Awkward Sexual Encounters!

Before Vera "Viconia" Lynn left her Comedy Goldmine position to explore uncharted realms, she left me an untapped 71-page thread called "Sexual Encounters Gone Awkwardly Wrong." As parting gifts go, it's marginally preferable to some of the diseases people in the thread bemoan having received from their exes. A lot -- too much -- of the thread is basically Goons saying "SO I WAS HAVING SEX and it was WITH A GIRL and SHE LOVED IT and, oh, wait, 'awkwardly wrong,' um one of us farted i guess." But I read until I'd reached my threshold of disgust and ennui. Then I realized that I hadn't gathered enough content from the first half-page to make an update, so I forced myself to stick with it, much like many of the submitters soldiered through gross intercourse. Maybe if people enjoy this then I can read some more and put together a second installment. Hooray/goddammit.

I once awoke to my ex-boyfriend slyly trying to slip his dick into my ear. I really didn't know how the fuck to react.

I still remember the expression on his face.

Well, it wasn't so much as 'sexual,' given that it's a goddamn pissing irritating platonic I-love-her-but-she-doesn't-look-at-me-in-that-way relationship, but having a morning 'hello hello' hug, while we're on holiday together. She shifted a little, and I came.

While fully clothed.

Goddamn I've not lived that one down yet, even though she's never mentioned it since. I like to think my "well does that count as losing my virginity " remark post-cleaning helped, but something tells me it didn't.

If you are a guy, and you haven't had a girl stomp on your heart, then light you on fire, you're missing out. It should happen to all of us once.

Regardless, the first time this girl broke up with me (it happened twice) was literally at the moment of mutual orgasm. In the moment of ecstasy she dropped "I don't love you anymore."

That was fun.

I hadn't been laid in a while, so being the desperate asshole that I was, I checked on craigslist to find an easy lay without having to actually go out and do anything. I end up finding this ad for some 26-year-old lady (I was 19 at the time) who says she was looking for a someone to come over occasionally and have sex with her, watch movies, whatever. So I respond and she says I sound good. So we make plans and set a day to meet up. Now, she sends me a picture of herself and she is by no means skinny. She is also not morbidly obese. So I just didn't really think anything of it.

A couple days later, I make my way over to her house. I live in a fairly small town and she just happened to live in like the shittiest neighborhood there. Her apartment complex was falling apart and there was shit all over the lawn and whatnot. I get into her house and it's not any better. It also smells like cat piss and old food. Oh, and she forgot to mention that she is married and has two kids. He husband was aware of what was going on and was not only cool with it, but also wants to watch. At this point I already feel really weird about it, but not wanting to make the situation even more awkward (and also wanting to get my dick wet) agree to the terms. Anyway, we go at it while her husband is playing WoW in the same room. The sex was terrible. She smelled bad and sent me an old picture. Jesus tapdancing christ she was large. It took me what seems liked forever to get off. I finished up and left. Went home and showered, cried a little and never called or contacted her again.

We were both Star Trek fans. That was something we had in common. But that one time we had sex, we were in the middle of it and she said "fuck me with your big Klingon Dick, Worf!"

She was then really confused why my erection suddenly went away.