Shortly after my 16th birthday, my girlfriend of about 6 months invited me over for the day.
We had up until that time been sexually active in every way except for actual intercourse. We had traded pictures, I had fingered her, eaten her out, received head, as well as hand jobs but neither of us had really broached the subject of sex.
In retrospect I probably should have pushed the subject a little more, but in all honesty had been fine as long as I came. So it didn’t matter as long as she was the one to provide it, for it did heighten the experience to have another do it instead of oneself. I saw sex just as another form of this and nothing more.
Anyway the day I went over her mom was out at work and we had the place to ourselves, so naturally as we had done many times before we began playing truth or dare. Each dare getting a little bit raunchier. The excitement was building; each of us had been pushing our boundaries and feeling one another out. Finally she told me that she had wanted to have sex for awhile and had specifically chosen for me to come over that day because her mom was out. So we went into the bedroom, all of our earlier excitement and energy having faded we undressed, and got into bed.
She got on top of me, put a condom on, and pulled the covers over us. I slid in and we began slowly to rise up and down. She grimaced a bit and we took it slow; it ended up lasting about 10 minutes. I remember thinking I would rather get head than this as it provides a lot more pleasure; because it was so tight it hurt her so we went really slow.
But we ended up doing it a second and a third time and a fourth time and jesus christ did I like it after the initial hesitation.
—M.O, male, 21 years old