Everyone has a type that just does it for them.
For me there's nothing that gets my space shuttle to the launch pad faster than a younger submissive gay bottom. I'm not personally into crossdressing or feminisation though I do enjoy porn along those themes. And I always figured that if you want to be with a girl you can always be with actual girls.
This was just silly of me and I had no idea what I was missing until I met Kerstin.
We met during a work trip of mine to another city. I didn't know anyone in town and so I went to the hotel bar. Sat down and ordered a drink. Wasn't looking for a date or anything after a long flight and exhausting day. It was then that I saw her enter the bar and she saw me. Without batting an eyelid she came straight over to my table and asked if she could join me. I realised that she was a he, though you wouldn't be able to tell from across the room, and was intrigued. She was staying at the same hotel in town for a business owners' convention. And she was an energy sector consultant who had founded her own company.
Over drinks conversation went smoothly. Turned out she had been married and only made the change five years ago. She was older than me and had decided to undergo transition. Part of that was living as a woman, taking a bunch of pills every day, and therapy. It really struck me how open she was and at ease with being vulnerable. That's the opposite of me. I'm a typical guy that way. Takes me time to open up. And even then I'm not particularly talkative. I show how I feel through my actions more than my words. I am more than happy to listen and I really enjoyed Kerstin's company.
It didn't immediately come up that I was gay and a top and I figured she was just trying to feel comfortable interacting with a man at a bar in a city she was new to. But she was quite happy with it when I did tell her. It turned out that we were both going to be in town for the next 4 days. We exchanged numbers and said goodnight and went to our respective rooms.
I did find Kerstin attractive. She was 5 feet 8 inches, neither skinny nor fat, nice sharp features. But what really hit the spot with me was her voice. It wasn't fully a woman's voice but sounded very inviting. I imagined the sounds she would make if I fucked her and it was to such thoughts that I fell to sleep.
When I woke up the next morning I saw that I had received a voice note from her. She wanted to meet up for drinks and dinner. I was happy to say yes and let her pick the place.
We went to this really nice Italian place where you could sit outside in the back garden. And we sat in the corner. I was wearing a dark grey bespoke suit with a white shirt, blue tie, and pink pocket square. And she was in a black corporate pant suit. We continued from where we left off - she did 75% of the talking and I was by this time quite taken with her. Her voice was entrancing.
After a great dinner with lots of wine we headed back to the hotel. She invited me to her room for a cup of coffee or "any other nightcap" I might like. I don't have the best antennae but was pretty sure that that was a come on.
