[Sofia Bunny]

Well, I'll answer anyway. ;-)

I hope my long-winded response hasn't been too much. :-)

-Dianna

Wow Dianna, you said a mouthful! Thank you very much for your insight. It was long, but appreciated. I don't think I am ready for any large group encounters. I am just not comfortable with that idea. As for bars and such, I'm not much of a social butterfly. It takes a quite a bit of effort for me to open up and be social. Sure, here it's easy, but in person, I am way too shy, and passive.

As for any involvement with my wife, that's not going to happen. She is a bit on the conservative side. I joke with her about wearing women's clothes now and again just because her clothes fit me, and she gets pretty negatively vocal about it. She does not appreciate it one bit.

So for me the idea of transitioning is REALLY far fetched. Parents that would disown me, a wife that would probably leave me, just doesn't seem like the right thing for me. There just really isn't an easy answer, I will have to settle for what I can get. How far I am willing to go to get what I want varies.

Yeah - did the same with my family over the last 20 years.
Never went well.
:-P

-D

My parents are pretty darn close minded. There is no understanding of this. There is no grey, there is no middle. There is no Bi, you're just gay. Transitioning, I would be a freak to them. I would be abnormal. I hear the way they talk, and gossip, and it drives me nuts. I have no idea how I turned out to be so different considering what I grew up with.

This sounds a little more... complex, then.
It might make sense to look for a professional domme to talk to, and trolling the "sissy" blogs might help, too. The idea being, find a lugubrious sissy-type or woman who has some "flexibility" in her outlook, and warmth towards the unusual.
It's NOT suggesting a sexual or "professional" encounter, though. Just a discussion with someone who could be trusted a bit, and provide some insight. Then from there, maybe a gay club on Drag night? Be the quiet guy in the background, say, and talk to the queens now and then, to get yourself some socialization. And then, plan and proceed as appropriate.

I'd think it's no different from going to a strip club to ogle the women. You won't be going home with them, but you might get to chat with them a bit, on a good night. And you could certainly bring the wife along for the spectacle, and to get her opinions and feelings afterwards (I.E., make her included and play to her feelings/needs for security and safety.)

-Dianna

Not many drag places where I live, though there are gay bars. Went once long ago with friends, but I am just too socially awkward. I'm already submissive enough, I am not sure visiting with a domme is going to do me much good. Plus I'm sure the Mrs. would not like that one bit!

I have found that the best laid out plans are bound to go to hell in a hand basket, so I don't bother. I mostly wing it and let the chips land where they may. Also in my case most of the time it is better to ask for forgiveness than permission.