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The Drive "Have a nice trip home, dear," my mother said to me as I walked out the door. My heels clicked on the stones of her Florida pathway leading from her front porch to my car. It was still humid from the afternoon rain, and I could feel the beads of perspiration start to form on my forehead. Hopefully, the air conditioning in the car would continue to work in the heat. As I sat in my car, I smiled and waved at my mom. She has always been so worried about me when I am travelling, still wanting to protect her little girl. I checked my hair and makeup in the mirror as I started the car and pulled onto the street of her private community. When I got to the gate, Charlie the guard smiled and waved at me as I pulled up. "Have a safe trip home, Stacy," he said. His smile was quite sincere. I knew that he liked my mother and that my circumstance was not lost on him. For a seventy year old man, he was decently open-minded. I honked as I drove through the gate and began the twenty hour road trip to my apartment in Omaha. One of life's greatest pleasures for me is driving. I love the feel of the car around me as I move through the curves and hills. I have driven thousands of miles to see sights that many people have only dreamed of visiting. My personal wealth has allowed me the financial security to take months off at a time to pursue my passions. My business is run by my secretary. She is more capable at it than I am, and I compensate her generously. We are a small publisher of limited circulation books and periodicals. I think she is a bit relieved when I go on my driving trips because it gives her a chance to correct any mistakes that may have occurred while I am there. So it was that I had just spent a month with my mom in her posh home in Florida. She pampers me every time I visit. We go shopping and have lunches in the cafes and just spend some great mother-daughter time together. She always asks me about my love life, although I always disappoint her with no real news. But my favorite part of the trip is the drive. It takes me twenty hours to get from her home in Florida to my apartment in Nebraska. I try and leave in the afternoon and arrive the next day. I am too excited to sleep through the night, so I tend to drive straight through, often stopping at little towns on the way. I always buy myself new clothes to wear when I drive for long distances. Earlier in the week, I bought a cute beach ensemble at a quaint gift shop by the marina. It included a pair of white sand Capri pants, a cute little sleeveless shirt with a coral design on the collar, peach colored bikini panties and a comfortable, yet elegant white, lacy bra. My sandals have a small heel which I liked the sound that they made when I walked as I tried them on. I took a few minutes to shave my legs and fix my hair before I left, knowing it had to last for a day. My sandy blonde colored hair with just a touch of a curl at the shoulder matched my Florida tan perfectly. My lips were splashed with a soft pink gloss, my eye lids colored slightly and my lashes highlighted. And for kicks, I sprayed a bit of body glitter on my face and chest. I must admit that I looked stunning. Maybe that is why Charlie at the gate smiled so much. I drove out of town with a small ache in my heart. It is always good to see my mom, but leaving is sometimes tough. She helped me through some rough times as I was growing up, mostly because I believe that she was one of the only people that could understand how I felt. She knew that I was not comfortable as the gender of which I was born, and was encouraging when I finally came to terms with it. My mom was a single parent for my entire life, my father unknown to me. I have an older sister that is in Los Angeles working as an editor for a newspaper. Growing up with an older sister and a single mother helped me realize that I was truly meant to be a girl, but somehow, I born into the body of a boy. The earliest memories that I have are feelings of delight as I would dance around in my sister's dresses when I was four or five years old. My mom and sister would dance and sing as well. We would laugh and laugh as my sister and I would put on my mom's makeup and pretend to be grown up, looking more like clowns than adults. Eventually, I began to want to wear the dresses more and more, and my mom and sister didn't seem to mind. I remember the day that my mother looked at me in a serious manner and said we needed to talk. I was about ten years old and was just coming down stairs from my room where I had put on a cute satin blue dress that I had dug out of my sister's room. I had white tights and black buckled shoes. My mom sat me down and said that I looked very pretty. She spoke in a grave tone and I could tell she was upset. "What's the matter, mom?" I asked, not realizing the discomfort that I was causing her. She said that as I would start getting older, I would begin to have friends over to the house and that dressing as a girl might not be the best thing to do. I dressed in my boy clothes at school, but lately I would come home and put on my girl clothes right away. She explained to me that some people might not appreciate how nice I looked in a dress and treat me terribly. I looked at her a bit dismayed and said that I wish that I could wear my dresses to school, too. I could see that my mother wanted to cry, but she held it back. She just wrapped me in a hug and said that she wished I could as well. The next morning at breakfast, my mother told me that if I wanted to be a girl at school, then I could. She took me to school that morning and went right to the principal's office where he and my mother talked about my situation. He was very upset and I could tell that he didn't want me to be a girl at school, but my mother kept talking about how much it would cost him in court to deny me the right to be who I wanted to be. In the end, the principal agreed to allow me to wear girl's clothes as long as it was not a dress. He didn't want to confuse the other children, but he agreed that I should be able to express my feminine tendencies as I wished. My mother said that he was a wise man and we left his office. Instead of going to class, my mom took me out to a restaurant and we talked about what my life would be like. That afternoon, we did some shopping for new clothes and when we got home, I got to box up all my boy clothes to be donated. I was the last time that I would ever wear boy clothes again. The next day at school, I wore a new pair of cute jeans with hearts on it, pink socks, a pretty white shirt and a bracelet. I was wearing one of the cute cotton panties I had picked out, and my mom even bought me a trainer bra to wear around the house. It was the first time in my life that I was comfortable with myself. As I left the beautiful neighborhoods of south Florida, I smiled to myself as I remembered of all of this. My mother was a Saint and would be rewarded greatly in her next life. After driving for a few hours, I pulled into a gas station convenience center to fuel up and get a bottle of water. I still get a lot of stares from people, because even though I have perfected my female look, I still have some manly features. If someone looked closely enough, they could tell that I was a man dressed as a woman. I have gotten used to using the women's restrooms at restaurants and private clubs, but when I am out in public, I use the men's room to protect myself from any legal action. I am still a man, with male parts, but that is as far as it goes. So, when I entered the men's room of this store, I had to steel myself for what I knew would come. I finished in the restroom and as I went to the counter to pay, I got the typical slurs from the clerk as well as the "you'd better just leave now" looks from many of the locals. Just for fun, as I was leaving, I winked at the teenage boy that was staring at me with him mouth hanging open. The warm sun was just starting to set as I left Florida. I entered Alabama with a sigh and decided that I needed something more to eat than chips and bottled water. I grabbed the closest burger I could find and continued on my way, enjoying the night driving. There was a hollow ball of need starting to grow in the pit of my stomach. I knew what it was, and I was surprised that it took this long to begin. Here I was, dressed in my cute outfit, driving through Alabama, and all I could think about was sex. Sex for me has been an area of frustration, and yet satisfaction at the same time. I get frustrated because I very much enjoy the beauty of a woman, but I also crave the attentions of a man. My forays into relationships with understanding women have ended in disasters, and finding a man that likes who I am has been difficult. I often have to settle for quick sexual encounters or just plain self gratification. But when I drive, I always get extremely aroused. At about one in the morning, I was driving down an Alabama interstate when my urge to pee became more than I could bear. Rest area bathrooms have always been a potential hazard for me because you never know who might be lurking in the shadows of night. I have read stories where people have been mugged, raped, or worse at rest areas in the middle of the night. As a transgendered person, I was especially susceptible to the wrath of narrow minded individuals. I pulled as close to the front of the rest stop building as I could, seeing only two other cars in the lot, with a few semi trucks on the other side of the building. I was relieved to see it so empty, thinking that I might be able to get in and out as quickly as possible without running into any trouble. I grabbed my purse and locked the car as I left to walk up to the restrooms. When I entered the building, I saw a young man standing in the foyer looking nervous. He looked at me and for a moment our eyes met. He appeared to be in his early twenties, and a little geeky, but he had the most gorgeous blue eyes I have ever seen. We looked at each other for a brief second until I forced myself to turn away. I had to make a quick choice to use the men's room or ladies room and decided to continue to the men's room. I entered one of the unoccupied stalls and pulled my capris and panties down as I sat on the stool. The restroom was cleaner than most, which was a relief. No other stall was occupied, so I thought that I might just get out without any incident. Just as I was about to pull up my panties, I heard footsteps come through the entry to the men's room. Now I would have to wait until whomever walked in was finished to make my exit. I saw a pair of sneakers walk by the stall and then turn around and stop right in front of my door. I heard a soft tapping on the door and my mind went into hyper drive. What was I going to do? Would I be mugged, raped, or arrested? This was ALABAMA, and I bet the local people didn't take too kindly to transgendered people. "Hello," a soft male voice came from the other side of the door. "Can I help you?" I squeaked. My mind raced through possible escape routes and what I could use for self defense. I realized that I was still sitting on the stool and quickly pulled my panties and capris up and put my purse on my shoulder to make myself ready. "Um, I saw you come in," was his reply. "Are you here to meet me?" "Meet you?" I said incredibly. "No, I'm just driving through." I wasn't sure what to do, now. "I was supposed to meet someone like you here over an hour ago." I realized at that point that the sneakers on the other side of the stall door belonged to the young man that I saw as I walked in. "Someone like me?!" I said with a touch of heat. Nothing gets my anger up more than generalizations and stereotypical thinking. "What do you want?" "No. Yes. No. I mean-I was supposed to meet a crossdresser here that I met in a chat room, and I saw you walk into the men's room, so I thought that you were her...Ah, him...Ah, are you here to meet me?" The poor boy was in knots. But he must be really horny to have gotten the courage up to do this. I opened the stall door and our eyes met again, those dreamy eyes taking my breath away. He looked down right away and backed up a few steps. I got a closer look at him. He was wearing faded jeans, a button oxford and those old sneakers. His hair was a sandy blonde like mine, and he still had a boyish look to his face. "How old are you?" I asked. "I'm twenty two, ma'am." He looked up again, seeing the possibility of an encounter start to take shape. I could smell his eagerness. Oh, he must be extremely horny. That hollow ball of need inside me started to become more persistent as I started to see the possibility of an encounter as well. "Are you a cop?" I asked for my protection, "and how do I know you are really twenty two?" He hastily pulled his wallet out and showed me his Alabama driver's license that showed a date of birth that, after a few seconds of calculation, indicated that he was indeed twenty two years old. Although he was boyish looking, he was uniquely handsome, and looked to be in his sexual prime. He was definitely eager because I could detect a slight bulge starting to grow in his pants. I didn't have any kind of time schedule, and I was getting aroused myself. Perhaps, I could take advantage of this situation and have a little fun. "What is it that you were expecting to find tonight?" I asked in a coy and girlish voice and took one step toward him. His smile was immediate and I could tell his bulge got bigger in that instant. His eyes seemed to pop out of his head as if to say, "Wow, this is really going to happen." "I have never done this before," he stammered as he looked around the restroom. In a low voice he said, "I was looking for crossdresser to have sex with." He looked around the restroom again, and I realized that this conversation should probably happen somewhere else. I boldly took his hand and led him into the last stall. As we closed the door, we stood very close, almost touching each other. I could feel his hot breath on my cheek. That hollow ball of need became an urgent sexual desire to have this young man right now. I felt a well of heat rise from my groin to my face as my own penis started to ready itself for pleasure. I made my decision then that sex was going happen, and I just hoped this boy could take it. I looked up into his face and our eyes met again as I moved forward to kiss him. His lips met mine and we melted into each other. His hands went right to my hips as mine came up around the back of his neck to pull him closer. He moved his hands to cup my ass as our bodies tried to push themselves into each other and I could feel his cock rising in his jeans in excitement. My penis was straining at my panties as if it wanted to break free and jump into this boy's hands. I kissed him passionately, moving my tongue into his mouth and he kissed me back just as eagerly. I pulled away to get a breath of air and I heard someone urinating in a stall a few down from us. My eyes became saucers as I put my finger to my lips to say to him "shhhhh!!" We heard the toilet flush, the patron wash his hands and exit the bathroom, all while we were still holding each other. His cock was straining at his jeans and I looked into his eyes again. "We can't do this here," I said. "Your car?" He smiled and nodded his head. I don't think he could have said a word, he was so aroused. I grabbed his hand, opened the stall door and peeked out to see if anyone was still in the bathroom, and then led him out of the building. The darkness was helpful. To anyone not paying attention, we were just two young lovers walking hand in hand. I asked him where his car was parked and he pointed toward the beat up Chevy Caprice parked in a darker corner of the lot. I smiled as I looked at the size of the back seat and said, "Perfect!" We climbed into the back seat and started right in on where we left off in the bathroom stall. This time, my hand was probing his chest and then down to his crotch. He was really aroused. One of his hands was on my breast and the other cupping my ass. I tried to unsnap his jeans, but I couldn't quite get it while I was kissing him, so I pulled away and concentrated on opening his pants. He leaned back and moved his hips a small bit closer to me as if to say, "Here you go." After a good deal of effort, I finally got his pants undone and unzipped. I pushed my hand inside to free his cock and I felt the most wonderful thing in the world. He was wearing panties?soft nylon full cut briefs?probably Vanity Fair. His cock was tenting the nylon and I could feel the precum already starting to wet the fabric. I smiled at him and teased, "Are these your mother's?" "Yes. They are pink," was all he could say. "Oh, you naughty boy," I teased again and started to pump his cock in his panties. I saw his eyes roll to the back of his head and in about four seconds, his hips were moving to my hand pumps. A few moments later, he let out a moan and his cock started to cum all over the inside of his panties. He unleashed a flood of cum and it started to filter through the nylon material and soak my hand. He continued to pump his hips for a few more moments and then collapsed with my hand still on his cock. He was breathing hard and his eyes were closed, probably trying to bring himself back to reality. The smell of his cum was too much for the lusty heat coursing through me so I bent over his body and started licking the strained cum from his panties and my hand. I lapped it up like a dog, licking every inch of his cock through the nylon, as it started to twitch back to life. "What are you doing?" he asked when he finally came back to reality. "You are not getting off that easy, missy!" I mouthed around his cock. "I am not satisfied, yet." His cock slowly started to rise again as he understood the implications of that statement. He was again pushing the fabric of his mother's panties to the limit. It was soaked with my saliva and his cum residue. I pulled myself up from his lap and reached for my purse. I always carry a few girlish essentials in it for just such an emergency. I pulled out a pair of white bikini panties and continued to dig around. I finally found my travel size KY lubricant and then stuffed the panties back in the purse. I pulled off my capris and then pulled down my panties, which were already soaked with my own precum. I reached over and pulled his cock out from the top of the panties and dabbed a bit of KY on the tip. "Now you are going to fuck me," I breathed heavily. His eagerness overwhelmed him and he bumped his head on the ceiling as he started to move around. I put my hand on his chest to slow him down as I turned around in the seat, pointing my girly ass in his direction as I leaned over. His hands were instantly on my hips and I could feel his cock already pushing against my hole. "Slowly, please," I said to him in a tone that meant no nonsense. He backed off a moment and then proceeded to slowly push his cock into my ass. It moved easily with the lubricant and his head popped past my sphincter and into my hole. He showed some self control and continued to move slowly into me. He could have easily rammed me home and caused me immense pain. He slid his cock slowly in and out and I could tell he was already ready to cum again. The feeling of having this boy's cock in my ass was remarkable. My penis was pointing straight at my face as I was bent over the seat, being fucked like a teen age slut. His motions started to get quicker, and I knew if I were going to cum I had better do it soon. I leaned to one side and grabbed one of his hands from my hips and guided it to my cock. I wrapped his hand around it and he automatically started to stroke me. He got into a rhythm where every time he thrust into me, he stroked my cock. Soon, he was flying in and out of my ass, stoking me like mad. I couldn't wait any longer and my cock sprayed cum all over his back seat, a small drop or two getting on my cheek. At the same time, he shot his second load of cum into my ass, climaxing convulsively, as if he was having an epileptic episode. Once he was spent, he slowly pulled out of my ass and sat back, smiling contentedly. My breath was coming in short gasps as his cock slid out of my hole. I moaned and swam in a sea of ecstasy with the last spasms of my orgasm. My cock was raw from his hands and I could feel the little droplets of cum on my cheek. As I sank down onto the seat of the car, I dabbed the cum with my finger and brought it to my lips. I love the taste of cum, especially my own. I came back to my senses and could feel my ass starting to ache from the pounding that it took. I would be leaking his cum from my sore hole for the rest of the drive home. I blindly searched for my panties, finding them wrapped around my ankle, and pulled them up. Finding my purse was a little harder, not realizing what I did with it after getting the lubricant. I finally found it flung near the back window, completely amazed on how it could have ended up there. I pulled a small maxi pad from the purse and opened the little white package. Still foggy from the sex, I managed to pull the paper, apply the pad to the crotch of my panties, and pull them back into place. I caught a small grin from the boy as he watched this process with amused interest. "Your really are a girl, aren't you?" he asked. He was still bare below the waste and had his mother's panties in his hand. "Yes. I have been for as long as I can remember. What is your name, by the way?" Here I had just had some of the greatest sex in my life and I didn't even know his name. "Todd," he smiled as he put his hand on my knee. I could tell that he was a bit lost inside himself and guessed that this was his first time with another man, although one that was more woman than most. "I am Stacy," I smiled at him, hoping to put his mind at ease. Looking at the cum soaked briefs in his hand, I asked, "what are you going to do with those?" "These are the only pair that I have. I don't dare try and take another pair from my mother." He seemed so innocent in his concern, worried about if his mother will find out. I reached into my purse and pulled out the spare pair of white nylon panties that I save for emergencies, and handed it to him. "I think these will fit you. You should have a pair of your own, Todd." Saying his name was nice. He was a sweet boy, just starting his adventure into crossdressing. "Keep them to remember the fun we had tonight." I could tell he was grateful. He bent over and kissed me on the mouth, his soft, warm lips stirring that ball of need once again. I lingered in his kiss as he pulled away. He pulled on the panties and smiled as he moved his hands across his hips and ass. "It looks like they fit very well," I said as he seemed to lose himself again. I moved toward the door to make my exit when he touched my hand. "Stacy, will I ever see you again?" he asked. I could tell he was struck with the realization that we were complete strangers and that he had no idea where I was headed. I smiled and slid out of the car, turning to look at him one last time. "Here. Call me if you are ever in Omaha. I would love to see you again," I said with a smile as I dug out a business card from my purse and handed it to him. I truly meant it. He took the card and sheepishly looked at me. "You are a wonderful lover, Todd," I said. "I will remember this night for a long time." I looked one more time into those blue eyes and turned away before I could consider getting back in the Caprice. As I got to my car, I felt as if I had just lost something dear to me. I looked at the big Caprice and saw that Todd was just getting into the front seat. I waited to leave until he had pulled out and drove off down the highway. I applied more lipstick, scrubbed a bit of dried cum from my cheek, and then started my car. I could feel Todd's cum starting to leak out of my girl hole into the pad, the smell of his cum coming back from my memory. I smiled for a long time while I drove toward Nebraska, stopping at almost all of the rest areas on the way. I don't know what I was looking for, and I certainly didn't find it, but I will always remember. My life in Omaha went back to working at my publishing business, eating out with friends, and calling my mom. I didn't tell her of my escapade on the way home from her house, although she probably would have been glad to hear about a relationship, albeit a short one. As I was pulling into the parking lot of my office building one morning, I caught sight of a large Chevy Caprice in one of the spaces. Something inside my stomach flipped around as I caught the memory of that wonderful tryst with Todd. I dashed any hope that my mind was conjuring, rationalizing that it was dark that night, and that this car couldn't possibly be his. I pulled into my parking spot and fluffed my hair. I stepped out of my car and looked toward the Caprice. Todd was leaning against the car door?he must have gotten out as I was fixing my hair. He had a delirious smile on his face as he looked at me. I was dressed for work, wearing a knee length white skirt, a soft yellow blouse and my white heels. I walked toward him, not knowing what to expect. "What are you doing here?" I asked as our eyes met. Oh those beautiful eyes. "How did you find me?" "You gave me your card, remember. Oh, Stacy, you look great," his smile was sincere and I think that I actually blushed at his attention. Then he said, "My mom found her panties when she was looking for something in my car. She freaked out even more when she saw the cum stains on my back seat. She called me a lot of names and demanded that I pack up and get out." I could tell he was close to tears at the memory. "That was two days ago. I didn't have anywhere to go, so I thought of you. I don't know, maybe I really just wanted to see you again." I put my hand on his arm and stepped close to him. "Oh, dear. I am so sorry." "Don't be. I needed to get out of there anyway. Is this where you work?" He pointed up to the building, obviously uncomfortable with the memory. "Yes. I own the business. We publish books and magazines for small markets," I said with just a bit of pride. "Come in and meet my secretary, Candace. She really runs the business. I am only here for show." He smiled at that last comment, as I took his hand and walked him into the office. I was smiling broadly, feeling like a giddy schoolgirl on a date with her boyfriend. I had to admit to myself that I was very glad to see Todd again. I couldn't get him out of my head after I returned to Omaha, often laying awake at night, reliving our encounter at the rest area. Candace, Candy as I like to call her, looked up from her desk when we entered. I could tell what she was thinking when she saw us walking hand in hand. Her smirk said "OK, now what!!" She has gotten used to my little eccentricities and probably started to calculate how much time and money this was going to cost the business. She was a tall woman, taller than me, with a slim figure, but curved in just the right places to make her look feminine. She wore a smart business suit with a black skirt and jacket over a sheer white blouse. I have often been envious of Candy for her figure, and even had the occasional sexual attraction to this woman, but I know that there would never be anything that would come of that desire. She knew, of course, that I was genetically a man, but she treated me like another woman. I have worked with her for seven years, since the inception of the publishing business, and there is not another person in the world that I would consider a closer friend. We would often go to have drinks after work, but the conversation was always about my drama or about something at the office. Only rarely did we ever talk about her personal desires and wishes. She was a closed woman, but I felt like I could tell her anything. "Candy, this is Todd," I announced with excitement. Her eyes lit up in an unusual show of surprise, but she recovered quickly. "THE Todd?" she asked with a hint of disbelief. "THE Todd from Alabama, in the middle of the night?" As she said that, I felt a bit of embarrassment come over me. I think I blushed again. I looked over at Todd and thankfully, he was smiling. "Candace and I are very close," I tried to explain. "I told her all about you. I never really thought I would see you again. I mean...I wanted to...but, you know...the distance...and..." I stammered. I can't believe that I was acting like a smitten girl in the midst of my own office. I looked at Candy and she was grinning like a cat at my embarrassment. Oh, the nerve of that woman. I shut my mouth before I accumulated more disdain from Candy and led Todd into my office. I shut the door behind him and leapt into his arms, kissing him passionately. He tasted so wonderful and his arms around me felt so good. He returned my kiss and I could tell he was happy to see me as well. We kissed for what seemed forever, finally pulling away from our embrace. A sexual heat was pulsing through my body and the vision of his cock pumping me in the back seat of his Caprice wouldn't leave my mind. I caught my breath and asked him to sit down in one of the upholstered chairs that were arranged in front of my desk. "Now, tell me what is going on," I said as I leaned against the side of the desk, smoothing my skirt and adjusting my blouse. I can't believe how nervous I was acting. He reiterated what transpired with his mother and how he had packed up his belongings and left when she told him to get out. He travelled for the day and arrived in Omaha last night, getting a hotel room at a sleepy inn by the highway. He found out where the office was located from the address on the business card, and here he was. "I was hoping that you could help me out with a place to stay. I know it is asking a lot of you, especially from only knowing you for just a short time, but I just felt like this was the right thing to do." He looked at me with those eyes and I had to concentrate very hard not to go dreamy and forget what I intended to say. "I own a few furnished condos that I keep for clients, and you are welcome to stay in one for awhile. But what will you do now that you are here?" He smiled and looked the card that I had given him weeks ago. "What about working for you?" he asked. "I have an Associate Degree in Creative Writing and another in English Literature. The fact that you are a publisher is great, because I would be looking for some editing work anyway." A smile came to my face, and my eyes lit up with excitement. "Junior editor, working on fact checking and grammar. You can start tomorrow. The condo will be part of your benefit package. I will make the arrangements with Candy this afternoon." His eyes were round with excitement, and held mine for an instant. "Why wait until tomorrow," he beamed. "I can start today." He was on his feet, eager to start working for a woman that he had met at a rest area to have sex with just a few weeks before. It seemed almost too surreal. "You will start tomorrow," I said in a sultry voice. "Today, we have to discuss the rest of your benefit package," I purred as I locked the door of the office and turned to face my lover. The heat of my sexual desire was burning like a firestorm inside me and I was not about to waste this opportunity. To be continued.................................