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Classy Crossdresser

Category Archives: Crossdressing

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The Power of Perfume and Its Role for a Crossdresser

Classy Crossdresser Posted on February 14, 2025 by Jenn der BentsonMarch 1, 2025

By Jenn der Bentson Crossdressing is a deeply personal and expressive journey, where every detail matters in crafting an authentic and fulfilling experience. From the right outfit to the perfect makeup, everything contributes to presenting the desired feminine image. One … Continue reading →

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Classy, Reserved, and Professional Crossdressing

Classy Crossdresser Posted on February 13, 2025 by Jenn der BentsonMarch 1, 2025

By Jenn der Bentson Crossdressing is a powerful form of self-expression, allowing individuals to explore their identity and present themselves in a way that feels authentic. While some enjoy bold and extravagant styles, others may seek a more refined, polished, … Continue reading →

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The Benefits of Crossdressing as a Stress Relief Tool

Classy Crossdresser Posted on February 11, 2025 by Jenn der BentsonMarch 1, 2025

By Jenn der Bentson For anyone, stress can be something from with they want to find release. Stress is an unavoidable part of daily life. It may come from work pressures and social responsibilities to personal expectations, family challenges, or … Continue reading →

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The Hidden Market: Why There Are More Crossdressers Than You Think

Classy Crossdresser Posted on February 2, 2025 by Jenn der BentsonMarch 1, 2025

By Jenn der Bentson Crossdressing, the act of wearing clothing and adopting the appearance typically associated with the opposite gender, has been practiced by individuals throughout history. While it is challenging to quantify the exact prevalence of crossdressing, there are … Continue reading →

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Why Crossdressers Make Better Husbands

Classy Crossdresser Posted on January 31, 2025 by Jenn der BentsonMarch 1, 2025

By Jenn der Bentson When people think of an ideal husband, they often envision someone who is loving, understanding, and supportive. What if we told you that crossdressers, often misunderstood and misrepresented, can make some of the best husbands? While … Continue reading →

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My Four Go-to Pairs of Shoes as a Crossdresser [On Amazon]

Classy Crossdresser Posted on January 25, 2025 by Jenn der BentsonMarch 1, 2025

By Jenn der Bentson Shoes are one of the things that any crossdresser associates with more feminine expression. There is no doubt that many women have a variety of shoes that they wear with different outfits, for different occasions, or … Continue reading →

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The Power of Crossdressing: A Transformative Experience for Heterosexual Men

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

By Jenn der Bentson Crossdressing, the act of wearing clothes traditionally associated with a gender other than one’s own, has long been misunderstood and stigmatized. However, in recent years, society’s perception of gender expression has become more inclusive and nuanced, … Continue reading →

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The Best Breast Form Options I Have Tried and Recommend

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

By Jenn der Bentson Picking breast forms can be challenging in the beginning. There are so many options to choose from, and so many “features” and such a large price range. It can feel like you are just guessing and … Continue reading →

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Crossdressing as a Hobby: Exploring Passion, Creativity, and Expression

Classy Crossdresser Posted on January 23, 2025 by Jenn der BentsonMarch 1, 2025

By Jenn der Bentson Hobbies are an integral part of human life, offering opportunities to explore interests, develop skills, and find joy outside of daily routines. From gardening to gaming, people engage in hobbies to relax, express themselves, or even … Continue reading →

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Breaking Down the Barriers: Understanding the Lack of Respect Towards Crossdressers

Classy Crossdresser Posted on January 23, 2025 by Jenn der BentsonMarch 1, 2025

By Jenn der Bentson In today’s world, diversity and acceptance have become integral parts of our social fabric. However, despite significant progress in promoting tolerance, there are still instances where certain individuals and groups face an unfortunate lack of respect. … Continue reading →

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Exploring Why Many Crossdressers Don’t Come Out Until Later in Life

Classy Crossdresser Posted on January 22, 2025 by Jenn der BentsonMarch 1, 2025

By Jenn der Bentson Crossdressing, the practice of wearing clothing traditionally associated with a gender different from one’s own, has long been a subject of intrigue, misunderstanding, and stigma. Many individuals who identify as crossdressers find themselves coming out later … Continue reading →

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5 Things Crossdressers Commonly Waste Money On

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

By Jenn der Bentson Crossdressing is a journey of self-expression that allows individuals to embrace their authentic selves. While there is a wide range of products and accessories available, it’s essential to differentiate between essential items and potential wasteful expenditures.  … Continue reading →

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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 wpusername5311March 1, 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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Newer posts →

Recent Posts

  • Facing the Mirror – Shame Acceptance and Avoidance in the Life of a Crossdresser
  • The Hidden Cost of Suppression: Why Denying Your Crossdressing Desires Can Do More Harm Than Good
  • Let’s Talk About It: Why Society Needs More Open Conversations About Crossdressing
  • Unapologetic Desire: Reclaiming Pleasure and Freedom in Crossdressing
  • Crossdressing and the Brain: The Psychological and Physiological High of Crossdressing
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