I had my first non-solo orgasm with my boyfriend when I was about 16 or 17.
I was in my last year of high school, he was a year or two older, was at university.
Unlike other girls of my age, our dates involved going out for dinner. I don’t know why. Maybe I saw it in movies and insisted that that was what a date looked like. We would mostly go to a pub that wasn’t too far away and eat in their bistro. I’m sure I thought it was terribly sophisticated. I can’t recall if we would go to a club to dance or something afterwards.
At the end of the night, we would inevitably go and park by the bayside, views of the water, and I have vague recollections of the back seat. We weren’t having penetrative sex. I wasn’t ready for that. No doubt he wanted to, and probably hassled me a bit in the way horny boys do. I really can’t remember.
There was kissing (lovely!), touching, rubbing, oral (on me, I don’t remember reciprocating), always culminating in an uncomfortable boring hand job, he’d come and phew, it was done. While I liked the physical sensation and would get aroused, overall it was not enjoyable, not sexy, not something I looked forward to. I thought it was kind of ‘icky’. Maybe I thought it would get better as I got more experienced. Or maybe I just thought this is what you did. Or some combination.
In short, I’d guess it was pretty typical of the way that many early teenage sexual experiences go.
One day we were sitting in my living room and goodness knows I have no recollection of how this conversation started, but he asked me if I came with him. I looked at him as if he was insane. It never occurred to me to lie about it.
He was genuinely shocked by this. I never faked it, so I don’t know why he was so surprised. I had always assumed (we never talked about it) that he had much more experience than me, but in hindsight, I now wonder if that was a mistaken assumption on my part.
He was disappointed with himself and felt bad for me (his heart was in the right place, bless), so he offered to go down on me there on the living room floor in the middle of the day. My parents were out, I said okay then (how sexy, right?).
He did, and I concentrated. Hard. I’d come a million times on my own, but never with another person and there were a hundred voices in my head getting in my way. It seemed to take forever, and I had to fight not to stop him for fear he was bored or over it or it wasn’t going to happen. And finally I came in his mouth.
About 2 seconds after that we heard my parents come home, so we grabbed up all of our clothes in a panic and scuttled into my room to hurriedly dress.
When I ended that relationship, I still hadn’t had penetrative sex. I still wasn’t interested in it. And despite my orgasms (I assume I had more with him but I can’t remember that either), the sex we had was still not fun for me. I still never felt what I thought I should be feeling. It felt kind of like a chore that went with having a relationship, and this even though he was a caring partner who was genuinely interested and concerned about my pleasure. It just… didn’t work for me.
And then, I fell in love with another woman, and learnt what sex *should* feel like.