I was always curious about dressing as a woman, remembering when I was younger trying on my older sister’s clothes and getting so excited wearing pantyhose and heels, but the feeling past as I got older. I am about 5’10” and thin at 185 lbs. I always had very feminine features and with a good wig, I could easily pass as a woman (a few eyebrow plucks would help). I was in theater in high school, so I wasn’t afraid around make-up and wigs. I had worn my sister’s heels so that didn’t worry me either, a lap or two around the house and I would get the walk down. Some control top pantyhose would do the trick on hiding my male parts easily since I didn’t have large genitals.
I fantasized about dressing again and again even checking out a few online stores to purchase the right size heels, dresses, and wigs. My fantasies went on for quite a long time. After I got married, I kept my feminine side a hidden secret. But slowly, the urge began to grow bigger and bigger. I found myself wanting to dress up as a woman again. I got dressed a few times but it wasn’t any fun since I was not dressed fully from head to toe.
One day my wife, Debra told me that she would be going to Chicago for some business. She would be gone for a whole week. I tried to sound disappointed, but in the back of my head I knew that I was going to order the dresses, wigs and heels and become a woman for the week. She would leave on a Monday and return the next Monday. She had asked if I could take a few days off and come with her. I quickly made some story about one of my biggest clients would be in town that week, and it wouldn’t be wise to take off just then. She seemed disappointed, but never raised the question again.
I opened a new credit card under my name only and ordered some size 13 black heel pumps with 4 inch heels. I also got a couple pairs of control top pantyhose, black and white sheer stockings, two black knee length dresses, a blonde wig, and some jewelry. I also purchased some breast fillers and corset tops to wear as well. The corset would help with my upper body figure and the breast fillers would come in a size c, a cup size bigger than my wife.
I scheduled everything to arrive at the house the Monday Debra was leaving. I took some time off from work, telling them that I would be
going to Florida for some personal work. I told them to forward all my work calls to my cell phone. Even if Debra was going to call my office, she would still get a hold of me and wouldn’t arouse much suspicion.
It was setting up to be a perfect week being a woman. And when the weekend arrived before Debra’s trip, I couldn’t wait to do some light makeup shopping and settle in to silky, feminine clothes. I helped her pack and told her I took a half day to take her to the airport.
As I carried her bag through the terminal my mind was fantasizing about my heels and dresses. I kissed Debra passionately before she went through security and we promised to call each other when we had the chance.
As soon as she had left, I jumped back in the car and went to the makeup store and purchased makeup and some hair-removal wax to thin out my eyebrows and soften my beard growth. I spent the rest of the morning shaving my body. I really couldn’t believe that I was going all out for this fantasy.
After my shower, I couldn’t stop touching my smooth legs and underarms as I used whatever my wife left for lotion and perfume. Next were my eyebrows, which I took the wax and began to painfully shape my brow for a more girly look. I stepped back to look at my more girlish face. I almost didn’t recognize myself around my eyes, and I smiled broadly as I looked back at a more womanly me, and I had yet to apply any makeup. As I was feeling proud of myself, the door bell rang.
I ignored the weird look I got from the delivery man and tore into the package as soon as he left. I could hardly contain my excitement as I pulled out black heels and black dresses. First I pulled out the tan control top hose and slipped them on. The feeling of pantyhose sliding up my long smooth hairless legs was exhilarating. I tried my best to keep my hormones under control. Next I fitted the corset and wrapped it around my body. The breast inserts fit perfectly into the cups and I felt womanly as I moved it into place. As I looked down I couldn’t believe how my body was being transformed in to something so sexy.
Next was the blonde wig that was shoulder length, I fitted it on my head and moved it around. I didn’t spend much time styling the hair, which was a good thing. I don’t think I could spend the time doing it up. I stood back and looked at myself in the mirror. I felt my manhood start to get aroused.
I was barely able to recognize myself as I looked on. With a little sexy makeup I doubt I could be mistaken at all as a man in drag. I looked that good. I turned and rubbed my hands all over my flat stomach and legs. My hands shook a little as I began applying my makeup. A little rogue and some lipstick and eyeliner, I was beginning to become more and more of a woman. When I finished with make-up and tried not to dwell on my face and carefully slipped into one of my black dresses.
The dress fit like a glove, even around my bust and hips. My sister’s dresses never fit, and wearing Debra’s things was really out of the question, they would just be too tight and rip at the seams. I just never wore anything that was this womanly that fit me. It was black dress that was tight with spaghetti straps and was about knee length. It had a white lace trim at the top and on the hem. A small skinny belt went around the waist.
I pulled out some black sheer stockings I ordered and slipped them on over the tan hose. I sat on the bed and fixed the stockings to the garter straps on the corset. Catching myself in the mirror, I once again could not believe it was really me looking back. I stood in the full length mirror and. I would lean to show my cleavage, which was a pleasant surprise with the corset creating a natural looking cleavage.
To the passing eye, I was an athletic tall blonde haired woman with long beautiful legs and slight hour glass look to my body. I was so excited I could no longer hide my arousal through the pantyhose, a definite outline surfaced at my crotch. Trying to keep from getting aroused again I practiced on my walk and sitting up and down with a dress on.
I was surprised how easily I picked up sitting up straight as a girl and keeping my knees together as I stood up and sat down. I also worked on a feminine voice, which wasn’t hard for me in the first place. Many telemarketers would call me ma’am on the phone when I would answer. I practiced in the bathroom where the echo would help out, and then I called a few numbers to friends as a telemarketer to see if I could pass as a woman. It only took the first call as I tricked a friend of my wife’s. I even flirted a little with him, surprised how easy it was.
I was feeling pretty good about how I looked and how it felt. I finally worked up my courage and slipped out of the house after dark and took Debra’s car, a little convertible, and took a drive toward downtown. I packed one of my wife’s purses, and made sure I had everything a girl would have, even some tampons. I also slipped on a pair of black panties to go over the hose for added security that my little member wouldn’t make an appearance. I touched up my makeup and gave a final look in the full length mirror. I was surprised how womanly I looked. Finally I tied one of Debra’s scarves around my neck and adorned jewelry. My heart was in my throat as my heels clicked on the garage floor and I unlock the red convertible.
I had some difficulty getting in on the driver-side; it was very unlady-like. I moved the seat back and adjusted everything to accommodate my size. Then I practiced both getting in and exiting the small car. It took me about a half hour to get it down right, although, I could still be doing something wrong. I had to get my brain around moving and reacting as a woman would do. I just kept imagining I was a beautiful girl all my life. There is no need to act muscularly. Getting my heels to work with the pedals was also a challenge. Realizing that I was going to be as comfortable as I was going to get, I turned the ignition and slowly pulled out of the garage and pulled onto our street.
I wanted to get out of my neighborhood as fast as I could so as not to arouse suspicion with neighbors seeing a strange lady driving my wife’s car. I felt more and more comfortable driving in heels as I hit the interstate and headed for downtown. But where should I go? I was almost just content on driving around for my first night out as a woman. Stopped at a light a car pulled up beside me and I turned to look. The blood drained from my face as I realized it was one of Debra’s girlfriends. She rolled down the window to talk and I nervously looked around for the window button, what would I tell her?
Her name was Katie, a cute petite red head that was always the wild one of Debra’s friends. She had a tight body and breasts that were much bigger than her frame. She had always wanted to get a breast reduction, but I always thought that was a part of her attractiveness. She had amazing legs. I couldn’t keep my eyes off of them when she was around wearing skirts or shorts. In heels her legs looked even softer and more sensual. She was the last person I really wanted to see right now. As I lowered my window she screamed at me to pull over, I reluctantly did and both cars came to stop on an empty block. She slid out of her SUV and she was dressed as if on a date. Short white cocktail dress, tan nylons and white heel pumps. I felt a twinge of lust for her as she approached my little convertible.
“Hi, I am sorry but I know the people that own this car, and they are out of town,” she said, very direct, “I will call the cops, what are you doing with my friend’s car?”
“I am sorry,” I said as fem as I could, I figure I didn’t have to hide the fact that I was scared, because I was. “I… I work with Greg, and my car broke down,” I lied, trying to keep the story simple. “He told me his wife was out of town and I could borrow his car.”
“Oh,” she looked surprised, and she glanced down at my legs. “I have been to his work before, I don’t remember seeing you.”
Being as fem in my voice as I could, I turned it back on her, “I am sorry, I didn’t catch your name.”
“Oh sorry,” she said backing off a little, “my name is Katie.”
“Hi Katie, I’m Ginger,” I thought it sounded good. “I just started working with Greg. He is a great guy, very cute too.” Why not throw in a little ad for myself. I hardly believed it when I said it either. “He is out with some guys tonight but you can call him later and confirm with him.”
“Ok,” she smiled. “Well, I guess that is fine. To tell you the truth I have had sort of a rough night. If your new here, would you like to join me for a drink tonight.”
She must have seen a little fear in my eyes because she began to back off the offer telling me about a rough evening. I told her that I would be glad to grab a quick drink. I figured I needed it after that exchange, and after all, “Ginger” would have loved some company. I couldn’t believe really to what was going on. I thought for the most part that I had fooled her, but could I really be that stupid to accept to spend some time with a woman that could easily expose me? I felt sick to my stomach as I followed her to a quaint little bar that was not far from Katie’s house.
On the ride over, my cell phone began to ring. It was Katie calling confirm “Ginger’s” story. I answered it in the gruffest voice I had. Sure enough, she asked me about Ginger. At first I pretended not to know what she was talking about then suddenly remembered. I figured it added a tinge of realism. Once at the bar I concentrated on being a woman again. Watching how I got out of the car and remembering my purse and trying not to let the feel of hose on my legs turn me on.
She smiled as she stepped down off her SUV. I smiled back, more at the irony of me driving a little convertible and Katie in a large truck. She saw my height for the first time and I felt her eyes on me trying to find something wrong. I immediately felt self conscious as we walked in the smoky bar. With no real tables open we sat in a corner booth and Katie sat very close to me. At one point our nylon cased legs rubbed together, I quickly withdrew my leg and smiled at her, she did the same.
My mind raced as I knew I could not just order a beer. As the waitress approached our table I was almost in a panic as to what to order. The waitress looked to me and I grab the little drink menu at our table and told her to ask Katie first what she wanted. She ordered a dirty martini and I said the same. I hated martinis but it should fall into the character I was playing.
After ordering a strange silence fell between us. I feared maybe she knew or that she could sense something wasn’t right. I felt I better get her talking about her or it would be a nightmarish night.
As we talked, mostly about her, our drinks arrived and I felt more and more comfortable talking and with my legs crossed. I even picked up a cute little laugh. Katie seemed lost in her story about her failed date that evening and talked about her frustration with men. I would nod and shake my head at certain parts in her story, and tried to keep my mind on controlling my body as a woman.
My transformation was defiantly having an effect on me because the martini was actually very good, and I even enjoyed some of the looks from other men in the bar at Katie and me.
Something else was also happening as I sat sipping my martini and listening to Katie’s woes. I was extremely turned on. It was an extraordinary feeling. I felt horny, and fantasized about some nasty sex dressed, but I stayed limp and hidden.
My heart pounded and my head swirled as I started to feel a buzz from the strong drink, and sitting listening to Katie put my brain into a trance. I almost forgot about my inhibitions and felt as if I were meant to be in makeup, long hair, and heels. I kept my wrists limp and kept as loose and feminine as I could be. When our second round came, I was feeling more and more as a woman.
Then it happened. Half way through our second round a couple of large men found their way through the crowd and was staring at us. They seemed goofy and drunk and asked to sit with us for a little bit. Before I could call it a night, Katie welcomed them to our table and a rather burly man sat next to me. He smelled of cheap beer and body odor, I wrinkled my nose every time he leaned in to join the conversation. He had dark hair and a 5 o’clock shadow.
He was a little cute; I could see that women would not be turned off by his looks. Katie was not bothered by her man at all, in fact welcoming the little touches and closeness of him next to her.
Conversations turned into flirting on Katie’s side and soon they were in their own little world. The man next to me, Adam, was going to school at the local college and didn’t like all those small girls on campus. I tried not to show any interest in touching or feeling, but also I was not trying to act out of character as a woman in any way. It was my first true test. I sipped away at my martini and tried to feel comfortable.
Before I knew it, we were somewhere in our fourth round of martinis when my worst nightmare came true. Katie started making out with her boy and Adam’s hands were starting to touch my legs. I was starting to get nervous and horny as he began getting closer and touchier. Luckily my penis stayed limp. His hands were amazing, soft and firm, slipping up my dress. I pressed my legs together and crossed them so he would not find something out of whack, then submitted to his eyes.
I was returning his flirts, and I started loving the attention. Katie was really fooling around with the guy next to her while Adam couldn’t keep his hands off my legs. As long as he wasn’t going near my private area,I found myself welcoming his advances. The stench of beer and odor from him turned it to an intoxicating blend of bitter sexual appeal and horny bodies. I felt his arm around me, so strong, and I left a hand on his leg. I never considered myself a homosexual, guys are not my type. But I felt something different, more than just sex, but a validation of being a woman. I was so curious to see if I was turning him on.
He leaned in, and I couldn’t help but wanting to kiss him deeply. My mind raced, my heart skipped a beat as he leaned in more and laid a wet juicy kiss on my lips. To tell you the truth he was a horrible kisser but I found myself kissing back. His strong hand slid under my dress around the outside of my thigh to my ass and pulled me in closer to him. Then out of nowhere I slipped my hand to his special area. The feeling was incredible. He was so horny for me.
It was the first time I had felt another man’s special part, even if it was through his jeans. He was large, much larger than me. I felt a sense of pride that I was womanly enough to turn on a man, so, I was turned on. After a few seconds of rubbing him and kissing, the kissing actually started to go bad. He did something strange with his tongue and it didn’t feel right. I stopped him and came out of the trance that the martinis started.
“I’m sorry,” I told him. “But I really have to be going.” The look on Adam’s face was pained. I had been there before. I told him that he was a sweetheart and he was a great kisser, but I had a meeting in the morning and I needed some rest.
My apparent awakening also got the attention of Katie. They stopped and she too was gathering her things. The boys politely paid for our drinks, and Katie and I stood and left. My mind was replaying everything, and I was feeling woozy from the drinks and the extreme sexual experience I just had as a woman. I was both horny and sickened at the same time.
Katie must have realized something because she stopped me from entering my little car. “Why don’t you and I grab some drinks at my place?”
I told her that I was done for the evening. We then said good byes and left.
For the first time I felt so free. I have never been able to do that in a while. There was just something so sexy about making out with a strange guy. The drive home was relatively quick and my head was heavy and my body felt it had been in a fight. I parked in the garage and my heels clicked as I entered the house. My hair and clothes smelt of cigarettes and a tinge of Katie’s perfume. My feet felt some relief as I slipped out of the heels, and I looked at myself in the mirror. I was still aroused at the figure looking back. Then my phone rang. It was Debra.
Katie had informed Debra about what happened and she was a really angry. I was trapped now. I had no idea about how to explain it to her. My only choice was to tell her the truth. So, I started telling her everything. Debra was in complete shock and said she would come back home immediately. It was not going to be a week that I was expecting.