A Job in the Theatre Ch. 03

Chapter 3 -- The Delivery Man

Paul nearly jumped out of his skin when they heard the doorbell ring. "Who is that" he asked panicked.

"Just calm down. I'm not expecting any guests. Oh, this is a prefect opportunity. I want you to answer the door. It will give you a chance to show off all that you have learned today."

"You must be kidding!"

"I most certainly am not. Soon you will be doing this every night. You had better get used to it Missy."

She had a point. After all, she had a lot of money riding on his performance. He smoothed out his dress and headed for the door swaying his hips generously. He took a deep breath and opened the door.

There was a man standing outside. In his newly acquired female voice with the slow sensuous cadence Paul asked, "May I help you?"

The guy scanned him from head to toe and back again. So this was what it felt like to get checked out. Paul watched the man's eyes and could tell he was impressed. The guy thought he was hot! Paul got a real charge from that. He was making the guy horny. He liked that a lot.

"Well..." Paul asked interrupting the guy's drooling stare. The guy realized he had been caught red handed. His ears turned red with embarrassment. Paul knew the feeling well. But that didn't stop him from enjoying the guy's discomfort.

"Oh...yeah...uh, delivery for Sarah Patton. It comes to $15.00."

Paul used the opportunity to lean forward flashing a bit of cleavage combined with a sexy look and said, "Wait right here, honey. I'll be right back." He closed the door behind him and leaned against the wall. What a rush that had been!

"Who is it" Sarah asked.

"It's the delivery man. He has a package for you" Paul said trying to contain his excitement. It had been his first true performance as a woman and was a total success. "He wants $15.00."

Sarah turned to get her purse. As she fished the money out Paul gushed, "He has no idea. I totally fooled him. You should have seen him checking me out!"

Sarah was happy to hear Paul so pleased with himself.

"Really? Great. Here's the money. Now, let's have some fun. I want you to flirt with him" Sarah encouraged.

Paul's face lit up. "OK, I'll give it a try."

He took a deep breath and focused. He put his hands on his breasts and then ran them down his silk encased body feeling incredibly sexy. He reminded himself that this was what the guy was seeing. He turned and opened the door.

He looked at the guy and stared sensually into his eyes. It was like putting a spell on him. The guy stood there hopelessly frozen. Just as Paul stuck his hand out to give the guy the money, he dropped it.

"Oh, I'm such a mess" he said in his sensual new female voice not moving an inch to retrieve it.

"Don't worry. I'll get it" the guy said and bent down to pick it up. As he did, his head was barely an inch from Paul's long legs. And just as Paul had hoped, the guy took his time appreciating his nice high heels, nylon covered legs and sexy bust as he rose to his feet.

Paul was embarrassed by the tingle the guy's gaze sent to his crotch. But he most certainly got a charge from it and wished he had done more. When the guy looked up Paul was looking right at him with a sexy smile and a knowing look.

The guy's ears turned totally red. "Th..thank you ma'am" the guy said and turned before he got himself into any more trouble. Paul closed the door behind him and fell against it. He instantly replayed the scene again in his mind just to make sure. And yes, he totally got away with it.

It was just the boost Paul needed. His hard work was paying off. And it was fun, too. He loved teasing that guy, loved the look on his face. Playing the vixen was fun. Being a woman was different. It was true, they will always be watching. He knew that now.

Sarah suggested a nice stiff drink to celebrate and Paul thought that was a wonderful idea. He sat back on the couch and sipped his drink thinking that this might not be as bad as he had originally thought.

And there was another thing he noticed. Now that he had been dressed that way all day, his female clothes didn't seem so strange. Oh they still made his spine tingle with every step he took, but that part he liked.

Later that night Sarah came into his bedroom with three different nightgowns. She was wearing one herself. Hers did very little to hide her ample chest and Paul could clearly see her breasts with the tiny protrusions in the center and felt his cock begin to stiffen within the panties he was wearing.

"What is this?" Paul asked looking at the nightgowns.

"I brought you something to sleep in. Basically, any one of them will do. They are all very nice don't you think? Which one do you want to try?" she asked holding them out for his inspection.

Paul doubted if this was really necessary, but decided on the pretty satin one.

"Good. Now it is probably a good idea to leave your bra on so the nightgown will fit properly. You have boobs now, so you might as well get used to them" she said with a smile. She knew he was still wearing his panties as he had nothing else to put on.

She watched as he slipped the nightgown over his head and pulled it in place. "Yes, that looks great on you. Let's share a glass of wine before we go to bed" she said with a smile.

"That sounds good" Paul responded.

They went into the den and Paul sat on the couch as Sarah poured them both a glass of wine. Paul couldn't help but noticed Sarah's lovely figure accentuated by the sexy nightgown she was wearing. She handed him a glass and sat across from him on the other couch.

"I bet my delivery man is home right now playing with his cock. What do you think?" Sarah asked with a sly grin. Paul was somewhat surprised by her bold assessment. Paul smiled and took a sip of his wine. Under normal circumstances he would be sipping a beer, but ladies don't drink beer, they drink wine.

"And it's all because of you. I could see he was quite impressed with you, my dear" Sarah continued.

"Do you really think so?" Paul asked knowing full well that he had been.

"Yes, of course he was. Did you notice the bulge in his pants when he left?"

Now Paul had missed that little tidbit. "No! Did I make him hard?" Paul said surprised, but very pleased. Sarah noticed his delight.

"You sure did honey. You need to get in the habit of checking a man's crotch, my sweet. It will tell you everything you need to know, trust me. I'm sure he is whacking his cock right this minute thinking about getting into your cute little panties."

Now Paul liked that thought very much. He could just picture the guy's cock in his hand as he erupted all over his fingers. How many times had he done that exact same thing? Yes, next time he would really play it up.

His eyes strayed across to Sarah's breasts which sent a tingle straight to his crotch. He could see them perfectly from where he was sitting.

Sarah finished her wine and gave Paul a knowing smile.

"Good night, dear. Sweet dreams."

Had he just been caught? He couldn't really tell. If he had, she didn't seem upset.

Paul retreated to his bedroom. It was decorated in pinks and whites. He got into his big canopy bed and pulled the covers over him, but the feel of satin that caressed his body dominated his senses. The more he tried to ignore it, the more prominent it became. His cock, already half hard from Sarah's lovely breasts, grew inside his panties stretching them even tighter. He reached down and pulled it from between his legs giving it room for the first time that day.

He tossed and turned, but that only amplified the satin caress against his body. His cock began to throb and it became readily apparent that he would not be able to sleep in this condition.

He released his cock from his tight fitting panties and began to stroke, just like he imagined the delivery man was doing. As his excitement rose, his mind traced back to earlier in the day when he pulled those nylon stockings up his legs. In the privacy of his bedroom he allowed himself to bath in the excitement he denied earlier.

Thus relaxed, he allowed himself to enjoy the feel of satin that encased his body. He just loved the way satin felt against his skin. Then it struck him. He quickly took a handful of his satin nightgown and wrapped it around his cock. The pleasure was immediate. He stroked his cock once tightly using the satin and it was glorious. Oh god, this was wonderful! He pumped several more times losing himself in the distinct feel and texture.

His climax soon followed and was very intense. He had removed the satin just in time before making a mess. He pulled a tissue from the nightstand and wiped himself clean. He stuck his deflated cock back into his panties and rolled over to sleep. It had been a long, but satisfying day.

The next morning Paul woke up slowly. As he lay in bed, he became aware that he was wearing a satin nightgown and a bra. He also became aware that his erect cock was sticking out the top of his satin panties. It was crazy, but a glorious kind of crazy.

His cock was throbbing as it had all the previous day. He couldn't very well walk into the breakfast room sporting an erection. How embarrassing would that be? And there was no way he was going to be able to tuck it between his legs the way it was.

He faced the mirror and hiked his satin nightgown up revealing his poor erection sticking out the top of his satin panties. What a sight that was! Although the panties felt wonderful, he was not used to seeing himself in them. He was bombarded by conflicting thoughts and emotions.

He lowered his panties allowing his cock to spill free. He stared at his clean shaven crotch. His cock jerked with excitement. He slipped his hand around it and squeezed. He was so fucking horny. He loved the feeling of his warm, throbbing flesh between his fingers. He pulled hard on it. God that felt so good.

Then he remembered the new little trick from the night before. He opened his eyes and watched in the mirror as he wrapped his cock with the satin from his nightgown. He could see every detail of his cock outlined in the sensuous satin. Man, this is kinky he thought, but it felt so good.

He ran his fingertip over his cock teasing the head. His legs started swaying back and forth from the sensual caress. Kinky or not, it was the best thing he had ever felt. He started stroking himself loosely at first feeling the satin caress. Man that was good. Then he squeezed tighter and really started stroking. The satin was stretched tightly against his cock and it was just too much.

He was able to remove the satin just in time before he started spurting wildly from a most outrageous orgasm. When it had subsided he realized he had sprayed cum all over the mirror and floor. He just held his deflating cock trying to catch his breath. He couldn't remember the last time he came like that. He cleaned up the mess with a new appreciation for this little trick.

He walked into the breakfast room to find Sarah enjoying a cup of coffee. He fixed himself a cup and walked over to fill hers at the table. The gesture offered him the perfect opportunity to check out those lovely breasts once again.

From this angle, he could see them in their entirety. Her breasts were perfectly shaped. They were simply magnificent. He wished he could reach right down and caress them, stick them in his mouth, tongue those hard nipples. He loved to play with breasts. Then he caught himself. If he wasn't careful, he would get caught just like the delivery man.

"How did you sleep last night, dear?" she asked feeling his eyes upon her.

There it was again. Dear. He was not used to being addressed that way.

He was not about to tell her how the nightgown drove him crazy, how he spent the first part of the evening jerking off so he could get to sleep. Nor was he going to tell her about the climax he had just experienced so he could get his cock back into his panties so he could come to breakfast.

"Good" he said sweetly using his female voice.

"Well, we have a big day ahead of us" she said. "I thought we would buy you some clothes of your own. There is a place I go to all the time. They know me there and you can select some really pretty things. They really have a fashion sense about them and I know we will get some really great clothes for you."

"Well, I'm not sure how to say this. But...I am really kind of short right now in the money department."

"Oh, don't worry about a thing, sweetie."

There it was again. It was sweetie this time.

"The play will pick up the cost. The important thing is that you get what really works for you. I want you to feel comfortable in your new clothes. More importantly, I want you to develop your own look as a female. After all, that is what this is about, right?"

"Yes, I guess you have a point" Paul said reluctantly. His mind was racing. They were going to a store? How was he going to pull this off?

The shopping trip Sarah knew the physical transformation was one thing, but the way it made him feel was another. Paul needed to experience people seeing him as a woman. The delivery man was a good start, but he needed to see what it was like to have unknown eyes undressing you as you walked down the street. That was the life of a real woman and Paul needed to experience that. Paul felt nervous about the shopping trip. It was one thing to wear female clothes on a stage, even around Sarah's house. But wearing female clothes out into public was something altogether different.

Sarah sensed his nerves and suggested a nice white pinned stripped suit that hung in her closet. It was pretty conservative in cut and came an inch or two below his knees. She hoped this would make him feel less noticed and therefore more comfortable. It was with growing apprehension that he followed Sarah out of the house.

Their first stop was to buy him a handbag. "A woman never goes anywhere without her handbag, so you won't either" she told him. Paul readily agreed to this as he had quickly found that while wearing a dress left nowhere to keep his money or even the key to the house. So they went to a store and shopped for purses.

Then they headed to Sarah's favorite shop in the mall. Patty who obviously knew Sarah very well greeted them nicely as they walked in the door. Sarah explained they were there to buy a new wardrobe for Paula. Sarah went on to explain that Paula was interested in trying something new, something quite feminine and yes, sexy.

Patty smiled and told them she understood perfectly. Paul was quite impressed with the look in her eye. He swore he saw them twinkle. At Sarah's insistence he tried on just about every dress in the shop. He couldn't believe how each fit differently and the way they made him look. Men's clothes were not nearly as difficult.

The one thing that women's clothes had in common was the feeling of being exposed. He was very self-conscious about it. His mind was preoccupied with whether his panties were visible or if he was showing too much leg. And of course there was his cleavage.

He tried on everything; dresses, skirts, tops, shoes, scarves, hair clips, bras, panties, corsets and stockings. He was amazed at how much it took to dress fashionably. He learned that a woman could completely change her look and manner with her clothes, something men just couldn't do.

And he discovered that he enjoyed the experience, which really surprised him. He had never been a big fan of shopping, but seeing all those different clothes and how they made him look was fun. Shopping as a man had never been like that.

Patty was pleasant and treated him as any other female customer. They completed the day with no one suspecting that he was anything other than what he appeared to be. And that was an incredible high for Paul.

He had taken what Sarah said to heart, and with her help, selected a wardrobe that was particularly feminine with some pieces being down right sexy. He started their shopping trip in a dress that came just below the knee and ended it with a mini-skirt that was six inches above it.

Sarah slipped Patty a hundred dollar bill behind Paul's back as they walked out of the store. Patty gave her a wink and watched as they walked out into the mall feeling quite successful. Sarah couldn't help but notice the confidence in Paul's walk. The things that she had pleaded with him to do the day before were now happening quite naturally.

And there was another difference too. Not only had he become used to the tight feel of his panties, his bra around his chest, the nylons going up his mostly exposed leg, but now he actually felt sexy.

As they walked down the mall, Paul could not help but notice the looks and stares he received from every man they passed. And Sarah noticed too. And Sarah noticed the little smile that Paul held in check. That alone was well worth the trip.

To celebrate, Sarah took them to get a pedicure where his nails were painted a bright red. As they walked to the car Sarah could hardly tell it was Paul underneath the stylish mini skirt, scoop neck blouse and spike high heels. His walk had transformed into a very natural, and terribly sexy, swish and his mannerisms were right in sync.

"No one suspected me at all" Paul said gleefully to Sarah in his now practiced female voice that rolled off his tongue with ease. And that exposed feeling he had at the beginning of the day morphed into something closer to exhibitionism that he now found daring and exciting.

"Yes, that's right. You did it, Paul. Excuse me, Paula. I'm glad you noticed. You make a beautiful woman. I told you that you could do it. I don't know if you noticed, but you really turned some heads back there."

Yes, he had noticed but couldn't bring himself to say anything. He enjoyed turning heads, enjoyed it very much. He knew they were looking, wondering what was hidden underneath his skirt, behind his blouse. If only they knew. Yes, this was definitely fun.

Paula. The name stuck in his head. He could remember when he was a kid in school how the others would tease him by using that name. But now it fit... perfectly. And he did not feel the least bit upset hearing it from Sarah. He said it again in his mind and just as quickly became Paula.

He was surprised that evening when Sarah handed him a black see-through baby doll trimmed with little red roses to wear for bed. She smiled at him saying he had certainly earned it.

He wasn't sure how to take that. But he liked the way females indulged themselves with sexy things. Did she know how much it would turn him on?

He slipped it on and luxuriated in the feeling of the sexy material as it slid sensuously against his skin. He looked in the mirror and shuddered with pleasure, but was somewhat embarrassed by the fact that Sarah could easily see the rather unfeminine bulge straining inside his cute little see-through lace panties trimmed with little red roses.

He thought about holding his hands in front to hide it, but that would just make it worse. He looked at her embarrassed. Sarah gave him a comforting look. It was if she understood perfectly. Not a word was spoken.

"Shall we have our glass of wine?" she asked. Only then did he realize the daring see-through nightgown she was wearing as he had been so preoccupied with his embarrassment. Her breasts were clearly visible.

"Yes, that sounds good" he said wondering if she realized how exposed she was.

They met in the den once again. He wasn't sure what to make of the situation. Although her panties were solid satin, the rest of it was perfectly see-through. She might as well have been naked. He could clearly see her breasts, her nipples, everything. Her nipples were hard too. She was clearly excited.

His poor cock was painfully erect and jerked with excitement within his see-through panties. She could see him just as easily as he could see her. Sex hung in the air and he felt extremely awkward.