Illustration By Lia Kantrowitz

Having Sex With Straight Men and Learning to Love as a Transgender Woman

As a teenage boy, and later a woman, I saw men try, fail, and finally succeed at learning to love.

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Aug 14 2018, 7:44pm

Illustration By Lia Kantrowitz

First-time sexual experiences are notoriously awkward. This can be especially true for trans people before or after transition: When sex is entwined with gender and directly involves a body you want to change, even a positive encounter can leave a trans person feeling wanted for all the wrong reasons. When I was living as a boy, sex was terrible. In addition to being generally inconsequential and void of intimacy, the experiences I had with boys who saw me as one too made me feel invisible.

The few gay guys I knew as a teenager didn’t find me attractive. I was so feminine that they said things to me like, “I want a boyfriend, not a girlfriend,” denouncing my gender expression as undesirable and antithetical to gay male sexuality. Fine. I was always attracted to straight guys anyway, who always showed me more sexual interest than gay guys did, even when I lived as a boy.

At high school parties, straight boys looked into my eyes and let their hands linger on my waist. Flirtatious comments were common—as were the canceled or changed plans that followed them. (A guy would tell me I was cute and schedule a movie date, only to bring along a mutual friend at the last minute.) This flurry of mixed messages had me chasing leads that I could never be certain were really there. Those boys didn’t see me as a girl, but I was a teenage crossdresser—I was feminine, and they saw something in me that they liked. Maybe that I was a convenient object to explore and discard?

I’d lost my virginity to him. I thought it marked the start of something. Really, it marked an end.

I was mostly alone, trying to figure out who I had to be in order to be wanted, when I met my first love, a straight, curious guy from the opposite side of my home state. Brandon (his name has been changed) and I started talking on MySpace when I was 16. He was a year older, and smart, funny, fit in a cute way (he had a Bowflex), and alternative in a 2000s way (he wore bandanas around his neck, had “indie” hair, and was in a moped squad).

Watching me on our webcam dates, he told me I looked like a girl; he thought I was beautiful. Shouldn’t it have felt affirming? I think it did, but it also made me nervous and triggered my fear of being feminine. Even though I often wore women’s clothing, I was ashamed of my femininity because I thought it meant I’d have to be alone.

After a summer of webcam romance, Brandon drove a hundred miles to meet me. It was scary and exciting for both of us. When he came over, I felt like I was experiencing what my peers were: simple, sweaty teenage desire. We watched The Never Ending Story and stayed up until we couldn’t keep our eyes open. In the morning, we passed second base, hit third, but never went home. It was my first sexual experience, and as far as I was concerned, I’d lost my virginity to him. I thought it marked the start of something.

Really, it marked an end. After Brandon hugged me goodbye and drove home, we didn’t speak for months. I was too nervous to ask why. When I finally got the courage to reach out to him, Brandon was sincerely apologetic. He said that what we had had was real, but that I had caused him to realize he couldn’t be with a boy after all. I couldn’t comprehend it. Brandon had given me everything that I ever wanted, and then it disappeared as if nothing ever happened. After he told me that my gender was what kept us apart, I became even more confused than I had been before meeting him. Who was I supposed to be? I threw my feminine clothes away and tried to commit to living as a man. I performed for everyone else, desperate to experience young love without ever experiencing myself.

I lived in a fog for years, looking for someone who would see me in the way that I thought Brandon had. A few straight guys were curious enough to flirt with me, but none of it went further than that. I didn’t have a sexual experience again for years, and when I did, they were usually with strangers in bars. One guy made out with me at a party and we left together. On the subway, drunk, he told me not to tell anyone about it—it would be embarrassing to him. I agreed to be a secret.

All of that ended when I became a woman. It seems absurd to say that in a single sentence: The story of getting there is long and unlikely. Just know that, by my early 20s, circumstances aligned at a moment of true humility in my life, and it opened a gateway to a new life that I couldn’t have anticipated. Even though it terrified me, I went through that gateway.

On the other side, I met the person who has always loved and wanted me. I didn’t know what would happen when Diana took over my life, but she proved to be much better at everything. Where I was scared, she was fearless. Where I lacked confidence, she was proud. As my name changed, my breasts grew, and my hair fell long past my shoulders, Diana helped me to look at myself without wanting to destroy the person looking back. I was ready for others to see me, too.

I performed for everyone else, desperate to experience young love without ever experiencing myself.

My first year in transition was my first year dating—I was in my early 20s having experiences most people have in their teens. Finding a date wasn’t hard. I discovered that there are people in the world (a lot of people) who find people like me attractive. Transamorous men—usually straight guys who are into trans girls—treated me like a hot commodity when I made myself available on online dating platforms. Some were specifically looking for girls like me, and others were surprised to learn I was trans—and enthusiastically pursued me once they found out.

Sometime that year, I had sex. The first few guys I fooled around with were clear: They thought I was hot. Having sex as a woman made me feel attractive and desirable for the first time, which helped my self-esteem. Being feminine had always been a curse, but these men couldn’t get enough of it. They validated a part of me that had once been devastating, and it felt incredible to feel like I fit in.

Of course, there was another side to my experiences. I quickly learned what it meant to be sexually objectified. As a trans woman, this took shape in distinct ways. I met men who were hyper-confident, yet clearly felt shame for wanting me. Some wouldn’t look me in the eye; others looked straight through me. Two shoved their hands uncomfortably into my tight, high-waisted jeans when we kissed on the street. Some ignored my requests to meet in public, begging to go to my apartment instead.

One guy is seared in my memory. He was particularly hot: tall; fit; glowing skin. He had a high-powered job and was almost 30. After a back-and-forth about planning to meet me and my refusing to go straight to his apartment, he told me the truth: He couldn’t be seen with me unless he could first meet privately to determine if I passed well enough. It wasn’t personal, he said—he’d fuck me either way, but if I wanted more than sex, I had to look the part. He wasn’t a jerk, he wasn’t transphobic, he insisted. He just had a reputation and an important career to preserve. When I told him the date was off, he said, “Gay guys are so much more dramatic than real women.” How strange that after a lifetime of being told I was too feminine, now my problem was not being feminine enough.

These horny guys didn’t see the bigger part of me that is more important than gender or sex. They just wanted to break a taboo; to satisfy a secret fetish; to experience sex with someone they were too terrified to love. I was so starved for affection that I took this kind of intimacy for what it was. I didn’t resent these men—I had never known intimacy before, so their touch was still powerful.

Gay guys are so much more dramatic than real women.

Maybe other people were never the solution. After I satisfied my initial need to feel beautiful or desirable to men, I started to think about them less. As I grew into myself as a woman, I stopped seeking sex for sex’s sake. If I was going to get laid, it would be on my terms. I stopped traveling for dates, refused to have sex the first time I met someone, and indulged in personal time, taking myself to the movies or dinner. These little-seeming things represented a radical transformation: Before then, I had been unable to see meaning in myself outside of men’s approval.

As I have aged in transition, I have come to know countless men who are open about their attraction to women like me. I feel kindred to them because I was also a man once—I know how masculinity can be weaponized, compelling you to conform or else risk losing everything. The difference is that my truth lay beyond the male sex, and theirs lies within it. It was difficult to transition, but I had a pathway to follow. These men have no such direction. Transamorous men often have no community, no public representation, and no external incentive to upset the foundation of their lives by publicly expressing their desires. Many live with incredible anxiety and fear because of it. They may have treated me poorly, but I am free and they are trapped within the social mechanisms that once oppressed me for not being the right kind of man, too. (I’m not a man, but that view is not widely shared in American culture.)

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Some transamorous men have rescued themselves from the gendered social norms that don’t allow them to fully realize who they are. They are some of my favorite people. For whatever reason, they have been able to discard the burdens society puts on their desire, allowing their sexuality to develop more honestly. It isn’t twisted up by taboo, it hasn’t grown darker in the shadows—rather, it looks very much like the love shared between any two people who are confident and comfortable with themselves.

Sharing my bed with those men allowed us both to experience true intimacy. We have very different identities and life experiences, but a certain commonality brings us closer together: The obstacle between me and the sexual and romantic affection I yearned for was a rejection of myself; in hiding their desires, the men who could not value me were rejecting parts of themselves, too.

Love, if I know anything about it today, isn’t about being wanted by someone else. It’s about two people who are able to be honest with each other because they have both been courageous enough to reveal who they truly are, despite the cost.