His cock throbbed unexpectedly. Yes, this would be a true test of his abilities. He suppressed a smile.

"OK, I'll do it" he said turning his head before Sarah could see the excitement in his eyes.

They went back to Sarah's house to get ready. Sarah could see that he was a bit nervous and poured them both a drink. Sarah was excited too, but for a completely different reason.

Paula looked at the clothes she laid out for him and took a deep breath. There was a black lace bra with French cut panties to match. Next to that was a lacy garter belt with sexy black seamed stockings and black high heel shoes. And yes the heels had straps that went around his ankles just as he liked. But that was nothing compared to the short, skimpy evening dress.

So this was what a date was like, he thought. Well, from the female side at least. He hoped he could pull it off. He was nervous, but excited too. He did his best to block the obvious from his mind and focus instead on that sexy lady of his and what she would do. Surely that path would provide more fun.

Paula took a big sip of his drink and proceeded to take off the clothes he had worn to the theatre. He didn't think twice about being naked in front of Sarah, not after all they had been through that week. She sat calmly on his bed wearing nothing but a pair of panties. They were just as close as any two women could be. Besides, they were getting ready to go on a date together!

He put on the French black lace bra first and slipped in his "breasts" to fill out his form. He gave them a good squeeze to make sure they felt right. They did. Next was the lacy black garter belt that snapped around his waist. He took the first black silk stocking and gathered it in his hand, pointed his toe and then slipped his foot inside and worked it up his leg perfectly snapping it into place.

By the time it was secured, his penis had grown completely hard and stood straight up from his lap. Sarah noticed, just as she had noticed the times before. This was the same man who was completely repulsed with the whole idea of dressing as a woman. Ha! My how things had changed she thought. Sarah stared at his cute stiff cock as he rolled the other stocking up his leg and fastened it.

She continued to watch as he slipped into the French cut silk panties and how they hugged his hard penis. She could see every detail of his cock as it stretched the silk tightly. It was all she could do not to reach out and grab it. The sight of his hardness captured within the soft feminine trappings enflamed her. That image would dance in her head for the rest of the evening.

"Would you like some help with that?" she teased watching him tuck his erection between his legs and pulling the delicate panties smooth.

"Ha, ha, ha" Paula said mockingly. He did not take offense at her teasing.

She helped him into the dress she picked for him to wear that evening. Not only was it comprised of slinky material that hugged his body and felt delicious, it also was extremely short and terribly sexy. Sarah knew it would drive the men crazy and that was exactly why she picked it. Paula would be the belle of the ball this evening and Sarah couldn't wait to see how he would handle all that temptation.

"Oh Sarah...its lovely" Paula said looking in the mirror. "You don't think it's too much?" He was certain that his garter straps would show with the slightest of movements in such a short dress. He could feel his face flush underneath the makeup. He had never felt more sensuous in his life. He felt naked and exposed even though he was fully dressed according to Sarah. And there was something else. He felt totally desirable. He looked so hot and sexy. Everyone would notice him tonight.

Sarah walked up behind him, her naked breasts pressing against his back. "It's never too much my dear. Remember that. You are going to drive those boys crazy" she said. Paula couldn't stop thinking about her lovely breasts pressed against his back. He loved her casualness walking around the house. He saw them all the time, but that didn't compare to feeling them pressed against his back.

Paula shot her a smile in the reflection and asked, "Do you really think so?"

Sarah was sure he didn't realize what was about to happen. He had never experienced a horny male trying to get in his panties. He had no idea how persuasive they could be. So far his experiences had been within the safety of the theatre. Tonight would be vastly different.

"I know so. The men will be all over you tonight!" she said taking a sip of her drink.

Paula looked at his reflection again. Sarah was right and he knew it.

For half a second he felt totally overwhelmed. How did things get so crazy? But then he took a deep breath. He thought about the power he would have over them this evening and couldn't wait. He was going to have fun tonight. He would be that sexy lady that lived in his mind.

Sarah handed Paula her bra. "Can you help me with this?"

Paula took the bra and stood behind Sarah. Now it was Sarah standing before the mirror. Paula put the bra around her and brought it up to her lovely breasts. He had been staring at them for over a week, but he had never touched them. He slipped the bra cups over them and pulled the bra tight and snapped it together. Almost as a reflex, he ran his hands over her breasts to make sure the bra fit correctly. Of course it did. Her breasts were flawless and he was jealous of the way she flaunted them.

"Thank you dear" Sarah said with a sly grin looking at his face in the mirror's reflection.

Paula felt his cock throb between his legs. They had grown much closer over the last week. Paula began to wonder if sex between them might be possible. He got the impression that Sarah was thinking about it too.

She stepped into a slinky little black cocktail dress and pulled it up over her breasts. It featured a daring slit up one side that was definitely risqué. Paula was not used to seeing Sarah decked out, but she wore it well.

Once zipped, she cupped her breasts while staring in the mirror. "Yes, I still have it. And I am going to use it tonight."

Paula just smiled from over her shoulder.


To be continued...

Hope you enjoyed the story. Please remember to vote. Your comments are welcomed.

Report Story

byBothWorld© 3 comments/ 66976 views/ 22 favorites
1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartUltimak, tdkb1916 and 20 other people favorited this story! 

by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

There are no recent comments (3 older comments) - Click here to add a comment to this story or Show more comments or Read All User Comments (3)

Add a

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

Refresh ImageYou may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: