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.
