My First Time

Illustration by Thomas Pitilli

Female • 16 years old • Andover, MA

I lost my virginity during an argument about socialism.

I was always a pretentious kid, so the fact that a political argument got me heated in more ways than one wasn't surprising. And the guy I was with, Jesse, was everything a teenage girl could want: tall, dark, handsome, older... and obsessive compulsive, but never mind. Even at sixteen I knew that sometimes, in love, you had to overlook the little things. At least I knew his hands were always clean and well-manicured.

I had known him for years. We met in an alternative school, when I was a twelve-year-old depressed Goth-in-training and he was the moody poetic genius I read about in my dogeared Anne Rice novels. An Armani-wearing "poor little rich boy" cliche, Jesse was the excitingly advanced age of fifteen, and of course knew everything about everything. I was smitten from the beginning, but he was always out of reach. We talked all the time, but I worried I had become his friend with no hope of being anything more, especially since I was insecure about my body. It had betrayed me, going from slender and prepubescent to hourglassed, which, to a teenage girl, means fat. So I crushed in silence and hoped in that terribly Goth way that one day he would see my suffering and tell me he loved me back.

Four years went by with me holding a torch for this boy. We changed schools, and, since this was before everyone had internet or mobile phones, we constantly wrote letters to each other. He had a penchant for the dramatic, writing on heavy paper with calligraphy pens and stamping his notes with his own, personalized wax seal. It was all stupidly romantic, mostly about our worldly concepts and our plans to change humanity. Jesse was born into a wealthy family, while I was fighting through on my own — with his money and my passion, we thought we could do important things.

One letter in particular changed everything. He wrote to me while I was in boarding school, saying that someone he knew had a dilemma. This person loved three women. One was his soulmate, but it was unrequited; one was familiar but the passion was lacking; and one was an enigma. Who should his friend pursue? I was no idiot — I knew this was about him and, potentially, me, if I could figure out which one I was. I took a stab in the dark and wrote back, "He should go for the enigma. Why chase the girl who doesn't want him, and why stay with someone he doesn't love?"

Soon we had our first date. I was ecstatic and probably overeager — I hadn't yet heard that Cosmo propaganda that all men prefer to pursue, so I was upfront about my excitement. Our first kiss was deep and sweet. I felt safe, mostly, with just a touch of fear of the unknown to keep it interesting. He asked me what I liked and didn't like, what I wanted, giving me agency in a way I hadn't experienced with other boys. Slowly dates turned to snuggling at his home, discussing the political news of the day.

And that's how I lost my virginity — crosslegged on his bed, spouting idealistic nonsense about how socialism could work if only we tried hard enough. Jesse deftly refuted my argument, I retorted, and the next thing either of us knew we were kissing, hard. My shirt came off, then his, then we tried to remove each others pants but gave up and, giggling, removed our own. He kissed my neck, biting gently while I moaned and writhed under him, my nails digging into his pale skin. His lips pressed against mine as he slid his hand into my bra to feel my breasts.

I remember not feeling self-conscious. I felt safe. I had known him for years, forever in high-school time, and I loved him dearly. I didn't try to cover my belly as I would later in life, when I again struggled with body image. I just let him touch me, and touched him back, marveling at how soft his skin was and how sensitive mine was. One hand slid into my panties, and he looked at me, as if asking for permission. I nodded, and he slowly pulled them off me, kissing my thighs as he went. My foot got tangled in them at one point but they were eventually removed and on the floor.

He put a condom on without asking, without being cajoled. Years after I would realize how precious this behavior was, and how it demonstrated a respect for me and my body that was rare. Jesse had a small bottle of lubricant next to the bed, and used some on his fingers to get me even more aroused and ready. His cock head pressed against my opening, and a few kisses later, he thrust in, slowly but firmly. I don't remember there being pain, just a sense of overwhelming relief and smugness that I was having my first time with someone I actually loved.

Well, he was just getting started. That boy fucked the living hell out of me. He was gentle at first, sure, but it didn't take long before I was clawing him to get him to go harder and faster. I loved my first time so much I insisted we try it a few more times that night.

It wasn't made to last. We split up eventually, I moved away, we lost touch. I wonder where he is, sometimes, but he's not on Facebook so I'll never know. But he'll always be special, and I'll always love him for making my first time memorable.

Female • 16 years old • Israel

We became friends right from the start. We found that we had the same cynical and sexual sense of humor.

Female • 22 years old • New England

"I can't tell you how glad I am that I never signed that 'True Love Waits' pledge."

Male • 15 years old • Washington DC

"I had never planned to lose my virginity to a guy—let alone Rob. I planned to pretend to be straight for as long as possible."