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True Life: My First Date with a Transwoman

Couple in Sunset

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 TSmeet.com 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.

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Tell us what you think! 3 Comments

  1. Lexie

    October 5, 2014 at 9:13 am

    Thank Goodness for Men like Bill who is in my opinion a real Man, a Man who knows that Bella is a Woman and as much a Woman as any so-called natural born Woman we just can not have children but there are many natural born Women who can not have children either. I am a pre-op Woman but I see myself as a Woman and only a Woman. I may not have the finances for GRS/SRS or facial feminazation surgery but I am no less a Woman. We need more Men like Bill………………Bill I give you two thumbs up and a great big Bravo.

  2. andrew winston

    October 7, 2014 at 8:40 am

    That’s a great comment… shows love and respect for each other. That’s a good feeling to love someone and to feel love back.

  3. knight4444

    October 16, 2014 at 5:51 pm

    Good for Bella and Bill, unfortunately the vast majority of TS people I’ve talked to or dated were pathological liars, and the number 1 victim of their lies were themselves. MEMO to some transgender women: don’t date ANYONE until you’ve got your head on straight!! If you can’t be honest with yourself, how the hell can you be honest with anyone else?

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