I'd gotten intrigued by two factors: first was a great S&M gal including a little strap-on action in our first meet. (I later went back to her strictly for GFE.) It mostly felt awkward and uncomfortable at the time, but I think a mental seed was planted.
It was months or years later when I started getting into TS porn. The first video was a simple thing, a gorgeous, bodacious woman sitting and stroking a big, hard cock. It was a moment when I got kind of addicted to the whole scene.
Again, it was months or years later before I took the plunge to see a local TS lady. She was tall, busty, just a bit above average in endowment. She was enthusiastic starting off intensely GFE. When things proceeded to me giving her a bbj, it was odd, but pleasant. She was not as I recall one of these aggressive throat fucking types. Later on, she lubed me up, put on the condom, and started fucking my ass. I couldn't believe that I was doing that! That's really my dominant reaction - thoughts along the lines of "What The Actual Fuck Am I Doing???" it was a mix of 1/3rd uncomfortable, 1/3rd painful, 1/3rd an intense sexual turn-on.
Slowly, over the years, I've turned into a rather cock hungry bottom whore.