Crossdressing - a different twist

[Sally]

When I was 19 I had been going with the girl who was my first love for about 12 months and at the stage I'm talking about, we were touring around interstate on a weeks holiday together.

The last night before we went home we were staying in a hotel for the night and the events of that night have always and always will be vivid in my memory.
I was laying on the bed after dinner reading a book when she asked out of the blue if I'd ever dressed up in girls clothes. Why she asked this I really don't know to this day, but later I'll comment on my thoughts as to why she possibly may have had it in her mind.
When I told her no, (huge lie) she said that she wanted to make up my face and dress me up in her clothes.
I will always remember that I suddenly became angry, as if hurt, even embarrassed, and told her there was no way she would ever do that to me. The evening went a bit flat after that and to cut a long story short it wasn't long after that, that she broke off our relationship and moved on.

I've thought about that night many times over the years and so many times I've wished that I had let her have her way, but at that time in my life I was having a very hard struggle with my gender identity and during my late teens was probably the worst time in my life as so many times I thought of ending it all and a couple of times came so close. I't's amazing to me that I could have said no to something which was such an integral part of me.

Maybe if I'd gone along with her wishes life would have taken another right angle turn for me but I'll never know. Maybe she was the person who could have turned my life around at that time, whereby I may have avoided years of heartache and distress, but once again I'll never know that.

I've often thought that maybe she was perceptive in that she read something about me which led her to believe I wasn't the same within as I appeared on the outside. She would possibly have picked up on some things about me during moments of intimacy which may well be more attributed to females than males and I've often thought that it's possible that she was trying to tell me how she thought regarding men with female tendencies, but possibly she was just as afraid of me knowing how she felt as I was about her knowing how I felt.

I've come to believe that there are more women about who are receptive of the idea than we may first believe. My wife is always a shining example of what I'm talking about because the reason why I never told her before we were married, is that I believed with her upbringing and knowing her as the type of person she was or I thought she was, I was afraid that if she knew then she would not be able to live with it and she'd leave me. Well as people know and I've said it before, when I eventualy told her, the first thing she said was what a fool I was for keeping it secret and missing out on all those years of not being myself and enjoying life fuller.

Kind Regards,

Sally.

[RobynP]

While in high school I had one 'steady' girlfriend who was always suggesting to me that I wear a dress or she wanted to make up my face. I was so deep in the closet then I could not and would not accept any of her suggestions. (She and I were two completely different sizes as well... ) I had to be "macho" about the whole thing...

She ended up marrying a guy who ended up becoming a post-op TS. Her second husband AFAIK is not in any way TV/CD/TG/TS...

I used to wonder what would have happened if we had stayed together and gotten married...

I guess the moral of the story is be careful what you wish for because you just might get it!!!

Robyn P.

[Jaye]

Before I got married, I went through a short succession of girlfriends who knew of, and accepted my crossdressing. I opened up to a couple of those after being prompted to dress up for bedroom roleplay, and they were pretty cool about it. The last one actually liked to go out with me, dressed up. I should have married her. Oh, well...

A male friend of mine confided that an ex of his had asked him to dress up once, but he broke it off when she tried to make it a "regular thing". He knows I dress, and is okay with that, but says he'd never do it himself.