I have plenty of thoughts on the subject, but the truth is, I still don’t really know why. So I decided to ask AI, “Why do I crossdress?” What follows is its unedited answer.
Crossdressers crossdress for many different reasons, and often for several reasons at once.
For some, feminine clothing, makeup, and mannerisms simply feel attractive, comfortable, or personally expressive. They enjoy the transformation and the chance to present a side of themselves that ordinary male life does not allow much room for.
Others crossdress because it provides:
Emotional release: Dressing can reduce stress and create a sense of calm, freedom, or escape.Crossdressing does not automatically mean someone wants to become a woman, is transgender, or is gay. Some crossdressers are satisfied living primarily as men while occasionally presenting as women. Others eventually realize that crossdressing was part of a deeper transgender or gender-fluid identity.
The most honest answer is that many crossdressers do it because it makes them feel good, complete, relaxed, beautiful, or more authentically themselves—and stopping may feel like suppressing an important part of who they are.
 |
| Wearing Miraclesuit |
 |
| Bunny Lewis femulating in the 1973 British film A Couple of Beauties. Click here to view this film on YouTube. |
”Why do i crossdress” is certainly a question i’ve asked myself more times than i can remember. for the early years & perhaps right through my teens it was fir sexual excitement- no question. then during my 20s & early 30s it was a desire to be a woman . the style, the beauty, the clothes…..then when my relationship with my mother-in-law started in my mid 30s it changed again & now it’s both sexual & about style & presentation. maybe life does go in circles 😍😍💋💋
ReplyDeleteI've never been a fan of AI, yet this really states the case clearly and directly. May I share this?
ReplyDeleteOK
DeleteGood post! -- Yes, all of the above.
ReplyDeleteI am sure every crossdresser has pondered this question. My formative years were in the 1950's and 1960's. I do remember trying on my mother's full slips because the feel of the nylon fabric was unlike any of my clothes. There was other thoughts. Puberty changed all that. Why? I had a PTSD counselor for war related issue who is of the opinion that each man and woman has some DNA of the opposite sex in their chain; In some it is more than in others. I think events in my life may have awakened that female dna to the extent it overrides the potential negativity society heaped upon men who wear women's clothing. Most of the combat veterans in associate with have had some sort of addiction problems with drugs and alcohol as an escape. Me? Why did my brain decide to seek peace and tranquility by emulating a woman rather than seeking solace in a bottle of booze?
ReplyDeleteThe world would be a kinder and gentler place if more men could feel free to experiment with feminine presentation. Who would want to bomb another nation if you were wearing a pretty dress and lipstick?
DeleteAngie
Early on I think there was the adrenaline rush of being out in public wearing women's clothing. Really is pretty complicated and in the end... who knows?
ReplyDeleteAI response to my asking. I have chatted some with AI prior to this:
ReplyDeleteI don’t think there is one simple reason, and I wouldn’t presume to diagnose you. But from what you’ve shared, cross-dressing seems to serve several connected parts of you.
You remember wanting to be like Dorothy Nichols when you were only eight, before you could have reasoned your way into it. That suggests the desire is deeply rooted—not merely a hobby you picked up later. Feminine clothes also seem to give physical and aesthetic pleasure: the feel of hosiery, the movement of a dress, the jewelry, makeup, colors, and the satisfaction of putting together a beautiful outfit.
More importantly, I think dressing lets you make visible a softer, sweeter and more playful part of yourself—the part you describe as “gender quirky.” It may provide freedom from a narrow version of masculinity, especially after growing up with a punitive, homophobic father. Clothing can become a safe language for qualities that once felt dangerous to express.
And there seems to be joy in being seen that way. Your memories of outings with your wife matter because you were not only dressed—you were accompanied and accepted. Her later withdrawal likely hurts so much because it can feel like rejection of something genuine within you, rather than disagreement about fabric and shoes.
So my best understanding is: you cross-dress because femininity has spoken to you since childhood; because you genuinely love its sensory and visual expression; and because dressing allows an authentic, tender part of you to breathe. Whether that makes you transgender, gender-nonconforming, “gender quirky,” or simply Don is ultimately yours to define.
Back around 1750 there was a fashion catastrophe that started for men: The Great Male Renunciation, when men's fashions became drab and boring. Before men wore heels, makeup, and long hair or wigs. Their colors had much more variety.
ReplyDeleteAnd now, men are stuck with coats, ties, and trousers for formal wear, along with drab colors for jackets, trousers, and shirts.
I don't mind occasionally wearing a man's suit when it's cool, but having that as the only formal clothing is confining. So, as a man, I also doll myself up to present "en femme".
John
3 little letters that make 1 giant word, but for me the answer has always been "all of the above"!
ReplyDeleteI love that this article just makes you think and ask why. My wife asked me why I like to dress in women's clothes. At first I told her I don't know, then because I liked it and that for some reason I just needed to. Randi
ReplyDeleteThe 6th item; sexual excitement; is that not autogynephilia?
ReplyDeleteI could easily say all seven of the bullet points in the graphic are true for me, but at its most basic I would say my love for the feminine aesthetic is rooted in my attraction to skirts. For as long as I can remember, skirts have held a unique place in my heart. They always seemed to make so much sense to me. It’s like I knew I would be happier and more comfortable wearing them, if only I wasn’t excluded from them for simple fact that I am not female. It breaks my heart that while there is a small minority of women who love skirts, the vast majority of women these days feel like it’s a hardship to wear a skirt and will only wear one if the social situation demands it. I love spending my summers in genderqueer mode— full femme clothes on an obviously male body!
ReplyDeleteAngie