The First Time I Had Sex After Transitioning
Illustration by Niallycat
My First Time is a column and podcast series exploring sexuality, gender, and kink with the wide-eyed curiosity of a virgin. We all know your "first time" is about a lot more than just popping your cherry. From experimenting with kink to just trying something new and wild, everyone experiences thousands of first times in the bedroom—that's how sex stays fun, right?
I’m a trans woman, and before transitioning I’d sleep with gay men—although I never identified as a gay man because I always felt like a woman. Now I’m a trans woman, I’m straight-identified, meaning I sleep with straight or bisexual men.
One of the main things I’ve noticed about sex now is how differently I’m treated. I’ve learned a lot about how straight men treat women which doesn't sit well with my feminist beliefs. I didn’t have that much sex pre-transition, because I was so depressed, but when I did, I wasn’t treated like that. For example: Straight guys just don’t care if you come. This is something all women know, but obviously I didn’t realize that until I transitioned.
My first time having sex post-transition—although really I’ve always been trans, so I guess it’s the first time I had sex after presenting full-time—was with this guy I’d been messaging for a while. One of the perks of being a trans girl in the media is that sometimes you get cute guys messaging you, so if I like them I’ll engage with them. This particular guy had seen me on the news when I first started my campaign Nail Transphobia, and he’d got in touch and would like my pictures every now and again and stuff. After a while, he suggested meeting up. We hung out a couple of times before having sex—I’m a Christian so I don’t sleep with people on the first date.
When we finally had sex, it wasn’t good. It wasn’t a nice experience. It was a mess. There’s not much to say really, other than: Men are trash. We were around his house, and I wasn’t planning for it to be a big thing. I’d had sex before—I didn’t consider myself to be a virgin—it was just my first time post-transition. I just wanted to have sex, you know?
It was a lot of fun for him, but not much fun for me. I felt like he was very inconsiderate of my body and my feelings. I didn’t want to marry him or anything—if anything he was more into me than I was into him, but at the same time I wanted him to respect me. We had sex and he came, and it was done—even though I didn’t come. So I said, "Oh, are we done? Because I’m not done." It was embarrassing. I’m not just going to finish myself off now you’re done—you’re not even sitting next to me any more.
When I realized he hadn’t forgotten I hadn’t come, he just didn’t care, it left a really bad taste in my mouth. I realized that this is what my female friends have told me my whole life—guys just use you as a toy to wank with, they only care about themselves. I never saw him again after that.
It was different when I was having sex with gay guys. It felt more equal; you both finish in the same way. Gay guys have more empathy and fucking manners—they want to make you come as well.
I think girls need to be less polite when it comes to sex. We have to instigate the conversations about what we like. Men are okay with not having those conversations, because they’re winning regardless—they can come really easily. Whereas women feel like they have to be polite. But imagine if you were having sex with a man and you didn’t make him come, and you just got off once you’d come and left your cum all over him and walked away. He’d be like, "Come back here! We’re not done!" He wouldn’t even think twice about it.
Some straight guys who sleep with trans girls will believe certain myths—for example, that trans girls can’t come because of the hormones. Maybe some can’t, but I can. Other straight guys I’ve slept with won’t touch me during sex, and when I ask the afterwards they’re like, "Oh, I thought you wouldn’t want to be touched, the last trans girl I slept with didn’t like to be touched."
You’d be shocked how many straight men have sex with trans girls. We’re desirable; trans porn is the fastest-growing category of porn. Lots of guys hit on me and say "I’ve always wanted to try it," which I find quite gross, personally. It’s very interesting how many straight guys—I mean, really straight guys, boys you wouldn’t expect—want to try it. I went to quite a tough all-boys school, and I can promise you that I could have sex with half of the guys in my year if I really wanted to. The majority of straight guys, they don’t want to take us home to Mom, but they do want to take us home and fuck us once. Often, they want us to fuck them—they’re the straightest, most manly guys, and they’ll say, "I want you to fuck me."
There’s a group of straight guys that trans girls call chasers, because they want to have sex with every trans girl they can find; they just go through us all. They fetishize trans women, they’re dick pigs—solely dating trans girls and being really creepy about it as well. It’s not good to be a chaser; it’s not cute. If you only date trans girls and you don’t date other girls, it’s a real turn-off to me, because the only difference between them and me is a dick, literally. There’s being trans-attracted, which is okay, but being a chaser is a horrible thing. I think with every marginalized demographic, there’s always a group of men who are unhealthily obsessed with us, who fetishize us, and it’s not healthy and it’s not a compliment. Also, those guys will never sleep with you once you’ve had surgery; they’re just obsessed with dick. I want to find a guy who likes me for who I am—not because I’m trans, or in spite of the fact that I’m trans. Just someone who’s like, "Oh, you’re trans? OK, cool."
My advice to a trans girl who’s about to start sleeping with straight men is to initiate conversations about sex before you sleep with them, because it’s in your interest. Communicate. We need to say what we want and not be polite about it. Trans girls need to come too! Understand your worth, your body, and your needs and desires. You’re just as worthy as the man you’re sleeping with. Also, if he just uses you as a sex toy to wank in to, steal something from his house! He treated you like a prostitute, so you may as well get paid. I literally do that now. If the guy doesn’t treat me with respect—I just steal something walking out.