For what occasion have you cross dressed? Please share your funny stories with us all.?

Question

**sits back eating pop corn and reads the fun!*

I'll go first. I dress like a man every Halloween. (yes I have tons of pictures) I was paul Stanley from Kiss......the motorcycle cop from the Village People......My boss (yes he was quite amused) and a mobster!

Answer 1

Who me? *looks around desperately for someone else to point out* Oh.... ok...

When I was in college, a photographer friend of mine wanted to do a project and asked me if I would be prepared to dress as a woman for this particular shoot. I agreed and we took some photos of me properly garbed up like a gal (Only a dress, mind. No underwear *shudders*) Anyway whilst he was developing the pics (This was back in the day of analogue and darkrooms) one of the guys looked over his shoulder, saw the photos of me in a dress and asked if I was single!
I suppose I should take it as a compliment, but something about the whole thing freaks me out a little. Thats my one and only time
(Its also the one and only time I ever tell you anything MnG! :(... ;)

Ok this has nothing to do with cross dressing, but I need to erase that particular Image; I once went to fancy dress party as a smurf; My costume was a pair of white shorts and hat and a tub full of blue body paint!

Anyway, I'm emigrating now, see you later!

Answer 2

Oh man. I wrote an answer about this a few months back, but I can't find it so no copy and paste job for me I guess, crap.

Okay...a long time ago, way up friggin' north somewhere I owned a company that did promoting, stage shows, provided crewing for events, etc. And each year there is a state-wide event to crown a "Queen" This is a huge gay, cross-dressing, transvestite event.

The organizers approached our company to provide the lighting, sound and general crewing for the event. They had one particular request though...all of the crew involved in the event...had to dress in drag. It was a slow month, we needed the cash, so of course we said yes.

So picture if you will, a bunch of very manly type guys, all with mass amounts of facial hair, dressed in black dresses (show crews always wear black), nylons, wigs, etc...operating spotlights, working the sound and light boards. It was a riot. We were all pretty uncomfortable in the beginning, but once the show started we got, uhm, more relaxed and we simply enjoyed making fun of each other...and honestly, that was one of the most enjoyable shows I've ever been a part of.

I have a deep deep respect not only for all the cross dressers of the world (a tight dress and your, uhm, manly bits...ouch, dude.), but for all the women out there that put on all those uncomfortable clothes, the make up, the shoes...trust me ladies...I hope you're not doing that to yourselves for us men...cause we ain't worth that much trouble.

Answer 3

Oh, I could be here aaaaall night! I've done this for Halloween too. I once wore a Halloween mask and sweats so no one knew! Every man was staring so hard at my water balloons! I've never had so much attention! When I had long hair it was more fun to do it though. I let my sis-in-law practice putting make-up on me and doing my nails.

My kids enjoy doing this quite often. I'll have to post pics so you can see them. Gotta get their confusions outta the way sooner or later, right?

Answer 4

although I have dressed as men on Halloween too....I have to write about my father instead. I barely knew the man since he left my family when I was 2 years old. But, as I got a little older...I decided to pay him a visit - to try to get to know him. Well, I stayed with him for 2 weeks and I noticed some strange behavior. You see, he likes to drink gin and although he claims to be making "martinis" I never see a drop of dry vermouth enter his glass. He likes Gin straight up...dunked with a few olives. Well, after a few of those he gets "giddy". He goes into his bedroom and comes back out 10 minutes later. He has on a woman's wig....clip-on earrings on his ears....he's sporting a dress and starts to play the banjo and harmonica. After witnessing this several nights in a row - I am now convinced that my genetic pool has been spiked with "oddball" and my bloodline is laced with an enormous amount of "weirdo".

Answer 5

The last time I crossdressed was, Bladder Health Week, November 13 - 19, 2005. The occasion, I participated in a tea drinking contest and someone stole my clothing while I was in competition(I cannot drink tea with my clothes on). A very sweet woman from Andora lent me a pair of extremely comfortable satin culottes and a really cool pair of black patent shoes. I had a hell of a time with her bra, she was only a C and I am at least a D cup. She was a real lifesaver.

Answer 6

I pushed my horns back into my head once... when I dressed as Cupid. It was my first year of college and I wrapped myself in a dinky towel-like cloth and went around campus ringing my little bell and shooting arrows for Valentine's Day.

That's got to more humiliating than dressing as a guy... doesn't it look cute when a woman wears her husband/lovers shirt and jeans? Being Cupid was near humiliating, but it was still fun. I'd never ever do it again though... ♥ my horns too much.

Answer 7

I think I only did this once, during my First Communion. I had a cross on the shirt or whatever you call it. All of us did.

I have Clowned Around a few times, and did a cucumber in the Speedo's 'quasi-striptease' at a family function. Alcohol was involved.

Answer 8

When I was a child, my mother decided it was a good idea to have me dress up as Vanna White for my sister's sixth birthday party. I delighted the party-goers by prancing around in my mother's nighty, distributing prizes. Years later, I was humiliated to be told by one of the females attending the party that she did not know it was me and she thought I was actually a woman at the time! Needless to say, I undeniably corrected her mistaken suppositions on that score!

Answer 9

Well dear sorry to spoil your fun but I have never cross dressed , not my thing.

But I do remember this kid named James who was bet my his buddy's to wear a dress in Middle school all day . And he did it too.

Everyone got a big laugh

What kind of pop corn are you eating? Care to share?

Answer 10

You dressed as Paul of Kiss wow. My knees are weak but I won't confess anything. I might just make a good Gene but that's not cross dressing so I've nothing to add to this question, tongue and all I might add.

The tongue you can't handle the tongue.

Answer 11

^^^WTF was that (Name of...)?

No cross-dressing here...I'm afraid I'm too tall and lanky for that...

The closest I can come to that is the fact that for a long long time I had very long hair. One time I was driving from my brothers wedding, and I come to a stop light. I hear a bunch of dudes hootin' n' hollerin' so I turn to see what the commotion was, and all five dudes shut the F up and turn the other way. They were hootin' at me! HA! I'll bet they felt real manly after that!

I also have gotten more than my fair share of 'Ms.', 'Mrs.', and 'Ma'ams'!