I had been crushing on a girl I went to High school with, “Susan,” for about six months.  We had made out a number of times.  She told me she liked someone else, but still would make out with me.  Sigh. So we continued to make out.  I got pretty sad, and decided I shouldn’t erode my self-esteem like this, and we stopped making out.  We were still friends but with baggage.

We continued to hang out through the summer, me feeling the same way (crushing) and her seeming to like me more and more.  We started dating, which I was ecstatic about, and resumed making out.

Her ex-boyfriend, a mutual friend of ours, had dated her for about a year before she and I got together.  She wanted to have sex and he said he wasn’t ready.  She brought this up to me, about a month into our dating.  Me, in my new-found relationship status, agreed whole-heartedly we should have sex without ruminating on the consequences.

The Act

At her house.  We fooled around for about an hour. Had a breathy, teenager moment of “should we?”  “I dunno.  I want to.  But. . . I dunno.”  I had brought a condom (never a boy scout, though) and we fumbled our way to our respective first times.

I came almost immediately and was mortified.  I tried to fake it (unconvincingly).  She noticed the sensation changed and wanted to switch positions.  In the attempt to switch me-on-top to her-on-top, I fell out, devastatingly flaccid.  Her response was a look down and a weighty syllable “oh.”

Yes, I think I had sex too early.  I hadn’t had much experience with physical affection or emotional intimacy before, and my first go at it didn’t end well (see above). It gave me an aversion to sex and a stigma about stamina and what sex is “supposed to be like.” It didn’t affect my family or social life much – partly because it wasn’t ‘open” that she and were sleeping together (high school stigma of promiscuity and all).