Where it happened: His house
Langauge: English
Sex: Female
Rating: 5
Category: Straight
I’ve only been with women (I don’t know if I’m gay or bi or what — don’t like to label it) as I’ve gotten older, but my first was with a guy. We met in junior high, and dated for a couple years. His name was Jeff. Sweet guy. We met on the track & field team.
It was sophomore year, we’d been going out for a while now. We did a lot of kissing and touching each other, but that was starting to get old for him. He asked me one day if we could go further, and I said yeah, sure. Kinda casually leaped into it.
His parents didn’t usually come home until the evening, so we went to his house right after school one day. I’d like to say it was some big, beautiful romantic moment of passion, but the fact is it was awkward as hell.
We both took our clothes off, slowly (I had never even gotten naked around another person before, not since puberty began anyway), and for a while we just sat there on his bed. He had a huge boner but didn’t seem to know what to do with it. I hadn’t asked, but it was now pretty obvious — it was HIS first time, too.
Eventually I lay down on my back. He got on top of me, and started kissing me all over. It was pretty aimless. I tried to look like I was enjoying it. I don’t know if maybe he was ‘faking it’ a little too.
Then he jammed his cock into me, and oh my god, that hurt SO BAD. I couldn’t pretend I was having fun anymore. He pulled out immediately — he looked so scared — and that hurt, too.
He asked me if I wanted to stop, and I told him I wanted to just take a shower first and see. So I did, and I started to feel a little better there. I came back to his room and he was still naked (clear he didn’t want to stop!) and I gave him a little hug and told him not to feel bad. I told him if he went REALLY REALLY SLOW, we could try it again.
And we did. This time it wasn’t painful, just awkward. He eventually did work every inch back inside me again, and this time it felt great! He thrusted a few times, and shot his load inside me (didn’t know it at the time, but it turns out I can’t get pregnant, so we lucked out there!). I took another shower and made it home before either of our parents knew about it.
Jeff and I did it 20 or 30 more times before we broke up the next year. He got a lot better at it, I’m glad to say (some of the things he did with his tongue, mmmmmmm). I’ve never had sex with another guy. I wonder if I will, because the memories aren’t too bad.
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