When the 30 year old Virgin met the Prostitute

Jeremy had thought about it for years. A last resort decision for him, something that he kept making excuses for why he shouldn't consider the option. But after a bad joke one of his friends made about him while watching a game a few weeks earlier made him take the decision seriously. He and his friends were just talking about the women they were recently dating and Jeremy had to make another usual excuse of why he hasn't been seeing anybody. Then his friend joked that its been so long for Jeremy his virginity is making a comeback. They all got a good laugh, even Jeremy couldn't help laughing. But when the laughter ended, Jeremy had to hide the look of disappointment he had in himself. The truth was that Jeremy was indeed an actual virgin. A 30-year old virgin. And like most men he lied about the sexual conquests he had in the past. And what he couldn't help thinking that if this continued, he would eventually be a 40-year old virgin, a joke made by that movie, but is actually very pathetic in real life. Granted, he's still ten years away from being that joke, but he already wasted his twenties not getting laid, he dreaded the idea of spending his thirties the same way.

His friends just assumed he was shy around women which is why he doesn't get as lucky as they do. Being shy was just one of his issues. He gets nervous around women; he doesn't know how to talk to them other then as a friend. Even after he gets used to the women had 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.

So finally, after that mild joke his friend made, Jeremy made that last resort decision he's 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 it was just done for financial reasons and not a real personal connection. He thought maybe if he just got some experience being with a woman, he would have more confidence when it finally comes to having sex with a future girlfriend, hopefully with many women in the future.

But the question is how to go about getting prostitute. Its not that easy. Searching on the internet was too risky, he heard too many bad stories from one of his friends who is a lawyer about the guys that he represented who got busted from trying to get a hooker online. And he got more stories from another friend who's a cop about the guys who tried to get a street prostitute; if they weren't getting arrested, they would get robbed.

So, there was one solution he had left. Something that was still risky but probably won't get him into as much trouble. In one of the few places he doesn't feel nervous around women is at the strip club. He feels more comfortable there because there are no strings. He can enjoy seeing beautiful naked women, enjoy some good lap dances, and even talk to them without being too nervous around them. He enjoyed buying a dancer a drink and talking to them before they go for the lap dance. It's probably because money was involved so it was more business then reality, but it still helped him and made him feel better being around women.

Now he knew of course that not all strippers are hookers. The vast majority of them are just good women who wants to earn some money. But there are a few in between who were definitely the stereotype and would commit prostitution for that extra money. Over the years he had a few strippers subtly suggest to him that they are willing to do more in the backrooms. 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.

The dancers who suggested that to him in the past were long gone so now he had to try to find someone new that he could pay for sex. And he didn't want to come off as too much of a pervert. He was known by the other dancers as being a nice guy and being a good tipper, he didn't want to do anything that would give him a bad reputation in the club that would affect how he can enjoy himself in the future when hen visits. And he definitely didn't want to be banned for life there. He needed to be extra careful in how he was going to go about doing this. And he knew he definitely didn't want to get laid inside a strip club where he could get caught and even if he didn't 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 convince them to meet him in a hotel, where he can have a good bed to have sex on.

He decided that he would start by asking one dancer he knew about the subject. There was one dancer that he had gotten to know over the years. Her stage name was Desire, she started dancing at the club almost five years ago. She was a good dancer on stage and an even better lap dancer. And he had found her to be good for a conversation. Sometimes he would buy her a drink before or after the lap dance to just talk. Jeremy wasn't going to ask her to have sex for money, he knew better than that, she definitely wasn't the type. But instead he was going to ask her if she knew if any other dancer did do that on the side. He figured that he has earned enough good will with her over the years to ask this one question without getting into any trouble.

DESIRE/KIMBERLY

Kimberly started dancing right away after high school. The second she graduated, she packed up and went to live with one of her older friends the next town over. 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. One of her friends, Tara, who graduated two years earlier and she stayed in touch with told her how much money she was making dancing and how fun it can be which made Kimberly excited to do that. Tara did warn her about the downsides of stripping, things she need to expect. It did give Kimberly some pause about dancing, but she decided to go ahead with it. So, the same week she moved in with Tara, she auditioned at the club she worked at and got the job and that's what she has been doing for the next 8 years of her life.

It was no surprise to anyone that got the job so fast. She was very young and beautiful with long blonde hair, and an amazing body with natural 38D's. And to top it off she worked the stripper pole the first time as if she was doing it for years. It was Tara that 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 that she never got into was when the customers tried to convince her to do more things for money. Most of the time they just tried to ask her for a hand job or occasionally a blowjob, but sometimes when they were really confident, they would ask for sex. She always said no, never wanting to go that route for money no matter how much money they were offering. But that doesn't mean she was never intrigued by the idea of it.

Her friend Tara confessed that she had tried prostitution for a short while. Never in the club, they were very strict about that. But she didn't like it as much as she would and quit. Kimberly felt that it would be something that she could do but. She felt that prostitution was no big deal as long as it was done safely. And she was really enjoyed sex, having been with several men, even a few women, Tara being the first woman she ever slept with. But for years she had put off that idea. As brave as she was, she was incredibly nervous about what could happen if she ever did become a prostitute. So, she continued with just lap dancing and turning down any offer for sex.

THE CONVERSATION

Jeremy walked into that strip club and was lucky enough to find his favorite seat empty and took it immediately. The club had a website that featured the daily schedule of the dancers and saw that one of his favorite dancers, Desire, was dancing around this time. Less than ten minutes later she appeared on stage, performing to her favorite usual songs. He loved how much she enjoyed dancing on the stage and never failed to perform. When she finished, she came 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 during their lap dances, 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 a lap dance that she promised first. It took almost half an hour before she came out of the back room where the lap dances are performed. She sat next to him and he ordered her favorite drink for her.

They began talking about their week, the ups and downs. New jokes and stories were told. Jeremy had to bring him the courage to ask his question; 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 that he called her Kimberly. "Its gonna sound strange and I hope you can keep an open mind about what I'm going to ask."

"Sure, what is it?" she asked. At that moment, she had the feeling that she usually gets when guys began talking that way. She felt he was going to ask to pay her for sex. Even though she was still intrigued by the idea and contemplated it, she wasn't sure she could do it.

"This is hard for me to ask, but I'm just going to say it."

"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.

It took Jeremy by surprise that she aske that, but figured as a dancer she probably has to deal with people bringing it up to her.

"Yes, I mean sex."

"Why do you want to know?"

He wasn't going to tell her that he was still a virgin, that was just too embarrassing to admit. So, he lied and told her that its been too long since he last had sex and just needed to get laid, to get it out of his system. He told her he had thought about it for a while, and considered it carefully before coming to that idea.

Kimberly was surprised by the conversation. Its usually the guy asking her for sex, not asking if she could help them get it from someone else. As Jeremy was explaining to her why he wanted to pay for it, she began to contemplate the idea that she could be the one to do this. She knew Jeremy for a while now; a very nice guy, excellent tipper, and from what she got from the lap dances she gave him she suspected that he had a big dick in his pants. She figured he could be a good kind of practice for her first time at prostitution. She could use him to see how it goes, and if she enjoyed it, she would do it again with other customers. If not, its only one time she did it and just stop."

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

"You know someone?" He asked.

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

Jeremy was surprised. Although she was the first dancer, he thought of asking to pay for sex, he didn't think she was the type to do this and figured it was ok to just ask her about the other dancers.

"You? I had no idea, you do that."

"Actually, I never did," She said.

She began to explain that she had thought 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 that she could try it for the first time with him and see how she liked the idea of being a prostitute. If not, she would just not do it again.

Jeremy thought that this was a perfect idea. Even though he was going to go through with this idea, he was still generally nervous about hiring a prostitute. He felt comfortable around Kimberly and she would be perfect for him for his first-time having sex. And he figured he could do her a favor by being her first client, to see if she likes it or not.

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

"Great," she replied.

They finished their drinks while hammering out the details of what they were going to do.

THE HOTEL

At the club they exchanged phone numbers so that they text each other on a good time to meet up and for Jeremy to let her know that he got a hotel room ready. He had thought about just inviting him over to his place but decided he wanted to keep this separate from his own personal life as much as possible. They agreed to meet up at 9pm that night, it gave them both time to have their own dinners and be ready to see each other.

They were both nervous about the situation. Kimberly didn't know 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 since she was going to be a real whore for the first time ever. The clothes were going to come off eventually but that doesn't mean she didn't want to look a certain way, presentation is everything.

She confided in her roommate Tara about what she was going to do, surprising her. She was against the idea, warned her of her own experience with prostitution. But she couldn't change Kimberly's mind, and when she found out that she was going to be seeing Jeremy she admitted to being jealous. She also found Jeremy cute, and had many lap dances with him and got a good idea of what he's like. She helped Kimberly find a classy yet sexy dress she could wear and gave her advice on how what to do for the night.

Jeremy didn't know what to do either. He 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 would think he wasn't taking her seriously. He even thought about wearing a suit and tie, but thought that might seem like he was trying to hard. He eventually decided on some khakis and a nice shirt, something that looked good but not like he was trying too hard to impress her.

He even spent some time finding information online about the right type of condom to use. He didn't want to talk to his friends about what they use without risking too many questions being asked. He eventually decided on one that seems widely popular that had a good feel for him as well as being good for her. He also took the time to have the hotel get a bottle of champagne ready for him, thinking it would be nice to offer he something to drink before and probably after they sleep together. Before he went to the hotel, he decided to watch some porn and jerk off, it would relax him and thought it might make him last longer later on with Kimberly.

He got to the hotel first of course early, checking himself in and taking the time to be ready. When she was close by, she texted him she'd be there soon. He was starting to get extra nervous and began doing pushups. When he realized he was beginning to sweat from the work out he ran to the bathroom to clean up and used some cologne he brought with him to mask the smell of sweat.

"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 began to run to the door. He quickly stopped, realizing that he was looking too anxious. He took a deep breath, told himself to relax and walked the rest of the way to the door. 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 never seen her dressed up so well. The only time he ever seen 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; showed just enough cleavage but in a sensible way.

They greeted each other and he invited her in. She took a look around the room, it was a nice hotel, she never been in one so classy before. She hoped that Jeremy didn't spend too much money on the room, he was already going to spend more money later on.

"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 and two champagne glasses next too it. He popped the bottle and poured it in 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 its 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, done this many times, so its nothing we don't already know what to do."

"Odd way of saying it, but you're right." She finished her drink and se 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."

I searched his pockets, momentarily forgetting which one he 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 scattered everywhere. Kimberly had a good laugh and helped Jeremy pick up the bills.

"You didn't have to get so much 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 talking his money, but quickly reminded herself that get attached to every customer that is nice to her. Especially if she decides to continue this new career move.

She sorted out the money and counted exactly $500 that the agreed up, put it in her purse and set it on the night stand next to the champagne bucket.

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

"Ok," 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"

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, he was worried he was going to blow his load in his pants before they ever even got to the sex part. 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, it is. Its kind of cute in a weird way," she said. "I know you said its been a few years since you last had sex, but it will be ok."

"Sure it will."

"Its like riding a bike. You never forget."

She took off her bra and Jeremy was now down to his boxers. She playfully pushed him back where he landed sitting on the edge of the bed. She dropped her black panties, revealing the first time to him her shaved. She held back from giggling at the face that Jeremy made seeing her pussy. She then got down on her knees and went for his boxers.

"But what if I never rode a bike before."

"What do you mean?" she asked as she pulled off his boxers. His massive erection flying straight in the air, she was very impressed with what she saw.

"I mean I never rode a bike before," he told her.

"Jeremy, it's just a metaphor. Granted, not the most original one but it works the same way."

Jeremy went for the condom he had ready on the night stand. She took it out of his hand and tossed it away. She reached up to her purse on the night stand and pulled out her favorite type of condom to use, assuring him that its better than what he had and that it would feel good for both of them. She easily ripped open the condom as she had done many times before and went to put it on his hardened dick.

"Wait!" He snapped at her. "Let's just hold on a minute."

"Why?" she asked with much surprise.

"I just thought we are going too fast, maybe we should take a few minutes, maybe talk a little. We don't have to rush into this."

She looked up with a stern look on her face.

"Jeremy, let me ask you something."

"Ok."

"Do you want to be a virgin forever?"

Jeremy was of course more than surprised by that comment. He had no idea that she had figured it out on her own like that. But after thinking about it for a few seconds, how can he blame her for figuring it all out.

"Was I that obvious?" he asked.

"A little," she replied.

"How long have you known?"

"I suspected couple of years ago. You kind of confirmed it for me tonight."

"Shit," he said. "What now?"

She got off her knees and sat next to him on the bed.

"Listen, its ok. There's nothing wrong being virgin in your mid-twenties."

"I'm thirty," he told her.

"Shit, are you serious?" she snapped at him. "You need to get laid, and you need to let me do this for you. If not, I can just give back the money and go, and we could go back to the way things were at the club. I don't mind that, you're my favorite customer, the other dancers are jealous that I'm your favorite dancer. But you need to get laid, if not now you'll only gonna make excuses to keep putting it off and next thing you know you'll be a forty-year-old virgin.

It was that last comment that made him realize that he needed to do this. It was the idea of one day being a forty-year-old virgin that motivated him to find a prostitute, and he was now ready to finally do this. No more lame excuse, he was just going to finally have sex and enjoy himself with a beautiful woman.

"Ok, lets do this."

"Great," she said excitingly, "you won't regret this.

She got back down on her knees, got between Jeremy's legs and put the condom on his still hardened dick. Without any hesitation, she opened her mouth and took his dick into her mouth. Her lips firm around the shaft as and she began slowly bobbing her head up and down, playing with his balls with one of her hands. Every few now and then she took the dick deeper into her mouth, gagging on it, she knew how much men loved that. Jeremy was enjoying every moment of the blowjob, even with the condom on it felt fantastic. He has had a few blowjobs before but never as intense as what he was feeling now.

After several minutes Kimberly released his dick from her mouth and looked up at him.

"You ready?" she asked.

"Yes, more than ever," he replied.

She got off her knees and got on the bed with him. They began kissing deeply as their bodies pressed against each other. Tara warned her to never kiss a customer, it was too personal and no kissing was a good way for a hooker to keep it all business. But Kimberly couldn't help herself, Jeremy was cute and thought he should be allowed to kiss the girl he was going to lose his virginity to.

Jeremy got Kimberly on her back; she instinctively opened her legs wider being ready for him. Jeremy, not really knowing what to do tried to guide his dick to her pussy but kept missing the mark. Kimberly couldn't help herself as she giggled at his clumsiness.

"Oh, come on, don't laugh," he said.

"I'm sorry," she said. "It just reminds me of my first time. The guy I was with had trouble getting it in there in the beginning also."

"At least I know I'm not the only one this happened to," he said smiling.

"Don't worry about," she said reassuring him. "You got this; you'll be amazing."

With that he found his mark and slid his dick right into her pussy. Kimberly had big dicks in her before, but Jeremy was exceptionally huge and thick and it felt amazing being in her. Jeremy left it in there for a few seconds, enjoying the feel of her warm pussy in around his dick. He has never felt something so wonderful before. He started fucking her slowly, she moaned in his ear with each pump into her body. He began to go faster as she held him tightly, her fingernails slightly digging into his back giving him small scratch marks.

They both turned over with Jeremy on his back and Kimberly now riding him. Her hands were firmly paced on the headboard for balance as she was bouncing around his dick. Jeremy reached up and grabbed her big tits and just held his hands there squeezing them. She had to hold back laughing at the rookie move he was doing; she couldn't blame him though. She started going faster around his dick, screaming, enjoying every moment as much as Jeremy was.

Jeremy got Kimberly on her back again. He thought about going for doggie style or another move, but didn't know how to go about it. He figured he'd stick with what he knows now and then later learn how to get women into different positions.

He held her tightly as started fucking her more intensely. Kimberly was screaming into his ear, begging for more. Jeremy had to slow down a little to catch his breath while still fucking her, she didn't like that but saw the look on his face and understood he needed to take it easy; he was doing a good job, but was still new at this. Eventually he will learn to keep going without slowing down. After about a minute he picked up the pace again and she was yelling crazy things in his ear, things he never thought he'd ever hear a woman say. For some reason he responded with comments of his own, calling her a slut, a whore and other things. He didn't know why he was saying it, it was an instinct that made him say it and not only did he enjoy saying it, Kimberly was enjoying being called a whore and other nasty things as well.

After nearly half an hour of fooling around, Jeremy started to feel that intense feeling that every man feels in his dick that it was soon to be over. He did his best to hold back, managing to get another couple of minute before finally releasing his cum and soon after began to slow down and soon after he was completely done and got off of Kimberly and laid next to her. Although Kimberly wished it would continue, near the end she was getting so excited that she was afraid she would pass out from shortness of breath, so she was a little relieved to be done and able to breath normally.

"I know this is a cliché to ask, but how was I?"

"Fantastic," she said. "I usually say that to guys who were bad just to make them feel good but this time I can honestly say it was fantastic."

"Thank you," he said with a big smile. "How do you feel about your first time at prostitution."

"It feels good, I enjoyed myself. I don't think I'll get every guy to be as good as you but it will still be something that I can do on occasion with the right person."

After a while of talking in bed she decided it was time for her to leave. They both got out of bed and began to dress themselves back up. Kimberly went to the bathroom for a few minutes to wash up before heading out. Before she left the hotel room, she let Jeremy kiss her one more time before they said their good byes.

Jeremy would pay her a few more times over the next few months, those times he decided to invite her to his place. Eventually he began dating regularly and eventually getting the confidence to make his move and having sex with the women he was seeing. Over the next few years, he has slept with more than two dozen women.

Over the next few years for Kimberly she has continued dancing at the club and meeting guys she could trust to pay her for sex. She was good at picking out guys who wouldn't get too creepy for her and be discreet about what she did on the side. Eventually Tara got back into prostitution with Kimberly, and in a few cases were hired by the same guy for threesomes. In one occasion even Jeremy paid Tara for her company. But when Kimberly was on the verge of turning 30, she decided it was time for her to get more serious about her life. She stopped the prostitution side of her life, convinced Tara to stop as well, and just focused on dancing while she was going to the local community college to get her degree.

Jeremy didn't come around the club as much as he used to, but when he did, he always got a lap dance from Kimberly. She always asked about his latest sexual conquest, impressed with how much of a player he had become. At one of the last times Jeremy visited her, h was glad to hear from her that she stopped hooking and was going to school, and that she was looking around for a regular job. As they talked, Jeremy finally did something he always wanted to do and asked her out. She agreed, he was a great guy and never judged her for her life. Three years later they got married.