My Grossest Sexual Encounter Was Also My Biggest Sexual Awakening

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I was still a virgin at 20, though I’d acquired a boyfriend just after I turned 19. I wasn’t religious, but from an early age, I’d been instilled—by society, schools, parents—with a deep sense of shame, especially when it came to my body and the things I did with it. Though I didn’t believe sex should be reserved for marriage, I did believe that it should be reserved for love. (I don’t anymore.)

In the year that we didn’t have sex, my boyfriend and I rarely discussed the topic. We rarely discussed any topics. On the other hand, my girlfriends—all of them older and deliriously more experienced—talked about it a great deal. They were mesmerized by the concept of a sophomore in college who was a virgin, but who had a boyfriend who was not a virgin.

During that year, my boyfriend once asked me, “How would you feel about seeing other people?” Totally caught off guard, I said, “I wouldn’t like it at all.” He nodded, pursed his lips, and never raised the topic again. What I didn’t realize was that this meant that he was going to start seeing other people. Very soon after asking, he did.

I found out about it from one of the girl’s friends, who was a senior and very glamorous, in part because she was international. When she told me, I felt sick to my stomach. Her announcement—which came publicly, over beers at an upperclassman’s party—felt both territorial and also well-intended: Apparently, up until that moment, everyone other than me had known about my boyfriend’s other girlfriend. I broke up with him. A few weeks later, he broke up with the other girl, and we started dating again. We didn’t talk about his infidelity, but we did start having sex.

Sex was a letdown. I’d found much more personal satisfaction in our earlier make-out sessions. Once, he asked me if I had any sexual fantasies. I said I’d always been intrigued by the idea of shower sex. He told me shower sex wasn’t actually sexy and definitely wasn’t convenient or easy. “Oh,” I said. “OK.” Then he asked me if I regretted having sex with him. I told him I didn’t, but that I did miss being a virgin. We’d been driving somewhere while we were having this conversation—two faces aimed at the windshield, two bodies headed in the same direction, two minds completely at odds. We didn’t talk about it again.

A couple of years into our relationship—by now we’d moved into an apartment together—he found a list on my computer titled “Ten Things I Plan to Steal From My Boyfriend When I Break Up With Him.” I assured him the list was a piece of fiction, a trifling little nothing I planned to submit to McSweeney’s. He pointed out that every item on the list—the fancy beach towels, the Wüsthof knife set, the marble salt box—was something he owned, and that it didn’t feel like fiction to him. I pointed out that the dog—No. 10 on the list—was something we both owned, and that fiction often drew from real life.

But the truth was that for the majority of the time we were together, I did want to break up with him. Every time he asked if I was happy, I lied and told him I was exquisitely so. I couldn’t tell him that sex was unsatisfying. I couldn’t tell him I was scared by the prospect of starting over, of meeting someone new, of having sex with another person. I couldn’t tell him I was unhappy. This went on for five years.

I’d like to say that I had some major epiphany when I turned 25, some self-realization that made me want to stop being embarrassed by the things I wanted, that made me want to stop privileging the feelings I projected onto my boyfriend over my own, that made me want to step up and start living my life in earnest as me qua me. There was no epiphany. Instead, there was phone sex.

It happened while I was walking my dog. I’d recently gotten into graduate school and moved out of state and out of the apartment I’d shared with my boyfriend. My plan had been to start telling the truth when I got to Charlottesville, where I hoped I’d magically find the nerve to finally break things off. But I’d been in town for almost two months, and I was still taking his calls, still making holiday plans with him as though I intended to keep them.

I got the phone-sex call on a night in October. My dog and I had been slowly wandering around the Downtown Mall. Bars were open. A ballgame was on. The weather was mild. People were everywhere.

“What are you doing?” my boyfriend asked when I answered the phone that night.

Instantly, I was annoyed. “Nothing.”

“Really?”

“Yeah,” I said. “I told you. I’m not doing anything.” In truth, I’d been admiring the storefront of a leather goods place, and my dog was pulling on his leash.

“Want to know what I’m doing?”

No, I didn’t want to know what he was doing. I wanted to know how to break up with someone, and I wanted a new leather purse that I couldn’t afford. I said, “Sure.”

“I’m lying in bed, and I’m thinking of you.”

“OK.”

“I’m thinking of you, and I’m getting hard.”

“Oh,” I said. And then, “Oh.”

“What are you thinking about?”

I looked at my dog, an adorably disproportioned Boston terrier with legs that were just a little too long for the breed and ears a little too large. He snorted up at me. I made a face like, Shh. Be quiet. We were still outside, still in public, but once again on the move, walking past bars and shops and crowds of good-looking people, some of whom I probably wanted to have sex with.

“Are you thinking about me?”

I cut down one of the alleys, where it was quieter.

“Sure,” I said, and I then experienced the same queasiness I’d known when I learned of his infidelity.

He moaned. My dog scratched at his collar.

“What’s that sound?” my boyfriend asked.

“What sound?”

I put my hand over the receiver.

My boyfriend moaned again. “Can you help me?” he asked.

Another woman in that moment might have been turned on by his vulnerability. I wasn’t. All I wanted was to get off the phone. All I wanted was to go back to my apartment, feed the dog, and then go for a drink with some new girlfriends from grad school. At the same time, I was grossly aware of the situation I’d gotten myself into. If I didn’t help him finish, I’d need to give him a reason. If I gave him the reason—that I’d been outside on a walk with our dog the whole time—he’d be embarrassed and possibly livid. I stepped farther down the alley, where I hoped no one would be able to hear me.

“Can you?” he asked again. “Help me?”

I closed my eyes in extreme discomfort. Then I said, “Does it feel good?”

I hated myself in that moment, hated how weak I was, how stupid, how out of sync with my own desires. I felt so guilty, so disgusted with myself—for giving in, obviously, but also for not wanting what he wanted. During that first year of our relationship, when he’d been aloof with his commitment and I’d been aloof with my body, I’d adored him. I’d desired him. I’d deferred, by instinct, to every one of his preferences. Now I had him, and he was mine. But in the five years we’d been together, I’d started to change, taking up hobbies and interests that were entirely my own: I joined several bowling leagues, ran marathons, wrote short stories. I’d also started looking at other men, whereas he’d started looking only at me. The devotion that I’d always imagined I’d wanted turned out to be a turnoff. This duality confused and disconcerted me. I experienced it as a personal—possibly even moral—failure, and so I didn’t talk about it with anyone—not him, not my sister, not my mother, not any of my new girlfriends from graduate school, many of whom were married. I wonder sometimes now what might have happened if I’d confided in one of those women, all of whom I admired. Would she have told me how common the experience is—of getting the man you’ve always wanted only to find your appetite almost immediately diminished? I’ll never know because—back then—I didn’t trust myself, and I didn’t trust other women.

“So good,” he said. “What about you?”

“Yep,” I said, barely audible.

“Are you touching yourself?”

“Yep.” My face was hot. My mouth was tight.

“Good,” he said, his voice noticeably a little higher. “Good.”

There was a sudden shudder on his end.

“I should go,” I said, still whispering, trying now to sound like a woman exhausted and spent by sex.

“I love you,” he said. I hung up.

Later that night, I met up with a few women from my program. I told them where I’d been and what I’d been doing. I didn’t express guilt, remorse, self-doubt, the confusion of being out of sync. I focused only on the comedy of the event: walking the dog while having phone sex. I behaved shamefully, mocking a man I’d once loved to a group of women I barely knew. And when I went home that night, I lay awake, sleepless, sweaty, sad. That trespass—of deriding my boyfriend behind his back—had a more profound effect on me than engaging in a quasi-sexual activity in which I wasn’t truly interested. A few weeks later, I leaned heavily on that memory—of having used my boyfriend as fodder for entertainment—when I finally ended things.

I’d like to say I became a new person after the breakup; that I transformed into a woman capable of speaking her mind openly and admitting her desires. I didn’t. Every day is a struggle to say aloud the things I want—out of a friendship, a brunch menu, a new pair of jeans. But I am trying. And if I make a blunder, that’s OK—it’s all me qua me from here.