Coming Out as Transgender Was the Best Thing to Ever Happen to My Sex Life

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I'd always felt bad after sex, even when the sex was good. When the high of an orgasm faded, I would feel fidgety and sad, convinced that I'd done some indescribable thing wrong. I wanted to be alone, to be closer with the person who I just had sex with, and to be someone else entirely, all at the same time.

Throughout college and for the decade or so after, any time I thought about sex or even my own body, I was overcome with shame and uneasiness. Even when I was sleeping with someone I loved, I felt like I was lying to them, or maybe to myself, about my feelings for them. Because once we were back to just cuddling, what I felt wasn't love or even pleasure, but a deep sense that I wasn't showing them my true self.

It was a painful time for me, until I reached my mid-30s and found the source of all that anxiety: I was a closeted transgender woman trying to convince myself and everyone else that I was a cisgender heterosexual man.

Like a lot of trans people, I can now see signs of my transness even in my early childhood, from the joy I felt when I played dress-up in girls' clothes to the pain of my female friends holding me at a distance. But I took a shaky route when coming out. The revelation came in pieces — and largely with the help of therapy — until one night, I realized what I was actually afraid of: living the rest of my life as a man.

On its own, transitioning didn't solve any of my problems, including my not-great relationship with sex. What it did do is give me space to solve those problems myself, and much to my surprise, that meant learning to enjoy sex.

I was terrified of how other women would see me when I started dating again, but I quickly felt affirmed by even subtle gestures. As a supposed man, I'd internalized the idea that I should be the one to make the first move. So when a woman I'd exchanged a few messages with on a dating app after transitioning asked me out, I was floored. She made it clear that she was taking me on a date, with none of the ambiguous "we should hang" talk that I'm admittedly guilty of myself.

We hit it off on our first date, where we drank mediocre coffee and pored over records together, pointing out our favorites. A few dates later, we kissed in my car after dinner, and it was clear we both wanted to touch each other in a way that just wouldn't work with a gearshift between us. I asked if she wanted to come back to my apartment, and she enthusiastically agreed.

The drive was short enough that we'd hardly lost any momentum by the time we got in the door. Almost immediately, we were on the couch, pulling each other close and making out like teenagers. Her hand moved from my thigh up my stomach and to my chest, then paused. She asked if I liked having my breasts touched (yes), if I had bottom dysphoria (no), and how I felt about her topping me.

I felt myself blush. I haven't had "the surgery" nor do I plan to — having a penis has never made me feel any less feminine. But while I've become accustomed to using a butt plug when I masturbate, I'd never been penetrated during sex. I was eager to try it, and her obvious excitement about the idea only made it seem hotter. I told her I'd never been topped, but that I wanted her to do it.

In my room, she laid me down gently in bed, then climbed on top of me. We took our time exploring with hands and lips while we undressed each other. Lying on our sides facing each other, I began rubbing her clit as she stroked me.

So far, none of this was physically different from anything I'd done before transition, but it all felt new. My body still mostly looked like one we've been taught to think of as male, but the insignificance of that distinction had never been more clear. Despite the anatomical differences, we were two women giving each other pleasure, and knowing that she saw me as I truly was, I felt none of the shame or trepidation that I'd long assumed was just part of sex for me.

Her breathing got faster, her moans got deeper, and as her legs began to shake, I buried my face in her neck, kissing and softly biting. Then she was on top of me again. Still stroking me, she moved her other hand between my legs. Likely noticing how I gasped at the touch, she stayed there, rubbing the sensitive area that had become so much more pleasurable since I started transitioning.

She checked in every step of the way to make sure it felt right and I still wanted everything she was doing. Every sensation felt different for me being on hormones, but this open communication was what felt newest to me. Here was someone asking how I felt, checking boundaries, taking care of me.

At this point, I was still on my back and she was kneeling between my spread legs. She moved her hand further still to grab my ass and then, after a pause for a generous squirt of lube, she penetrated me with her finger. Even though I was a little too nervous to relax fully into it, the sensation was incredible. I immediately pushed my shoulders harder into the bed and thrust my hips in the air, now making no attempt to hold back the loud gasps escaping my lips.

Still perched on her knees in front of me, she took in the full view of my scrawny body, my too-wide shoulders, and my tiny breasts. I felt a little ridiculous and very exposed.

"Do you feel sexy?" she asked. "You look sexy."

Somehow, her vocalizing it made it true. I moaned "yes" as warmth spread through my body, and suddenly I felt beautiful and desirable and feminine in a way I never had before. The feeling stayed long after I had curled up next to her with my head on her shoulder. And, for the first time after sex, the shame never arrived. I was able to enjoy the afterglow, to spend the next day feeling jolts of pleasure when I thought about how we'd been able to take care of each other — both physically and emotionally.

We've continued to see each other since then, and the sex has remained phenomenal. Instead of alienating me from myself and my feelings, sex is finally joyful and celebratory after transition.

And since my initial experience being topped, I've learned that no amount of affirmation or disapproval can change who you really are. But to know that I'm seen as a woman, worthy of desire and intimacy from another woman, makes it easier to see for myself.