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I found an adult movie in my parents? closet when I was about 13. Watching it I found I was envious of what the woman riding cowgirl on the screen was feeling. I started dressing to imagine I was...

I was very fortunate. I have a sister 375 days younger than me. As girls develop faster than boys we were about the same build until late in high school. When I was 13 she left a bikini hanging in...

I know a young lady who is a professional poker player and an escort on the side. I want her life.

Is "Look like Christina Hendricks" a super power?

I have found that I am very heterosexual. When I am a guy, the idea of being with a guy is quite off putting. However, I dress to pretend I am a woman, with all the right parts, so when I am dressed...

First of all, thanks to everyone who has posted. Clearly, the best answer is "it varies." In my case, I started dressing because I envy women's bodies and sexuality. I am 100% straight, but when I...

I had an ex-gf put lipstick on me once. That is definitely a different sensation as the sensation of the makeup on your skin is something you can feel as long as it is on there, unlike rouge or...

Ann-Margret

She was smoking when she was in her twenties and is still @!$@# hot at 60.

Other than docrobbysherry as we've already communicated. I'm interested in asking some questions if anyone else here has one and is willing to take some more personal questions about wearing one.
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I'll tell you how I feel personally. As a guy I am completely grossed out by the idea of being physical with a guy. When I get completely dressed up and in the mood I feel a very strong desire to...

I was always partial to the little baseball sized balloons filled with water. I would double them so that a breakage wouldn't make a mess but I loved feeling the weight of the water plus seeing the...

Ohhh, Jessica. That would we wonderful.

Sticking with real life, I'd like to be Helen Hunt. Her or Jenna Jameson.

Sorry for chiming in so late...

I have to agree. When I am dressed up and can't see parts of me I normally can (like my feet) because of the additions to my chest my body simply quivers with...

I would absolutely choose #1. I dress not for the thrill of dressing but to get in the character of being female. I know I'll never be one but to be able to stand naked in front of the mirror and...

This is kind of amusing. I have always been able to fasten it behind me from the single hook 34A up to a four or more longline bra. My wife on the other hand does the "fasten in the front and...

I play trombone and have a fairly expensive instrument. It sits on a stand in our music room and so a nice, large supposedly empty case is downstairs in the basement. There is no reason to open the...

This conversation makes me realize what stupid things we do in our youth. I have an ex-gf who not only accepted my CDing, she'd have sex with me pretending I was female and even wake me up in the...

That's pretty impressive, although I'm hoping someday to get a v-string. The idea of feelings my own vaginal lips, even if fake, makes my heartbeat quicken.

Mine is the name of a girl I dated that I thought was the cutest girl I've ever known. If I could magically be female I would want to look just like her, with the only possible alternate exception...

I have a few:


The white strapless dresses worn by Jennifer Connelly in "The Rocketeer" and Kim Basinger in "Batman."
Anything worn by Charlize Theron in "Aeon Flux."
That V neck red dress...

I like my wife to wear stuff I could never get away with. Tight high waisted jeans, demi bra and a tight white t-shirt. I like the "slinky" lingerie for me, on her I want to see the thin waist and...

I don't have a favorite right now since I can't CD but my past favorite was my sister's white strapless sundress I wore in high school. I'd put it on with her well padded longline bra and I'd look...

I remember trying on my Mom's pantyhose when I was 5 out of sheer curiosity about this clothing that my mom wore that nobody else in the family did. Fast forward several years without any kind of...