Welcome sexy babies to yet another week of 1-800-DREAMBOAT, my monthly advice column. This week is all about sex with trans guys, which (let’s be honest) is the content we are all here for. Oh, to love and be loved! I could write some long preamble about the trans masculine body as a site of erotic reclamation for the patriarchy’s worst doings or about how blowjobs are a soothing balm with a t-dick in your mouth, but I think I should shut up and just get straight to the questions.
🔋 SEX ON TESTOSTERONE: HOW TO HAVE SEX ON HRT BEFORE TOP SURGERY
🔥 FRIENDS WITH BENEFITS: HOW TO GET YOUR TRANS MASC CRUSH TO REALIZE HOW SEXY HE IS
👅 BLOW JOBS AND JERK OFFS: HOW TO WORSHIP A TRANS GUY FOR THE FIRST TIME
I’m not a therapist or a mental health professional. I am an artist, writer, and trans masculine sage with a penchant for supporting others to live the life they dream about. I try to answer these questions with a critical eye, from my heart of hearts, with a fierce passion for community, accountability, and love. Take what you like, leave the rest, and (as always) feel free to push back or talk about it in the comments. Let’s go!
💌 Dear Dreamboat,
I’m scared to have sex for the first time after transition but pre-top surgery. Any advice or experiences you can share?
Signed,
Scared but Horny
Dear Scared but Horny,
Thank you for writing in with this question. First off, I just want to say been there. I started thinking back on that time eight or so years ago and really want to conjure up that emotional space in my heart as I write you back.
Medical transition is weird AF. We are literally reconfiguring our bodies, no instructional manual. Going rogue. Off the charts. A complete physical, emotional, and mental rewiring. Everything is unknown. You no longer look like who you used to look like, but you also still kinda do. You are shape-shifting. Is your face always going to look this puffy? Wait, you can get hard-ons now? Hair in new places—butt crack? You feel sort of like Frankenstein, but hotter. A lot gets easier, and some stuff gets harder.
To call it “a transition” is the understatement of the century. It’s a fucking full-on renovation. Your body, a house you weren’t allowed to live in, being restored back to its original state. No wonder you are scared to have sex! It is scary and vulnerable and momentous. My advice for you is to listen to yourself. When the right person comes along, you feel will it in your body.
When I started T, I was horny all the time. And I mean like, all the time. Like if I had entered into a masturbation competition during those six months, I would have smashed it. And I was smashing it. I was rubbing my bits on everything and everyone around. That meant hooking up with exes, Tinder dates, couples—separately, never been a unicorn—massage therapists, long-distance lovers. And that worked for a while, until boom. I was struck down by chest dysphoria for the first time in my life, and suddenly I was out of my body.
I remember being so scared to have sex after I experienced dysphoria. I had gotten a top surgery date set for early February, which took a huge weight off my shoulders, but what was I going to do until then… be celibate? Sex wasn’t feeling particularly accessible to me, but that felt sad. I didn’t want to not be able to have sex just because I had complicated feelings about my chest, but I was also deathly scared of sharing my body with someone new—a body I had outgrown.
What if they thought I was weird? What would I do if things were heating up and someone tried to touch me there? Freeze, push them off, or let it happen? I didn’t know how to say that a part of my body was off limits. What if it wasn’t hot or sexy, or it disrupted the flow? Was I just gonna be this massive bummer in the bedroom? I was grieving the simplicity of moving through the world as a cis person. God why does being trans make everything so complicated?
Then, three days before my top surgery date I met my ex-partner. The last thing I was thinking about was sex, but there we were. After a few too many rounds of homemade salty dogs in my bed as the sun came up. And you know what? I forgot that I had ever felt weird about my body before.
I kept my shirt on the whole time we fucked, and it was sexy. She even grabbed the back of my shirt and fanned me off when I got overheated. It helped that she had dated trans guys before—this wasn’t her first rodeo—but ultimately sex with the right person helped me transcend my body, realize what I was capable of, be present with myself and someone else. It was perfect.
So my advice is to share yourself sexually with people who deserve it. Follow your intuition. Be choosy. You have a right to be. So often as trans people, we can think that we don’t deserve much. We feel like we would be lucky if anyone found us attractive, let alone wanted to sleep with us. But you are fucking sacred. Your body is sacred, even if you aren’t in your final form yet. You are not disempowered by being trans. It’s your superpower. You aren’t at a disadvantage, despite what the world tells us.
You are going to find someone who loves and worships your body no matter where you are at in your journey. Someone whose sexual world you are going to rock and revolutionize. And if it doesn’t work out with that person, you are gonna find another. And they will tell you over and over again how hot and dreamy and sexy you are. And it might take you your whole life to believe you are everything that they say you are, but it’s true. You are.
So listen to yourself, oh, and wank a lot so you can know what feels good and what doesn’t. That way you’ll be able to communicate it in the moment. Remember it’s a journey, and you’re only at the beginning. Be patient and keep wanking. The right people will show up, and you’ll forget you were ever scared to begin with.
xo
💌 Dear Dreamboat,
I have this amazing friend who I also have sex with. We’ve been sleeping together for over a year now, and he happens to be trans. I tell him how sexy and hot he is consistently, but he doesn’t know how to take the compliments. He often will say things like “I don’t deserve this,” or “I’m weird because I’m trans,”or “I don’t fit in anywhere.” Do you have advice for how to handle these comments? I want him to know how amazing he is, but I don’t want to make him uncomfortable.
Signed,
Cis and listening
Dear Cis and listening,
We love a friends with bennies moment, especially with local hot trans masc trade! So congrats. It sounds like you’ve scored and so has he. As a trans person who also used to have a hard time taking compliments, I understand the belief system that he is working within. I’ve also dated enough cis femmes to truly empathize with how fucking annoying it is when a trans guy doesn’t see how sexy he so obviously is.
Just know that his journey to loving himself is a long and winding road. He is having to unpack and unlearn everything that he has been told about himself. There is zero representation, no positive role models. Never has society ever told us that a trans man is hot, let alone sexy. Unless he is Laith Ashely, and even then… some people don’t even think he is hot simply because he is trans! Can you believe that?
My point is that we are working against a forceful and extremely loud powerhouse of negativity, cruelty, and disgust for the very fact that we exist. Never mind the fact that we could ever be attractive, desirable, or worthy of attention from cis women! We are working from within a deficit, trying to claw our way out towards a hazy mirage self-love. I’ve done a lot of work on this area of myself, and there are still days when I’m absolutely flailing.
I say all of this so that you can understand where exactly he is coming from when he says things like that. Which you probably already know. But if you think you know, just sit a little longer with the pain those words bring in your heart so that you really understand. It sounds like he needs more trans community in his life so that he can start to see himself reflected back in beautiful, real, and healthy ways.
But that is his journey. All you can do is listen, try to understand, and call bullshit when you see it. As far as making him uncomfortable, speaking from my own experience as a trans guy, I don’t think I could ever be complimented enough. Feeling appreciated and cherished is my f***king kink, even if I have a hard time absorbing it in the moment. It still gets in somehow. Just because he can’t receive compliments them, doesn’t mean you should stop giving them. If he wants you to stop, he’ll tell you.
xo
💌 Dear Dreamboat,
I (a cis/gender-questioning woman) have started seeing a ✨ beautiful ✨ guy (who is trans). Our communication, joy and sex life are amazing, and it's genuinely the kindest, most respectful and loving relationship I've ever been in. Basically, I'm completely smitten.
Up until now, he's been fairly guarded about his body, but has started to express interest in me going down on him - something he's never explored with any other partner. The thing is, I've never been with a trans guy before, so we're both navigating something new to us. We've had a lot of conversations about what we call our junk, how and where we like to be touched, etc. But I don't want to put the burden of 'dominance' on him now that he's starting to be vulnerable with me.
Do you have any advice/tips/wisdom about pleasure (with hands or mouth)? I want his first time to feel like 🙏🏻 worship 🙏🏻, which is no less that he deserves.
Signed,
One very loved up hunny
Dear Loved up Hunny,
To be in a loving relationship with a trans guy is to hit the proverbial jackpot! I’m so glad that you wrote in because there are virtually no resources out there on how to pleasure trans men. Questions like these are the whole reason I started this advice column in the first place, so your inquiry really makes my heart thump. The people need to know! I love that you are taking the initiative to learn, do your research, and come to the table with your mouths and hands fully resourced and ready to go.
Okay, so obviously not everybody uses the word ‘dick’ or ‘cock’ to describe their junk, but since I do, I’m gonna use that language here. All bodies are different and everyone experiences pleasure differently. But the first thing I can tell you is that if your partner is on HRT and has experienced any bottom growth (like any at all), then there is likely something down there to suck. The key word here is suck. If there is a spectrum from licking pussy to sucking dick, going down on a trans guy on HRT is on the dick sucking side.
I was also the first trans guy that my partner, AJ, had ever been with sexually. I felt like she would be a good person to answer this question as a cis femme who was new to the craft of trans blowjobs not too long ago. She is absolutely mind-blowing with her mouth (pun intended), so we sat down with some red wine on the couch last night and I asked her to reveal her technique.
“Every body is different, but there is a technique that I’ve found works for me. When we first met, Dusty told me that he really likes getting his dick sucked. That was helpful because I heard the word ‘dick’ and ‘suck,’ so I knew the motion was going to be sucking. I start gentle. Maybe a few licks and wet kisses, but the primacy thing I’m doing is using my lips and my mouth to suck.You can suck softly at first. The more erect he gets in my mouth, the harder I can suck, but I always start slow. The tip of his dick is super sensitive, so what usually gets him really going is pulling back and forth on his foreskin and moving up and down his shaft with my mouth or hands. I pull and build suction at the same time with my mouth and lips. Sometimes I lay my hand flat against his body to isolate his dick in the space between my fingers, and I can sort of jerk him off at the same time as sucking.
Now that I’m talking about it, I think my top lip does a lot of work. I press down with my top lip and apply pressure against his dick while I engulf him and take his whole dick in my mouth. And sometimes I go in sideways at a 90° angle so I can really go all in. Sometimes, if he is really turned on, I can suck pretty hard. But a really important thing is to build and understand the right relationship between sensitivity and pressure.”
One thing that AJ and I talked about last night that can be helpful when having sex with trans folks is to really vocalize how much you enjoy it. That doesn’t have to be your opening line, but I know that it was a game changer for me to be with a partner who was able to really express how much they love having sex with me, loved my body, and loved my dick. For a while there, AJ had a reminder set on her phone for 8pm every day to remind me that my dick was the best she’s ever had LOL. That type of over-the-top reassurance really helped me feel comfortable and trust that my partner actually does desire my body. There is a lot of transphobia that can get in the way of me loving my body, so I really do need all the reinforcement I can get.
But it also sounds like your boo might not be there with his body yet, as he is just now starting to build a space of trust between his body and someone else. So my advice is to go slow. You can compliment him in more general ways while you learn what he likes. Tell him how much you love his body and how attractive he is. How much he turns you on. Reassure him. Be gentle, curious, willing to experiment, and unattached to the outcome. Throw your ego out the door. Release the need to be an expert or ‘good’ at anything right away. Just listen.
I probably don’t need to tell you this, but I just think the most important thing while having sex is just to use your intuition. Really listen to someone else’s body. Listen to the language it speaks back to you in the energetic feedback loop between mouth and hand and skin and sweat and noise. You can ask for feedback if it’s not being willfully given, but it sounds like he might not know exactly what feels good yet. You can also ask ‘does it feel good when I do this?’ as you explore and get know the topography of his junk. That way you are guiding him into telling you what he likes rather than placing that burden of teaching on him.
I just want to say that it’s actually quite poetic and beautiful that this is new to both of you. You get to go somewhere new together, invent language and motion, and co-build a world of desire for his body. Which sounds like something that he hasn’t felt safe enough to do with anyone else yet. This makes me want to cry. I’m so happy that you’ve found each other. And with that, many blessings on your dick sucking adventures!
I’m praying for a lifetime of trans happiness, hard-ons, and orgasmic magic for both of you!
xo
Thank you for reading! If you have questions for next time: you can submit them here.