I promised a while back that I would tell the story of how I lost my virginity. People just love telling these stories anyway, but I’ve always found my initiation into intercourse to be particularly amusing. To me, at least, and hopefully for some of you as well.

Somehow or another I got to be twenty-one and was still a virgin. How did it happen? Well, I didn’t want it to be part of the sticky 15-year-old fumblings in highschool, wanted it to be special and maybe even romantic but of course the older I got, the more special the guy had to be, because I’d waited so long. Basically, the task grew more arduous with every passing year, and before I knew it, it wasn’t something special, it was an albatross hanging around my neck.

About the virginity. I should explain. I think I may have made it clear above, but in case I didn’t we’re talking technical, coital virginity here. I’d been fooling around with boys for years, knew what a cock looked like and felt like and tasted like. Just hadn’t had one inside me before.

And then there was Marty. He and I had been good friends for years, hung out, had fun together. He was absolutely adorable to me. He was also bisexual.

Somehow I got it into my teeny little 21-year-old brain that a bisexual buddy would be the best man in the world to give my virginity to — he was comfortable with sexuality, he was comfortable around me, and he wouldn’t fall in love with me or want to go steady or anything. He’d also be careful with me because we were good friends. He even carried condoms with him. This was my logic.

So one night we’re hanging out at my place, talking, listening to music, drinking a little, and I ask him if he’ll do it. After some discussion, he says, “sure”.

We pull out the bed hidden inside my big L-shaped sectional, and lay down on it. Some kissing. Some dry humping. And we decide it’s time for the big moment.

We get undressed. We kiss a little more. He tells me it would be easier for me the first time to be on top, that way I could go as fast or slow as I needed, to control the pain.

So I get on top. And I’m just kind of straddling him, waiting, because I don’t really know what to do.

He tries to push it up inside me.

It hurts. It feels waaay bigger than I expected.

Turns out it feels that way because Marty has gone soft, and he’s trying to push it up there anyway. Unsuccessfully.

It becomes obvious to both of us that this isn’t working. But we’re dogged kids in our early twenties. Must be some way to make this work.

I lick and suck him, trying to make him hard. He’s just floppy in my hands. So much for my oral skills. 🙂

He starts stroking himself, but as soon as he removes his hand, he loses his erection. He digs in the pocket of his jeans and produces a cock ring (my thirty-one year old mind is saying cock ring? what twenty-three year old boy carries a cock ring in his pockets every day?). He straps it around himself, and starts jerking it again, trying to get hard. Somehow, the cock ring breaks.

Desperate, he asks me for a hair elastic.

Confused, still hoping to lose my virginity, I go get him a scrunchie, which he proceeds to wrap around his cock and balls, and tries again.

Nada. Zip. Zilch.

He decides that I should just get on top anyway, and hump him a little – should perk him up. So I do. And once he’s reached semi-hardness, he grabs it with his fist and tries to shove it up there again. Ow.

At which point—you guessed it—Marty loses his erection again.

By this point I’m pretty upset. And feeling more than a little foolish. I tell him to forget it, that it’s just not going to happen. We sit side by side on the bed for a few moments, not saying much. Which is when it hits him. Like a lightning bolt from the sky.

He’s not bisexual. He’s actually gay.

He never knew this about himself. It’s a revelation. Sure, sure, sorry about the whole losing the virginity thing, but Vikki, wow! He’s gay! What does this mean?

We wrap ourselves in blankets. I pour us each a strong drink, silently. And we head out to sit on my balcony.

We sit there all night. I don’t say much. He talks and talks about this wondrous discovery and re-examines every sexual and non-sexual relationship he’s ever had, looking at it through these new eyes. Till 5 am. My self-esteem slides down and ends up in a puddle at my feet.

In trying to lose my virginity, I helped a man discover his homosexuality. 🙂

It sounds sad, but honestly, in retrospect, it’s one of the funniest moments of my life. I run through the story in my head, and by the time he asks for the scrunchie, I’m in tears from laughing so hard.

And so ends the tale of part one of losing my virginity. Part two soon.