A few years ago I met a wonderful girl, Jessica. She was a friend of my then roommate’s girlfriend, and she and I hit it off after hanging out as a group a few times.

Jessica and I were both very sexually charged and our first date ended with her getting fingered in the front seat of my car in a mall parking lot and our relationship quickly escalated from there. We experimented with every new and exciting kink we could think of, including swinging and threesomes, both mff and mfm, and bondage.

The sex was amazing, but the relationship wasn’t and we broke up. We weren’t on bad terms with each other after that, but we didn’t talk much for awhile. We started talking again a few months later and that escalated into a string of hookups. Since then, every once in awhile we go through a period where we start to fuck frequently before cooling off for awhile.

During one such period, Jessica got really into rape roleplay. We’d acted out scenarios plenty of times, so this wasn’t odd, but she started wanting it every time we met up. Finally, she confided in me that she was fantasizing about being ravaged by a man she didn’t know and didn’t trust.

I started to bring this up when we played. I’d tell her things like, “Maybe next time I’ll invite some men over after I tie you up and gag you. I’ll leave you with them and take a drive and there’ll be no one here to stop them from doing whatever they want.”

Jessica would always respond positively and I considered doing just that several times but never did, until Jessica pushed the situation. She told me she wanted me to find someone to rape her. She didn’t want to know when it would happen, but preferably soon because she might back out otherwise. We had some very rough sex that night and I made sure to tell her how I couldn’t believe what a slut she was. She deserved what was coming to her.

So I had to find a guy. I’d used craigslist before (to find couples) and I started there, making a mw4m post, teasing at a rape scenario. “I’m looking for a well-endowed, gl/hwp /ddf man to surprise my gf with. She enjoys rough sex with hung dominant men.”

Most of the men on craigslist are not inspiring, I talked to a few but nothing came of it. A couple were promising, but unfortunately flaky.

However, I decided to go a different route. There’s a swinger’s club I sometimes visit in San Diego. Unlike many, they allow in single men and there’s always plenty of horny dudes looking to swarm any woman that will let them. Perfect.

I visit Saturday night, and like always, plenty of dudes. A see a few that are just sitting around awkwardly, there’s a firepit and some chairs, and not much going on because it’s still kind of early. One guy seems like someone Jessica would be interested in. A bit taller than me and more muscular, and with a flaccid but probably above average cock. He’s seems to be about my age (late 20s) and a little older than Jessica (mid 20s).

I ask him how his luck’s going, and he’d gotten a hand job earlier, but not laid tonight yet. He said yet. Lol. His name’s Josh. We chat for a bit and get on the topic of some the kinky shit people are into and I bring up my friend Jessica to him and what she’s into. I tell him to catch me when he’s leaving and I’ll head out with him and show him some pics. No phones are allowed at the party, they have to be left in lockers.

So I enjoy myself until about 2, when I Josh catches up with me and tell’s me he’s leaving. I tell him, “Cool, me too.” And we both go to get dressed.

Outside, I ask him if he wants to see the pics and he says fuck yes.

I just realized I never described Jessica. She’s 5′3″, B cup. Slender and maybe 100-110 pounds, with a toned body from running on the treadmill.

I showed Josh a few pics from our kinkier adventures. Jessica with mine and a friends cocks in her mouth. Another of her face covered in cum. Tied up with a vibrator strapped between her legs, etc.

Then I asked if he was interested and he said fuck yes he was. So I got his number and told him we’d talk about it more later.

I texted him the next day and asked if he was still interested.

He was but he was kind of worried if I was sure she was into it. I told him I’d figure something out so he could be sure. I texted Jessica a request. She got back to me quickly with a picture of herself naked with, “Rape me, J” written on her chest, which I forwarded to him. She had questions about it, but I told her she didn’t get to know.

I keep in touch with Josh thoughout the week. I also get a photo of his license just in case. I make plans with Jessica Friday night. We go out clubbing and drinking. I tell her I’m taking it easy because I’m driving and meanwhile encourage her to down as many as she can, which is really about 3-4 and she’s plastered. We’re dancing and grinding and she’s drinking and by about 1 o clock , she’s at her limit, stumbling and giggling constantly.

We head outside and start walking to my car. We got the club a bit late and had to park far away as a result. Jessica’s in heels and basically need to be dragged, so I tell her to sit down on the curb and I’ll run and grab the car. She’s not really in a situation to disagree, so she half sits half falls down.

I left her there. I didn’t see her again that night. I got in my car, texted Josh who was waiting near by and I went home.

I get home and stay awake wondering what’s happening. Around 2:30 Josh texts me a picture. Jessica is laying on a hotel bed her eyes open but glossy. Her hair is messed up and her make up is smeared. She’s completely naked and her legs are open and she has red marks on her body.

Josh tells me he’ll send me more tomorrow, and I jerk off and finally get to sleep.

Sure enough, I text Jessica the next morning to see how things are going and I get texts back from Josh instead. More pictures. Jessica getting chocked and gagged with Josh’s dick. Jessica laying on the floor with cum on her tits and whore written on her face.

Later I get a message from Jessica. She’s back home and she’ll tell me about her night later, but she wants to sleep.

The next time I get her side of the story, she was really confused because she was drunk, but was also really horny because she’d been imagining getting taken advantage of so long. The sex kind of hurt a bit because she wasn’t very wet when he went in, but she got wet very quickly afterward. He’d come inside of her and while she didn’t come herself it did feel good, even when it hurt.

She didn’t know if she’d try it again, but she was really happy with the experience. As far as I know she hasn’t done anything like it since, though we do still roleplay sometimes when we meet up.