Crossdressing Dares

Note: Most of these dares are meant as an outlet for crossdressers still in the closet to crossdress without getting caught. This is supposed to be a fun place for crossdressing ideas, but not a place for fetishism. This is why I have removed some of the dares, including all of the user-submitted ones. I still encourage people to swap dares on the forums and chat rooms if you're so inclined.


Think you might be a crossdresser, but were too scared to try it out? Or are you so secure about your "manliness" that you can prove it by wearing a dress? Maybe you just want to try something new. Whatever the case, these dares are meant for the beginning crossdresser.

  • In private, try on a dress, a skirt, or whatever you want.
  • Try on some makeup (be careful, one of the easiest ways to get caught is to forget to take it off!)
  • Paint your nails, toenails, etc.

More Advanced, but Still Private

These are fun things to try if you're a private crossdresser but don't want to be out yet.

  • Spend a day at school or work in your regular clothes, with women's clothes under them. (I've done this many times and have never been caught. I've even worn full-length dresses under a t-shirt and jeans without them being too bulky...Just make sure your shirt doesn't slide up when you're stretching or lying down!) (actually, I was caught once by my friend who already knew my secret...she could trace the dress outline on my back under my shirt, and, because she was expecting it, knew it was a dress. Be sure to check your front and back in a mirror before going out!)
  • Shave your legs, chest, or whatever (but plan ahead...You won't want to be wearing shorts or swimming trunks for the next month or so!)
  • Buy your own feminine clothes. No, I don't mean over the internet or from a catalogue...I mean in person. You don't have to try things on, just say you're shopping for your girlfriend. It's fun.

Ambiguous Dare

This is a new kind of idea that I recently came up with and really like: wear unisex/borderline/feminine clothing and declare it a fashion statement. Teens are more likely to get away with this one. Go as risky as you want...You could declare a dress to be a fashion statement, certainly, but more reasonable would be women's jeans or pants, jackets, sweaters, etc...Crap that guys would wear, but with a feminine touch. If you shop for the right things, you might actually look good in it. It's a great idea and fairly easy, except that you have to work up enough courage to shop in the women's section. I did this two weeks ago...I bought a girl's stretch-comb/headband and spent a day at school wearing it. I got mixed reactions...Yeah, one or two guys said it was "gay," and a bunch of people thought I was joking, but I also got tons of compliments. A lot of people took me seriously and thought it was "cute." One guy saw me and actually asked someone next to him, "is that a new style?" Yes! That's exactly what I'm aiming for. One step towards a crossdressing revolution.

Update: I've been thinking about this some more and talking with a bunch of people. Here's some clothing that have shifted toward the feminine side but would be partially acceptable for you to wear:

  • Overalls - no guys seem to wear these anymore!
  • Shortalls - They're suspenders but the bottoms are shorts instead of pants. Very girly, and very cute.
  • Bell bottoms - Like two years ago these were in again, and I even bought a pair and wore them, but now they've gone back to the feminine side.

Also, just last weekend I looked at a guy's fashion catalog, and they had some very feminine stuff in there. I don't know if this is an excuse to wear it, but it's better than nothing. There was girly shirts in there, overalls, girly pants, tights, and lots of other stuff. I dare you to get some "men's" clothing but that is really, really ambiguous.

Oh, another idea. about a week ago I thought I saw a guy wearing a skirt. It turned out just to be some piece of fabric or other type of clothing tied around his waist. From the back he was crossdressing, but from the front you could tell it didn't go all the way around. Aha! :) This is the only way I can think of tricking people to think that you are wearing girl's clothing when you aren't, but I'm sure there are others.

Getting More Hardcore

These are more risky dares for the non-out crossdresser.

  • Go out for a drive in drag. I do this all the time. I don't want to get caught by my neighbors, so I cover whatever I'm wearing with regular clothes and then take them off in the car. I worry about seeing someone I know or speeding and getting pulled over by a cop (boy would that be embarrassing!) but otherwise it's lots of fun...You get to be seen by lots of people in drag, and you're safe in your car.
  • Go out for a walk in drag. Well, this is scarier because you don't have the safety of being in your own car. I haven't tried it, but would like to someday...The trick is to not be seen by someone you know and to not be mugged or anything. If you're having trouble working up courage, here's an idea: Hide an extra set of car keys somewhere. Then, go home and get in drag, and then drive to about a mile away from your keys. Lock yourself out of your car, and then go get your keys.
  • Convince someone to dress you up in drag. You'd be surprised at how easily this can be done without the other person knowing you want to do it. Poker games or bets you purposely lose are an easy way. Hinting and joking also work. I've had lots of success with this.
  • Crossdress for Halloween. There's no better time or excuse to dress in drag than Halloween. It only happens once a year, so make it a fun one!
  • Crossdress at home with the windows open. This is a good step towards knowing what it would feel like to crossdress in public, but within the safety of your own home. If you crossdress enough, pretty soon you'll get lazy enough and forget to close all your blinds. I do all the time. I'm sure my neighbors all know my secret.
  • Wear lots of Jewelry. Get your ears pierced. Lots of guys wear jewelry, but if you don't already it'll feel nice to start. Start going with the more feminine earrings, necklaces, bracelets, etc.

The Last Steps

So you finally accept yourself as a crossdresser, and want others to know too. Here's the final steps you can take.

  • Come out to your friends and/or family. I haven't finished doing this yet, and I don't know if or when I will, but so far this has been one of the most rewarding experiences of my life. Finally coming out with my secret felt wonderful. And having my friends meet a new part of my identity was also fun.
  • Join a crossdressing club. Yep, there's others out there like you, and if you wanna meet them, you can.
  • Go to school or work or whatever you want wearing a skirt or dress. I do this now, and when people ask, I either give a reason that's not an excuse, like, "because it's a nice day out," and not "because I was held at gunpoint and forced to do it" or I tell them that I believe people should be able to wear whatever clothes they want. Obviously, think first about the consequences of doing this...Know that some people who've done this have been victims of violence, have been fired, or expelled from school.
  • Try to pass as a woman. It's every crossdresser's dream to be pretty enough to be mistaken for a woman. This will probably involve breast forms, wigs, makeovers, the whole shebang. And, of course, you'll have to test out your new looks in public someplace!

Start 'dressing all the time. Like all of us, you want to be able to express yourself by wearing whatever you want, whenever you want. Unfortunately, doing this can have severe consequences, like getting expelled from school, fired from work, mocked by peers, and dumped by loved ones. I'm afraid not everyone understands. *sigh*.

Back to Table of Contents