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Classy Crossdresser

Author Archives: Jenn der Bentson

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The Complex Controversy of Crossdressing in the LGBTQ+ Community

Classy Crossdresser Posted on January 10, 2025 by Jenn der BentsonMarch 1, 2025

By Jenn der Bentson Crossdressing has long been a contentious topic, not only in broader society but sometimes it is also within the LGBTQ+ community. While some embrace crossdressing as an expression of identity, fashion, or artistic freedom, others view … Continue reading →

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How to Avoid Purging. Strategies for Cleaning out Cloths and Other things for the Crossdresser

Classy Crossdresser Posted on December 20, 2024 by Jenn der BentsonMarch 1, 2025

By Jenn der Bentson Ok, so I admit it. I buy too many clothing articles for Jenn. I and others will argue that wearing the clothes, the makeup, the breast forms, and all that comes with my crossdressing is part … Continue reading →

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Breastplates and Bodysuits, Oh My

Classy Crossdresser Posted on October 20, 2024 by Jenn der BentsonMarch 1, 2025

By Jenn der Bentson Wow. Breast plates and crossdressing bodysuits look like great fun with lots of cool options. They seem really amazing when you look at them on the internet. What crossdresser wouldn’t want to just slip into a … Continue reading →

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Do I Cross-Dress Sexy Because My Wife Doesn’t?

Classy Crossdresser Posted on September 20, 2024 by Jenn der BentsonMarch 1, 2025

By Jenn der Bentson Crossdressing can be a tough topic. It can be tough to understand and that is no different for me, especially when I try to understand why I do it. There are times that I like to … Continue reading →

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All Those Options for Breasts

Classy Crossdresser Posted on July 20, 2024 by Jenn der BentsonMarch 1, 2025

By Jenn der Bentson Oh the wonderful thing, breasts. Many of us would love to have them for real A few lucky crossdressers or, more commonly, transgender individuals get to have them at some point as they make transitions. My … Continue reading →

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Sexy As a Girl

Classy Crossdresser Posted on April 20, 2024 by Jenn der BentsonMarch 1, 2025

By Jenn der Bentson “I just feel sexier when I am dressed as a woman,” I expressed to her “Guys just aren’t sexy, and when we have sex, I feel like I want to be sexy sometimes.” It was kind … Continue reading →

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I Love Tits, What Crossdresser Doesn’t?

Classy Crossdresser Posted on March 24, 2024 by Jenn der BentsonMarch 1, 2025

By Jenn der Bentson I Love Tits.  What Crossdresser Doesn’t? It’s simple. I love how they look on women, and as a crossdresser, I have no doubt that it is somewhat out of jealousy that I love to put them … Continue reading →

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When it comes to crossdressing, just at home is OK

Classy Crossdresser Posted on February 19, 2024 by Jenn der BentsonMarch 1, 2025

By Jenn der Bentson So, there are lots of questions when it comes to crossdressing. One that comes up sometimes is should it be a goal to leave the house in your crossdressed state? Crossdressing can be a lonely thing. … Continue reading →

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Why We Want to Go Out [as Crossdressers]

Classy Crossdresser Posted on January 19, 2024 by Jenn der BentsonSeptember 17, 2025

By Jenn der Bentson Being a crossdresser is something that most of us, if not all, at least sometimes, are embarrassed of being. For the overwhelming majority of crossdressers, there is a period, for many a very long one or … Continue reading →

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