Realization vs. Reality

It was the damned internet. Shemale porn everywhere. And while the majority of the images inspire no lascivious thoughts in me, I cannot help myself from seeking them out. And every once in a while I am rewarded by the image of a gorgeous woman with great tits, fine ass, and a big hard cock.

So I fantasize, and jack my dick to thoughts of one of these gorgeous lady/boys dominating me and making me suck her cock. I have even bought dildos and fucked myself in my virgin ass to thoughts of being taken by a beautiful shemale.

I have at times thought to act on my obsession, but porn, the occasional 1-900 number, and chat rooms are as far as I was able to take it.

That is until I met Jamie.

Okay, about me. I am 6’3” tall and weigh about 250lbs. Because of my height, I carry the weight well. I am not ripped, but neither am I a slob. I work in construction, and am in pretty good shape considering my eating habits. I am average looking. The kind of guy some women think is handsome, and some wouldn’t spit on if my head was on fire. As far as my “manhood”. I guess it is right for my size. I don’t know how long it is exactly, but I have never been embarrassed to take my clothes off in front of others. And if what I have seen in locker rooms is any indication, I’m pretty well off.

My job takes me out of town a lot, hence the poor eating habits. But the travel affords me the opportunity to experience a lot that I would never have the opportunity to otherwise. I am divorced, with no children, so I am not really tied to anyone or anything, so I am able to “play” when I am out of town.

I have gotten the art of seducing younger women down to a science almost. And I have enjoyed the company of more than a few during my travels. Sex isn’t always, or even usually the result of these indulgences, but it happens often enough to keep me happy.


Now the story.

I was working in New York. About an hour away from Manhattan. I was going to be there for about four months. Being that close to the city, I had the opportunity to go there on the weekends once or twice. I considered going to a club where I might actually meet a real shemale, or even hiring a tranny escort, just to have the experience. But I chickened out each time. I had fun in New York though, even got laid once.