This troper knows so many females that have desired or suceeded in dressing boys up in girls clothing. This troper is also one of said females.

This Troper played with the trope - she was a very enthusiastic helper when one of her friends decided to dress up as a guy for prom. She wouldn't mind helping a guy either, though.

This troper is a WholesomeCrossdresser, so it's not like any convincing/pleading/etc. is required to prompt donning feminine attire and such. However, whenever I've needed my female friends for extra help, well... yeah. One of my friends works as a make-up artist, and I've never seen her smile as much when applying make-up on anyone else. Another one of my friends said the general idea is fun for girls.

Subverted with this troper and her friends. I hang out with ALOT of drag kings and queens, and in our various circles, doing drag professionally or semi-professionally is considered the height of cool. One of my amateur friends is trying to get me to do a number with him...I'm reluctant not because I don't want to cross-dress, but because I'm scared of performing on a stage. One of my trans guy friends said he would give me his old binder, though, and [TheDandy another friend] offered to lend me his clothes, so I'm starting to come around...

This troper and her friend did this to the friend's brother. He's... rather feminine-looking, so the effect was startling. He also loved the whole undertaking.

This Troper was at a friend's birthday party, and sat down to watch the ending of Forrest Gump on her T.V. When I got back up again, the rest of the girls had put makeup on a male guest's face, and were escorting him down the hall to put on the friend's dress. We then walked him down the street and back.

This is horrible OldShame, but this troper's very feminist English teacher in 9th grade had the class put on a private ''RomeoAndJuliet'' play that only the class would see, and instead of the parts being defined by gender she had us draw character names out of a hat, and we'd have to memorize that character's lines and play that character. This male troper was the lucky guy who picked Juliet, and thus got to be fitted with the perfect-sized dress and a wig by some enthusiastic female classmates.

This Troper's school has a cross-dress day, I shit you not. The really, really disturbing thing about it is that some of the guys when crossdressing are strangely convincing, with many having better legs (after shaving, of course) than many of the women. Oh yeah, and a very good friend of mine kept asking me to participate in it, and I finally broke down and she gave me one of her shirts and a skirt. I wore the skirt and shirt she gave me for one period, then quit. Should I do this next year, and should I ask for a skirt or dress and some tights? (I probably won't, but I think it'll be fun to look at the replies.)

P.S-it was a completely normal skirt and shirt. Now that I think about it it's kind of weird she didn't get me a pair of tights and/or something frilly, because she seems like the kind of person who'd want to dress me like that.

Lol, my school has an unofficial cross-dress day too, I totally know what you mean. It's hilarious. Our school has uniforms, so guys and girls swap uniforms and it can be really hard to tell, from a distance, what gender is what. For you, I say go all out: the more over-the-top the better.

I was thinking I would ask her for clothes (Skirt or dress and some tights) before the day, and I'd try them on and see if it would work.

For a school play, this troper had to help dress up our main (male) lead as a girl for a photo. Actually, all the girls in the class helped--from the wig to the makeup to the dress to the expressions he needed to make to look more feminine. And yes, it was fun all around. (Except maybe for the guy in the dress.)

Being a younger brother at a slumber party was hell for This Troper. My sister and her friends took me into their room and put a pink dress on me. They also put makeup, nail polish and perfume on me as well as a ribbon in my hair. To make it worse, I was forced to stay there as they watched Legally Blonde and fell asleep.

So this was based on you?

In Lit class freshman year, the class split into groups to do a 32-second ''Macbeth'' reenactment, using only key lines and actions. We presented, and the best actors for each character got to go up, don costumes, and present together for a 16-second reenactment. I'd been chosen, and my character was Lady Macbeth. I'd picked out an amorphous shawl-like thing and a cap for my costume. The teacher walked out there, took one look at me, and said, "Oh come on, dude." She proceeded to force me into the floweriest, fluffiest pink dress in the ''building'', and paraded me onto the "stage" we'd made of the classroom. Hilarity ensued for the class (I'm the PerkyGoth who ''never'' dresses in anything but monochrome) and embarrassment ensued for me. People've still got ''videos'' of it, man.

My insane sixth grade teacher: "All right, since all the girls are doing something else, I need five guys to dress in drag, dance around on stage and pretend to get a needle stuck in their arm, and volenteers?" The kicker? The 'volenteers' were on the football team.