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What was your most awkward/terrible sexual experience?

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Pcp3t3

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What was your most awkward/terrible sexual experience?

Mine involved someone with a smelly/unclean ass wanting me to fuck him. He either didn't realize he was unclean, or didn't care. It was awful, and made me not want to have sex for a while.

What was yours?
 
Worst one for me was similar to yours Pcp3t3. A guy wanted me to fuck him but wanted me to finger him first. I wasn't really into it but decided at least I'd finger the guy. (Warning....the next bit is exceedingly gross). I started fingering him and OMG, shit started coming out of his ass. I almost vomited on the spot. Ran and scrubbed my hands. He apologized but I was so sickened by it I had to leave immediately. Never saw him again, thankfully.
 
Well, if we're assuming the sex was consensual, the most awkward would be me trying to be on top with a previous partner. My back locked and I had to fall to the side in a controlled manner. On the other hand, when she went to fuck me her knees gave way because she has knee problems and....yeah. It was like a flash forward to my future geriatric-hood, only I was 30 at the time. Our various disabilities kinda made it awkward. On the other hand, she was really good at fisting, so.
 
Mine involved rimming.
I went to part his sexy hairy ass cheeks,and got a whiff odor of full fecal smell.
He wanted me to tongue his ass, but I was ready to gag, so I went back to sucking his cock, and tried to get him off as soon as I could to end it all without embarrassing him.

Back in my slut puppy days, my tongue wouldn't touch a rosebud until my finger has been there first and came out clean smelling. If I got "stink finger" it was a deal breaker. This was one of those times that I didn't check first.....
 
Pretty much all of them... which is why I don't do sex with anyone other than myself... at least for now. Who knows, that my change.
 
This guy and I were in a 69 position, going down on each other, but he had a difficult time keeping his legs still. He would get so into it that he would wraps his legs around my neck and head, making it hard for me to breathe. When I finally tried to move his legs, he all of a sudden jerked his knees and slammed his knee into my face, giving me a bloody lip. Well that was that... At least he offered to just service me while my mouth was out of commission for the time being.
 
Here I thought I had a rough life..... But reading all y'alls terrible experiences makes the first 11ish years of my life as pedophiles' slave seem like nothing. I never realized just how lucky I am. :rolleyes:
 
in high school my buddy & I were in the back seat of my small car on a gravel road... I was on my back and he went down to rim my ass, and right at the same time I moved my knee and cracked him right in the nose. blood starting pouring out. I felt so bad. That killed the moment and we drove back into town.

One other time, a different guy accidently farted when I was rimming him. He was mortified. Kept apologizing. I didn't care tho.
 
First guy, second round. We were in a hotel room now, and we'd had manual/oral sex once earlier. But he apparently hadn't learned a thing from the previous encounter. There's only so many times you can say "not so hard" and "watch the teeth" before you realize that this guy's learning curve is a horizontal line.

Lex
 
Well i have a no rimming policy but once I was fooling around with a guy. It was pitch black in his room and he was playing opera music which creeoed me out. It was really Hannibal lectory. We were 69ing with him on top of me. He stuck his balls in my face and told me to lick. So I did, thinking I was licking that space between his nuts and his anus. All of a sudden I felt something move and my mouth was filled with fart smelling gas. It was so gross.

I also vomited on a guys willy because he was one of those guys who holds your head down really tight and humps your face.

Most recently, a guy grabbed my brand new air Max 90s and blew in them. I just sat there staring as he was moaning loudly and rubbing his willy on the sole of my $200 shoe that I saved up forever for. He also asked to eat off my feet which creeped me out because I have an anti-foot fetish
 
Some of these are disgusting :(. I've only ever been with one guy and he was the top, so nothing awkward came from/out of me :p. When I tried the topping role, yeah there was shit :(. I don't understand why a guy at each shower wouldn't clean that general area. I didn't even fleet before I got fucked 'cause just cleaning that general area (around the hair where shit could get stuck, and just inside the hole etc.) was pretty much enough. He never pulled out of me to find shit on the condom. Never :p. Maybe the tiniest brown tinge a couple 'times, but when I did it it was actual shit, not just a miniscule little stain on the condom :p.

I'd even be willing to wait before sex so the other guy could have a shower if I knew his anal area would be at least clean.

The suckful part of gay sex I guess. With a chick it wouldn't even matter if she'd washed right before sex, not if you were using a condom anyway...
 
Having my cherry popped by a young guy, who was just as inexperienced as myself. Talk about yelping.......:dead:
 
dpnice said:
Cramp! That gets me every time.
Click to expand...

ogod, those are a bastard. Unfortunately they're usually in my thigh and generally just with oral. There you are, enjoying yourself, and you find your leg cramping up and you're willing it to go away and it most definitely doesn't. I've decided no more oral on the chair, hoping the position is the problem.
 
One day I saw this ultra hunks at swimming pool in a countryhouse. He kept flirting at me and he gave me a code to 'having a little fun'. So we sneak to the shower for a while (that was a quiet day, noone around, and not much people on the pool). He was so hot and huge and we had our fun. Well after we finished we back to the pool acted like nothing happened. I met my friends and he swam alone, until when I decided to shower after swim and so did he, and then the most awkward thing happened, two little kids came to the shower room with him and calling him daddy. So he's a daddy who waited to his sons' swimming lesson. That was pretty awkward Lol.

The other one, I met this guy, we had sex and nothing weird happened until when we were back dressing up after sex. I realized after I went out from his room that I was wearing his undies instead mine. We're wearing the same brand and color only different in size LOL. So I knocked his room again and asked my undies back LOL
 
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