Where it happened: My bedroom
Langauge: English
Sex: Male
Rating: 5
Category: Straight
Well, it was Christmas 1991. I had been dating this girl for a few months, and we’d messed around a few times but never gotten too far.
My parents were downstairs watching a movie, and we went up to my room to watch a movie. Of course I knew we’d fool around, but it went farther this time. She told me she’d been wanting to try giving me a blowjob for a long time and I certainly didn’t stop her. In retrospect, it was quite possibly the worst head I ever got in my life, but at the time it was the coolest thing I’d ever experienced. She asked me if I would return the favor, and I obliged. After I had gone down on her for awhile, I (being 13 and thinking I’m slick, of course) casually mentioned that I “could’ve slipped it in by now” but I didn’t really expect her reply of “well, why didn’t you then?” HOLY SHIT!
I owned one condom. I had bought it from the gas station bathroom weeks before… I don’t know why. I used to fill it up with water while I was in the shower, and try it on, and masturbate with it on and such. I always just rinsed it out, then hid it in the battery compartment of my little boombox until my next shower/bath/whatever. I ran downstairs and grabbed it, rinsed it off (for good measure, I guess) and went back upstairs.
She asked me if I had the condom and I told her I did. She took it from me and said “it’s already open?!” I looked at her sheepishly and said “it’s all I got” and she sat there for a minute, then started rolling it up then put it on me. She laid down on her back and spread her legs and I crawled on top of her. “Slow” is all she said. I had trouble finding her opening, I must have mashed the hell out of her clitoris, but I finally managed to penetrate her after what felt like a lifetime of panic and embarassment. We had sex for maybe 10 or 15 minutes and I was getting nowhere; I was just way too anxious/nervous to climax. Finally she just looked at me and said “are you almost done, I’m starting to hurt” and that was the dealbreaker for me. I just said “yeah, I’m good” and pulled out. I threw the condom in the trash, then watched her fish it out and examine it. “You didn’t cum” she said. “Yeah I did, it just wasn’t much” I replied. She looked a little hurt, but said we’d try it again in a few days.
Funny… after that, I was riding on cloud 9 for weeks, but now that I look back it was one of, if not THE least satisfying sexual encounter I ever had.
Processing your request, Please wait....
