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My First Experience with a Transgender Woman

by Jeff Watson 4 months ago in lgbtq

I was surprised, but not dissuaded.

Image by Tom Morris

The first time I was with a transgender woman was, well, completely by accident. But that accident proved to be quite memorable and opened up my world in a whole new way.

On occasion I would go out and look for someone on the street (okay, a prostitute) who I could get some sexual relief with. So, I was wandering around the area of town where sex work is done, and saw a woman who I thought was quite attractive, with long blond hair and a pretty face. I remember her short, tight red skirt and her exposed legs, which were big turn-ons for me. It was a bit chilly outside, so she wore a short jacket that didn’t obstruct any views of her body. She was a shyer lady, or somewhat distant, I suppose. She walked a ways in front of me, not speaking to me as we headed to a room in a rundown apartment building that she rented for the purposes of bringing clients to. Interestingly enough, it was marked by a red light on in the front stairway, a mini red light district of sorts.

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The room was dark and pretty barebones. Just a light and a bed. It was clear it was for one purpose and one purpose only. But I loved these kinds of dingy old places. It added to the excitement of it all. It felt a bit scary, the temperature was cool in there, but it was also inviting. I suppose knowing what was about to happen made it appealing as well. It made it seem that much more illicit and that much more exciting.

I lay down on the bed, and our session began. She climbed on, straddling my legs, taking my cock in her hand which was rather cold from the air outside but still soft. She began to stroke in silence, and it felt good, and I was warming up. And then, kneeling at my feet on the bed, she pulled up that sexy tight red skirt that I loved so much with her other hand, showing me that underneath her nylons was her own cock. It was a thick, cut cock with dark hairs around it, the same length as mine but with more weight and girth.

I was rather floored. This woman looked like, well, a woman born with female genitalia. I’m aware that isn’t politically correct to say, but I don’t know how else to say it. But boy was I wrong. At first, it turned me off a wee bit—just a wee bit, though. It wasn’t what I was expecting and I wasn’t sure what to make of it all, seeing as this was the first time this had happened. I didn’t want it to stop and I definitely didn’t want to say anything to offend her, but for a moment I was a bit shaken. I wanted what we were doing to continue. I wasn’t against it. I just wasn’t expecting this twist.

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I don’t know if she knew that I didn’t know she was transgender. I don’t know if she showed me her cock to see the response, or because she thought I was out searching specifically for a transgender woman. Regardless, this was the situation I found myself in, and in the end, it really didn’t matter. I was still having a lovely sexual experience with this attractive person. It felt good, and her pleasant work led to me cumming. So, clearly, the revelation didn’t change the fact that I left sexually satisfied. I enjoyed the experience.

It’s not that I was necessarily opposed to being with someone who was transgender. In fact, recently, I had gotten to know a girl who was transgender who I confess I rather liked. And I got the sense that she liked me, though I tend to be bad at picking up on these things.

I had considered asking her if she wanted to go for coffee. I was curious and somewhat sexually attracted to her. But, I admit that I was cowardly. I was scared partly because I was afraid of how people would react to me being romantically involved with someone who was transgender. This was many years ago when transgender was still rather taboo, not talked about nor understood. Today, there is far more understanding and more visibility. But then? No. It wasn’t understood or really accepted.

But, I digress. The main point is that I had a mind opening, enjoyable encounter I never expected to have. When we were all finished and redressed, we left the dim room, out the red lit front door and went our separate ways. But, how can I forget the first transgender woman I was with?

Jeff Watson
Jeff Watson
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Jeff Watson

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