Ted didn’t seem to mind me snuggling against him. Instead, he smiled down at me, pulled me in even tighter against himself, and kissed me on the forehead. I let my eyes close, feeling in that posture overwhelmingly warm, safe, cared for … and female, so very female.

What I actually wanted … was to be kissed.

I wanted to be held. I wanted Ted to want to kiss me.

As a crossdresser, my breasts are not my own. But they are expensive and soft and proportional to my body. They take on and maintain my body’s own heat, and when wearing a properly fitting bra, they move naturally with me. After years of wearing them, they just feel like they are my own to me when I’m dressed.

En Femme Style

Sex is doubtlessly just as much a phenomenon of the mind and imagination (and heart) as it is of the physical body. So, to get back to the narrative, I wanted to make out in that cab; I wanted it badly.

But Ted wanted to keep talking, so I tried to keep up my end of the conversation, tried to hide my disappointment.

In one short evening, I had become so greedy! I should have been sooooo satisfied with just that simple conversation. I should have been ecstatic about it. Instead, I just took it so matter-of-factly, as we rode in that cab, talking totally and comfortably as a couple, as a man and a woman together, as we talked about our evening and about our plans for the next day as a couple together again. How spoiled I had become so fast, not to treasure, but just to be a woman, to be the woman I was that night, that weekend.

I should have been treasuring it, that gift of being able to have an unremarkable conversation totally as a woman with a man; but what I was doing instead was just taking it for granted. I was hungering for more.

No! No, it’s not just lusting that I’m talking about. It’s not just about sex. Okay, it is about sex … but it is also about connection. It is about the idea of a, at least theoretical, romantic possibility … the possibility of a profound connection between two people.

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At some level, all of us, from those transgendered, the most hurried, most “sometimes,” most closeted secret crossdresser to the most successfully deep-stealth post-op transsexual, all want to be seen as women, even to be desired; we all want to be seen and valued in exactly the same way as all women want to be seen and valued. And that’s why being a crossdresser, being transgendered at any level, of any class, is not just fetishism, why it is not just about the clothes we wear. It’s about who we are when we are dressed.

But Ted didn’t kiss me in the cab.

But he continued to hold me close to him the entire way back to the hotel.

Our boutique all-suites hotel was small enough, and it was so late at night, that the glass doors from the street were locked. We didn’t have to ring the bell; the front desk attended 24 hours per day and was visible from there. We could see the desk attendant coming around to open up for us even as we crossed the sidewalk from the cab.

We exchanged a bit of pleasantry with the attendant.

Then Ted took my hand as we walked across the empty lobby, and I couldn’t help but think about the attendant watching this middle-aged man and woman strolling slowly, hand-in-hand, the sides of our shoulders just barely touching, strolling to the elevator late at night in a midtown Manhattan hotel. For some unknown reason, the image almost made me cry.

Crossdresser Superstore

Our (separate) rooms were on the third floor. But Ted’s arms were around me and his lips were on mine even as the elevator doors were still closing behind us.

The elevator doors opened on our floor … and closed again. And still, we held the kiss and the embrace.

With us still in it, the elevator started a slow ascent to the top of the small, quiet, late-night hotel; and in that slow-moving elevator, I wrapped my arms around Ted’s neck, pressing against him.

The elevator doors opened and stayed open on the empty, quiet hall of the top, the ninth floor; my head was spinning. My knees were like rubber. I found the strength to break and lean back away from the kiss and whisper, “I think … I think we should go back downstairs.”

Ted kissed me quickly again, stepped away a bit, and pushed the third-floor button.

The elevator doors closed. Ted took me back into his arms. And the elevator moved slowly down to our floor.


The rest of the weekend went as swimmingly as that first date. But I realized as I wrote that last sentence of the description of our first night together, detailing more about the rest of the weekend would not add much to fulfilling the goals of this memoir.

So, I’ll let the detailed description end there.

But, in summary, this is what we did the rest of that weekend. On Saturday morning, a friend came to my suite and (as I rushed in and out of the outfits) took all the photos I’ve shared here. The skirt, sweater, and jacket outfit I wore Friday night. The jeans and sweater and red jacket outfit I wore during our time in the museum on Saturday afternoon. The “juniors-looking” pale lavender top with tight gray pants and boots outfit I wore to dinner and to a fun night at two clubs on Saturday evening. Ted and I continued to see each other a couple of times per year for several years, but then both of us drifted away from the t-girls’ party scene in New York. We lost track of each other and haven’t communicated in many years.

En Femme Style


More Articles by Cheryl Ann (Cassie) Sanders

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Rozalyn Richards
Trusted Member
1 year ago

Hi Cassie it must have been wonderful being treated like a lady for the whole weekend, but what a sad ending to a wonderful story not meeting up again with the man of your dreams, I think most of us would love to be treated like a lady at least once in our lives X
Hugs Rozalyn X

Rozalyn Richards
Trusted Member
1 year ago

Hi Cassie I’m sorry for not getting back to you sooner, I tried sending you an email to your email address but it wasn’t recognised, if you want to email me then i can email you back, my email address is royleah59@gmail.com , I would love to hear from you, hugs Rozalyn X

Deborah Sullivan
Trusted Member
1 year ago

Yes Cassie it sounds like a wonderful evening a girl can’t forget. I have been there too and simply nothing like it Being held kissed and treated like a lady for the whole evening and the excitement in showing it off in public. I have such memories and know they last a lifetime

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Stephenie Derick
1 year ago

Cassie, I loved the longer version of your story. I encourage all the readers of you to request the longer version. It is so much better.


Sherri Remington
Trusted Member
1 year ago

Hi Cassie, what a thrill it must have been , to have all those feelings continue through out the weekend and then to continue the relationship for years later. I’m not sure that I want to share such a weekend with a man but would love to with my wife, since we both have a strong friendship already. But what your weekend adventure brought more to my attention was all those small things to do to make us feel more feminine, from the sitting, walking, of course the looks, to carrying your hand bag. Of course I’ve thought of all… Read more »

Danielle Anaya
1 year ago

Such a wonderful story. I remember the feeling of finding that kind, gentle, warm man who totally accepted me as the woman I had always wanted to be. The culmination of that first experience led to a series of events that allowed me to be as much of a woman as I had ever dreamed of. I am still with him, and have been his girl ever since. So much has happened from the first time I ever wore women’s clothes to now being in a magical relationship. I hope you are still sharing those moments with a special man,… Read more »

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