[Question] (So very NSFW) What's the worst sex you've ever had?

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I once had to fake an orgasm -and I am a guy, so this seems particularly anomalous- because the girl I was with would do little other than lay there. During foreplay she gave the worst blowjob I've ever had (yay teeth?) and refused to tell me what she enjoyed even when directly asked.

She described the sex as "amazing." Don't know if she was just trying to bolster my ego and it was actually me who was bad for her, or what.
 
Gay virgins are terrible... just terrible. Never again. For many of them coming out a little later, it's like they can't decide what it is they want to do, but don't feel comfortable about it yet, so it ends up being a clusterfuck.
 

Dave

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I was 14. Back of a car. My first time. I thought it was great. She was drunk and probably unsatisfied. Did I say probably? I mean definitely. So I'm probably what she'd say was her worst.
 
She had a weak stomach. I create an over abundance of saliva. A kiss got a little too sloppy and I was nearly puked on.
 

Cajungal

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Hmmmmmmmmmmmm...

He was taking a really long time, and I hurt my leg so bad that I limped for 2.5 weeks. It was right up where your ass meets your hip--a place that's really difficult to stretch in public without looking silly. I got hurt right before a Gifted Ed conference, so I limped around a huge hotel for 3 days.
 
Virgin sex (both of us) with my first (non-elementary, junior high holding hands and kissing a little) girlfriend. Neither of us knew what we were doing and as gentle as I tried to be she was, well, a bleeder.

Bleeder is too tame a word for it, it was a fucking massacre. I might as well have taken an axe to her.

Muslim heaven with all those virgins holds ZERO fucking interest for me.
 
My friend had the opposite problem once. He called her "coin slot." Apparently she was so tight down there it hurt him, and he just had to stop after a few minutes. And he's not the type to exaggerate his own size; he swears it was her being abnormally small.
 
Virgin sex (both of us) with my first (non-elementary, junior high holding hands and kissing a little) girlfriend. Neither of us knew what we were doing and as gentle as I tried to be she was, well, a bleeder.

Bleeder is too tame a word for it, it was a fucking massacre. I might as well have taken an axe to her.

Muslim heaven with all those virgins holds ZERO fucking interest for me.
I've been with 5 virgins. Every time, disaster in one form or another. I have no idea why I was such a virgin magnet but uuuuugh.
My friend had the opposite problem once. He called her "coin slot." Apparently she was so tight down there it hurt him, and he just had to stop after a few minutes. And he's not the type to exaggerate his own size; he swears it was her being abnormally small.
Lube is amazing. I find it hilarious when people take offense like -I don't need lube, I can get a girl wet enough on my own!- :rolleyes:
 
Gilgamesh said:
Lube is amazing. I find it hilarious when people take offense like -I don't need lube, I can get a girl wet enough on my own!- :rolleyes:
He was using lube. Didn't help.
 
I got a few.

An ex-girlfriend and I were driving back to her place after an event downtown. We were dressed up and looking forward to go home to her place, after teasing each other sensually all night. Once in the car one thing led to another and I asked her if she would give me a little road head.

She agreed and began to do her thing as I drove home and she was more enthusiastic than usual and it felt amazing. So I'm trying to drive as careful as possible when boom goes the dynamite. Awesome, right? Wrong.

Apparently we were at a bad angle and when I went off I caused her to instantly gag and she ended up vomiting all over my crotch and drivers seat while I'm still reveling in post blowjob endorphins when all of a sudden I get a whiff of vomit and semen and almost gag myself.

As soon as I realize what has happened I pulled off the road into a parking lot so I can at least attempt to clean up some of the mess and as soon a I park I realize there's a cop on the other side of the parking lot just lurking. He see's me do a high speed turn into the lot late at night so, naturally wants to see what I'm up to.

By the time I get out of the car he's getting out of his as well and he walks up with one hand on his gun belt and the other on his flashlight that's on me and asks "is everything all right?"

Here I am, pants unzipped, crotch area covered in cum and puke and all I can manage to say is, "My girlfriend got sick."

He walks over to her side and she's hanging out of the open door busting up laughing.

He walks back over to me, puts his hand on my shoulder and starts laughing. "Have a good night sir", before walking back to his car and driving away.

And this is how Officer_Charon and I met.
 
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