Guest Blog

Guest Blog: Fetish Spotlight: Cross-Dressing

Ally Amour Phone Kelly

Cross-dressing has always fascinated me, due to its complex, barrier breaking and sensory connotations and expressions. This gender defying journey ranges from the occasional indulgence to a full life style practice.

Let’s dive in, shall we?

The practice of cross-dressing has been recorded throughout history and in modern times. Cross​-​dressing​ has been used for purposes of disguise, comfort, and self-discovery. The act and practice of cross-dressing has been around since early man ditched the loincloth and created diverse garments to enhance gender differences which were assigned to each gender in different societies.

Many assume the act of cross-dressing is an indicator of the cross-dresser’s homosexuality or transgender inclination. This isn’t always the case and the act of cross-dressing may have very little to do with a person’s gender identity.

I’ve experienced a fine example of this with one of my callers, a 62-year-old Native American man who loved dressing in female garments down to the very last detail. He immediately clarified that he was not attracted to other males. He loved women and always had. His cross-dressing practices started as a young teen and advanced as he got older.

He told me that amongst indigenous North Americans this practice had a specific term: ​TWO-SPIRIT, also referred to as Twospirited.​ This was umbrella term used to describe a third gender variant for individuals that fit this role. Decidedly, the “Two -Spirit” is NOT interchangeable with “LGBT Native American” or “Gay” definition.

The Two-Spirit is in fact a title which differs from most western or mainstream definitions of sexuality and gender identity. It’s considered a sacred, spiritual and ceremonial role that is recognized and confirmed by the Elders of the Two-Spirit’s ceremonial community. It is not so much about whom one is sexually interested in, or how one personally identifies.

I often see, in my personal engagement with many of my cross-dresser callers, that their practice may be just as complex and in many instances, hidden from their loved ones and spouses. As a Mistress, I take great delight in educating and guiding my wide range of cross-dressing clients in the glorious eclectic history of such practice. I want them to never be embarrassed of their need to indulge in cross-dressing play. My callers are a part of a great tradition indeed!

Cross-dressing in​ Ancient Scandinavia​: According to Norse mythology, Thor and Loki were two of the earliest cross-dressers known to man. Nobody knows the exact year that Icelandic people began telling this story. It wasn’t written down until the 11th century CE, but its oral equivalent has likely existed for hundreds…even thousands of years.

Cross-dressing in ​Elizabethan England: ​Only thirty-eight of Shakespeare’s original plays survive today. Out of those thirty-eight plays, seven feature cross-dressing characters: The Merchant of Venice, As You Like It, Twelfth Night, Cymbeline, The Two Gentlemen of Verona, The Taming of the Shrew, and The Merry Wives of Windsor.

Most often, it’s a female character adopting male clothing and mannerisms. She usually cross-dresses for protection, as it wasn’t safe for a woman to travel alone in Shakespeare’s day. These characters tend to exist in a type of third gender category between male and female.

Cross-dressing in ​North America:  ​Two-Spirited is a blanket term many indigenous North Americans use to refer to individuals who subscribe to neither traditionally male nor female gender roles. While male Two-Spirits were more common, there is documented evidence of both male and female Two-Spirits in more than 130 North American tribes across every region.

Generally, there were four agreed upon genders: masculine men, feminine men, masculine women, and feminine women. Feminine men and masculine women were Two-Spirited. They were able to wear both male and female clothing depending on their personalities, skills, and personal preferences. They could also participate in male and female activities and take either male or female partners. It wasn’t common practice for Two-Spirits to have relationships with other Two-Spirits.

Cross-dressing in ​Modern South-East Asia: Sex tourists everywhere are familiar with Thai ladyboys or kathoey. While the term “kathoey” was originally used in reference to intersex people, it now refers to a person who self-identifies as male but adopts female dress and mannerisms. There is a huge range in the type of dress and behavior exhibited by kathoey.

I love exploring the many versatile sides of cross-dressing and gender identity boundaries.
My long-term crossdressers callers love how deeply we can dive into this fantastic, alluring and complex world. Many new cross-dressers feel great joy with me guiding them further in understanding and incorporation of this passion and the artful play of cross-dressing, both in their everyday lives and behind closed doors. This is your life…Live it boldly and beautifully!

I hope you’ll drop by and tell me your cross-dressing story and adventures soon!

Call Mistress Ally Amour at 1-866-460-7399 ext. 8213!

*​Sources ~ Wikipedia, Allthatsinteresting.com, Willis World, Malaysia Flip Flop

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