First Time in the City

Michael was attending an industry conference in New York City. He worked as a salesman for a southern industrial chemical company. Michael had an exceptionally good year and his boss rewarded him with this junket to the city of bright lights.

Michael was 33 years old and single. He had never been to New York City, and the whole trip was a thrill. He took in the usual tourist sites during times away from the conference.

Michael was also happy to be in New York City for another reason. Michael was a private cross-dresser. He had always loved the feel of woman's undergarments. He usually wore panties, a bra, and tights under his clothes. Something about doing this in a city like New York was particularly thrilling for him, as he walked around the throngs of people with his secret hidden away.

As he walked the city, Michael found himself outside a famous five-star hotel. He walked inside and stood in awe of the architecture and opulence of the hotel. Beautiful and obviously wealthy people were checking in and out. Michael suddenly had to take a bathroom break, so he slipped into the lobby bathroom of the hotel.

Normally, Michael used a bathroom stall when he was wearing his female undergarments, but the stall in this bathroom was taken. He took a chance and stood at the urinal. While he was relieving himself, a well-dressed man in a suit entered the bathroom and went to the stall next to Michael. Michael hurriedly finished his business, hoping the man wouldn't notice his under-attire.

Michael washed up and left the bathroom in a hurry. As he walked toward the lobby, the well-dressed man caught up to Michael and tapped him on the shoulder.

"Excuse me," the man said, "but I couldn't help but notice you are attending the chemical expo."

Michael felt flustered. The man standing in front of him looked to be about 50 years old. He was impeccably dressed, tall with grey hair, and he was wearing a tailored suit that looked like it cost more than half of Michael's annual salary.

"Um, how did you know that?" Michael asked.

"Well, Michael, you have that tag hanging around your neck," the man said.

Michael looked down, suddenly embarrassed, realizing he was wearing his conference badge.

The man continued, "My name is John Dollinger. I work with Apex Chemicals." He extended his hand to Michael.

Michael shook Mr. Dollinger's hand. Apex Chemicals was the largest industrial chemical company in the country, and one of the biggest in the world. Michael had heard the name John Dollinger before. He was the CEO and Chairman of the Board of Apex. Michael felt even more flustered. He had never met anyone of Mr. Dollinger's stature before.

"Nice to meet you, Mr. Dollinger," Michael managed to spit out.

"Michael, I was just getting ready to have a drink in the bar. Would you like to join me? Maybe you can tell me what you do for your company," Mr. Dollinger said.

"Sure, Mr. Dollinger. It would be an honor, sir," Michael sputtered.

"Michael, call me John. Maybe some other time you can use Mr. Dollinger, but for now, it's just John, ok?" Mr. Dollinger said.

"Great, John," Michael said, regaining some confidence at Mr. Dollinger's friendliness.

Michael and Mr. Dollinger walked to the bar together. Michael was blown away by the opulence. It was nothing like the Red Tavern back home with $2 domestic nights. The same beautiful and wealthy people Michael had seen in the lobby were packed in the bar. There seemed to be a lot of men who looked a lot like Mr. Dollinger, rich and powerful, accompanied by women half their ages. Michael had never seen anything like it.

Michael and Mr. Dollinger sat at the bar. "What are you drinking, Michael?" Mr. Dollinger asked.

This threw Michael off. He wasn't quite sure what to order without making himself look like a rube to this powerful man. Michael regained his senses and said, "Whatever you are drinking is fine with me, John."

Mr. Dollinger ordered two single malt whiskeys with just a splash of water. Michael noticed the bottle as the bartender poured the drinks -- Macallan 30-year-old scotch whiskey. Michael did not know much about whiskey, but something told him this was not a drink he could afford, particularly in the place like this. He silently prayed Mr. Dollinger would be paying the bill.

Mr. Dollinger raised his glass and said, "To new friends, Michael. Cheers." Michael raised his own glass in response.

Michael took a sip of the drink and the burn was intense. But it was good, better than any whiskey he had ever tasted.

"So, Michael, why don't you tell me about yourself. What brings you to the expo?" Mr. Dollinger inquired.

Michael was grateful for the opening and he began talking about his work and the various products he sold. It would have been exceptionally boring to most people, but Mr. Dollinger listened intently. His eyes were focused on Michael the whole time.

Michael couldn't help but notice Mr. Dollinger was exceptionally handsome and fit for someone his age. Michael was straight, but he could see how the 20-something-year-old women with the older men surrounding them in the bar would swoon over someone like Mr. Dollinger. Most of the other men around the bar were overweight and looked pasty. Michael thought to himself how nice it must be to be rich.

Michael and Mr. Dollinger finished their drinks. Mr. Dollinger ordered another round. Michael was already starting to feel the effect of the first drink. He was talking more freely with Mr. Dollinger. He found him easy to talk to.

As the bartender set the second round before them, Mr. Dollinger placed his hand on Michael's back. This startled Michael and his face turned a deep red. He was not sure if Mr. Dollinger could feel the bra under his shirt when he did this; he hoped to God that he couldn't. Michael felt mortified, and suddenly wanted to leave.

"Mr. Dollinger, John, I mean, I probably should be getting back to my hotel. I've got an early day tomorrow at the conference," Michael said.

Mr. Dollinger's hand was still on Michael's back. He looked Michael directly in the eye and said, "Michael, you'll be coming to my room first. I'm looking forward to seeing you in your bra and panties."

Michael's face turned even redder. He was truly horrified to have been caught like this. "I'm so sorry, Mr. Dollinger, I really have to be going," Michael said and started to get up.

"Michael, sit down," Mr. Dollinger commanded. It was a voice like Michael had never heard before. A voice filled with power. A voice that commanded respect. Michael sat back down on the stool, feeling confused and afraid.

"Michael, it's all going to be ok. I'm not going to hurt you," Mr. Dollinger said. "Actually, I want to help you," he continued.

Michael sat silently and listened. Mr. Dollinger's hand was on Michael's knee now. Michael could not understand why, but he could feel himself getting hard in his panties from the touch of Mr. Dollinger's hand.

"Michael, here's the key to my suite. It's room 2628. Go upstairs and wait for me while I finish my drink. I hate to waste a good scotch. When I get up there, I want to see you in your bra and panties and nothing else. Do you understand?" Mr. Dollinger said. He handed Michael the room key.

Michael, feeling overwhelmed by this man and the fact that he was suddenly rock hard in his panties, said only, "Yes, John."

"Good, Michael. I'll be up soon. And from now on Michael, you should call me sir or Mr. Dollinger," Dollinger said.

"Yes, sir," Michael said.

"Ok, get going Michael. I'll be up soon," Dollinger said.

Michael got up from the bar stool and walked out of the bar. To the left was a bank of elevators. To the right were the lobby doors and the street. Michael thought about whether he should just run out the door. But, he found he did not want to. Michael wanted to do what Mr. Dollinger told him to do, as embarrassing as it might be. Michael got on the elevators.

When Michael arrived at Room 2628 he was stunned by how large it was. There was a balcony overlooking Central Park. There was a bar stocked with drinks. There were several rooms, which Michael found as he explored the suite.

Finding the master bedroom, Michael nervously undressed. He stripped down to his bra, panties and tights. He pulled the tights off. He was dressed only in a pair of pink silk panties and a matching pink bra.

Michael was turned on. His cock was hard in his panties. Michael was not very big, but in his current state, an inch of his cock was poking out the top of the panties. Michael lay down on the bed and anxiously waited for Mr. Dollinger.

Michael waited for over an hour. Finally, he heard the door open. He heard someone at the bar pouring a drink. Mr. Dollinger walked in, drink in hand.

"You look very pretty, Michael," Mr. Dollinger said.

Michael's face flushed at this compliment. He did not quite know why being called pretty by this man excited him, but it did. Michael was still hard in his panties.

"Come here, Michael," Mr. Dollinger ordered.

Michael got out the bed and walked to Mr. Dollinger, who was taking a sip from his drink.

"Get on your knees," Mr. Dollinger ordered.

Michael fell to his knees in front of Mr. Dollinger.

"Have you ever sucked a cock before, Michael?" Mr. Dollinger asked.

"No, sir," Michael said, his voice quivering.

"Unbuckle my belt," Mr. Dollinger ordered.

Michael fumbled with Mr. Dollinger's belt, eventually getting it open.

Mr. Dollinger set his drink down on a table. He unbuttoned his pants and pulled them down. Then he pulled his boxer shorts to his knees.

Michael caught his breath. Mr. Dollinger had a huge cock and it was hard. Michael instantly wanted to suck this beautiful cock. He wanted to please Mr. Dollinger.

"Suck my cock, Michael. Just do your best; I'm sure you will be very good at it," Mr. Dollinger said.

"Yes, sir," Michael said. His mouth was watering now, wanting a taste of this big dick in front of him.

Michael reached for it and stroked it in his hand. It was hard and silky at the same time. Michael had never touched another man's cock. Michael could barely get his hand around it, Mr. Dollinger's cock was so thick.

Michael tried to remember every porn film he had ever watched. He moved his hand down to Mr. Dollinger's balls, holding them. They were big and full. Michael opened his mouth and sucked the tip of Mr. Dollinger's cock. "Mmm, that's nice, Michael, you are going to make a good little cock-sucker," Mr. Dollinger said.

Getting into his work now, Michael popped the tip out of his mouth and moved his tongue down to the bottom of Mr. Dollinger's hard shaft. He stroked his tongue up one side of this monster cock, and then the other. Then he moved his tongue to the underside of the shaft and slowly pulled his tongue back up to the tip.

Michael took two inches of Mr. Dollinger's hardness into his mouth again and sucked, pulling his tongue up the underside of the shaft as he did so. Mr. Dollinger grabbed Michael's hair and pushed him further down onto his cock. Michael gagged slightly as Mr. Dollinger's manhood hit the back of his throat for the first time. Mr. Dollinger pulled Michael up by the hair and then pushed him down again, farther this time. Michael gagged again.

"You have to open yourself for me, Michael. When the tip hits your throat pretend you are swallowing something," Mr. Dollinger instructed.

Mr. Dollinger pushed Michael down again, even further this time, and Michael did not gag. He concentrated on opening his throat for this beautiful cock. Mr. Dollinger pulled out, Michael caught his breath, and Mr. Dollinger shoved all of his cock down Michael's throat.

"That's it, Michael. That's how you suck a man's cock," Mr. Dollinger moaned.

Mr. Dollinger began fucking Michael's face, pushing himself deep into his throat and then pulling out to the tip. Michael concentrated on his work, doing his best to pleasure Mr. Dollinger with his mouth.

Without warning, Mr. Dollinger tensed up and began shooting his load into Michael's throat. Michael swallowed the first stream of warm cum. Mr. Dollinger pulled all of himself out of Michael's mouth and held his cock as he fired one warm jet after another onto Michael's face. Stream after stream of cum covered Michael's lips and cheeks. Michael licked his lips, tasting Mr. Dollinger's cum for the first time. It tasted perfect to Michael at that moment.

"Go clean yourself up, Michael," Mr. Dollinger ordered, as he pulled his pants up and buckled them.

Michael did as he was told, finding a soft towel in the bathroom. He wiped Mr. Dollinger's cum from his face and then walked back to the bedroom.

"You can go now, Michael. You did a wonderful job. I want you back here promptly at 7:00 a.m. tomorrow. I have a gift for you since you did so well," Mr. Dollinger said.

Michael said, "I am supposed to be at the conference tomorrow by 8, sir."

"Don't worry about that, Michael. I'll take care of that. You won't get in any trouble with your boss, believe me," Mr. Dollinger said. "Oh, and Michael, there is no need to wear panties or a bra tomorrow. Just wear your regular clothes. Goodnight, Michael."

And just like that Michael was dismissed. He got dressed and left the room. Michael walked out of the hotel not sure how to feel about what had happened. He did know that sucking Mr. Dollinger's cock had been wonderful. Michael grabbed a cab to his hotel, and thought about Mr. Dollinger's dick the entire way back.

When Michael made it to his room, he undressed, took his bra off, and put a nightgown on. Michael lay in his bed and masturbated thinking about Mr. Dollinger. It didn't take Michael long to cum. He came as hard as he could remember, firing his cum all over the silky nightgown. It was so wet and sticky with his cum that he had to sleep in just his panties. Michael set his alarm and fell asleep.

The next morning, Michael caught a cab back to Mr. Dollinger's hotel. He rode the elevator up, eagerly anticipating seeing Mr. Dollinger again, hoping that he would want Michael to suck him off again.

Michael used the key to enter the room. When he walked in, Michael was surprised to see a beautiful young female dressed in a smart suit in the room, along with two other women in white coats. He could see a make-up table and what looked like a hairdresser's table set up in the middle of the room.

The woman dressed in the suit spoke first, "Good morning, Michael. I'm Mr. Dollinger's assistant, Renee. Mr. Dollinger has asked me to tell you that he talked to your boss this morning about you missing the conference. Your boss was perfectly fine. Mr. Dollinger told him you had landed the sales account for Apex Chemicals and that your firm will now be the exclusive agent for Apex products in three states."

Renee was all business as she said this. No smile. She acted like this was just another day at the office.

Renee continued, "Mr. Dollinger has asked that we get you ready to attend a dinner with him tonight with some business associates of his. This is Sharon and Felice. They will be helping to get you ready." Sharon and Felice nodded at Michael, but said nothing.

"You are going to start with Felice. Please take off all your clothes and take a shower," Renee said.

Michael felt confused. He was not sure what this was about. Michael started to speak, but Renee cut him off.

"Michael, there is no need for questions. Mr. Dollinger wants us to get you ready for a dinner tonight, and that is exactly what is going to happen. If you just do what I ask, this will go much quicker," Renee said. "We need to have you ready by 5:00 for drinks with Mr. Dollinger. Let's get started. Get in the shower please."

Michael was bewildered, but he did what he was told. He took off his clothes and jumped in the shower. When he got out, Felice was waiting for him.

Felice handed Michael a pair of black silk panties and instructed him to put them on. Michael did so. He struggled to keep from getting hard. Felice had Michael sit in a chair. She lathered his legs with a soft lavender cream. Felice began shaving Michael's legs.

When Felice finished with Michael's legs, she lathered his chest, stomach and underarms and removed all the hair with a razor. While Felice worked on his upper body, Michael could not help but rub his hands along his smooth legs. He loved the feel of them and wondered why he had never done this before.

After Felice finished with Michael's upper body, he was perfectly smooth from the neck down, except for his cock and balls. Felice slipped Michael's panties down. Michael was rock hard. Saying nothing, Felice slipped surgical gloves on and pulled out a bottle of lube. She poured it onto Michael's cock and rubbed it in. Michael moaned from her touch. Felice stroked Michael until he came. Felice was ready with a towel to catch Michael's cum as he fired one stream after another.

Felice wiped Michael's cock down with a clean towel and then put the lavender cream on his cock and balls. Felice shaved him smooth. When she was done, she pulled Michael's panties back up and led him into the other room, where Sharon was waiting at her hairdressing table.

For the next two hours, Michael watched in amazement as Sharon colored his hair, added extensions and curled it. Michael couldn't believe what his hair looked like when she was finished. It was the hair of a woman, long and auburn, with just the right amount of curl. Michael loved it.

Felice took over again. She gave Michael a manicure and a pedicure. She painted his toenails a bright red and added short extensions to his fingernails. She painted them a matching red, and finished both his toes and fingernails off with a glaze.

It was lunchtime now, and they all took a short break. Michael ate a small salad, but he couldn't stop looking at himself in the mirror with his new hair and nails. He loved them. He loved his smooth skin.

After lunch, a new face arrived, another woman in a white coat. Renee introduced her as Janine. Michael was directed to sit in the hairdresser's chair. Janine pierced Michael's ears. She inserted diamond stud earrings that must have been a carrot each. Michael couldn't image how much they were worth. But they were beautiful.

Another person entered the room, a man this time, who Renee introduced as Frank. Michael sat at the make-up chair, and the man proceeded to shave Michael with a straight razor. After he finished the first time, Frank did it a second time to make sure Michael's face was as smooth as a baby's.

Sharon started working on make-up for Michael's face. Michael watched in the mirror as Sharon worked her magic. Over the course of the next hour and a half, Sharon had turned Michael's face into that of a beautiful woman. Michael looked at himself in the mirror and his heart skipped a beat. He loved the way he looked.

It was 3:00 now and time was growing short to make the 5:00 appointment with Mr. Dollinger. Renee had laid out on the bed a number of different dresses and shoe combinations. While Renee worked to decide the right combination, Felice attached a pair of breast forms to Michael's chest. When finished, she put a beautiful black lace bra on Michael. Sharon added make-up to Michael's chest to blend in the breast forms and make his chest look more natural.

Felice told Michael to hand over the panties he had been wearing all day. He slipped out of them. Michael was hard again. He couldn't help himself. He had been staring at himself in the mirror all day, watching himself transformed into a beautiful woman. It was an amazing turn-on. Felice put her gloves back on, lubed Michael up, and stroked him off again. She was all business as Michael exploded into another towel.

Felice gave Michael a gaffe and instructed him how to put it on. This would keep his cock under control for the evening. Michael wished he could wear regular panties, but understood. It was going to be tough not to get hard as soon as he saw Mr. Dollinger.