True Life: My First Date with a Transwoman

This story comes from reader Bill, in California:

I met Bella at a friend’s party last winter. There was something I really liked about her right away. She had a great confidence about her, and a special twinkle in her eye. I got her number and asked her out shortly after the party. We went out one time and I could tell she was nervous. We were just having coffee. She was so nervous that I even asked her if she was okay. She looked up shyly from her cup and started to say that she had something to tell me, something that might make me not want to go out with her again.

I consider myself a pretty open-minded person, so I told her to just go ahead. When she told me she was trans, I laughed and literally said “Oh is that all it is?” It’s probably one of the things that subconsciously drew me to her in the first place, as I’ve always kind of had a thing for trans women. Of course, then I asked her a few awkward questions about the mechanics of her situation. I felt a little strange doing this, so I told her she didn’t have to answer at that moment, but if we ever decided to get intimate, we should chat about it first. I realize now that asking her about what’s under her trunk was a bit of a faux pas, in fact kind of rude.

Things You Never Want to Say to a Transexual

I am so lucky that Bella was so understanding of my curiosity and fascination about her, because now we have been together for nearly a year. She has been so open with me about her situation and history. I don’t really even see her as a “transwoman” anymore, I really just see her as a beautiful and sexy woman who I’m falling more in love with every day.

One thing to keep in mind is that transgender women are still a very rare find offline at parties, so when friends of mine have asked me to help find them a hookup I always mention as the best place to start looking. Bella and I are on there from time to time because we’re polyamorous, and the community vibe is terrific.

Tips for New Online Daters

Tell us what you think

Notify of
Inline Feedbacks
View all comments