Remembering a Weekend I Spent in New York City As a Woman… with a Man

Then… the room’s doorbell rang.

My heart fluttered.

EnFemme Style

But I didn’t hesitate. I walked to answer the bell.

I stepped back and he stepped in, letting the door close behind him.

Right there by the door, he did and said… just about the perfect things. He took my hands in his and spread his arms, standing back a bit, making a circle of our arms, and looked at me… looked at me!

“You look great,” he said. “First, do come down the hall. I thought we’d have drinks in my suite before we go to dinner.”

Our rooms were in an all-suite hotel: bedroom, small living room, galley kitchen.

“Okay,” I said, “I’ll bring my jacket and we won’t have to come back here.”

“Great,” he said.

I felt his eyes on my back, my skirt hem shifting at my knee, as I walked away from him to where my jacket and bag lay on a chair. He put his hand on the small of my back, guiding me to his door.

A small plate of cheese and grapes was on the coffee table, as were an open bottle of wine and two glasses. A half-dozen large shrimp on another plate surrounded a saucer of cocktail sauce.

I sat on the couch, first crossed my legs, then uncrossed them, keeping my knees together, as he came over towards me. But soon after we started our wine, Edward looked at his watch and said, “We should get going to make our reservations at the restaurant.”

I swallowed down my nerves, thinking to myself, “Here we go. I guess I look okay. At least he doesn’t seem the least bit concerned about being seen with me!

Visit Transgender Heaven

We walked out into the hotel hallway toward the elevators. He jabbered away, totally casual. I was nervous. As we approached the elevators, I saw the worse thing imaginable—teenage girls. Three of them waiting for the elevator. They were talking and giggling with one another. Teenage girls in a group are the hardest audience. They see everything. And they have no graciousness.

This worse potential audience, waiting to get on the elevator with Edward and me. I couldn’t help but focus intently on them as their eyes flicked over us as we approached. Edward talked on without a care.

Nothing. The girls gave us just a second of attention and went on with their business. They let us pass and enter the elevator first, standing in front of us facing forward, talking away, never once looking back at us, at me.

I loved it. Only a nervous tg-woman can know how good it can feel to be invisible, to be so unremarkably normal as to be barely noticed, to be a middle-aged woman, on the arm of a middle-aged man, on her way out to dinner with him.

After that, the crowded lobby and the doorman holding the door open for us were easy.

I walked easily in the comfortable heels I’d worn many times before. My shoulders and back were straight, remembering that old tg trick: walk like you’re proud of your breasts; it will help keep your posture right. Walk from your hips, not your shoulders. I held the strap of my bag in my left fingertips. My right hand swung forward with my left foot. I was a woman in a skirt and heels walking down a New York City street with a man. It was so unremarkable. It was so REMARKABLE!

Crossdresser Superstore

Edward held open the door of the taxicab. I slid in, butt first, smoothing my skirt under me, keeping my knees together as I swung my legs in. I slid over to make room for Edward. We were so close! My skirt had ridden up a bit from the angle of the seat. Edward gave the taxicab driver the address. Without a word, he leaned back, turned toward me, and smiled. He settled back into his seat and, so naturally, rested his left hand gently on my right knee as he said, “This is nice. We’re going to have a good time.”

That’s how we rode to the restaurant.

The cab stopped at a safe place several doors past the restaurant in which Edward had made reservations. Edward took my hand to help me out of the cab. But he didn’t let go, holding my hand as we walked to the restaurant. He had kept my hand in his, and, by that simple act, he announced to the surrounding world he was happy, proud to be with this woman standing next to him. I felt quite wonderful… valued… and… validated. His simple and casual act made me feel more comfortable, more whole, more a woman than anything else had in years.

As it nourished that lifelong craving for that feeling of just being the female me, just being a woman in the world, the feelings became so intense, so important that for the first time that weekend, but for what would not be the last time, it was a matter of sheer willpower that prevented my emotions from driving tears from my eyes.

En Femme Style

With Edward close behind me, I followed the maître d’ to our table through the crowded dining room. I walked so pleased with myself that I was having trouble keeping my smile contained to something reasonable.

As the maître d’ held my chair, I smoothed my skirt and pictured what the other diners were seeing, what Edward was seeing as he sat across from me smiling.

We ordered a bottle of wine, settling on the salmon for our entrée. Our conversation kept us engrossed during dinner that I “settled” into being a woman so profoundly, so completely. It would have been more startling not to have, not to sense being inside my woman’s body.

And the evening was still young. And it was only the first evening of our planned weekend together.

By the time we made our way out of the restaurant onto a sidewalk crowded with people making their way to the big cineplex next door, I realized again at how incredibly comfortable I felt, how much I had settled into my role as a woman out with a man on a Friday night.

Edward suggested we walk down the block to get away from the movie crowd before trying to hail a taxi. I slipped my left hand through Edward’s arm, resting my fingers over his bicep, our gait together naturally comfortable.

Edward looked down at me and smiled. I asked, “This is so nice walking with you like this. And I’m flushed after that warm restaurant and the wine. Can we walk for a block or so before we jump in a cab?”

Visit Transgender Heaven

“Of course,” he replied. “It’s still early… and the jazz clubs stay open very late. We have all night.”

We walked. I clung to Edward’s arm. My heels clicked on the sidewalk and my skirt swayed back and forth at my knees… And I was in seventh heaven.

And the evening was still young.

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)

Tags:
5 2 votes
Article Rating
Subscribe
Notify of
9 Comments
Inline Feedbacks
View all comments
Trish White
Baroness
Active Member
1 month ago

Hi Cheryl, What a wonderful story, you must have been in 7th heaven to say the least. There is nothing like being with a man to have your femininity confirmed. I’ve been married for 47 years but back in my 20’s I had an evening with a man when I was in Vancouver on business. It was totally unplanned. After shopping enfem I went to a gay bar to just have a drink and relax a bit but long story short I ended up with a very nice very cute guy in my hotel room and we made love. It… Read more »

Leonara
Ambassador
Active Member
1 month ago

Thank you Cheryl for sharing “how much you had settled into your role as a woman out with a man on a Friday night”. Such an inspirational experience for the ladies here at CDH and for me… your pointers and subtle reminders of the nuances of being out & about expressing ourselves as the woman within are most welcome… thank you again for an article sharing a personal experience with all of us… Regards Leonara

Lucinda Hawkns
Active Member
1 month ago

thank you for sharing your post , what a date that was. you must of had a great night and walking around and no one says a thing.

Auroras Livingfem
Member
1 month ago

Hi Cheryl wow what a beautiful story it remind me about before retiring I used all dressed a night drive once in awhile and I invited another sister that somehow knew I CD she didn’t drove so ask me to go with her to a party where some sisters had their man that was my first time going to all dressed and my friend looked the souls of the party and me too I was wearing a black sparkle knee dress nylons garter belt normal kind of shyness but secure in all I was wearing well we just had stopped… Read more »

Kerry Johnstone
1 month ago

Please tell us there is a part 4?

Chrissy Simpson
Duchess
Member
1 month ago

Great story of your success and conquering the evening! 

Vanessa Jones
Active Member
1 month ago

Wow Cheryl!

I hadn’t seen part 1 or 2 when I read this article. However, I was on the edge of my seat. I must go back and read 1 and 2. Hope there is a part 4!
I feel as though you crossed over to what ~ perhaps a lot of us may have thought about, dreamt of, or wished we could have the courage to do.
Thank you so much for sharing

Hugs,

Vanessa 

9
0
Would love your thoughts, please comment.x
()
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

or    

Forgot your details?

Create Account

If you don't see the captcha above please disable ad and tracking blockers and reload the page.