A Job in the Theatre Ch. 02

NOTE: This story contains many chapters featuring a few twists along the way. The twists are more delicious when you know the characters. There is steam coming your way. I hope your patience will be well rewarded.

Chapter 2 -- Becoming a woman - First Day

That Saturday he drove to the address Sarah gave him. He was surprised how nice the house was as he pulled into the driveway. Hidden behind a large hedge, the house sat on a circular drive that curved right by the front door. Obviously Sarah was doing very well in her career. If only he could get his going, he thought.

He thought about what she had said, but didn't really have an appreciation of what it meant to live as a woman. But of course it could only help and he was prepared to do what was needed to keep the role.

Sarah opened the door to find Paul wearing a ball cap, tee shirt and jeans. That would be the last he would see of those, she thought. "Good morning. Are you ready for this?" she asked. Her tone was serious, but not condescending.

"Yes, I'm ready," he said.

"Good. Let's get started. Is that your truck?" she asked noting the eyesore in her driveway. What would the neighbors think, she wondered.

"Yes."

"I think it might be in the way there. There is a parking space behind the garages. Why don't you park it there?" She watched as he turned and headed back to towards the truck. She noticed the way he walked. It was very male. That would need some work. But at least he had a nice ass.

"Come right this way to the bathroom" she said in an authoritative voice when he returned. They had a lot of ground to cover and she wanted to leave no room for doubt as to who was boss.

They got to the bathroom door and Sarah handed him a pink razor. "Remove everything below your ears. Yes, that means everything."

Paul took the razor and stepped into the bathroom. Sarah closed the door behind him and he felt very alone. Well this was it he thought. Stop thinking and start doing.

He took off his clothes and stood before a full-length mirror. He had never shaved his pubes before and wasn't really sure how best to go about it. He decided to dab his privates with water and just go for it. The deed took little more than a few minutes and he found himself looking at a bald crotch for the first time in his life. Not only that, but his legs were totally bare too. He didn't need to shave his chest, it held no hair. It was something that always bothered him in the past, but today it was a plus. It was different, very different. He realized it would be a while before going on another date or heading to the gym as he was not about to explain his condition to anyone.

He immerged from the bathroom with a towel wrapped around his waist. He sat on the edge of her bed and watched without comment as she went through her drawers picking things for him to wear. "These should fit you well enough," she said, dropping a pile of panties on the bed beside him. "At least they will do until you buy some of your own. Of course, I can help you with that."

"Is this really necessary?" Paul asked picking up a pair of skimpy pink panties, "I mean, can't I just put on a dress and a wig? That's all people will see."

Sarah rolled her eyes. She half expected this. "Yes, it is necessary. It's not what people see, it is what you feel. The whole idea is for you to become a woman. And women like feminine, sexy things. And so will you mister. Put them on!"

He held the panties in his hand. They were made of silk and trimmed in lace. And they were pink! He wasn't sure he was through arguing, but knew he would loose. He looked at her expecting her to leave the room so he could put them on. But he could see from the look in her eye that she had no intention of leaving. She wanted him to put them on, right then, right there, with she watched.

Paul took a deep breath and dropped the towel exposing his clean-shaven body. Sarah stole a quick glance at his bald cock and was very pleased with what she saw. His cock was rather slender, she thought, and not particularly long, but looked very cute in its present state. The important thing was that he had followed her orders explicitly.

He quickly slid the skimpy pink panties up his legs into place complying with her demands.

At first the skimpy garment bulged out at the front in a very unfeminine manner, but at Sarah's suggestion, he tucked his penis back between his legs and managed to achieve a reasonably acceptable feminine profile. And it was not a minute too soon. He could feel himself responding to the cool silk caressing his freshly shaven crotch.

Next Sarah handed him a bra and two silicon breasts. The cups of the bra were actually pockets made of shear material. She showed him how to slip the breasts inside the cup pockets, which held them firmly in place. Then she showed him what the bra looked like from the outside. The shear material was just enough to make the breasts look real with the nipples of the breasts slightly protruding, just as they would be for a real woman. It was necessary she explained when someone, and you never knew when, might be sneaking a peek down his top. This way they would see exactly what they expected to see. He slipped the bra on and adjusted the straps until it felt comfortable.

She nodded her approval and handed him a garter belt trimmed in roses, which matched the panties and bra. Now any woman knows you put on the garter belt before the panties. It makes it easier to go to the restroom. But Sarah worried Paul might become excited sliding on the nylon stockings. It would be an embarrassment she didn't think he would recover from. No, she thought, it would be best to have his penis safely tucked between his legs and out of sight just in case. There would be time later for him to realize the correct way.

He fastened it around his waist and adjusted it so that it fit nicely on his hips. Feeling quite foolish, he picked up the stockings and tried pulling them up his legs. He was making a mess of it and Sarah stepped in and showed him the proper way while he watched. Then she handed the stockings to him.

He took the stocking and proceeded to do exactly as she had. Even though he still felt foolish, he did manage to get it up his leg and fastened to the garter belt. The feeling of nylon covering his leg surprised him. He would not have thought it would be so...so provocative.

Was it because his legs were clean-shaven or was it the feel of nylon against his skin? He didn't know, but felt a familiar stirring in his crotch. The very last thing he needed was an erection. What would Sarah think? He could feel his face turning red just thinking about it. He shifted slightly in his seat hoping it would obscure Sarah's view. He quickly put the other stocking on and fastened it as well.

Then he took the dress she had chosen for him and pulled it on over his head, reaching behind him to zip it up. The dress concealed his immerging problem and he was quite thankful.

"Try these on; they should be your size." Sarah handed him a pair of medium heels. They were plain black heels, not too high, and they were a perfect fit. They were very different from men's shoes to be sure. Everything about them was different. The one thing he liked was the elevation. They added a few inches to his height.

Paul found himself in a new world. The clothes he was wearing felt completely different than anything he had every experienced before. The skirt was very light; he could not even feel it upon his body. He wouldn't have known it was there if he could not look down and see it. It had a wispy hem with the top layer being see-through which added a certain thrill to it all. It dared people to look, enticed them really. Its length came just below the stocking tops making it very, very short.

He was struck with how naked he felt. While wearing men's clothes, you could feel the clothes against your body. The materials were heavy and strong. Not only did you feel clothed, your felt protected. When it was time to get to your cock, you had to first unzip the heavy jeans, and then dig around inside your cotton underwear through the hole that was provided. Even after you got your cock out, you still felt protected as most of it was still covered behind layers of clothing.

But this was completely different. The clothes were light and airy. You could not feel them against your body, not really. Not only was the skirt open at the bottom, it stopped just barely an inch or two below his cock leaving his legs completely exposed. There was no protection whatsoever. Getting to his cock presented no problem at all. All he had to do was lift the flimsy material of his skirt and pull down his silk panties and he was immediately exposed; cock, balls and everything.

Dressed as a man meant being covered and protected, his sexuality was covered by layers of material that obscured everything about it and did its best to hide its very existence.

Dressed as a woman meant being open and accessible; the whole purpose was to bring attention to his sexuality along with the idea of how easy it was to be had.

The difference between the two was never far from his immediate consciousness. He was constantly aware that he was exposed and accessible.

He took a tentative step. The material of his dress brushed sensuously against his thighs registering a whole new experience. He was completely aware of his undergarments. It was strange feeling something around his chest, not to mention the tight cut and feel of silk around his privates.

Sarah was right. This was much more then wearing a dress and wig. This was a completely new experience that touched every part of his brain.

He took a few steps and realized that he needed to perfect his balance with heels. He could not take his normal step. Wearing heels and a dress meant a much shorter stride. As a woman, he would walk slower and men would match his stride, not the other way around.

He strolled from one end of the room to the other getting his bearings. As he did he noticed the bulge of his inflated cock stuck between his legs. That caused him to walk slightly different making his hips sway a bit more pronounced. His "breasts" were just at the bottom of his field of vision and jiggled just slightly as he moved. He became fascinated with them and couldn't keep from glancing down every few seconds. He had the incredible urge to reach up and grab them, but knew better with Sarah standing there.

"You look great" Sarah encouraged him. He was turning out much better than she had hoped. His slight frame was a great asset and made the dress fit perfectly. His "breasts" really gave him a feminine curve. Together, it made a very convincing package.

And he had not complained once and she was most happy for that. She was prepared for some grumbling, but he did not utter a peep.

"Now I think its time for some makeup. That will make a huge difference. You'll see." Obediently Paul sat at the vanity. He was not a stranger to makeup being an actor, but makeup for the stage and makeup to be a woman were two different things.

She pulled his hair back away from his face. He paid close attention to every little thing Sarah said as she transformed his male features into softer, feminine ones. His eyes become more pronounced, his cheeks softer. He accepted the lipstick without comment. In a matter of minutes Sarah was satisfied with his new look.

Now that his face was quite feminine, it was time to do his hair. Fortunately Paul had rather long hair that he usually wore in a ponytail and Sarah was determined to do something pretty with it. She had a wig for him but didn't want to use it unless it was absolutely necessary. The wig would feel unnatural and she wanted Paul to feel as natural as possible.

She pulled out curlers and hair gel and went to work. Sometime later, she pulled the curlers from his hair and brushed it out carefully. The result was better than she had expected. Now Paul's face was framed in long beautifully curly strands.

"Just one more thing..." she said picking up a pair of tweezers. Carefully, she plucked Paul's eyebrows until they were quite thin and arched in the middle. The results were very feminine. Everything up to that point could be reversed, but not the eyebrows. Now Paul was committed whether he liked it or not. She hoped he wouldn't get mad.

"Now...come and see for yourself" she suggested.

Paul stepped over to examine himself in the full-length mirror. It was all there. His eyes were sexy and alluring. His nose and cheeks were soft and rosy and his lips glistened with lip gloss. His hair had nice long curls framing his face. Throw in his new bust line and sexy dress; there was not the slightest hint of male.

"Wow!"

If he had doubted Sarah's plan before, he now saw that it could work. He was surprised and strangely pleased to find that he made into a very attractive woman. He was drawn to the image in the mirror. He wasn't merely attractive; he was down right hot!

He turned each way to check his profile in the mirror. He had a reasonable bust, not too big as to draw undue attention, but certainly big enough to be desirable and provide the delicate feminine curves. His nipples were just barely noticeable under the fabric casually drawing the eye. His nice bubble shaped ass, which had always been firm, was now complimented by a nice smooth crotch. His shapely legs looked great in stockings. He noticed with a certain satisfaction that wearing heels gave his lower leg a convincing feminine appearance.

His face was soft and delicate. His eyes were particularly alluring, so alluring that he failed to realize the permanence of his eyebrows. His lips seemed bigger and luscious. He was drawn to his reflection. It was if it were someone else.

Then he turned with his back to the mirror and bent slightly at the waist to see just how far he could bend over without showing his sexy underwear. He couldn't help but notice how provocative his legs and ass was from this angle. He felt naughty and found that surprisingly enjoyable. "Well I don't look half bad," he observed smiling at his reflection. The fact was he thought he was a knockout. He wondered if Sarah thought so too.

Sarah pinched him on the butt and said, "You are simply beautiful. But, I don't think that voice will do, now will it?" Sarah said thrilled by how pleased he was with his new appearance. Paul gave her a knowing look and muted his voice and then tried a slightly higher pitch.

"It sounds forced. I know... try more of a hushed tone, something kind of sensual" Sarah suggested. He did and it was much better. "Great. Now dear, try a little different cadence, something a little slower." Again he took her suggestion and quickly produced a very feminine voice that sounded very natural and easy.

"Perfect" Sarah said standing behind him looking at his image in the mirror. Her eyes feasted upon her new creation. She reached around him and casually ran her hand over his breast and down his tummy. It was a caress more than anything and it was sexual in nature. Paul wondered if she realized what she had just done. "Yes...perfect" he said breaking the moment. He used his new feminine voice and Sarah was pleased.

So much to learn... And thus began his training. Sarah gave him instruction on seemingly every little detail of existence and he found it overwhelming. Everything was new, the way he walked, the way he talked, how he sat, how he smiled. Nothing was the same. They broke for lunch and Paul was feeling discouraged. There was so much to learn, so many things to remember. He felt less feminine than ever.

"Again dear, remember to sway your hips as you walk. Every man will be watching, so give them the show they are expecting. Women are always being watched, even when you don't think you are. That's the way it is for women, get used to it. Good, good. Now...stop and peer over your shoulder. Look at me. Good. Now, I am a man and I am staring right at you. You just caught me staring. What do you do?"

"I smile gently, raise my hand to my hair and twirl a strand around my finger."

"And stick your chest out!" Sarah yelled making a point by placing her hands underneath her own boobs and squeezing them together while holding them up. She had great boobs, perfectly shaped. He loved the way she was practically offering them to him. In any other situation it would be improper for him to stare, but under the circumstances, it was expected.

"And stick my chest out" Paul said thrusting his fake breasts forward. "I'll never be able to do this," he said dismally still practicing his new voice. Sarah had to remind him for what seemed like the millionth time to smooth his skirt under his thighs as he sat down.

"Of course you will. Being a woman is all about attitude. Being a woman is being sexy. Being a woman is using your feminine charms to be alluring and seductive... Being a woman is to be desired. Now that is the attitude I'm talking about" she assured him. "The problem at the moment is that you are still a man trying to act like a woman. You have to relax and be a woman... in your mind. Then those small gestures will come naturally."

But Paul was frustrated. He wanted to do this, he really did. But there was just so much.

"I know...here, have a seat" Sarah said patting the chair. Paul sat down and she stood behind him and put her hands on his shoulders.

"Now...close your eyes...relax." Sarah waited until Paul started to relax. She could feel the tension in his shoulders start to dissipate.

"Good. Now...I want you to take your hands...and place them in your lap. I want you to feel the nice smooth silk of the dress you are wearing." Paul ran his hands along his dress and could feel the soft sexy silk under his fingertips. He certainly was not used to feeling that.

"Good. Now see how nice that feels?" Sarah asked. "Now, I want you to put your hands underneath your dress...to your legs...and feel the cool nylon that covers them."

Paul slipped his hands underneath his hem and placed them atop his nylons. His cock throbbed with excitement as he felt the lace tops, the garter strap. Sarah noticed a change in his face.

"Now dear...ran your hands up your body, slowly...slowly...feel your breasts...feel how soft they are..."

Paul ran his hands to his breasts. They were soft and squeezable. His fingertips grazed over the nipples sending thrills to his cock encased behind the silk panties.

"I want you to think back...think back to the sexiest woman you have ever seen. I want you to remember everything about her...her hair, her smile...that look in her eye...those beautiful legs...those soft breasts. Now, I want you to become that woman...yes, you can do it...just loose yourself in the part, dear. That's right, just let go. Become that woman of your dreams. Stop thinking like a man; stop identifying yourself as a man. Now you are her...you are that beautiful, sexy woman."

Sarah paused to let that sink in. She watched as the look on Paul's face changed. His body shifted slightly and she could tell that it was working.

"You are the woman that every man wants, every man desires" she whispered in his ear, "when you don't know what to do...just think of her...and do what she would do..."

She watched as the slightest of smiles crossed his face. Yes, he got it.

They practiced for several more hours that afternoon with Paul doing everything over and over again. Although he didn't feel totally confident, he did recognize some improvement. He was getting used to his heels, had finally learned how to sit and his new voice had become almost effortless.

*

To be continued...

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