What was your most awkward/terrible sexual experience?

[Latimer]

Not really that embarrassing, but my new boyfriend (now partner), former partner and I were in a 3-way (I was being spit-roasted) at a hotel room in Florence when the chamber maid walked in, screamed and slammed the door behind her. We laughed it off and continued.

On a couple of occasions I've hooked up with guys--both times in Rome--one with a Roman, the other with an Aussie--and our respective gaydars were malfunctioning so it took hours to establish that we really didn't want to drive around the city looking at illuminated monuments at night or check out the collection in the Palazzo Nuovo but to fuck. Getting to the fucking part was embarrassing, the fucking wasn't.

 

[umjreon88]

Cramp! That gets me every time.

Me too. After awhile of fucking, my leg cramps and it's not the best as sometimes it led to the act not getting finished. Had leg cramps since I was a kid but the pain never fails to get to me.

You guys really took the cake eh? My experience can never compare to y'all.

 

[Ninja108]

Never going to tell.

 

[Kulindahr]

When I was 14, and got awakened by a dick ramming up my ass.

 

[Harke the Boeotarch]

I was forced to do naked drag in my pre-teens by the neighbourhood pervert (with a wig on and my peeny hidden between my legs).
I had to jump out of my sister's closet and say: "Wouldn't you be ashamed of such a beautiful dame?" (In Dutch) in front of my sister who was hardly even out of kindergarten at this point (and the same age as the pervert).

He never got to play with us again. Much later (+-20 years?) my uncle told us he'd disgraced his parents by becoming a rentboy...

 

[Kyanimal]

Have you ever run across a guy that totally set off your back molars watering, butt, yet, when you finally managed to get him naked, and in a compromising situation, you were still so fascinated/intimidated by his looks/build/whatever, that you were unable to "perform"?

 

[chrisdobro]

I can think of some, but most of my threads of hookups are terrible experiences

btw I know people who would love to be in your OP situation, imagine that..

reading most of these, I see people who are trying to get laid and are trying to play out their fantasies, and it's sad how in most cases the lack of prior and ongoing communication, lack of common interests or lack of attraction, or getting scared, or not being ready for an experience turns a hookup into a disaster.

 

[DCRacer]

recently? a three way where the one guy was totally into the acting of being fucked, without a condom (eh, no - ew) and then not coming (saying he only did that with his wife) "get the fuck out of my house"

 

[bw92116]

A middle-aged man picked me up in a bar when I was 21, we went to his place, and while we were in bed his wife came home. I had no idea. She was furious and kept holding up a paperback book in front of me, some self-help book that was popular at that time. I couldn't stop laughing, out of nervousness and embarrassment.

 

[dpnice]

A middle-aged man picked me up in a bar when I was 21, we went to his place, and while we were in bed his wife came home. I had no idea. She was furious and kept holding up a paperback book in front of me, some self-help book that was popular at that time. I couldn't stop laughing, out of nervousness and embarrassment.

The same thing happened to me once but I just hid under the bedclothes pretending to be an ostrich.

She came into the bedroom to find her handbag, nothing was said and I didn't presume to interrogate the guy either. I presume it was some arrangement they had and as he was super in bed I was quite willing to continue seeing him. Oh the follies of youth.

 

[MTLDude]

I once been with a guy, cute as hell, but who turned far too much aggressive... I was sucking him he was forcing his dick in my mouth in a way that was preventing me to breath... I had to grab and twist his ball sack for him to stop... the closest I ever been to rape... He was enjoying the discomfort he was causing me, but was surprised when I cause discomfort to him... And considering the fact that I was twice his size, he quickly deflated and left...

 

[phillo]

Have you ever run across a guy that totally set off your back molars watering, butt, yet, when you finally managed to get him naked, and in a compromising situation, you were still so fascinated/intimidated by his looks/build/whatever, that you were unable to "perform"?

happened to me a few years ago. i hooked up with a really hot greek guy...tall, cute, great body, big dick, 25...i had some performance anxiety. the sad situation at least prompted me to acquire some boner pills that i keep on hand 'just in case'.

 

[nyctopgam]

Lay off the stuffed cabbage for a while.

Guys often fart when I am fucking them. Its the air I pump in during a long bout of fucking escaping, not gas generated by the bottom. Nothing to be embarrassed by.