This story isn't really that awkward, but it could have consequences in the future. So I was dogsitting for a really good friend of mine after he had gotten married which meant that my girlfriend and I had a place where we could have some loud, fun sex because I live with 5 other guys and she gets embarrassed. Anyways, we cook dinner, have a few beers, and watch Grease. Finally, we're getting ready to go to bed. At the time, I was feeling like a straight homeowner. No fooling around on the couch, nothing, just light making out. Anyways, so we get into bed, the lights go down and we start getting serious. First off, my friend's dog, which is a giant, spoiled Husky kept trying to get into the bedroom, and then when we let him in, he sat on the bed and watched us. So I get on top of her, and we're both kind of drunk, and she's a little dry, but I figured it would pass. So I start picking up speed and I feel a sharp pinch right on my dick, her vagina starts to feel really wet, but I'm losing my boner. I'm thinking "what the fuck, after all this I'm gonna just go limp mid stroke?" I pull out because she says it doesn't feel right either, turn on the light to see my dick covered in blood, my blood. I'm uncircumcised, and it's right where the extra skin folds down. A lot of thoughts are going though my head, most importantly "will I be able to skate?" so we clean me up and laugh about it. Next day see that all the blood that leaked from my mangled cock had soaked into the mattress, and I spent the whole week cleaning it off with bleach, I also stole a pair of my friend's boxers that I have yet to give back.
They moved recently and didn't mention anything about the stains that were still clearly on there.