A Memoir of a Weekend Spent as a Woman Tourist in New York City … with a Man (PART 1)

Okay, it’s true. I stole the title for this essay from a portion of the title of a delightful and bestselling memoir published several years ago (Love, Loss, and What I Wore by Ilene Beckerman).

Ms. Beckerman’s memoir reminds us of what seems to be a remarkable truth about women. If you name a dramatically important event in her life (her first dance recital; her first day of junior high; her first real date; her first kiss; the day she told her husband that she was first pregnant.) If you name the day, almost without fail, she can tell you what she was wearing.

For women, their clothes, the image they have of themselves in their memories (or to borrow from what we tend to say, the way they “presented” themselves to the world on that particular day) is so vitally important that their clothes are intrinsically connected to those important moments.

Join Our Community-cdh

Many years from now, if you were to ask me about my weekend spent as a woman with a man, I would be able to tell you exactly what I was wearing at every important moment.

The weekend was that important to me.

I am writing this essay so that I may capture this weekend on paper for myself, what I did, what WE did, and what it meant and means to me. And I invite you, if you are so inclined, to share these journal entries, these bits of fact, of introspection, of rumination.

First, you should know this essay isn’t about any reference to my sexuality or in providing detail on the nature of my relationship with my weekend’s fella.’ This essay has more to do with the, although common for many readers of this venue, rare for me, simple, touristy experiences at spending a very sweet weekend in New York City … as a woman … with a man.

It’s not that sexuality isn’t important. Of course, it is. Readers of this venue have come to understand that gender identity and presentation are very different things than sexual preference and activity. All the mix-and-match possibilities exist among us. I choose not to share with you at which point I fall on this vast plane.

Instead, I pen this memoir as an exploration of what would be considered, although fun, quite likely a mundane happening for a woman. Nothing so special were it not for the fact that I am not a genetic woman, and I live most of my life as a man.

Join Our Community-cdh

But not this weekend! Not this weekend!

It may still be of importance to note that I define myself as a crossdresser that considers one’s self an “occasional” woman.

I want to get one last classification thing out of the way before proceeding. It is, I think, less important to the narrative than many of you would guess. Actually, it was less important than I would have guessed before having had the fun we did have this weekend. I should let you begin your reading with your own stereotypes about generations. As I am afraid will be all too obvious as you look at the photos that accompany these essays. Let’s just say that neither my fella’ nor I know terribly much about hip-hop. We are, each of us, on the downslope of middle age, not quite yet getting to that senior-discounts-at-the-movies point, but getting closer to that than to Jack Benny’s perpetual age of 39.

But, as I said, I don’t think our ages had much impact on the experience of this weekend. The dinners would have tasted the same. The music in the jazz club would have sounded as cool (not kewl). Okay, he tended to wear sports jackets when we went out and my skirts were above my knee, but not micro-minis … I think you get the picture … but otherwise I truly don’t think our time together would have been so different plus or minus a generation.

Now to get on with it.

My first date with a man as a woman in nearly a decade: who was this guy?

Crossdresser Superstore

Well, first of all, calm down you all, of course, he “knew.”

I knew he knew if for no other reason than because I met him originally almost a year earlier at a club frequented by the transgendered (of many classes!) and usually by an even larger number of what are variously called “admirers” or, more pejoratively, “chasers.”

For those of you who have never experienced this scene, it is not so different from any singles bar in the country, a place in which individuals are socializing generally while simultaneously trying to find a way to connect with one another particularly. There are those men who, at their core, are as desperate as anyone to crack the existential loneliness of life … and meet somebody with whom to connect … and, for whatever reason, the somebodies they seem to like are us!)

Well, anyway, I met this fella’ when he bought me a drink at one of those clubs … and we wound up talking for hours.

He asked me out almost immediately, and I instinctively liked him. But sitting in a club and having drinks with a guy is a very different thing than getting dressed up in a pretty skirt, top, and make-up and waiting for the doorbell to ring for a date out alone with him, so I demurred. I demurred for almost a year as we emailed back and forth.

And finally, I said yes.

Having not had an out-in-the-real-world date as a woman with a man in a looooong time, I can’t tell you how excited I was! Actually, the long delay time of nearly a month between setting the date and having the date was great, making for a fun month of expectation.

During that month… even after all these years… I learned some new things about myself… and about my transgenderism… nice things… things I found and find comforting… even wonderful.


More to come…




More Articles by Cheryl Ann (Cassie) Sanders

View all articles by Cheryl Ann (Cassie) Sanders
The following two tabs change content below.

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.

Latest posts by Cheryl Ann (Cassie) Sanders (see all)

5 2 votes
Article Rating
Inline Feedbacks
View all comments
Trusted Member
2 years ago

Wonderful post Cheryl Ann. Cute outfit, very classy. It was great that you shared how much thought and mental effort if can take to go one step at a time, but you did it!!

Deborah Sullivan
Trusted Member
2 years ago

I can totally relate to this Cheryl and good for you. Your outfit is also appropriate for a weekend in NY. I have spent time with my b/f in the city who is a true admirer of tgs and cds

Ger Hayden
2 years ago

I cant wait to read episode 2. Fascinating and exciting.

Dani Grand
Active Member
2 years ago

You look wonderful

Would love your thoughts, please comment.x
Subscribe To Our Newsletter

Subscribe To Our Newsletter

Join our mailing list to receive the latest news and updates from Crossdresser Heaven.

You have Successfully Subscribed!

Log in with your credentials

Forgot your details?