As part of our ongoing commitment to publishing stories by and about transgender and nonbinary people as well as by the cis people who love them, we bring you the following article by a cis woman about her personal experience. To read about a trans person’s experiences from the trans person's perspective, we’d like to point you to our cover story with Laverne Cox, our Q&A feature with memoirist Chris Edwards, this photo series about trans identity taken by trans photographer Amos Mac and this personal essay about dating pre- and post-transition by Shakina Nayfack. If you’re a trans person who has a story you want to share with our audience, we encourage you to pitch us at firstname.lastname@example.org.
When Hallie discovers her former flame is transitioning, she goes through some changes of her own.
The last time I saw my ex-boyfriend, she showed me her breasts. While still wearing her blue, scoop-neck shirt, Chrissy puffed out her chest and proudly declared, “I’ve got a B cup.” She looked so happy. I, however, felt a mix of confusing emotions. I’d dated Chris for over six years, and we’d lived together for five. During his life as a man, he’d gone on vacation with my family, met my high school friends, and followed me to Madison, Wisconsin. We were serious. So it was a blow to find out that my longest relationship had been with a man who had felt the whole time that he was really a woman. It was also a blow to discover that I wasn’t more relaxed about the whole thing. I write about sex for a living and have always considered myself super LGBTQ friendly. I should have been unconditionally accepting and happy for her. But I found myself wondering what this transition might say about me. I started playing our relationship back in my head, looking for signs that the Chris I knew loved me, that he was ever truly attracted to me.
While I couldn’t stop thinking about whether Chris had been faking his love for me, all everyone else wanted to know was if he had liked to dress in women’s underwear. I can’t count the number of times someone has probed, “Did you have any idea Chris wanted to be a woman?” It’s a difficult and painful thing to be asked. But I’m not the only ex-partner of a transgender woman who gets such questions. Caitlyn Jenner’s ex-wife Kris Jenner, and both of Caitlyn’s other ex-wives, get the same question constantly. It seems to be the only question anybody really cares about. And I always cringe when I hear journalists ask it, because I know how emotionally fraught it is to reply truthfully.
To answer honestly is to invite judgment. When I say I had an inkling of Chris’ preferences because he enjoyed dressing up as a woman occasionally, the next question invariably is, “Why did you stay in the relationship?” Or a joking, “Are you really a lesbian?” When people ask me things like this, what I actually hear is, “Just how in denial were you about your boyfriend’s gender? Just how in denial are you about your own sexual preferences? Were you so desperate for love and companionship that you pretended your partner was male?” I suppose I can’t really blame them, though, since these are questions I pose to myself all the time. Ultimately, what I knew, when I knew, and what it’s like to find out that your ex is transitioning is a conversation worth having—mixed emotions and all. By having these conversations, I’ve learned that it takes time to come to terms with the fact that you can be both happy for an ex discovering his or her true self, and totally freaked out.
"He showed me a photo of himself in his 20s, wearing a black lace dress and pearls, long auburn hair cascading past his broad shoulders, garish red lipstick, heavy eyeliner, head cocked, smiling seductively for the camera."
When I met Chris in graduate school in 2004 at The University of Texas-Austin, he was in his early 40s. He was a guitarist who’d toured with a variety of rock bands, and his long black hair, hoop earrings, and rope necklace made him more feminine than other men I’d dated, but only somewhat. A month after we started dating, he shyly revealed that he liked to dress in women’s clothes. I instantly felt closer to him because he had disclosed a possibly embarrassing secret. So I told him that when I was younger, I liked dressing as a man. “You were just playing around,” he said dismissively. Then he went to his closet, pulled out a tattered photo album, and flipped it open. He showed me a photo of himself in his 20s, wearing a black lace dress and pearls, long auburn hair cascading past his broad shoulders, garish red lipstick, heavy eyeliner, head cocked, smiling seductively for the camera. His gaze moved from the photo to me, as he carefully scanned my face for my reaction. I had no idea what to say. Emily Post had not addressed what to tell your anxious boyfriend when he reveals his transvestitism to you. After a long pause, I pulled out the most generic, non-offensive phrase I could think of.
“You look great,” I said, hoping my voice didn’t convey my uneasiness. He smiled.
“I did make a good-looking woman back then,” he said, pleased. Then he back-pedaled. “I mean, it was the ’80s, lots of rock stars looked like women anyway.”
“True,” I said. “David Bowie. Mick Jagger.” More pictures of his cross-dressing followed, most with a goth vibe, but then he flipped to one where he looked like a matronly woman heading off to a country club. I made a desperate attempt to fend off a rising giggle. But I failed, and laughter bubbled out of me.
“Why are you laughing?” he demanded, angrily.
“It’s just in this picture, you look like a housewife,” I said.
“You think I look like a clown!” he countered.
“No, no I don’t,” I insisted. He was upset, almost on the verge of tears. I reaffirmed that he looked great in the other photos, that this was just a bad outfit. But nothing I said diffused the situation. He was mad for hours. Perhaps I should’ve seen this as a sign that his transvestitism was more than a side interest. But we were in the beginning of our relationship; I was happy. I didn’t want it to end.
I asked him to dress up for me, hoping my request would prove that I accepted him. But he demurred. After baring his transvestite soul to me, Chris had backpedaled, apparently because I had laughed at that picture. I must have known on some level that his reticence was caused by something more than an offhanded laugh. But it was much harder in the moment to recognize Chris’ gender dysphoria
than it was years later, when the transition was underway.
That’s why, as I look back on our relationship, I only feel minor pangs of guilt for asking Chris to make changes in his physical appearance that were no doubt emotionally painful for him. I didn’t know the extent of his gender confusion and he seemed unwilling to admit his feelings to himself. I thought I was just being a typical grooming girlfriend when I asked him to cut his hair, stop wearing earrings, and remove his necklace. I asked him to change because it made him more attractive to me. Without realizing it, I was asking my boyfriend to make a gender transition. The haircut required the most cajoling. “I’m not attracted to guys with long hair,” I said, and he relented. I assumed that he wanted to keep his long hair because of his past as a rock musician. Maybe I should have seen his desire for long hair as a clue that he was transgender. But I was not just being willfully ignorant. Most cross-dressers are heterosexual and have no desire to live full time as another gender. I assumed that he fit into this category and thought of his cross-dressing as a quirky hobby, like collecting model trains. After the haircut, I opened my front door to see my boyfriend with his newly shorn locks. “You look great,” I said, hugging him.
“No, I don’t,” Chris whimpered. I pulled back and noticed that his jaw was clenched and tears were in his eyes. “I look like a businessman,” he repeated over and over, like an incantation.
“I can’t even look in the mirror,” he said, then burst into sobs. At the time, I thought he was just making me feel guilty for forcing him to look more conventional. But after watching Bruce Jenner’s special on Keeping Up with the Kardashians, I understood why Chris was so upset. On the special, Bruce explained that when his wife Kris had asked him to cut his hair, he felt like he was losing a key a part of his female identity. For Bruce, and I imagine for Chris, long hair was a way of holding on to femininity while still presenting as a man.
"That's when it hit me. My boyfriend had done this before. Not once, not a few times, but many, many times. It was unnerving."
Ironically, a few weeks after the haircut, I begged him to dress up in women’s clothes for me. I wanted to assure him that he could have his femininity, but only in secret. Inadvertently, I was driving him into the closet. But he told me he didn’t want to dress up, that it was too much work to Nair his entire body. He explained that he didn’t want to look like a man in woman’s clothes, but like an actual woman. That’s when I realized that his cross-dressing went deeper than just a sexual thrill. But I was afraid that if I acknowledged his gender dysphoria, the relationship would end.
After a few weeks of my begging him to cross-dress, he agreed, but only if I would wear a strap-on. I’d never pegged before, but I was game for anything, so it was a deal. We bought the cheap-est strap-on kit we could find, an industrial-sized bottle of Nair, and a container of baby powder. That’s when it hit me. My boyfriend had done this before. Not once, not a few times, but many, many times. It was unnerving.
Preparations began the night before. I left him alone at his apartment and waited at my house anxiously. Why should I be anxious? I asked myself. I’m a sex educator. I appreciate and support all forms of sexuality. On some level I knew, however, that acceptance of variety was not the same as a desire to be in a relationship with a person expressing it. Finally, I got the phone call. “I’m ready,” he said in a cheerful half-whisper.
I got in my Camry, telling myself that the situation was normal. I was just going to see my boyfriend. But as I tried to calm my mind, fear sweat started seeping out of me. Face. Armpits. Ass. When I knocked on his door with my damp knuckles, Chris greeted me looking more feminine than I ever had in my life. Blush, eyeliner, foundation, and crimson lipstick adorned his face. His hair was flat-ironed into a modified bob. The black lace cocktail dress he wore revealed legs covered in delicate fishnets, feet ensconced in black heels. I didn’t know what to do. Nothing could have prepared me for the first time I saw my boyfriend in full drag. I was scared to even smile, afraid he’d think that it was the beginning of a laugh. “Wow. Nice legs,” I sputtered to break the silence. Even though he looked good, I had no sexual attraction to him. I even had a tiny feeling of revulsion, which I pretended didn’t exist. I tried to mold my face into a normal expression.
“Thanks,” he said. I tried to think of something to say but my mind was spinning. Can I learn to be attracted to his cross-dressing? Does my absence of sexual desire mean I’m transphobic? Is my anxiety showing?
"Is he imagining that I’m a man? Is he a lesbian? What exactly is his sexual preference? What is mine?"
I didn’t know what to do. I couldn’t flee his apartment; he would be too hurt. I needed to appear enthusiastic. So I pulled him into the bedroom. Am I supposed to be the aggressor? I wondered. I decided that I should be, so I pushed him toward the bed, causing his dress to scoot up, revealing that his fish-nets were thigh-high and held up with garters, the clasps neatly fastened at the top. The skillful fastening of the garter clips gave me pause. Garter belts aren’t the type of thing that you can operate perfectly your first time. In fact, I’d never mastered them. Then I saw his red lace thong. I saw a small round bulge that could’ve easily been mistaken for a vulva. Where’s his penis? I wondered. How do you tuck a penis between your legs? Is there a YouTube video that shows you how? How many times has he tucked his penis?
I also realized he’d removed every strand of body hair with depilatory cream. Getting the strap-on harness out of my backpack, I wondered, Is he imagining that I’m a man? Is he a lesbian? What exactly is his sexual preference? What is mine? I was experiencing cognitive dissonance. He was my boyfriend. He loved me, or at least he said he did. Yet here he was, a she.
We kissed, and as I looked into his eyes, I wondered whether he wanted me to be turned on or to simply be appreciative of his transformation. I hoped that kissing him would make me feel more attracted to him. After all, I am bisexual, about a three on the Kinsey scale. But making out with a woman is one thing, and making out with your hairless boyfriend who’s tucked his penis between his legs is another.
During sex, I tried to ignore the feeling that something was wrong, pushing away the worry that I would never be turned on by Chris’ favorite sexual fantasy. But I felt like a hypocrite. I was a sex-positive woman who professed to be open to all forms of sexuality. Why couldn’t I get turned on by my boyfriend in high heels and garters? I’m pretty sure he could sense my lack of enthusiasm. And on some level, we both realized that we could never give each other what we wanted.
"Making out with a woman is one thing, and making out with your hairless boyfriend who's tucked his penis between his legs is another."ADVERTISEMENT
After we had sex, I wondered whether Chris was not just a cross-dresser, but rather, transgender. So a week later, I asked him: “Did you ever want to be a woman?” He said he did when he was younger, but in his 30s, he realized it had been a fantasy, not something he actually wanted to do. I wasn’t totally convinced.
Six months into our relationship, the cross-dressing tapered off, and happened only at my urging. Even though having sex with Chris while he was dressed as a woman didn’t turn me on, I knew that wearing women’s clothes was a part of who he was, so I tried to get him to dress up more. But he told me women’s clothes were losing their appeal. He blamed his age, saying a 42-year-old man with a beer belly didn’t look good in a dress. He also reminded me that I’d laughed at a picture of him. For the rest of our relationship, any time I asked him to dress up, he brought up my response to that one picture. I later realized that his obsession with my reaction was a proxy for the response he feared that his friends and family would have toward his female self.
I finally broke up with Chris after six years together. It wasn’t because of his cross-dressing; we just weren’t good for each other. But I began seeing a change in his appearance soon after I left. When he’d come over to visit my dog, his hair was long, the earrings were back in, the necklace was back on, and dark nail polish appeared on his fingers.
"Did he ever love me? Why did he date me? Am I really masculine?"
Years went by, and his changes became more dramatic. He grew his hair past his shoulders and dyed it blonde. He dressed as Uhura, the female communications officer from Star Trek, for Halloween, and posted a pic of himself on Facebook. His face seemed more feminized in photos. And in an appearance on a local newscast, he wore dangling earrings, a necklace, and a female scoop-neck shirt. The newscaster called him a “male researcher” to clarify for the audience.
A year after the news program (and four years after we had broken up), I learned why Chris’ appearance had been changing so dramatically. I’d been checking dating sites for years to see what he was up to. When we first broke up, I’d found him on Match.com in “men seeking women.” But this time, while perusing another site, I stumbled across “Chrissy” in the “trans” section. I was shocked. It’s one thing to speculate. It’s another thing to see it in front of your eyes. There was the man I’d lived with for years, wearing a black mesh shirt with a black bra underneath, puckering her red lips for her bathroom selfie. As I paged through picture after picture I was horrified but couldn’t look away. Did he ever love me? Why did he date me? Am I really masculine? I asked myself. How could I have spent so much of my adult life with someone who had wanted to be a woman the entire time? I also felt bad making Chrissy’s transition about me. So I reached out to her on Facebook and told her I was proud of her and would be there to support her. But I still couldn’t shake the feeling that this transition reflected poorly on me. Was I in denial about Chris’ gender identity? All evidence points to yes. But I wasn’t alone. Chris was in denial, too.
What type of woman gets into a relationship with a future trans-woman and stays for years, seemingly oblivious to the dysphoria of the partner she’s supposedly in love with? Until recently, I would’ve said a naïve woman who willfully ignored all the signs of gender confusion. But now my answer isn’t so simple. If I—a student of sexuality—was unaware that my partner was transgender, then how could I judge anybody else for having the same experience?
Few people know the whole story of their partners’ gender and sexuality. Even people in long-term heterosexual relationships have no idea about their partners’ sexual fantasies or infidelities. People hide all sorts of desires out of fear of rejection. But there is no “normal” sexual fantasy or gender identity, and that’s a good thing. If there’s anything that my relationship with Chrissy, or Caitlyn Jenner’s relationship with Kris can teach us, it’s this: being honest about your gender and sexuality may mean the end of a relationship. But quite often, it can also be the beginning of a much more fulfilling life—for everyone involved.
By Hallie Lieberman
Illustrated by Shannon Freshwater
This article originally appeared in the February/March print edition of BUST Magazine. Subscribe today!
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