Sex is one of those things that everyone wants to be good at, but when movies, books, TV, and porn tend to exclude, if not censor, trans experiences, it leaves a lot of lovers out there lost and confused. Transmasc people in particular have been historically shunted, making it feel impossible to find accurate representation for how to have sex with a trans man.
As an intimacy coordinator and consultant, my work is steeped in many awkward conversations. Whether it’s simulated sex or the real deal, I have a lot of experience handling when things go very wrong — and that can often be a result of one or more parties being too embarrassed to ask about what they don’t know.
Whether you’re a trans person exploring T4T sex for the first time, a cis woman who has historically dated cis guys, or maybe a cis gay man who's never hooked up with a transmasc person, having a new sexual experience can feel daunting without guidance, and your head might be full of questions. Should I know this stuff already? Am I going to be able to get this person off? What if I say the wrong thing or ask the wrong question?
That’s why we’ve asked a range of transmasc people for the best sex advice they can give. In this guide, we’ll go over common misconceptions about having sex with a transmasc partner, the breadth of the transmasc spectrum, and why the experience isn’t a monolith. It’s important to acknowledge before diving in that there is no single piece of advice that’s going to work for everyone you encounter. There are some terms used that while highly erotic for one person might trigger gender dysphoria for others. So take what you will from here, but much of your success comes down to talking to your partner.
Talk to your partner
As uncomfortable as it can be to talk about wants, desires, boundaries, dysphoria, or anything else that might come up, it’s best to chat with your partner(s) before things get heated. Even if this conversation isn’t long, there are things you’ll want clarity on before jumping into bed. If it’s your first time hooking up with a transmasc person and you don’t know what to ask, start with something like: “Is there anything you want me to know about how you want to be touched?” “What makes you feel good?” or a good old-fashioned, “How do you want it?” This can be hot! Consider making this moment flirty or straight up filthy. As long as it’s thorough, no one says a check-in has to be boring.
When it comes to questions that are more gender or genital-specific, proceed with tact. “A lot of people tend to ask you questions about your transness during pillow talk, and some of those questions are too intimate for a hookup,” Amun-Ra Tutenkhamen, a 29-year-old Afro-Indigenous chef and kink/sex educator, tells Them.
That’s why you should keep your questions relevant to what you’re about to do and appropriate for the level of familiarity you have of one another. Also, don’t just ask — listen, digest, and integrate what you learn into how you move. “What has bothered me is when I've said, ‘This is how you talk about my genitals. These are the pronouns that I use,’ and then someone disregards that during sex, or asks me if they can refer to something differently,” Tutenkhamen says. Don’t be this person.
You also might be nervous about saying the wrong thing and avoid asking all together. But, “there's some really well adjusted trans people out there,” Sam Clarendon, a 34-year-old Brooklyn-based writer and educator, tells Them. Give the person you’re hooking up with some credit! Proceed with respect and grace and it’s likely that your partner will assume best intentions. Trust them to tell you if you’re making them feel some type of way. (Or just ask!)
Don’t be a weirdo!
Don’t get me wrong, being a freak in the sheets can be a great thing if you and your partner(s) are into that. But being a weirdo and fetishizing prospective hookups isn’t it. Think you’re asking too many questions? Why is the spotlight on them? This is especially important if you’re cis because you risk creating a dynamic where you’re implying your body is the default and your transmasc partner’s is not. It can also place an unnecessary amount of pressure or scrutiny on a trans person if they feel like they’re being interviewed about their personal experiences or body.
“I’ve spent a lot of time thinking about my own pleasure roadmap, so I want to be met there,” Lisa Feliciano, a 34-year-old New York City-born academic and organizer, says. “It can be hard for me to engage with people who are like, ‘I'm here exploring’ or ‘I'm new’ or ‘I need to learn.’ Because that’s not what I'm offering.”
Ask yourself: Are you trying to have a mutually intriguing sexual experience that’s grounded in chemistry and earnest connectivity? To get pleasure and also offer pleasure? Cool. Does this feel like an experiment or fleeting sexual curiosity? Something you want to check off your list? If the answer is “yes” to those last few questions, you might be fetishizing this person. Not cool. Take that energy to a science fair project!
“Some people are too excited about the prospect of hooking up with a trans person for the first time,” Tutenkhamen says. “They’re not slowing down and thinking about, ‘Why am I here? And what do I want?’”
Remember that everybody (and every body) is different
The old adage goes, “When you assume, you make an ass out of you and me.” And we came to eat ass. Which is to say: Leave your preconceived notions about gender at the door. You can't assume just because someone is transmasc, they’ll look, act, or carry themselves in a certain way inside or outside of the bedroom. Transmasculinity is a big and beautiful spectrum. It can’t be overstated: Ask people what they want their parts called. “Dick,” “clit,” “cock,” “junk,” “front hole,” “pussy” — these are all terms that could work for your boo, or they might not. That’s why asking is key.
Similarly, many people prefer to have their chest referred to as exactly that: a “chest.” This is even if they have fatty tissue in that region. Others prefer “breasts” or “tits.” There is no direct correlation between someone’s gender identity, presentation, or pronouns and how they want any part of their anatomy referred to.
“I’ve had people love my T-dick and be so into it and affirming and make me feel really sexy,” Bobbi Jaggon, a 30-year-old London-based queer photographer and pornographer behind Rub Magazine, says. “I’ve also had people who have completely avoided touching my genitals or not touched my chest or never touched my nipples. I’m guessing it’s because of this fear of my dysphoria.”
While it’s very much the case that some transmasc people don’t want their chest, nipples or genitals touched, it’s also true that just skipping over whole swaths of someone’s body could be the total wrong approach. So check in!
Giving head
Not everyone likes getting head the same way. Maybe your partner wants it to feel like you’re sucking on the tip of a popsicle with a combination of pressure changes with your lips and flits of the tongue. Maybe they want you to pump your mouth up and down around the shaft. Or maybe your partner wants it to feel less like suction, or a blowjob, and more like a circular motion with your tongue. Maybe they want to be penetrated with fingers or a toy during oral sex. Whatever it is, don’t be afraid to ask and therefore improve your skills, perhaps supplemented by Them’s guide on giving head.
Consider the orgasm
There are a million ways to check in to see if someone had a good time or feels finished — and it doesn’t always point to or center orgasm. It’s important to check in with your partner about how the experience was for them as a whole. Is an orgasm something that was wanted but wasn’t achieved? Try asking if they’d like to explore different ways of getting there with you. Whether you go in for round two, or it’s giving “maybe next time,” the hardest part is being brave enough to bring it up.
If your partner says orgasm wasn’t the goal, perhaps because they want to alleviate the personal pressure of achieving climax, take this at face value. Especially within queer and trans communities, orgasm isn’t always the ultimate goal.
Practice safer sex
First of all, wash your hands. This is super important with people who are on T, as those partners are especially at risk of developing infections like bacterial vaginosis (BV), urinary tract infections, or yeast infections. And of course, this is the case with any hand-to-genital contact, not just penetration. But even if your transmasc partner isn’t on T, please come correct.
While we’re on the subject of sexual health, a common misconception is that people on testosterone can’t get pregnant. Talk to your partner about their preferred method of preventing unwanted pregnancy.
You’ll also want to be aware that some folks on testosterone can experience dryness and difficulty self-lubricating. That’s what store bought lube is for! Or spit. Whether you’re fingering someone or straight up fisting, a well-lubricated front hole is important for maximum pleasure and safety. Broken skin can lead to increased risk of infection. Lube can also come in extra handy if anal penetration is on the table for either of you.
Furthermore, an STI check in is always good practice! PIV, anilingus, head — everyone has different comfort levels, so make sure you’re on the same page. Note: if you’re hooking up with a person who has experienced bottom growth and being penetrated by them is an option, you’ll want to have a conversation about barriers like latex underwear or dental dams.
Sex toy strategy
Whether your partner is using sex toys to deepen their own connection to their body or just to have fun, toys could be critical. Many people I spoke with referred to their “bio-dick” and their strap interchangeably, while others might call it something else, like a “bonus dick.” Select a toy with your partner’s insight, because different bodies at different points in transition are going to have different needs.
“When I started taking HRT and my material relationship to pleasure changed, my magic wand didn't really do it for me anymore,” Greta or “G,” 29, of Brooklyn’s trans-owned, quеег-centered sехuаl health and pleasure shop Toolbox Collective, says. Conversely, you might be hooking up with someone who can only get off with their wand, or is still figuring out what works for them. Again, everybody (and every body) is different! That’s why it’s important to make a ton of space for your partner's desires and sensibilities.
Mutual masturbation can be really hot (and informative)
Watching your partner jerk off can generally be a turn on. It can also be really informative in understanding how they like to be stimulated. “Do you want me to touch you like that?” Sometimes, the way we touch ourselves is different from the way we like to be touched by others. You can take this a step further and ask if you can put your hand over theirs as they masturbate to get in tune with the rhythm of their body. Assess if this particular lover prefers a more handjob-esque stroke (with your fingertips gripping the shaft of their dick or clit, pumping up and down) or if they like it when you apply pressure with your fingertips, rubbing in an up-down, and circular motion.
Don’t forget to have fun
There are plenty of reasons to have sex. But a big one, for a lot of people, at least sometimes, is to have fun.
“Sex doesn’t have to be this very serious thing with the perfect mood lighting,” Feliciano says. “Sex can be sloppy, awkward, funny. People fart. Sometimes sex faces are funny looking. There’s a real humanity to that. And that vulnerability is what's hot for me.”
You can fumble through it together. Once you’ve checked in around any hard boundaries and gender dysphoria, go ahead. If you’re having candid check-ins before, throughout, or after, you’ll just have to trust yourself and your partner at a certain point to get through the experience even if there are hiccups. And leave room for the possibility that it could be really fun, even if it does get uncomfortable.
The question of how to have sex with a transmasc person ultimately comes down to being a confident yet curious sexual partner. Worry less about saying or doing the right things and lead with honesty, openness, and empathy. Once that’s achieved, the fun begins.
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