There are innumerable theories about why many men have a compulsive need to crossdress, to wear the clothes of women, to wear women’s lingerie and hose, to use waist cinchers, hip pads, and especially expensive artificial breasts (silicon masterpieces, preferably with subtly-erect nipples, held in cherished bras, chosen to be in perfect proportion to their bodies, bodies from which those breasts slowly take on their body’s own heat), to find ways to tuck away and hide their genitals, creating, at the place where their legs meet their bodies, convincing, little, slightly-rounded, pubic triangles under their panties, to do whatever they can to reshape their male contours into the contours one would expect of a woman, often to find ways to go out in public, to present themselves to the world as women.
They practice their voices. They become adept at makeup and hairstyles. They learn not to sway their hips artificially, but still to walk with a woman’s gait that somehow does make their skirt hems sway back and forth at their knees. It becomes second nature to them to hold their right hands slightly away from their bodies, letting them swing forward naturally with their left shoulders at each left step, while their left hands, with their fingernails long, manicured, and brightly polished, hold the straps of their shoulder bags. And delicate bracelets tinkle on their wrists.
They learn to stand erect, to smile easily. They find a fashion style in which they are comfortable, a style that is as personal and varied as that of all women. After some time, they learn to use shades of foundation and blush to highlight their cheekbones, to contour their faces using a skill that is realized by its imperceptibility. When their eyes blink, they expect the mascara on their lashes to bring attention to their fullness and length. Applying lipstick to their lips never stops being a sensuous delight. And brushing lint from their own breasts is forever felt as an honor.
They smooth their pleated skirts under themselves as they sit down. To adjust their earrings they cock their heads so their hair falls away. When they cross their legs, they are sure to keep the wrapping tight, even hooking their foot behind their ankles. At a street corner, while waiting for a light to change, they’ll shift all their weight on to one foot, letting the other foot be so light that its stocking-covered heel might even come out of its pump for a moment or two before letting it settle back in and proceeding on their way.
They are among us.
And I am among them.
I have my own theories why. But they are not important. What is important is this: I love it. I love it!
More Articles by Cheryl Ann (Cassie) Sanders
- And What I Wore (Ending)
- And What I Wore (Part 4)
- And What I Wore (Part 3)
- And What I Wore (Part 2)
- …and What I Wore

Cheryl Ann (Cassie) Sanders

Latest posts by Cheryl Ann (Cassie) Sanders (see all)
- And What I Wore (Ending) - August 26, 2022
- And What I Wore (Part 4) - June 5, 2022
- And What I Wore (Part 3) - April 2, 2022
- And What I Wore (Part 2) - February 10, 2022
- …and What I Wore - January 14, 2022
Cassie,
Thank you for such a wonderful article… So much sharing.
In theory and practice….as you said it best “I love it, I love it"
Leonara
Thank you for the nice note, Leonara, Amy, Tommie, Rose, et. al. I’m new to Heaven, but have a lot of stuff that I’ve published elsewhere over the years that I’ll start sharing. (I just got one turned down because it had a kiss in it. I guess too risqué for Heaven!)
Thank you Cassie, a very nicely written article. Oh yes, I’m all of those things!
Amy
Spot on, perfect insight, thank you.
Thank you so much Cassie, my feelings entirely. Being a woman is such a lovely and natural situation.
Loved reading words that reflect my thoughts…thank you.
It’s a lot of work to get dolled up and go out…but I am excited to plan our next meeting.
Every one stay safe and saine…
Later
Dr.T.J.
Though I’ve been as guilty of it as the next here, I think we all get tangled up sometimes in trying to figure out why when we would probably be better off just enjoying our journey through life – a journey which is ar more colurful and full of joy than many of our non CD/TG acquaintances.
Cyn
Hi Cassie, it’s Scarlett and this is my favorite article written to date in the well over two years I’ve been a member of CDH! They way you have painted such a lovely feminine picture with words, I could tell you were not a rookie writer for sure! I’m an editor in this department I wish I had had the opportunity to edit this lovely article! Whoever was lucky enough to scoop this one up as the editor probably didn’t have to change a word on this one! She might have had to add a tag or two and choose… Read more »
What a wonderful note, Scarlett! Thank you so much.
I’ve submitted a couple of other pieces, one of which has been approved and is in the queue. (The other is about my first kiss as a woman [by a man]. It was rejected as being, I guess, a little too risque for Heaven. I’ve edited down a bit and re-submitted it.)
I’ve got some stuff to do yet today, but will read your stuff tomorrow!
You’re so very welcome, Cassie! Yeah, you’ll get a big kick out of some of my articles. The seem to get a lot of attention!
Scarlett
Hi Cassie I enjoyed reading you article. I love reading about how many little things we have as thoughts your detail was just perfect. I have been dressing about the same amount of years and have attended first events in Provincetown I was a member of a club just outside Boston for many years back in late 80’s early 90’s. . Any way i enjoy your writing you have a very feminine way of presenting your self through your writing. Luv Stephanie
Thanks, Stephanie. My photo with the white top and pleated skirt was at a Provincetown First Event dinner party. Great fun. However, I remember having to get away from that scene and just be a woman at the mall. Drove halfway back down the cape to a mall just to walk around and use the fitting rooms to try on and buy some pretty clothes.