Told my oldest friend

[tvmelissa]

So, I went to visit my oldest friend yesterday and, while I was there, told him that I've been crossdressing since I was a kid. We've been friends basically all our lives, since our moms were friends.

Since it was the first time we'd seen each other since the summer, I started out by asking him if he did anything for Halloween this year, and went on to say that I hadn't this year, but had I ever shown him the pictures from 2 years ago? (Which, of course, I hadn't...) That was the year I went to work as "The Lady in Red", using the old "lost a bet" line, and since I was going to "have to" wear a dress, I might as well go all the way. And it wasn't just any red dress, but a gorgeous, Lauren Ralph Lauren full-length evening gown, with a side-slit up past the knee. It cost way too much money, but when I saw it, I just had to have it. :daydreaming:

He was surprised, but totally accepting. It didn't even really faze him when I said that I was wearing a bra, panties and pantyhose under my T-shirt and khakis, as I had been for some of our other get-togethers, and even to university (we independently chose the same program, at the same school!).

In the past, I'd thought of surprising him by dressing one day when he was coming over to my place, but I never did. Now that I've told him, and he seems cool with it, I'm more seriously considering it for next time...

Melissa

[DIANEF]

I suppose a lot of guys have 'dressed up' as a one-off, but being a regular CDer is something different. Maybe you should just tell him you CD rather than suprising him with your femme self and see what his reaction is. If positive then show him your girl look. Obviously you know the guy well so it's your choice but he seems pretty ok about the CD thing.

[Judy-Somthing]

I had one close friend I would show him dresses I bought and photos of me quite often.
It was nice to have someone to shear my secret with.

Then when in my 40's I started thinking he never shared any thing personal about himself.

Well one day I was showing him a dress I bought he said that I was "very weird".

After that I never talked about it any more and a few years later I told him I grew out of it.

[Territx]

Melissa -- I agree with Diane. You should probably take small steps, maybe even wait to see if he brings it up again any time soon, to gauge his feelings. It is very uplifting to find a friend to talk to about crossdressing, but it can be painful to have the issue come between friends. If he hasn't mentioned in after a while, you might broach the subject again by asking how he feels about the subject now that he has had some time to think about it. Just my 2-cents and probably not worth that amount.

[tvmelissa]

My friend sent me an email today thanking me for trusting him enough to share this with him, and that it doesn't make a difference to him.

I've asked him how he'd feel about me dressing sometimes when he comes over, letting him know that I understand if he's OK with knowing I dress, but would be uncomfortable seeing me dressed in person.