help! i think i want to try crossdressing!?

Question

First, never mind the avatar -- I'm a late-20's hetero male.

I've read some Q/A's here and other places about crossdressing. It seems like it might be a fun hobby, and somewhat subversive to boot. I have no experience with wearing girls' clothes other than one time when my gf dressed me up in her clothes and makeup, just for fun. I didn't think I'd enjoy it much, and I thought/knew I looked silly, but she had a good time with it.

So... I think I might try crossdressing again, but I'm not sure where/how to start. Are there any current crossdressers (ideally, who started in their 20's) that can give me some advice/tips on how to start and what's fun? Are there any girls that can give any advice? Pros and cons?

I'm of course rather nervous about this, but I gotta ask. Any feedback welcome... and I'll be happy to answer any questions.

p.s. I have no idea what category to put this in, so I'll go with what looks good... comments on that welcome as well.

Answer 1

How to....well, if you want to start slow...start wearing panties. Panty hose can be worn under slacks, and even a small cupped bra can be hidden under a bulky sweater, or sports coat.

You can shop for clothes via on line, if you are shy about shopping in public (though if your girlfriend likes, you can always take her and have her buy it, or be with you when you do.) There are some web sites that make women's clothes for men. (Suddenly fem has some cute things). Don't get anything that will accent your broader shoulders. Watch those square cut blouses.

Wigs are a great way to have that suddenly fem hairdo without having to alter your own hair. And for makeup, you want to find something that will first take the shadow out of your beard, and then the foundation to even out the skin tones.

Have fun. It's all just for fun. I know you're nervous, so practice at home, and make a deal with your girlfriend that even though she adores you dressed, she'll give an unbiased eye to let you know if you can pass, should you wish to venture into public. Or just screw public opinion and go anyway.

Answer 2

If you want to try, try! Doing something sexually subversive is the new black (I'm into BDSM).

For most, crossdressing is a sexual thing, although some say it's an emotional thing, too. Plenty of crossdressers are straight. There's the whole gender spectrum that might be interesting to you to look into. I'd start at Wikipedia.

As for real advice... any niche thing like this is really what online groups are made for, so I'd look into those. If you go outside, go to a LGBT friendly place or bar (if you're interested in the night scene) at first.

This advice is going to be silly, in no order; color coordinate, buy things that fit rather than buying for the size you wish you were, be prepared for confrontation outside if you don't fit the gender role, buy a wig, don't be afraid to buy things directly in stores, and try not to make it the center of your life. I'm sure others can add lots of other advice.

Have fun, be safe.

Answer 3

This is the perfect category for this question, don't be shy.

if you had fun and enjoyed it, why do you need help?

heh, I'll leave the soapbox speach at home.

Tips for starters ummm...uh....hmmm........a girls always gotta look her best. hygene hygene hygene, anything and everything you can think of. A wild aray of hair care products....don't be ashamed to go metrosexual with it :P

The biggest problem I have always seen with crossdressers or transgender icons has been their none natural looking ness. Don't pick something because it looks great on your girlfriend....get it because it looks great on you.

Grab some shades that work for your own skin tone. and please for the love of all the gods, do not use bright blue tammy fae eyeshadow...that just screams for an *** kickin'.

The only thing I can advise is to actually try on clothes, try on earrings, try the makeup. You're a guy and you know you're a guy, never buy into the "more is better" ideology. Discrete but yet sexy....that's what you want to go for. Not because I am attempting to thwart your attempts....but because I know even women laugh at clowns.

Answer 4

Did you see that movie where this boy always dressed like a girl? It was on just recently. On the lifetime tv channel. It was a true story. I can't think of what the boys name was, but he had everyone call him by a girls name. (They refered to him as transgendered, and said he was born with a girls brain) Wish I could think of it. You should watch that movie to see if that's the way you feel. Look on the lifetime web site. I think I remember now, the boys real name was Freddy, but when he was brutally murdered the mother buried her under the name s/he chose. If you get a chance, watch the movie !. This might help you with what you are struggling with and at the end of the movie it gives a web site to go to. Good Luck. !

Answer 5

hunny, as the wife of a cross dresser, i say go for it and have fun!!!
while you may want to try some everyday looks, get a few kinky ones in there too!
my husband and i LOVE going to fetish clubs as a couple of girls and i'm totally fine with it.we don't exactly have an open relationship, but we bring many women home this way.
you said your gf enjoyed dressing you up,is she a bisexual?
if she is, then not only does she have the best of both worlds on her end, but she's got yours now too. she doesn't have to go looking for a woman, your there for her.
(try some role playing games too, those are really fun and they help set the mood sometimes)
whatever you decide, do it because it feels right to you.
i hope that you explore this new way of pleasuring yourself and you gf, best of luck.

Answer 6

i started crossdressing in my early teens and have been cd'ing ever since, im now 37, married to a wonderful woman who knows and have three kids. if you want to start crossdressing, i say go for it. there is no certain way to start crossdressing, you'll find certain clothing that you like and dis-like, for me any time i dress up i have to be in pantyhose, for you it may be something else.
the pros and cons are wha ever you make them up to be, some of my pros are, i get extremely hornywhen dressed, my sexual sences are at a peek, and i love the feeling of the feminine clothing i wear. the cons for me are, sometimes i get very "confused" about who i am...and i hate the feeling of "hiding" my crossdressing desires from "the rest of the world".

hope this helps you a lil bit and good luck in your crossdressing adventures

Answer 7

Some think that cross dressing means your gay..absolutely not! Don't we see a whole bunch of girls and women wearing pants with zippers in the front, men caps, hats, ties, etc..yet no one even thinks of calling them gay or cross dressers.

I love to dress in men's clothing..jeans, t-shirt, cap and even our sneakers now..you cant tell the difference if u wear mens' or womens'

I did a film once where I had to transform myself into a man..and when I finished you couldn't tell I was a woman. I stayed that way for the rest of the evening and had a ball, a great time fooling everyone. I was in a man's world and it was just great. Of course, I did it just that time..but having the opportunity of doing it again..I would..it was just great and lots of fun.

Answer 8

how do you dress a cross?
I've seen catholics toss a white or purple robe around them,but that's not much in the way of being dressed.the Romans dressed a cross with Jesus,but then that didn't go over very well.too many fashion critics in that day and age.
so maybe i should start a question with how do you dress a cross.maybe that would get you a good answer.

Answer 9

You cant knock it til you try it. You live once, if you think it will be fun go for it, you just might like it too. The movie the girl above is speaking about is A Girl Like Me. Im a Lifetime junkie. Its good. Check listings to see when it airs again. Good Luck.

Answer 10

I am just like u, but i am bi, my GF knows it and we are all right with it. I have never tried CD but I wish one day I find a real Beautiful CD and start doing it with him.

If you are not gay or bisexual , so why would u need some sort of CD fantasy?! Are u sure u are Heterosexual? Have u ever been in love with a boy or this kind of thing?!

My suggestion is that if u r not gay or bi, don't start it. Cross Dressers need to show themselves, do u want it?
and u know habits are hard to avoid, so start it if u r sure!