With the right padding and paint. A crossdressing story

With the right padding and paint. A crossdressing story

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 I know that as I've gotten older 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, 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 old pantyhose that my mother had tossed in 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 already at that early age I 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 so long as 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, there 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 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 many 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 Jerry and 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 actually doing it. The thought of being able to 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, "With your looks 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 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 too and it was really an impulse buy. Some part of my brain must have told me I would need to carry things 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 the mid 80's 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 of the apartments 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 flat 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 up 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 a lot of 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 the right paint and padding 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?"

"Like I said," he replied while lighting a cigarette, "with the right padding and paint it's amazing what we'll be able to accomplish."

It was still early in the afternoon, so we sat and chatted about a range of things. Jerry talked about some of the bars he liked in Chicago. Arnold told me about the drag shows he performed in. He talked about groups or families and theatrical presentations and performances that he and his counterparts would do. At one point he pulled out a photo album and showed me some Polaroid pictures of himself in drag. He looked amazing. In the album were photos of other crossdressers and performers and he told me a bit about each of them and how they had come to be part of "the scene". At one point I asked him why he was helping me. His reply was a simple statement, "We have to help each other. It's part of how we work as a family. The world isn't nice to those of us who don't conform so we help each other."

Eventually, Arnold looked at his watch and told us it was time to start the process. I felt a thrill of excitement run through me and I asked him what I should do. I was instructed to go into the bathroom, take a hot shower, and shave everything south of my eyebrows. I told them that I had shaved my legs before but not "everything". Arnold and Jerry both offered to help me. I was a bit nervous about this -- but I figured that it was worth the awkwardness, so I consented.

The shaving process was surprisingly easy with help. After a long hot shower, I lathered up and shaved what I had easy access to. Jerry and Arnold helped shaving the back of my legs, my back, and some of the more difficult to reach areas around my junk. I noticed that Jerry kept staring at my cock which gave me a strange sort of thrill.

Once I was shaved clean, they helped dry me off and handed me a robe. The robe was black satin and felt wonderful against my freshly shaved body. I cinched it tight around my waist and looked to Arnold for what to do next. He brought me into the room with makeup and clothes and had me sit in the chair in the center of the room. The lights on the mirrors had all be turned on and I sat facing one so I could watch Arnold work. He spun the chair so I couldn't see the mirror. When I asked why he explained that he wanted to "blow my mind" with the first look of myself as a woman. Jerry then went about the room covering all the mirrors with towels and clothes so I wouldn't be able to peek.

"First we'll start with your hair." Arnold announced. While I had slightly longer hair, I didn't think it would be long enough. When I voiced this concern Arnold replied, "Don't worry, I have a few extensions that we can use." He continued to work on my hair pulling it up and back away from my face while applying a generous amount of gel and hair spray. Then he attached a hair extension that closely matched my own hair color giving me what I realized would be a long ponytail. I could feel it brush against my back through the thin satin robe.

Next, Arnold went to work on my face. He shaped my eyebrows giving them a slightly arched look. I recall that I started sneezing for some reason as he plucked stray hairs from the center and corners of the brows. Next, he started applying the makeup. Foundation and shading came first. As I sat in the chair letting him work his makeup magic on me, I remember feeling the need to cross my legs to sit in a more feminine posture. I could feel the air on my smooth and freshly shaved legs, and it was making me feel slightly aroused. I was glad that they had given me a robe to wear as I was sure the stirrings of an erection would have been very noticeable by everyone in the room had I not been covered. I notice Jerry looking at me again with a smile on his face. Again, I felt that strange thrill at his attention. Something about a man looking at me like that, looking at me with desire, made me feel excited.

As Arnold applied fake lashes and worked on my eye makeup, he asked me more about my interest in crossdressing. I talked again about how I had always been drawn to women's clothing, I told him about the photos in Penthouse of the beautiful and sexy women and how I had fantasized about looking like them. I told him about the stories I had read about men who had dressed up as women and how I dreamed of trying it. Arnold smiled and said it was a common story. He had met lots of young men who enjoyed crossdressing -- some were gay, some were not, some were something in between.

Next came eye makeup -- big, bold, and smoky like a Palmer girl, and finally a deep red lipstick. Arnold leaned back after applying the lipstick with a satisfied expression on his face. I asked to look in the mirror, but Arnold insisted that I wait till I was fully dressed for the "full mind fuck" as he called it.

From the table next to us Arnold pulled a box from a drawer. It was a box of Lee press on nails in deep red. After some effort, a bit of nail filing, and a couple of curse words, he had successfully given me a full set of red feminine nails. The color was close in shade to the lipstick Arnold had used on me.

I was told to stand up so they could take a look at me. As I stood, I straightened the robe and pulled it tight again. Arnold looked me over and announced that I was ready to be dressed. He told me to get my bag with the shoes and other things while he found a dress for me. I realized I had left the bag in my car and would have to go outside to get it. I looked at Jerry and asked if he would mind going to my car to get it. He just smiled and said, "You look great -- go ahead and get it yourself." With little choice I pulled the belt of the robe closer around myself, grabbed my keys, and headed toward the door.

I made a quick dash down the stairs of Arnold's apartment praying that I wouldn't run into anyone. The hall was empty, so I slipped down the stairs on my bare feet and opened the outside door. My car was parked about 50 feet from the door under a streetlight. As I walked to my car, I could feel the air on my smooth bare shaven legs and feel the ponytail bob at the back of my head. The robe was thin and I shivered slightly in the cool early October air. I reached the car, opened passenger side door, and grabbed the bag from the passenger seat. I almost dropped it because of the nails but managed to keep hold of it. When I closed the door, I caught a faint reflection of myself in the window under the streetlight. Looking back at me was a beautiful woman with dark hair, dark sexy eyes, and dark lips. It was like someone else was looking back at me. Arnold was right -- it was a total mind fuck. As I stood transfixed, staring at my reflection, I heard a sound from down the street. I looked and saw two guys walking down the sidewalk toward me.

Panic filled me. I was out on the street in a strange city wearing only a bathrobe and made up like a woman. I felt incredibly vulnerable, so I put my head down and started walking quickly back to Arnold's apartment. The timing was awkward -- the men walking toward me would reach the front on the apartment just as I approached the sidewalk leading up to the front door. As I passed, I didn't look at them, but as I turned toward the apartment entrance one of the men gave a low whistle and said, "Hello beautiful." I quickly opened the front door to the apartment building and went inside.

Once inside I closed the door and leaned back against it. My heart was racing from the excitement and, to be honest, stark terror of being outside dressed as a woman. But I was also thrilled that a strange man had just whistled and called me beautiful. I took a deep breath, hit the buzzer for Arnold's apartment, and climbed the stairs.

When I entered the apartment Jerry was in the main room looking out the front window. He said, "Looks like you made some friends." He had been watching to make sure I was ok. A sweet gesture and I let him know that I appreciated him looking out for me.

When I got back to the "salon" of the apartment I put the bag on the chair and started pulling things out. Arnold "tisked" at much of what I had brought with me, but we finally settled on a tight pair of black panties, black panty hose, and the black suede pumps with three and a half inch heels. He instructed me in the art of "tucking" as I pulled the panties on. Next came a waist cincher he pulled from a drawer. He wrapped it around my waist and fastened it to help narrow my already slim waistline. Pulling on the pantyhose with my new nails was a bit of a trick. With some instruction from Arnold, I managed to bunch the nylons so I could pull them onto my feet and roll them up my legs pulling them tightly up my waist. With the waist cincher I noticed that the top stayed in place better than it had before.

Then Arnold did something completely unexpected. He grabbed a jar of Vaseline and a roll of wide medical tape from a shelf and pulled a couple yard long strips from it. He told me to hold my arms straight up over my head. First, he rubbed a small dollop of Vaseline on each nipple. "You'll thank me for this later," he said. With his right hand he attached one end of the tape strip to the side of my chest and pulled it forward. With his left hand he pushed the other side of my chest toward his other hand and attached the tape across my nipples and to the other side of my chest. He repeated the process in reverse just under the first piece of tape. When he was done, he had created what looked like convincing cleavage with my rather flat chest. Arnold smiled and said, "A little drag queen trick I learned."

Next came the bra. It was black, lacy and had foam inserts. Arnold had not liked any of my bras so he gave me one of his. It was a C cup so not as big as what he used for his drag show persona.

The dress was next. A little black dress -- not exactly like a Palmer girl dress but close enough. It was clingy and short, coming well above the knee with long sleeves and cut low enough to show my fake cleavage. The bottom had a slight asymmetrical cut that showed off a nice expanse of my thigh. Around the waist of the dress was a flared ruffle that gave it an extra layer. Jerry explained that it was called a "peplum" style dress and would help give the illusion that my hips were larger. It fit like it was made for me.

After I put the dress on Arnold pursed his lips a bit and said, "Your shoulders are too wide. We need to disguise them with a jacket." He started looking through the racks of clothes in the room and gave an unhappy "huff" when he didn't find anything to his liking. I looked down at my bag sitting on the floor near the wall and said, "What about my jacket?" Jerry stepped over to it and held it up to examine it. It was a classic black leather biker jacket with a few punk style pins and buttons attached (it was the 80's after all -- we wore stuff like that back then). He pursed his lips and said, "It's not perfect, but it will do." Once I put the jacket on Arnold told me to slip into my heels and we would see how I liked my new look. As a final touch he added some bangle bracelets, shiny necklace, dangling clip-on earrings, and a few costume jewelry rings.

Jerry removed the towels and clothes that covered the full-length mirror in the room and I heard myself gasp in amazement. It was surreal -- like something out of an episode of the Twilight Zone. Here I was, standing in front of a mirror, and the person looking back at me wasn't me. The person I saw standing in the mirror was a gorgeous young woman. She had darkish brown hair pulled back into a long ponytail. Her eyes glittered blue under long full lashes and dark smokey makeup. She was tall and slender. The peplum dress, cincher and bra gave her enough curve to make her look feminine and sexy. Her shapely smooth legs were covered in dark shiny nylons. The cut of the dress gave a tantalizing flash of her thigh. On her feet were sexy black suede pumps. The black leather jacket gave her a slightly "bad girl" look. Her deep red lips were open in a look of astonishment.

"Oh...my..." I heard myself say. The young woman in the mirror's lips move in sync with my own. I moved my hand and saw the woman raise her hand allowing her red nails to caress the curve of her stomach and up along her breasts. It was dreamlike.

"What do you think?" asked Arnold.

II was speechless for a moment. "I never in my wildest dreams imagined that I could look so... so... so good!" I replied in a breathy whisper, my eyes never leaving the image of the woman in the mirror.

"Yeah, I gotta admit. I do good work," Arnold laughed. I could tell he was enjoying my stunned expression at the transformation. Jerry chimed in, "I think you're going to be very popular tonight."

I probably stood there for twenty minutes staring at myself in the mirror. I had tried dressing up many times, even tried some crude attempts at makeup over the years, but I was absolutely astonished at what I was seeing. As I stood transfixed in the mirror, I ran my hands along my body feeling the tight material of the dress. I shifted my stance a few times rubbing my legs together feeling the smooth nylon caress my shaved legs. The heels were comfortable enough and I had spent enough time practicing how to walk in them that it was no problem. And, as always, the heels made my legs look shapelier. I felt a flush of erotic energy every time I moved. A part of me wanted to pleasure myself while looking in the mirror. Talk about narcissism -- right? As Arnold had said, it was a total mind fuck.

Eventually I pulled my self away from the mirror and walked out into the main room of Arnold's apartment. He and Jerry had left me staring into the mirror with appreciative chuckles. I was conscious of the click of my heels on the hallway floor and found that I had adopted a "sway" to my walk, swinging my hips slightly as I moved. I found them sitting on the couch having a glass of wine. Jerry eyed me over his wineglass and said, "So what do you want to do now?"

"I want to go out," I replied in a rush. My fantasy was coming true. I could hardly believe it. The first part had happened, I looked like a gorgeous woman dressed in a tight sexy black dress and CFM shoes. Now I wanted to experience what it would be like to be out in the world like this,

"It's still a little early but we can find a place or two to hit," he replied as he excused himself to get cleaned up and change clothes. I looked at the clock and was surprised to see how late it was. The transformation process had taken longer than I thought. At least two and a half hours had passed.

I sat on the couch, crossing my legs, and looking down at my legs and heels. I couldn't stop staring at myself. The TV in the room was turned off so I could see a murky reflection of myself in the screen -- a tall, sexy woman sitting with her legs crossed. I looked over at Arnold and asked if he was coming with us? Would he be getting dressed up too? He replied that he was going to perform later that evening and Jerry and I could meet up with him then. He tossed me a lipstick and said I might need it later for a "touch up".

Jerry emerged later dressed in his club clothes. He held my bag and suggested we take it with us in the car because "You never know how the night will end." I pulled out the small black purse, put my wallet, keys, and lipstick in it, and we headed out the door.

As we exited the apartment Jerry said, "Let's take your car." As we walked the short distance, I reveled in the feelings I was experiencing. The cool October evening breeze caressed my nylon covered legs and I could feel it swirling slightly up my dress. My heels clicked on the sidewalk, and I let my hips continue their slight sway as I walked along.

When we reached the car, I started to move toward the driver side but Jerry stopped me and said, "The gentleman should drive." I paused for a second -- it made sense since he knew where we were going and I didn't. I smiled slightly, batted my long new eyelashes at him and handed over the keys. He then unlocked and opened the passenger side door for me. Getting into a car in a short dress was a new experience for me but I managed to slide in while keeping my legs together.

As Jerry drove into downtown Chicago, I was torn between looking around at the city -- the unfamiliar sights of the L-train, garish neon signs, and street life that was so different from the sleepy rural town I was from -- and the shimmery reflections in the car windows of myself en femme. I felt breathless at the prospect of living out my fantasy. Jerry and I chatted small talk as he drove, talking about work and everyday events. I kept looking down at my legs admiring how they looked in the strobing lights of the passing streetlights. Occasionally I would run my hand up and down my thigh seeing a caressing set of feminine fingers with long red nails. The sight and feeling was electric and I felt my tucked away cock twitch in reaction. I also noticed Jerry stealing glances at me as he drove.

While sitting at a stop light, I asked him, "Do you like how I look?" He took his eyes off the road, turned to me and said, "You looked good as a guy. You look amazing as a woman. Are you sure you're not attracted to men?" I smiled and replied, "Sorry my friend, but I'm only into women." Then I added hastily, "But maybe I might like another guy dressed as a woman." I surprised myself when I heard the words come out.

"Well, then I might have to ask Arnold to work his magic on me," Jerry laughingly replied. "Yes, but you'll need to shave the mustache," I said with a smile.

We parked the car on a side street a couple of blocks from the main street in what Jerry referred to as "Boys Town". As we walked, I was glad for Jerry's company. Growing up in a sleepy rural town made the big city of Chicago seem dark and dangerous. The night was getting cooler, but the leather jacket kept me comfortable as we moved toward the traffic, lights and noise. As we walked, I was hyper aware of every sensation -- the breeze on my legs, the tug on my ears from the dangly earrings, the feel of my nylon covered thighs occasionally touching as I walked in my heels. Once on the main street we continued down toward a bar that Jerry said he frequented often. I noticed a lot of people walking along going into and out of bars, restaurants, or shops. I was pleased to see more than a few men turn their heads to check me out. Or maybe they were checking out Jerry. It was Boys Town after all.

We entered the bar and found it to be half full. Back then nobody checked IDs so there was no problem with me only being 19. Besides, in Wisconsin the legal drinking age at that time was 18 so I had been going to bars for a while. We headed toward the bar and took seats on a couple of available stools. I crossed my legs and angled myself so that they pointed away from the bar. When the bartender approached, Jerry greeted him warmly and order us drinks -- a beer for Jerry and a Boone's Farm Strawberry Hill for me (my taste in liquor has become more sophisticated since then). I tried to minimize the amount of talking I was doing since my voice was far from feminine. Basically, I was content to let Jerry do the talking so I could just soak in the experience.

As we chatted Jerry pointed out a few of his friends and introduced me to some. One asked my name and I was unsure of how to respond. As I stammered a bit Jerry told his friend that it was my first time "out" so I might not have picked a name. His friend seemed to understand, and we moved on to other conversation. While we talked, I mulled over what name I should choose. I hadn't really thought about it. I couldn't use my male name. As I thought about it I remembered a girl I had a crush on when I was younger. She was tall, beautiful, with dark brown hair she often wore in a ponytail. We had flirted a bit, but nothing came of it. Her name had been Jenette.

"Jenette!" I blurted out to Jerry when there was a break in the conversation, "That's my name, Jenette." Jerry smiled and said it was a great name.

As the night wore on, we drank more and talked with Jerry's friends. There seemed to be an endless stream of them. Some of them were clearly interested in him but more than a few were flirty with me. One of them, his name was "Tom", sat next to me at the bar and started chatting with me. As we talked, he put his hand on my thigh and started slowly rubbing up and down. Surprisingly, I let him do it. A couple of times his hand strayed pretty high up on my thigh -- if I hadn't been wearing pantyhose and panties he might have gotten a hand full. While he did this he kept looking into my eyes, slowly stroking my leg, leaning into me as he talked. I realized that he wanted me. I smiled inwardly knowing that he was going to be disappointed but enjoyed playing the part as he tried to seduce me. I kept my legs crossed to keep him from exploring too far.

The crowd in the bar started to grow. It was a mix of mostly men, some women, and I spotted a few other crossdressers in the crowd. Most looked pretty good. A few, not so much. But all seemed to be having a good time chatting and listing to the music. As I scanned the crowd letting my new paramour keep his hand on my thigh, I heard Jerry say, "Jenette, I want to introduce you to Angie." Spinning on my bar stool I saw a gorgeous woman with dark curly hair and deep brown smiling eyes. She was maybe in her late 20's or early 30's, average height, and dressed in a short black leather miniskirt, black hose, black heels similar to mine, and an animal print blouse with big puffy shoulders that was the style back then. She wore little makeup -- but she didn't need it as her face was beautiful with high cheekbones and full lips. She leaned into me and gave me a big hug saying, "Jerry just told me it's your first time out. That's so great! You look gorgeous!"

I think I blushed a bit and echoed Arnold's words in response, "It's amazing what you can accomplish with the right paint and padding." Then I thanked her profusely compliment and told her that I thought she was gorgeous too.

She moved a couple of steps closer to me, turned to the guy sitting next to me who still had his hand on my leg and said to him, "Hey Tom, why don't you let me talk with Jenette for a while. You know, girl talk." With a slightly crestfallen look Tom obliged and offered Angie the seat next to me. As she sat on the stool, I pulled my dress back down to a more respectable level since "Tom" had been slowly sliding it up during his unabashed groping. "Thanks for the rescue," I said.

Once she was settled, she flagged down the bartender, ordered another drink and said, "Don't worry about Tom. He likes crossdressers, and you are one off the prettiest ones I've seen in here." She took a sip of her drink and then asked, "How do you like it?" I must have had a confused look on my face since she added, "Dressing up? Jerry said that this is your first time going out like this. How do you like it?"

I nodded in understanding. Since I was becoming more comfortable discussing what until that evening had been a taboo subject I replied, "I really like it. I've never felt so excited. It's hard to explain..." Then I looked her over quickly and asked, "Are you...?"

"Me?" she replied with a laugh, "No, I'm a real girl."

"Oh," I said with what might have sounded like a bit of disappointment in my voice. "But I thought this place was just for...um...gay people or others like me."

"Exactly," she said with a laugh, "I like girls... and sometimes I like guys. I guess I'm complicated." She laughed again and held up her drink for us to toast.

Angie and I continued to chat like two old girlfriends. I learned that she was older than me by a decade, was divorced from an Italian guy, and had recently embraced her desire to be with other women. She asked if I had done my own makeup and I told her about Arnold/Annie. She nodded knowingly and said, "I know Arnold and his alter ego. I've seen some other guys he's worked on and he's a real artist!"

As we sat on the bar stools talking her nylon covered legs kept brushing against mine. Each time it happened the feeling was electric. We leaned close to each other to hear over the music in the bar and from time-to-time Angie would touch my arm or my leg while we talked. I took my cue from her and started to reciprocate -- lightly touching her arm or leg, pausing briefly on her silky nylon covered thigh and sometimes lightly running my nails along her leg when I pulled my hand away. I was beginning to think, despite the age difference, there was some real chemistry between us.

Angie finished her second drink and said, "I need to use the ladies room. Come on Jenette." I hesitated. I needed to go myself, but I hadn't considered the issue of which rest room to use. A brief mental image of standing at a urinal in my heels with my dress pulled up to pee flashed through my mind. It was amusing, but I didn't think that would be the most appropriate way to handle the situation. Angie saw my hesitation and said, "It's OK. Nobody here cares what restroom you use. It'll be fine so come on." With that she grabbed my hand and we headed off to the restroom.

I'd never been in a women's restroom before. It was large, clean, with five enclosed stalls along one wall and a large mirror with five sinks along the other wall. Two other crossdressers were at the sinks doing a line of coke and fixing their makeup. Angie, still holding my hand, led me toward one of the open stalls and said, "I'll be right next door." With that she entered the larger stall next to the wall -- it was obviously a handicap stall and twice the size of the others.

I entered the stall next to me, pulled up my dress and pulled my panties and pantyhose down to my knees. Then, with a sense of great relief, I untucked myself and sat down to pee. I hadn't realized how badly I had needed to go. I guess the four Boone's Farm drinks had snuck up on me. As I sat there, I looked down at my legs, knees together with panties and pantyhose bunched around them. Glancing to the side I could just make out Angie's heels under the stall wall. She asked, "You OK in there?" I told her I was, finished my business, and then stood up to make myself presentable re-tucking and pulling my panties and pantyhose back into place.

I smoothed down my dress and exited the stall. The other "girls" had left the restroom and Angie and I had the place to ourselves for the moment. As I stood there, I saw myself again in the big mirror on the wall. I was still mesmerized by the sight. It was still surreal to see myself as a beautiful woman in a tight dress and heels, makeup still good. The long ponytail had flipped so it hung over my shoulder. In the mirror I saw the other stall door swing open and Angie walked up beside me. She checked her makeup in the mirror, turned to me, and much to my shock and amazement she kissed me.

The kiss lasted for a couple second. Her lips were warm and soft. I could feel our lipstick mingling slightly. She pulled back, looked me in the eyes, and kissed me again. Our second kiss was more passionate, and our tongues found each other. I felt her hands start to roam over my body and I responded in kind. Then, she broke our embrace, looked around the restroom quickly, and then pulled me into the large stall she had just exited.

We continued to kiss, standing in the stall exploring each other's bodies in a heated embrace. At one point I paused to take off my jacket and hang it along with my purse on the hook in the stall. We kissed again and I felt Angie's hand pull my dress up and start pull my pantyhose and panties down. My cock sprang out of its silky prison and she bent at the knees to take me into her mouth. I groaned with pleasure and held onto the top of the stall wall as she worked my prick with her mouth and hand. I had been aroused for a long time. The sensuous clothes, the erotic power of looking like a beautiful woman and having men flirt with me and touch me had gotten me worked up and filled with a need for release. I knew I wouldn't last long.

I stopped her by holding her head. I took her hand and pulled up to indicate that she should stand. Once she was standing, I pulled her skirt up around her waist to find that she wore only pantyhose with no panties. She understood what I wanted and reached down to rip a hole in the crotch of her pantyhose. She pushed me down onto the toilet seat and straddled my rigid cock taking a moment to guide me in with her hand. The sensation when she lowered herself onto me was one of the best of my life. She was warm and wet and tight. She moaned slightly as I penetrated her. She pushed me back to lean against the wall and put her hands onto my shoulders. Then she began to ride me slowly. We stared into each other's eyes, grinding away, our nylon covered legs rubbing against each other. I reached up to grab her breasts through her blouse and bra and I could feel her nipples were hard. She must have been as excited as I was because I saw her bite her lip and her eyes became unfocused. It didn't take long until she shuddered slightly as an orgasm rolled through her. That was the point of no return for me. I had tried to hold back my orgasm. I wanted this to continue and to savor it, but the events of the evening had built up to where I couldn't hold back anymore. I clutched her tightly, digging my fingers into her back and almost breaking off my fake nails as I came hard. I gasped loudly and my cock pulsed several times as I shot my load into her tight wet snatch. My orgasm was so intense all I could do was sit there with my cock softening inside her. Once I started to regain my senses, I could feel my cum and her juices dripping down onto my thighs. Angie leaned back with a satisfied smile and said, "I needed that. Thanks." I thanked her in return as we disentangled ourselves and stood up.

Before we exited the stall, I tried to arrange my clothing into a less scandalous appearance. As I pulled up my panties and pantyhose, I noticed that I had a rather noticeable run in my nylons. Angie grabbed a wad of toilet paper, cleaned herself up from my still dripping load, and pulled her skirt down. She smiled and said, "This is why I like leather skirts. No cum stains."

I grabbed my jacket and purse, and we exited the stall. There were two women in the restroom now who looked at us knowingly. They had probably heard our short but intense carnal encounter. I looked in the mirror again and noticed that my lipstick was a mess. It looked like much of it had ended up on Angie's face. She cleaned herself off with some water and paper towels and then helped me to reapply the lipstick Arnold had given me. Once we were finished adjusting ourselves, we both paused and looked at each other with sheepish grins. Then we exited the restroom and headed back to the bar.

As we approached the bar Jerry gave us a knowing look and a wolfish smile. "You ladies have fun?" he asked. I may have blushed a bit and Angie replied, "I really like your friend Jerry."

I think I was in a bit of a daze after that. Here I was, wearing a dress and heels, in full makeup, out in a bar, and I had just fucked a gorgeous stranger in a bathroom stall. I felt like I was living one of those stories I had read in Penthouse Letters. The whole thing had my head swimming. Eventually another bar stool opened and I sat down again, careful to keep my legs together and crossed, partially for modesty and partially to keep people from seeing the cum stains on my upper thighs. Jerry bought me another drink and we continued conversing with the people that came and went around the bar. Jerry seemed to know a lot of people and he was a very good host as he kept introducing me as "Jenette" to them. I just soaked it all in and enjoyed the feelings and sensations.

About an hour later Jerry leaned over and said, "I'm feeling a bit tired. Mind if we get out of here?" A part of me didn't want the night to end. But, like Cinderella, I knew I had to leave the eventually, so I nodded in agreement.

As we moved to the exit we made our goodbyes, hugging and kissing many people that I had briefly met that night. Tom was still there, as he gave me a goodbye hug his hand slipped down my back and grabbed my ass. I let him do it since he wasn't going to get any action from me. I looked for Angie, but she was nowhere to be seen. When I asked Jerry about her, he said he had seen her leave with another group. Needless to say, I was disappointed. I had hoped to get her number and maybe see where things might lead.

As we walked back to the car Jerry put his arm around me and pulled me in close. I think I might have been staggering slightly from the alcohol and my steps were bit wobbly. We walked along the sidewalk, his arm around my waist and his hand on my hip. I sensed that he might be trying to make a move on me. It was flattering, but I still wasn't interested in guys.

When we got to the car, he held the passenger door open again for me. I was grateful for the chivalrous treatment and smiled at him as I lowered myself into the seat. When Jerry got into the driver seat, he paused to look me in the eyes. Then, he leaned forward to kiss me. When I leaned back, he looked disappointed and hurt. "So, you really aren't into guys, are you." He stated flatly, "I was hoping that you might have changed your mind."

I felt a little guilty. Jerry had been wonderful to me. He had always been good to me at work giving me extra shifts. He had taken me under his wing, introduced to his friends, introduced me to a new and amazing world, had been my guardian and protector, and had enabled a long-held fantasy to come to life. I chewed my lip a bit, probably getting lipstick on my teeth, and looked at him. I noticed a distinctive bulge in his pants. He must have become aroused when we were walking to the car with his arm around me. I realized that as we walked my hip must have been rubbing against his crotch.

I guess the alcohol had lowered my inhibitions because I looked him in the eyes again and said, "I haven't' changed my mind, but maybe there's something I can do to thank you for everything you have done for me tonight."

I shifted position on the passenger seat so that I was kneeling with my legs under me. I leaned over the center console of the car, moved my hand to his belt and started to undo it. With a few deft moves I had the buckle undone and his pants unzipped. As I rooted around in his underwear, I found his hard cock and pulled it free. Jerry looked surprised but said nothing as I started to give him a hand job.

I'd never held another man's cock. Jerry's was longer and thicker than mine. I grasped it lightly and started to do a slow stoke up and down, making sure to use the pad of my thumb to rub the head on each pass. "Recline your seat and lean back," I told him in a husky voice.

I liked the way my slender fingers with dark red nails looked as they worked his cock. Jerry leaned back in the car seat and let me stroke him. I saw our reflection in the rapidly steaming car window. In the refection, I saw a beautiful and slender young woman in a black dress stroking the cock of a man in a car seat. The sight was arousing, and I felt my own cock starting to get hard again. My thoughts strayed to the possibility of maybe letting Jerry fuck me. I was dressed for it and I'm sure he would have gladly obliged me. It's not like I hadn't wondered what it might be like before. Some of the stories in the magazines I had read talked about men dressed as women having anal sex. I wondered what it might be like. The thought of getting down onto my hands and knees, having Jerry get behind me, ripping open my pantyhose, pushing my panties aside and letting him shove his cock into me was an exhilarating one. Still, that was a bit too "advanced" for me -- maybe another time...?

Jerry's groan brought me back to the moment as I kept working his shaft. A spot of precum had appeared on the tip of his prick and I picked up the pace a bit. We locked gazes as I worked his shaft. I could tell he was getting close. I leaned in closer to him and whispered, letting my lips gently touch his ear, "I want you to cum for me." Then I ran my tongue along his ear.

That was the tipping point for him. Jerry grabbed the sides of the car seat, stiffened, and shot his load. Two streams of cum shot up and away from his throbbing cock. Some of his cum landed on the front of my dress but the rest oozed over my hand. Still kneeling over him, I released his cock and leaned back with a satisfied smile on my face.

Jerry was breathing hard, but he recovered and looked over at me. I was truly into my role now as a slightly slutty woman, so I stared into his eyes, slowly raised my hand up and stuck a cum covered finger into my mouth. As Jerry watched I rolled the finger around in my mouth sucking it clean. Jerry just looked at me like he'd never seen me before and said, "Damn, you're good. Thanks, I needed that."

I re-positioned myself in the passenger seat so I was facing forward and said, "You're the second person tonight who has said that to me."

We drove back to Arnold's apartment with little conversation. I looked out the window, still catching reflections of myself but also seeing the strange world of the big city go by. When we arrived, Arnold wasn't home. Those were the days before cell phones so there was no way to reach him. Jerry asked me what I wanted to do. I think he was still hoping for a chance to fuck me. I admitted that I was getting a bit tired and should probably head home. It was still a 90-minute drive. The sun would be up in a couple hours. Jerry asked me if I wanted help changing my clothes back to male mode. For some reason I was reluctant to go back to those clothes so I told him I would just drive like this and would give the dress and other items Arnold had lent me to him to return later.

Standing outside my car, Jerry handed me the keys and gave me a hug. He tried to kiss me again, but I deflected and his kiss landed on my cheek. "I'll see you at work," he said as I got into the driver seat.

"Will it be awkward?" I asked.

"No," he replied, "We'll keep what happens in Chicago our secret." I smiled, waved, and started the drive home.

Driving in heels was a new experience. I could have taken the shoes off, but I wanted to keep the experience going as long as I could. As I drove north on the interstate, I noticed that I needed gas. This was back in the days before credit card pumps so I would have to go into the station and pay cash. Luckily, the interstate in Illinois had things called "the Oasis" with 24-hour gas stations. I pulled off the highway and up to the pumps. Before this evening I would have been too afraid to go in dressed as a woman. But after the events of the night, along with the fact that I was exhausted, I just sauntered into the station, up to the counter, and told the attendant, "Twenty dollars on pump three please."

The kid behind the counter looked at me but I couldn't decipher what he was thinking. I realized I must look like some bar slut who just got rode hard and was heading home. My makeup was smeared and my hair was starting to become a mess. I had a huge run in my black shiny nylons and I had a noticeable semen stain on the front of my black dress. Not too difficult to guess what I had been doing that night.

I walked back out to the car and began to fill up the tank. While I pumped the gas, I leaned back against the fender and enjoyed the night breeze against my nylon covered legs. There was another car getting gas and the guy was trying to sneak furtive glances at me. I wanted to shout, "Take a picture, it'll last longer!" I wondered if the guy might fantasize about me when he masturbated like I did to the pictures I saw in Penthouse.

I reached my apartment about half an hour before sunrise. When I got inside, I didn't even bother to get undressed. I just kicked off my heels, pulled off the jewelry, and passed out on the bed.

It was early afternoon when I woke up. Slanted rays of autumn sunshine streamed in through the window as I opened my makeup crusted eyes. I was still in my dress and hose. I loved the feeling. As I lay there thinking about the events from the evening before. I sat up and swung my legs off the bed to sit on the edge. The aftereffects of a minor hangover made my head swim a bit and my chest was a bit raw from the cleavage creating tape. I felt drained but happy from the intense roller-coaster of emotions and sensations from the night before.

I looked at my reflection in the full-length mirror on the bedroom wall. The reflection looking back at me was disheveled and rumpled. It showed a tired but pretty young woman. Her makeup was smeared, her mascara had run, her lipstick was smudged. Hair hung in disheveled stray strands around her face and her ponytail hung limply over her shoulder. Her black dress, wrinkled and stained, had ridden up to the top of her thighs. Her black pantyhose had a very noticeable run from the top of her thigh down to her ankle. In short, my reflection looked like a young woman who had been thoroughly and completely fucked the night before. The thought made me smile. Arnold had been right. It was amazing what you could accomplish with a little paint and padding.

As I stared at my reflection in the soft afternoon light I could hardly believe it had all happened. It was dreamlike -- just like one of the letters I had read in Penthouse -- but it had happened to me. As I thought about the events from the night before it didn't take long to become aroused again. Looking down at my still smooth legs covered in shiny pantyhose I laid back down on the bed, pulled up my dress, pulled down my panties, and masturbated to an intense orgasm. Then I drifted off to sleep again.

When I woke up an hour later, I decided it was time to get cleaned up. I could still smell Angie's cum, my hand still had some of Jerry's spunk on it, and my own cum had dried and stuck the sheets to me. I got out of bed, peeled off my clothes, pulled the ponytail extension from my hair, and took a very long and hot shower to scrub away the makeup other reminders of my amazing evening.

When I saw Jerry at work later in the week, he was totally cool and acted as if nothing had happened. The only thing he mentioned was that Arnold had told him I could keep the dress and other stuff as a "coming out" gift. It was probably a good idea since I hadn't been able to get all the stains out of the dress. After that, things went back to their mostly normal routine. I asked Jerry if he had Angie's number. He said he didn't but would ask her next time he saw her. I never got it as Jerry got transferred to a store in Florida a couple weeks later.

Over the next few months, I thought often of that evening. Without Jerry around I didn't know how to contact Arnold or Angie or anyone else I had met that evening. There was no internet, Facebook, Twitter, or any other way of finding people so common today. I didn't even know how to get back to the bar we had been at. I guess I should have paid closer attention, but I was so caught up in experiencing the sensations of the evening that I wasn't paying attention to my surroundings. I lost track of Jerry. He had said he would get in touch once he settled in Florida, but I never heard from him again.

As fate would have it, I met a girl shortly after my big adventure. She was a couple years younger than me, pretty with a voluptuous figure and blonde hair. I learned quickly that she was not the accepting type and my alternative wardrobe interests would not be popular with her. So, like many young men who like to crossdress, I buried my feelings, purged my closet, and married the girl. Seven years later we got divorced. Over time I went back to school to earn a few degrees, put together a highly public and successful career that has allowed me to travel across the globe, met and dated a lot of wonderful women, and had many adventures. During those years I would dabble in crossdressing from time to time, usually on Halloween when it was easier to explain. Some of the women I dated were OK with my interests. Most were not.

Eventually, about 20 years after my first time out, I embraced my interest in an alternative wardrobe more fully. I was single with no attachments and my career had shifted allowing me more free time and money. I had moved back to the Chicago area, and I started dressing more regularly, going out, and having a wonderful time. I joined the ranks of Jamie Austin's angels and learned how to do my own makeup. I started to be more experimental. I was busy with work but when time permitted, I would sometimes meet up with men, women, or transgender interested in spending time with an attractive crossdresser. I even had an offer to work as a CD escort! While flattering, I politely declined the offer of employment.

My first time out was a wild and amazingly fun event in my life. A night I will always remember, and the memory never fails to bring a smile to my face. I wish I had some pictures of that night, but we didn't have "selfies" back then.

I sometimes wonder what happened to the people I met that evening. I wish I could find a way to thank them -- Arnold, Angie, and Jerry. They helped me to realize a life changing fantasy and I would thank them with deep gratitude for accepting me and showing me a different way of living. I hope they are all well and have had lives as wonderful and fulfilling as mine.