Awkward Sexual Encounters: Final Round

My most awkward time was with a one-night stand with a fat dude. He was funny and I was drunk so I guess he didn't look that fat with clothes on? Yeah, I couldn't straddle him without serious discomfort and this was when I rode horses. He also wouldn't shut up about his "huge balls and cock" when he was small to average. It was really tough to keep the look of disgusted confusion off my face but any horniness I'd felt at the beginning of the night was rapidly replaced with cynical self-loathing as he just kept blathering about his junk.

I ended up giving him a half-hearted handjob while looking away in boredom.

I used to live with a guy that was a fuckbuddy for a short while, but I got bored with it pretty quick. Somehow he managed to make kinky sex boring, and anything else a chore. Things started off fine, but he had habits that he seemed to pick up from excessive porn-watching that started to surface, like a constant stream of dirty talk or attempting to spit on his hand and use it as lube. A little dirty talk now and then is fine, but he wouldn't shut up, and the spit thing was just disgusting.

It had been a few months since we'd last had sex with each other when this happened. We came home from visiting friends, it was late, and I hadn't slept much the night before. Sex was the last thing on my mind. Unfortunately, it was the first thing on his.

Everything seemed normal at first, then he suddenly turned into an emo kid and wanted a hug, so I said fine. Whatever. But as he was hugging me from behind and sniffling, I felt something move and start poking me in the back. I cringed. He started blubbering about something, but he was whispering so I couldn't tell what he was actually saying. Then he started kissing my shoulders. Constantly. Little, tiny pecks here and there, for the next five minutes. It was sad and embarrassing, and I really wish I'd thrown him off of me. I'm still not really sure why I let him have it, but I kinda figured it was easier than dealing with a weepy grown-ass man all night.

So, so wrong.

Foreplay progresses, with me barely paying attention, and him whispering more incoherent dirty talk at me. I was kind of glad I didn't actually know what he was saying, but something kind of stuck out. I could have sworn he said something about "your cock," and last I checked, I don't have one. Finally, morbid curiosity gets the better of me and I ask him to repeat himself.

"I want to suck on your tongue like a cock."

Fuck. I nearly cried.

Sex did happen that night, but it was incredibly awkward and I sure as hell did not finish. He spent the rest of the time he was on me telling me that he wanted to suck a cock, over and over again.

The final insult to injury: As I was laying there, trying to sleep and not think about what just happened, I was woken up twice because he was jerking off, breathing heavily, and the mattress was wiggling. When I got up, I took a shower, and walked out to ... him jerking off at his computer, watching porn, with headphones on. I never confronted him about it because I really didn't want to think about it.. Like was he still thinking about me, or sucking cocks, or both, or ...

I was making out with this dude on a park bench at night, sadly thinking of who I'd rather be with since the guy wasn't exactly exciting. Had a butthole mouth, terrible tattoo, personality that didn't really mesh with mine ... also thought he was debonair.

I was trying to think of ways to end the night when suddenly a spider crawled out from under the bench and ran across the concrete path into the grass. Loving critters, I broke off the kiss and was all, oh cool! A spider!

He made a weird sneering laugh and said this to me all sexy-like:

"The spider heads for the warm, wet grass. He'll get there eventually."

He then felt up my thigh. But I didn't understand. It was a cool night. There was no dew on the grass. The grass certainly was not warm. The spider was already in the grass. What the fuck nonsense was this? I told my friend later and he laughed and told me the dude wanted to finger me.

grass = my vagina
spider = his hand

Oh, how romantic.

I was with this girl that I had known for quite a while through school. We were hanging out in my room after having had a bit to drink. We were making out and one thing led to another. I was a virgin and had no experience really, so I was kind of nervous. Suddenly, I get the great idea of talking dirty to her while taking off her clothes. So it was probably the alcohol talking or whatever but for some reason I thought it would be sexy to tell a fucking knock knock joke. I said "Knock Knock" and she seemed kind of surprised and just said "what?" I told her to go with it and we had this exchange:

Knock Knock
Who's there...?
I want to ravage your ass
I want to ravag-
I wasn't telling you my name.

She seemed really taken aback by this remark and just kind of stopped. I apologized but she got dressed and left hurriedly, not really saying much.