general Have you ever tried clothes for the opposite gender?

[vivishy 1,032]

i love wearing men's shirts because they are so much more loose and comfortable

[Chacobos 160]

I am a bit jelly of how women's underwear is more comfortable than men's underwear. I do find stockings also comfy but that's a different story. 

[Caliboom 219]

When I was younger, I did, for Halloween.

 

I regret doing that, everyone made fun of me.

[ShadowFoxz 342]

If someone wants to be my mentor to lead me into cross-dressing... I wouldn't mind... don't judge me!

I wouldn't mind passing my wisdom although I don't do it anymore

[CharlotteR-MLP 50]

I really wish I could do this.

[n0body555 334]

Yes I have

 

I have mixed opinions on it... It's fun but not so sure about doing it a lot.

[Guest]

Kinda sucks that girls have some really dope stuff, but I can't fit any of it. So no xD

[Simcity11100 772]

Yeah, all the time, just not in public cause I just don't want to, though I don't think anyone would care anyways, I mean I've done it in school a bunch of times and the only time people noticed was at the end of the school year, so yeah.

[Starlighty 939]

I actually buy guy shirts that have like video game or movie because they don't sell the one I like in the girl section. 

 

I also bought guys shoes because girl shoes that I find are just ugly... they make them so girly or pointy and BLAH its just not right 

[Gaviera 52]

Fuck yeah, went to class with 'em on too. Fun day.

[cuteycindyhoney 13,306]

Boxers are really comfy to sleep in.

[MrMammal 157]

Sure have. I've tried on a dress, skirt, cheerleader outfit... lots of things haha

[Snake 516]

I have! And judging by how my friends reacted, I'd make a hot guy! I felt pretty confident too!
Though, I enjoy being a girl, but dressing as a boy is fun too!

[chirox the pony 1,336]

No I don't believe I have, I've just never cared much about clothes period so I never tried it out, didn't know it was this common though.

 

P.S Wow what a weird 1000th post.

[Alex Z 848]

Nope, I have never worn any women's clothing.

[Vox 870]

When i was 3 i bounced around on a trampoline wearing my friend's dress if that counts 

[FlowerHearts 66]

i have many times. it is nice to dress like a male. one halloween i went as John Lennon.

[Nerdy Luigi 2,065]

Technically I wear clothing for the opposite gender all the time. That's because society accepts me as a man, but not a woman. Which, for obvious reasons, sucks for me.

Edited August 16, 2015 by TwillyFSniper

[Hypn0ticD 1,213]

I have! As a matter of fact, I own more than a few pairs of men's pants, because like someone said earlier in this thread, they're more comfortable and have REAL pockets!

[Quill Waver 1,408]

Why yes, I have! I do it quite often! I just LOVE to crossdress! . Most of the time, I wear panties and thigh-high stockings under my normal clothes, and I love them. Sometimes, when I'm home alone or if it's late at night, I wear a skirt or a dress

I almost want to see what that would look like. ALMOST! 

 

I myself did try on some gold, two-tone stockings one night... and I had a friend who was in college hosting a costume party who had to wear a French maid outfit. I totally did not steal his Agent 47 outfit and switch it.

 

No. Never.

[Elanau 23]

Yes.. boy clothes are much more comfortable than lame girl clothes.. though I still dress up a little girly from time to time..

[nevergrowingup 28]

I had shirts for guys, but even if they were XS, they were too big on me -sigh- and I'm not allowed to go anywhere by myself and I'm scared I'll get yelled at if I buy guys clothes.

[MLPFanatic34 3,234]

I'm a girl and I wear boys clothes often mainly because they're comfortable and I'm a tomboy, I don't see anything wrong with it either lol 

[Derpy Muffins 79]

When I was 4 I had a pair of Sketchers light-up shoes that were for boys if that counts, also I have a Pokèmon shirt that is meant for boys.

When I was 4 I had a pair of Sketchers light-up shoes that were for boys if that counts, also I have a Pokèmon shirt that is meant for boys.

Also I wear alot of boys clothes 'cause I'm a tom-boy and don't care for dresses.

[RattPitt 172]

I've worn high heels out of curiosity. I have one question for all of the ladies that have worn them: How the hell do you not break your ankles wearing those things?