A Cisgender Woman’s View of Crossdressing

For several years before I launched my website and blog in 2021 I had been writing the story in my head, mostly during long sleepless nights. It became a coping mechanism and a form of self-therapy to deal with the unexpected impact and sometimes devastating consequences of being married to a man who not only immersed himself into the secret world of crossdressing but other clandestine sexual pursuits.

Within days of meeting Bill on an online dating service, he revealed a fancy for wearing thong underwear, toe rings, a strong preference for role-playing, and being dominated during sex, often referred to as a “sub.” Only after passing the initial tests to gauge my acceptance of his likes did he take the bold step to disclose he was a full-blown crossdresser. He showed me his collection of high-heeled stripper shoes, thigh-high stockings, a wide array of lingerie, and his collection of sex toys designed to be worn by a woman to engage in “pegging.” It must have been a terrifying gamble for him to undertake, not knowing what my reaction would be.

I was undoubtedly shocked, confused, and uncertain about how to proceed with this revelation. What did it mean to be a crossdresser? Why did he do it, and when did it start? How in the hell did a brawny SWAT cop who retired as a Commander get into this bizarre fetish? Was he gay? So many questions and so few answers.

I spent hours scouring the internet for information and answers to questions that really had no answer. It was an education on a topic I never thought I would want or need, but I concluded that there was no harm in it, and I didn’t see any reason to stop seeing Bill simply because he liked the way feminine lingerie made him feel. Bill only casually denied being interested in men and claimed he long ago explored the question of whether he might be gay and decided he was not. (Later, I would conclude differently.)

His obsession with feminine clothing appeared to be a private fetish and not something he wanted to do in public, so I not only accepted his passion, but I enthusiastically encouraged and participated in it by picking out his outfits, buying him sexy panties, and incorporating the whole thing into our sexual activities. Bill’s dressing and sexual preferences to engage in dom/sub-role-playing became the center of everything we did in the bedroom. At first, it seemed fun, quirky, and harmless adult play — at times immensely erotic. However, I didn’t realize that to Bill, it was serious business that had become the foundation of a more dangerous addiction.

Not every significant other knows the man in her life is a crossdresser, much less accepts and participates in the pastime. There are vastly diverse degrees in which men engage in the pursuit, which may influence whether a significant other is willing to approve of it or how much. Some women shamelessly go out in public with their feminine partner, who is all dressed up and ready to face the double-takes, snickers, and whispering. Other women head for an attorney prepared for battle at the first discovery of hidden lace panties. Many of us land somewhere in the middle.

I believe that having knowledge about something is not the same thing as understanding it. My unexpected introduction to this secret world in 2014 started with a whisper of knowledge. However, as much knowledge, acceptance, and understanding as I have gained, I still struggle to fully comprehend what drives this deep-seated craving.

Through my website and joining online CD/TG sites, many crossdressers and transgender people have opened up to me about their voyage. It has afforded a tremendous insight into this rare community, encouraging my journey from knowledge to understanding. However, there is so much more to learn and comprehend.

I mean no offense to this rare community we belong to, and I know that my experiences certainly do not reflect every situation that CDs or their significant others confront. Unfortunately, I have met women who have endured similar incidents as I have. While sad, I also find inspiration and resolution in their stories, and I hope you will find the same in mine.

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Tags: crossdressing, featured, Identity

Category: crossdressing