People Share Their Most Awkward Sex Stories. Cringe Warning!

The first time I attempted sex WITH a condom I was so nervous/inexperienced that I got out of bed, went into the bathroom to put the condom on, put my boxers back on (condom still on) and crawled back into bed with the girl. She ended up laying on top of me for about a half an hour giving my hickeys all over my neck. Never actually put it in. The next morning it looked like I had tried to hang myself. The first time I attempted sex WITHOUT a condom I ejaculated instantaneously upon insertion. I was so embarrassed that I immediately told her that "we shouldn't be doing this, it was simply too risky without a condom." Sweet girl, never called me out on my one pump chumpery.


I was an inexperienced teenage kid and slept over at my girlfriends house for the first time. We were quite horny and a little drunk so we ended up having sex, we used a condom. After the business was over we had this condom to take care of. We didn't want to put it in the rubbish there because we were scared her parents would find it. We agreed that I would take it and throw it away somewhere on the street but since it was so nasty and slippery I wanted to put it in a bag or something and not directly into my pocket. She didn't have any plastic bags lying around so instead we put it into an envelope from the bank used to send stuff like accept giro's (like credit slips) to the bank. I stick the envelope into my jacket pocket and, after a while I go home. On my bike ride home I see my parents car at the end of the street coming towards me. I thought my parents would be pretty damn pissed since I didn't tell them I was sleeping over at my GF's house. Scared shitless and paranoid they would find the smudgy envelope and ask horrible questions, I look for a rubbish bin but see nothing but a mailbox. So I mailed the condom to the bank....