That time I had sex with four roommates and none of them knew or cared [MF]

Another fun story from my sexual past. I was a counselor at a summer camp in my mid-twenties, and if you’ve ever worked at a summer camp, you know how much of a fuck-fest those can be.

Anyway, we were all staying in a bunch of cabins in the veeeeery far back of the camp. Why weren’t counselors in the cabins? Well, we were relief counselors, which meant the bulk of our duties were running day activities, and we would step in for cabin counselors during their nights off, etc. I was bunking with 3 other guys, and the cabin next to us was 4 girls.

So this was a mixed-activities camp, so we had a wide variety of disciplines accounted for. I was a swimmer doing swim instruction and also taught the cross-country running stuff. I was at sort of the height of my fitness level, not a huge guy by any stretch—5’10”, but I was lean, like 150 lbs tops. It felt good. Onthe first day we were at orientation and I looked around and scoped out the landscape and the female counselors were ALL bloody attractive.

Imagine, if you will, from right to left: Martha, who was an arts/theater person. Whimsical, romantic. Dark hair, light hazel eyes, dark chocolate almost black hair, and just the cutest cheekiest face you can imagine.. she was short and had small but existent tits, a tight ass, and a slim waist, which meant she was smoking hot. But you might never know because she was often in the baggiest clothes and covered in paint.

The second girl from the right, Sarah, curly red hair, blue eyes, sort of typical Irish facial setup. The dance instructor. Also short, and kind of a fire cracker. She had dare I say a perfectly understated but sexy body—good, bouncy, B cup tits, enough ass to grab, and she had the kind of flat stomach only dancers have. Being a dancer, she also had some muscle poking out from underneath her clothes from time to time.

Then, Jessie– loud, confident, occasionally standoff-ish. The ‘fullest’ of the bunch, she was one of my fellow sports and swim people. She was INTENSE. Also short, long blonde hair, a thick muscular ass, small tits (she rarely wore a bra). I think she could have fought a bear to a stalemate. GODS I found her attractive. Anybody that can do 100 burpees without much effort deserves to catch a bone whenever she wants.

Last but not least, Kayla. The quiet, serious type. She was the camp photographer. She also short (maybe the shortest? Between her and Jessie), was a runner, and had That Runner Body™– strong ass and hips, lean frame, long curly medium brown hair that always seemed either in a ponytail or messed up, medium brown eyes. She was always wearing those athletic shorts, and sported that line that all runner girls have delineating their quad and the hammy. I liked that line a lot.

The funny thing is, none of them liked each other very much. They didn’t talk unless they needed to. They didn’t sit together. They didn’t eat together. They didn’t co-teach anything. And we were always so busy that they really just slept in the same space. Which is why it worked out that I could more-or-less be fucking all of them in the span of one short summer.

Jessie, the stout muscular blonde, was actually the first, and the only one I knew before being hired at the camp. I actually had dated a friend of hers and after we broke up, Jessie and I stayed in contact via the internet. We had a lot in common and we were probably both going into that summer pretty sure we would hook up, if not become a couple. And for all of her blonde athletic lustiness and confidence, she was probably the one with the least experience sexually—she had only been with a couple of people (so she told me). We fucked a couple of times that summer. The first was in an empty cabin room during orientation week. We both knew it was coming, we were both getting the flirty eyes and fireworks, touching ‘accidentally’ all week, etc. During the final orientation social, we walked out to look at the stars. We ended up exploring the camp a little bit… the cabin was really the first dark secluded place we found, and before we knew it we were making out. As we ripped each others’ clothes off, we started in missionary (fully condom’d, mind you), and eventually we flipped over and she rode the daylights out of me. I remember grabbing her amazing ass and just drilling her until she came hard, and how pointer her tiny little nipples got as she grabbed them and came on my cock calling my name. I think I might have been the first decent sex partner she had, because she was really into it. It was hard to stay quiet, because the rooms were really just plywood boxes, and we knew people would probably be able to hear it if we got too loud. Following our hookup, things got a little weird for most of the rest of the summer. We didn’t talk much, and never about the sex. We sort of hate-fucked one more time, the last night before leaving camp, her bent over a piano in the instrumental practice rooms. I haven’t talked to her since.

The second was Sarah, the redhead dancer. To be fair, she was mostly retired of dancing, having suffered some kind of injury at some point. But she was still fit as a fiddle. This one started innocently enough—pokes in the dark concert hall as we sat together, elbows touching, little physical gestures. I wasn’t sure about her at first because she was an odd duck and had a little bit of the crazy eyes… but then I saw her in a bikini and knew that if I had the opportunity, it would be worth the risk. We fucked quite a bit throughout the summer, but the first time was an evening more-or-less off. We had already made out a couple of times, and I had discovered a door in the camp theater that had some cool safety lighting in the pit that I knew would be a lot of fun after a couple of weeks of camp goggles. I knew that nobody would be there at that time of night, and it was so far back in the woods as to not draw unwanted attention, so I said, “Hey Sarah, want to see something cool?” So off we went. I showed her around a little bit then flipped the safety lighting onstage and before I knew it her mouth was wrapped around my dick like it was a popsicle. The best thing about Sarah was that she knew EXACTLY what she wanted… within moments of starting the blowjob, she had pulled her tanktop and bra over her head to reveal her nay perfect B cup tits, and between slurps told me she wanted me to cum all over them. I nearly came right then and there, as I had never been with a proper cumslut before. A few minutes of her magical mouth later, sure enough, I exploded all over her magnificent breasts. Before cleaning up, she asked if I was able/willing to keep going, which I was. The stage was set up with a prop platform that just happened to be perfect height for fucking, so she sat on it, pulled off her jeans, and took me in bareback (we had already established she was on birth control and that we were both clean). She came quickly, and to my surprise, I felt a second one bubbling up. She felt my pace quicken, and when I started to really go, she pulled me out, jumped off the platform, put my cock in her mouth, started massaging my balls, and took my head in and out of her tongue until my second load of cum had dripped down the back of her throat, moaning the whole time. I still remember her swallowing, looking up at me, and smiling. She was my most consistent booty call throughout the summer, and we fucked a lot. On the pianos. In the shared shower. Even once in the guy’s cabin (someone walked in on us and left VERY quickly). I think she enjoyed knowing how much her tits turned me on. She always wore low-cut shirts and sent a lot of dirty text messages to me in the middle of class.

Kayla was an interesting case. She came to camp with her boyfriend, who was a music instructor. In fact, they were both musicians. The first thing anybody thought of when they saw Kayla was that she could easily pass for a young Natalie Portman, with generally curlier hair, and somehow hotter. As the summer dragged on, Kayla and I started to get to know each other better because we had a security patrol together a few times per week. We had a lot of time to walk around and talked about a lot of things while we did it. I really thought of her as a friend more than anything, but there was no question I was attracted to her. I just thought she was monogamous and that was that. I’m not a predator, after all. I am open about my sexual life to my friends and was clear with every single one of them that I was not into monogamous relationships at the time… it was all in good fun and I wanted it to stay that way. So we kept it to casual frienship. That was, until she found out her boyfriend had cheated on her. Why? I’m not sure, because she was the sweetest, most honest, gentle person. Then I found out they had been dating for *seven years*. That is, like, common law married! So props to her for staying at camp. I would have probably quit. But she didn’t. She beasted through it… but one night toward the end she called me to talk. She said she had only ever told me about herself and her problems (which was not true, but I am a flexible listener), and that she wanted to know more about me. So we met up after our respective duties and I told her a bit about myself. Not particularly interesting, but I have lived in a lot of different cities, so I told her about that. At some point, she kissed me. Taken aback, I was worried about her, and asked what her intentions were, asked if this is really what she wanted, tried to break the spell. But she said, “soon camp will be over. Let’s be honest, I will probably never see you again. I’ve only been with one person for the last seven years. I knew I wanted this when we first met, but I’m no cheater, so I ignored it. Now I can have it.” So we went to the adult pool complex across the street from the main camp, jumped in sans clothes, and we came together in five feet of water.

Finally, the last roommate, and the only one I had any inkling of actual long-term interest in. Martha. What an interesting case she was. As we were all nearing the end of camp, eight weeks of very close living, it began to weigh on all of us 20-somethings that this was it. If we were going to make a move, it needed to be now, because we were out of time. Not many people knew how hot Martha really was. Think brunette Elisha Cuthbert. Smolderingly attractive, super seductive eyes. But Martha had one big drawback. She happened to be the girl that Kayla’s boyfriend cheated with, and her tragic flaw was that she *relished* being the archetypal mistress. She had done it to a lot of men and women, and it worked so well because she was just so goddamn charming. Martha and I had been light-flirting all summer. We did a lot of back rubs, shoulder rubs, neck rubs, etc. I’m all about that shit. Sex isn’t everything. The flirting is almost as fun, sometimes more fun. But I kind of wanted to be the one that didn’t give into her charm, so I always just walked away when the moment arose. Sometimes you just gotta burn a card, you know? Plus, I was single, so she couldn’t be the mistress of my life. No harm no foul. Well, the last week of camp rolled around and we were all starting to feel the burn of real life encroaching. Our crotches were doing a lot of that thinking for us. On the campers’ last night was a dance/mixer thing and our job was to walk around and make sure they weren’t getting too hanky panky in the woods, and of course I was paired with Martha. So we were alone walking a dark tree line, in the middle of nowhere, on a clear night with stars shining, shooting the breeze and we stopped for a second and made sultry, sexy, I-want-you eye contact. Then we kissed. Fuck off and get to the sex right? Well we didn’t actually have sex at camp. It wasn’t until a couple of weeks later, Martha and I were chatting on Facebook and it came out that we both kind of had a secret crush on each other.

We ended up sexting a lot, and she sent me nude photos which nobody had ever done for me before or since. That was surprisingly a big turn-on… that kind of trust and interest. She suggested I come out to the east coast for a visit, which was like a 12 hour drive but you know what a guy will do for sex.. and so I did. I assume everybody knows what junk smells like after 12 hours in a car, so immediately upon arriving, we kiss, then I ask if I can rinse off in the shower. She obliged and I commenced. A few minutes into my shower, well, you know where this is going, I was really into the hot water with my eyes closed when I felt a cold draft… the next thing I know, Martha’s hands are all over me and her naked hard nipples were pressed up against my back. She reached down and started rubbing my dick and I could have died a happy man then and there. But she kept rubbing and rubbing until I was hard as a block of wood. She came around to the front and oh my god was her body perfect… the pictures didn’t do it justice. Small, perky pierced tits, curvy hips, the perfect grabbing ass… she had a classic pin-up look to her. She dropped to her knees and started licking my cock, telling me how much she likes feeling me throb in her mouth. As I was getting really close, she stopped sucking, stood up, turned the shower off, and walked me over to the bed. She then laid me down, got on top, and slid my cock gently into her soaking wet pussy with her hand, her face telling me just how much she liked it. She took it slowly up and down and I could feel her juices flowing down my cock. I probably almost came twice and each time she could tell and slowed down momentarily. Then as she started to get close and speed up, she leaned back and all of those beautiful ribby abdominal lines popped out as she began to contract into a screaming orgasm. I could feel her pussy clench and unclench on my cock and the sound of her coming sent me over the edge. I tapped on her and she jumped off, pumping my dick as a deluge of cum landed one rope at a time across her collar bone, her tits, her neck, her stomach, and her pussy. Before I could catch my breath, she began taking me back in, pumping for a couple of thrusts, then pulling out and using my cock as her own personal dildo on her clit. When it was clear I was going to stay hard, she put my cock back in and started rocking back and forth, faster and faster, until she came a second time, grabbing the sheets and my legs in orgasmic ecstasy.

I stayed a few sex-filled days then had to go back to school. We continued to sext, but eventually we just fell out of touch. I think she got a boyfriend and became monogamous. I often wonder how she’s doing. Probably the hottest girl I ever really had a chance with. I wanted to tell you more about that one because she took a lot more work than the others and is one of the more interesting people I’ve met.

So that was the summer I had sex with all four roommates without them knowing (or caring). Definitely the most sex I’ve had with the most people in a relatively short amount of time.

What should I write about next? There was a time I had sex with a girl who turned out to be cheating on her boyfriend with me (which is TERRIBLE and IMMORAL ^(and sort of gratifying)). There was a time I fucked the college dean’s daughter in the back room of a bar after hours. Then there was the time I hooked up with who is now one of the most famous concert violinists in the world.

Source: reddit.com/r/gonewildstories/comments/bfw3nd/that_time_i_had_sex_with_four_roommates_and_none

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