My girlfriend was deepthroating me, and right at the moment I climaxed she lost her lunch. It was pretty gross, and more embarrassing for her. But we laughed it off, and I gave her kudos for the effort despite the discomfort!

When Father Maloney said my penis was smaller than the other altar boys

I dropped her during the standing portion of the act. In my defense she was pretty sweaty and I worked arms at the gym earlier.

Never had sex

More funny than embarrassing - years ago, while we were totally disracted by one another, my then dog - a boxer/shepherd, chewed the crotch out of his underwear - shredded !

My Mom walked in on us. " Hi Mom, your home early. "

I had sex with my girlfriend while her mom (a JW) was holding a Bible study in the room right below us. We got got yelled at because the lamp, furniture, etc. was shaking in the living room while they were attempting to prayerfully and solemnly study their New World Translations...

With my first ex wife, her on top, got sharp pains so kinda... pushed her to the floor. Went to the army ER in my boxers with my first kidney stone.

Not being prepared for that time of the month. It was my freshman year intersession. I was in Coimbra,Portugal at the University partying with this gorgeous guy we had met in the park that afternoon. I got locked out of my pension and spent the night at his apartment. Had a fun crazy night despite.

She looked me in the eye and said.... "Wrong hole."

Not sure that it was actually embarrassing to me, but I fell asleep during sex once.

So apparently I hit a nerve while we were going at it and she ended up peeing on me.

A guy came into the stairwell and I ran down the stairs. That was embarrassing as hell.

Shy to say it on the internet lol

The one thing that would embarrass any man: Whiskey dick.

Two things: Junior high school, I took a girl up behind the DJ booth and we got caught when the DJ turned to do something, tripped over the horny teenagers that were us, fell down the stairs and broke a finger. Second one was my ex giving me a mouth party and when we got busted by cops.

Hmm... I think it involved a really smally fart which really killed th mood.

Got busted by my first wife's catholic grandmother before we were married.
Woke up to realise I'd spent an energetic night in a bay window facing the main street.
Had the young fella, then three, walk in and ask "Where's mummy?". (His mother is a foot shorter than me.)

My then girlfriend gagged and threw up on my cock while giving me head.

Her dude kept staring at my junk watching get dressed, he busted us.The staged heading off to work hun trick . Lol

Hurting my back

Nothing.

I was having sex with my then girlfriend and I called her by my mates mum's name. I got slapped several times for that stunt!! What about yourself

I actually just thought of another one! One time a woman slapped me on the ass while we were having sex and I was not expecting it at all, nor had I ever had that happen before, and I started laughing hysterically. Needless to say, the sex ended and she stopped talking to me... but I couldn't stop laughing. I have no problem with some love taps here and there, but it was such a new and unexpected thing for me that I couldn't help myself. I was embarrassed both by what happened and by how I handled it.

To me the most embarassing moment about my first one-night stand is that he knew nothing about sex. I would say he knows nothing of how to slowing enjoy sex with me.