5 Trans Women Discuss Losing Their Virginity—Twice

Josie is a 29-year-old trans woman from South Carolina. She told Broadly that when she lived as a straight man in her youth, she expected more from losing her virginity: “I thought it was this magical thing, but it ended up to just be sex.”

The “magic” came after she transitioned. “I lost my virginity for the second time when I was visiting a friend from a Facebook group,” she said. “I drove four hours to her house to hang out. I was only a few months into hormone replacement therapy and was more excited then you can imagine.” Josie was also nervous: “When she touched me, my knees became weak,” Josie told me. “We ended up in her bed.”

Josie’s partner was another trans woman. “She worked very slowly and made 100 percent sure that I was okay with the process of being penetrated for the first time.” Though Josie had had sex before transitioning, this experience was different: in the changes in her body and identity; how sex acts felt; the emotions of being with another person in bed.

“When she penetrated me, it was a little painful, but I became putty,” Josie told me. “My defenses fell, and I truly felt like I’d entered a new stage of my life. In my heart, I felt that this destroyed the mask I wore for so long.”

Kate is a 39-year-old teacher in New York City. She has been attracted to women all her life. She first had sex “a long time ago,” with a woman to whom she would, decades later, come out to as transgender. When I asked her if she felt like she “became a virgin again” after she transitioned, Kate said, “Kind of: It felt like starting over. I said things to my friends like, ‘I've never kissed anyone before.’ A part of me knew that this was a big beginning.” The concept of being revirginized remains “silly” to her: “I feel the same way about virgin as damsel or maiden: These words are used to demean and infantilize women.”

Kate hasn’t had penetrative sex post-transition. “I've decided not to use my penis, which is still on my body, unless someone asks me to. My current partner says she doesn't ‘feel like she needs’ my penis.” She met her partner on Tinder. “She's never dated a trans person, and is treating me like I am not trans,” Kate said, adding that that’s how she prefers things. “She texted me today: ‘I…100 percent agree about exploring our femininity together. Pretty girls forever.’ There is a ton of physical chemistry, political agreement, and joint healing, bonding, and growing. I couldn't have met a better person to be my first physical partner after my transition.”

Robin is a bisexual trans woman in her late 30s. “I first had sex in 2001, at age 21,” she said. “It was awkward, but I don't think more awkward than most people's first time. I spent another 13 years having sex following that before I realized I was trans.” She wasn’t interested in penetrative sex, but performed that role in bed for the pleasure of the women she slept with. “I preferred receiving oral sex, but it took a long time to connect that preference with my dysphoria. I thought of myself as a lousy dude, never as a woman. I had a lot of shame, but I managed to function despite it,” she said.

When she underwent bottom surgery, sex felt new. “I definitely referred to having a new kind of virginity once I had a vagina,” she said. “I went about losing that virginity as soon as I was healed enough.”

She had sex with her wife following the procedure, but that was deeply personal to their relationship; it didn’t feel like she’d had sex for the first time “twice,” per se. “However, I put a lot of thought into the first time I received vaginal penetrative sex with someone after surgery,” Robin says. “I picked a sweet, generally straight, cisgender boy,” she said. “He was very understanding and patient, although he'd had no previous experience with trans women,” Robin says. The neo-vagina can be extremely tight following the procedure to create it, requiring months of dilation to expand. “Unfortunately, I was still very tight, and it didn't go well. Given the circumstances, I was grateful for his attentions, even if it didn't work out exactly as I'd hoped.”

Robin says her second first time was “more awkward than the first time I lost my virginity—I was worried I'd never be able to be penetrated comfortably. Happily, I was wrong. Over time, it's become easier, and I've gotten over the awkwardness of that first attempt,” she said.

“I've lost all kinds of virginities over the years,” Robin said. “There are always things I've never done before. I love doing something new and exciting for the first time.” She says the concept of virginity isn’t entirely applicable: “I don't think there's any clear lines of ‘virgin/not virgin.’ There's just stuff I've gotten more comfortable with.”

For Hannah, a 33-year-old trans woman in the Northeast, sex pre-transition wasn’t a positive experience. She is bisexual and pansexual, but at the time she was primarily interested in women. “Sex was a non-starter in high school. No shortage of girls told me to my face I was ‘too short,’ at 5’4”, to be their boyfriend.” She knew she was a woman, but rejection was painful. Throughout college, Hannah had plenty of opportunities to have sex, but she “turned them down mostly out of fear.” Eventually, she lost her virginity with a woman who was also a virgin.

“I came out to her as trans. To my astonishment, she took it in stride and offered to help me find people to talk to about it,” Hannah said. “She saw me dressed as a woman on multiple occasions, and I think she was more attracted to me when I was being authentic to myself. It was tremendously empowering. But I blew it.”

Hannah’s partner experienced pain during penetrative sex. “I had heard this is not uncommon when a girl loses her virginity, but it persisted. I wanted to explore sex, but she wasn’t as eager.” They ended up parting ways because of it.

After Hannah transitioned, she “did and didn’t” consider herself a virgin again. “When I had [bottom] surgery, I was dating a trans boy, and he was open to sex with me even before surgery. I asked a friend if you could lose your virginity to a strap-on. She said, ‘Virginity is a construct.’ I asked if you could deconstruct it with a 12” bright blue silicone dildo.”

Hannah has had “debilitating” complications following surgery, so her post-transition sexual experiences haven’t been as rewarding as some other trans women report. “I was confident the upcoming revision would fix the complications, but after the second [surgery], sex simply dropped off the table because it made things worse. I am simply not comfortable exposing myself to a partner,” Hannah said, shedding light on the complicated and difficult medical realities that trans people are sometimes forced to navigate.

“One of the most embarrassing experiences was after a date that went well. He found out about my medical situation and broke things off because he ‘didn’t want to wait’ for me to sort it out. It’s poetic justice, after I ended things with the girl I lost my virginity with for not so different a reason.” Hannah is in a relationship today, but describes herself as primarily asexual: “I feel like my sexuality has been taken from me by surgery.”

Jessica is a trans woman in her 40s on the East Coast involved in policy research. Before she transitioned, she was essentially straight. Today she is “somewhere between lesbian and queer.” The relationships that Jessica had when she was living as a man weren’t strictly heteronormative, though: “After I came out to my longtime partner, she wasn’t super surprised; she said I never really had that ‘guy energy,’ sexually.”

“After gender confirmation surgery,” Jessica said, sex was “very different in terms of how to have intercourse,” and “fundamentally changed my relationship with orgasms and masturbation.” At the end of the lay, it was still just sex, though it felt slightly more complex at first: “Sex with a bio-penis—yours or your partner’s—is so much simpler. Post-surgery, you have to find the right angles. And toys that are shaped right. And have the right flexibility and hardness. And properly positioned hips to get the entry angle right. And the right lube for your toys. And. And. And… Or, you can decide that the penetrative stuff isn’t necessary to get to the Big-O Ranch, and just eat each other out.”

She met her current partner six months prior to having bottom surgery four years ago. “I was her first transgender partner, but she realized she was a lesbian in her late 20s, so she’d been with men before, too—we both regarded a penis as a slightly more comfortable, convenient strap-on. We worked with what I had and got where we needed to with it.”

“I don’t put a ton of stock in ‘virginity,’” Jessica said. “After surgery, did I lose it when my partner went down on me? Or when I dilated for the first time? What about when she fucked me with a strap-on? My current partner and I are poly, so I’ve had sex with a trans woman who hasn’t had bottom surgery. So, does it only count if it’s bio-cock? I think you get to define it as whatever you like.

I didn’t lose my virginity twice. I just got to start having sex in a totally different way.”