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What was your most awkward/terrible sexual experience?

The most awkward sexual encounter was, lets just say when I was young, I was fucking a friend in a bathroom and the school nurse caught us.
We stopped, she left and nothing was ever said by her to anyone. I avoided her after that.
 
Eh, I think people have to have a sense of humor about sex, otherwise a tiny awkward situation, like say, a flaccid penis ;) can turn into an emotionally charged situation. No one wants to be naked and embarrassed. Well, unless that's their fetish.
 
well just wanted to say--this is not about me--but all the gross guy on guy action made me think when I was in college--I worked as a waiter for a total scumbag who owned a popular city restaurant--he was a loud mouth conservative a fake "moral" guy-- and married with 3 kids and lived in New Jersey. Every middle aged lonely ugly woman who ate at the restaurant he would eventually go home with and fuck after a bunch of free drinks. The poor desperate things---when one gross overweight one went home with him---they both left drunk-- so, while he was on his back fucking her-- while she squatted over him she shit all over him lol---justice was served---he didn't share this to me but his buddy told me as he thought it was so gross/funny. Could not have happened to a bigger asshole. I tell this story as shit happens even for straight people.:p
 
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.

That sounds hot! !oops! Daddy's gotta have their fun too. Was he kinda older (like 40+) or a young daddy? It's not as if the kids were watching.
 
That sounds hot! !oops! Daddy's gotta have their fun too. Was he kinda older (like 40+) or a young daddy? It's not as if the kids were watching.

He's approximately in his mid 30s. Well I met him again after 3 years, I just joined a new gym two months ago and he's the member there as well. I guess he still remembered me because I caught him several times checked on me and gave me smile LOL. I quit from the gym last week because I got to move somewhere else closer to my home tho LOL.
 
Mine isn't nearly as bad as most of these. :D

With the then-bf, during a switch in position I managed to fall out of his bed and put my elbow through the glass pane on the door of a display case which was functioning as a bookcase and CD rack.

No blood or damage to me, miraculously, but the glass breaking and the thump of me hitting the wooden floor and then his roommate asking from next door "is everything alright in there?"

-d-
 
This guy i met on Grindr he was an overweight guy mind you i am overweight too. He came over and took all his clothes off and flopped on the bed like a log in water. So I'm trying to kiss him get the scene started and he just stares in space and asked if i could suck his dick. I said ok, He had a really tiny dick and he kept trying to choke me with it. i would suck him off and then out of no where he try's to throat fuck me it was so annoying so he would threaten me and i had to beg him not to face fuck me and he turned him on. He had an odd request he asked if i could chew his dick i said ok and then he wanted me to act like his dick was a piece of steak or something. I had to compliment how delicious and hungry i was for his meat.

I quickly sucked him off and shoe him a way quickly as possible. The next day he tried to message me and meet again i told him about him self and his shitty attitude and blocked him.
 
He's approximately in his mid 30s. Well I met him again after 3 years, I just joined a new gym two months ago and he's the member there as well. I guess he still remembered me because I caught him several times checked on me and gave me smile LOL. I quit from the gym last week because I got to move somewhere else closer to my home tho LOL.

I'd have been getting that D again if I was you. If he was as hot and huge as like you said.

What the hell's wrong with you? :p

LOL, some of us have trouble getting anyone. Seems a shame to waste hot prime man :lol:.
 
yes, he's totally hot and mighty fine. Very hunky with toned pecs and abs, but IDK for me it was an awkward encounter and I think I'm kinda shy lol
 
yes, he's totally hot and mighty fine. Very hunky with toned pecs and abs, but IDK for me it was an awkward encounter and I think I'm kinda shy lol

But he clearly was into you too and you had the green light by your description :p. I'd only understand being shy in this case if you weren't sure of that...but oh well, your call ;).
 
What is it they say?

"Never look a gift horse in the mouth."
 
My worst one would have [STRIKE]probably[/STRIKE] definitely been a "best one" for a lot of guys....the guys who obsess over other people's appearance.

The guy was a jock and I [STRIKE]probably[/STRIKE] definitely had a bit too much to drink...one of those classic "handsome" guys in most people's subjective opinion....and when he was fucking me when I was laying on my back he started saying things like I was the lucky one who got his attention...tell him how hot he was...he wanted me to tell him how lucky I was...tell him how he was the best looking man I had ever seen....talked about "making love" (BARF)....on and on and on.....

I eventually pushed him off of me and took a shower and scrubbed hard to get him off of me....he reminded me of a lizard
 
A sleazy looking guy tried to fuck me with his balls, it was hilarious and gross at the same time.
 
i actually have two different occasions.

the first occasion was a guy i went on a date with insisted on sex on the first date. we went to an empty cal-de-sac, and proceeded to try to get something done. it was so awkward that it didnt happen. then we went to mcdonalds for dinner, where he told me he was a drag queen, which is fine, that didnt really bother me. before the end of the date he told me he loved me and wanted me to move in with him. i politely dropped him off and never talked to him again after that.

the second occasion was a hookup with an older guy. it was my first and last "daddy" experience. i went over there and he demanded i get on my knees and suck him off. i started to get a little rough because he was trying to choke me, and pulled my hair to make me continue. then, he asked me if i liked toys, and when i answered yes, he pulled out a couple, and made me stay on my knees and put a Dildo in my mouth while he sat there and watched. then he pulled out a huge Dildo and told me i was going to take it and i looked at him and said that was it. i was done there and blocked him. i got dressed, and he wanted to talk actual business while i was getting ready to go. i really wanted to get out of there as fast as possible
 
OhMyFuck some of these stories are hilarious! I'd add one but I'm trying to finish dinner.
 
Oh God summer 2010, after I met my husband, but before we were together. I was still just this stalker he mercy fucked once.

I was following hubby around in a bar and went to guy him a drink. In front of me he grabs this huge blonde guy (you'd have to know how generally messed up my head was at that time about my body, race, gay men, and the general cloud of unlucky that I believed floated over my head to get how this cute little blonde boy I was in love with grabbing this fucking massive Aryan God right before my eyes felt) and proceeds to make out with him while I'm standing their like an idiot holding his drink.

I did have a bit of self-respect--once it was clear that the blondes were not to be separated I decided to leave. On the way out the door I got grabbed by some drunk straight girl whose gay friend (blonde #3) was turning 21 that night. And somehow she ended up encouraging a series of awkward kisses between me and her friend (not sweet awkward, but awkward, awkward).

Skipping all kinds of detail, Blonde#3 and I did actually end up going to his place together--despite my pining over the man who is now my husband and Blonde #3's avowed disinterest in " most black guys" (which was repeated by him THREE times) we had sloppy drunk sex that was pretty good actually.

But after everything was said and done Blonde #3's roommate (Blonde #4) came into the room CRYING about how he was in love with Blonde #3 and Blonde #3 knew that Blonde #4 was in love with him. Blonde #4 threw this stupid stuffed bear at me and told me I had a little dick. Blonde #3 during all of this kept telling his sad friend: I'M NOT OBLIGATED TO NOT HURT YOU!!!!!!!!

This story is legend and was repeated by others to the man who is now my husband. And him deciding to talk to me to get more details of this insane story is what led to my brainwashing him into loving me.
 
Well... once i kinda accidentally farted after the guy pulled out... Nothing came out and there wasn't anything gross or anything... but.... well it was kinda embarassing. The guy laughed for quite awhile... needless to say, we didn't finish the session.
 
Occasional farting during anal sex is an occupational hazard. I really wouldn't worry about it; either ignore it or laugh about it.
 
Occasional farting during anal sex is an occupational hazard. I really wouldn't worry about it; either ignore it or laugh about it.

It's a romance killer, whether I do it or my partner, I usually stop right then and there.
 
Occasional farting during anal sex is an occupational hazard. I really wouldn't worry about it; either ignore it or laugh about it.

Yea, i did kinda farted a few times before with other guys and they mostly ignored it, so it wasn't too bad. But with this guy it was super embarassing cause he was laughing at it... so i just felt like digging a hole and die in it. !oops!
 
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