The Virgin and the Prostitute

Preferred Title: The Virgin and the First Time Prostitute

***All characters are over 18 and are fictional. Any resemblance to any real-life persons is purely coincidental.

...

JEREMY

It started because of a joke one of his friends made about him. They were hanging out one night, watching a baseball game. The topic of women came up, and they all started bragging about who they were dating or sleeping with on the side. Jeremy had to admit that he hadn't been seeing anyone lately, which made one of his friends joke that Jeremy hadn't been laid in so long that his virginity was making a comeback. They all had a good laugh, even Jeremy, who thought it was funny. But when the laughter ended, Jeremy had to hide the look of disappointment he had in himself.

The truth was that Jeremy, at 30-years-old, was indeed an actual virgin. And like most men, he lied about his sexual conquests to avoid being ridiculed. And he couldn't help thinking that if this continued, he would eventually become a 40-year-old virgin, a joke made by that movie, but which was actually very pathetic in real life. Granted, he was still ten years away from being forty, but he had already wasted his twenties not getting laid, so he dreaded the idea of spending his thirties the same way.

His friends just assumed he was shy around women, which was why he didn't date as much as the rest of them. It was mostly true; he gets nervous around women; he doesn't know how to talk to them other than as a friend. Even after he gets used to the women he has dated, he doesn't know how to move forward with them. He has had some other kinds of sexual experience, some hand jobs and a few blowjobs. He even fingered a few of them in return, but nothing else.

That joke his friend made was on his mind the next few days, making him think about his current options. After giving it some serious thought, he made the last resort decision he had been putting off for years and get himself a prostitute. He felt he just needed to get it out of his system, be with a woman, even if it was just done for financial reasons and not a real personal connection. He also believed that if he simply gained some experience with a woman, he would have more confidence when it came to having sex with a future girlfriend, and hopefully many women in the future.

But the question was how to go about getting a prostitute. Getting one was not as easy as the movies made it out to be. Dating apps such as Tinder were not as easy as people thought, according to some of his friends who tried it. Searching on the internet was too risky. He heard too many horror stories on the news about men who tried that also. And he heard enough bad stories from a cop friend of his about men he had to arrest for soliciting prostitutes in the streets, and if they weren't getting arrested, they were getting robbed by those women.

There was one solution he had left; it was still risky, but it probably wouldn't get him into as much trouble. In one of the few places where he doesn't feel nervous around women, was at the strip club. He felt more comfortable there because there were no strings attached. He can enjoy seeing beautiful naked women, get some good lap dances, and even talk to them without being too nervous around them. He even enjoyed buying a dancer a drink and talking to them before they went for the lap dance. It was probably because money was involved, so it was more business related and they had to be extra friendly to him. It was more fantasy than reality, but it still helped him and made him feel better being around women.

Of course, he knew that not all strippers were hookers. The vast majority of them were just good women who wanted to earn some money. But there were a few in between who were definitely doing it on the side for extra money. Over the years, he had a few of them subtly suggest to him that they were willing to do more for him in the backrooms for a price. At the time, he said no, not wanting to go that route to lose his virginity, but now he felt that was going to be his only option left.

Those dancers who suggested that to him were long gone by then, so he had to find someone new among the other dancers he could pay for. He had to start asking around, but didn't want to come off looking like a pervert. He was known by the other dancers as a friendly guy and a good tipper; he didn't want to do anything that would give him a bad reputation at the club, or worse, get banned for life.

He needed to be extra careful in how he went about asking around. And he knew he definitely didn't want to get laid in a strip club where he could get caught. Even if he didn't get caught, the couches in the backrooms did not feel like an ideal spot to fool around on. If he was going to do this, he was going to ask them to meet him in a nice hotel where they could have more privacy and a good bed to use.

He decided to start by asking one of the dancers he had gotten to know pretty well. Her stage name was Desire. She started working at the club almost five years ago. She was a great dancer, an even better lap dancer, and she was always good for a conversation.

Jeremy wasn't going to ask to pay her for sex; he didn't think she was the type. Instead, he was going to ask her if she knew if any other dancer did that on the side. He figured that he had earned enough goodwill with her over the years to just ask about it without getting into any trouble.

DESIRE/KIMBERLY

Kimberly started dancing right away after high school. The second she graduated, she packed up and moved out. Her foster parents didn't care, she had just turned 18 and therefore they wouldn't be receiving any money from the state to take care of her. She was just a burden to them.

She moved in with one of her friends, Tara, who graduated two years earlier. She stayed in touch with Tara, who told her about how much money she was making from dancing and how much fun it could be. Kimberly, who wasn't too shy about her body, was excited about the idea of it.

Tara did warn her about the downsides of stripping, things she needed to expect. It did give Kimberly some concerns about dancing, but she decided to go ahead with it. The same week she moved in with Tara, she auditioned at the club Tara worked at, got the job, and has been dancing there for the next five years of her life.

It was no surprise to anyone that she got the job. She was young, beautiful, with long blonde hair, and an amazing body with natural 36D's. In her audition, she worked the stripper poll as if she had been doing it for years.

It was Tara who suggested she call herself Desire because of how desirable she looked on stage. The next week, she began doing the lap dances, which wasn't too hard for her. She enjoyed getting paid for getting guys off without having sex with them. There was the occasional creepy guy, but she eventually learned how to deal with them.

The only thing she never got into was when a customer would try to pay her to do more than just a dance. Most of the time, they tried to ask for a hand job and, sometimes, a blowjob. Sometimes, when they were very confident, they would ask for sex. She always turned them down, no matter how much money they offered. But at the same time, she was very much intrigued by the idea of it.

Tara confessed to her that she had tried prostitution for a short while. It began with a few customers at the club before she signed up with an escort agency that paid more money. It was exciting at first, but eventually she lost interest in it and quit.

Tara warned Kimberly about the downsides of it; she understood there were risks, but she still thought it was something she could do. She felt that prostitution was no big deal as long as it was done safely.

Also, she really enjoyed sex, having been with several men and even a few women, including Tara. But, as brave as she was, she was incredibly nervous about what could happen if she ever became a prostitute, especially if she got arrested. She still wanted to try it, but needed to be sure it was safe and worth doing.

THE CONVERSATION

Jeremy walked into the club and was lucky to find his favorite seat empty and took it immediately. The club's website had the daily schedule of the dancers, and saw when Desire would be dancing and got there just in time for her to appear on stage, performing to her usual songs. He loved how much she enjoyed dancing on the stage and never failed to perform.

When she finished, she went around the stage collecting her tips. When she finally came around to Jeremy, she gave him a big smile and greeted him. He was one of her favorite customers, and even when she wasn't just trying to get money from him, she still enjoyed his company.

He asked if he could buy her a drink when she was done. She said yes, but only after she gave two other customers, she promised a lap dance to first. It took almost half an hour before she finished with them and finally had time for him. She sat next to him, and he ordered her favorite drink for her.

They began talking about their week, the ups and downs, and new jokes and stories were told. Jeremy wanted to ask her about the other dancers and was stalling long enough until he got the courage. It was difficult to bring up, and he was making excuses in his mind, but he knew he had to do it.

"Listen, Kimberly, I need to talk to you about something important," he began to say.

He was one of the few people who knew her real name, and she didn't mind him calling her that.

"Sure, what is it?" she asked.

"It's going to sound strange, and I hope you can keep an open mind about what I'm going to ask."

Kimberly had a feeling about where the conversation was going. Whenever she met a customer who talked like that, it usually meant he was going to ask if he could pay to have sex with her.

"Go right ahead," she said, bracing herself.

"Would you happen to know if any of the dancers here that you work with... well... do anything extra on the side?"

"You mean sex?" she asked.

"Yes, I mean sex."

It took Jeremy by surprise that she immediately knew what he was talking about, but he figured as a dancer she probably had to deal with people bringing it up to her all the time.

Kimberly was surprised; usually the guy asked to pay her for sex, not if she knew anyone else would do it. She also felt relieved that he wasn't going to ask if you could pay her to let him fuck her. Even though she was still intrigued by the idea and contemplated it, she still wasn't sure she could go through with it.

"Why do you want to know?"

He wasn't going to tell her that he was still a virgin, it was just too embarrassing to admit. So, he lied and told her that he hadn't been with a woman in a long time and that he just needed to get laid to get it out of his system. It was a reasonable enough excuse, which he had learned from a few of his friends.

As Jeremy was explaining to her why he wanted to pay for it, she realized that he could be the one she could try it out with. She already knew what a nice guy she was and felt he was a safe option to be her first customer. She figured he could be a good kind of practice for her to see how she liked it. If she didn't like it, it was only once, and she would just stop.

"I think I can help you," she said.

"You know someone?" he asked.

"Yes," she said with a big smile. "Me."

"You?" he said, surprised.

Although she was the first dancer he thought of asking, he didn't think she was the type who did that.

"Actually, I never did," she said.

She began to explain how she had been thinking about it for a while, something fun to do for extra money, but never got the nerve to actually go through with it. She said she could try it with him first because she knew him well enough and figured she would be safe with him. Afterwards, she could decide whether or not she wanted to continue doing it.

Jeremy thought it was a perfect idea. Even though he settled on the decision to hire someone to sleep with, he was still nervous about doing it. He felt comfortable around Kimberly and felt he would be more relaxed with her for his first-time having sex. He also figured he could do her a favor by being her first client, to see if she liked it or not.

"Ok," Jeremy said, with a big smile. "If you're up to it, let's do it."

"Great," she replied, enthusiastically.

"But before we agree on this, will you still be OK if I came around here afterwards?" he asked. "I don't want to make you feel uncomfortable after doing that."

She thought it was sweet that he was trying to take her feelings into consideration.

"It's OK," she said. "I still give lap dances to ex-boyfriends who visit me here, so I'll be just fine."

Jeremy was relieved to hear that. If it didn't work out as well as he hoped, he still wanted to visit her at the club without making it awkward for them.

They finished their drinks and went to get their usual lap dance. This time, Jeremy paid for a champagne court so he could have a full half-hour with her. It was enough time for them to have fun together and then talk about the details of what they were going to do.

THE HOTEL

They exchanged phone numbers at the club in order to stay in touch about their plans. Jeremy thought about inviting her to his place but decided he wanted to keep this separate from his personal life as much as possible.

A week later, when they agreed on a day to meet each other, he got them a very nice hotel room that he knew about. They agreed to meet up at 9 pm that night, which gave them both time to have their own dinners and be ready to see each other.

Kimberly was nervous about meeting him. As confident as she was, especially when it came to sex, being paid for it was a completely different situation.

She confided in Tara about what she was going to do. Tara was surprised and completely against the idea. But when she found out that it was Jeremy that she was going to be seeing, she changed her mind and said he was a great choice to try it out with. Like the other dancers, Tara thought Jeremy was cute and very friendly. She had plenty of lap dances with him and got an idea of what he had in his pants.

Kimberly's biggest problem was that she didn't know how to dress for the occasion. She wasn't sure if she should just show up dressed casually in jeans and a sexy top, or wear something classy and respectable, or wear one of her sluttier outfits. The clothes were going to come off eventually, but that didn't mean she didn't want to look good for him; presentation is everything, after all. Tara helped her find a sensible dress to wear that was sexy yet classy.

Jeremy didn't know what to do either and spent a lot of time trying to figure out what to wear. He also thought about just dressing casually in some jeans and a t-shirt, or at least a polo shirt, but thought she might think he wasn't taking her seriously. He thought about wearing a suit and tie, but thought that might seem like he was trying too hard to impress her. He eventually decided on some khakis and a nice shirt, something that looked good for any occasion.

He also had the hotel prepare a bottle of champagne for him, figuring it would be nice to provide her with something to drink before and possibly after they slept together.

Before he went to the hotel, he decided to watch some porn and jerk off. He said it helped him to relax and ease his anxiety, and he figured it might make him last longer later on with Kimberly.

He got to the hotel first to check in and make sure everything was ready for them. When she was close by, she texted him that she'd be there soon. He was starting to get extra nervous and began doing pushups, something else he does to help him relax. When he realized, he was beginning to sweat from the work out, he ran to the bathroom to clean up.

"Come on, Jeremy, keep it together," he told himself in the mirror. "Just be cool and take it easy. It'll be great."

He heard a knock on the door and got nervous again. He took a deep breath, told himself to relax, and went to open it.

He opened the door and saw Kimberly standing there smiling. He was surprised at how gorgeous she looked. He always thought she was beautiful but had never seen her dressed up so well. The only time he ever saw her wearing clothes was when she was wearing a bikini or something slutty on stage before she took it off. Today, she wore a beautiful black dress that hugged her curves the right way; the dress showed enough cleavage but in a sensible way.

They greeted each other, and he invited her in. She took a look around the room. She had never been in a hotel room that was so classy before and was very impressed. She hoped that he didn't spend too much money on the room since he was already going to spend more money on her.

"Nice hotel room," she said.

"Thank you," he replied. "You want something to drink?"

"Sure."

He went over to the night stand where the champagne bottle was in a bucket of ice with two champagne glasses next to it. He popped the bottle and poured it into both glasses and handed her one. They both clinked their glasses and started drinking.

"Are you nervous?" She asked. "I kind of am."

"A little," he replied.

"But we shouldn't be, right? We're both adults here, and it's not like anything we haven't done many times before. "

"Yes," he replied, and took another big gulp of his champagne. "You're absolutely right. We've done this many times, so it's nothing we don't already know what to do."

"Odd way of saying it, but you're right." She finished her drink and set the glass back on the table. "I guess we should get started then"

"I guess we should," he replied, and nervously finished her champagne.

"Do you have the money?" she asked.

"Yes, I do."

He searched his pockets, momentarily forgetting which one he had put it in. They agreed that $500 was a good price, and he took it out of the bank earlier in small bills. When he finally found the money, he was getting so nervous that the money flew out of his pocket and was scattered everywhere. Kimberly had a good laugh and helped Jeremy pick up the bills.

"You didn't have to get it in so many small bills," she said.

"I thought it would be a good idea. If you didn't put it in the bank, then you didn't have to worry about spending it somewhere that couldn't break a hundred."

"Thanks for being so considerate," she said.

Now she was beginning to feel nervous again. She forgot how sweet Jeremy could be. She was beginning to feel guilty about the idea of taking his money, but quickly reminded herself that it wasn't a good idea to get attached to every customer that was nice to her. Especially if she decides to continue this new career move.

She sorted out the money, put it in her purse, and set it on the nightstand next to the champagne bucket.

"OK, I think we're ready now," she said as she began unzipping her dress and pulling down her shoulder straps.

"All right," he said.

They paused for a long time.

"Aren't you going to start taking off your clothes?" She asked.

"Yes, that is the next step I need to take," he said nervously.

She got her dress off as Jeremy just took off his shirt. She was wearing a black half-cup bra and matching panties. Jeremy's erection began to grow, and he was worried he was going to blow his load in his pants before they ever got to do anything with her. He reminded himself that it usually took him twenty good minutes of jerking off before he finished, and he never ejaculated during his lap dances with Kimberly or the other dancers.

"Relax," she told him. "You're too nervous."

"Is it that obvious?" he asked.

"Yes, but it's kind of cute," she said.

She took off her bra, and Jeremy was now down to his boxers. She playfully pushed him back and he landed on the edge of the bed. She removed her black pantyhose, revealing her shaved pussy for the first time to him. She held back from giggling at the surprised face he made after seeing her pussy. Usually, she wore a thong at the club that showed plenty of her ass but not much of the front side, so he never got a good look at her pussy before now.