What to wear the first time you crossdress

Crossdressing for the first time

Crossdressing for the first time

Crossdressing for the first time can be a daunting affair. Most men will find that they initially are drawn to a particular item of clothing, this would obviously be a natural place to begin. By starting small like this you will not only save money, but also work on overcoming your initial fears.

I don’t recommend it, but if you’d like to try getting dressed fully as a woman, you want to find something that will make it easy to look feminine. A skirt that ends below your knees and a long sleeve blouse is a good place to start. You may find that if you’re broad shouldered you’ll need to get a larger blouse than skirt. It is usually more difficult to find a dress that fits a man’s physique well. This outfit will hide your (likely) unfeminine knees, and broad larger biceps.

Make sure you shave your legs, arms and face. Put on a pair of pantyhose and find some low heels or boots to match your outfit. As for intimates, wear a bra stuffed with padding and a pair of panties to keep your unfeminine parts in check.

For clothes I highly recommend Newport News – I’ve found their size guides to be fairly accurate. They accept returns and have a good selection of clothes. For shoes Zappos has a selection of larger shoes (you’re likely to find you’ll need a wide, and a size or two larger than your regular shoe size).

Makeup is a bit trickier. If you want to be discrete you can order online, but it’s hard to match your color. As a general rule try to wear foundation that matches your skin color, or is slightly darker. Also, don’t go overboard on the mascara and lipstick – your makeup should accent your beautiful face, not be the first thing someone notices about you.

Good luck!

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33 Comments - Leave a comment
  1. aeros46@hotmaIL.COM says:

    all i want to knwo is how ot crossdress in my own home as i;m disabled and all the meds i;pm om give me hoit flashes i just want t be comforgtable and i kniow enms clothes r too thick need just some advice

  2. Michael says:

    I am just about to go in public as "Michelle" Full make up, skinny jeans, cami, sweater and wig. I don't want to brag, but holy s@#$t I look hot!

  3. Anonymous says:

    I see so many women do and it makes me mad. Wear something you feel comfortable in most women can tell the difference between girls and gurls. Honestly we do not care. In fact, most of us are jealous. You look better in our clothes too. Relax and have fun.

    virility ex

  4. Anonymous says:

    I see so many women do and it makes me mad. Wear something you feel comfortable in most women can tell the difference between girls and gurls. Honestly we do not care. In fact, most of us are jealous. You look better in our clothes too. Relax and have fun.

    virility ex

  5. jackreed says:

    Skinny jeans with flat shoes an oversized tank and some kind of gaudy jewlery and blacks and whites with a one bright loud color that makes your skin or hair standout.I started dressing up regularly as soon as I was old enough to left alone by myself–about eleven or twelve. It’s been a life long thing for me as far as I’m concerned.I was never caught in full dress but i was questioned on several occasions about why I had eye shadow on or make up that I did not take off properly.

    pokies

  6. jackreed says:

    Skinny jeans with flat shoes an oversized tank and some kind of gaudy jewlery and blacks and whites with a one bright loud color that makes your skin or hair standout.I started dressing up regularly as soon as I was old enough to left alone by myself–about eleven or twelve. It’s been a life long thing for me as far as I’m concerned.I was never caught in full dress but i was questioned on several occasions about why I had eye shadow on or make up that I did not take off properly.

    pokies

  7. ihave 3 days till i go on my date i need help looking foward to talk to you ginger

  8. I wished, and wish that i’m more feminine even when i was a kid own dresses, skirts, bra’s, and blouses too.

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