Inside Out: Confessions of a 27-Year-Old Gay Virgin

Photo: Uwe Krejci/Corbis

I was 21 when I met Jacob. He was the sort of guy the 16-year-old closeted version of me had fantasized about — a brooding former model who was late enough into his twenties to be retired, had probably been mistaken for Brandon Boyd in 2002, and was confident enough to wave at me from across the bar. “Stay there,” he mouthed before walking to my corner. “I saw you and have to buy you a drink.” He actually bought me several before inviting me home, but I hesitantly declined.

Three days of texting later, I anxiously met him at his apartment all the way on Manhattan’s Avenue D, which a friend jokingly warned me stood for death, and told him it was my first time. My hands were literally shaking.

“I know,” he laughed and gripped my shoulder.

He played the Sea and Cake to ease my nerves while our clothes met the floor. I twirled a lock of his hair and ran a finger along his feet, intoxicated that I finally had access to another man’s body but unsure what to do. Pretty quickly, he got how far it was going to go, even though I didn’t say anything. He went down on me, but that didn’t work, so we tried finishing each other off with our hands. Eventually, we just finished ourselves.

He had warned me before that he never let guys spend the night, but that was the part I had wanted most. I had hoped he would make an exception, but he did not: I took a shower, alone, and left.

A few years later, I would joke with friends that I had jerked off half of Williamsburg, because this is how nearly all of my encounters went in my early twenties. Gay friends even warned guys who approached me at bars that I was Mormon, a lie that I got tired of correcting.

Actually, I was raised Pentecostal — think Jesus Camp on steroids — in California, but by the time I came to New York, my religious identity had evolved from homogenous Christianity to amorphous agnosticism, though my actions often said differently. For years, I held the sentiment that penetrative sex was the sacred line that separated men who liked men from officially being gay.

It was that knotty distinction that helped me exit the closet a year earlier in college: You can date guys so long as you don’t “know” them, in a biblical sense. Sex came after … domestic partnership? It was a complicated perspective for a repressed gay millennial. My female virgin friends at least had religion or traditional values or purity to hide behind when the issue of the Sex They Would Not Be Having came up — even if most guys weren’t patient with their prudish behavior in the bedroom.

Like theirs, my air of innocence regularly attracted guys. In my early twenties, I didn’t even have to tell suitors I was a virgin. Kid you not: Men and at least two women have used the line “I want to corrupt you” without me even saying anything. Since I was gay, though, straight people presumed otherwise. Once, a guy at a party told me he didn’t want to hear about “whatever weird sex” I was having — even though it was probably less advanced than the kind he had in junior high.

I discovered that status as one of these immaculate unicorns also came with a strange sense of power. It dramatically alters people’s perception of you. When you coyly reply “undecided” to your friend’s top or bottom inquiries, it’s shocking. Meanwhile, partners coddle you. They become overly sensitive and bore you, so you dump them. People dump you. People get scared you’re looking for something too serious, or become intrigued. Sometimes they get turned on after being turned off and you feel like you’ve won, because you’d never give it up to a guy like that. A lot of guys beg. And beg more. You’re accused of torture, which seems melodramatic. Maybe you are being manipulative, though. You notice over time this visible shift that inspires guilt. You see their physical hunger evolving into something emotional. They get desperate and then withdraw. Sometimes they get aggressive.

I met Russ last November at a gay party called Xanadude, one of those cavernous loft parties in Brooklyn that’s filled with black-lit torsos and remixed Pitchfork anthems. He was 27 and about six-foot-three like me, blond, and prone to smiling. We hit it off enough that I asked if he wanted to come to my apartment a few blocks away. When we got there, he threw me against the bed. He peeled off all my clothes before I could even touch his. I liked his decisiveness. Plus, he had the sort of almost-fit body that was sexy and disarming at the same time.

He quickly told me he was going to fuck me. When I said no, he thought it was a game of sorts.

“I don’t do that,” I said.

“What do you mean?”

“I just don’t. Actually, I’m a virgin.”

His eyes scanned my face.

“I don’t believe you.” He smirked. “You probably say that to every guy.”

I didn’t make a habit of telling hookups I was a virgin, because this was a common reaction when I did. Maybe it was his sweet Southern disposition, but I found myself giggling as he accused me of lying, even as his cock inched closer and closer to my ass, testing the waters. We wrestled for however long it takes both xx albums to play twice, him furiously trying to top me. He collapsed in laughter each time I overcame him. It unnerved me, but it was also the most exciting sorta-sex I had ever had. Someone else had surprised me for once.

Over the next two months we hooked up a few times a week. When things swung tender, he lost interest, so I indulged the dark turns these nights with Russ sometimes took. I questioned my interest in choke-play and eventually more cat-and-mouse rape-play until one night, a few hours before I was flying home for Christmas, when the rape-play stopped being playful. He entered me about three inches deep without a condom before I could throw him off my bed.

“I’ve just never waited this long for someone,” he lashed out while he was pulling on his jeans.

“Uh, so you’re going to turn … this … on me?” I asked. “Just get out.”

He texted me a few minutes later, this time blaming alcohol. I told him to never contact me again. He has not.

What he did was obviously dangerous emotionally and physically (I have been tested since and am fine). But I realized afterwards that sex had always felt threatening for another reason. It was just another thing I could use to control the distance between myself and others, even people I wasn’t physical with. With three words — I’m a virgin — I could surprise almost anyone. I could prove they didn’t know me. In the same way religion had for so many years, it felt safe but also lonely.

Like most late-in-life virgins, I was waiting for some superlative occasion — the perfect encounter with someone with whom I shared feelings that approached love. About six months ago, I stopped obsessing over the perfect moment, and the sex I eventually did have trumped whatever it was I had imagined. It wasn’t prompted. It wasn’t meditated. It was just a regular Saturday night with a guy who was kind and adorable and special enough to be my boyfriend, but who just wasn’t “the One.” It still was ideal, an exercise in my own impotence to control circumstance. And don’t get me wrong: It was hot. I’ll remember it as such even though we broke up three months ago.

It wasn’t just being inside someone and having someone inside of me that was so gratifying. I realized that I was with the majority for once. I had grown up gay in an especially loathing environment. After years of feeling like an outsider, I had marginalized myself by avoiding the most celebrated act of intimacy. I had retreated to the fringe. And that was what was powerful about that night: being on the inside for once.

Names, including the author’s, have been changed.

Confessions of a 27-Year-Old Gay Virgin