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User / Helene Barclay 1 / Sets / Cross-dressing 2002
Helene Barclay / 21 items

N 24 B 83.2K C 25 E Feb 1, 2002 F Jan 24, 2013
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I no longer go out as a woman. My forays into the world were brief. This photo was my first time ever in February 2002 and within five months I was firmly back in the closet never to venture out as a woman again. A short lived experience that I found anything but enjoyable, I lacked the self belief that I could look realistically female and as a result my confidence was shaken for many years afterwards.

Tags:   transvestite crossdress t-girl transgender transsexual transexual t-gurl gurl drag transvestism transsexualism female impersonator female illusion male to female female impersonation tranny trannie trans queen drag queen ladyboy third sex glbt m2f m to f crossdressing crossdresser gender homosexual gay lesbian effeminate boy to girl acting performance wig makeup dressing up as a woman men who dress as women dressing up men dressed up dressing up

N 68 B 131.8K C 43 E Dec 19, 2012 F Dec 19, 2012
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A picture from early period of cross-dressing taken in July 2002. Despite a lifetime of wanting to dress as a woman and spend time as a female I was too terrified to engage in my transvestite desires. In November 2000 I finally summoned up the nerve and so my female alter ego was born. I won't deny I love becoming a woman and thrill in the experience of wearing make-up, wigs and women's clothing such as lingerie, dresses, skirts, blouses and high heels. To be honest, it feels like this is how it should always have been but of course I am a man and live as a man so I see it as an indulgence and a form of female impersonation as alas I know I am not a woman. Dressing up is as close as I will ever come.

Make-up artist Jodi Lynne did my make-up and hair (wig) and the photograph was taken by Mike Pattinson.

Tags:   transvestite crossdress t-girl transgender transsexual transexual t-gurl gurl drag transvestism transsexualism female impersonator female illusion male to female female impersonation tranny trannie trans queen drag queen ladyboy third sex glbt m2f m to f crossdressing crossdresser gender homosexual gay lesbian effeminate boy to girl acting performance wig makeup dressing up as a woman men who dress as women

N 43 B 122.0K C 22 E Jul 1, 2002 F Aug 20, 2012
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I have to admit I really do like being a woman. Of course I can never really know what it's like to be an actual woman as I'm a transvestite but I do find a high degree of comfort and contentment within myself when I put on makeup, a wig and dress in women's clothing. I really do like it and I find it easy to leave the man behind.

Tags:   transvestite crossdress t-girl transgender transsexual transexual t-gurl gurl drag transvestism transsexualism female impersonator female illusion male to female female impersonation tranny trannie trans queen glbt m2f m to f crossdressing crossdresser gender gay lesbian effeminate boy to girl acting performance wig makeup dressing up as a woman

N 60 B 73.2K C 18 E Sep 1, 2002 F Aug 13, 2012
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One of my early cross-dressing looks, a self timer shot from Autumn 2002.

Tags:   transvestite crossdress t-girl transgender transsexual transexual t-gurl gurl drag transvestism transsexualism female impersonator female illusion male to female female impersonation tranny trannie trans queen glbt m2f m to f crossdressing crossdresser gender gay lesbian effeminate boy to girl acting performance wig makeup dressing up as a woman

N 17 B 63.5K C 18 E Feb 1, 2002 F Aug 8, 2012
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Another picture from my recently rediscovered archives charting my cross-dressing progress.

This picture is rather special as it was the first time I ever ventured outdoors dressed up as a woman. It was late in the afternoon on a cold February day back in 2002 and I felt on an incredible emotional high. I can still recall it now over a decade later!

I attended a transvestite social evening at 'Hide & Sleek' in Fife, Scotland. It was the first time I traveled as a woman for a few hours and actually met others who like me feel an inner desire to dress and spend time as women. I was still inept at applying makeup, wigs and trying to get a female look but I was very excited at finally escaping my repressed dreams of cross-dressing.

Tags:   transvestite crossdress t-girl transgender transsexual transexual t-gurl gurl drag transvestism transsexualism female impersonator female illusion male to female female impersonation tranny trannie trans queen glbt m2f m to f crossdressing crossdresser gender gay lesbian effeminate boy to girl acting performance wig makeup dressing up as a woman Next suit


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