Worst Sexual Experience

Contributor: PussyGalore PussyGalore
Everyone has had those days or nights where nothing seems to go right. Would you care to share the details of one of your worst consentual sexual encounters? For those who don't want to share the deets, do you count your bad experinces as experiences at all or just write them off?
10/22/2010
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Contributor: Chilipepper Chilipepper
Mine's more 'sad' than 'worst'.

A mutual friend and I, about two years after graduating high school (this was in 98), find ourselves hanging out as usual. All fine, then we start making out. Neither one of us had expressed any interest in the other up to that point, so it was just sort of a spontaneous surprise.

So, it gets in the point in which his hands are in my clothes and I'm undoing his jeans, and we're like "Okay, may as well go all the way since we're half-way already."

Um ... not quite. I was still so inexperienced that I wasn't sure of what to do with him, and I don't think his heart was in it that much, either. I would not relax enough for penetration (or anything else for that matter), so the experience just sort of ended with him wanking in the bathroom while I berated myself for being so stupid. (About what, I wasn't sure.)

WEIRDEST PART about this???? He's asked me to be his mistress a few months ago and - now that he and the girlfriend broke up - he's been making noises about him and me getting together to try it again.
10/22/2010
Contributor: mrs.mckrakn mrs.mckrakn
i had snuck my by into my room in the middle of the night. about an hr later i saw my dad outside my window looking like he was ganna kill us. good thing we ended up getting married...i really wanted to die in that moment.
10/25/2010
Contributor: socceras socceras
Quote:
Originally posted by PussyGalore
Everyone has had those days or nights where nothing seems to go right. Would you care to share the details of one of your worst consentual sexual encounters? For those who don't want to share the deets, do you count your bad experinces as ... more
i started my period when a guy was fingering me
10/25/2010
Contributor: Blinker Blinker
I puked during doggie style sex.

And we kept going.
10/25/2010
Contributor: Waterfall Waterfall
Quote:
Originally posted by Chilipepper
Mine's more 'sad' than 'worst'.

A mutual friend and I, about two years after graduating high school (this was in 98), find ourselves hanging out as usual. All fine, then we start making out. Neither one of us had expressed ... more
Something similar to this happened to me when I was younger. Things seemed to be leading to sex, so we went ahead and tried and I wasnt relaxed enough, and the foreplay was lacking, so I complained about how it hurt so much that we gave up.Later he confessed to beign a virgin and was weird afterwards lol. These are the memories I love to forget sometimes but they are still funny every once in a while.
10/25/2010
Contributor: Riccio Riccio
Many years ago, I was picked up by a girl after a long day of work and a long night of drinking.

She was on top when I fell sound asleep.
10/26/2010
Contributor: Tori Rebel Tori Rebel
I'd had quite a few drinks and passed out cold while my now ex-husband was going down on me. I'm curious as to how long it took him to notice, only because it was never something I enjoyed him doing so I was always pretty quiet...
10/26/2010
Contributor: GeekWife GeekWife
Fooling around with a guy friend in college, I was going down on him and when he moved I noticed he left a skidmark on my white down comforter. I've never looked at him the same way again.
10/26/2010
Contributor: Chilipepper Chilipepper
Quote:
Originally posted by Tori Rebel
I'd had quite a few drinks and passed out cold while my now ex-husband was going down on me. I'm curious as to how long it took him to notice, only because it was never something I enjoyed him doing so I was always pretty quiet...
Mine didn't even bother doing that. Just ... sexual = not happening.

My whole marriage was the worst sexual experience of my life.
10/26/2010
Contributor: kinky girlfriend kinky girlfriend
Quote:
Originally posted by PussyGalore
Everyone has had those days or nights where nothing seems to go right. Would you care to share the details of one of your worst consentual sexual encounters? For those who don't want to share the deets, do you count your bad experinces as ... more
ya the worst one it was scary but everything turned out fine. At work in the storage room my bf and I were goiong to have a quick one I was extremely bloated I was stressed too but also was in the mood for a quick one so my bf tried entering and blood squirted out and a small puddle on the floor some of his skin tore because I wasn't wet enough.
10/26/2010