Cross-dressing

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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Posted on the Jan 04, 2011 by Carlin Ross
I'm in love.  This video is so erotic.   Combining an audio interview with video of his modeling sessions has me wanting more. Meet male model Andrej Pejic - he models both male and...