Transvestites

[TwilightLord]

I've never crossdressed, but I'd probably be good at it. I have a very feminine build and (usually) have long hair.
My ultimate dream is to have a completely androgynous look - I want to basically be someone who people look at and think "Wait, is that a guy or a girl?" and be completely unable to tell until I gave it away by talking or something (one thing I sadly can't make androgynous is my voice). Sadly my girlfriend would never approve... Though she also says I'm very feminine, in attitude as well as appearance.
I probably wouldn't crossdress since I'd be too embarrassed, though. Though I did do this Captain Twilight Lord to You by ~Jutah on deviantART for Halloween this year. (More pictures in my gallery). It's not crossdressing, but it's the closest I've ever come to it (i.e. the makeup).

[demondude]

Dude(ette?), we have the same scarf. Cool.

I think androgyny is really interesting, especially in an artistic way. You had it down pretty well there.

[Mirage]

Oh yeah, I forgot to add something to the actual topic

I've crossdressed once and I thought it was exciting. I actually felt a bit awkward when I saw how cute my face was with makeup and pigtails. I'd do it again, but I'm not very good at applying makeup. A girl helped me do it the first time. Also, my body shape isn't very crosscress-friendly, though it could have been worse.

I don't know if I would feel more comfortable in girls or guys clothes (mostly because I don't have a lot of experience with one of those), but I do know that I would love for both to be equal options for everyone.

[Peegee]

I'm reminded of that eoeo thread I posted in that one time...

[Tigmafuzz]

The only time I ever cross-dressed was when my partner at the time thought it would be sexy. And usually... It was.

[Pike]

I would love for both to be equal options for everyone.

Me too! It seems so unfair that girls can dress up like guys most of the time and no one really cares but guys can't dress like girls can.

[NorthernChaosGod]

I don't know about you guys, but I like my guy clothes.

[Tigmafuzz]

I don't know about you guys, but I like my guy clothes.

You have no idea what you're missing.

[Mirage]

I don't know about you guys, but I like my guy clothes.

Of course you do, it's probably the only thing you know. And even if it wasn't, social norms will prevent many from thinking they like it.

[NorthernChaosGod]

I've worn a skirt before, pass.

[Mirage]

What if you had been wearing a skirt for the entirity of your life, and then tried on a pair of pants? I'm sure you'd find that weird too.

[NorthernChaosGod]

Doubt it, pants have more utility.

[Tigmafuzz]

Wearing a miniskirt is very liberating. I wore a dress for Halloween, btw.

[NorthernChaosGod]

Did you shave your legs?

[Tigmafuzz]

Yup. They were really shiny. I never realized my legs were so pasty, though; the hair always made them look darker.