Nicole, I'm afraid I have no practical advice to offer from personal experience. I've never had (nor sought out) an encounter of this kind, though I concur with the advice of others regarding personal safety especially.
I do appreciate the obstacles in your way, because they would apply to me as well. I'd be concerned about health issues as well as the risk of violence. Then I wouldn't be sure how to go about finding a suitable partner, plus, being married, I wouldn't want to cheat on my wife anyway. Apart from all that, I've never wanted "gay" sex in the first place.
However, I can identify with what you said about wanting to experience sex in the role of a woman. That's different from being "gay," because it's about the role in which we imagine ourselves during sex, as distinct from the partner we imagine ourselves with. So from the time I started crossdressing, some of my own fantasies ran toward "lesbian" encounters.
That's one place where it's necessary to distinguish between fantasy and reality, as others have pointed out. There's a mental exercise here. If I imagine sex from the viewpoint of an onlooker, a third party, it's only attractive to me if the scenario has a woman in it. Normally of course that means sex between a man and a woman, and for this reason alone I could see the appeal of actually being the woman in such an encounter with a man. However, the idea of sex between two men does absolutely nothing for me, So if you're looking for a sexual experience with a man, then as Stevie said:
And maybe it isn't "gay" sex, not in your mind. It's "TRANSex"! But what happens when the skirt comes off, and a lot of other clothes too? If female clothing is an indispensable prop to imagining oneself as a woman, then if you end up naked in bed with a man, it seems to me the illusion of femininity and "transex" would pop like a bubble, and "gay sex" is what you'd be having.Originally Posted by LilSissyStevie
If that still floats your boat, then that's fine, but it is a point to consider when weighing fantasy against reality before seeking such an experience. You've used the term "gay" yourself, so if you think you'd be content with an encounter you accept is "gay," that's fine. You mentioned previous encounters with "girls," which I took to be T-girls, though I don't know what exactly a "minor gay encounter" entails! I can only hazard a guess, but this may seem different from sex with a male who's presenting as a man.
Apart from that, sex, like any experience, involves all of the senses--sight, hearing, touch, taste, smell, and all kinds of behaviors. That's where fantasy can collide with reality. In fantasy we can make things happen any way we want to. In reality we have to deal with everything we perceive with all of our senses, and with whatever a partner chooses to do with us. So while I can imagine in limited ways how sex as a woman might be exciting with a man, I've always thought that if I ever tried it, too many extraneous elements would simply repel me.
It's just something to think about realistically, including what "kind" of sex you're looking for, or might end up with. Of course, "your mileage may vary," so if after thinking it through thoroughly you're still irresistibly tempted, I admit the only way to find out is to try it out for yourself. Good luck anyway, whatever you do.
