Crossdressing?

Question

If I want to start crossdressing how do I start ?

Answer 1

Get some womens clothes

Answer 2

Part of it centers on why. Why do you want to wear women's clothes and accoutrements? Part of it centers on where. If you are doing it privately in your home where no one will see, that is different from being that strange man in a dress walking down the street. I know a businessman in a town I used to live in, it ruined his business when he took his bearded and bald head to work while wearing his wife's dress and fishnet stockings. If you were so old as to live in a nursing home, then that is a still greater complication because you essentially have no privacy, resources.

But there are always Mardi Gras and Halloween. I got fed up with a bunch of old cows that I worked with, that one Halloween I put on one of my wife's old dresses, a pair of her hose, bought a cheap wig and makeup and stopped by WalMart for some inexpensive shoes. Only one other skirt was in the building when I went to work and it was of a woman dressed as a witch. The supervisor took my picture for the costume contest and I found out later that the big boss who decided didn't pick me simply because the only thing he thought there was to my costume was a really bad wig--until afterwards someone informed him that that woman wasn't. It was a real hoot to start talking on the phone to customers and hear a chorus of OMGs from people all around when my male voice spoke. It took me just about two hours to prepare and I haven't touched the stuff since so I'm not exactly a real crossdresser. I don't get my jollies by doing that. But getting the pieces isn't hard, but if you are going to go out, pick your days carefully, okay?

Answer 3

I am a crossdresser and have been doing it for years and years. It is fun and I even go out in public a lot. There is no certain way to start, but I would suggest maybe a makeover salon There may be one near you They can be found on the net. Do you have a girlfriend you can confide in? Many women can be very helpful.

Answer 4

Start slow with underwear. When you become more confident move on to other clothing items. You can also start by wearing a little make-up, if you so choose.
Women have been "cross-dressing" for many years. Slacks, hats, ties, etc. No one says anything about that. Why is it so different for men?
I have had friends who crossdressed only at special occasions, but others who do it every day. It's not a matter of being gay, just whatever you are more comfortable in.

Answer 5

Crossdressing is harmless,I have crossdressed for over 20years discreetly.It doesnt mean you are gay,it just means you enjoy the femmine side of you,please do not judge this guy there are worse things he could like other than wearing womens clothing.I just wanted to thank the woman for your support to this question...if you need any help please contact me..have a great day...

Answer 6

you may want to start by reading a book called the lazy crossdresser, this will give you some of the basic info you need.

Answer 7

Start by doing research. Read beauty magazines and books, articles on etiquette and body-language, grooming etc. Practice in the privacy of your own home.

If you are shy about buying clothing, learn to lie (Oh, I'm buying for my girlfriend. How does your returns policy work...) or shop over the internet until you have the confidence to go out.

Of course, all this assumes you want to go 'en femme' in public. If you just want to do this privately, forget all I said, buy the stuff over the internet, and happy dressing!

Answer 8

There are plenty of great resources on the internet to help get you started.

As far as the actual items, it all depends on how comfortable you are buying them. If you have no problem, then any place that sells women's clothing will do. I've used K-Mart, Target and a few large stores and a few small boutiques.

Or you can always do mail order.

Answer 9

If you wanna do it, go for it, even if others think it's sick.

Can't say I really have much experience here as I'm still learning myself. However, you could start with some resources on the Internet and see if any places in your local area is cross-dresser friendly.

Answer 10

Just go to the store and buy some nice panties, and a bra. Find yourself a wonderful pair of hose, and a garter belt if that is what you choose. Get a nice skirt, blouse, and some shoes.

Answer 11

You have obviously thought about this for more than just today. Go to a store, look at what you want and get it, or order it online. Try to find a friend to help and that you can talk with.