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Why We Cross-Dress. The Facts of the Fiction.

by Trish Murray 23 Jan 2023 0 Comments

The art of Cross-Dressing has been around for centuries, as have the life of cross-dressers.

But what’s the deal with it, why is there stigma to it, and why do people who cross-dress for pleasure still get the sticky end of the lollipop of life. Well, we are going undercover to investigate, and find out what is behind the myth that is cross-dressing. 

In this post we will be looking at the man that likes to dress as a woman, and the perspective we project about this pastime.

The Origin?

Cross dressing has been around for centuries, Shakespeare had many a cross-dresser in his plays, and did it raise an eyebrow back then, of course it didn’t.

But fast forward to the 1970’s, and we were presented with the idea that a man dressing as a woman was comedic, laughable or worse, ridiculous. Dick Emery and Stanley Baxter were 2 of the biggest comedians of the day, and they were, along with others, donning many a frock for comedic value on prime-time TV, adding to this subconscious thought that a man in his wife’s clothes was something to be laughed at or ridiculed. In the past, and still sometimes today, cross-dressing has ended marriages and cost many a man his friends, family and even job.

So why do we do it, what fulfilment do we get from dressing as a woman. Well, simply put, cross-dressing allows the individual to, for a brief time, live in the gender of the form he most desires, loves and is aroused by and fascinated with.

Societies Double-Standards

I know as a child I had a Fireman’s outfit and was encouraged to dress up as often as I wanted to, because my uncle was a fireman and I admired him in the way a boy admires his hero, his uncle, a man he loves; and that was fine to do, welcomed in fact.

But if it was an Auntie, who was a nurse, a job as equally demanding of our respect, I’m not quite sure my parents would be encouraging me quite as much if I wanted to dress as a female nurse, showing my admiration of the woman and her work.

So, the truth behind it all is purely logical captain. It is the wish to be the gender we desire and admire, is aroused by and loves. So why should we not encourage the man who likes to dress as a woman for his personal enjoyment as my parents did the boy who wanted to dress as a fireman for his. What right have we to say one is right and one is wrong, one is fun and one is perverse. None, as both are a freedom of expression, a desire to inhabit a lifestyle that we find pleaser or joy from.

The Freedom of Gender

Cross-Dressing has taken so many forms over the years, no more so than in art and fiction. Great authors thread stories of intrigue and deception, love and romance; with male and female protagonists taking you on a journey of danger and passion. All brought to you from the mind of the author. Do they not mentally take the form of each character as they wright their whole life onto a page. And don’t get me started on the Great Masters, with paintings of boys in dresses and men in wigs.


Though we are born into a gender, who has the right to say that is the only gender we are allowed to experience, and transvestism allows a man, or woman to experience that freedom of gender. In a world that is more accepting of gender fluidity, with more and more individuals choosing a pronoun that suits their mind rather than their body, who are we to stop a man if he wishes to feel the breeze on his shaven, stocking covered legs, below a beautifully pleated skirt, or to wear heals to the office should he wish. If he wishes to dress and Be a Lady, who has the right to say no, this is not normal, this is not right. No one.

Just because you don’t want to do it, to feel what it is like to experience the gender you admire and love, it shouldn’t scare you. We live each day accepting things, things that change on a daily basis, and change things when we want to do something else. We accept that it will get dark at night, but we turn on a light, to live a different life, a normal life, a night life.

I will leave you with this; Cross-Dressing is as normal as turning on a light, the only thing that makes it uncomfortable for some, is that they have only ever lived in the dark.

Love Team Nice 'n' Naughty x

Check out our Cross-Dressing range here.

Check out our Transgender range here.


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