So today, a guy I used to mess around with hits me up. He had this 18 yr old guy that wanted to fuck me while he watched. I was game for it, so I met him at his place, the kid was already there in his boxers watching a straight porn flick.
He was a cute skater type, shaggy brown hair and a slight five o' clock shadow, with at least 7 inches poking out of those boxers. Our host told me to get busy on the kid's meat, so I undressed and started to suck him till he got totally hard. After about 10 minutes, he was ready to fuck. I got the lube out, when he asked for a condom. At this point I was torn... I SHOULD be wanting to be safe, but that "other" side of me wanted him to just shove it in.
He put it in me, and while it DID feel good after a few minutes it started to get very uncomfortable. The condom started getting all folded up, and the lube was wearing off. Both made it very uncomfortable, since all I could feel was the damn condom scraping against my hole, instead of the kid's dick. He wasn't receptive to going bare, though... so I put up with it, for an hour. So while my hole is sore from fucking, it's not the good kind of sore. Yeech.