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Have been watching that sort of porn for years, knew it turned me on, but never had fantasies about it. A few years back, after a difficult time of my life, I was in a pretty bad place and started having fantasies about it for the first time. It was odd because I was certain I had zero attraction towards Males, especially if they looked at all like males, it was just cocks. Wasn’t really sure what to do about it, but the idea of being with a transgender woman really turned me on. Experiencing it for real was something that nagged at me for months until eventually I took the leap. Organised to meet up with a prostitute through an online escort hire site.

I specifically wanted to suck a cock, so had been practicing with dildos for months before taking the plunge, and I had also done a lot more experimenting with ass-play and even double-insertion to mentally prepare myself, though I was quite certain I wasn’t wanting that from a real experience (given my sexuality).

The first time, it was quite bad, the escort was not who I had been led to believe they were (misleading photos), they had done nothing to prepare for the visit, no makeup, no outfit, weren’t available on time, lots of complications with contacting them for the room number. Once I finally got to the room, it was also dark and untidy. I Was kicking myself, questioning what the hell I was doing there, but I was there and I had the money (she even overcharged me) but I ignored my conscience and went through with it anyway.

The second time was admittedly a lot better as far as an “experience” goes. They were dressed up, on-time, very polite and accommodating, the room was very neat and had a nice mood, even the act itself was a lot more pleasant and enjoyable.

I’ve never been able to talk about this before, and so I’d love to be able to just discuss it with anyone here in detail.

NSFW: yes

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