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Crossdressers! THREAD AHOY!

Started by redeker, March 12, 2010, 05:17:56 PM

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redeker

First off, I'm going to admit that I'm not really a crossdresser much. I did experiment a few years back, and I do  like it (yes, present tense; I still do), but I've grown somewhat detached from it, as it became harder to hide my little fetish.

So, anyway: to anyone who is or has tried crossdressing (defined as the wearing clothes for designated for the opposite gender), what clothing did you wear in your first crossdressing experience?

For me, my first clothing were some cute string panties with a ice-skating-penguin pattern that got mixed up in my laundry when I was 15 or 16. And I have to admit, I was pretty surprised at how comfortable they were. 
All the crazy monkeys
are playing a game that will never end,
caught up in a never-ending "Banana Roulette."

Iku Nagae

#1
Well I do do a little crossdressing. I first tried on some old dresses that were being thrown out by my sisters and my mother, because we had to move far away and couldn't take many things with us. So in this huge pile of trash, I was secretly going through picking up stuff of mine I didn't want thrown away. Found a few dresses and thought to myself, "So this is what one looks like. I wonder what it feels like." So later that night I tried on one and surprisingly it felt pretty good.
Now I just wear some panties, very comfortable, and my costume I am going to use for cosplaying. Of course its a women's character I'm going to cosplay as. *points to my avatar*

Flyper

I've been somewhat interested in crossdressing for as long as I had a sex drive. I wear pantyhose or tights whenever it's cool enough. It's gotten to the point that I don't consider this to be crossdressing. I know from experience (wearing them with shorts in public a few times) that the general public doesn't share this opinion, so I expect others' opinions to be different from mine when it comes to that subject.

My first experience in which I was fully crossdressed involved wearing one of the dresses that my grandmother packed away in a closet in my room. I liked the feeling that I got from wearing it.  From then on, I would periodically wear these dresses with some pantyhose I stole from her dresser and a few pair of heels that she had packed away as well.  It was a nice experience, but I'm not obsessed with it. I haven't worn a dress since I was 16 and I don't have any desire to do so in the near future.

Also, when I'm not wearing pantyhose, I wear panties instead of boxers. I mostly do this because I like the feeling I can't get from wearing boxers; however, I do admit that if men's underwear were as silky as women's underwear, I would still have a pair or two of panties. :lol:

Mighty Oracle

I think it's completely unappealing. >_>

Sarrim

Done it for fun, cause I'm in Rocky. Not really a thing for me though.