Have you ever cross dressed?

Not since I was a young child, and my sisters had fun at my expense.

When I was in junior high, I would wear men’s ties. I own boxers. So, yeah. I have cross dressed.

Yeah, I have. I still do, occasionally.
Boys jeans, jackets, sometimes trainers…

If jeans, a sweat shirt ,and sneakers count. I never tried to really look like a male. i enjoy being female.

It’s funny men are cross dressing if they wear women’s clothes, but when women wear guy sneakers (love my Chuck T’s), guy’s jeans or shirts it doesn’t mean anything.

All the time.
I wear dresses, stilettos, lipstick, nylons, what have you, and set for the town center, but every time people unmask me within seconds.
Maybe the beard is a giveaway?

Ha! The beard would most likely do it, yep!! :)

Yes, I constantly wear human clothes.

I haven’t but I would love to pull a Marlene Dietrich one day. Sexy.

When I was a freshman at college I was at the Salvation Army looking for a costume for a “Pimps and Prostitutes” party at my fraternity. I was with one of the “old guys”, and he found a mini-skirt dress for a dollar, and said I should wear it. I found some size 12 high heels, some fishnets, a boa, and a cigarette holder, and bought it all.

The guy’s girlfriend helped me dress, and I walked into the party like I was walking onto a yacht. Every girl at the party wanted to have a picture taken with me, it was a lot of fun.

But it’s not my thing, so that was the last time.

Closest I got was a toga on Halloween.

“I walked into the party like I was walking onto a yacht”
:) Nice.

At a party with the theme of come dressed as the opposite sex. It was a Halloween party and I won ” Best dressed man.” lol

I borrowed a neighbors hardhat, work boots and tool belt and stuffed a flannel shirt with a big belly and a roll of socks down my jeans.
I am blonde and put my hair up in a bun under the hardhat and found this perfect blonde moustache that looked great under a fake rubber nose and sunglasses. The effect was really great!

I looked like Captain Kangaroo.
My ex husband won ” Best Legs” and he was in fishnet stocking, short shorts, garish belt, size 11 pumps, a tight teeshirt with balloon boobs and a long curly wig. :-D

Nope. No desire to. Kind of sexy when women do it.

No the boobs would be a dead give-a-way.

I was in a “Where’s Waldo” type of competition—10 of us signed up to be “Waldos” in a mall. The challenge was to be as difficult to identify to 6 groups of hunters—the groups competed against each other to find us and the 10 of us competed to be the last ones identified. I felt extra pressure as a theater person who specialized in theatrical make up.

I’m pretty short—5’2 and have a unique face, eyes, mannerisms- all clearly female- and at that time, I had hair down to my waist. I dressed up as a Harley biker—rough make up, hair in a biker style ponytail, real-hair goatee, leather jacket, boots, tinted pilot’s glasses—the whole get up. It was hysterical!!!

I’m a drag queen, so yes, I’ve cross dressed and often. I do it for the fun of the performance. It’s all about pleasing the audience for me. I know some drag queens who are transgendered or transsexual, and I know others who do it professionally for the money.

I’m a show-off, so there you have it.

I’ve never really gone out of my way to look like a boy. But I do wear boys clothing a lot.

Technically, all the time. I love wearing my husband’s clothes.

Personal questions really get my panties in a knot!

Hell No.

Nah…...It would be so unladylike!

Yes. I lived as a woman for over a year, working as a reporter for the infamous LA Star. I covered the music industry and wrote reviews for them. Living as a woman was a requirement for sex reassignment surgery,m which I was seriously considering.

I passed in public just fine. In fact, I could look pretty darned hot. I was 5’ 10” and 128 pounds at the time.with naturally bland hair that I let grow out. It later turned dirty blond, but the white coming in now is getting me back to square one. Soon, I;klk look like a towhead again.

I only backed away from sex reassignment surgery when I thought it through and realized that I am just what I am, a man that has some distinct feminine thought patterns. I realized that no surgery could give me XX chromosomes, and that I might as well make the best of the hand nature had dealt me.

That said, I certainly don’t want to suggest that other transgendered people who decide differently are wrong about their sense of self. I just realized that the surgery would not fix my own sense of who I really am. I’m now quite comfortable in a male body. I work out daily and am pretty ripped for a guy my age. I even sport washboard abs. And with a close-cropped full beard, I’d make a lousy drag queen. Go figure.

^applauds

@Hawaii_Jake Thank you. I didn’t get much of that for that period of my life. :-)

I think maybe it doesn’t really count as cross-dressing when you’re actually transsexual. Everyone else thought I was cross-dressing when I wear boy’s clothes, I just feel like I’m dressing as the gender I should be.

@ETpro That’s an awesome story, thanks for sharing. :)

I am and always have been a heterosexual female but for everything except dress up, I prefer male clothing because of comfort mostly. I love board shorts and girl’s boardies have such a low rise (and are often so short) they don’t stay up very well and if I bend over, I share more of my anatomy than I want. I wear boxer shorts to bed because they are so comfy. I don’t like fitted or stretch t shirts so often wear kids or mens. So yep I am a cross dresser although I have never thought of it quite like that before!

I wear men’s clothes all the time, but not in an effort to pass as male. I just find them more comfortable.

Sure.

@Ayesha Perv.

Just for the sake of humor.
I came across some old flyers I had printed up about 6 years ago for pet/house/ranch sitting in my rural community.

I called my biz. ” Farm Avenue pet & house sitting.”
The flyers have all sorts of colorful pictures of horses, barns, dogs & cats, wagons full of hay, roosters, parrots, etc. One of the drawings I came across was just too perfect to not include. It is a man walking, dressed in skirt, flats and wide brimmed hat, of which he he has one hand on the brim of his hat, his face turned towards you smiling and a wiener dog on a leash.

He looks like “Jethro” from the Beverly Hillbillies in drag. lol
My humor being what it is, I just HAD to leave the cross dressing wiener dog walker on the flyer and have had many good laughs from potential clients. :-D
Note: Not dismissive humor, just funny observations of my creative quirks.

@downtide Very cool. Good for you. I know exactly how you and the other women wearing men’s clothes for comfort feel. Personally, I really liked the feel is silky panties. That’s probably because I have a cock to rub against the silky material as I move. So that’s more a transvestite delight than a transsexual one. I don’t fight any convenient pigeonholes. But then gender identity is an extremely complicated, personal thing.

But it’s a pleasure I have forgone to comply with society’s norms. At my age, you have to start thinking about the bucket list, and getting caught that way isn’t a priority item on that list.

@Coloma That’s a great story., If you can make a scan and post it to photobucket or Facebook, please share a link. It just goes to show how funny our assumptions about gender identity really are.

Oh, this is funny to me. I’ve never thought for a second that I cross dress!! But I do wear sweatpants, tennis shoes and a men’s Ralph Lauren tee shirt very often with no makeup indoors, that is. LOL In winter I switch to a sweatshirt. In defense, I bought a pair of pink fuzzy slippers today, those real bushy ones , to wear inside since mine are torn up.
What a sight: a sweatshirt, sweatpants, no makeup and pink slippers. But boxer shorts? No; never have worn those . All I sleep in is a tee. LOL

I did dress up as a woman and will dress up as one again when I need to go on stage to be the dame in a phantomine. I say I make a good Chinese woman :P

@Bart19 Pictures, please. Prove it.

BTW, I was so struck by the comfort expressed by women who wear male articles of clothing and the rarity of such admissions by male jellies that I asked this question about that difference.