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There are many goals and objectives that separate adolescence from adulthood, but few have the same solemnity as sex. Losing one’s virginity feels important because it affirms how one feels about other people, but also, and essentially, how one feels about oneself. And for people who are transitioning gender, a first sexual encounter after surgery can be even more about self-discovery, with implications that can be transformative.


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Isabel* is 32 years old
I knew the surgery was what I wanted from a young age, and I was excited to start the post-op stage. I had never enjoyed sex before because I didn’t like being treated like a boy, which is inevitable if you are naked and have a penis. I was a pretty boy and was popular with the girls, which often led to sexual experiences that left me with immense guilt. I always knew that without a penis this guilt would not exist.

My first date after surgery was with this beautiful girl. She looked like a girl out of my dreams; blonde with short hair, piercing blue eyes, and eyeliner thicker than Amy Winehouse. We sat in a quaint 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 being labeled. It felt like an honest exchange between two people who were coming to terms with their identity. So I invited her to my home, not sure what to expect.


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After I poured us more wine, we started touching each other without any warning. She was very aggressive with me, tearing my clothes, pushing me onto uncomfortable surfaces and rubbing my clit too hard. I was so shocked with her sudden change in behavior that I let it go on for a few minutes before asking her what the fuck she was doing. She apologized and said she didn’t know what I liked and encouraged me to continue exploring with her. She said she would slow down. I was so hungry for the experience that I ignored the warning signs my body was giving me.


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We drank some more wine and started gently touching each other for a while, which was nice. It was nice to be touched by someone in the places you’ve imagined for so long. Then he gave me oral sex, but it wasn’t considerate or gentle, it was rough and excessive, as if he was simply trying to make me wet just for the sake of doing it. He pulled a harness dildo out of his bag and before I had time to comprehend what was about to happen, he was fucking me hard and viciously. I felt really empty. I didn’t resist, because at the time, I thought it was my fault-that I had made a mistake with my own identity. I lay there wondering if I was really a woman or not-did I live through all this pain for nothing? Did it really feel like that?


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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 like I couldn’t trust my instincts anymore. I started to cry. She saw my tears and stopped, pulled her harnessed dildo out from inside me and said, “I thought that’s what you wanted.” Then she put her clothes back on and left, without anything resembling a hug or a goodbye. It is an experience I will never forget. In the months that followed, I didn’t feel confident to have sex with anyone.