I lost my virginity eight years after the first time I had consensual intercourse.
I know this flies in the face of everything we learn about the meaning of virginity. It’s not supposed to be a lizard’s tail, regenerating once it’s gone. But the real world doesn’t always fit into neatly defined boxes. Our lives and experiences don’t always follow the rules.
I grew up in Appalachia in a double-wide trailer in the woods surrounded by farmland. My childhood was, for the most part, unremarkable. My father worked long hours doing hard physical labor. My mother was a part-time beautician and full-time mother of three. My brothers and I spent the days exploring our vast deciduous playground. I would come inside after a long day of hard play, bruised and scraped and dirty. Looking back, I suppose I could call myself a tomboy. But in those days I was just a little boy, no “tom” needed.
I knew from an early age that I was somehow different from all the other little boys. I liked my hair long. I colored my fingernails with markers, which the teacher always made me wash off. I played the flute, loved to bake and sew, and preferred cats over dogs—things that shouldn’t be gendered but are in small towns across America. My nightly prayers always included a plea to God that I would wake up a girl.
I rarely had any interest in school yard romance. When I did it was because I thought I was supposed to, not because I really wanted to. As my classmates and I grew older, shows of romantic longing seemed to become compulsory. And as high school approached it became very clear that if I didn’t show interest in finding a girlfriend, something was wrong with me. I knew I wasn’t like my peers but I tried my best to keep them from seeing that. I found a date to my eighth grade promotion dance, held in our school cafeteria. I played the part. I gave my date a wrist corsage, walked into the dance with linked arms, slow-danced to the best country music of the late 1990s. I kept my hands well above my date’s hips and danced just close enough to her not to arouse any suspicion that I didn’t really want to be there. But it felt all wrong.
Then came high school. Suddenly most of the other boys were participating in a race to have sex. I found a girlfriend and convinced myself that I loved her. We spent long hours on the marching band bus holding hands, cuddling close. Eventually that led to making out on the dark trips home, hiding our heads from the chaperones as best we could. We progressed to awkward groping, exploring each other’s bodies under the cover of a Marching Warriors blanket. Our relationship lasted the length of my sophomore marching band season before we broke up. She claimed that she wasn’t ready to have a boyfriend and that we were moving too fast. I pretended to be heartbroken but in reality felt relief.
Our breakup lasted until the next fall. After a long trip home from a football game, we decided that it was time to finally take the plunge. We parked behind an isolated church, got into the backseat, and immediately we fell into each other. We ripped off our clothes, kissed each other deeply, and before I could process what was really happening, we were each having our very first penetrative sex. It was sweaty and awkward. Kenny Chesney was crooning on the radio. It felt fantastic in the tactile sense but I was emotionally detached from the experience. After we finished, we got dressed, and she drove me home in complete silence. She transferred to another school a couple of months later, and we never spoke again.
Everyone at my school seemed to suspect that I was queer. Even after word broke that I’d actually had heterosexual sex, people knew I wasn’t straight. I got teased and bullied by the other kids, mostly by the athletic and popular types. One boy in particular—a pudgy, acne-riddled member of one of the less successful sports teams—was relentless. I did my best to avoid interacting with him, yet somehow my very existence was enough for him to seek me out. If I was going to be queer, then he wouldn’t let me be happy.
But then, one spring evening as I was leaving a late jazz band practice, he approached me in the boys’ room. As he slowly moved close to me with balled fists, I thought I was about to get the beating of a lifetime. I started shaking, and just as I started to cry, he kissed me. It wasn’t a romantic kiss. It was barely even a lustful kiss. But finally, after years of simultaneous denial and hope for a moment like this, it was happening.
Neither of us spoke a word as we went into the farthest stall from the door. With only spit and the lubricant from his condom fighting the friction, he thrust himself into me. The pain was immediate and intense. I didn’t think sex was supposed to feel like this but I had limited knowledge of the mechanics of anal sex. Maybe it was supposed to hurt the first time. I’d always heard that was true for a girl’s first time being penetrated so why would it be different for me? I found it difficult to stay quiet enough not to get caught but that proved irrelevant because it was over almost as quickly as it began.
For the second time, I thought I had really lost my virginity.
For the second time, I feigned joy, all the while feeling detached.
Over the next several years, I had sexual encounters with a number of folks, both male and female. Accepting my queerness made my sex life better but something still felt wrong. I went away to college, and on a small liberal arts campus far from home, I found the language to understand what was so different about me. I learned that transgender people really do exist, and not just as drag queens or fetishistic transvestites paraded on the trashy daytime television shows. In this brand-new world, I learned that even though my birth certificate says male, I didn’t have to be someone I’m not.
I came out as trans during my first semester on campus. As my understanding of myself grew and my identity evolved, I found myself in a community that embraced me for who I was. When my friends’ parents would meet me and later ask whether I was a man or a woman, my friends often replied Does it really matter? or That’s Alex Meeks.
But while my social circle began to recognize me as feminine or transcending gender, some things still weren’t right. I felt like partners were having sex with me as they would with a man and I was not bringing my true identity into the bedroom. I only knew how to have sex like a man. I didn’t know how to view my genitalia as anything other than masculine. Even when I slept with chasers, people who fetishize trans bodies and experiences, I still felt that I was being viewed sexually as a man. I felt doomed to eternal disconnection from my body, emotionally absent as I experienced physical intimacy and pleasure.
But then, two years after I graduated from college, I met Drew. My roommate and a friend visiting from out of town were at a dive bar in the small town where I lived, and they invited me to join them. We were enjoying cheap beer and stimulating conversation when this beautiful man walked right over to our table and sat down across from me. Until my roommate introduced us, I hadn’t realized our friend had brought a roommate along for the trip. Drew was the kind of attractive that made it hard for me to speak. We talked about the mundane sorts of things people discuss while hanging out at a dive bar, but whenever our eyes met, we held each other’s gaze ever-so-slightly longer than normal in a friendly interaction. He reached his leg out under the table and slowly began massaging my foot with his.
Our small group walked from the bar to a diner down the street and he reached for my hand and innocently held it, throwing the occasional smirk and a wink. At the diner, we continued our game of footsie. Mundane conversations evolved into more personal dialogue as we discussed the intricacies and nuance of queer sexualities. I was surprised when Drew revealed that he was also trans while discussing how our sexualities evolve as we grow and change as people. I felt a brief moment of jealousy. Although I had been living as a woman in many facets of my life for years, nobody was ever surprised to learn that my gender identity differed from what I was assigned at birth.
After we ate, four of us went back to my shoebox of a basement apartment—Drew, his roommate, my roommate, and me. We piled on the pullout bed in the living room, drinking beers and watching cartoons. Before I really knew what was happening, Drew kissed me. Our roommates kissed. After a few minutes, they went elsewhere.
I felt more nervous than I ever had before. I had been out as trans for years but I still hadn’t had any sexual or romantic encounters with another trans person. And there I was on the sofa bed in my living room with the most attractive man I had ever met, a man who happened to also be trans. We undressed each other slowly and deliberately. Drew held me gently but securely. As he took my nipple into his mouth, waves of joy pulsed throughout every inch of my body. In all my experiences I had never felt anything quite like that. He took control in a way that was not dominant but confident and comforting.
We spent the next several hours exploring each other’s bodies, affirming our own identities. Every time we touched, I felt the masculine leave my body, a wrong being righted. He climbed on top of me, gently kissing my neck and telling me how beautiful I was. With his weight on top of me, I felt my body transform from linebacker to ballerina. He held me closely as we rolled around the bed, unable to distinguish up from down as two people passionately became one.
If a stranger had seen us having sex, their description would be almost unrecognizable to us. An outside observer would say that I penetrated Drew, that I was the man and he was the woman.
But nothing could have been farther from the truth.
It felt as though our genitals had switched places. I felt like he was entering my body. For one brief night, I felt that the errors made in my mother’s womb had been corrected. I had known intellectually that my womanhood could exist and be powerful regardless of what I had between my legs, but for the first time in my life, I truly felt that I was really a woman.
The next day we all went out for lunch at a nearby Tex-Mex restaurant. Drew and I sat next to each other, holding hands as we ate. After lunch, my roommate and I walked our guests back to their car. Drew kissed me and held me in an embrace that felt as though it would never end and then he and his roommate began their two-hour drive home. I hoped we would see each other again, but that was not meant to be. A few months later, we both moved to different cities a continent apart from each other.
Drew and I haven’t spoken in almost four years, but few days go by where I do not think of him and of the beautiful night we shared. A girl never forgets the time she lost her virginity, even if that experience defies the definition as we know it.