It was eleven o’clock on a Saturday night. While my friends were busy at their usual routine of smoking pot and watching Bob’s Burgers in Harlem, I was sober in Brooklyn, stripped down to my underwear, and straddling Persephone*, who, upon her demand, was tied to her bed with velcro restraints.
“I feel so vulnerable,” she said softly.
“Is that a good thing?” I hesitantly asked. I wasn’t yet at a point where I could let myself feel vulnerable during sex. And to be honest, it made me uncomfortable that Persephone felt the need to share this sentiment so bluntly. Or at all. She affirmed that yes, to her, feeling vulnerable was in fact good.
Persephone and I had met the month before, at a mutual friend’s Winter Solstice party. As the night progressed, we discovered that we knew many of the same people, shared a few interests, and most importantly, that we were both single and non-monogamous. By the end of the night, fueled by cheap alcohol and raging hormones, we were making out on the floor in the midst of the beginning of a three-way between our other friends who were there. Since that night, Persephone and I began to talk to each other every day, sending each other flirtatious text messages, suggestive photos, and pornographic descriptions of what we would like to do to each other. Persephone wasn’t bothered by the fact that I wasn’t looking for anything serious. I wasn’t bothered by the fact that she was a transwoman, or by the fact that at twenty-four, she was five years older than I was.
The first time we had sex was after I had returned to New York after winter break. We watched an episode of Breaking Bad and then she disappeared into her bedroom for a few minutes. When she called me in, I saw that she had changed into some hyper-feminine, lacy, satiny lingerie, complete with thigh-high stockings and a garter belt. She pulled me on top of her on the bed, crushing our lips together. She moved my hand down to her stockings.
“Take these off of me,” she whispered, “Don’t tear them; they’re expensive.” I stared down at the material and fumbled with what I saw as a complicated configuration of buttons and snaps and thin, tearable material. She recognized my inexperience pretty quickly and undid them herself, rolling her eyes and laughing. I felt like a sixteen-year-old unhooking their girlfriend’s bra for the first time. After she pulled her stockings off, she instructed me to tie her down and fuck her.
From that night forward, Persephone and I began a sort of casual sexual relationship that lasted a grand total of two months. To this day, I regret allowing the affair to have gone on past the first two times we slept together. Everything just felt wrong about it, and during that time, I did everything in my power to justify my decisions to myself. I didn’t feel safe walking by myself in her neighborhood at night, but I told myself I was just paranoid, and besides, I carried around pepper spray. I didn’t feel comfortable using restraints on her, but I thought that since I wasn’t the one being tied down, my comfort levels didn’t matter.
She suffered from depression and had frequent panic attacks, but since she always called upon me to help her through them, it was somehow my responsibility to take care of her, even though I was going through my own mental issues and was really not qualified to help anyone else. And to be completely and brutally honest, I just wasn’t attracted to her at all. She was about a foot taller than me and she was clingier and needier than I could handle. But in my mind, newly full of queer theory essays, feminist papers, and transgender narratives, combined with my recent acknowledgement of my own trans identity of a non-binary, androgynous dyke, I was sure that if I refused to have sex with Persephone, I would be perpetuating transmisogyny (which I now realize is ridiculous).
And besides, there were some good things about her. When we had sex, she would exclusively use male terms when speaking to me, like saying I was a “pretty boy,” telling me how hot I looked when I bound my chest and wore tight boxer briefs, and calling my vagina a cock. Since I had made the decision not to medically or socially transition from female to male, it was empowering to be seen as a guy, at least for one night. And, as we all know, empowerment makes you feel sexy as hell.
One night when we were starting to have sex, she fastened a dog collar around her neck. Before I could ask if she could maybe, possibly consider not degrading herself that night, she reached into her box of sex toys and pulled out a pink, anatomically correct dildo. She pressed it into my hand.
“Tie me up and put this in my mouth,” she demanded. I was speechless for a moment.
“Oh,” I said slowly, “Okay…”
I started off slowly, just barely slipping the tip into her mouth and rubbing her between her legs. She kept on moving her head up and violently sucking the dildo while I kept pulling it back, freaked out by the gagging sounds she was making.
“Stop pulling it away,” she whined.
“I don’t want to choke you!” I said, giggling nervously. Honestly, the last thing I needed in my life was to accidentally kill the woman I was sleeping with. Oh, sorry, Officer, I didn’t mean to kill her; she wanted to fellate a pink, silicone phallus, I swear!
Persephone looked at me like I was an idiot.
“I want you to choke me.”
“Oh…um…I’m not…” I trailed off. Where was I going with this? I’m not comfortable with this? I’m not into the same kinks you’re into? I’m really not that into you, but I’m afraid you’ll hurt yourself if I end up being yet another person who has rejected you?
“It’s fine,” she sighed, “Just put it back in the box.”
I did what I was told and resumed what I was doing, sans dildo.
“Yeah, just like that,” she encouraged. I started to bite her neck and breasts. “Gonna make me bleed?” God, I hoped not. “Oh, yeah, fill me up.” Where? And with what? I really hoped she wasn’t about to ask me to put anything in her ass. I was so not prepared to go there.
After about ten minutes of this, I thought the one thing that you should never think during sex: Can you just orgasm so I can go home?
And that’s the moment I realized that tonight needed to be the last time I hooked up with Persephone. Being liked and sought after was nice, but it just didn’t seem worth it anymore, especially when her mental issues and the fact that she seemed to want me to be her caretaker factored into the equation. We broke things off a few weeks later, after I repeatedly told her I needed space, and after she repeatedly contacted me every other day anyway. She accused me of mistreating her because I wasn’t being emotionally intimate with her, and left me sitting on a park bench. I never saw her again, but she did send me a Facebook message during Pride weekend that year apologizing for her actions. I never responded.
Even though I regret the whole affair, I must admit that I learned a few valuable life lessons from it: if you’re engaging in any sort of sexual act, especially if it involves kink, both parties need to be into it. Just because you’re a top, doesn’t mean your feelings don’t matter, and always trust your instinct and stop something if it doesn’t feel right. They teach us that in elementary school, but somehow that lesson tends to get lost in the recesses of our minds when sex starts entering into our lives.
I wouldn’t say I would go back in time and stop this from happening if I could. I mean, if nothing else, it’s something to write about.
*Name has been changed.
C. Harper Gold is a student and writer in New York City. You can find more of her writing at charpergold.wordpress.com.