I was 16. My girlfriend and I hadn't had sex yet. Had been dating about six months, tons of kissing and hand stuff. She had jacked me off to completion before and I had used my hands on her to what I thought was completion. She had given me oral twice, although finished with her hands both times. Both times I offered to reciprocate but she said no.

One time when we were really alone she admitted to me that when we were doing hand stuff she actually hadn't ever had an orgasm. At the time I was shocked and a little hurt (I had only really seen orgasms in porn which are mostly fake so I couldn't tell the difference.) But instead of being mopey or mad about it I looked in the eye and told her I just wanted to make her feel good and we could try other things. She was unsure still but I think the reason she admitted this to me is because she wanted to because immediately after she told me her friend had an orgasm from oral. So I went down there to try it out.

I was terrible at it. I spent way to much time trying to get my tongue inside her and not enough time on parts that actually mattered. She wasn't willing to tell me what I was doing wrong though so after 20 minutes she said we could stop. She was clearly kind of upset and we went to watch a movie. After the movie I told her I wanted to try again and told her I had an idea. I put her hands on the back of my head and told her to pretend I was an inanimate object for her to control. She could put pressure on my head to get me to move up and down or press further or lighten up and we could find out what works together. After about 20 more minutes we both found the groove of what really worked and another five minutes later she had her first orgasm (she claims she hadn't had one solo before that but could pretty easily after.) After that she gave me a blowjob to completion for the first time and later that night I ate her out again.

That was seventeen years ago but clearly a very memorable experience.