Hookups, toys, safety, and identifying your preferences…
As a trans man top, having positive experiences with casual sex has been so validating. Growing up, I never thought that anyone would want me or my body. I experienced so much insecurity around sex and feared that I was completely undesirable. But now, as an older trans man (I’m 29), I’ve had some great dates and sexual experiences with a wide range of people. I’m proud to walk the world as a dominant top, and want to offer some advice for other trans men who are also interested in topping.
Regardless of where you are in your transition journey, if you’d like to explore how to top sexily and safely, then this guide is for you. From tips on discovering your topping preferences, to suggestions for sex toys and how to navigate dating apps, I’ll share insights from my own journey, and direct you to expert resources that support fulfilling sexual experiences.
Discovering your sexual preferences as a trans man
Firstly, it shouldn’t be assumed that all trans men want to top. There are many trans men out there who love bottoming and being penetrated—that’s hot, sexy, and totally your choice. You might choose to bottom entirely or to top entirely—or you might figure out that you prefer being a switch. Your preferences are completely up to you, and are not dictated by your gender or sexual identity.
Some trans men instinctively know where their desires lie from a young age, but for others, this may be a longer journey of inquiry and understanding. There is no timeline for figuring out your sexual preferences, and self-discovery is an ongoing evolution.
It’s also useful to understand the difference between power dynamics, and topping and bottoming during sex:
To be dominant or the “Dom” is to be the person who holds power over your submissive partner. To be submissive or the “sub” is to be the one who relinquishes power and submits to the dominant partner during sex.
To top is to be the person who penetrates the other person. To bottom is to be the person who is penetrated.
Your preferences for power dynamics during sex (whether you’re a Dom, sub, or a switch) are not the same as your preferences for topping and bottoming. I want to get away from the assumption that you can only top if you’re the dominant one. You could be an amazing submissive while topping your partner and following their commands in the scene. Just because you might have more sub tendencies doesn’t mean you can’t also be a great top.
Exploring sex toys
You don’t have to use sex toys when you top, but if you’re interested, here are some suggestions:
Dildo and strap-on harness
This might be the version you’re most familiar with. You can use a regular strap-on harness, and attach whichever dildo you and your partner(s) prefer (ones with flared bases will likely fit more securely). Some harnesses will also come with interchangeable rings, so you can switch between different sized dildos.
Elsewhere, if it feels more comfortable or casual for you, you might opt for a harness that’s shaped more like a boxer brief—which can double up for packing as well as sex.
Strapless strap-on dildos
If you’d prefer not to wear a harness, and would like some internal stimulation or penetration while topping, you can try a strapless strap-on. These are usually designed with two ends: one for penetrating your partner, and the other to put inside yourself.
Some may also double up as vibrators, while others will just stick to classic silicone. Depending on your preferences, this might feel simpler than dealing with harness adjustments.
Dildo with vibrator insert and harness
The Joystick has brought me so much gender euphoria over the years that I have to mention it as my favorite. It can be held in place with the regular underwear you might use for packing, so doesn’t require a harness. Plus, it looks highly realistic, and the vibrating function means the person topping gets stimulation without any internal penetration.
How to approach dating apps
It’s completely natural to feel nervous when you first start using dating apps. Here are some tips to help you navigate them:
Share your trans identity at whatever stage you feel comfortable
It is totally up to you at which stage you choose to disclose your trans identity. Your safety should always come first. You may feel more comfortable sharing your identity during private messages or on an in-person date, or you might prefer to include this information in your bio along with your sexual preferences (i.e. trans man top).
You may also choose to explore connecting with and having sex within the trans community. Having sex with other trans people can come with a baseline understanding that some parts of your body may need to be treated sensitively. On Feeld, you can find t4t (trans-for-trans) connections by filtering your search by gender identity—if you wish to. I’ve used Feeld for years and have found it hands down to be the most trans-friendly app out there for both casual sex and more serious dating.
Be conscious of chasers
“Chasers” are cis people who fetishize trans people. Of course, you may find cis people with good intentions asking questions about your trans journey, because they care or are curious. But if you feel that these questions become intrusive, or if someone stops talking to you when you disclose that you are in a particular stage of your transition (e.g. pre-medical transition), this might mean that they are a chaser or, regardless, it may be a red flag.
At the end of the day, it is completely up to you whether you’d like to meet up with anyone in person. Still, if you ever feel uncomfortable when messaging someone, you may choose to follow your instincts and end your connection.
Discuss your desires before sex
You might find it useful to have a conversation about what sex could look like beforehand, to make sure that you and your partner(s) are on the same page. This could include talking about your likes and dislikes, boundaries, toys, position preferences, and more. You may also explore Feeld’s Reflections tool, to get a better sense of your own desires before sharing them with others.
How to approach hookups and casual sex safely
Inform a friend of your plans
You may have built some rapport with the person you’re meeting, but safety always comes first, especially if you plan to go over to their place.
Consider informing a friend of your plans before they happen. This might include letting them know the location, how long you plan to stay, and asking them to check in during your night via text or call so that you can let them know you’re safe. It may be worth forming an exit plan if your night doesn’t go so well, such as establishing a reason to leave.
The reality of dating as a trans person—in my experience—means protecting myself before any in-person meetings, and preparing for all necessary scenarios. This is with the goal of feeling more at ease during the encounter; preparing in advance is meant to help you relax rather than feel stressed, because you know you have your bases covered.
Communicate preferences and boundaries clearly
It can be useful to talk to partner(s) about your sexual preferences and your hard boundaries. As trans men, we can have complicated relationships with our bodies, and what might be obvious to you (e.g. “do not touch my chest”) may not be immediately obvious to your partner.
To make this an open conversation, all partners should feel free to ask and answer questions. Sex can look and feel however you want it to, and getting on the same page before anything happens can go such a long way to creating a safe and rewarding experience for all.
To find out more, take a look at our guides to understanding your boundaries, and setting boundaries for casual dating.
Know that it’s OK to stop
Changing things up, or stopping completely, is always an option during sex. Even if you have that open conversation about your preferences and boundaries, things can still happen, and a sexual experience is a dynamic encounter. You or your partner might feel triggered, or something might stop feeling comfortable or enjoyable.
Consent is always withdrawable: You might choose to plan for how you will each verbalize the need to stop, such as clearly agreeing on a safe word. Some safe words I’ve used in the past include “stop” or, during rougher play, a different word such as “red” or “pineapple.”
Lastly… have fun!
Often, especially for more casual hookups, I get so much satisfaction out of topping that I don’t necessarily need to come to have a good time. Sex doesn’t have to look a certain way or to end in an orgasm to be enjoyable. So take the pressure off yourself, and enjoy the experience as a whole.
Whenever you feel ready to explore your own desires—and to meet people who want to do the same—Feeld will be waiting for you. For more support, you can access sex and sexual health advice for trans men and trans masculine people from Terrence Higgins Trust.
