Just wondering how many Doper guys have ever worn women’s clothing (that they will admit to). As a lifestyle choice, for Halloween, theater, or any other reason.
I have twice. Both times for Halloween while in college. Once, a smart 3-piece suit as Queen Elizabeth, and the following year a cute green jumper as Amy Carter. Those skirts sure are comfy, tho that breeze can be chilly.
I’ve been wearing women’s panties ever since the wife found a pair in my truck. 
I have not yet done drag. It’s on my long-term list.
I dressed up as a cheerleader once in High School for a Halloween party.
Dressed up in drag when I went to the Rocky Horror Picture Show in college.
That’s about it. 
–IDB
Can cross dressing women participate? If so, I’ve got about nine pairs of men’s slacks I wear on a regular basis. At least four of them are from the 60s/70s so there no mistakening them for women’s slacks.
Well, it depends on your motivation. Are you wearing mens’ slacks because they fit, they look nice, they’re the right price, blah blah blah, or are you wearing them because you want to dress like a man?
Moi: Nope.
I dressed my son up as a girl for Halloween when he was about 15. He fit in my clothes perfectly. I did his hair and makeup. God! he looked great! I’ve never dressed in drag. I doubt I could pull it off.
My mother once dressed me up for Halloween as a girl. I think I was about 4 or 5. I’m over it, now. Someday, I may even forgive her.
“But the OP didn’t ask why the men crossdressed so why should I have to justify why I do,” whines JuanitaTech.
A former female friend of mine once convinced me to wear one of her dressed because it would be “cute”. It fit me rather well, actually, except it was a bit tight in the shoulders.
Drag for halloween. I’m kinda big and scary as a bloke, so in women’s clothes I’m terrifying:).
Cheers, Bippy (wearing a floral pattern, off the shoulder number )
Not justifying, clarifying: are we distinguishing between, say, borrowing my wife’s winter coat when I go out to get the mail versus borrowing her dresses for a night out on the town? I see a difference between the two…
I’ve done drag for Halloween as a French Maid. I’m built like a beer barrell so it wasn’t pretty. But I must admit I found it rather exciting to wear a mini-skirt with fish-nets and nothing underneath.
I wear the vintage ones because I can’t get enough of that boot cut that was popular for men’s slacks in the 60s/70s and the newer ones because I just liked the way they look. So I guess there’s no underlying desire to be a man just an overwhelming desire to look fab.
Okay it’s freaking me out but that actually turned me on a little, Homebrew. I wonder if I can get an french maid costume for my husband?
BTW, for a halloween party one year my big old hairy husband dressed up as ??? Oh her name just left my head but it’s the cranky old black lady on “Sanford and Son” that calls Red Fox a “fish eyed fool”. Anyway, hubby really went all out. He’s white so he painted his arms and face black, put on a gray wig, dress and hose and even had a pocketbook to smack people around with. He goes be-bopping into the costume party only to find out that it’s really a surprise birthday party for him and no one else is in a costume!!! What a hoot. He refuses to go to costume parties at all now.
The character to whom you’re referring, Copper, is Aunt Ester.
I once dressed up as a belly dancer to surprose my son on his 21st birthday. I remember walking down the street in Berkeley and getting no odd looks…but that’s not a true measure of my feminine good looks! My wife was decked out as a clown.
When my son answered the door, and let us in, he thought we were an act hired by his friends (I had music with me for dancing and did a few moves)…then my wife and I started laughing and the ruse was up.
I have to admit that having those balloons on my chest made me think that it would be interesting to have breast IF I was a woman…but I think I was thinking about this as a man, not a woman.
No other instances…other than the time my wife had me put on her hose and panties and…
That’s it. Thanks.
I’ve dressed up as an old tart, complete with make-up and everything, for carnaval once. It was fun, but I wouldn’t make a habbit out of it.
Dressed up as a nun once too, but didn’t make a habbit out of that either. OUCH! Stop throwing rotten fruit.
we once hosted a couple and the man was a cross dresser. he said he found it “relaxing”.
he was a redneck of the highest order; he was also blind in one eye. and he loved stiletto heels!!! we had a class top coffee table and it made me VERY nervous when he would teeter around it.
worst moment: he answered the door in a nightgown and heels when my girlfriends came to pick me up for a day of gal pal stuff.
oh god i wish i had a picture.
he stole one of my bras when they left…