Love & Sex

My First Time

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My First Time - Illustration by Thomas Pitilli

Illustration by Thomas Pitilli

Female • 16 years old • Portland, OR

It always amuses me to confess that I lost my virginity in a trailer. The trailer was in the backyard of the near-stranger I had sex with, and in hindsight I think that trailer may have been one of the only private spaces he had in the world. Not an RV, and definitely not a semi-permanent manufactured home, but the kind you hitch to the back of a truck. If I have any misguided pretensions to class, this story always deflates them.

By fifteen, I had my first serious boyfriend, and we shared all the preliminary heavy petting and dry humping expected of that age. We didn't have sex, although our parents were worried enough about our youthful activities that they sat us down for a group meeting in my family church. Somehow we knew it was all a big joke, and my main concern was surreptitiously rubbing my boyfriend's hard-on through his jeans underneath the table.

The next year, I had a tumultuous relationship with a girl that could inspire thousands of personal essays. We attended an all-girl Catholic school and enjoyed being as notorious as possible to our peers without getting caught by the authorities. So technically, I lost my virginity to my girlfriend, an easy trick for teenage girls, who are expected to have exclusive friendships and frequent sleepovers. (Though I consider myself bisexual, it's interesting how I discount my experience with a woman as part of losing my virginity. Internalized heteronormativity at work, I suppose.)

My girlfriend and I loved to dance and were obsessed with disco well before its current revival. We attended every school dance in glitter makeup, platform boots, and too-short skirts, dancing with each other like lovers despite frequent admonitions from nuns and chaperones that our bodies must remain at least a balloon's width apart. Clusters of boys were imported for our entertainment, but we didn't care — until one night, when two boys had the audacity to interrupt us and ask if they could join.

It always amuses me to confess that I lost my virginity in a trailer.

They both had the same common, one-syllable name, which seemed convenient to me, and they had crossed state lines just for a chance at what must have seemed like a sure thing. After ditching their dates, we all danced, and later ended up wandering the streets, trying to escape the constant drizzle of rain. We waited for our ride under the awning of a Thai restaurant; I made out with my half of the duo while my girlfriend chatted uncomfortably with hers a few feet away. Insensitive as it seems now, I escaped to a warm car with my new friend's number, and a clear idea of what I wanted when I saw him again.

A few weeks later, he and I got together with the pretext of watching Pulp Fiction, which both of us had already seen. He picked me up in his grandmother's giant old Cadillac and drove me across the river to her home in a shitty suburb in Washington state. The house was cluttered and worn, filled with aging knick-knacks and soft-focus family photos — not the type of home I was predisposed to admire. A small, dirty white dog ran around spreading its fur.

We watched the movie dutifully and made out a little, but I was dripping wet in anticipation of what I wanted to do. As soon as the credits rolled, he led me by the hand through the dim kitchen, where I distinctly remember a half-eaten, brown banana sitting on the counter, long forgotten. (I hate bananas.)

He swore in the darkness ahead of me and yelled out someone's name, perhaps addressing an absent sibling. Soon I saw that he was directing me around piles of dog shit, not making any pretense of cleaning it up or making his unseen relative do so either.

We ended up in the backyard at the trailer. I don't know why he didn't live with his parents, or why he didn't have a room in his grandmother's house. Maybe he took me outside because of the theoretical lurking relative. His entire existence was foreign to me, as a relatively sheltered prep-school girl. But I didn't care. I knew he could give and take what I wanted.

The trailer was covered with clothing and clutter on every available surface. As a teenager, I was no stranger to clothing on the floor, but this was a mess beyond my comprehension. I couldn't process my surroundings, so I shut them completely out of my mind, dismissing them as part of the package of the experience. He led me to a bench-like bed toward the back that wasn't completely coated with dirty laundry. We resumed making out, and from there on my memory is hazy. I remember shaking from cold or adrenaline or both, and being so wet that I was soaking through the crotch of my skin-tight '70s jeans.

Eventually I removed my pants and climbed on top of him, grinding away through my lucky pair of baby-blue vintage panties. He rubbed his dick on the outside of my pussy, and I pushed my underwear aside. Pausing for a moment, he asked, "Are you sure this is what you want?"

My response was to shove him inside me. It felt exactly how I thought it would feel, especially since I had been using a dildo for years. Maybe it was wetter, sloppier. I rode him as best I could with us both in our underwear on the narrow bench. (It's funny to me that I lost my virginity on top — it's still one of my least-favorite positions.)

I don't remember much else — I'm pretty sure he flipped me onto my back and finished himself off, or that could be a piece of another memory transposed incorrectly. I knew I wouldn't come — already I was smart enough to estimate the skill level of boys my age as low. I was pretty happy with myself for getting rid of my heterosexual virginity, something I saw as a hindrance to the development of my sexuality. Frighteningly, it didn't bother me that we didn't use protection, or that he drove me home soon after he finished. It didn't hurt for a second, and I didn't expect anything else from him — I was more worried about what my girlfriend would say when I told her. I never heard from him again, and our relationship of mutual use never bothered me.

I wouldn't change the experience at all, except for how it affected my relationship with my girlfriend. Yet I know it's ridiculous and unrealistic to expect my adolescent self to have communicated as an adult about an open relationship. I'm lucky to have had only positive experiences with sex, and proud of myself for continually finding what I need while avoiding too much danger and pain. And yes, you can have casual sex, be bisexual, and have meaningful, long-term, deep relationships. Sometimes you just need to get the basics out of the way first.