Confronting thoughts

What did crossdressing boys and men expected and hope for?

I didn’t think about it as a younger man just enjoyed crossdressing never thought of involving anyone else or a girlfriend or wife needing to know back then, it just felt nice to wear silky lacy lingerie and it was a massive turn on.

Did we grow up believing most women liked crossdressers and never knew it would be an issue?

Again this never ever crossed my mind when I was younger Crossdressing, although I knew it would be frowned upon so hid it bearing in mind it was my Mums lingerie etc I was trying on. (sounds aweful now).

I just never put 2 and 2 together and thought much about what would happen with crossdressing into the future as I got older, met a Girlfriend and got married apart from back then part of my reason to dress was I didn’t have a Girlfriend and it was a bit of a sexy kink wearing things I wanted a girlfriend to wear to a proven point when I met my first real girlfriend who is now my wife my crossdressing stopped and only started again due to some stressful issues and part of my dressing again now is this compensation where my wife only rarely wears tights, stockings heels etc so in steps Davina in to 4 inch high heels to compensate lol.

Did we always know it would one day cause  us problems with women?

I had no idea I’d still be crossdressing at 30-40 and dressing fully as a woman with makeup and a wig trying to look convincing so never gave it a thought that crossdressing may cause problems with women or my wife for that matter.