“I’ll always remember the first time I had sex after [bottom surgery],” Rebecca Hammond tells me about halfway through our Skype chat. Hammond, a registered nurse and sex educator from Toronto whose short, asymmetrical haircut gives the impression of a bleach blonde Aeon Flux, speaks in a sleepy, seductive tone that almost verges on a purr; her words taking on an extra bit of vibration whenever she’s trying to emphasize her point.
It’s been 10 years since her procedure, and Hammond’s had a number of sexual experiences — good, bad, and somewhere in between — but that first experience of sex with a vagina is one that has stayed with her. “If I had to sum it up for myself, I’d say it just felt right,” she tells me. “There just wasn’t the tension there that there might have been beforehand.”
And yet, even as she fondly remembers that blissful feeling of congruity, that sense of intimacy in a body that felt “right,” she’s loath to give too much power to the idea that first-time sex is somehow transformative or earth-shattering. “[Virginity] is just a cultural idiom for speaking to innocence and loss,” she reminds me, and one with an uncomfortable, complicated history that doesn’t sit well with her.
As we chat, Hammond shifts between these two conflicting narratives of post-bottom surgery sex. On the one hand, she notes wryly, “You’re just putting stuff up your cunt,” an act that hardly seems worth a great deal of fuss and introspection (“I don’t get it!” she cries giddily, her voice rising a few octaves as she laughs). And yet she can’t shake the awareness that, even if “virginity” is an outdated concept — one that’s deeply connected to a cisgender and heterosexual (cishet) worldview that many LGBTQ+ people outright reject — it’s a notion that carries a great deal of weight for a number of trans women. “Something that I know from running post-op groups, and from my own experience in talking with people, is that it’s something that people by and large do place some significance on,” Hammond says.
It’s not hard to see why that is: First-time sex carries a lot of importance in our culture. Even if you, personally, didn’t think punching your v-card was a particularly big deal, there’s no question that “losing it” carries a lot of weight — particularly if you’re a woman. Our culture presents losing one’s virginity as an act uniquely capable of transforming a person from innocent girl to mature, experienced woman; as though some there’s a fundamental bit of female knowledge that can only be accessed through vaginal absorption. No matter how progressive your sexual politics, it can be difficult not to get swept up in the idea that our first experiences of intimacy are still significant.
Of course, for transfeminine people, virginity narratives can be a bit more complex. When transition occurs after years or decades of sexual experience, that first experience of sex as a woman isn’t the first experience of sex, and all the encounters that came before can influence and impact this wholly new way of engaging in intimacy. Yet all those cultural ideas about sex as a woman — and first sex itself — still shape those initial forays into feminine sex, for better and for worse, in ways both exciting and awkward.
No matter what your transition looks like, presenting as a woman can radically alter the way your partners treat you. For those who medically transition, there are other factors to consider. Hormones can lead to a shift in the experience of arousal and orgasm, dramatically altering what sex feels like and how it unfolds. And, of course, women who pursue bottom surgery emerge with a body part that more readily aligns with age-old ideas of the loss of feminine virginity.
But how do these heady concepts of purity and deflowering translate into the real world experience of post-transition sex? Like so many aspects of sexuality and identity, it depends on the individual. “I think [first sex after surgery is] probably more significant for hetero trans women than it is for queer trans women,” Hammond tells me, noting that some trans narratives of virginity loss still follow the cishet archetype, imbuing penetration by flesh penises with a mystical, magical power.
For Hammond, a queer woman who’s had partners of a variety of genders, the bigger appeal is the way that having a vagina makes it easier for her to navigate sex with less trans-competent partners, and allows for a wider range of potential partners, even within the queer community. “You don’t have to contend with the cotton ceiling,” Hammond tells me, referencing a phrase used to describe cis women who reject non-op trans partners.
Yet as much as she appreciates her vagina, Hammond thinks there’s a danger to putting too much emphasis on first sex after bottom surgery. “Having bottom surgery can be a big goal for a lot of people,” she tells me. And the logistics of post-surgery sex — doctors suggest waiting three to six months, and sometimes longer, to test out one’s new genitals — can amp up the anticipation.
But new vaginas can be painful, unwieldy, and sometimes confusing. They also require some amount of maintenance. Post-op trans women are encouraged to adhere to a regular regimen of dilation, a process that involves inserting a stent into the vagina for an extended period of time. Without dilation, a new vagina can lose depth or width, but the process can be painful and difficult to get used to, as well as a jarring reminder that there’s more to bottom surgery than just the surgery itself.
Hammond notes that early on, a vagina can feel more like “a weird stoma” than an erotic part of the body, and even under the best of circumstances, trans vaginas aren’t as pliable or stretchy as their cis counterparts. “When you imbue so much significance into something… it’s often a let down or a disappointment,” Hammond says. “Things aren’t as perfect as you expect them to be.” This reality can ring true for virtually any highly anticipated initial sex experience.
Bottom surgery can create a dramatic demarcation between sex pre- and post-transition, with the creation of an entirely new intimate body part that offers access to a radically different landscape of sexual experiences. Yet even without a surgical procedure, transition can alter the experience of sex in physical, mental, and emotional ways. Exploring sex as transition changes your sense of who you are can be a fraught experience — one as terrifying as it is exciting.
Around the time that Hammond was recovering from her bottom surgery, Fox Barrett, a 34-year-old cartoonist based in Austin, TX, was first beginning to understand herself as a woman. “Coming out was something of a drawn out process for me, with a slowly expanding circle of people who knew drawn out over most of a decade,” she tells me over email. “But I came out as trans publicly a little over a year ago. For good or ill, it was largely prodded on by the Pulse shooting. I guess in the moment I felt like I had to come out almost out of spite? I'd been waffling and doubting myself for years, but after that tragedy I was so sad and so, so angry that all my personal fears just... shrank into nothingness.”
Barrett’s public announcement didn’t dramatically alter her romantic life. “My girlfriend was the first person I ever came out to, and it was years before I told anyone else,” she notes. But it did give her the freedom to begin taking estrogen, a possibility that filled her with a mixture of excitement and dread.
“The common wisdom is that ‘less testosterone equals less sex drive,’” Barrett says. "I was scared I might just not want to have sex," or equally troublingly, that “I wouldn't be able to have sex at all (or at least not without help from drugs like Viagra).” There was also the fear that, even if estrogen didn’t impact her ability to get erect, its atrophying effect on her genitals might render her a less satisfying partner in bed. “There is, perhaps, a more sophisticated way to put this,” she says. “But: I was worried I wouldn't be as good a lover if my equipment shrank.”
Barrett isn’t alone in the fear that taking steps to embrace her true self might make her a less desirable and less competent sex partner. Vidney, a 33-year-old artist based in Portland, OR, spent a good chunk of her 20's publicly exploring her sexuality, appearing in queer porn flicks that embraced and celebrated her identity as a masc-of-center genderqueer person who was assigned male at birth (as she identified at the time). “My comfort with my body was strongest when I was performing in porn, shooting with and for queer people,” she tells me, noting that queer porn gave her the freedom to publicly experience pleasure without any expectation of conforming to cishet expectations of sexual identity.
These days, Vidney — a punky femme with a lime green mohawk — bears little resemblance to the masc-of-center genderqueer person who shot all those porn scenes, and she’s still mulling over when she might be ready to make her debut as a transfeminine XXX performer. “The last time I performed in porn was shortly before I came out, and that gap has been largely because of my dysphoria,” she explains. “I've lacked a confidence in my body to put in the model applications and be on screen.”
Even as Vidney sorts out her comfort level with showcasing her current body to the world at large, she’s significantly more comfortable with her sexuality than she was just a few years ago. In the early days of her transition, Vidney struggled with fears that embracing her gender identity might mean sacrificing intimacy and sexual pleasure. “I had a partner who was very upset at the possibility that our sex life would change,” she tells me. Her partner worried “that my attractions would change, or [that] it would be difficult for me to top with my penis — the way we most often had sex.” These anxieties fueled Vidney’s own fears about transition and caused her to delay starting HRT for months.
Yet for all their fears, both Barrett and Vidney found that estrogen opened far more doors than it closed. Barrett, who describes her first-ever sexual experience as “kind of a clumsy mess,” notes that sex after transition “was like I'd never really had sex before,” full of “new feelings, new erogenous zones, new orgasms, fun new pet names like ‘cowgirl.’” Estrogen has changed her orgasms, making them richer, more intense, and more fulfilling. “Also,” she tells me, “my girlfriend says I'm a whole lot louder during sex.”
For Vidney, transition hasn’t just changed the physical experience of sex — it’s also opened up a whole new slate of opportunities. In the three years since she began her transition, she’s experienced a host of firsts. There was her first time topping someone with strap-on, an experience that gave her a deeper feeling of connection to queer femme sex. There was her first experience joining a hetero couple as a unicorn, “the mythical bisexual third who's into both parties,” Vidney explains. Though the term and status of “unicorn” has a complicated history of uncomfortable fetishization, for Vidney, exploring lesbian sex alongside sex with a straight man was a powerful way to reinforce her sense of gender identity.
Transitioning has also given Vidney a renewed sense of mystery and uncertainty that’s made sex newly confusing, exciting, and occasionally awkward. “The first time you have sex with a body that matches your real body is a new world,” she says, echoing the sentiments I’d heard from Hammond.
That newness has been parallel to her earliest experiences of sex, in a way that has little to do with traditional notions of purity and transformation. “There is a fear of performing to expectations, of how your partner will respond to your vulnerability, and a relief when it goes well,” she tells me. “The first time, it's inexperience. In the new first experiences, it's wondering what will be new, and what is truly different.”
Though first times can feel deeply important to some, other trans women and femmes aren’t particularly invested in the virginity narrative. Indeed, not everyone keeps track of or even knows for sure what exactly counts as their “first time” after transition.
There are many things that Ashley, who asked that her last name be withheld, has in common with Rebecca Hammond. Like Hammond, Ashley came out as trans over a decade ago; like Hammond, she’s a vocal advocate for trans rights. She even sports a similarly asymmetrical, bleach blonde hairdo, though Ashley’s hair is longer, with the blond offset by the light brown fuzz of her haircut.
And, unlike Hammond, Ashley has never been interested in medical transition, a detail that shifts her relationship to the entire notion of first sex after transition. Unlike other trans femmes, Ashley doesn’t have medical milestones to measure the progression of her transition by, and — perhaps because of that — she doesn’t really have a specific moment that felt like her first time having sex as a trans person. “It’s never felt like it was a different thing,” she says. “It always kind of felt like, 'This is the natural progression of me as a human.'”
Which isn’t to say that transition hasn’t changed her experience of sex. Being seen as a woman has shifted the role that partners expect her to play, helping her to explain why certain gendered terms feel uncomfortable and off-putting.
Prior to transition, she tells me, “I kind of detached from sexual encounters.” Being called by her deadname, being expected to take on a masculine role in bed, or — most uncomfortable of all — being called “daddy” by a partner all felt wrong in a way she couldn’t quite verbalize. “Having everything gendered in bed was really, like, ugh,” she tells me. And coming out as trans helped her understand why: “Oh, it’s because [partners were] viewing me as this, when in reality I’m not that at all.”
"There’s so much more than just physical within sex,” Ashley tells me, and transition has made her vastly more aware of how gendered so much of sex is. Transitioning, she says, has helped her to understand that she doesn’t “have to buy a lot of the stereotypes about how we approach sex,” and that sex can be as individual and personal as gender.
That mental shift can be transformative no matter what your transition looks like. “There's something about shifting the dynamic in my mind of ‘I am a man having sex with a woman’ to ‘I am lesbian having sex with her bisexual girlfriend’ that completely reframed how much I enjoy sex,” Barrett tells me. “I don't spend any mental cycles trying to focus on how good it's supposed to feel. Instead, it just feels like, ‘This is how it's supposed to be.’”
And that — more than any traditional narratives of deflowering, maturity, or “real” womanhood achieved through sex — is the true power of first sex after transition. “I think [loss of virginity] is what you make of it,” Hammond tells me. “There’s nothing intrinsically powerful about losing one’s virginity.” But when it’s an intimate, vulnerable experience of being seen as the person you’ve always felt yourself to be, it can be a truly wonderful and affirming thing.
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