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July 2009

Mariah Carey

Mainstream Crossdressing: Mariah Carey 2

July 22, 2009

This is just a follow up to the original post where I shared two of her pictures from the Obsessed video. It has now been released and you can watch it by clicking below . . .

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wall

How to Beat Crossdresser’s Block

July 21, 2009

Last week, we talked about crossdresser’s block – a phenomenon that most of us have experienced on our way to expressing ourselves. Frankly, I’m sick and tired of letting my insecurities and doubts get the best of me and I hope to spread this message by sharing what I’ve learned. The consequences of not dressing [...]

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wig

Whose Wig is That?

July 20, 2009

A stressful but otherwise uneventful weekend was interrupted by a phone call from my wife. At the moment, I am packing our belongings as we finalize our cross-country move. Her sister came to visit for the weekend, and I figured that they would have a terrific time together; I had no idea what was in [...]

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cake

Three Month Commemoration

July 20, 2009

I would like to take the time to commemorate three months of blogging at Jessica Who?, it has been a tremendous experience so far. None of this would have been possible were it not for the following people.

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brian griffin

Mainstream Crossdressing: Family Guy

July 17, 2009

There have been plenty of crossdressing moments in Family Guy, and this is one of the more memorable ones. I find it hilarious because it represents the tension and awkwardness between two friends when one finds out the other is a crossdresser. I especially love how Brian is reciting all of his “womanly” chores for [...]

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chain

Breaking the Chains

July 16, 2009

A big part of being a transgendered person is rejecting many of societies’ rigid stereotypes in favor of individuality. I’ve always taken great pleasure in this, daring to be unique for most of my life regardless of what others have to say about it. When I was at the airport yesterday, waiting for my flight [...]

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question

Why Aren’t We Dressing More?

July 15, 2009

Life is busy and sometimes it can seem that you never have any time just for you. Responsibilites and tasks pile up, leaving you frantically moving from one obligation to the next. This means cutting everything that isn’t absolutely necessary. However, this can take a toll on your emotional well-being. We must strive to do [...]

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