It’s been a long time since I penned a memory from my adventures in crossdressing. I’m older now. And, as I’ve gotten older, my time spent in heels, hose, and skirts has become less and less. I’m not sure why — perhaps it’s a diminished sex drive — or maybe as I’ve aged, I know that I’m no longer as attractive as I once was. As a result, I don’t really dress up or go out anymore and every so often I find myself missing the thrill of it all. I’m not complaining — not by any stretch! I have a wonderful life now with a sexy and sweet young wife who I met during one of my international travels. I find that I am a very lucky man to have such a gorgeous, intelligent, and kind woman in my life.
But I’ve been feeling a need to share more of my stories.
I’ve been drawn to crossdressing for as long as I can remember. My older sister sometimes reminds me of how I would get into her dresses and shoes to play “dress up” when I was very young. I’ve always been an adventurous sort of person and open to new experiences. I’ve also been lucky to have been blessed as a man with moderate good looks that allowed me, with the right preparation, to pass as an attractive woman. So, I thought it might be fun to recount my very first time going out while wearing a dress and heels. I was young, life was full of wonder and excitement, and I discovered that I was not alone in my desire to wear a dress and heels. Writing this story was a lot of fun for me. Looking back on that evening from so long ago I realized what an amazing experience it was. As I stared writing, a lot of forgotten details and memories resurfaced from my life back then. People, places, the things I did, old technologies and a vanished way of life now forgotten in our digital age. Much of it had been lost through the haze of time and experience. It was fun to remember and mentally relive my first time going out in a dress and heels. I hope you enjoy reading it as much as I did writing it.
Ah, the heady days of the mid-1980s! The year was 1986. The Soviet Union was still the evil empire. The shuttle Challenger exploded on launch. Halley’s comet swung by earth. Mad Cow disease was in the news. Top Gun, Crocodile Dundee and Ferris Bueller’s Day Off were big in the theater while Marvel’s first movie, Howard the Duck, bombed at the box office. Max Headroom was a thing. You could by an Apple Macintosh Plus (with an entire 1 MB of RAM) for the wallet crushing price of $2600. NBC dominated TV with The Cosby Show, Family Ties, Cheers, Murder She Wrote, and The Golden Girls. And on MTV (because they actually played music videos back then) we heard and saw the amazing music of Peter Gabriel’s Sledgehammer, Madonna’s Papa Don’t Preach, Kenny Loggins Danger Zone, and Robert Palmer’s Addicted to Love.
I was 19 and had recently graduated from a small rural high school in southern Wisconsin. It was a quiet and conservative town along the border with Illinois and I had absolutely no clue what I was going to do with my life. College didn’t appear to be an option at that time as my grades were more closely aligned to the lower achievement levels (I would later change that and go on and get advanced degrees). Thanks to “Reaganomics” good paying jobs were scarce in my hometown and the country was slumping along at close to recession levels.
I was average in most ways. Tall with a light complexion, mousy brown hair down to just above my collar and bright blue eyes. I was thin but not muscular as I never engaged in sports or any sort of regular exercise. I was also average in that I was quite naïve to the ways of the world as most young men are at that age. There was no internet, social media, chat rooms, Wikipedia, or news on demand. To learn about things, we had to go to the library or ask someone. But growing up in a small rural and conservative town with conservative parents I knew that there were some subjects you couldn’t go to the library or ask someone about. For example, you couldn’t learn about sex that way. As with most typical young men, sex was much on my mind. I liked it, I wanted to have more, and I wanted to learn more about it.
To learn about sex, I had to turn to my older brother’s hidden stash of Penthouse Magazines. He had “gifted” them to me when he moved out of the house. Within those colorful pages I saw images and read stories that gave me a wider view on the world and the possible wonders of sex.
I wasn’t a virgin. I had lost that the year before with a pretty girl named Susan who took an interest in me. She was a bit older than I and more experienced. She showed me the joy of intercourse and oral sex. We dated for a couple months and pretty much every weekend we spent countless hours having sex until we were exhausted and sore. But soon she went off to college and I was left once again with my brother’s old stash of Penthouse magazines to satisfy my endless interest in sex and women.
Of particular interest in those magazines was the section called “Letters”. In the columns of those steamy confessions, erzurum escort I read of things I barely dreamed could be true. Anonymous sex with strangers, anal sex, hand jobs, gay sex, sex at work, and the ubiquitous “I never believed it could happen to me” stories of college cheerleaders spreading wide for the newly arrived freshman on campus. Of course, I also enjoyed looking at the photos of nude or scantily clad women in alluring poses. There were plenty of sweaty sticky nights spent ogling the images of those erotic goddesses while fantasizing about what it would be like to be with a woman as sexy as the one on the page. But unlike most young men, some of my fantasies involved musings on what it might be like to look like those women on the magazine pages. I found myself fantasizing about what it would feel like to wear their lingerie, stockings, and heels.
Occasionally, in the letters section I would come across a story about some guy who would be lucky enough to get dressed up as a woman and engage in some form of carnal activity. For me, those were the best stories. I devoured the stories that described what it was like to crossdress — to wear dresses, heels, panties, and bras — and to have mind bending sex while dressed as a woman.
I had been attracted to women’s clothing since I was very young. I don’t know why but the attraction was always there. I remember as a pre-teen in middle school fantasizing about what it might be like to show up at school in a dress. At that age the girls were just beginning to wear skirts and pantyhose and low heels, and I was always fascinated by the thought of what it might be like to dress like that. I wanted to know what it felt like to wear nylons and silky panties. One night I pulled a pair of my mother’s old pantyhose out of the trash out to try them on. I snuck the stockings into my room and rolled them up my legs savoring the feeling and look. But at that early age I already knew that such actions were not “normal” and would not be accepted by my friends and family. For Halloween I had suggested to my parents that I dress up as a girl. The idea was quickly quashed, and my parents suggested I dress up as something else. I felt ashamed and alone and kept my secret desires for crossdressing to myself.
Now I was older, 19, an adult, and out on my own. Jobs were scarce at the time, but I managed to land two part time positions. The first was at a local restaurant. The second was at a local shoe store. The first job was steady and, while the pay wasn’t good, I could keep myself fed with extra food the manager allowed me to take home. The latter job provided me with opportunities to quietly explore my interest in an alternative wardrobe by sneaking into the back room and trying on different high heeled shoes. There were many nights with few customers, and I was the sole staff member in the store. As a result, I could spend time trying on different heels and learning to walk in them. I was lucky that the store stocked a large section in women’s size 10 shoes as those seemed to fit me well. The store also sold pantyhose and stockings and when the occasional pair had a defective package, I could discreetly remove them from the damaged goods bin and take them home with me.
I liked working at the shoe store and liked the people who worked with me. The manager, a man named Jerry, seemed to like me too. He was in his 30’s, average height, somewhat stocky, with a full mustache that was popular back then. Jerry would often give me extra shifts to help keep the shelves stocked or take in deliveries. I noticed that he would pay special attention to me, conversing with me in the back room of the store or staying late after closing to talk while I closed the register and cleaned the store. Some of the other employees at the store told me Jerry was gay and that he was probably hitting on me. I laughed it off and told them I was only interested in girls and Jerry would just have to keep looking. I think even with my level of naiveté I had a sense that Jerry’s attention wasn’t just an older boss taking an interest in a young and eager worker. But I really didn’t care. If I kept getting the extra work shifts, I was willing to let him chat me up. It was kind of flattering in an odd sort of way.
My evenings were usually rather boring. Most of my friends had headed off to college. I wasn’t dating anyone. So, I spent a lot of time in my dreary one-bedroom apartment watching TV (we had four channels then) and paging through the girly magazines my brother had given me. Eventually I worked my way through all the Penthouse magazines in my collection, reading and re-reading the stories about crossdressing with fervid interest. While these stories were great, they were sparse in number, and I wanted more. Back in the mid 80’s, before the internet, there was only one other place where people could go to satiate their longings for erotic content that might fall outside the standard girly magazines. And that place was the esat escort local porn shop.
Like many small towns across the country, we had a diminutive adult bookstore. Ours was located a few miles outside of town just off the interstate highway. It was a rather seedy place, generally frequented by truckers, passing motorists, and the occasional local who hoped desperately not to be recognized. It could be an embarrassing experience to frequent the establishment. There was a risk of running into a friend or family member who would react awkwardly — sometimes stammering some lame excuse like, “my wife wanted me to get something” or, more often, an unvoiced agreement to ignore the other person and keep browsing the racks of skin mags and videos.
In this bookstore there was a small section of non-mainstream erotic content. It had a few racks containing BDSM, gay, and shemale magazines and videos. Off to the side of these racks was a single rack that contained books and magazines about crossdressing. Titles like Ladylike, Female Mimic International, Crossdressers Quarterly, and a small selection of crossdressing fiction books — usually written by Brits about boarding schools and forced feminization — were crammed into a single rack in the back of the shop. Through the pages of these periodicals, I found out that there were indeed other men who enjoyed donning a dress and heels. There were even “personals ads” of other crossdressers looking to meet people. One evening while I was at the store paging through the latest issue of FMI, I heard a familiar voice say, “Fancy meeting you here.”
I immediately flushed with embarrassment. I knew the voice. It belonged to my boss at the shoe store. I turned to find Jerry standing next to me. I tried to stammer out some excuse but before I could say anything he laughed good naturedly and said, “Don’t worry. Your secret is safe with me.” Then he glanced at the magazine I was holding and asked, “So, is that something you like or are you just browsing?” I started to stammer out a denial but some part of me wanted to share. Other employees at the shoe store had said Jerry was gay and I guess I thought that perhaps he would be more accepting and understanding of what many considered to be an aberrant desire.
“Yeah, I do. I like this stuff,” I admitted with a bit of chagrin, “It’s something I like to do.”
Jerry looked at me for a minute and then said, “Let’s get out of here and find someplace to talk.” I nodded, put the magazine back into the rack and followed him out the door.
We drove separate cars to a nearby bar. The bar was a typical small town watering hole with jukebox, dimly lit, with a bar along one wall and booths along the other. It was a weeknight and relatively early so there were not many people in the place. We took a booth toward the back and sat facing each other. After the waitress brought us a pitcher of beer Jerry leaned back against the booth and asked, “So, do you like men?”
“No!” I replied rather emphatically.
Jerry smiled again and said, “Don’t worry, I’m not trying to seduce you. Although the thought had crossed my mind.” He could tell I was feeling a bit uncomfortable, so he leaned forward and said, “I know that the staff thinks that I’m gay. They’ve heard me talk about going to the bars in Chicago. So, tell me, what do you like?”
I took a long drink of my beer, mustered my courage, and tried to explain to him that I was attracted to women, but I was also attracted to wearing women’s clothing. I stammered on about how I was excited by wearing dresses and stockings and heels. The idea of looking and feeling like a woman was erotic to me. I told him about my fantasies of dressing as a woman and going out in public. I even confessed to dressing up in my apartment and masturbating, which always gave me mind blowing orgasms.
After a brief pause Jerry told me he had friends in Chicago who were part of the gay scene. They performed in drag shows and ballroom events and knew how to transform from men into beautiful and passable women using makeup and padding. One of his friends, Arnold was his name, sometimes made extra cash by doing this. He called it a “transformation” service. Jerry offered to take me into the city, introduce me to his friends, and they might help me dress for a night out “en femme”.
I was stunned at the thought of doing it. The thought of being able to actually experience what I had only fantasized about was incredibly exciting, so I eagerly agreed. As we finished our beer, we made plans for when and where to meet in Chicago the following weekend. Jerry could tell I was beyond thrilled with this. As we walked out of the bar, he gave me a slow appraising look up and down. Then with a big grin he said, “I think my friend will be able to make it so you won’t recognize yourself in a mirror. I think you are going to have a really great time next weekend.”
The next weekend it was early October and I drove to Chicago to meet Jerry esenler escort and his friends. My car, a 1972 Gran Torino Sport (to this day it is still my favorite automobile), didn’t have air conditioning so I had the windows rolled down and enjoyed the breeze. The sun was out, the weather was perfect, and I was excited at the prospect of meeting some new people and maybe experiencing an evening going out while dressed as a woman.
I had a few things with me for the trip. A change of regular clothes including jeans, t-shirt, my black leather jacket, and toiletries. I’d also brought along a few items from my limited crossdressing wardrobe. I had a pair of black suede pumps with three and a half inch heels and a pair of high heeled black strappy sandals. I’d bought the shoes at the shoe store where I worked and had managed to try them on in the back room when there were no customers around. I had practiced walking in them and had become rather adept at it. I also had several pair of pantyhose also purchased from the shoe store. Along with the shoes and hose, I had several pair of panties and some ill-fitting bras I had nervously purchased from a department store. I had to guess sizes and, while the panties fit well, the bras were a bit too small. Finally, I had purchased a small black leather purse with a long shoulder strap. We sold those in the shoe store. It was really an impulse buy. Some part of my brain must have told me I would need it if I were to go out in a dress and heels for an evening. All this was stuffed into a gym bag and sitting on the passenger seat of the car as I motored along toward the city and what I hoped would be a grand adventure.
As I drove, I felt a sense of freedom that I had not expected. In my small home town any sort of non-traditional sexual interest was considered a “deviation” and relegated to the fringes of acceptable society. But Chicago was a big city. I didn’t know anyone there. The chance of running into someone that I knew was practically non-existent. I would be completely anonymous. As a result, I felt free to explore my crossdressing desires without fear of repercussion or embarrassment.
In a short time, I arrived at the address I had been given. Of course, back then there was no Google maps or navigation apps — I had to rely on a plain old paper map — but the place was easy to find. The building was a simple brownstone apartment complex on a quiet side street. It had six apartments spread over three floors with an entry vestibule with buzzers for each apartment in the building. After ringing the buzzer for the apartment number, I heard Jerry’s voice followed by a buzz to open the main door.
When I entered the apartment on the third floor, I was greeted by Jerry who quickly introduced me to his friend Arnold. Arnold was older — maybe in his late-30’s with a thin build and thinning brown hair. We all shook hands, and I took a moment to look around the apartment seeing it was tastefully decorated with bright colors. We sat on one of the two couches in the room and Arnold brought in a bottle of wine with some glasses.
We exchanged a bit of small talk with questions about the drive into the city and any difficulty in finding the apartment. Finally, Arnold asked, “So Jerry tells me you’re into the drag scene?”
I stammered a bit but finally said, “I… um… I like wearing dresses… he said you could help me look like a woman and we could go out to a bar.”
Arnold told me to stand up and he gave me an appraising look while tapping a long slender finger on his chin. “I think you have potential,” he said with a smile, “Come with me.”
Arnold stood up motioning for Jerry and me to follow. We walked through the main room of the apartment, down a short hall, and into a back bedroom. The room was cluttered with tables filled with makeup, a couple of large mirrors with lights, and racks of clothes. I immediately noticed lots of sequin covered gowns, feathery boas, stands with wigs, and two tables filled with makeup, brushes, and lots of other paraphernalia that I didn’t recognize. In the center of the room was a large swivel chair like the ones used in hair salons. A small color TV was in the corner playing MTV videos with the volume turned down low. On the walls of the room were posters advertising events at different bars. Some were of ballroom events. Others promoted drag shows. I noticed several of them highlighted a rather stunning looking woman named “Annie” as a performer. The woman on the posters was beautiful with flawless makeup, a big bust, skinny waist, and an over-the-top hairdo. Arnold noticed my stare and asked me if I liked his alter ego. “That’s you?” I said with a bit of disbelief in my voice.
“It’s amazing what a little padding and paint can accomplish,” he said with a smile. “Now, let’s see what we can do with you. Is there a particular look that you like?”
I thought about it for a moment, my mind flashing back to all those images I had drooled over in the pages of Penthouse. Nothing specific sprang to mind. After a pause I said, “I don’t want anything too over the top. I like women’s business suits or maybe a simple black dress.” Then I glanced at the TV where a Robert Palmer video was playing. “How about that? Can you make me look like a Robert Palmer girl?”