The Virgin and the Prostitute

She then got down on her knees and went for his boxers, but Jeremy held her back.

"Don't be nervous," she said. "I know you said it's been a while since you last had sex, but it will be OK. It's like riding a bike; you never forget how to do it."

"But what if I have never ridden a bike before."

"What do you mean?" she asked as she pulled off his boxers.

His massive erection shot straight up into the air. She was very impressed with what she saw.

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

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

Jeremy went for the condom he had ready on the nightstand. 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 it was 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 for a minute."

"Why?" she asked, much to her surprise.

"I just thought we were 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. She got off her knees and sat down next to him on the bed.

"Jeremy, let me ask you something."

"Ok."

"Do you want to be a virgin forever?" she asked.

Jeremy was, of course, more than surprised by that she had figured it out, but at the same time, he couldn't blame her for realizing it.

"Am I that obvious?" he asked.

"A little," she replied.

"How long have you known?"

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

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

"Listen, it's OK. There's nothing wrong with being a 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, and the other dancers are jealous that I'm your favorite. But you need to get laid now, because if you wait any longer, you'll just make excuses to keep putting it off, and before you know it, you'll be a forty-year-old virgin."

That last part reminded him of why he was there. It was the idea of possibly being a forty-year-old virgin one day that motivated him to find a prostitute in the first place. He decided that no more lame excuses would suffice; he was going to have sex and enjoy it with a beautiful woman.

"Ok, let's do this."

"Great," she said, excitedly. "You won't regret this.

She got back down on her knees 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 were firm and sealed around the shaft as she began slowly bobbing her head up and down with her tongue, massaging the shaft every time it went into her mouth.

She would occasionally take the dick deeper into her mouth and gag on it. Jeremy was enjoying every moment of the blowjob. Even with the condom on, it felt fantastic. He had 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 she couldn't herself; she thought he 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, and she instinctively opened her legs wider to be 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 it," she said, reassuring him. "You've got this; you'll be amazing."

Jeremy found his mark and slid his dick right into her pussy. He lingered for a few seconds, enjoying the sensation of her warm pussy around his dick. He had never felt anything 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 for Kimberly to be on top of him. As she bounced around on his dick, her hands were firmly placed on the headboard for balance. Jeremy reached up and grabbed her big tits and just held his hands there, squeezing them. She had to hold back her laughter at his rookie mistake, but she couldn't blame him. She started going faster around his dick, screaming, enjoying every moment as much as Jeremy was.

Jeremy got Kimberly on her back again. He held her tightly as he started fucking her more intensely. Another orgasm went through her body and she began to yell 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, among other things. He didn't know why he was saying those things; it just came natural to him, but he saw how much she liked it, so he continued.

After nearly half an hour of fooling around, Jeremy couldn't hold back much longer and felt it was going to be over soon. He did his best to hold back, wanting the time with her to last much longer. He only managed to get a couple more minutes before finally releasing his cum.

He began to slow down until his dick got soft and pulled out of her. Afterwards, he got off of Kimberly and laid down next to her. Although Kimberly wished it would continue, she felt she was getting too excited and was a little relieved to be done and able to breath normally.

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

"Amazing," she said. "I usually say that to guys who are bad to make them feel good, but this time I can honestly say it was amazing."

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

"It felt good. I enjoyed myself," she replied. "I don't think I'll get every client to be as good as you were, but it's still something 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 got the confidence to make his move and sleep with some of them. Over the next few years, he slept with more than a dozen women.

Over the next few years, Kimberly 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 would be discreet about what she did on the side. To make even more money, she hooked up with the escort agency that Tara used to work for and made a lot more money from them.

Eventually, Tara got back into prostitution with Kimberly, and in a few cases, they were hired by the same guy for threesomes. A few times, even Jeremy paid Tara for her company. But again, it didn't last long for her as she lost interest in that lifestyle and went back to just stripping. A few years later, she became part owner of the club and focused on managing the place.

Her career as an escort came to an end when Kimberly was on the verge of turning 30, and 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 part time 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, because of his active social life. But when he did, he always got a lap dance from Kimberly. She always asked about his latest sexual conquests, impressed with how much of a player he had become.

When Jeremy last saw her, he was relieved to hear that she had stopped prostitution, was attending school, and was looking for a regular job. As they talked, Jeremy finally did something he had always wanted to do, which was to ask her out. She agreed; he was a great guy and never judged her for her life. Three years later, they got married.

The End.