This is my first story, not too taboo. Hope you like it
'What am I doing here?' That was all he was able to think to himself. He was eighteen, young, kind of nerdy. The reason he was walking around downtown was simple. He was a virgin, and he didn't want to be anymore. He figured he might as well just lose it to a prostitute, not like he was going to convince a girl to go out with him let alone sleep with him.
He looked around, seeing a few women he assumed were prostitutes but them looking very... Old. He knew he had no place to be picky, but he rather his first not be a heroine addict with herpes. He actually didn't want his first to be a prostitute at all, but there he was. He knew he could probably go online and find someone there, but he didn't know anything about ordering a prostitute, if ordering was the right word.
So there he was, wandering around the downtown streets. He kept trying to justify it to himself, telling himself that it was what they did hundreds of years ago. They would take their sons to a prostitute, give her ten dollars and tell him to go wild.
He was about to give up when he turned and saw a girl, a woman. She was dressed like the others, short jean skirt, almost see through tank top that only barely covered her chest. She was very attractive, long brown hair, darker brown eyes, quite tall with large breasts and long legs. She would be perfect if she was cleaned up, but she was obviously another street rat, or whatever they called them.
After a moment she glanced up at him and then walked over, her hips shaking as she walked. He was almost entranced by her, even though he technically didn't know if she was even a prostitute. Seemed too good to be true.
“You alright there?” She asked and smirked. “Like what you see?”
He nodded and then cleared his head. Come on, stop acting like an idiot! He told himself and then looked at her. “Yeah.”
“Haven't seen you around here much, come here often? Or just passing through?” She asked, almost ironically given they stood at a street corner.
He ran his hand through his black hair. “Not often...”
“Looking for someone, or something in particular?” She asked and he nodded. After a second of him not talking she smiled. “Am I what you're looking for?”
He thought for a moment. He didn't want to in some way offend her, again he had no idea how to handle a prostitute. If they even did get offended. But she could just be some random girl in the street, and it would be horrible if she was and he called her a slut basically.
“You don't do this often, do you?” She asked, not waiting for a response. “Well, I charge fifty per hour. And that's just normal stuff.”
Fifty an hour seemed cheap, and considering he had five times that he was in. “Yeah, okay.”
“Got a place in mind?” She asked and he shook his head. “Come on, I know a place. It will be good enough.
He couldn't believe that he was actually following a prostitute and was about to have sex with her. He was sure when he woke up in the morning that he would back out. He would get downtown, hang around a little bit and then go home. Actually, two minutes before meeting her he was sure he would back out.
“What's your name?” She looked at him as they walk, approaching a small hotel.
“Ian. You?” He asked and looked over the building. He had been in it once before, it was pretty dirty and run down, but he really didn't care at this point.
“Call me Sunny.” She said and walked inside.
They got a room and then went up, both going into the room and shutting the door. She almost immediately took off her shirt, revealing two large C-cup breasts hidden under a purple and black bra. She walked over to him and took off his shirt as he stared at her chest.
“You a virgin?” She asked and he looked at her, surprised. “I don't judge. You guys are more fun... Guys who have done it with everyone always want something kinky.”
He swallowed and nodded. “Yeah, I'm a virgin.”
She took his hand and lead it to her breast, knowing he wouldn't do it himself. She then reaches back and undoes her bra as he starts to work on her breast. She couldn't help but let a moan escape her lips as he played with her, lightly rubbing his thumb over her erect nipple. She leaned in and then kissed him deeply.
He had kissed a girl before, a few actually. This wasn't new. He held her close, rubbing her back as his tongue slipped into her mouth. He broke the kiss and started to kiss down her neck, lightly nipping at the skin. She started to get wet, taking off her skirt as he kissed, standing only in her panties now. He kissed down her neck and got to her breast.
He began to tease her a little bit, tracing circles with his tongue around her nipple. He didn't know if what he was doing was right until she moaned, stroking the back of his head. She had no idea why he was doing it, trying to turn her on so much. She was being paid to give him pleasure.
She pushes him away and then sits him on the bed, taking off his jeans and boxers, revealing his hard cock. It was surprisingly big, six inches and quite thick. She lightly glides her finger tips across his shaft and he groans and leans his head back. Her cock twitched, releasing some pre cum. She knew virgins never lasted long, and he would probably not be the exception.
She licked up his length, making him shudder with pleasure. She takes his head into her mouth, her tongue twirling around the tip, closing her eyes and going down on him until his tip touched the back of her throat. She began to play with his balls in her hand, sucking his cock at the same time.
He watched her, still not fully believing that it was happening. To him she was very sexy, and now she was sucking his cock. He wanted to fuck her so badly, but wouldn't object to a blow job, figuring that either way he was getting off with something other than his hand.
After a minute she sped up and he felt himself getting closer to an orgasm. He looked down at her, panting. “I'm going to cum soon Sunny.” He moans as his cock twitches and he shoots his load into the back of her throat.
She swallowed it and then ggot up and took off her panties. “Gotta get you hard again then.” She said and walked over to him. He took her and then threw her down onto the bed. She didn't expect it, not from him. He leans down and then licks her slit, causing her to moan loudly. Guys rarely ate her out, she rarely ever had orgasms because of it.
He knew very little about how to make a girl have an orgasm, only knowing a little bit from stories online. He was moving her hips to his face though, so he figured he was doing a good job. He played with her clit with his tongue, penetrating her. He moved his hand up and started to finger her, using one finger at first and then moving it up to two.
She felt the waves of an orgasm washing over her as her body shook for a moment. “Oh my god!” She yelled as she had an orgasm, her juices coating his finger.
She looked down at him. “What was that?”
“Sorry, I didn't mean to-”
She smiled lightly, panting. “No, it was good... Lay down.”
He didn't argue, just laying down on the bed. She climbs on top of him, positioning his once again stiff cock at her entrance. She lowered herself down onto him, and then paused.
He was no longer a virgin. He looked up at her and she leans down, kissing him. They held the kiss for a few moment before she started to move herself up and down on his cock. Her tight pussy walls gripped onto his cock, and it took a lot of energy to try and keep from cumming, him wanting to make it last as long as possible.
She started out slow, bouncing up and down on him. It was very sexy to see her on top of him, riding him cowboy style. Her large breasts moved with the rest of her body. The friction between his cock and her pussy was driving them both mad, their groans filling the room.
He could only hold out for five minutes before having his second orgasm. He filled her up with cum, her pussy now dripping with a mixture of both their juices. They look at each other, both panting, both satisfied.
“We should do this again.” She pants and then kisses him, laying on top of him, her naked breasts pushing against his chest.
Even though she was a prostitute, he did want to do it again. They both got up and got dressed, he went home and she went back to the street corner, back to work.