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

Edward smiled again and put his right arm around my shoulders, pulling me towards him while we walked. He raised his left hand to hail a cab.

Edward had mistaken the exact location of the jazz club. He did this comical little 360-degree turn when the cab dropped us off, looking around and saying, “I know it’s right around this intersection somewhere, but I’ll be damned if I can remember exactly. Do you mind waiting here a second while I go into this bar to ask the bartender?”

With the sidewalk crowded, I stood in the shadow of a closed newsstand to keep out of the flow of foot traffic. I stood in that exact spot as Cassie several years before, all alone, just wanting to be a woman in the world. I was all alone that night. How much better was this!

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Edward came out of the bar and grabbed my hand, pulling me across Seventh Avenue, calling, “It’s directly catty-corner from where we are and a few doors down … let’s make this light.”

Edward pulled on my hand, and we started running to get across the last part of the wide Avenue before the unsympathetic New York traffic bore down on us. Running in heels, across a busy New York City avenue, and trailing a step behind a man holding my hand was a wishful moment. All those years of practice paying off. Running in heels, running like a girl, now running as a woman, my right hand swinging with my gait. Running and smiling widely, then giggling until breathlessly laughing the last half-dozen steps.

And when we reached the safety of the far side of Seventh Avenue, Edward pulled me close to him, smiling widely as he bent and kissed me quickly. No one noticed. No one cared. He held the kiss just long enough for me to close my eyes as I sank sublimely into the feeling of being a woman in the world, a woman kissed by a man on a public street.

He walked us towards the club where a club guard opened the door for us. We entered the crowded club animated, smiling, and holding hands.

We secured wonderful seats at a table close to the band, and with great sightlines, but off to the side of the room, away from the jostling bar that ran the depth of the club

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We had come in near the end of a set, and the band went on break. We had been sharing a tiny table with another couple. Friendly, midwestern tourists, they introduced themselves to us during the break.

“Hi,” said the man, putting out his hand across the table to Edward, “I’m Bob. This is my wife, Karen. We’re just in from Ohio for a few days of fun in ‘the big city.’”

“Hi,” answered Edward, shaking Bob’s hand, “I’m Edward. This is my girlfriend, Cassie. We’re locals … although Cassie has never been to this particular club before.”

Again, I found Edward’s words reverberating in my head. This time, it was his spontaneously, sweetly exaggerated introduction, the words “my girlfriend, Cassie,” that sounded so strange, so delightful. Wow … this was so nice … to be introduced … and apparently accepted … that way … as his girlfriend … so simply … so matter-of-factly … I loved it!

After barely sharing a few dozen words with one another about the club, the city, and jazz, Karen surprised me when she jumped right into a very personal question. “So, have you two been together long? We’re married … God, is it? … yep … it’s over 26 years for us.”

“No,” Edward answered, without hesitating, and with calm candor, to Karen’s rather forward question. He continued, “this is kind of new for us, but … it’s…,” hesitating for just a second, “it’s nice … really nice.”

And with that, he kissed me on the cheek in front of them.

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I blushed a bit, but without even thinking about it, turned my face toward Karen, so only she could see, smiling, and kind of raising my eyebrows to share with her a pleased-with-what-he’d-said-and-done look. Karen immediately smiled back broadly and reached and covered my hand with hers firmly. She held my eyes with her own … and with her wide grin.

Her gesture clearly meant that she was pleased for me, seeing I was happy with what Ted had said.

But it was also something more. It was an expression that meant something else, something, somehow more complex and more serious than we were immediately sharing as two women, something that came directly out of the shared women’s understanding of the central importance of relationships in women’s lives.

It was amazing. A woman I had met barely a few minutes earlier, and here we were having an altogether feminine, uniquely woman-to-woman kind of connection. I had had my first natural “vagina dialogue:” a kind of connection that I recognized immediately to be unlike any I had ever experienced in my life before, a special kind of natural connection that exists among women and that differs from any kind of connection men ever experience. I knew immediately and without question, my interchange with Karen was one of the most unconsciously and purely feminine things I had ever done, one of the most feminine experiences and feelings I had ever had.

Then, closing my eyes in the wistful moment, I felt the first pangs of mourning that this magic was, of course, not real. It wasn’t my imagination at all, but a sweet reality that broke my reverie. As if he had been reading my mind, it was the actual, tangible, kind reality of Ted’s lips on my cheek again.

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And when I opened my eyes, his face was still so close to mine. Warm feelings flooded me, and I leaned forward just the tiny bit needed, and I kissed him softly on the lips.

Karen smiled at us again.

Karen and Bob and Ted and I got on famously the whole evening. We were enjoying one another so much that we all seemed to look forward to the breaks between jazz sets, breaks that were filled with chatter. I found it surprisingly easy to adjust my end of the conversation about work and family, minimizing the variations from the truth of my life stories, changing them just enough to stay consistent with my gender that night.

We left the club together.

Being ever gracious, Ted gave them the first cab that we found. While we waited to find another one, Ted put his arm around me, pulling me tight against him in protection from the gathering cold.

But luckily, we didn’t have to wait long for another cab; and we were soon headed back to our hotel.

The cab was warm and comfortable. I slid in only halfway across the wide back seat; and when Ted got in after me and closed the door, I hesitated only a moment before tucking in under his arm, pulling it around my shoulders, letting my head drop onto his shoulder, and shamelessly snuggling in against him.

And that was the ride back to our hotel.

(And I was already thinking about the outfit with the red jacket that I would wear to the museum tomorrow.)


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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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Cassie Jayson
Trusted Member
2 years ago


Raymond Swarmer
2 years ago

That sounds like quite the evening! I too love a great jazz club. They are always very intimate and friendly and I’m so happy for you being able to be who you are. Can’t wait for the next chapter in your wonderful, romantic adventure. Stay gorgeous!

Amy Myers
Noble Member
2 years ago

What a fabulous night! I’m so thrilled you choose to share it with us as well. You article managed to capture at least a bit of the magic you must have felt with your date that night.

Deborah Sullivan
Trusted Member
2 years ago

Ted sounds like a real winner and the kind of guy many of us admire and desire. Thanks for sharing Cassie

Donna Cooper
Donna Cooper
2 years ago

Cassie, thank you for sharing the experience in a way that gave such a lovely sense of how you felt in “simply" being a woman on a date with her man.

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