Cross-dressing

Posted on the May 28, 2013 by Carlin Ross
*sigh* Marion Cotillard by Sebastian Kim
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Posted on the May 06, 2013 by Betty Dodson
Dearest Betty, My masturbation technique is in you book "Sex for One" as "Larry S. from Poughkeepsie" a fictious name...I sent you a VHS video also in the early 1990s of me masturbating by stroking a...
Posted on the Apr 29, 2013 by Carlin Ross
This is a picture of Barbette - an acrobat, drag queen and contemporary of Man Ray, Jean Cocteau, Josephine Baker, and Picasso. Barbette was born Vander Clyde Broadway in Round Rock, Texas in 1899...
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Posted on the Mar 20, 2013 by Carlin Ross
I found this image on reddit and had to post it here. Love love love his boots.
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Posted on the Mar 03, 2013 by Carlin Ross
I love unearthing feminist history. Turns out many women dressed as men and fought in the Civil War. Here is Frances Clalin - a mother of three from Illinois - who fought as Union cavalryman Jack...
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Posted on the Feb 15, 2013 by Carlin Ross
God, I love Alicia Silverstone as a man.  1995 Photographer : Frederique Veysset
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Posted on the Oct 27, 2012 by Carlin Ross
I find the juxtaposition of masculine and feminine extremes utterly erotic. And his legs look great in heels...
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Posted on the Sep 14, 2012 by Betty Dodson
Hello, Dr. Betty! I'm 21, female, and a huge fan of your work. Ever since I found out about you and your website, my life has been completely transformed. Words cannot express how thankful I am for...
Posted on the Aug 25, 2012 by Carlin Ross
There really is nothing new under the sun.
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Posted on the Aug 13, 2012 by Carlin Ross
I found this pic on a vintage tumblr site.  It was posted by the great grandchild of the woman dressed like a man - seems she liked dressing up on occasion. I thought it was sweet that they...
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Posted on the Jun 07, 2012 by Carlin Ross
This painting of Chevalier d’Eon a middle-aged cross-dresser is the first painting of its kind to be hung in the revered National Portrait Gallery.  D'eon was an eighteenth-century diplomat...
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Posted on the Sep 21, 2011 by Betty Dodson
I am a crossdresser. My live-in wife is comfortable with it and loves to play along. Actually it was her idea in the beginning. It started with me having a high heel fetish. She suggested that I try...
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Posted on the Jul 24, 2011 by Betty Dodson
Betty, Hi. I am dating a guy that wears panty hose. It is pretty weird to me. We have been dating for six months, and it has really bothered me lately and I don't know how to tell him. He told me...
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Posted on the May 03, 2011 by Dr. Lulu
To our Western way of thinking of gender, we seem to embrace a two-party system. Many cultures around the world leave room for more diversity and in some cases make room for a third gender — even a...
Posted on the Apr 08, 2011 by Carlin Ross
Miss Vera is teaching her Spring class on How to Walk, Sit & Pose in High Heels.  Miss Vera is a woman like no other.  She's a dear friend of Betty's, she's all over the media, and she...
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