Most Embarrassing Moment

[GroobySteven]

I congratulated a woman friend on her pregnancy--and she wasn't.

Done that ... twice (not to the same person) - horrible to be told they aren't.

[GroobySteven]

Driving from Ithica to New York needed a crap desperately so pulled over in rest stop, grabbed reading matter and ran into the can. Sat there a good 20 mins enjoying an article and a movement.
Washed up, came out only to find a line of 20+ women waiting for the toilet and the rest stop attendant going in a sneering voice, "Oh here he is, blame him ladies".

[RallyCola]

i was at UPS dropping off a package and my pants fell down and i was wearing tidy whiteys because it was laundry day...it was a wee bit embarassing

[RawNY]

A few years ago I walked up to a woman from behind thinking it was my then girlfriend. I pressed my cock against her ass and reached around and placed my hands on her breasts. Well, you guessed it. It was not her. Just before she could scream, my g/f walked over and they had on almost identical jeans, Uggs and white tee shirts. I was sort of hoping that they might hit it off and we would spend the rest of the night together. But they had a laugh at my expense and we left before she changed her mind and pressed charges.
Oh,they were real and they were spectacular, lol

[Prospero]

I had an embarrasing moment on the sleeper train from Northern scotland to London a few years ago. I'd met a lovely girl while up there and we were having rather energetic sex in our shared sleeper compartment when the train had stopped in Edinburgh and - suddenly - the blind flew up to reveal us to lots of people on the platform.

[rbiller]

Well seeing that this is a Tranny forum I would think this has happened to other guys as well. I have been having a bit of a problem cleaning out lately, even after 4 or 5 enemas. The fact that I have to drive over 2 hours to get to Toronto from Buffalo might add to the problem. Well I guess you can figure out what the problem is w/o my saying it. This happened to me twice with the same girl and no she does not have a big one. She was very understanding and suggested I bring an enema with me the next time which I have done and have had no further problems. I have become pretty good friends with this girl and a couple of months ago she sent me an email telling me that she had just had a session with a good looking hunk and she exploded all over him so I guess if it can happen to a real pro it can happen to anyone.

[Dino Velvet]

Fortunately for me my most embarrassing moments are usually during alcoholic blackouts. I remember nothing but deny everything the next day.

[Wendy Summers]

Not my embarrassing moment, but was spending sometime with friends. One guy asked "so did Jenn ever dump that loser of a boyfriend?". Jenn's boyfriend was in the room at the time. [names changed to protect the clueless]

[GrimFusion]

I was with a chick I'd been trying to get with for awhile and couldn't get it up

Ditto, but I'd just gotten out of a 3 year relationship and the chick had been trying to get with me for a while. The entire three years and the four years before that I'd been with women in LTR's who were sterile and tested, so no need to use a condom. I was good to go until I got that condom on and started going at it. A minute later and I was rocking limp dick. Trying to explain that to ANY female is rough.

That's not my most embarrassing moment, though. I'm horribly afraid of heights, and when I was 17 I was crushing on a chick who talked me into going on the Farris wheel with her. Normally I would have said "hell no", but she wanted to make out and that was motivation enough to deal with it. The first spin was nerve-wracking, but I settled down on the second and third. On the fourth, the operator brought the wheel to a stop. All of the carts started rocking back and forth and I was stuck at the top. I got queezy and ended up puking in front of her and into the empty cart below us. The operator saw, started the wheel up, and kicked me off. I tried explaining my fear of heights to the chick I was with, but she was already grossed out and couldn't understand why I didn't just decline the Farris wheel. Dumb shit teenagers do to get some.

[flabbybody]

asking a friend how their mother was feeling..... forgetting I attended the woman's wake 2 years earlier