IntroductoryYou think you might be a crossdresser, but are 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 AND toenail(Girly colors!! It feels good!)
More Advanced, but Still PrivateThese 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!) 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!!
Getting More HardcoreThese are more risky dares for the non-out crossdresser.
- Go out for a drive in drag. If you don't want to get caught by my neighbors, cover whatever you're wearing with regular clothes and then take them off in the car. Don't worry about seeing someone you know...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... 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.
- 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.
- 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 StepsSo 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!!
- 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!