I was always a pretentious kid, so in a way 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 16 I knew 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 older 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 anything more, especially as 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, as it was the days before everyone had internet or mobile phones, we constantly wrote letters to each other. He had a penchant for the dramatic, writing on luxury paper with calligraphy pens and sealing them with wax stamped with his own, personalized seal. It was all stupidly romantic, with us discussing worldly concepts and our plans to change the world. 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 soul mate, 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 after 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, and so was refreshingly upfront about my excitement. Our first kiss was deep, and sweet, tinged with sexual desire without being overwhelmingly lustful. 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’d retort, 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 or 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 behaviour 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 and nipping at him to get him to go harder and faster. We broke the headboard off his bed, which made for amusing discussion with his parents later. And I loved my first time so much I insisted we try it a few more times that night. He taught me how to ask for what I wanted, and that my pleasure was important and valuable.
I knew I was kinky even back then, and it wasn’t long before I tried to get our play a bit darker. Jesse was the one who eroticised vampires for me, having bought these metal fangs that scarred me in a delicious way for life. But I remember trying to get him to experiment with spanking, and how hurt I was that he couldn’t stop laughing at how silly it was. Soon our sex devolved to that ultimate low- in front of the TV while halfheartedly watching VIP or the Knife Show. It was downhill from there, if you can imagine a downhill from there.
I remember that relationship being my first real lesson in classism. His parents worried about our relationship because they were certain I wanted to get pregnant and claim some of their fortune. I, meanwhile, was one of those kids who didn’t even want to babysit kids under the age of 6, so this was a ridiculous fear, but there you go- that’s classism at work. It was as hard for them to imagine I was happy living my gutterpunk life as it was for me to imagine justifying shopping at Dolce and Gabbana. Later I would get angry at Jesse for whining about his lack of a vintage car while I struggled to make food from the food bank last for the week. Mine was a world he would never really know.
So, it wasn’t made to last. We split up eventually, I moved away, we lost touch. My cat, romantic as always, peed on his love letters in protest. I wonder where he is, sometimes, but he’s not on Facebook so I’ll never know. But Jesse will always be special, and I’ll always love him for making my first time memorable. He taught me so much about loving my body and being an active participant in my own sexuality. But thank god, in a way, that we lost touch- if he thought spanking was weird, he would be shocked at my life now, a whirl of kink and clowns and sex work and sex parties. I've found him online, or traces of him, so at least I know he's alive.
I hope he’s happy now, wherever he is.