How Internalized Shame Influenced the Choice of My First Sex Partner and Led Me to Cheat on the Boyfriend I Really Liked by Fiona Helmsley

My freshman year of high school I had two goals: to try LSD* and to lose my virginity. I accomplished both by the end of first marking period.

Though I had a boyfriend at the time who was also a virgin, my first time was not with him. It was with his best friend, a sixteen year old mimbo extraordinaire who spelled the “I” sound in his name with a “Y,” making “Chris” Chrys. I choose Chrys specifically because he was promiscuous and aggressive. My boyfriend, whom I liked very much, was just too chivalrous and respectful towards me, which left the physical aspects of our relationship stalled because of my own sexual hang-ups. I needed a first time partner who would not just storyboard the event for me, but feed me his penis like a director might feed a bad actor their lines.

Chrys and I had had a previous sexual encounter when it hadn’t been cheating on my part and bro foul on his, the summer before I hit the hallways as a freshman.

One night I snuck out of the house with my friend Louise and Chrys was one of the boys we happened to meet out on the street after midnight. While Louise got it on with his friend, I laid down in the grass and let Chrys have most of his way with my basically comatose form. I wasn’t drunk or on drugs, it was the shame I felt that completely mired my ability for both response and reach around. Chrys had to release his own member and put it into my hands, because to take the initiative and open up his pants on my own would be to show that I wanted it, which I wouldn’t, even though I very much did.

From a very early age I had been sexually paralyzed by the notion that it was bad form for a female to show she wanted anything sexually, and even worse for her to go out and seek it. I had grown up in an Irish-Catholic family, and even though for a short period of time my parents had hidden a copy of Our Bodies, Ourselves under the mattress in their bedroom, there was zero dialogue in our house about the subject matters in its pages. Everything I learned about my body and sex I had to scavenge for myself. Though we never spoke about the “S” word, there was a strong, fragrant undercurrent to the silence. We weren’t talking about sex because it was a dirty, shameful thing.

My teenage years found me incredibly curious about sex, but the shame I had internalized shaped all of my sexual interactions. I was not prude per se but more frozen into frigidity. All of my sexual fantasies involved aggression on the part of my partners (envision Mickey Dolenz from the Monkees as a rapist) to resolve my own desirous culpability. It was my partners who were the ones in control, shaping events; I was just a passive entity. Even in my inner-most thoughts I wouldn’t allow myself be shown as an willing participant.

So freshman year- I liked my boyfriend, but he was just too respectful. He didn’t push me. He didn’t put my hands into his pants like Chrys did; he didn’t offer instructions or storyboards. He was holding me back by not taking the reins, by not making me do what he didn’t even know I wanted to. The night I’d fooled around with Chrys in the grass he’d asked me to have sex with him and though I’d said no, I always remembered the offer and we became closer as I dated his best friend. And one warm fall evening, 24 hours after my sweet, gentle boyfriend serenaded me outside my bedroom window with songs he learned starring in our high school’s production of How To Succeed In Business Without Really Trying, I agreed to meet Chrys in my backyard and had sex with him in the dirt pit behind my house.

It was very quick and it didn’t hurt. I was expecting it to as my only other close friend who had had sex had ended up in hospital with cysts on her ovaries, locker folklore at the time connecting the cysts to her too early middle school forays into fornication. Though I didn’t think sex would give me tumors, I assumed there would be some kind of strong physical discomfort. It was anticlimactic in all regards.

My first words to Chrys afterward were “Did I bleed?” He looked down at the prophylactic on his now flaccid penis and said “No.” I recall answering, “Must be all those horseback riding lessons I took.”

I hate to use words like give and take but I choose to give Chrys my virginity purposely, because I knew he would take it.

*Alas, LSD would let me down, too. I’d read Timothy Leary’s autobiography Flashbacks and had been heartened to learn about his experiments with psilocybin in the prisoner population. Leary had claimed success with using the drug to help recidivists come to terms with the personality defects that led them back to crime. Since adolescence is essentially one long ten year bid, I reached for LSD in the hope it might serve as a sort of psychedelic fix me in a time before Prozac. Maybe, my thought went, LSD would help me come to terms with what it was about myself that I loathed. Alas, it just made me even more tongue tied and awkward, and my taste in music and clothing suffered. I took it over 200 times, anyway, just to be sure.

Fiona Helmsley is a writer of creative non-fiction and poetry. Her first book There Are A Million Stories In The Naked City When You’re A Girl Who Gets Naked In The Naked City was released in 2010. Her writing can be found in various anthologies like How Dirty Girls Get Clean and Air In The Paragraph Line and online at websites like Jezebel and The Rumpus. She can be reached through her blog Flee Flee This Sad Hotel at