Before we jump in, let’s talk about what crossdressing is.  To me, crossdressing is wearing clothes that are traditionally associated with a different gender.  A boy wearing a dress, a girl wearing a necktie.  That’s really about it.  I do not think clothes are, should be, genderized.  They are simply clothes.  If they fit, you can wear them.  It’s pretty simple.  I believe people who identify as a crossdresser fall under the transgender spectrum.

Passing… it seems like the holy grail for crossdressers. If we could work hard enough, lose that extra pound and practice voice lessons for another hour – maybe, just maybe we could pass as a woman. In our minds we’ve build up passing as something elusive that is to be dreamed about and never achieved.

The size of bust you want should be determined by factors such as body shape and size, type of clothes you will be wearing, your personality and your intended objective when dressing. For example, if you wish to ‘pass’ as realistically as possible as a woman then you should purchase breast forms which are proportionate to your actual body size.

Choose a padded bra with underwire support for a firmer bust. Many padded and push-up bra styles feature substantial amounts of molded foam padding. Select this style if you want the appearance of a larger chest. If you’ll be adding breast forms, pick a bra with underwire support to help lift and hold the forms in place.

If you’re a man looking to crossdress as a woman, a well-fitting bra can not only provide the right foundation for your clothes, but it can also help you connect with your femininity on a physical and emotional level. When you look for a bra, don’t let the sizing codes and the endless variety of styles overwhelm you. Start by taking some basic measurements to help you find a band size that fits comfortably around your ribcage. Then choose whatever cup size you’d like and try out breast forms or padding to achieve your ideal bust size. Have fun finding your favorite cut and style, and feel free to experiment with different bras as you embrace your new curves!