Most awkward thing that occured during sex/play time

[SmokingAces]

I got two experiences that stand out in particular.

The honors always go to this girl when it comes to lack of class. After an argument about how I felt that she should go home as two days and nights together was enough she got mad, really mad and went and spoke to my mother. She got straight to the nastiest thing she could think of. Somehow I knew she was gonna show her ass quite literally but she ended up showing my mom her asshole.

She told my mother I put my cock in her ass and dropped her pants and bent over to show my mother the damage. I heard that part and was like "Yo, you told me to put it in your ass." Well my mother being a psychologist has seen it all and says "That's nice dear, how about a ride home." Well this chick was like "Fuck no, I want to stay here and hang out." My mother says "Well no one wants you here and to be honest you just kinda showed up, my son did not invite you, but look he is tired, I am tired, and well you are fucking annoying, so should we do this the easy way or should I get my gun and mace?"

Haha that's hilarious. The bit where you said "I just knew she was gonna show her asshole" that killed me man.

 

[Tchelle]

I was giving oral to my girlfriend when my long time guy friend snuck into the room and started doing me anally
She didn't notice for about two minutes then when she did she really freaked out
Two weeks later she asked us to fuck in front of her
Afterwards she wanted me to do her while he did me

 

[NikeGirl]

One guy was talking to another girl on the phone while I was giving him a blow job.

 

[MikeyTheGreat]

Ah, man..

So, back in 2009-ish. I was dating my high school sweetheart who is now my ex-wife. We were 15, 16 at the time. Young and curious. Had recently lost our virginity's to each other and were always so eager to have sex. We had a routine. Leave school, get to her place, fuck before her parents got home from work. Mind you, we had the WORST sex. This went on for years too. I don't know, her and I was definitely something that lasted longer than it should have. Anyway. So we start off missionary. Cool. We switch to doggy. I'm nailing her.. but this time was different. There was this smell that I couldn't wrap my head around. I've never smelt this before and it was absolutely horrible, I can't believe I maintained a boner throughout this shit. I'm still going, looking around trying to figure out why my nose hairs are on the verge of burning, mind you she has no idea any of this is occurring. Bruh, I look down.. there was a ring of SHIT around her asshole. As if she shitted, finished, and thought "eh, fuck wiping" and went about her day! It was fucking TERRIBLE! I went on for about 30s longer and just stopped. I couldn't handle the shit(literally). To this day she has no clue. And she never will.

 

[Vagina Lover]

There have been plenty of "awkward" moments:

Getting kicked our of a taxi for getting a blowjob
Having a girl vomit all over me when she was deep-throating me
Being walked in on by my girlfriend's father while we were fucking in their lougeroom
Finding out the condom was broken after I had blown my load in her
Being caught by hotel staff having sex in the hotel pool
Looking at the time after having meth-sex for about 3 hours
Being walked in on by my girlfriend's friend while having butt-sex on her bed
Realising we had an audience after having sex with the curtains drawn, complete with them waving at us
Vagina farts are always fun, but proper farts during sex are even funnier
Jizzing in a girls mouth when she wasn't expecting it, but she had told me to relax and let her do her thing as if to say it was ok

That's just off the top of my head. But I'm sure there are heaps more and worse than those

 

[Hurhel]

Riding my man and bouncing on his dick so hard I kinda landed wrong on his dick ! I hear a big POP sound and he yelled ! Yup broke his dick pretty much. Lol
His dick was bruised really badly

He was fucking me while he held my ankles near my ears (missionary) and he jammed my pussy to hard and I heard a POP he broke a hole in my flesh next to my pee hole. Blood everywhere !! I got a towel and used pressure on my lady bits.
I was so scared to have sex again way later month later lol

Queef while getting fingers Jamed up my sopping wet pussy.

Getting pubes stuck in my throat ! Ughhhh I have to eat bread to push it down.
i make him shave his balls and all pubes now. Even his armspiTs

He was shaving my pussy and my lips and my Clit got hard and he nicked a piece of it --i bled some
It's very erotic to have someone shave /trim your crotch. My clit gets so engorged when I'm really horny. I love My clit being sucked with lots of suction from a hot mouth and lips.

 

[Lacquerman Steve]

Back in my early 20's (1990, I was 23..), had a girlfriend (more of a mutual FWB thing) who introduced me to a smoking hot friend & coworker of hers. Couple days later, I'm at the friend's house, (go ahead, judge me..) fingering her under a blanket on the sofa in her living room while her gay brother is singing/wailing "Nothing compares to you" from the loveseat. So we go up to her room. Her pussy tasted fine, actually better than most. Fucking her, she was nice and wet, everything was good. But, when I pulled out of her, suddenly the room filled with a godawful smell. I don't mean she farted, or shat the bed - I mean it smelled like something had crawled up in her and died and I had pulled that out of her. Neither of us said anything, and I managed to not puke... but I never went back...

Not quite an embarrassing event, but the only 100% effective line I've ever found to guarantee sex with a woman, is to tell her "I'm actually not trying to sleep with you - I knew from the moment we met that we wouldn't ever be together like that". It's worked every single time I've tried it.