Where it happened: her bedroom
Langauge: English
Sex: Male
Rating: 5
Category: Straight
In high school one of my best friends, call him Brian, was
very popular, football star, very good looking, etc. I was
shy although kinda jockish, but was nowhere near as self
assured around girls.
Toward the end of my junior year I was talking to Brian
about how I was still a virgin and wanted advice. He
mentioned a girl, call her Amy, a cheerleader who had been
heavily flirting with brian and who had made it clear she
wanted to lose her virginity to him. At this time Brian
had a steady girlfriend and although he was not beyond
cheating, he did not want to fuck Amy. Amy had apparently
told him that she thought I was cute when it was clear that
he did not want to go out with her.
I was reluctant but could not resist going along as Brian
and his girlfriend hooked me up with Amy. I could not
believe Amy was interested in me. She was very good
looking and outgoing. They set up a date that ended with
us with our hands in each other’s pants
but no further because it was late, she had to be home and
it was auckward in a car. we went out a couple of more
times and made out a lot, but did not go all the way.
After like three weeks our chance came, her parents were
out of town and left her alone. I came over on a Saturday
night and we wasted little time getting naked. After a lot
of groping she rolled a condom on me. I was very nervious
and overjoyed too. I felt a little bad that I knew I was
her second choice but I was very anxious to “join the
club” of guys that had sex.
When I entered her (after a fair amount of fumbeling around)
she bled a little which made me even more nervious, but I
was reassured when both her body and words said “keep going”
and “that feels good.”
I guess it was over in 5 minutes after that. After we were
done we hugged and kissed very lovingly and I told her that
I loved her, which, in retrospect I was too confused to
really know for sure.
We dated had had sex semi-regularily (whenever we could
find a place) for about three months afterward. She ended
up dropping me for, yes, a real jock/stud type guy who I
really hated. It hurt terribly, and I suppose a part of me
has never entirely gotten over her but I rebounded in a
couple of months and I’ll always have a “warm spot” for Amy.
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