Backwards in High Heels

I'm told that when I was two or three, my mother dressed me as a girl and took me trick-or-treating with my older sister on Halloween, but I have no recollection of the event.

* * *

Fast forward ten years, when I was on the brink of puberty. For some reason which I will never understand, I developed a fixation on trying on my mother's high heels. One night, when she was out playing bridge, my father was out of town and my sister was off somewhere, I snuck into her closet and opened one of her shoe boxes – she kept her shoes in boxes piled up in neat rows on the floor. I tried slipping one of her heels on, but it didn't fit! So I opened another box, and another and another, with the same result every time: my twelve year old feet were too big for her shoes!

Then, an inspiration came to me: didn't she always wear her shoes with nylon stockings? Maybe, if I put one of them on, I might fit into her shoes? I fished one out of a dresser drawer, and tugged it halfway up my leg. Then I tried to step into one of her shoes, and like magic, my silky foot slid right in. Another stocking, and I was taking my first tentative steps in high heels. It was the beginning of a lifelong, secret journey into the world of femininity.

There have been many detours along the way. For the next several years, I had to confine my explorations to stolen moments when my parents and sister were out of the house. Then, one fateful Sunday morning, my parents loaded up the car to drive my sister to the airport, so she could fly halfway across the country to begin her freshman year at college. The airport was an hour's drive away, which meant I'd have a good three hours to attempt something I'd been yearning to try: a head to toe transformation from boy to girl in my sister's clothes!

As soon as the garage door rolled down, I walked into her bedroom. With trembling anticipation, I put on a pair of her cotton panties and one of her old bras, which I must have stuffed with tissues or something, and then I tugged on one of her girdles (girls and women wore them in those days) with clips on the bottom for nylon stockings (pantyhose had yet to be invented) which I tentatively rolled up my still-hairless legs. It took me forever to get the hang of it, but eventually both stockings were snug and tight, and I dropped a lacy white slip over my shoulders. From her closet, I selected a tight skirt and matching sweater, which fit me like they'd been made for me. Her shoes were too tight for me by then, but my mother's closet yielded a pair of low heels which still fit, and then it was time to try on some of her makeup. But before I could get there, I lingered in front of a full-length mirror to admire my reflection.

From the neck down, I was a teenage girl in a cute skirt, heels and stockings, which felt so good, and so right...and seemed so wrong! What was I, some kind of pervert? My euphoria was replaced by feelings of shame and self-loathing, which lingered long after I tore off my skirt, sweater, shoes, stockings and lingerie, and put them carefully away, lest my perversion be discovered by my parents and sister. For the first – but hardly the last – time, I vowed never again dress like a girl, and prayed that I'd be able to redeem myself somehow and live a normal life.

* * *

Fast forward another twenty years of normal, white bread manhood. A successful businessman, I'd climbed the ladder of success, my youthful flings with crossdressing almost forgotten. But not entirely: every scrap of literature, every movie like "Tootsie" or "Victor Victoria", every news article featuring some bizarre female impersonator, had been salted away. Although she was buried deep within me, my inner woman was patiently waiting for her moment to reemerge, and when she did, she came out with a vengeance.

Once again, she had to wait until opportunity opened the door for her: after slogging it out in the corporate trenches, I landed a dream job with a fat expense account, which required me to spend a lot of lonely nights in luxury hotels. With nothing but time on my hands, I began to fantasize about what it would be like to dress myself up as a woman once again. This was in the days before the Internet, but there were other means for a resourceful lady to assemble a trousseau: does anyone remember those thick Sears catalogues, with page after page of sexy models wearing beautiful outfits? That's how I bought my first dress...

I got lucky with my shoes: one of the girls in the office (who had very big feet) used to change into comfortable flats every day, and when she quit on short notice, she left them behind in the hall closet. My wig? With Halloween approaching, I explained to the clerk at a wig store (with genuine embarrassment) that I needed one for a costume party. My teddy and slip were purchased a few days before Christmas (for the woman in my life!) and that's how I acquired fashion jewelry and accessories too. That left makeup, the biggest challenge of all, which I solved rather ingeniously by presenting myself to the cashier at an all-night drug store with a basket full of cosmetics and a list written in a girlish hand (mine) explaining that the airline had lost my wife's suitcase, including all her makeup, and she'd sent me to replace it!

Two nettlesome problems still bedeviled me: my legs were overgrown with hair, as were my arms and the backs of my hands. The solution to the first problem came to me when I read an article in the Sunday paper about a female impersonator who hid his hairy legs under two pairs of opaque tights (first white, then flesh colored) followed by whatever nylons went with his outfit. I tried it, and it worked like magic! As for my hands, a pair of long opera gloves, which would slide under the sleeves of my dress, did the trick.

Finally, on a dark winter's night, I checked into one of my favorite five star hotels with an extra suitcase filled with all of my female acquisitions. After a long, hot bubble bath in fragrant suds, I wrapped myself in a plush terrycloth bathrobe (courtesy of the hotel) and began to experiment with makeup. What a comedy of errors! My eyes looked like a raccoon's, my foundation caked on my dry face, and my bright red lipstick make me look like a hooker. Wiping it all off wasn't so easy either (makeup removal pads finally took care of that problem) and eventually, by moisturizing my face first and using less of everything, over time I was able to create a presentable look. My first wig left a lot to be desired too, although it looked a lot better after I figured out how to style it with clips, scrunchies and yarn bows.

Back to that first night: as disappointing as my initial makeover was, I did look decidedly female from the neck up, and once I pulled on my two pairs of tights, my legs looked like a girl's. What a delight it was to slip into my lingerie and stockings, and put on my first dress – my dress! My leftover shoes pinched my toes, but they fit okay, and when I surveyed the finished product in the mirror on the closet door, that same old sensation that I'd experienced the first time I ever did this, as a callow youth, came on with a rush, only this time I knew exactly what was happening to me. Once again, I lost myself to the throes of an exquisite orgasm, followed by the same feelings of shame and self-loathing, only less intense this time...not the orgasm, which felt as good or better than any I'd experienced during sexual intercourse, but rather the remorse, which quickly faded away.

For better or worse, I finally admitted to myself, I was what they used to refer to as a transvestite: a man who derived sexual pleasure and release from dressing as a woman. This was not going to define my life, but now that I had the means to do so, I could make it a sort of hobby, a harmless alternative to fooling around with women. Such were the rationalizations that propelled me along for the next several years, as I gradually became more accomplished in my self-taught feminization techniques, learning what styles looked best on me, perfecting my makeup, and eventually venturing outside my hotel rooms onto darkened streets, and then eventually into the light of day, to window shop or purchase a newspaper – the first time I did, the clerk said, "Thank you, ma'am," which made my day. Limited as I was by the fact that I was wearing gloves and three pairs of hose, my activities were necessarily confined to the winter months, and there were more than a few embarrassing moments – like being called out on the street, "that's a fucking man!" – which caused me to purge my entire supply of women's clothing, more than once, and to vow never again to engage in such madness.

* * *

I should have been a double agent! All those overnight trips "packing for two" and nobody who knew me ever had a clue. Of course, my female paraphernalia was carefully squirreled away in hiding places which were never discovered, and my inner woman seemed satisfied by her part time status, or so I thought. Once again, opportunity knocked for her: I was offered a fantastic job in a big city on the other side of the country, and the job paid so well that I could afford to get myself a smart apartment downtown.

I think you can guess what happened next: after a long, lonely winter, glorious spring finally came, and all the girls I encountered in the street were happy to ditch their parkas and galoshes and start wearing cute, summery skirts and dresses. They were like butterflies coming out of their cocoons, and my inner woman wanted to join them! By then, I'd gained a lot of weight – too many burgers and beers with the boys – and my body hair remained a problem. Until I came up with the perfect solution, a sort of crossdresser's weight and exercise routine: eat like a girl, shave like a swimmer, and hit the health club. When the weight started to disappear, I began to look and feel much better as a man, and my absence of body hair was kind of trendy in a metrosexual way. I caught a wave, and my inner woman rode it right along with me.

What a joy it was to finally be able to shave my legs, and to feel and see them in sheer nylon stockings! To be able to go shopping, as a woman, for women's clothing – to actually get to try on a dress to see how it looked on me before I bought it! I can close my eyes and remember in vivid detail the way it felt to walk down a sunny boulevard in a sleeveless dress, passing by all the drones in their uncomfortable suits and wingtips – heaven! I took to wearing sunglasses so I could stare at people without them knowing it, to see if they were staring back at the man in a dress, and wonder of wonders, they weren't! I was just another pretty woman making her way in the world...and yes, I was pretty, and I knew it, with a trim physique, a flattering hairstyle (a good wig makes all the difference) and a newfound confidence in my step.

The triumph of my inner woman coincided with the dawn of the world wide web, and the explosion of readily available information about men who dress as women was a revelation. No more trips to the library to thumb through card catalogues for topics related to "transvestism" and no more furtive visits to adult bookstores! I also began to "meet" kindred souls via chat rooms and Internet forums, finding many other men who were wrestling with their own inner women, and eventually even meeting some of them in person. This eventually led to the next step in my evolution, and it's a long story...

* * *

I met a "girl" named Rachel on a crossdressers website, and we had a lot in common: her pictures were gorgeous, and she said she loved to go shopping and do mainstream stuff as a woman, as I did. Rachel lived in a city that I visited often on business, so I suggested that we get together (as girls) the next time I was in her town. She readily agreed, and after she assured me that she was "drop dead passable" as a woman, we set the date.

On the appointed evening, I dressed myself in a cute skirt and sweater and waited for Rachel to show up. She was very late, but finally I heard someone grunting outside my hotel room door, and "she" knocked. When I opened the door, there stood before me a sweating, strapping man juggling two suitcases and a garment bag, who apologized (in a deep, disk jockey's voice) for being so late. Rachel disappeared into the bathroom, and for the next hour and a half I waited patiently in my room while "she" effected "her" transformation. When she finally emerged, the results were tragic: Rachel looked like a truck driver in drag, and my heart sank at the prospect of going out in public with her, since she would obviously be clocked by everyone we met, dragging me down with her. We made it as far as her car, when I finally screwed up my courage and said, "Time out. We can't do this. I can't do this. I'm sorry, this isn't about you, it's about me – my ego is just too fragile to go out with you."

Of course, she was devastated. We slunk back to my hotel room, and I waited uncomfortably while she returned to the bathroom to turn herself back into a man. When he was finished, "Rick" sat down on the sofa and we began to talk. As horrible as he looked as a girl, he was extremely good-looking as a guy, and the burly physique which doomed him as a woman made him a very attractive man. We sat there and talked for hours, and I found myself becoming fascinated by him. What a life he'd led! After flunking out of one of the best universities in the country, he'd hitchhiked to New York, where he fell in with a young artist named Andy Warhol, and became one of his infamous boytoys...there was a lot of heavy drug use, and his parents had him institutionalized for a time, but after unscrambling his brains, he became a computer wizard and had an amazing career. But a bad marriage had wiped him out financially, his health went to hell, and he was flirting with crossdressing as a sort of escape.

When he finally got up to leave, I apologized once again for crapping out on him, and said, "You know Rick, if you ever feel like going out sometime, with you as the guy and me as the girl, I'd like that." To this day, I don't know why I said it, but to my surprise, he said he'd love to. So when I told him I was returning a few months later, he asked me out to dinner!

Try to imagine the thrill of getting dressed and putting on my makeup, for a date with a handsome man. He was such a gentleman – I think he even brought me flowers! He opened doors for me, asked me what I was going to have for dinner, and smoothly informed the waitress, "The lady will have..." So what if we were only at a neighborhood Applebees? I was living a dream, as we chatted like any other man and woman over dinner – he was such a fascinating conversationalist! When we left the restaurant, he took my hand, and I felt an electric shock throughout my body. Sitting in his car on the way back to my hotel, I never wanted that evening to end, and after he walked me to my door, I surprised him – and myself – by giving him a kiss.

Thus began my first love affair with a man. Rick, as it turned out, was impotent by then (too many drugs and psychiatric medicines) but we dated off and on for several years. It was almost like we were high school sweethearts, kissing and petting but never making love to each other – I was far too shy, and he was incapable of forcing the issue. His financial situation was becoming more and more dire, so I wound up paying for dinner most of the time (or should I say, my company paid, since I was traveling on an expense account) and one day we even went swimming together.

All good things must come to an end, although in Rick's case it was heartbreaking. As his decline precipitated after two DUI arrests, it became more and more painful to witness his deterioration. In one of his last emails to me (I've saved them all) he told me that I was the best thing he still had going for him, and we made plans to meet at a fancy hotel, where I would fulfill one of my fantasies: ballroom dancing in a little black dress and high heels! But when I emailed him to confirm the date, he never responded. It wasn't until a few weeks later that I learned the awful news: Rick had committed suicide, gassing himself to death with exhaust fumes from his car. I learned this from another crossdresser who knew Rick, and knew that we were close. Such a tragic end to a wonderful, if deeply troubled, person!

* * *

It took me a long time to get over the death of Rick, but life goes on, as always. At least I didn't have to blame myself: he was always happy when he was with me, but our moments together were a rare respite from his otherwise dismal existence. For a long time, I contented myself with making "girlfriends" of other crossdressers I met on the web, including in a few cases their amazingly supportive wives! I worked very hard on my biggest flaw – my voice – learning how to talk like a woman. But I missed having a man in my life, and eventually I started looking for another lover.

There is an endless variety of Internet dating sites, some catering to guys who dig chicks with dicks – I've always wondered why so many otherwise straight guys have a thing for girls like me, and it's my theory that a lot of them are as turned on as I am about dressing in women's clothing, but don't have the balls to admit it or try it. But I digress: it didn't take me long to find the man who took my virginity. Shall I tell you about him?

He was an air force pilot, training out of a base near me. We flirted online for a while, and eventually he asked me out. I was so excited! I can still remember what I wore for him: a clingy pink top, a full skirt with matching pink flowers, nude pantyhose and black skimmer flats.

He was nice looking, not as gorgeous as Rick, but very clean cut and respectable. He was a few inches shorter than me, and I was so glad I wore flats! His name was Ron, and he took me to a little Italian bistro a few blocks away. We sat at a table on the patio outside, and I noticed him studying the other customers while we waited for our pizza. At length he said, "I've been trying to figure out if anybody here realizes that you're a guy, but nobody seems to notice." Boom! After we enjoyed our dinner and a few glasses of wine, he walked me back to my place, and this time he took my hand...after I let him in, and poured us each another glass of wine, one thing led to another, and before I knew it I was in bed with him, my skirt pulled up and my panties and hose pulled down. He proceeded to go down on me, giving me a delightful blow job - my first in decades - and before he knew it, I came in his mouth! I was lost in ecstasy, and after I came down to earth, he marveled at how quick I was.

Then he asked me if I had a condom! I did, and I watched with alarm as he put it on and told me to put a pillow under my butt. I started to protest, but he was very much in command, and before I knew it I was on my back, my legs were behind my head and his penis was inside my ass. It hurt a little at first, but he was very good and he knew what he was doing, so I just let him have his way with me. He found his rhythm and his thrusting became deeper and deeper, and it felt so fucking good! I was becoming a woman, and I just closed my eyes and reveled in the moment. Soon he cried out, and I felt him pulsing inside me, and then it was over. "That felt so good it hurt," he said. He left soon afterwards, leaving me to contemplate what just happened to me: I had sex with a man. Did this mean I was gay? No, it meant I was bisexual, right? A man who loved women, and a woman who loved men...

It wasn't exactly a one night stand – we met again a few months later for a rematch, which was just as spectacular – but we weren't exactly lovers either. That came later, when I finally met my soulmate, an older man who went to the same university as I did, who shares all my tastes in music and literature, and who delights in treating me like a lady. We've been going strong for several years now, and he's taught me that sex for an older man is not only possible, it can be very exciting and very gratifying if the woman is fun-loving and creative. He lives a few hours away, so we can't see each other that often, which makes it exciting to plan each rendezvous, and keeps things fresh between us. We've gone out many times, always starting with a delightful lunch or dinner, and a few glasses of excellent wine – he's quite the connoisseur - at an intimate restaurant. Afterwards, in my bedroom or hotel room, we've never failed to bring each other to mind-bending orgasms, every time. And thanks to him, I finally got that chance to go ballroom dancing in my little black dress and high heels, the most romantic night of my life...