What to wear the first time you crossdress

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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Casey Casehttps://www.crossdresserheaven.com/wp-content/plugins/buddypress/bp-core/images/mystery-man.jpgPatty Phosehttps://www.crossdresserheaven.com/wp-content/plugins/buddypress/bp-core/images/mystery-man.jpgPatty Phose Recent comment authors
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Atef Anwar

This is a first time to wear a crossderssing. I prefer to wear high fitted neck or peter pan collar dresses with back button because my neck is thin and tall. I wear also a fitted bra and still in home alone and l am could not go outside.please what can I do?
thanks

Patty Phose
Duchess
Trusted Member

The first time I dressed fully fem, putting on pantyhose was no problem I had been wearing them for years. I wore heels because I liked how they made my legs look better. They did take some getting used to though. Makeup I needed a lot of help with. The dress was very comfortable. Padded bra, no issues there. A few different wigs and I decided on the long blonde one. Panties were worn over my sheer to waist pantyhose. I thought I looked terrible but I got a lot of compliments. It was a Halloween party and I was… Read more »

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Lovely1117

Just be you no matter what people say

Casey Case
Member

So much makes so much sense when I read it, just wouldn’t have thought of it on my own. After about a year of dressing up at home I feel I have moved into a different mindset. Not just putting on women’s clothes, but just like you wrote, wanting to look more feminine. I get how that feeling changed and guess it was inevitable looking over the last few months. I bought makeup for the first time yesterday. Application is much harder than I expected, at least I was able to laugh about it, the results were pretty hysterical, okay… Read more »

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