1. Ted, 26
I had a girlfriend who did not want kids, hated kids, and made it clear that the very thought of getting pregnant disgusted her. Still, she always insisted that we have unprotected sex, and even weirder, she always wound up begging me to cum in her. “Are you sure?” I’d ask, and she’d say, “Yes, please, cum in me and give me a baby!” So I would. And every time, right after cleaning up, she’d rush to the drugstore for a morning-after pill and be bitchy and have cramps for the next few days.
2. Jack, 29
I brought this girl back to my apartment after the bar and halfway through, she dove into her purse and took out these mardi gras beads. Wrapped them around my neck and started choking me lightly. She was on top and kind of had me pinned, easily could’ve choked me to death. Honestly, kinda liked it.
3. Claire, 23
When I was in college, I would make extra money now and then from sugar daddies that I would meet on special websites. Most of them were really normal and just kind of lonely rich guys, but one of them would bring me clothes he wanted me to wear on our dates, and tell me to style my hair a certain way. It turned out those clothes belonged to his stepdaughter, and that’s how she wore her hair. He wanted to fuck his stepdaughter, so he was taking the next best thing. I wanted to call the cops on him, but I would have been outed for being a sugar baby, and it wasn’t worth it.
4. Sam, 27
I was seeing this girl who was really into being degraded, which I’m also into, to a point. But she made me realize that I definitely had my limits when we were having sex one night and told me she wanted me to spit in her mouth and call her a bitch. Like, I’m into a little pain/pleasure, but that is just unsanitary and gross.
5. Jessica, 26
I was in my mid-teens and going down on my big athlete boyfriend. First problem: He had so much testosterone that he was very hairy “down there” and considered it unmanly to shave any of it off. Second problem: I was wearing braces. His pubes got caught in my braces. He had to pretty much hop over to my dresser, with my mouth attached to him, to get some scissors and cut me loose.
6. Ralph, 26
About a year ago, to demonstrate that I wasn’t performing up to her standards, my ex started texting while we were having sex. In her defense we were both pretty wasted at the time and she apologized profusely for the next few days, but it ended up being best for everyone and we ended things a few weeks later. I still don’t know who she was texting or what about, but I feel like I’m better off not knowing.
7. Julia, 30
I used to date this guy who was honestly the best husband material someone could hope for, except for the fact that he clearly learned some bad habits from porn that he could not shake. No matter how many times I told him that the key to female orgasm was ‘steady, repetitive movements,’ he would change positions every 30 seconds into these really awkward, showy positions and pound away. At one point, just before orgasm, he picked me up in an attempt to bring me to the mirror to make me look during doggy style, and dropped me on the floor from, like, three feet of height. I threw out my back and broke up with him from my bed the next afternoon.
8. Natalie, 22
He asked me to spit on him and slap his face while I rode on top of him.
9. Jordan, 24
I was fucking my girlfriend missionary-style (I’m Catholic), and she started shaking particularly hard. I assumed she was having a strong orgasm. I assumed wrong.
She was having a seizure.
She went from shaking very hard to complete unconsciousness. I, naturally, lost my erection and began panicking. I checked her pulse and her breathing, and she was alive. So I sat there cuddling her and stroking her for what seemed like an eternity but was probably about 20 minutes. She eventually came to but was very groggy and slurred her speech for about a straight hour.
It sort of put the damper on all future sexual relations between us.
10. Jason, 27
I asked my then-girlfriend to tie me up and tickle my feet while roleplaying as slave and master. She gagged me and tickled my feet until I ended up pissing myself. That wasn’t cool.
11. Lily, 24
We were having sex in our room when the door opened — we both stopped to see who or what it was. It was his dog, and the guy I was seeing said, “Don’t worry about him, he’s just curious.” I ended it right there.
12. Etta, 31
I had a boyfriend who would fuck me hard — like, he didn’t know any other way. Sometimes it was so hard I wanted to get out of the way. We’d been seeing each other for a couple months when I started to get what felt like abdominal cramps, so I went to see my doctor. They weren’t abdominal cramps — my boyfriend had fucked me so hard he had dislocated my pelvis.
13. Gabrielle, 26
While he was fucking me from behind, he “accidentally” pulled out and shoved his cock into my ass. I started crying and I’m pretty sure he got off to that.
14. Kent, 27
It was a Friday night after an exhausting work week, and neither my girlfriend nor I had the energy for a full-blown fuck fest. We didn’t even have the energy to do oral, so we took turns jacking one another off.
I guess it was my fault for leaving the lights on, but as I came, I squirted out equal amounts of bright-red blood along with my jizz. Talk about ruining the mood!
I went to see a urologist, and he explained that I must have burst a testicular blood vessel during a previous bout of rough sex. Well, at least I didn’t have cancer. But I avoided getting hand jobs for at least a year after that.
15. Cedrick, 36
I once had a girlfriend—a very nice, prim, proper, intelligent, decent, and affluent girlfriend—who would involuntarily shit herself during very intense orgasms. It happened maybe three or four times.
The first time it happened, she had been riding me on top. Right after we finished, she yelled at me to leave the room. Confused, I asked what was wrong, and she told me even more sternly to leave and that she’d tell me when it was safe to come back. I huddled down in the cold bathroom wondering what the fuck was up.
16. Chris, 29
She wanted me to take a shit on her chest. I’ve heard of that before, but you gotta factor in that all shits aren’t exactly gonna be prim, proper and totally dry. I declined, think it was good for everyone. Weirdest second date I’ll ever have I’m pretty sure.
17. Evan, 24
I was talking with a girl I met online. She lived out in Chicago and I lived in Boston. We really clicked, like we were meant to be. We made arrangements to meet each other halfway, but the night before we were supposed to leave, she sent me a text saying, “I can’t wait to fuck you.” Man, I was so turned on! I texted her back and we started sexting until she started sending me photos of her naked. Then it started getting a little weird. She started sending me photos of herself with vegetables in her vagina accompanied by captions like “I want you to fuck me raw!” and there’s like raw carrot in her pussy. The coolest picture I’ve seen ever was of her sending me 5 carrots just hanging out in there. Yeah, we still met up.
18. Paul, 25
She punched me in the fucking head when I told her I was going to cum. Like she straight up punched me on the side of the head. Who the fuck does that?
19. Heather, 28
Back in college, my boyfriend needed to watch porn while we did it. I wasn’t too sexually experienced at the time, assumed it was somewhat normal, but was a bit horrified that he was eventually gonna expect me to do what was going on in the videos. Eventually I told one of my friends about it who was horrified — I had to convince her to not tell anyone, it easily could’ve gotten out of hand and spread through the whole school. I liked the guy but the whole thing got too out of hand — and looking back now, supremely messed up for being so young. So I ended up dumping him, and opted not to say anything to the girl he dated after me.
20. Jaime, 28
My boyfriend had this super-expensive black couch that we’d have sex on because it allowed us better “angles” than his bed. I think it cost at least $2,000. We’d do it so hard, we’d move his couch back and forth across the room several times during one session. One night I was on top and I suddenly felt a “buckling” feeling in my pelvic muscles. I paused momentarily and then—whoosh!—I squirted what felt like a quart of lady juices all over his couch. It ruined one of the cushions. He joked later that he’d never paid more for sex.’
21. Jen, 23
I have this exhibitionist streak when I get drunk and my boyfriend really hates it. Well, long story short, we had a couple of drinks in the apartment and I got really horny. I made him fuck me up on the roof. He couldn’t get himself hard, so I yelled at him for not loving me enough and I stormed into bed.
22. Monica, 27
I lost a tooth playing softball in my teens, so I got it replaced by a dentist. I knew a guy who had a “thing” for women with missing teeth. He had such a “thing,” he couldn’t even get it up unless I removed my fake tooth—at which point he’d get harder than a police baton. Guys are weird.
23. Elia, 25
I was dating this guy that I was really, really, REALLY into, so I didn’t want to do anything that would scare him off. He had a lot of weird sexual desires, but I went along with them (even when they creeped me out) because I was afraid that he would break up with me. (This guy was tall, gorgeous, had a great job, and was incredibly charming. You get the picture.) But one night he asked me if I would roleplay his “mommy” in bed, and I just couldn’t. I tried for like half an hour, telling him he was a “bad little boy” and letting him suck on my boob… but it was just… too much. I had to leave him.
24. Dan, 30
My wife gets off when I call her names in bed. One time, I asked her if she liked getting pounded, and she said, “I fucking love it when you fuck my cock.” She knew she fucked up as soon as she said that. Yeah, that was pretty funny.
25. Nikita, 23
I have this fetish where I get unbelievably wet when someone throws money at my body. I asked a guy I was dating at the time to do it, and all he had was change. Don’t throw change at me, please. Just don’t.
26. Kevin, 33
I had been married for six years and was getting soooooo bored with our sex life that I started having an affair with a girl I knew through a friend.
She had a tight body and was shaved down there just the way I like it—“Hitler mustache” and all—and we had sex three times in her tiny apartment on our first date. As we were laying around sweaty and exhausted, she whispered in my ear, “Oh—I forgot to tell you—I’m HIV-positive.”
Turns out she was lying and that was her idea of a joke. I guess that’s what I get for cheating.
27. Bradley, 28
I used to date a girl who only could get off when I would talk about the other women I was attracted to, talking about what I wanted to do to them and how much hotter they were than her. Honestly, all it ended up doing was making me actually want to cheat on her with those other girls (she was not open to the idea of an open relationship, ironically).
28. Kelsey, 22
My boyfriend always wants the TV on when we have sex and he has to be facing it, no matter what. It’s really, really bizarre.
29. Mike, 26
I was renting an apartment and my girlfriend of the time had moved in with me but wasn’t on the lease. Things got real bad real quick and I finally sent her packing back home to her mom’s. My big mistake was that I didn’t ask for the apartment key back.
One afternoon just after me and a new girl had finished up, I heard a knock on the door. Then, before I could say anything, she opened the door, saw the new girl, chased her naked ass down the apartment hallway, and came back at me with a look of murder in her eyes. She took the mattress on which we used to sleep together, dragged it down two flights of stairs, and put it near the dumpster in back of the building because I’d “tainted” it by having sex with another girl.
30. Jerome, 34
This one girl I was with was very into hot candle wax — me pouring it on various parts of her body. Nothing bad ever happened, but it freaked me out and I really couldn’t handle it.
31. Scott, 24
I knew a girl who always asked me to piss on her. I wouldn’t do it because I thought it was gross. Then after we broke up, she went around town telling everyone I used to piss on her and how disgusting it was.
32. Eva, 26
I once slept with a guy who asked me to rub his body with olive oil and pretend that I was cooking him while we were having sex. Like he asked me what kind of vegetables he’d be prepared with and how well he was going to get “cooked”.
33. Nicole, 23
This guy grabbed my (slight) tummy pooch during sex, squeezed it, and started wiggling it back and forth. Telling me I was a “sexy chubby little girl.” He came all over my stomach, I removed myself from the situation, and never called him again. No, thank you.