• Wed, Nov 16 2011

Real Talk: What’s The Worst Sex You’ve Ever Had?

First of all, look at this fucking stock photo!

Anyway. Earlier in the week, EIC Jennifer Wright asked random ladies and gentlemen about the best sex they’d ever had. Today, we’re doing the opposite by asking people about the worst. Screamers, blood and very small penises ahead.

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  • August S.

    Mid-coitus he accidentally slapped himself on the balls, causing him to emit an ear-piercing scream, buck like an electrocuted bronco (catapulting me entirely off the bed) and curl up in a fetal position. When he’d recovered enough to continue (and I’d stopped laughing), we tried again and I promptly got my period… all over his white comforter and manly appendage. In conclusion, we we both mortified, the bedding was ruined and his dick looked like it was the star of a low-budget slasher film.

    Terrible sex*, great story.

    *brought to you by Tequila. Tequila: because you can afford bail, right?

    • Ashley Cardiff

      If a guy slapped himself in the balls mid-coitus I would laugh myself off the bed.

    • August S.

      I didn’t have a chance- his convulsions had already sent me flying! And at first I thought he’d a seizure, or we’d broken something, so there was a brief interlude of concern before the truth came out.

      I did spend a good bit of time on the ground laughing though.

      (btw: This is by far the most hilariously glorious incident of my sexual career. Thank you for giving me the chance to share.)

    • Cassie

      HAHAHAHA great story.

    • Anonymous

      I read your story to my wife. It took me three attempts because I was laughing so hard.

    • Rebekah Mae

      Oh my god, I’m still crying from laughing and it’s been a good three minutes since I read this post

  • failedwings

    So, I met this guy and we would hang out at mutual friends parties and get tipsy and then have sex, which apparently only was fun when we were drunk because the few times we attempted to have sex sober was horrible. Maybe I just didn’t care when we were drunk, or he wasn’t doing the same moves, but when we were sober he was fingering me and totally being rough and not trying to be careful with his nails at all. At which point I asked him to change his technique a bit (in a nice way) because it was literally uncomfortable and he told me “I don’t know why you are so sensitive.” This after not even making the changes I requested, so how are you not able to take suggestions?! I’m like “I’m not sensitive you just don’t know what the hell you are doing.” Omg. Terrible.

    Apparently he idolizes the past situation and thinks that something might have happened from it relationship wise.(Which is just plain ridiculousness) And also he told me that I wasn’t open to doing new things in bed, which is just absurd, because why would I want to try anything new with you when you don’t have any standard moves down and refuse to make changes with what you are doing even when I’m telling that something is painful. Good. Lord.

    • MR

      Yeah as a guy, I know I need to keep the area moist at all times. I always find it makes the sexual encounter so much better when I make her orgasm too. Good foreplay, especially from my side, is always the key.

  • Colleen

    I slept with the weatherman when I worked for a TV station. He asked me if I wanted him to talk dirty. I said sure (in the right cirumstances it can work).

    He hold me to expect heavy precipitation in my Southern hemisphere.

    His forcast was wrong.

    True story.

    • MM

      Good lord. I nearly spat out my tea reading that one.

  • James

    My own story is pretty tame: kissed my way down a girl’s belly, got a whiff of what smelled like 3-day old squid, and came up with some lame excuse for kissing my way back up again.

    My ex-roommate’s story (pretty well verified) is better: he was on top of a girl, drunk, and suddenly puked, right in her face. They did not continue.

    • Anonymous

      Best comment ever!!!

  • Anonymous

    This is actually not my story(!), but true nevertheless. Check this out.

    This dude, wearing a white Adidas jump suit (and matching Adidas sneakers), had a green BMW convertible with white leather seats.
    He checked out this Turkish girl who thought he’s hot; so they drove up to a secluded area on a hill.
    Problem was, the girl couldn’t have premarital sex (Had something to do with her parents stoning her or something like that). However, she thought outside the box and allowed him to perform Anal sex.
    They had a good time… until she defecated all over him (Can somebody say Diarrhea!!). He kicked her out of the car (literally), and drove off.

    He later tried to clean the interior of his p*ssy wagon, but rumor had it that it never was the same.

    True story.

  • MM

    Two works: coke dick. (Said cokehead also ended up breaking my heart, so I derive great pleasure in the fact that there was no great pleasure in fucking him.)

  • Couloropheliac

    It’s too bad you used clowns as the graphic for this post… I’ve slept with a few clowns and they’ve all been great in bed!

  • Anon

    Ha ha, I think accidental ball slapping is more common than people realize – I was on top of a guy once, and he was slapping my ass, and we were getting really into it until…he missed, and slapped himself in the balls, HARD. And then I could not for the life of me stop laughing, as he writhed around in pain on the bed.

  • M

    I’ve never had what I consider to be genuinely bad sex; I’ve had some moderately uncomfortable sex, but it was always still pleasurable. Though one time I thought my sex legs had worn off and I was not correct and managed to fall down the stairs. At my ex’s office. Oops. Fortunately it was the middle of the night [the night before Christmas Eve, no less], so at least I did not fall down the stairs onto a floor full of his employees.

    My favorite disaster stories told to me by friends: a couple I used to know were having a threesome with a girl and managed to break her hip. They were at a party and everyone was hopelessly drunk, so the whole herd of them took her to the hospital because they figured there was strength in numbers. When the doctor asked what happened, someone started with ‘She fell off the..’ and then trailed off, so every other drunk friend chimed in with their own version of what they thought was a plausible excuse ['Couch!' 'Bed!' 'Porch!' 'Roof!' 'Car!' 'Table!']. Apparently the doctor’s expression was priceless.

    Another friend of mine fell out of a plane mid-coitus. I think that’s a pretty good one too.

  • Bad intentions

    I have never considered my self a sexual god or even consistently good at it but, it seems most of the females who I sleep with tend to either be screamers or put their face in a pillow and moan. I feel it is strictly theatrical I would rather have a female hunker and tell me what to do then give me a load of bull. Won’t hurt my feelings. I know every lady likes it a little different. Constructive criticism is better then being bad at something you enjoy.

    The worst sexual experience I had was when I took a shuttle home from a bar I used to work at. One of the females that seemed to be smitten by me helped me into the church where I lived at the time. Which I needed because I was overly intoxicated. I didn’t make it to my room and she didn’t leave. I woke up in the morning with my pants around my ankles in a public location. I don’t know if anyone saw me or if I made it without getting caught. From that point on no more tequila nights..

  • Cherie Samba

    I didn’t feel anything. I had no idea that his penis was smaller than my thumb. And he really thought he was doing something…at least to himself he was, he was sweating, overheating, and he had a major orgasm…and I just didn’t feel anything. I mean I didn’t even feel his penis inside of me and I’m not sure it reached that far. I was just devastated.

    • S.Conrad

      Too bad you didn’t try again (both Cherie Samba and Caroline). This happened to me the first two times (felt the penis was like a pencil in size) I had sex with my then boyfriend and now husband. I was also devastated and almost didn’t want to continue the relationship as I am sure you understand. But I think it was just nerves because afterward he was quite large and I’ve never had better orgasms in my entire life! He is now by far the best lover I’ve ever had and I am glad I gave it 3 chances. Anxiety does weird things sometimes to men!