So it was a girl from work. She was in her late 30's.
She was our admin assistant. We got on well at the office. One night after work we went out for drinks (going out for drinks after work was a common occurrence with people at this place). This time it was just us. We got to talking and she mentioned that she had never had an orgasm. I ask why, if it was just lousy partners or what. She says she was a virgin and never had the chance and she couldn't get there on her own..
I'm not sure if it was the booze or what, but I jokingly say: "lemme know if you want a hand with that". I was mid 20's at the time, and although I was no Casanova, I had been in a few long term relationships so I had some experience.
About two weeks later, she texts me, saying she wants to take me up on my offer. Being in a dry spell, I figure "why not?". So we set a night. We get together one night and decide to have some booze and play vids to lighten the mood. She proceeds to drink about a litre of vodka (approx 1/4 gallon). We were having a good night, but I questioned her consumption (I was also drunk, but I hadn't had that much). She said it was a regular thing, and could handle it. I thought it wasn't a good choice, but I kinda believed it based on her performance at past drinking nights.
Anyhow, the time came and we were fooling around. She kept pulling off the condom, and I asked if she was on the pill. She said no, so I kept rolling the condom back on. At one point, she rolled it right off. Being drunk (and in the dark), I decide to grab a new one, but went to the bathroom so I could see what I was doing (she wanted the lights off). I proceed to hear a gushing noise. My previous girl was a gusher, so I kinda knew the noise. With a grin on my face, I return to the bedroom with a smile on my face thinking she had finished herself off and that was the result.
Needless to say, she in fact had far too much to drink and proceeded to vomit all over my bed, the rug, the curtains... everything.
I cleaned everything up and put her to bed. She was mortified the next morning, but I comforted her and told her it was our secret (which it still kind of is, this story notwithstanding).
We got on being friends and tried once more. I'll save that story for "bad sex |OT2|" (note: it wasn't nearly as bad). I haven't heard from her since the second time.