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Retro Rerun — What I Wore by Cassie Sanders

| Aug 11, 2008
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Several people have complained that Cassie’s serial from several years ago, What I Wore: A Tale of a Weekend as a Woman with a Man, is not all there. Meaning it’s got chapters missing, not that it’s odd or “not quite right”. Moving things from the old ’90s TGF into another format caused several things to not show up they way they should due to changes in html code or the story just didn’t get into the new database. We’re working on all that stuff and this fall a new format that will knock your knickers off will be making its debut. In the meantime disgruntled readers who wanted all of their What I Wore contacted Miss Sanders directly and she was kind enough to send us the entire, all in one lump, What I Wore that details her weekend spent  as a woman with a man. Thank you Cassie. And now…

…and What I Wore: A Tale of a Weekend as a Woman with a Man

By Cheryl Ann “Cassie” Sanders

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

Those among you who are literary minded will remember that Proust believed that tastes and smells are the strongest triggers of memory. In one of the most memorable scenes in literature, his most important character, Swann, eats a type of cookie called a Madeleine, dipped in sweet tea, and is immediately flooded with a particular memory from his childhood.

Similarly, 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 in high socks and a short skirt; her first real date; her first kiss; the first time she let a boy’s tentative fingers investigate her body; her prom; the day she told her family she was engaged to be married; her father’s funeral; the day she told her husband that she was pregnant with her first child), name that day, and, almost without fail, she can tell you what she was wearing on that day.

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

In just that vein, if, many years from now, you were to ask me about my recent weekend spent as a woman with a man, I think I would be able to tell exactly what I was wearing at every moment of it.

The weekend was that important to me.

I intend to pepper these essays with photographs of what I wore … but, in the interest of disclosure, you should know that, although they are all true to the actual clothes of each moment described in the essays, the photos were in fact taken, not at the pertinent moment, but all at once, by a friend on the Saturday morning of that weekend. (They are almost exact, but not exactly exact. For example, when I actually went out on Saturday night, I had my pants tightly tucked into my boots; but for the shots taken on Saturday morning, I was rushing in and out of the clothes, so, for example, the pants in the shot you’ll see here are unattractively bunching at the top of the boots … but they looked better on Saturday night … honestly!)

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 (before some of you get your hopes up!), I intend to edit out of this essay any reference to my sexuality or too much detail on the nature of my relationship with my weekend’s fella’ that has anything to do with intimacy. This essay has more to do with the, although common for many readers of this venue, rare for me, simple, touristy experiences of 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. It’s just that it isn’t the focus of this essay. Readers of this venue have long ago come to understand that gender identy and presentation is a very different thing than sexual preference and activity. All the mix-and-match possibilities exist among us. There are transsexuals, transgenderists, and crossdressers who prefer men as sexual partners and those that prefer women. There are some who prefer liaisons with one sex when presenting as one gender and a different sex when presenting as another. There are even those who choose one sex for masturbatory fantasy and another for actual activity.

I choose not to share with you at which point I fall on this vast plane.

Instead, this essay deals more with what would be considered, even though fun, quite mundane happenings for a woman, nothing so special were it not for the fact that I am not, in fact, a genetic woman; and that I live most of my life as a man.

But not this weekend! Not this weekend!

I guess it is important that I do define for you my “class” in our class-obsessed tg-world. I am, in most general terms, a crossdresser. Within that general class, I fall within the group that considers ourselves “occasional” women.

Before getting on with my narrative, I have to abstract from some of my earlier columns in these pages a couple of remarks on my, and many of my sisters’, beliefs about ourselves. For one thing, we totally reject those last vestiges of class warfare that plague our community. We will not accept disdain from some unreconstructed transsexuals who seem incabable of stopping considering us some lower order of being than themselves. We, defensively but resolutely, instead claim pride in our own free will, in our own right, our own ability, and our own pleasure in being women … occasionally. Secondly, you should recognize that most of us are long-past the point in our lives when dressing was primarily an auto-erotic exercise. The pleasure of our lives now is in occasionally being a woman, in presenting as such, in living as such, as absolutely and completely of which we are capable, often with equal or even better grace and authority than many transsexuals, but for periods of time, from minutes to days to weeks to months to years, simply put, that are exactly as long as we choose.

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. But, I should let you begin your reading with, at least at first, bringing with you your own stereotypes about generations. As I am afraid will be all too obvious as you look at the photos that accompany these essays, well, 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?

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 freguented by the transgendered (of many classes!) and usually by an even larger number of what are variously called “admirers” or, more pejoratively, “chasers.”

I don’t want to interrupt this essay (with another one also sitting incomplete somewhere in my computer) on this “scene” of tg-party clubs. Suffice to say here, for those of you who have never experienced this scene, that it is extremely varied … but that the bottom line is that it is not so different from any singles bar in the country, a place in which individuals are socializing generally and simultaneously trying to find a way to connect with one another particularly. (You can view it negatively: a bunch of pigs hitting on a crowd of particularly vulnerable girls. Or you can look at it positively: a bunch of men who, at their core, are as desperate as anyone to crack the existential lonliness 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 had 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 while we emailed back and forth.

And finally, I said yes.

Part 2

Cassie with jacket and purse.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.

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

I don’t mean that she’s a great listener just because she is a patient listener … although she is that. I mean that she is a great listener because she really hears when she listens; she listens with a smart, sharp, and sympathetic ear. And 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….”

“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 think I can get away with it in that clubby atmosphere.”

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

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 sounded at one time or another … 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, actually, any girl … except maybe a little more ‘hysterical’ … oh and, as I said, a girl about 20 or 30 years younger than you really are!

You know, it’s amazing. It’s truly amazing. It’s … it’s more …this being a girl so excited about an important upcoming date … it’s more … more … more profound … a more real female thing …more then I’ve every seen with you before … you know … it’s much more … ah … bigger, more important … than just seeing you put on a dress and some make-up and going out as a woman.

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 so cute. It’s so feminine. It’s darling. It’s absolutely darling. 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 this …I do love you like this, girl … girlfriend!

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

Well, the fact that despite my chronological age, my mind was working like the mind of an adolescent girl wasn’t so surprising. I mean, even after this expected weekend, my total times of close social contact with a man, as a woman, will have added up to less than the average genetic girl would have experienced with boys by very early in her adolesence: so it is only reasonable that that part of my personality in this context would be so immature.

No, the thing that pleased me about that outburst, about the whole experience of waiting for the time to go by until my date, is the realization of what a blessing transgenderism really is.

Other people in these pages have often claimed that blessing … but I always read those claims skeptically, thinking them as little defense mechanisms used to cope with behavior that was beyond will.

But I really was having such fun this month! It is true. It really was such fun. It really can be viewed as a blessing.

I was living my straight life … a busy time at work … lots of meetings … lots of deadlines … a normal, busy, successful, overworked businessman.

And simultaneously, I was living … and not just in my imagination, but in fact … in real life … as a woman, a woman incredibly excited by the adventure coming closer and closer … REALLY getting into it … REALLY getting ready for it … REALLY choosing the clothes … REALLY buying new make-up … REALLY trying a new scent … REALLY trying on this outfit … trying on that … trying on this … trying on that … dieting … REALLY washing out <blush>, you know, my lacey, silky, girly stuff.

I REALLY was doing all this stuff. I REALLY was getting ready. 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 for that month before the date than it would have been otherwise. How much richer was that month than it would have been if I were not transgendered, excited, scared, enthralled, occupied with contingency plans, teasing my fella’ in our emails about what fun we were going to have, sharing my excitement with my girlfriends … being a girl … being a woman getting ready for a big weekend with a man!

Why, how can the non-transgendered get through their days on only one simple level? Why they must get bored to death with themselves!

Being transgendered is a blessing. It, simply, enriches life incredibly.

I was flying. And this was only the “getting ready” month.

Part 3

Cassie CollageAt 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 had reserved two rooms in a hotel on the east side of New York at his corporate rate. I was taking that Friday afternoon off. He would be arriving from Florida by early evening. He had made reservation at the hotel for me (in the name on my driver’s liscense).

I checked into the hotel as a man … but my bags had only women’s clothes in them, only, only women’s clothes.

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

In any case, I do have my rituals. And I’ve come to enjoy them, luxuriate in them. Especially, as on 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.

The first step is putting away the male stuff. Lock it in a bag. Put the bag on the top shelf of the closet. Put another empty bag on top of it. Begone you! Cassie is about to be reborn yet again.

I unpacked all my girl’s 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. For me … for the chambermaid … for the Gods looking down … this was now entirely a woman’s hotel room … Cassie’s hotel room … my hotel room. No man was staying there. Just Cassie.

Now … back to the ritual.

A bubble bath. Hot. Fragrant with bath oils. Long. Luxurious. Let HIM be melted away by 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, slow ritual of dressing and putting on make-up.

First a light all-in-one (with breasts in place) … but still a temporary garment … just to wear to be sure, even at this early stage of getting ready, that the boy is gone, gone away somewhere … just to be a girl … move with the grace of a girl … be a girl … even as all I am doing is laying out my clothes … and for all the early stages of the “becoming.”

Then, toenail polish always comes first. Toenail polish, with cotton balls keeping my toes apart until it dries. Toenail polish always makes me smile. Finished toenail polish always makes me wiggle my toes. Toenail polish makes me stretch my legs in front of me with my wiggling toes at the end … a girl … a woman … wiggling her girl’s toes.

Then the bodyshaping, cursing at the extra twelve pounds that were not there a year ago. 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-ons, the good ones with the strong glue so that they’ll last the whole weekend. Oh, I hate the built-in color of the glue-on nails. Polish over it to match my toenails. Let it dry. Another coat.

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.

How do I look? How do I look? I don’t know. I can’t be objective. 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 guess I look okay.

But I won’t know for sure until I see his eyes. I won’t know for positive until I see how the world reacts to me.

But I’m ready. I’m ready to find out.

Part 4

The dinner look.I watched the clock moving slowly toward the appointed time of 8:00.

I practiced, for the thousandth time in my life, my walk in heels. I tested my voice out loud. I returned compulsively to the full-length mirror every few minutes.

Then…the room’s doorbell rang.

My heart fluttered.

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. “You look really great … but, you know, I’m not sure I would have recognized you if I didn’t know it was you that was supposed to be in here.”

“What’s … what’s that mean?” I asked.

“You … you still look like you from the club, of course … but now … tonight … God, you look so … I don’t know … normal, so everyday.

“Remember, we’ve only known each other at the club … I remember you from the club … in those, I don’t know the right word, flashier(?) kinds of clothes you wear at the club. But this … you know, I like this even better … much better.”

“Well,” I understood, “I was, I guess … I was, of course, wearing club clothes that night we talked for hours it seems.

“But … you know … I didn’t think that look was appropriate to go out to dinner with … you know …” and I continued, realizing even as I was doing it, without even thinking about it or trying to do it, just doing it automatically, doing it with a girl’s automatic, instinctive little flirt to my voice and eyes, “you know … to go out to dinner to a nice restaurant with a nice looking guy.”

He smiled broadly at that: “Yeah, right … I’m just this gorgeous guy, aren’t I … well, no, thank you anyway. Hey, really though, really, do you like this sports jacket? It’s brand new. It’s the first time I’m wearing it.”

“It’s beautiful. It’s cashmere, right. I can tell. Very cool.”

“Yep … and really … YOU do look really nice … just perfect for my plans for this evening. But first, 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.

The door to the bathroom was mirrored and as I passed it I looked at myself quickly … my mind filled with his compliments … and suddenly, I was filled with confidence. My jacket over my arm. My bag on my shoulder. I looked great.

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 dinette table. An open bottle of wine and two glasses. A half-dozen large shrimp on another plate surrounded a saucer of cocktail sauce.

I was blown away by the thought of him preparing for our date … while I was a hundred feet down the hall … doing the same thing.

I sat on the couch, first crossed my legs, then uncrossed them, keeping my knees together, as he came over toward me.

He moved the refreshments from the dinette table, to the coffee table in front of the couch. Poured us wine.

“You look nervous,” he said.

I was taken aback. I hadn’t realized I looked nervous to him.

“No,” I said, “not nervous … excited. I … I haven’t been out to dinner with a man in a long time.”

“Well, whatever … don’t … really … don’t be nervous. You look great. We’re going to have a great time. I made reservations at East of Eighth because, after you shared with me in your last email that you hadn’t been out to dinner with a man in a long time, I thought you’d be more comfortable there … at least for tonight.”

East of Eighth used to be a mostly gay restaurant and bar. But a half dozen years ago, they built a giant cineplex right next store … so now it gets a very mixed crowd. There are all kinds of people in the big, crowded bar and restuarant all the time. Somehow, it’s also become a favorite for the more “passable” tg-girls to meet one another and have a drink, and sometimes something to eat, on Saturday evenings, before heading out to the clubs.

But, this was Friday night, not the usual Saturday night when there could be as many as fifteen t-girls there. I doubted that there would be any other t-girls there on a Friday.

Let’s call my date “Edward.” Anyway, Edward was familiar enough with the tg-scene in New York City that he knew that, being familiar with the place, I’d be a least a bit more comfortable there … especially since we had talked about the food being good there during that first time together at the club.

We sipped our wine and tasted the hors d’ourves.

A wine glass in my manicured fingers. A wine glass with the soft impression of my lipstick on its rim.

Talking … talking so easily with Edward about his trip up … about the great value of the suites in this hotel.

From out of nowhere, he interrupted our casual conversation, teasing, a bit suggestively, “Cassie, you really do look scrumptious.”

I felt myself blushing, for real, leaned back, crossed my legs, searching for the right words to say “whoa,” but couldn’t quite find them. There was a moment of silence.

But then, he qualified his flirt with the simple, reassuring statement, “Hey, Cassie, dinner and some jazz … dinner and some jazz … that’s all.”

I smiled at him … and the bit of tension was broken.

A nibble on a shrimp. A bit of cheese. A sip of wine. A grape.

Talking about his son … and my daughter. Talking about where he grew up. Talking about the weather and

… about our plans for the evening … and for tomorrow.

Part 5

Edward looked at his watch and said, “We should get going to make our reservations at the restaurant.”

Jazzing it up.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!”

He helped me on with my jacket and I put my bag on my shoulder.

We walked out into the hotel hallway toward the elevators. He was jabbering away, totally casual. I was nervous as hell.

As we approached the elevators, I saw the worse thing I could. Teenage girls. Three of them waiting for the elevator. The hadn’t noticed us coming down the hallway yet. They were talking and giggling with one another.

I always dread running into teenage girls in a group when I am out in public as Cassie. Teenage girls in a group are the hardest audience. They see everything. And they have no graciousness. The only thing important to teenage girls is their status place within their own groups. They won’t hesistate to giggle and make rude comments out loud if they think it will score some kind of points for themselves among their friends. No matter how hurtful they are being to others.

The worse possible audience was waiting as we approached, 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 jabbered on without a care.

Nothing. They gave us just a second of attention and went on with their talking and giggling. They let us pass and enter the elevator first, entered, stood in front of us in the elevator 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 was easy.

“Let’s walk out to Lexington Avenue,” said Edward. “Getting a cab out there will be a lot easier.”

I walked easily in the comfortable heels that I had worn many times before. I kept my shoulders back, my back straight. I remembered 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!

Edward held open the door of the taxicab. I slid in, butt first, smoothng my skirt under me, keeping my knees together as I swung my legs in. I slid over making room for Edward next to me. He slid in next to me. We were so close! My skirt had ridden up a bit from the angle of the seat. I looked down at my knees and at a good five or six inches of my hose-shaded thighs exposed above my knees and below my hem … then over at Edward’s neatly pressed slacks with sharp creases, his legs right there in parallel lines close to mine.

Edward, gave the taxicab driver the address. Without a word, he leaned back, turned toward me a bit and smiled. He settled back into his seat and, just moment later, rested his left hand gently on my right thigh right above my knee, tickling at my knee with his forefinger lightly as he said, “This is nice. We’re going to have a good time.”

The entire way to the restaurant, he left his hand where it was, warm on my leg through my hose; and every few minutes, he used his fingertips to tickle at my knee through the hose for a second or two.

That’s how we rode to the restaurant.

Part 6

The cab stopped at a safe place at the curb several doors passed 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. He held my hand softly but firmly as we walked to the restaurant, as we entered, as he greeted the maitre d’ by name, and as we walked into the bar for a before-dinner cocktail.

He held my hand in his for the world to see. He had kept my hand held in his, and, by that simple act, he announced to the world around us that he was happy, proud to be with this woman standing next to him in a blazer, sweater, and tailored skirt. He held my hand in his and that simple act made me feel quite wonderful … valued … and … and … validated. That simple, casual act by this man made me feel more comfortably, more wholly, a woman at that moment than anything 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.

Edward helped me out of my blazer and hung it on a hook. We walked over and took seats at the bar.

Okay, time for the first negative of the weekend. As it turned out, I wound up eventually not considering it much of a negative. In fact, it wound up not having a negative effect on the weekend at all.

But it is something significant. I recognized its significance right away.

Edward knew everybody in the place by name. The maitre d’, the bartender, the hostess, the waitresses, he knew them all … and they knew him.

Although this was a Friday night and there were no other t-girls in sight in the crowded bar, I knew that this was a regular t-girl hangout on Saturday nights. So … I reasoned … as I sipped my white wine … my mind spinning … considering the fact that Edward was so well known at East of Eighth, strongly, very strongly, confirmed an impression I had from our first drink together at that tg-scene club nearly a year earlier.

I thought to myself: “Edward is a player. He’s a ‘chaser.’ He likes t-girls. He understands us and our weird mentalities … maybe better than we do ourselves.”

My mind spun on. “I’ve got to accept it. I’m just ‘another girl’ in his string … just another girl in what is doubtlessly a long string.

“But, so what,” I thought to myself. “So what if he is a ‘player’ in our world. It’s not as if he ever misrepresented himself. It’s not as if either of us ever intimated that we were at a place in our lives where we looking for a life-mate to grow old with. Nor is it as if there is any perception at all that I am in any way ‘obligated’ to do anything … you know … anything I don’t want to do … you know … later. He asked me to dinner and I accepted … and so far, he’s been a perfect gentleman … that’s all it’s been, a dinner date … and all it’s been so far is great fun!”

“But,” I continued to myself, “over dinner, I have to say something about it. I’m not sure what. Something so that he knows that I know exactly what I’m dealing with.

“I can’t, I just can’t have him thinking that I am so naïve that I’m sitting here day-dreaming about a lifelong love in the making. He’s got to know that I know that that’s not what this weekend is about.”

With those few thoughts, I had decided not to worry about it, just to have a good time. I was a woman on a date in a skirt and sweater, sitting in a crowded bar, chatting and joking with the bartender as my date stood close next to me. I had been out and about enough that I sat on the barstool with the experienced posture of a woman, my back straight, my legs wrapped in a tight spiral. I caught a glimpse of myself in the bar mirror as I laughed at one of the bartender’s jokes: a big, comfortable smile on my face, Edwards fingers occasionally running along my shoulders or the small of my back. And he glanced over and smiled sweetly and appreciatively at me regularly.

I had nothing to complain about.

About fifteen minutes after we arrived, a pretty t-girl that I didn’t know well, but had seen around before, came in by herself and took a seat at the bar just a couple of seats down from us. No one in the bar seemed to recognize her as anything other than as she presented herself. But I had my usual t-radar out, so I had noticed her immediately. Edward was chatting with the bartender, so he hadn’t seen her come in. But as soon as he did notice her, he called over to her immediately, “Hi, Tatiana, what are you doing here on a Friday night?”

“Hi, Edward, I’m meeting Chrissy for dinner and a movie.” And then shifting over one stool so she could reach out a hand to me, she added, “Hi, I’m Tatiana. I know I’ve seen you around before, but, I’m sorry, I don’t think I know your name, do I?”

“No,” I answered, “I don’t think we’ve ever been introduced. I’m Cassie.”

“Hi, Cassie. So what are you two up to this evening?”

Edward answered for us. “Dinner … and maybe a jazz club or two. I’ve been trying to get Cassie to go out with me for a year!”

“Well,” volunteered Tatiana, “you two look great together … kind of like one of those typical ‘Upper West Side’ couples.”

“Well, that’s cool,” I said, “since I’m a Jersey girl and Edward’s from upstate.”

“Well, you have that look anyway. Like … I don’t know … comfortable. Not like you are on a first date … but like you belong together.”

“That’s nice,” said Edward, putting his arm around my shoulder and kissing me on the cheek. “I do feel especially comfortable tonight.”

I turned away from Tatiana for a second to look directly into Edward’s eyes as I said, meaning it, “Me too, really, I do. It’s so nice.”

Edward went off to the bathroom and Tatiana and I continued talking.

“So,” I asked straight out, “have you ever ‘gone out’ with Edward?”

“No,” answered Tatiana. “He asked me out once … more than a year ago. But I wasn’t going out with men at that time. And he never asked me again.”

“Well, as he said, he’s been trying to talk me into it for a long time. But, you know, these ‘player’ types. I wasn’t sure I wanted to get involved. But he finally broke down my resistance after a real lot … and what I read as very candid, very open and honest … emails.”

“Well, I’ve never heard any girl say anything bad about being out with him. I’m sure he’ll be fine.”

“I’ll tell you, I’m having a great time so far. It’s kind of … I don’t know … more relaxing being out with a man than by myself or even with my girlfriends. You know, he calls the cabs. He orders the drinks. It’s nice. You feel ‘taken’ care of.'”

“Well, you look great tonight … and, as I said, you two look great together. Have fun.”

“Thanks,” I said, “you’re so sweet.”

Just then, Edward returned. He brought me my blazer and said that we should get upstairs to the dining room before we lose our reservation.

We said our goodbyes to Tatiana … and went up to dinner.

Part 7

With Edward close behind me, I followed the maitre d’ to our table through the crowded restaurant dining room. East of Eighth has a big dining room: over 40 tables crowded with couples and groups of four or more.

I was buzzing with the wonderful feeling of being, as I said before, remarkably unremarkable. In makeup, in a sweater and skirt, in sheer black stockings and heels, with a man walking close behind me, his fingers lightly on the small of my back, I walked through that crowded dining room so pleased with myself that I was having trouble keeping my smile contained into something reasonable.

The maitre d’ held my chair for me; and as I sat, smoothing my skirt beneath me, I pictured in my mind, what the maitre d’ was seeing, what the other diners were seeing, what Edward was seeing as he sat across from me smiling.

We ordered a bottle of wine and surveyed the menus. Edward and I both chose salmon.

Conversation over dinner was engrossing. During the course of that dinner, I “settled” into being a woman so profoundly, so completely, that it would have been more startling not to have, not to sense being inside my woman’s body, my breasts under my sweater, the curve of my waistline, not to be wearing lingerie, not to have my knees held together under the table, my legs in stockings, not to be wearing open-toed shoes, my manicured nails, my tinkling bracelets.

I was, probably, a bit more assertive than a genetic woman normally would be in trying to get a sense of who Edward really was and how he happened to be sitting there opposite me; but I couldn’t help it.

“So, tell me,” I said.

“Tell you what?” asked Edward.

“Well … start with the obvious. Why me? There are dozens of gorgeous young girls at the club that would be absolutely delighted to be going out to dinner to a nice restaurant with you. Girls in their twenties, girls with young, smooth, glowing skin … and tight bodies … and all that. Why an ‘ol’ bag’ like me.”

He chuckled out loud and said without hesitation: “Been there, done that.”

That made me laugh.

“No, seriously,” he continued, “I know it’s a cliché, but it’s true. I’ve done my share of dating the young girls … especially those gorgeous young Phillippine girls that are always at Ina’s parties … with their dark eyes and full lips … and that silky black hair down to their waists.

“But, again, I know it’s a cliché, but it’s true: did you ever try talking with them?

“After a few minutes with them, I run out of things to talk to them about … truly … I truly do. I can tell you, all they know how to talk about is movie stars and singers, dance steps, make-up and hair. I try to tell them about a course I am taking for my 35mm photography hobby and they couldn’t care less. I try to talk about my work and they have no clue what I’m talking about. I try to tell them about my family and their eyes glaze over.

“I’m telling you that I’ve been there, done that, and every once in a while it’s tempting to try again … and I always regret it before half the date is over.”

I smiled and couldn’t resist asking, “So, is what you said downstairs to Tatiana really true then? Are you,” I could feel myself actually blushing as I asked, “are you … you know … truly having a good time tonight … so far I mean … tonight … are you … you know … happy that we’re out together tonight?”

“It’s great. It’s really great … truly. This is a lot … a lot … better … a lot more … more … comfortable. You know, I don’t like to get stared at either, you know. And I do when I’m with those girls … no matter how great they pass. We just don’t look right together. We … you and I … we just look more natural, more right together … and I think I just ‘feel right’ with you … it just feels better, more comfortable, that’s all.

“And are you,” he continued, ” … are you having a good time?”

“Fabulous … you have no idea how nice it is for me to be out with you like this in this nice restaurant. I just can’t even express how great it feels to be me and to be here like this with you.”

“Good … and the night is still young.”

“Will you get mad if I keep up my ‘cross examination’ a bit more?”

“I don’t feel as if I’m being ‘cross examined.’ If it makes you feel more comfortable, I don’t mind talking about myself … who does? But, of course, sometimes over the weekend, you’re going to have to tell me more about you and your life and your feelings, too. Turnabout is fair play.”

“Agreed,” I said, and reached across to shake his hand.

He shook my hand for just a second, then brought my fingers to his lips and kissed them lightly … then again. Seeing it, feeling it made me smile. And it … it made me shiver.

“So, shoot,” he said letting go of my hand. “Ask away.”

“Okay,” I said, “here goes. Have you always been ‘into’ t-girls?”

“Oh no,” he responded immediately. “I never went out with a t-girl in my life until about five years ago.”

Over the course of dinner, I learned a lot about Edwards life and, with some not-very-subtle prodding by me, particularly his romantic life.

In short, he was married for nearly 25 years and had two grown children. For the first five years after his divorce, his dating and romantic life was typical … and continued to be totally hetereosexual. He dated girls and women … and came very close to marrying one of them. Entirely open to my probing, I even learned that in his entire previous life, he had only had one not-totally-straight relationship … a short-lived bit of sexual experimenting with his best friend in eighth grade that had ended when his friend wanted to “do stuff” that Edward wasn’t willing to try. Telling me about that, he ended with, “God, I’ll tell you, I never even told my wife of 25 years about that stuff that happened back when I was in junior high!”

His interest in t-girls was first sparked by a drag club. (I won’t digress here to relate our long aside discussion on the distinction between drag and tg. Suffice it to say, that by that time, his opinions were already well considered and well formed and not that different from my own.)

He had gone to the drag club, which was not far from where he lived in Florida, with friends, but he found himself going back again and again by himself. As a bachelor, his time was his own, and he found that going to that club was almost always his first choice when he was free.

Even though several of the performers were strikingly beautiful, he never asked any of the girls at that club even to have a drink with him. But he did find that they were now becoming part of his romantic fantasy and sexual fantasy lives.

From that point, it was not hard to find his way to a club freguented by transsexuals and crossdressers in Miami. And those girls he did start dating almost immediately.

Edward blushed himself when he got to this point, but, with just a bit more proddying by me, pressed on, as follows: “… and … and … I found … even though, honestly, I had never had another ‘gay’ relationship in my life before that … that I … um … ah … well … you know, in intimate terms … what can I say … I liked it … I liked it immediately … I found it very ‘exciting’ being with these girls almost immediately.

“I don’t know why. I truly don’t. But I liked it immediately … and I … you know … I like it to this day.”

“So,” I ruthlessly pressed, “do you never go out with genetic women anymore?”

“No, not really, not anymore, not in over three years with a regular woman.”

“But,” I pressed, “you seem to know everyone in this restaurant. And you know everyone at Ina’s and Karolyn’s club parties. So … I guess you really qualify as what we girls call a ‘chaser.'”

“I guess that’s true. I mean I don’t like to think of myself as a pathological philanderer. But, it’s a funny world, this transgender world. Girls drop into it … then disappear for long periods. And because of my work, I’m usually living in two or three different places at once. So, I guess, yes, it’s true. I’ve wound up dating and ‘being with’ lots and lots of different girls over the five years I’ve been doing this.

“But, believe me, often all I do is go and hang around the clubs for months at a time. In fact, this is the first real date outside the clubs that I’ve had in nearly five months.”

I never doubted Edward’s history as related over dinner that Friday night. He had no reason to lie. And I don’t doubt it until this day.

I recognized immediately that Edward’s particular history provided a wonderful benefit for me (as it would have for most any t-girls in my position). Edward was a gentlemen. He was a gentleman who had been romantically involved only with genetic women for nearly all of his life. Edward had (and has) known me, only as the person who “presents” to the world as a woman.

So, his ingrained habits of a lifetime were to relate to me only as he would to any woman. He didn’t have to think about it, to strain, to hold the taxi door for me, or to hold my hand walking into a restaurant, or to reach across the table and take my hand to kiss my fingers. I was the beneficiary of a lifetime of habit of how a man relates socially to a woman. That’s the whole of how Edward related to me as a woman.

How nice that was, how very nice.

How nice it was when, after I had refused dessert, Edward, without asking me, asked the waiter for two forks with the dessert he ordered. How nice it was that when the dessert arrived, he put the plate into the middle of the table and insisted I take one of the forks. How nice it was that, as we picked at the single dessert together from across the table, he held my eyes with his eyes and with his soft smile the whole time.

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

Part 8

I put down my dessert fork, took a last sip of my coffee and said to Edward, “This has been such fun.”

“But, you ate barely half your salmon and only a few forks-full of our dessert.”

“I’m sorry. Everything really was delicious. I guess I’ve just been too excited to pay much attention to the food … and … and … I was fascinated hearing about your life over dinner. I really liked getting a better understanding of how we happened to be sitting here as a … uh … as a man and a woman on a date, as a … a couple, tonight.”

“Well, that’s what we are. We’re a couple on a date. And I’m having just as much fun too. And the night is not nearly over. I promised you some jazz … and I know just the place I want to go. I’ve only been there once before, but I loved it last time. And I checked … and it’s still there.

“I’ll get a check and we’ll get going.”

“Okay, excuse me a minute, then. I’m going to go ‘powder my nose.'”

“Good. I’ll ‘hit the head’ too on the way out. I’ll meet you down by the front door, okay.”

“Sounds great.”

There was only one other woman is the Ladies Room in the restaurant. Women always seem to exchange small greeting words or smiles in Ladies Rooms. We did that, but she paid me no other special attention beyond that as she washed her hands, and as I ran a brush through my hair, reapplied some lipstick, and sable-brushed some blush back on to my cheeks.

Before going to meet Edward at the front door, I peaked into the bar, but Tatiana was gone.

As Edward held my jacket for me and I slipped into it, I reported to Edward that I was sorry that I had neglected to ask Tatiana for her email address when we had met earlier in the evening. He told me that he might have it at home and that if he did, he would send it on to me, then added, “But anyway, we might want to stop here for a drink before dinner tomorrow night too … and she’s almost always here for drinks before dinner on Saturday nights … so you’ll probably be able to ask her then yourself.”

“That’s great,” I said. “I really liked her. Thank you for introducing us. And did I tell you … we learned when we were talking earlier that we live very near each other in New Jersey.”

The phrase “dinner tomorrow night,” said so incidentally by Edward, was reverberating in my head, as I realized: Wow! All this already … and tonight is still only the very start of this weekend!

By this time, we had made our way out of the restaurant on to a sidewalk crowded with people making their way to the big cineplex next door. As we made our way through the crowd, I was struck once again with how incredibly comfortable I was feeling, how much I had settled into my role as a woman out with a man on a Friday night.

Edward suggesed that we walk down the block a bit to get away from the movie crowd before trying to hail a taxi. I found myself slipping my left hand through Edward’s arm, resting my fingers over his bicep, our gait together naturally comfortable, walking so tightly to him that I could feel, through my sweater and blazer, the pressure of his arm against the side of my breast.

Edward looked down at me and smiled, and 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?”

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

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

“Does everyone just call you ‘Edward?” I asked.

“Some of my friends call me ‘Ted'” he answered, “and my mother called me ‘Teddie’ right up until the day she died.”

“Actually, I kind of like ‘Teddie’ for you.”

“I don’t know … it’s always sounded like ‘little boy’ to me … not this ol’ senior citizen that I’m becoming too quickly.”

“No, I think the ‘-ie’ sound at the end of words has two different possible meanings. The first is what you said … the dimunitive … as with a child. But it also has a sense of … I don’t know … familiarity … you know like the familiar tense in a romance language … even … you know … affection.”

“Yeah, sure, I guess that’s true. I guess I wouldn’t be surprised to find a woman with whom I had special feelings calling me ‘Teddie.”

“Well, that’s a little too early for us yet, I think … I guess I’ll stick with ‘Edward’ or ‘Ted’ … for now.”

Edward smiled at that and said, “Do call me ‘Ted.’ I think I’d like that.”

“Okay, ‘Ted’ it is,” I said.

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

The cab heater was off or set too low and Ted put his arm back around my shoulders in the cold cab as we rode down toward Greenwich Village. I felt totally comfortable snuggling in close to him against the cold in the cab. I half expected him to kiss me during the trip dowtown, but he didn’t.

Ted had misremembered the exact location of the jazz club. He had the cab drop us off at Sheridan Square (a busy crossroads made particularly famous by the ‘Stonewall Riots’ of 1969 that helped lauch the gay rights movement). But, then out on the sidewalk, he did this comical little 360 degree turn, looking around and saying, “I now 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?”

The sidewalk was crowded with passersby, so I stood in the shadow of a closed newstand to keep out of the flow of foot traffic. I remembered having stood in that exact spot as Cassie several years earler, out alone on a cold night, just wanting that night only to be outside, to be a girl, to be a woman out in the world. Younger and thinner then, I probably looked better then than now. But that night, waiting for my date to rejoin me on the sidewalk, I stood there so deeply in the unselfconscious comfort of my gender role of that evening, that my focus wasn’t on the idiosyncrasy of who I was and where I was in the same way that night as I had been that previous time.

Instead, I was totally relaxed in who I was. I knew from the depths of my soul that those deep inner feeling of gender comfort that night so radiated from me that, like magic, no matter if my hidden body might deny it, I was a woman, a woman in the universe that night to the people around me, to my date, to the universe, itself … and especially … to me, to myself.

Ted, my date, came out of the bar and grabbed his date’s hand, 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.”

We had started too late across wide Seventh Avenue. The blinking “Wait” sign came on before we were a half dozen steps into the street; and became steady when we were just half across. Ted pulled on my hand, and we started running to get across the last part of the wide Avenue before the unsympathetic New York traffic started to bear down on us.

Running in heels across a New York avenue. Trailing a step behind a man holding and pulling me by my hand. All those years of practice paying off. Running like a girl. Running like a woman. (NO, not running like a mincing drag queen.) Running like a woman does, my hand swinging with my gait. Running and smiling widely, then giggling, then fully and breathlessly laughing the last half dozen steps.

And when we reached safety on the far side of Seventh Avenue, Ted pulled on my hand, turning me toward him, grabbed my other hand, pushed our hands down toward the sidewalk, pulling me close to him, smiling widely as he bent over and kissed me quickly, but firmly on the lips. No one noticed. No one cared, as he held the kiss long enough, just long enough, that I felt my eyes closing of their own volition as I sank sublimely into the feeling of being a woman being kissed by a man like that on a public street.

Then he broke the kiss and started pulling me across Christopher street toward Arthurs, the jazz club to which we were headed. I managed to keep up with him despite how flushed and how filled I was with the unnamed feelings that came with being kissed like that, in that place, in that way.

A club guard opened the door for us and we entered the crowded club; we entered animated, smiling, and holding hands.

Part 9

The club was crowded, but either we were lucky or Ted had slipped some money quietly to the man who seated us, because we got wonderful seats. We were put at a table close to the band and with great sight lines, but off to the side of the room, away from the bar that ran the length of the club. Although we were close enough to feel connected to the musicians, we were far enough away from the crowds jostling around the bar to be comfortable.

The band was great. They were Jamaicans and Jamaican-Americans playing jazz: Reggae beats, but with a progressive jazz sensibility. It made for a mix somewhere in the middle of a jam band, a jazz band, and a reggae dance band.

We had come in near the end of a set and the band went on break within ten minutes of when we were seated. We had been seated sharing a tiny table with another couple. Friendly, Midwestern tourists, they introduced themselves to us almost immediately during the break.

“Hi,” said the man, putting out his hand across the table to Ted, “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 Ted, 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. Are you guys big jazz fans?”

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 … so simply … so matter-of-factly … I loved it!

Karen answered for them, “Well, I’m more of a real aficionado than my husband is … I mean, I already know this group … and I even have one of their cd’s … even though I had no idea that they were going to be here tonight. But, anyway, Bob likes to go to the clubs, too. He just doesn’t listen to jazz cd’s as much as I like to.”

I responded with, “Well, I guess we’re just backwards from you two, then. Ted knows a lot more about Jazz than I do. But I always do like it whenever I get myself out to a jazz club.”

Even though we had barely said a dozen words to each other, Karen surprised me when she didn’t even blink before jumping 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,” Ted answered, without hesitating, and with calm candor, to Karen’s rather forward question.

“No,” he continued, “this is new for us, but … it’s…”

He hesitated just a second, then smiled at me and went on, “it’s nice … really nice.”

And with that, he kissed me on the cheek.

I blushed a bit, but, without even thinking about it, found myself turning my face toward Karen, so only she could see, smiling, and kind of raising my eyebrows to share with her a pleased-with-myself 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 grin was clearly meant to share back with me that she was pleased for me that 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 that we were immediately sharing as 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 minute earlier. But my funny facial expression and her hand on mine in response was an immediate and private “women’s conversation.” It was an expression of immediate support by this stranger to another woman, a conversation that didn’t need words.

It was altogether a very feminine, a uniquely woman-to-woman, kind of connection. I had had my first natural “vagina dialogue:” a kind of connection that I recognized immediately was unlike any I had ever experienced in my life before, a special kind of natural connection that exists between women and that is different than any kind of connection any man ever experiences. I knew immediately and without question that that interchange was one of the most unconsciously purely feminine things I had ever done, one of the most feminine experiences and feelings I had ever had.

Yet again, I was topping the earlier events of this evening. I had entered the world of women in a new and profound way.

I was so overwhelmed by my feelings that I shut my eyes for a moment. I all but expected to feel a wave of magic sweeping over me, changing me with its magic, miraculously re-forming my body to agree with the deeply feminine place into which my mind and emotions had traveled as I sat there at that little table, a mysterious magic coming from some unnamed goddess to secretly re-shape my body under my clothes, to transform my body down there … down there in my underwear … to be … to be as … as it should be, changing me physically, changing my body, changing me, even as I sat there in that crowded, noisy club.

Although I consider myself a crossdresser and not a transsexual, with my eyes closed at that moment in that club, listening to the sounds around me, I all but waited for, prayed for that magic to begin.

Then, just as I began to feel the first pangs of mourning that the magic would, of course, not really come, 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, Ted’s lips softly, first on one of my closed eyelids, then on the other, that woke me from my little dream.

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. I saw Ted’s eyes closing in the kiss even before mine. I let mine drift close again also, letting them drift closed to better focus on the feeling of his warm, soft lips on mine. As he held the soft kiss, I brought my fingertips to his cheek to encourage him to hold the kiss still longer, to hold it a second more, a second or two longer. And he did.

And Karen smiled at us again.

And my breaths were coming short and shallow.

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.

At one point, Ted and Bob got into one of those horrid conversations about different golf courses they had played and Karen immediately made us all move around so that she and I were next to one another. Again, I was astonished at how easily I found myself unselfconsciously settling into a woman’s conversation. Now, don’t call it sexist stereotyping; it’s just what happened, as we talked women’s talk: talked about our grown children with pride, about the department stores in New York and the boutiques on Madison Avenue, about the books we’d been reading, about the forthcoming Spring’s fashion trends (“Did you see all that white coming back for this Spring?” “Yes! And espadrilles, isn’t that great that espadrilles are coming back!”); and especially about relationships, about close girlfriends that go back for years, about the men in our lives, about the men in our friends lives, about men in general, about men, as if they were another species.

At one point I spotted three t-girls come in together and sit at the bar. They were much younger than I, and prettier, but attuned as usual, I recognized them as t-girls immediately. No one else in the club seemed to be paying them any special attention. I saw them turn in unison on their bar stools to survey the crowd, and I couldn’t help but smile to myself as I saw their eyes flick quickly over the two middle-aged couples in conversation at the little table across the room.

That night at least, I was part of that other mundane world, not their world.

Meanwhile, the four of us were having such a good time together that I soon forgot they were even there and never saw them leave. Before the evening was over, we had, all four of us, exchanged email addresses; and surprisingly, at least Karen and I actually used them … and are using them still as e-girlfriends.

We left the club together.

Being gracious to the out-of-towners, 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 against the gathering cold.

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

Part 10

Unlike the freezing cab we had taken downtown, the cab that picked us up for our trip back to our hotel was warm and comfortable. Nevertheless, I slid in only halfway across the wide back seat; and when Ted got in after me and closed the door, I hesitated for only a moment before tucking in under his arm, putting it around my shoulders, letting my head drop on to his shoulder, and shamelessly snuggling in against him.

Ted didn’t seem to mind. 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, very female.

“Those were such nice people, Bob and Karen, weren’t they?” he said softly.

“Ummm,” I responded, so warm and comfortable and happy and sleepy, I wasn’t sure I wanted a conversation.

What I actually wanted … was to be kissed.

I wanted to be held. I wanted Ted to want to kiss me. I wanted him to want to hold me, to want to touch me, to want to touch … to touch my breasts. I wanted him to kiss me … and to cup one of my breasts … and to touch and to hold one of my breasts in his hand for all the rest of the ride back. That’s what I really wanted.

As a crossdresser, my breasts are not my own. But they are expensive and soft and proportioned 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.

Sex is doubtlessly just as much a phenomenum of the mind and imagination (and heart) as it is of the physical body. There is no way that I can know for sure how far removed my own sexual response is from a genetic woman’s sexual response; but I can report to you that my sexual reaction to watching and feeling a man caress my breasts, false as they are, can be remarkably intense. Despite the lack of applicable nerve endings, at least to me, its seems that my response to a man touching my breasts is more like than more unlike any woman’s reaction. In short, I find it very hot!

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 we talked 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 had thought before that evening that that’s all I ever really wanted as an “occasional” woman. That’s what I always told myself. That’s all I wanted, just to “be,” to be a woman … on occasion.

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

I was absolutely taking being a woman at that time in that place for granted.

Instead of just being satisfied, just treasuring being a woman, I was hungering for more. Instead of just treasuring being a woman, I found myself also hungering for exactly what a woman hungers for: to be loved.

Oh, I don’t mean loved in that important way, not certainly on a first date!

No, not loved in that profoundly important way; but still, at least, to feel that this other person, this man, is really liking you, is truly enjoying, at some level even loving, being there with you. To feel that he really wants to kiss you, that he wants to be with you right then and there … and wants to kiss you as much as you want him to kiss you. It was a deep, inherent, instinctive woman’s need to be desired. To be loved … at least in that way … at that time.

No! No, it’s not just lust 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 romantic possibility … the possibility of profound connection between people. It is about those first traditional steps toward … well … toward that other kind of love, that profound kind of love: every … every … every woman’s dream.

It’s as significant… and as simple … as that. If you don’t dream about being loved as a woman, than you are not transgendered. Or rather, if you are transgendered, than whether you realize it yet or not, than you do or will dream about being loved as a woman.

At some level, all we transgendered, from the most hurried, most “sometimes,” most closeted secret crossdresser to the most successfully deep-stealth post-op transsexual, we all have our romantic dreams.

We do not just dream about walking down the street as women. At some level we all want to be desired; we all want to be loved. Of course, that’s not to say that the person we dream of loving us is, himself or herself, necessarily one gender or another. Just that that person can, at least at times, love us as women. And we want that. And that’s why being transgendered is not fetishism, why it is not just about the clothes we wear.

As t-women, at some level, we want to be loved in just exactly the same way all women want to be loved. And that way is different than the way men want to be loved. (How those two ways are different is a subject for another whole essay!) But, at t-women, it is absolutely the woman’s way that we crave.

But Ted didn’t kiss me in the cab.

But he did continue 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. But we didn’t even have to ring the bell. The front desk was attended 24 hours per day, the front doors were visible from there, and 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 pleasantries 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.

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.

By the third floor, I had dropped my purse on to the floor beside me, and my body had melted totally against his in the kiss. But still, he stepped forward until my back was against the side of the elevator wall, as if he wasn’t satisfied, as if he needed for us to be pressed even tighter against one another.

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

Ted’s tongue tickled at my lips. I softened and opened my lips, wanting, needing that next intimicacy . His tongue started with gentle little ticklings on my teeth, then against my own tongue. Then the roof of my mouth. Then deeply into me. I felt myself swirling down into the enveloping whirlpool of the kiss.

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 and arched my back, pressing against him in soul-shaking passion.

The elevator doors opened and stayed open on the empty, quiet hall of the top, ninth floor; and still we were entangled, now with Ted’s hand out from behind my back and forced in between us and through the opening of my blazer, to hold and knead at first one breast and then the other.

My head was spinning. My knees were like rubber. If it were not for the pressure of Ted’s body holding me against the elevator wall, I think I would have sunk to the floor of the elevator.

Finally, as I felt Ted’s other hand come out from behind my back and move to my skirt hem, then felt his fingertips starting to slide tentatively up under the hem, up my leg, up the inside of my right thigh, 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 started to move slowly down to our floor.

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Category: Transgender Fun & Entertainment


About the Author ()

Cheryl Ann Sanders was a frequent contributor to Transgender Forum in the past. She has been absent for several years while writing and publishing a (quite successful) straight novel under another name.

Comments (2)

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  1. says:

    T ed is a nice guy. I would love to meet a man like that.

  2. cddon cddon says:

    You Go GIRL!!!

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