People Tell Us About Their First Sexual Experience After Transitioning

"I thoroughly enjoyed my position in the sexual experience because plain and simple, I was the woman."
Images by Ashley Goodall

There are lots of milestones separating adolescence from adulthood, but few carry the same gravity as sex. Losing your virginity feels significant because it affirms how you feel about others, but also, crucially, how you feel about yourself. And for people who are transitioning, a first post-op sexual encounter can be even more about self-discovery, with ramifications that can be life changing.

Here, three people describe in their own words their first intimate experience after gender affirmation surgery. All have been lightly edited for brevity and clarity and just a warning, a following story contains references to sexual assault.


Anne-Marie* is 56 years old

I came out as transgender five years ago. My wife and I divorced shortly after. She felt betrayed and I couldn’t argue with that, because I had been keeping a part of me hidden to her, but also to myself.

I had sex reassignment surgery (SRS) two years ago. After I came out, things started to make sense and fall into place. Quickly. I knew SRS would be the only way I could truly live as myself and I felt as though I’d wasted enough of my life living as someone else. In the inevitable physical pain post–op, I found relief. This huge lie that I’d been carrying around my entire life had vanished. I didn’t have sex for a year after the surgery out of fear of the unknown and also guilt, I still loved my wife and sex with someone else felt like betrayal.

The first time I had sex post-op was a one-night stand—I’d never had one before! I was drinking a martini at a bar, by myself, and I got talking to the bartender. He was charming, attractive and definitely much younger than me. We went back to his house and had a lot of sex. I can’t remember ever having that much sex in my married life. It wasn’t that I hadn’t enjoyed it. I’d just always felt as though something wasn’t right within myself, like deep within my body and the way it functioned.

I’d always felt self–conscious during sex. But that night, I didn’t feel that at all. I felt confident and strong and as though I was in the right place. I heard myself asking for things I’d never thought about or wanted before, thoroughly enjoying my position in the sexual experience because plain and simple; I was the woman. That truth alone, turned me on more than I knew was possible and was a really affirming feeling. Life since that night has been increasingly more fulfilling. I’ve been dating people without limits, without hesitation, and without labels. By understanding my sexual desires, I understand myself better as a woman.


I don’t think I’d be here today if it wasn’t for the strong LGBTQ community present in today’s society and in the media. Visibility is so important, and we have to be the change we want to see in the world.


Isabel* is 32 years old

I knew the surgery was what I wanted from a young age, and I was excited to start dating post–op. I’d never enjoyed sex before because I didn’t like being treated like a boy, which is unavoidable if you’re naked and have a penis. I was a pretty boy and popular with girls, which often found me in sexual experiences that left me with immense guilt. I always knew that without a penis this guilt wouldn’t exist.

My first date after surgery was with this beautiful girl. She looked like a girl from my dreams; a blonde pixie cut, piercing blue eyes, and eyeliner thicker than Amy Winehouse’s. We sat in a picturesque bar and drank too much wine. I told her about my guilty sex life as a teenage boy and my surgery and she told me about her struggles with sexuality and of being labelled within that. It felt like an honest exchange between two people who were coming to terms with who they were. So I invited her back to my house, not sure what to expect.

After I’d poured us more wine, she launched into “foreplay” without warning. She was really rough with me, tearing my clothes off, pushing me onto uncomfortable surfaces and rubbing my clit way too hard. I was so shocked by her sudden change of demeanour that I let it happen for a few minutes before asking her what the fuck she was doing. She apologised said she didn’t know what I liked and encouraged me to continue exploring with her. She said she’d go slower. I was so hungry for experience that I ignored the warning signs my body was giving me.


We drank some more wine and started touching each other gently for a while, which was nice. It was really nice to be touched by someone in the spots that you’d imagined for so long. Then she went down on me, but it wasn’t considerate or gentle, it was rough and excessive, as though she was just trying to make me wet for the sake of it. She pulled a strap-on out of her bag and before I had time to comprehend what was about to happen, she was fucking me hard and heartlessly. I felt truly empty. I didn’t resist her, because in that moment, I thought it was my fault—that I’d made a mistake with my own identity. I lay there wondering whether I was really a woman. Did I go through all this pain for nothing? Is this really what it feels like?

I didn’t know if it didn’t feel right just because I didn’t like it, or if it didn’t feel right because my body was different now. I felt as though I couldn’t trust my own instincts anymore. I started to cry. She saw my tears and stopped, pulled her strap-on out of me and said: “I thought that’s what you wanted.” Then she redressed and left, without so much as a hug or a goodbye. It’s an experience I’ll never forget. For months afterwards, I didn’t feel confident to have sex with anyone.

Now, I have a partner and we have a healthy sex life. I am happy, I feel completely myself and I hardly ever think about that night anymore. I know now that the way that I felt was valid and not unusual for someone that had been through so much change at such a young age. I think it’s really important to be careful who you choose to let into your world and to remember that the way people act towards you isn’t always a reflection of who you are.


Article is continued below but while you're here watch "Island Queens: Growing Up Remote, Transgender and Indigenous"

Kaitlyn is 25 years old

I met Grace on Tinder and we’d been going on dates for a month or so before we had sex. Our first sexual experience together was my first post–surgery and first ever. I’d never had sex before. I’d never been kissed before. At the time, Grace identified as male. For us it was really wholesome, we got to figure out what we both liked from the very beginning. I’d had conflicting feelings about my gender for years, but I only started taking hormones two years before the surgery, when I was 20.

After going on hormones, I generally became more interested in relationships. I started looking in the mirror, and recognising my reflection, liking what I saw and wanting the progression to unfold naturally. I’d never really been attracted to anyone before, nor had I been curious what I was attracted to. I’d never sought out sexual experiences because I didn’t want to bother, unless I truly felt like me. My relationship with my genitals was disconnected. My penis was present, but not useful or desired. I felt ambivalent towards it. But once I’d had the surgery, I was on completely new grounds with sex. I was excited to try it, because from everything I’d heard, it was great. I like to throw myself deep into the unknown as I find it leaves less room for overthinking, worrying what could go wrong, or imagining scenarios that could end up disappointing you in real life. So, Grace and I just dived in.

I’m not a particularly sexual person generally, but I really enjoyed it. It felt very normal in a way that was unusual and new. For me, being able to do penetrative sex is incredibly affirming, as it allows a sexual experience that is in line with the norms of my gender instead of outside them. For it to be the within my gender norms, for my first time ever having sex, it was an enjoyable novelty. Having a vagina gave me the power to not pretend anything away. Once you have that feeling, it’s extremely liberating. Sex post–op can be scary, but not as scary as you think it is. It’s a huge relief. Grace asked me once “When I have sex reassignment surgery, is it going to feel like me?” and I think that’s a question that a lot of trans people have before surgery. I can tell you, that when a nurse is cleaning your clitoris with an alcohol soaked Q-Tip, eight days after you’ve had surgery, it feels like you. It feels like you’re in pain, but it’s really you.

Interviews by Laura Roscioli

*These people requested pseudonyms.