Crossdressing True Confessions, Part Two

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 musculine. 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 Myrtle'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 Myrtle'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 apart of her attractiveness. She had amazing legs. I couldn't keep my eyes off of them when she was around and 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 Wally, 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 Janice," I thought it sounded good. "I just started working with Wally. 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 you 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, "Janice" would have loved some company. I couldn't believe really to what is 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 "Janice's" story. I answered it in the gruffest voice I had. Sure enough, she asked me about Janice. 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 affect 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, but my cock was placid and soft. 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, Katie wouldn't get as close as a guy would. I sipped away at my martini and tried to feel comfortable with Adam's arm around me. 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 explore more of 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 playing tonsil hockey 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 cock 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 no where I slipped my hand to his rock hard cock. The feeling was incredible. He was so horny for me. It was the first time I had felt another man's cock, 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. She grabbed my arm and pulled me in close and whispered in my ear. "You know the night doesn't have to end Wally." I froze. I looked at her with a helpless look in my eyes. Embarrassed, I told her that it would be fine to have a glass of wine with her at her house. As I drove to her house, following her SUV a thousand things were running through my mind. What could I say, and why not just go home? My worst fear was to have her call Myrtle and then all shit would break loose. I loved Myrtle and didn't really want to go through all that. As I pulled into her driveway of her cute little townhouse, I felt like throwing up. Katie once again slipped from her SUV and I, again, felt a twinge of sexual attraction as I once again tried as womanly as I could step from Myrtle's convertible. Katie smiled and took my hand as we entered the house. I plopped down on the couch and realizing how unlady-like it was crossed my legs. "So how long have you been like this?" She asked. "Today was my first day dressed in public." I explained in my regular voice. I resigned to telling her the entire story and the lie I told her in the car. She poured some wine and listened as I told her what I had done. "When did you find out?" I asked. "When I called you from the car, I saw you talking on your cell with me. You can talk to me as Janice." I cleared my throat and started again, "So you knew at the bar." She smiled, "Yes, and I have to say I was surprised that you kissed another man." She paused, "are you gay?" "No," I said. "I didn't want to blow my cover as a woman. And..." I trailed off. "And what?" she asked with a raise to her eyebrow. "And I wanted to see if I was woman enough to turn on a man." I said it quietly. "I see, you are very passable, maybe some more work on your makeup. Does Myrtle know?" "No." I was feeling embarrassed and sad, and I was getting drunk as the wine continued to flow. "Did you like kissing your man?" "No, he was a horrible kisser." Katie began to laugh and she sat next to me on the couch with her wine. Her hand lay on my knee. It felt comforting. "Well, your secret is safe with me." She said almost as an after thought. I was confused, and look at her with fallen eyes. "Look, most of my girlfriends are married. None of them want to stay single anymore." I didn't really know where this was going. "For the first time I felt so free to just..." she was trying to find the words. "You saw me with that guy." I nodded, she continued. "I have never been able to do that in a while. There is just something so sexy about making out with a strange guy. And with you there, I felt safe. I knew nothing was going to happen." She leaned in and kissed me fully on the lips. I loved it. Her hand on my leg was moving up. My head was swimming and my johnson was finally coming alive. Our kiss was passionate but not overly active. The mix of her lipstick and mine made the kiss slippery, but not wet. Her lips were full and beautiful and I felt as if I was in heaven. Her hands reached as far as the tops of my black stockings and stopped. Although, I would have let her go farther up my leg as she wanted. The smells, the feeling were all intoxicating. When Katie had finished kissing me, which seemed to last for minutes, she looked at me deep in my eyes. She gave me big doe eyes as she began to ask. "Would you be my new girlfriend?" Shocked, I stood up. I was coming to my senses. "Look, it really was a mistake doing this. I just did it to get off tonight. I never expected to go out really, or run into you. Let alone kiss some guy." She listened very intently as I continued. "I want to have sex dressed like this with a woman, but I really don't want to cheat on Myrtle. I just don't want to jeopardize that, not now. Really this just was an opportunity to be a pervert." It took her a while to digest this information. I wanted her so much, to lean her back on the couch and hump her with my nylon covered legs around her. But it turned to be a serious conversation. I was ready to go home. She stood up and gave me a big hug. Our heels click together and our legs rubbed. Her perfume and my wife's were mixing in the air. She pulled away and looked at me. "I can understand, I mean, I guess, I know what you're going through, but I am turned on by you right now. And this could be our little secret. You don't have to kiss guys if you don't want to." Some how what she said comforted me and turned me on. I leaned into her and gave her a peck. "I should go home." "Are you dressing tomorrow?" Katie asked. "I don't know?" "Please do, and call me." She smiled and hugged me again. I walked back to my wife's car and again slipped in as a woman. 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. My legs looked so good, even out of heels, and my hands began to rub over my body. I started to strip until I was naked except for my pantyhose were around my ankles. I stood there with my penis in my hand looking at my face framed in brown hair and in makeup. I didn't jerk hard like I used to, but instead kept a slow and deliberate pace until I relieved myself. I relived all the events of that evening. Thoughts ran through my mind about dressing up, kissing Adam, getting caught by Katie and the deep kiss we shared. When I was done, I cleaned the mess up and took a quick shower to wash the makeup off. Then I slipped into some of my wife's panties and went to bed. The very next day Katie came over and she said she was there to take me shopping as Janice, so she helped me with passing off as a woman dressed in a jogging suit of Myrtles'. Katie and I made a day of it, she said anytime Myrtle is away that I should come to her place for a more formal deportment of being a woman. Alas, the entire week we spent together and we found a quaint little place where I live in Sunrise, Florida that has everything from A to Z aimed at people like myself!