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
- 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.
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
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
- 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
- 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
- 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*.
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