Awkward Sexual Encounters!
I was having sex with a new guy, and I was on top and things were going pretty decently considering we were both pretty inexperienced. He hadn't been saying much, which was fine, but all of a sudden out of nowhere he moaned "I loooove fucking your assssss."
I basically just stopped moving and I said "What? You...aren't," and he got really flustered and replied with,"Oh God! Ohhh God. OhmyGodforgetIevensaidthat. Keep going. Forget I said that. Keep going."
I really have no idea where the fuck that came from or what was going through his head. It's not impossible that he was fantasizing about doing his best friend in the butt. They were a little too close.
My first time with a guy with an uncircumsized penis was memorable. Granted, I paid attention through the sex-ed classes we had that were more informative than the ones today, so while I was intellectually aware of the foreskin, that hadn't prepared me for actually dealing with one. We were on the couch making out, clothes coming off and I was stroking him and half-noticed the skin sliding back. Since it was sliding forward I wasn't concerned until I slid it past the ridge and it wasn't sliding back.
Immediately I freaked out into hysterical tears completely convinced I'd broken his dick.
Once he calmed me down enough to find out why I was freaking out and showed me it will still slide back, nothing's broken, we resumed where we left off.
At least I can laugh now at it but at the time, I was scared shitless.
I fucked this chick who worked a late-night shift at Burger King in the back of her car during her break. Like, I didn't know her name or anything. I had just gone through the drive-thru several times whilst drunk and flirtatious. But yeah. That wasn't really the awkward part. We ended up exchanging phone numbers. She gets a hold of me the next day and I go over to her house. When I get into her place, I almost immediately want to leave. She had two really young kids, both of them dirty and smelly, and intense amounts of Jesus pictures and crosses. The light-up neon one scared me the most. I sat in there for a while as she tried to get me to feel her up in front of her kids. I eventually made some excuse about something and ran far, far away.
There was a girl I was interested in in college, so I was trying to pump her friends for info. One of them was a midget who would only talk to me if I promised to give her a back rub.
I was sitting on a couch and she was on the floor in front of me. She turned around to tell me something and put her hand on my leg, brushing my wallet near my mid-thigh. Her eyes went wide and she asked me "Do you have a boner?"
I wanted to shout an emphatic "No!", but I was afraid that if I protested too loudly she'd think I was a little-person hater and it would hurt her feelings. So I mumbled "Why?"
She immediately took off down the hall telling all the girls in the dorm I had an enormous 11" wang. I do not know why. I tried to protest that it was my wallet, because I was afraid that this false preconception would only lead to disappointment later. My denial only made them believe it more. This would have been awesome if my life were a raunchy college movie, but in reality I got a lot of attractive girls smiling at me knowingly but remaining unapproachable because they thought I had a midget fetish.
Another time I was having drunken sex and got it into my head that I would somehow blurt out the wrong name. Then, because I was drunk, I decided that if I called out the wrong name on purpose for comical effect everything would be fine and the pressure would be gone. The trick was to call out a name so improbable that it was obvious I was joking. So, at the moment of climax, I yelled out "Dan Marino!" before laughing hysterically and passing out.
As this was only months after the previous incident, it did nothing for rumors that I was a sexual deviant.