19 yrs. old, big bad US Marine on weekend liberty, horny as hell. Went to a strip club and met a hooker,who took me to a sleazy,pay by the hour hotel. All the while thinking "I'm going to pound this pussy raw". I came hard while she was putting the rubber on me!!!

 

Got a bit of cum in my eye. Stung like hell.

 

Oh I've got many but the one that haunts me still.... When I was 18 I was with a very attractive and popular 31 year old lady who worked behind the local bar, we were having lots of good mind blowing sex on a daily basis i thought i was the man i became popular down the pub for being with her, then 4 months later, one night we had lots to drink and she told me her friend who she worked with was coming over for a few drinks and she wanted to have a threesome with us & i said fk no i was crushed when she asked me & was very rude to her friend when she arrived & as she left, the lady broke up with me and went lesbian with her friend the one I was rude to,, next time I went to the pub every one was telling me good one mate now you've fkd it for everyone you turned her lesbian,, then few weeks later everyone found out we stopped seeing each other coz i wouldn't have a threesome with them wow was i the popular one

 

Was drunk and positioned above a groupie (her face-down), lost my balance and dry drop-dicked her asshole. Blood happened. I brought her a moonshine bottle out the cooler to soothe her, and the next day my drummer drank from that very bottle.

 

I was a 4th year grad student and during a break my girlfriend and I was having sex in my bedroom at home. My parents were both out so the bedroom door was open. She was riding like hell on top and had a huge loud orgasm where after I came as well - all over her butt cheeks. As I looked up past my girlfriend, there stood my moms best friend in the door who was watching us for probably a long time. As we scrambled for clothing she just smiled and left, but she gave me a constant reminder after that with the same smile whenever she visited my mom.

 

I was fucking this girl i met at a bar, was fucking her in the ass no condom (I know) bare back we were getting into it she came i came I pulled out and had shit on my cock!! man i got mad she said sorry she had to shit I told thanks ahh then let her shit in my bathroom, then we showered togather got cleaned up had a giggle about it then i fuck her sweet pussy!!

 

OMG! Did you and your mom ever talk about it?

 

I was with an older woman, when I just just turned 18. As we were fucking she said
"cum with me"
To which I replied
"where?"
Not so much embarrassing as funny I guess.

 

any new?

 

I was fingering the new girl in the office while pretending to help her with the shipping screen on her computer. Did not hear my father come in, he walked up and tapped me on the shoulder asking if I was ready to head to lunch...finger was buried to the knuckle in the new girls twat at the time.

 

When my mother walked into my bedroom when I was balls deep in my sisters cunt

 

I had a guy lose a condom inside me.
It just came off. He wasn't a small guy but somehow it worked it's way off and he continued fucking me.
I noticed something rubbing inside me and I was getting sore. After a while, he started feeling sore also.
Once he noticed it was gone, he stopped but it had pushed way up there. I tried pushing it out while he dug in with his fingers but he couldn't get it out.
I guess I panicked but it would have eventually worked itself out but, I didn't have patience. He ended up using 2 spoons to fish it out.

Oh, this was our second date and the first time we had sex.

 

Did you marry him?

 

This thread started off hot and then just became downright awful.

 

Hmmmm . . . which story to pick? I'll list a few . . .

• My old Italian grandmother walked in on me masturbating, and really quickly, I said, "Nona, my hands were just so cold! I had to warm them up!" She was so sweet, she brought me a knit blanket.
• Late one night, I was fucking my boyfriend in the front seat of my Datsun 210, but I'm really tall, and when I started cumming, my knees kept hitting the horn and it was soooo loud! You could see lights coming on inside all the houses and people peering out. Totally ruined the orgasm.
• I was having sex in the shower with my boyfriend, and I grabbed on to the shower curtain because I started to fall, and we both came tumbling out onto the floor, screaming. His mother left work early that day, and she was standing right outside the door, asking what the hell was going on. The worst thing is, she called my mother and told her what happened. I wanted to die. I remember my mother getting the phone call and slowly looking over at me with this sour look on her face. UGH.

 

My wife has had a few embarrassing things happen during sex, most of them in college. Like someone else, she farted while I was licking her pussy. She had a large wet spot on the back of her denim dress from where my cum had leaked out of her pussy while we were sitting somewhere and looked through her panties, and left a large wet spot on the back of her faded denim dress (making a much darker spot). Once when we were visiting her family over a spring break, she and I were having sex when she heard the garage door open indicating her father was home. We both jumped up and got dressed quickly and after talking to him a few moments, we left to go run an errand. While on the road, she found that her shirt was buttoned up wrong and partly untucked, so her father had to know that she put her shirt back on in a hurry. I don't know if he noticed or not, but I had forgotten to zip my pants, but while we were out, after she fixed her shirt while I was driving, we swapped places and I undid my pants and removed my condom while she drove. Regretfully with the interruption, neither of us had cum.

For me, the above incident with her father, or many years later, after we were married, we were visiting my family. My wife was in bed nude, and I was sitting on the side of the bed caressing her tit while she was stroking my cock. Much to our surprise, the door pushed open and my mom stuck in her head because she thought we might have fallen asleep and left the lights on since it was 1:00am her time (but it was only 11:00pm in our home timezone). I don't know if she saw anything, but she never let on if she did.

 

Had sex for an hour plus without cummin

 

I've had a number of embarassing ones.
Was fucking girl when younger at friends house, when looked round and friend and her sister were stood watching in doorway.. I was doing it from behind and at point of no return... jerked when saw them watching and cock came out of pussy.. squirted full load into condom facing them !!

 

Was with ex-girlfriend fucking in swimming pool changing cubicle... she made bit too much noise and next cubicles both put heads over top !!!

 

I was being bent over a couch and the guy was doing me from behind when I started spotting a little. He slowed down and then I heard "Thump" and I looked back and he was on the floor. He passed out at eh sight of blood. It wasn't so much as an embarrassment for me, as it was for him.