# Ok, when have you cross-dressed? **URL:** \ **Category:** Miscellaneous and Personal Stuff I Must Share\ **Created:** [August 15, 2001, 4:26pm UTC](https://boards.straightdope.com/t/ok-when-have-you-cross-dressed/76404 "2001-08-15T16:26:59Z")\ **Posts on this page:** 20\ **Page:** 1
**Author:** ![Tomcat](https://avatars.discourse-cdn.com/v4/letter/t/8e8cbc/32.png) [@Tomcat](https://boards.straightdope.com/u/Tomcat)\ **Post date:** [August 15, 2001, 4:26pm UTC](https://boards.straightdope.com/t/ok-when-have-you-cross-dressed/76404/1 "2001-08-15T16:26:59Z")
Yep, I did it. I wore a sexy black teddy with stockings and lace gloves- but no heels. Did this every Saturday night for a whole summer…Can you guess why? Yep. I was Brad sub[/sub]. It was hard getting the bodice to fit me properly, but that loose-threaded corset look added a special ‘wildness’ to the outfit. Aaaahhh…the days of of being part of a group of extremely weird people. And no, it didn’t get me laid by Janet, even though I really, really tried… So, anyone else have a cross-dressing story? Legit funniness, or did you just like the way the other teams underwear made you feel sexy? -Tcat ---
**Author:** ![Strainger](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/strainger/32/244_2.png) [@Strainger](https://boards.straightdope.com/u/Strainger)\ **Post date:** [August 15, 2001, 4:28pm UTC](https://boards.straightdope.com/t/ok-when-have-you-cross-dressed/76404/2 "2001-08-15T16:28:46Z")
Me? Cross-dress? Never. ---
**Author:** ![Olentzero](https://avatars.discourse-cdn.com/v4/letter/o/90ced4/32.png) [@Olentzero](https://boards.straightdope.com/u/Olentzero)\ **Post date:** [August 15, 2001, 4:36pm UTC](https://boards.straightdope.com/t/ok-when-have-you-cross-dressed/76404/3 "2001-08-15T16:36:33Z")
Halloween 1989. Switched clothes with my GF at the time. Even shaved my pits and legs, wore nylons. She wore my best suit. The adventures after the party were… rather stimulating. ---
**Author:** ![andygirl](https://avatars.discourse-cdn.com/v4/letter/a/a9adbd/32.png) [@andygirl](https://boards.straightdope.com/u/andygirl)\ **Post date:** [August 15, 2001, 4:41pm UTC](https://boards.straightdope.com/t/ok-when-have-you-cross-dressed/76404/4 "2001-08-15T16:41:52Z")
Several times. The first of note was when my english prof at the time was giving a lecture on Shakespearean cross-dressing and a group of us decided to go in drag to show solidarity. The second time was for the drag ball at my school. Damn, I looked butch. I’ll do drag every once and awhile, but those were times when I’ve gone all out. So to speak. [sub]and it makes me feel wicked sexy with the right circumstances.[/sub] ---
**Author:** ![FairyChatMom](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/fairychatmom/32/21825_2.png) [@FairyChatMom](https://boards.straightdope.com/u/FairyChatMom)\ **Post date:** [August 15, 2001, 4:41pm UTC](https://boards.straightdope.com/t/ok-when-have-you-cross-dressed/76404/5 "2001-08-15T16:41:56Z")
Very, very early in my Navy days, I convinced the guy I was dating to let me try on his dress blues - the old-style sailor top, bell-bottoms complete with 13 buttons, and dixie cup cap. I had just had my hair permed, so it was especially curly and golden. I’ve got a pic of me somewhere wearing this outfit - I was just too adorable for words!! Kinda unexciting, but I wanted to share anyway… ---
**Author:** ![Padeye](https://avatars.discourse-cdn.com/v4/letter/p/a9a28c/32.png) [@Padeye](https://boards.straightdope.com/u/Padeye)\ **Post date:** [August 15, 2001, 4:45pm UTC](https://boards.straightdope.com/t/ok-when-have-you-cross-dressed/76404/6 "2001-08-15T16:45:51Z")
I got the halloween treatment when I was six or seven. Mom went all out with wig, makeup, etc. and at least for a night got that daughter she never had. She was really getting into it and I couldn’t understand why she was freaking about me not sitting with my knees together. That and a halloween as the devil, complete homemeade body suit with horns and tail and a pitchfork, don’t appear to have had any adverse effect on my sexuality or faith. My brother on the other hand… Actually I never saw him in drag until he was completely out. He’s not a drag queen, far from it, but did a cabaret show at a club in Tucson as his comedy alter ego Marge Greenbaum. Think of the early Phylis Diller with a good dose of Carol channing… but not nearly so attractive 😛 ---
**Author:** ![BunnyGirl](https://avatars.discourse-cdn.com/v4/letter/b/22d042/32.png) [@BunnyGirl](https://boards.straightdope.com/u/BunnyGirl)\ **Post date:** [August 15, 2001, 5:07pm UTC](https://boards.straightdope.com/t/ok-when-have-you-cross-dressed/76404/7 "2001-08-15T17:07:07Z")
> [@](#): > > \*Originally posted by Strainger \* > \*\*Me? Cross-dress? Never. \*\* Oh,reeeeaaaalllly? Does the word “belly dancer” bring anything to mind? ---
**Author:** ![Strainger](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/strainger/32/244_2.png) [@Strainger](https://boards.straightdope.com/u/Strainger)\ **Post date:** [August 15, 2001, 5:10pm UTC](https://boards.straightdope.com/t/ok-when-have-you-cross-dressed/76404/8 "2001-08-15T17:10:09Z")
I have no idea what you could possibly be talking about. (Insert innocent “puppy eyes” smilie here.) ---
**Author:** ![BunnyGirl](https://avatars.discourse-cdn.com/v4/letter/b/22d042/32.png) [@BunnyGirl](https://boards.straightdope.com/u/BunnyGirl)\ **Post date:** [August 15, 2001, 5:24pm UTC](https://boards.straightdope.com/t/ok-when-have-you-cross-dressed/76404/9 "2001-08-15T17:24:47Z")
[Evidence](http://www.geocities.com/techchick68/vegas/belly2.html)! So what do you have to say for yourself, young man?! ---
**Author:** ![plnnr](https://avatars.discourse-cdn.com/v4/letter/p/7ea924/32.png) [@plnnr](https://boards.straightdope.com/u/plnnr)\ **Post date:** [August 15, 2001, 5:37pm UTC](https://boards.straightdope.com/t/ok-when-have-you-cross-dressed/76404/10 "2001-08-15T17:37:42Z")
“Marge, you can’t be a cop, because then you’ll be “The Man.” And if you’re the man, then I must be the woman and I’ll have to wear your underwear, which, as I’ve said, is strictly a comfort thing.” - Homer Simpson (there’s a Simpson quote for damn near everything, isn’t there?). ---
**Author:** ![Knighted\_Vorpal\_Sword](https://avatars.discourse-cdn.com/v4/letter/k/ac91a4/32.png) [@Knighted\_Vorpal\_Sword](https://boards.straightdope.com/u/Knighted_Vorpal_Sword)\ **Post date:** [August 15, 2001, 5:39pm UTC](https://boards.straightdope.com/t/ok-when-have-you-cross-dressed/76404/11 "2001-08-15T17:39:09Z")
I cross dressed once in a March long ago, for a Jewish holiday called Purim (where many people wear costumes). It was freezing out, and I had on a skirt, shirt/blouse, makeup, panty hose, etc. **Damn** it was cold! I swore never to wear a skirt in the winter again. (I also had to hike up my skirt to drive, but that’s another story.) ---
**Author:** ![Kiki](https://avatars.discourse-cdn.com/v4/letter/k/dc4da7/32.png) [@Kiki](https://boards.straightdope.com/u/Kiki)\ **Post date:** [August 15, 2001, 5:41pm UTC](https://boards.straightdope.com/t/ok-when-have-you-cross-dressed/76404/12 "2001-08-15T17:41:41Z")
I wore my brothers underwear once because all mine were dirty. That’s about as close as I’ve come to cross dressing unless you count wearing my SO’s boxers around the house. And I did dress up like a cowboy once for halloween. That’s about it. ---
**Author:** ![Astroboy14](https://avatars.discourse-cdn.com/v4/letter/a/df705f/32.png) [@Astroboy14](https://boards.straightdope.com/u/Astroboy14)\ **Post date:** [August 15, 2001, 5:44pm UTC](https://boards.straightdope.com/t/ok-when-have-you-cross-dressed/76404/13 "2001-08-15T17:44:02Z")
I cross-dressed every Halloween during my college years… My Mother owned a dress shop in Bangor, ME that was geared towards large women, and I was able to sweet-talk her out of a really cool maroon, sequined twenties-style flapper dress!😃 Shoes to match were a different matter, however. I wear size 16, and they just don’t make them that size for wimmen! (Or for men, anymore, it seems! I’ve been trying to find a pair of Rockport walking shoes lately, which they used to make in a 16, but have had NO luck at all!) ---
**Author:** ![magdalene](https://avatars.discourse-cdn.com/v4/letter/m/df788c/32.png) [@magdalene](https://boards.straightdope.com/u/magdalene)\ **Post date:** [August 15, 2001, 5:47pm UTC](https://boards.straightdope.com/t/ok-when-have-you-cross-dressed/76404/14 "2001-08-15T17:47:26Z")
My friend Joe dressed as a nun and I dressed as a priest for the High Heel Races in D.C. After a formal ball my friends and I convinced our dates to switch clothes with us. They looked better in our dresses than we did, harummph. But we looked more like sexy tux-wearing villainesses than like caterers. TomCat, every time you post my opinion of you goes up. 🙂 ---
**Author:** ![Strainger](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/strainger/32/244_2.png) [@Strainger](https://boards.straightdope.com/u/Strainger)\ **Post date:** [August 15, 2001, 6:05pm UTC](https://boards.straightdope.com/t/ok-when-have-you-cross-dressed/76404/15 "2001-08-15T18:05:00Z")
> [@](#): > > \*Originally posted by BunnyGirl \* > \*\*So what do you have to say for yourself, young man?! \*\* Uuuhh…wow, it’s amazing what you can do with PhotoShop. ---
**Author:** ![Lamia](https://avatars.discourse-cdn.com/v4/letter/l/8e7dd6/32.png) [@Lamia](https://boards.straightdope.com/u/Lamia)\ **Post date:** [August 15, 2001, 7:29pm UTC](https://boards.straightdope.com/t/ok-when-have-you-cross-dressed/76404/16 "2001-08-15T19:29:07Z")
I [cross-dressed](http://www.geocities.com/yellowlamia/mepics.html) for a drag show. I won, too. 🙂 ---
**Author:** ![Chance\_the\_Gardener](https://avatars.discourse-cdn.com/v4/letter/c/eada6e/32.png) [@Chance\_the\_Gardener](https://boards.straightdope.com/u/Chance_the_Gardener)\ **Post date:** [August 15, 2001, 7:40pm UTC](https://boards.straightdope.com/t/ok-when-have-you-cross-dressed/76404/17 "2001-08-15T19:40:40Z")
I dressed up as Liza Minnelli back in 1989. My sisters helped me with the makeup, which was a greuling process, to be sure. I wore one of my mom’s old dresses, which was a bit too snug for comfort. The hair on my legs was covered by black stockings, and I never could get the hang of the heels. That black wig made the whole thing work. There is one photo of this, taken against my will. That photo still exists, but I’ll never let it escape. I’m straight—I _swear!!!_ ---
**Author:** ![Enderw24](https://avatars.discourse-cdn.com/v4/letter/e/ba9def/32.png) [@Enderw24](https://boards.straightdope.com/u/Enderw24)\ **Post date:** [August 15, 2001, 7:57pm UTC](https://boards.straightdope.com/t/ok-when-have-you-cross-dressed/76404/18 "2001-08-15T19:57:33Z")
I’ve cross dressed twice. Once I was in Israel and our last Shabbat the entire lot of us (close to 30) decided to dress up in drag. We went to the size equivilent member of the opposite gender and traded clothes. No one shaved though, so it looked like 15 hot girls in shirts and ties and 15 sasquatches in sundresses. The second time was a little over a year ago at Oberlin’s drag ball. I was a geisha. Some of you poor, unfortunate souls have seen the pictures. **Strainger** , the second picture on the webpage kinda looks like Vishnu. ---
**Author:** ![Eve](https://avatars.discourse-cdn.com/v4/letter/e/9e8a1a/32.png) [@Eve](https://boards.straightdope.com/u/Eve)\ **Post date:** [August 15, 2001, 8:02pm UTC](https://boards.straightdope.com/t/ok-when-have-you-cross-dressed/76404/19 "2001-08-15T20:02:27Z")
“15 sasquatches in sundresses”—Yet ANOTHER great band name! ---
**Author:** ![Strainger](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/strainger/32/244_2.png) [@Strainger](https://boards.straightdope.com/u/Strainger)\ **Post date:** [August 15, 2001, 8:10pm UTC](https://boards.straightdope.com/t/ok-when-have-you-cross-dressed/76404/20 "2001-08-15T20:10:14Z")
**Enderw24** > [@](#): > > Strainger, the second picture on the webpage kinda looks like Vishnu. Vishnu drinks beer? [Next page](https://boards.straightdope.com/t/ok-when-have-you-cross-dressed/76404.md?page=2)