Note: This story takes place more than twenty years ago, when the internet and cell phones hadn’t completely taken over yet.
I’d met Elle when she’d come to one of my amateur boxing matches, right after college. I’d noticed her in the audience, eyes bright and intent on the fight, and noticed her again, in the bar afterwards that the boxers, trainers, and fight fans tended to go to. I was brimming with post-fight energy; it was the first fight she’d seen, a mutual friend from college had invited her. She told me she had been prepared to be shocked or horrified, but instead just found herself elated and thrilled. The excitement made her even more attractive than she already was; she had a clever, laughing face with girl-next-door charm, and a smokeshow body, smooth curves on top of an athletic frame. Honey brown hair, dazzling blue eyes, and a really rich laugh that charmed me right away. Talking about the physical reality of fighting turned into flirtation, which turned into making out in the street as we stumbled back to my place. It was a pretty intensely sexual relationship from the start; we talked about plenty of other things, but sex was our punctuation, our rising and setting sun. We established quickly we weren’t looking for monogamy–she tested that out within a couple weeks, telling me she’d fucked another guy, and was pleasantly surprised when that got no jealousy from me, just made me fuck her harder. A month or so after that, we had a MFM threesome; she looked incredibly hot during that, her gorgeous body overwhelmed with pleasure.
We talked about kink and fantasy a lot–that’s what had led to the MFM. One fantasy she liked to return to, to speculate about, was being paid for sex–being paid a lot for sex, specifically. So, I told her about my friend Charlie’s hotel bar—I was a bartender at the time too, and had met him at a previous job. I had visited him at his new job at this swanky hotel, and, when he was busy, wound up talking to a charming young woman at the bar. She was wearing a stellar outfit but although she participated smoothly in the conversation, she seemed a little distracted as well, eyes scanning the room. After ten or so minutes of that, Charlie called me over to the side on the pretext of meeting one of the other bartenders, and told me that girl was a ‘call girl’, and that I shouldn’t waste her time. I laughed, and thanked him. Later that night, I saw the girl leave the room with a man, and it was a nice little jolt of ‘wow, that really happens here.
When I told the story to my Elle , she was so intrigued by it. She asked questions about what the girl was like, how she was dressed, what her attitude was. I told her about the short, tight, but elegant skirt, the silk blouse open enough to show a diamond necklace nestling between her breasts, the dark, sinful shade of lipstick the girl wore. She asked me to ask Charlie if that was a frequent occurrence at the bar. He said yes, and that made her really want to visit and see it all in person. I took her there, and she watched the couple of women who were ‘working’ that night, fascinated. She gripped my thigh in excitement when she saw, after an hour or so, a young woman leave the room with a silver-haired man, heading for the elevators.
When we got back to her place after that night at the hotel bar, she told me “Fuck me like you paid for me.” It was amazing, intense sex from the start: She went down to her knees at my slightest touch, gagged on my cock like she never had before, and when we fucked, came really hard for me right after I told her that’s what I’d paid to see.
It turned into a regular thing with us, going to that hotel bar, seeing the girls, and then fucking after. She made friends with one girl, “Clarice”. Elle talked to her about her rates, how she handled negotiations. After about four months or so of going there, she told me she really wanted to do it. To try getting paid for sex. To be, bluntly, a whore, a high-paid whore– but that she needed me to help her feel secure in it.
I talked with Charlie about it—he was a very nonjudgmental gay dude, and had zero problems with sex workers or kink, and combined that with what her friend had said. He explained that the girls there mostly worked for escort agencies, and they’d have the johns call the agencies to confirm the ‘date’ when they got to the room. It was a fancy hotel, and they weren’t really worried about guys getting physical before the call, and once they’d called, it could be traced back to them. So, accountability, some margin for safety.
She went shopping with her friend, who dressed her in a knockout outfit that wasn’t overly obvious but let her flash a ton of leg, to lean to show deep cleavage, and she looked expensive, too. She and I talked more about this–I hadn’t totally been sure if she really wanted to go through with it or just go up to the edge, to buy the clothes, to imagine herself in the role. But the more she did to prepare, the more she wanted to completely fulfill the fantasy. We set a date.
We came to the bar together, but she took a moment and walked in after me, so it wouldn’t seem like we were together. She was amazing at how coolly and quickly she slid into character. Sitting at the bar with just the right half-open pose towards the door, catching the sight of men who walked in, just as her friend had taught her. Her long legs looked amazing in the classic red heels she wore, her hair was up on her head in a way that looked elegant but inviting at the same time, expensive but clearly designed to allure. She had a necklace of pearls and silk, in a choker motif. There wasn’t any other girl working that night, so there was no drama, and she attracted attention quickly.
It only took about forty-five minutes before a man approached her. He had salt-and-pepper hair, a very nicely cut suit in a dark fabric. He looked fit, robust, and his attitude was confident and calm; he offered an immediate compliment on her necklace. I was sitting nearby; the plan was that if I felt any bad vibes, I could intervene, but I didn’t. He seemed to know what he was doing, and to not have any hostility or strangeness in him, just a hunger.
I gave her space, went to the other end of the bar and chatted with Charlie, until about twenty minutes later, she and her new friend left the bar. I went to the room that Charlie had made available to me, just on the second floor, up the stairs. A few minutes later, the phone rang, and I answered it as “Slade Escorts”. The guy said that he was with Elena, and wanted to engage her services for the night. I told him that would be fine, but did he mean several hours, or the night. He clarified that he’d like four hours of her time, and I told him the cost for that would be a round thousand dollars. He didn’t hesitate in saying that that would be fine. I told him to have a very good night, and to call with any problems.
I was strangely calm from the start. After I hung up the phone, I managed to just read a book for a little while, before my mind eventually turned to what she might be doing. I spent the next couple hours in a nice semi-aroused state. After the four hours, she slipped into the room.
She was glowing; she looked tired, too, in a wonderful way. Satiated and tired, but also excited. She had put her heels back on, redone her makeup a little, but it was still somewhat smudged, her hair was tousled and damp, hanging loose, fancy no more. I embraced her, and she put her hands on my chest and said, “Thank you.” Which was sweet, and incongruous.
She got wine from the minibar, and poured a glass, and drank half of it, savoring it. She sat on the bed, and I sat next to her, and put my hand on her thigh. She parted her legs, so readily, so willingly, and I ran my hand up her thigh and stroked her, as she started to tell me what had happened. Her voice was husky, full of thrill and wonder at herself.
“For the first half hour, we talked. He asked a mixture of personal and sexual questions. I lied about having done this more often, but did say I was quite new, and that excited him, and it was so hot to see how excited he was by that. I told him condoms were a rule, and he agreed readily.”
As my hands slid along her thighs, coming close to her pussy and retreating, wanting to allow her concentration, she continued. She said he wanted to know if she used sex toys, if she’d been with women, and she answered those honestly and forthrightly. Then he had her strip for him, to take off the dress she was in and reveal the very slutty lingerie that her friend had picked out for her. He asked her to pose for him, to press herself against the wall and look over her shoulder, to bend at the waist in front of him. Then, to straddle his thigh.
He put his hands on her ass then, the first directly sexual touch, and kissed her. And then he told her that he wasn’t looking for ‘girlfriend experience’, that this was sex, pure sex for him. That knowing things about her made it hotter, but that it was all about having her do what he wanted. She smiled in response to that, since it was so exactly what her fantasy wanted, and told me that was when her arousal first started to really climb, to begin building a pressure inside her that would continue throughout the evening.
He had her take her bra off, and complimented her on her cute upturned breasts—they were very, very cute, the way her nipples jutted up at such a sharp angle. And started to suck on them, to fondle them, with a really firm grasp, an assumption of rights. She started to get wet for him just from that, and he noticed that. He put one hand back to her ass, and helped her move on his thigh. She said his eyes widened, and he said “Fuck, you’re so into this,” and she nodded and said, “I am.”
That really excited him. He pulled her along his thigh some more, and then told her to get on her knees, unbuckling his belt and sitting in a chair. He told her to suck his cock like she loved it and was being paid for it, both of which were true. And she dedicated herself to it, she said she gave him a blowjob that was as enthusiastic as she’d ever given. He sat back and let her work at first but then held her head and pumped her mouth on his cock. He told her she was so good at this, that he knew she would be. He’d have her stop, at times, and bring her up for a kiss, or to drag her tits along his body, and then send her back down to resume her work. She did everything she’d ever done that had excited a man, many, many things she’d done with me–pressing her tongue up under his cock as he sluiced it into her mouth, hollowing her cheeks and sucking hard around just the head. Looking up at him to make eye contact and smiling. Humming around the shaft as she challenged the back of her throat with it.
He told her to suck his balls, and she put her face under his cock, let it rest on her that way, and eagerly sucked them. She remembered, doing that, how much older he was than her, and that sent a thrill in her too, the image of herself, so young, kneeling and blessed by his cock and paid for it. With his balls in her mouth, and his cock on her face, he offered her $500 extra to fuck her ass. And she nodded, happily. He got out his wallet then, and counted out the full amount, and put it down on a table next to the chair. A thousand five hundred dollars.
She said her pussy got so, so wet hearing the bills rustle while she sucked his balls and jerked his cock. He had her go back to sucking it for a while, and then pulled her up. He told her to get on the bed, lying on her back with her legs hanging off it and spread. She did, heart hammering. He put a condom on, and got between her thighs, standing at the edge of the bed. The beds in this hotel were the perfect high for him, and she wondered how often he’d done this. He grabbed her amazing tits in his hands, and pushed his cock into her. Not slowly, not rushing it, just a steady constant pressure.
She writhed in pleasure, and said his face was so lit up at seeing her clearly love it. He put pushing until h e was all the way in—he had a decent-sized cock—and he said “It’s so much better when the whore is an enthusiastic fuck.” And the way he said it was genuine, warm, not like trying to be a jerk. She put her hands on his chest and said, “Fuck me. Fuck me hard.”
He started pounding her like that, he’d go rough and hard for like ten minutes and then pull his cock out, slap it on top of her pussy, cool down. He liked to just look down at her like that, and she said she felt so exposed, vibrating with the knowledge that there were still hours left.
After about a literal hour of that, he finally asked if she had lube. We’d thought ahead, so she did. He brought her her purse—she remembered thinking that was sweet, to not root through it but give it to her, and she got out the lube. He put it on his cock, and pushed her legs further apart. He lubed up his fingers, and pushed one, then two into her ass. She relaxed herself as he entered, and said it was the easiest her ass has ever taken anything, she was so ready for it.
What she wasn’t ready for was that he rubbed her clit as he started to fingerfuck her ass, which made her yelp in pleasure. Experienced fingers sliding over her hard little nub. She bit her lip and moaned under his ministrations to her pussy and ass, as he started talking dirtier to her than he had. That she looked like such a slut on her back like that, ready to give up her ass to a man she’d just met for money. And she got wetter and wetter from that. She came for him, like that, almost out of nowhere, without knowing it was going to happen. She felt the need to tell him, to say, “I’m coming,” and invite him to watch closely
That made him wild with need, and after she groaned herself to a shaking quiet, he pulled his fingers out of her ass and lined his cock up. He held her thighs back—her still on her back, same position, basically—and pushed the head of his cock in. Anal was something that Elle liked a lot, and we had done quite a lot of it. She was able to play the experienced slut here, and she reached down and spread her ass in her hands and said “You can really fuck me like this”
He took her at her word, and started to pump her ass. Grabbing her tits again as a handhold. Gritting his teeth and telling her that her ass felt fucking incredible. She loved the way his big hands felt manhandling her breasts, she half-sat up to look down at her exposed pussy, at his big body between her thighs.
He was growling and groaning and calling her a good slut and that she was worth all the money he was spending on her. When he put one hand back down on her pussy, his thumb working her clit, she came again for him, not able to speak this time but rolling her eyes back and shaking. That drove him crazy, he fucked her ass hard as she was coming, his own voice becoming wild and incoherent. While she was still in the trailing throes of the orgasm he pulled out of her ass, stripped the condom off, and came all over her stomach and tits. She looked up to see it, and a little splashed on her cheek, but most of it launched onto her belly and breasts. She could see the wet length of his cock jerk as it pulsed the load of cum she’d earned onto her.
He put his arms on either side of her and just hung over her for a few minutes, gathering himself, panting. Then he told her that she could go shower. There was still like, an hour and a half or so on the clock. She sat up, and he kissed her, pretty hard, not like, some tender ‘That was sweet’ kiss but a ‘that was the fuck I needed’ kiss. She went to the shower, and she even put her hand on her pussy in there and played with herself, running back what had happened. She was still so aroused.
When she finished showering and drying off, she came out in the nice fluffy hotel bathrobe. He told her to put her makeup back on, in the main room, while he showered. She did, sitting at the little vanity table. He came back out of the shower naked, and told her to put back on her lingerie and dress. She did, and looked almost as fresh as she had in the bar earlier.
Then he had her get down on her knees, and put his hand in her hair. She opened her mouth without being told, and he slid his cock in it, and she went to work again on it. He looked down at her, and she raised her eyes to his, and he told her how good it had been to fuck her ass. How he was sorry he had to leave tomorrow because she was so worth another thousand or two for more. As his cock hit the back of her throat, he told her that he was tipping her an extra $500, and she put her hands on his thighs and facefucked herself onto his cock as much as she could.
He came pretty quickly, in her mouth, her eager throat taking it down as he did, and she looked up at him with his cock on her tongue after. He gave a deep, satisfied sigh, and pulled out. He went to his pants–she remembered being impressed at how casual he was naked, most guys are a little shy about it–got his wallet out again, and put another $500 down. He got dressed, telling her again that she’d been seriously amazing, and asked how to get in touch with her if he was in town again in the future. We didn’t have any business cards or anything like that made up, and this was in the pre-cell phone era, so she told him to ask Charlie to get in touch.
For the last half hour or so, he had her sit on his lap and tell him more of her sexual adventures, and she told him a lot about sex with me, but not that she was going to go right to my room after.
As soon as she finished telling me this story—I’d been teasing her pussy at times, but mostly letting her concentrate— I pushed her back on the bed, in her pretty dress, and parted her thighs. I pulled out my cock, and pushed into her—the second man to be in her in such a short time.
I fucked her hard, I put my hand on her throat and called her such a natural little whore, a perfect fucktoy for this complete stranger, how she’d rocked his world, and showed him such a slutty side of herself. Every word was a compliment.
And she said “I need to be filled, Tom,” and I just owned her little pussy until I felt my orgasm hit, like cannon fire, I just detonated inside her, pouring cum into her.
We were looking into each other’s eyes when I came.
Source: reddit.com/r/eroticliterature/comments/v804ph/high_prices_are_part_of_the_kink_mf_prostitution
This is one seriously hot experience
Very hot story. Is there more stories of her?