The Virgin Queen

Growing up, I was freakishly small and no one paid attention to me. There are always some-those gnomes of the schoolyard running in slow motion toward puberty. We sad sideshows were the same as our peers emotionally, if not physically.

In junior high, I shaved my legs and wore a training bra, which by the way, was too big in the smallest size. I always wore a T-shirt if there was going to be any swimming, until one pool party when Ben DeCroce convinced me to doff my cover-up only to respond in disbelief, “Wow, you really are ﬂat!” And even though there’s no audience of cruel eighth graders (whatever, Ben, like you were some prize with your gross glasses and chinlessness) to stare in appalled silence at this story and all its shirtless flatness, the spirit is the same. Take that, Holly McKinley, who was fully boobed and pubed by age thirteen and getting it on with a twenty-two-year-old.

When I got to college I did what any inexperienced, nubile virgin would do: I overcompensated. I made a habit of sneaking up on my roommate buck naked and jumping on her lap, preferably while she was wearing shorts. I gave ball gags and nipple clips as birthday gifts. I even had a squirt gun with a rubber penis-shaped barrel with which I would accost my neighbors in the elevator. Basically, I was a low-level sex offender.

By this point I had some suitors, but none that suited me. It was the new millennium, and I was twenty. I had a brand new best pal, Tyler, out of the closet since age fifteen. He’d recently finished playing the role of Jesus in Jesus Christ Superstar, and we spent many afternoons contentedly watching Ab Fab or listening to Dar Williams, before he made his surprise move. Perhaps it was my boyish figure, or my overt penis envy—who can say? But for whatever reason, Tyler, who had never so much as glanced sidelong with lust at a lady, made an overture. I went with it.

“But he’s gay!” you’re thinking.

I ignored this fact.

“Would it be weird at school?” Tyler and I wondered.

It would. Our friends were baffled, scandalized, at times angry. Turns out, once you come out of the closet, you’d better fucking stay there. But love sees no sexual orientation, and we only had eyes for each other.

We did, however, encounter one large obstacle.

Tyler happened to be endowed with something that even I, with no frame of reference, understood to be a massive, mastodonic cock. A Boogie Nights cock. Nine and a half inches of solid, stout flesh. I can describe it as a hoagie. I can describe it as Jason Giambi’s head and neck. A veiny, hulking schoolyard bully of a cock.

Here’s the thing. Contrary to conventional wisdom, this is not always good news. It’s especially bad news if you’re a five-foot-four, ninety-five-pound virgin. How would this work? Tyler was very stressed about it. I assured him I would be fine and internalized my fears, but I knew I needed to do some stretching exercises. I needed to prep. But how? How, how, how?

Remember the squirt gun, guys? The one with the penis-shaped barrel?

I lost my virginity to a squirt gun.

I stuck a squirt gun up my no-no. I rolled a condom onto it and gave it my flower.

There’s more.

Having left my virginity behind, I then convinced my gay boyfriend to give me his—five years after he came out of the closet. To set the mood, I put on the Backstreet Boys’ “Millennium” album, which may be the only choice I made that night that I don’t regret.

The problem was, the squirt gun I’d made love to was probably only a third the size of Tyler’s dong, which just wouldn’t . . . go . . . in. It just wasn’t happening. I sat down on it, and it was like sitting on a bicycle seat. Uncomfortable, but exterior. It was like a barstool. So. We did what two twenty-year-old virgins—one gay, one straight—would do.

We improvised.

We didn’t have a lot of time; Tyler had rehearsal for Tommy in forty-five minutes downtown and would already need to take a cab. We didn’t have any actual lube, so we threw out some ideas. Hand cream? Sunscreen? Hair gel? Hmm. Did I have any butter? Yes! Yes, I did.

So I retrieved a stick of butter from the fridge, and we copiously buttered Tyler’s French roll. We buttered Tyler up and down and all around, and we gave ourselves to each other. And I will say, it was in its own way magical, on my dorm room twin bed with Nick Carter’s crooning voice in the background. We laughed our way through the whole thing, and I wouldn’t have it any other way, save one.

Don’t use butter as lube, guys.

A couple of fun facts about butter:

1. Butter is corrosive. The butter ate right through the condom, which was then shredded around the base of Tyler’s biggie-size, battered penis.

2. Butter contains bacteria. I stopped dry-heaving from the morning-after pill just in time to notice an uncomfortable sensation downtown. A vaginal infection of epic proportions.

And that’s how I lost my virginity to my gay, almost-baby-daddy’s nine-and-a-half-inch cock to the song stylings of the Backstreet Boys and ended up with a monster crotch infection. Except that I had already given it up to a squirt gun.

Excerpted From Worst Laid Plans, edited by Laura Kindred and Alexandra Lydon (Abrams). Republished with permission. Got a bad sex story? Share it here and win a copy of the book.