I have this very sweet genetic woman friend. She knows about Cassie. She is by nature a supportive and loving personality. And like all good friends among women, she is a superb listener. (Even if most of that “listening” is, in fact, back and forth emailing and instant messaging.)

She really hears when she listens; she listens with a sharp and sympathetic ear. Her responses always have a gentle, teasing wit layered on top of important things to say.

I had for a week, or probably two, bored her to death with endless recitations of sentences that began like these:

“Well, for Friday dinner, since it is a Friday and not a Saturday, and I should probably look as if I could even have gone to work in the outfit, so I think I’ll wear….” 

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“I don’t know, but if it is cold on Saturday morning, I guess I’ll wear….” 

“Well, you know those black Calvin jeans I have with the subtle gray pinstripe, well, for the museum on Saturday I thought I’d wear them with my boots and….” 

“To go to the club on Saturday night, I have this lacy two-piece top… it’s really kind of ‘juniors-looking’ for my age… but I just love it so much… and I think can get away with it in the clubby atmosphere.” 

Anyway, after listening patiently to this stuff, she burst out with something along these lines:

Good God, Cassie… calm down… you’re so excited you sound nuts… you’re so obsessed by what you’re going to wear and what you’re going to look like in this… or how you are going to look in that… Damn, girl, calm down.

But, I guess, you know, to be honest about it, I guess you do sound very much like just about every other girl I have ever known… that is… at least back when we were teenagers!

It’s true, Cassie, it’s astonishing how you really can be simultaneously two things, two people, at once. 

I mean, I know you are this successful middle-aged businessman… but God; I swear… these last few weeks talking about your upcoming date as Cassie… damn… your feelings… your attitudes… I swear they are totally indistinguishable from that of any woman, no, any girl, a girl about 20 or 30 years younger than you really are! 

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But, you know, now that I think about it, you know what I think… on reflection… I have to admit… I think it’s really sweet, so sweet. The way your mind, your emotions have been working so much as a woman’s mind and emotions this month. It’s absolutely making me cry as I type this, thinking of you like this, so excited… it is, it’s so sweet. I love you like a girlfriend! 

So, what did I learn about myself and my transgenderism from this outburst?

That despite my chronological age, my mind was working like that of an adolescent girl. My total times of close social contact with a man, as a woman, will have added up less than the average a genetic girl would have experienced very early in her adolescence: it is only reasonable that part of my personality would also be by nature, immature.

The thing that pleased me, about the total experience of waiting until my date, is the realization of what a blessing transgenderism really is. Others have often claimed that blessing… but I always read those claims skeptically, thinking of them as little defense mechanisms used to cope with such behavior. But… I really was having such fun this month! It can seriously be viewed as a blessing.

While living my straight life… busy at work… lots of meetings… lots of deadlines… an overworked businessman. And simultaneously, living… and not just in my imagination, but in reality… in real-life… as a woman. A woman incredibly excited in the adventure coming closer… REALLY getting into it, getting ready for it, choosing the clothes, buying new make-up, trying a new scent, this outfit that one, along with dieting and you know, washing and tending to my lacey, silky, girly stuff.


What a layer of adventure the getting ready itself was! How much richer, more complex, more interesting, more exciting, more fun it made my life that month before the date. How much richer was that month than it would have been if I were not transgendered, excited, scared, and enthralled. It occupied me with contingency plans, teasing my “fella” in email exchanges, sharing my excitement with my girlfriends… being a woman getting ready for her big weekend!

Being transgendered is a blessing. It simply enriches life one’s life incredibly. I was flying. And this was only the “getting ready” month.

At last, the day arrived!

I live in a New Jersey suburb of New York City. My fella lives in upstate New York and in Florida. But he is in New York City, often on business.

He would arrive from Florida by early evening, and he reserved two rooms for us. I checked into the hotel as a man… but my bags had only women’s clothes in them, only women’s clothes.

Am I the only crossdresser that has a routine that is positively ritualistic when I am about to change genders? I doubt it. There must be others of you out there with this quirk.

I do have my rituals, and I enjoy them, luxuriate in them, especially, as that Friday when I wasn’t rushed. I was in my room by 3:30. He wasn’t due to pick me up for dinner until 8:00.

I unpacked all my girl clothes. I totally emptied the bags. Skirts and dresses in the closet. Lingerie in the dresser drawers. Make-up and moisturizer on the bathroom vanity. This was now entirely a woman’s hotel room, Cassie’s room, no man, just Cassie.

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My ritual…

A bubble bath. Hot. Fragrant with bath oils. Long. Luxurious. Let HIM melt away in the steamy, scented, girly water. Let HER run her fingers along her forearms and feel the silkiness of the bath oil on her skin.

Then the long and enjoyable act of dressing and putting on my makeup while wearing a temporary garment. To be a girl, move with the grace of a girl even if all I am doing is laying out my clothes… and for all the early stages of the “becoming.”

Toenail polish always comes next… with cotton balls to keep my toes apart until it dries. Toenail polish always makes me smile. Wiggling my toes and stretching out my legs in womanly admiration.

Then the body shaping, cursing at the extra twelve pounds that were not there a year earlier. A little padding, a little cinching, the real, going-out-in all-in-one on top, a look in the mirror at the shape, at the curves of a woman in her underwear.

My nails aren’t long enough to manicure. They rarely are. Oh well, use the glue-on ones, the good ones with the strong glue so that they’ll last the entire weekend. Oh, I hate the built-in color of the glue-on nails. Polish over it to match my toenails.

Pantyhose. Sweater. Finish the makeup AFTER the mock turtleneck is in place. Play endlessly with my hair.

Heels. Go get the skirt.

Step into the skirt. Go look in the full-length mirror.

Okay, how does it look? It’s a Friday night, not a Saturday night. Dinner is only at eight. It should look casual… as if I could have gone to work in the outfit and then met my date for dinner.

I can’t be objective to the reflection. I see every flaw. But what will he see? What will the world see? I’m no kid anymore… you can’t hide that. (It’s easier to present, to change, genders than decades.)

Okay, I guess I look presentable.

I won’t know for sure until I see his eyes and in the way the rest of the world reacts to me.

But I’m ready. I’m ready to find out.

I watch the clock moving slowly toward the appointed time of 8:00.

I practice, for the thousandth time in my life, my walk in heels. I test my voice out loud. I return compulsively to the full-length mirror every few minutes for affirmation.

The room’s doorbell rings.

To be continued


More Articles by Cheryl Ann (Cassie) Sanders

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Cheryl Ann (Cassie) Sanders

Currently sliding from senior citizen into elderly. Dressing for almost 60 years, but rarely in last dozen. Fairly famous TG author, usually under one of two pen names (Alan Barrie or Cheryl Ann "Cassie" Sanders.) Many books in Lee Brewster's classic publishing line, Mardi Gras Press. And a long-time bestseller on Amazon, A WOMAN'S PASSION. (Those sales were eclipsed in recent years by all the $2.99 tg junk writing on Amazon; however, I recently got back the publishing rights and arranged for an inexpensive Kindle Edition and sales have picked right back up.) Also just added a new Kindle Edition of an old nugget to Amazon: THE SUNDAY GAME by Alan Barrie. Although always closeted to my family, I used to travel heavily for business, so had a lot of time to dress. Back in the day, could pass easily even in places like a White House tour or a hotel bar. Have been to a couple of the New England groups first events at Provincetown, but, again, not for a few years.

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Beverly Hanson
2 years ago

Oh my! How positively an accurate accounting of the “becoming" a mature woman. When, for whatever reason, life’s natural way of interfering with our intended growth ceases, we pickup where we left off: unfortunately immature. Dear, dear Cassie, it’s darn right stimulating the way you expressed your “growing up" and becoming more of the woman you’ve been destined and desired to be! And, being just an envious crossdresser, it was pure delight to read your preparations for Friday’s date night! Hell yeah I want to hear how it went!

Deborah Sullivan
Trusted Member
2 years ago

Oh my Cassie you described what I have so long experienced. Still have all the excitement of a young girl obsessed with what to wear especially when preparing for a date. Yes it is a blessing to be trangendered now

Active Member
2 years ago

Talk about a cliffhanger!

Kimberly Ann Victoria
Active Member
2 years ago

can’t wait until the next chapter

Purvi Purvi
Purvi Purvi
2 years ago


Raquel Smith
Raquel Smith
2 years ago

Cassie, what you said about your girl’s relative age totally makes sense to me. Although I’m 57, I’ve only really only been in touch with Raquel for for about 15 years. She had a very long childhood and now is entering adolescence and her young adulthood. It seems perfectly normal that my feelings as Raquel would be those of a much younger woman. But she is growing up and maturing quickly.

I look forward to reading the rest of Cassie’s story.

Much love,

Amy Myers
Noble Member
2 years ago

Thank you for sharing that wonderful experience with us, and your writing really made me feel almost like I was there with you! I consider myself pretty firmly hetro, but would love the feeling of getting all dolled up for a date with a special person, to go out in a beautiful dress and be pampered like I used to pamper my dates way back. You mentioned about this being a blessing, and I wrote up an article about the subject here sometime ago, as I so much agree with you. Often we feel burdened by these seemingly unsocialible desires,… Read more »

Kerry Johnstone
2 years ago

I can’t wait for the next chapter!

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