I'm 66, single, and not in a relationship. It's certainly not from lack of trying. But I have noticed that when on dating sites, and seeing some possibilities - even communicating with potentials....I find myself getting cold feet, and backing away. And it's my belief that it's primarily due to the fact that I crossdress. I think about how being in a relationship would affect that part of my life. Because believe me, it's not something I will ever give up. I would neither want to - nor, I think, even be able to. I'm sure there are many of us who have certainly tried, myself included.
The last relationship I was in, the lady never knew about my dressing. She strongly suspected "something", as I shave my legs, which she thought was strange. I gave the excuse that I simply disliked hairy legs (which I do, anyway) My original marriage was also a situation where I felt telling my wife at the time about my crossdressing would be a disaster. So I never did.
So, it's something that I worry about. And it's not like I have a lot of opportunity to meet women. My biggest concern would be finding someone, and telling her about my crossdressing, only to have her reject me....and worse, tell people I know in retaliation or spite. I still work full time, and it would be a disaster for me if any of my associates at work ever found out. Or anyone in my personal life. The only person that knows about my dressing is my daughter. She's accepting and supportive, but has never seen me dressed and doesn't want to. I'm of course closeted and never go out.
Having been single for 10 years, I have been able to indulge in my dressing any time I want to. And working full time also allows me to buy my female clothing and not have to hide it or worry about anyone finding it. I enjoy this freedom.
So I find it a bit of a conundrum. I know that I will receive replies saying that I should go for it, and worry about whether to divulge my secret at a later date. But would that be fair to someone with whom I have entered into a relationship? If I tell her too soon, then I risk retaliation in the form of being outed, and if I would tell her too late, when a strong relationship has been formed, then that is not fair to her if crossdressing is something she could never accept.
I have read positive stories from those of us on here, who have told their wives/partners and had good results. But occasionally I will read about those who have had the opposite. I really don't want to find myself experiencing the latter.
As a result, I find myself wanting a relationship, yet finding excuses not to enter into one. As it stands, I have met quite a few women over the last few years, all of whom were either not suitable, or they felt I was not the right person for them.
So, this is something that I would direct to those of us on here NOT in a relationship at present, perhaps looking for one, and maybe have had similar experiences. How do you deal with this? Anyway, thanks for reading....I really just needed to vent a little.