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Beautiful fate By Jungle Jane I guess you could say that my fate was sealed the summer I was thirteen years old. I was short, skinny, and awkward. I had just moved from Chicago, to a small Midwestern town, and I was having problems fitting in. I certainly did not fit in with the cowboys, the jocks didn't want anything to do with me, and I didn't want anything to do with the nerds. I was pretty much on my own at an age when kids need to feel they belong to something. My older sister, on the other hand, didn't have any problems fitting in. So, while my sister was out running around with her friends, and my parents were working all day, I found myself with a lot of extra time on my hands, enough curiosity to kill twenty cats, and an adolescent urge to experiment with sex. At first I was content to hide Playboys under my bed, but boredom and hedonistic desires soon sent me searching for new thrills. Everything changed the day that I found a pair of my sisters panties that had been mistakenly put with my clean laundry. I couldn't tell you what I was thinking as I eagerly pulled off my clothes, and slipped on the beautiful satin panties, I just did it. Almost immediately, I was hit with an electric charge of excitement, and my rather puny cock was harder than it had ever been. Before I even knew what I was doing, I started jacking off. The orgasm I had was more intense than anything I had ever experienced. But then it dawned on me that I had just jacked off in a pair of my sisters panties. I hurriedly stripped them off, put my real clothes back on, and went looking for something manly to do. After a couple of hours though, I couldn't get my mind off how good it had felt to wear satin, and wondering if I should try it again. And of course I did. By the time my folks got home that evening, I had masterbated a half dozen times. Each time, I would take the panties off immediately afterward, and swear I would never do that again, only to find myself back in the panties within an hour. The next day, I searched through my sisters drawers and found a different pair to try on. I also found a bra, which I just had to try on. Each day, for the rest of the summer, I would go into my sister's room, and find new things to try on, and each day I would add just a little more, until I was regularly wearing my sisters clothes more often than I was wearing my own. I had even began to teach myself how to put her make-up on. Toward the end of each day, I would wash my face, and carefully put everything back, swearing that it was the last time I would do that. Of course, that commitment would last only until the next time I found myself alone. Eventually, I got past the point that I felt guilty about dressing, and began to really enjoy the sensations of dressing. It grew even easier after my father left us. My mother had to take on a second job to make ends meet, and the little time that my sister spent at home grew less and less with each week that passed. I began wearing panties under my clothes nearly all the time, and grew to hate the few times I was forced to wear jockey shorts. By the time I was fifteen, I still had not grown much, I was still out of place in that small town, and I was still wearing my sisters clothes. After she graduated though, my sister moved out as well. I had managed to stash a few things away, and was able to continue to dress, but my selection was severely limited from then on. That is, they were until about the middle of my junior year. During the Christmas break that year, I had spent nearly twenty four hours a day wearing what few things I had. One day, I had decided to take a nap in my pink satin nightie, and was sound asleep when my mother came home early from work. I was horrified when she woke me up, and told me that we needed to talk. "Do you want to tell me why you're wearing make-up and girls clothes?" She asked. "I don't know, Mom," I told her, "it just feels really good to dress like this. It just feels more natural to me than wearing boys' clothes." "Are you gay?" She asked me. I sort of stumbled with that one. "I don't think so. Not really. I just like dressing like a girl. I mean, I've thought about it, but, not seriously or anything. I just don't know." "Do you want to be a girl?" The very thought of that made my heart beat a little faster, and my little cock stiffen. "I don't know. I never really thought about that. Honestly Mom, I really don't know why I do what I do, I just know that it makes me feel good. I'm sorry if I've upset you." "I'm not upset," she told me, "just a little surprised. I never really considered this before. I think, though, that I sort of like the idea. I'll tell you what, from now on, whenever you're at home, you can dress anyway you like, but you'll have to wear regular boy's clothes whenever you go out. If you'd like, I'll even see about getting you some new things of your own, instead of your sisters hand-me-downs." "I would like that a lot. Are you sure that you don't mind?" "I'm sure, I just don't think I want to try to explain it to anyone else. We'll just keep it between us for now, okay?" I readily agreed. I couldn't believe that my mom was not only okay with me dressing, but that she seemed to really like the idea. No longer would I have to stuff my favorite things in a box before she got home, and hide who I really was, at least not from her. My mom ended up taking the rest of the week off, and helped me out with a lot of things. Although I had been wearing make-up for nearly two years, she gave me some pointers on how to do a better job of it. She taught me how to fix my hair so that it was very pretty when I was dressed, but could easily combed out so that it looked more masculine when I had to wear boy clothes. She bought me some c-cup breast forms so that I wouldn't have to stuff socks in my bra anymore. She also decided that she just couldn't call me Lee when I was dressed, so she started calling me Leah. The name rang in my head, and just seemed to fit. The last day of Christmas break, my mom woke me up early, and fussed over me for nearly two hours until I looked perfect. That day, when I looked in the mirror, I couldn't find any trace of the boy named Lee. Instead, a very pretty girl named Leah looked back at me. Let me tell you, she was hot. I had never been happier than I was right then. That's when my mom told me that we were going shopping, and that I needed to go as Leah, so that I could try on some new clothes. "I don't know if I'm ready to go out like this." I told her. "Nonsense," she replied. "You look perfect. No one will ever know that you're anything but an attractive young lady. Women's clothes need to be tried, or you'll never find anything to fit right, so if we're going to find some new clothes to wear, you'll need to go with me and try them on. The only way to do that is to go as Leah. Now get your purse, and lets go. We'll drive into the city, so that we won't run into anyone you know. Everything will be fine, I promise." And so, Leah made her public debut that day. I couldn't believe I was actually going out in public like this. Their was an erotic thrill, and a sense of danger that made the whole day a big adventure. I loved every minute of it. I almost made a big mistake, and went into the men's rest room at the mall, but my mom caught me and pointed me in the right direction before anyone noticed. The day was perfect. I got a ton of new clothes, and my mom and I spent the day talking about everything, including, to my discomfort, boys. It felt so good, I couldn't believe that I had never done this before. I began to really live like a girl, becoming Lee only to go to school. My room slowly changed from an adolescent boy's to that of a young lady. I began watching chick fliks, and reading romance novels in my spare time. In almost no time, the mistakes I made in switching back and forth came almost entirely when I was dressed as Lee. I began to think of Lee as my second personality. I was truly Leah in every way. Every so often, when my mother would have some time off, the two of us would drive into the city for a girls night out. We would do some shopping or catch a movie. We even had our pictures done at Glamour Shots. One day, while my mother was at work, got got extremely bored. In my many adventures around the house, I had always avoided my mother's room. It just never felt right in there. On this day however, I decided to explore my mother's room. I found some jewelry that I tried on, and a couple of dresses that I knew I would have to try on some time, but I hit the mother load when I looked in one of the drawers under her bed. It was there that I found my mother's collection of dildos. I had heard about them, of course, but I had never seen one, and I was fascinated by the variety of shapes, sizes, and textures I had found. I knew immediately that I had to try one. I grabbed the smallest one I could find (I didn't want to get carried away just yet), and a tube of KY jelly that was there with them, and headed to my room. I didn't even bother getting undressed. I squirted some of the lube on the dildo, laid down on my bed, pulled my panties to the side, and placed the tip of the dildo against the rim of my ass hole. As I pushed the dildo in, I felt a little bit of pain, but it also felt very good, and my cock responded immediately. By the time I had pushed it nearly all the way in, the pain was gone, and my dick was straining against the silk material of my panties. I imagined a faceless stud laying over me filling me with his cock, and began to move the dildo in and out of my ass. I was rock hard as I began to fuck myself faster and faster. I took my other hand and reached under my panties to stroke myself, but just a touch was all I needed to explode like never before. When I pulled my hand out of my panties, it was covered in cum. I didn't even think about it, I just raised my hand to my mouth, and took my first salty taste of my juices. I left the dildo in my ass, and spent the rest of the day walking around with it right there. I fucked myself with it several times that day, and even moved up to one of the larger ones. When I went to school the next day I was very distracted. At first all I could think about was getting home and fucking myself again. In my last class, however, I found out that there was a new student in school, and he was from Chicago like me. Unlike me however, Mike was tall, muscular, athletic, and, I found myself realizing, very attractive. Despite the physical differences, we soon got to be friends (the first I had made in four years in this miserable town), and instead of going home that day, Mike and I went to Pizza Hut to hang out. As we talked, I was more than a little tempted to invite back to my house and introduce him to Leah, hoping he would really take a liking to her. But I was desperate for friends, and didn't want to do anything that might drive this one away, so I contented myself with that. When I pulled out my wallet to pay for my half of the pizza, he saw the picture I had taken and demanded to see it. "Whoa, who's that? That is one hot chick." "That's my, ah, cousin, Leah," I stammered, "she still lives in Chicago." "Yeah, well, you let me know if she comes for a visit. I would definitely like to spend some time with her." She'd like to spend some time with you, I thought, but I said nothing. I just paid for the pizza, and put my wallet back into my pocket. It was all I could do not to blush at Mike's inadvertent compliment. Mike had to get home, so he dropped off at my house, and drove off. Once he was out of sight, I ran into the house, tore off my clothes, grabbed a dildo, and proceeded to fuck myself silly. This time, however, the stud in my imagination wasn't faceless, he was definitely Mike. When I had finally satisfied myself, I threw my dirty clothes downstairs to get washed, and got dressed in something a little more appropriate for a teenage girl. Later, when I went to fuck myself again, I discovered that I had done something I hadn't planned on. In my rush, I had grabbed the first dildo I touched when I reached into the drawer. Now I realized, I had grabbed the largest one in the drawer. It was nearly twelve inches long, nearly as thick as my wrist, all black, and unmistakably shaped like a dick. Having done it once, I decided, why not do it again. And so I did, a couple of times. I had just barely gotten it back in my mothers drawer when I heard her pull her car into the driveway. The next several weeks were in some ways, the best of my life thus far. After four years of loneing it, I finally had a friend that I could hang around with, and whenever I was home, I could be Leah. In other ways, though, they were hardest weeks of my life. I couldn't tell my best friend who I really was, nor how badly I wanted him for something other than a friend. I thought often about telling Mike that Leah was going to be in town one weekend, and setting them up, but I couldn't figure out how to explain why we couldn't both be in the same room at the same time. Then, of course, if I got want I really wanted, I would have a lot of explaining to do, and most likely drive him away. I was so confused, even my mother noticed how distracted I was, and so I confessed everything, well except for the dildos anyway. The problem was, she didn't know what to do about it any more than I did. Mike finally discovered the truth in a way much different than I had hoped for. One day, after Mike dropped me off after school, I was sitting in front of my vanity putting on my makeup when I heard the door open. Thinking my mother had gotten off work early, I called out, "I'm up here in my room." I was still wearing my school clothes, and just finishing my make-up when he walked in and saw me. "Mike, what are you doing here?" "You left your backpack in my car. I thought I'd bring it back to you so that you could finish your homework. I knocked on the door, but no one answered." He looked around the room, taking in the dress on the bed, the pink comforter and drapes, the boy band posters, and of course the make-up on my face. "You want to tell me what the hell is going on here? That picture in your wallet isn't your cousin is it? It's you isn't it?" "Yes, it's me." I hung my head and stared at the floor. "I wanted to tell you the truth, I really did, but you're the only friend I have, and I didn't want you to hate me too. Please," I pleaded with him, "don't walk out of here and tell everyone about this. I really need you to understand." "I don't hate you Lee, or should I say, Leah, but I would be lying if I told you that I understood any of this. Why don't you get dressed, one way or the other, and we'll talk about it some more." He walked out then, and went downstairs, leaving me alone. With my heart pounding, I shed my school clothes, and got dressed the way I really wanted him to see me. After about fifteen minutes, I walked downstairs in dress and heels, to introduce him to Leah. Mike looked up when I walked into the living room. "Wow! Whatever else is going on around here, you sure do look good like that. I would never have thought that you were a, well, not a real girl." Despite my terror, I was thrilled to hear that from him. "How often do you do this?" "Whenever I'm not in school. When I'm at home, this is the way I look." "Does your mom know about this?" "Yeah, she's the one that took me shopping to get all this stuff. It doesn't bother her." "And is dressing like a girl the only thing you do?" "I'm not sure what you mean." I told him. "What I mean is," he said, "do you do other girl things, like read romance books, listen to boy bands, and spend hours in the bathroom? I mean, I noticed that your room is all pink and frilly." "Yeah, I do those things I guess. I don't know, I guess it just sort of goes with the territory I guess." "What about dating boys, do you do that too?" My heart skipped several beats. "I never have. I have thought about it though. Please don't tell anyone about this. My life hear is miserable enough as it is, if this gets around, my life is pretty well over." Mike sat on the couch and looked at me for quite some time, and I began to get even more uncomfortable, and just a little scared. Finally he spoke. "You know, if I hadn't seen it with my own eyes, I would never believed that you weren't really a girl. In fact, you look more convincing as a girl than you do as a guy. I've got to go, I still have homework to do. I was wondering though if you would wear something like this on Saturday, and go with me into the city to catch a movie or something?" I couldn't believe my ears. I wanted that more than I've wanted anything in a long time, but I couldn't talk. I just nodded my head. Mike began to walk to the door but stopped when he got to where he was right in front of me, then he bent down and kissed me. There was no thought, just passion and instinct. I threw my arms around his neck and kissed him back. When his tongue snaked out and parted my lips, I eagerly opened them to let it in. I melted into him as he put his arms around me and pulled me tightly against him, and I began to suck on his tongue as he moved it around my mouth. He held me so close that I could feel the swelling in his jeans. After a while, Mike pulled his mouth from mine, and looked at me sort of strange, though he didn't let go of me just yet. "I really do have to go," he said, "I'll see you tomorrow, OK?" Without another word, Mike walked quickly out the door. I felt as though this were all a dream. I knew that it had been real though. I could still feel his arms around me. I could still smell his cologne. I could still taste his tongue. I couldn't even wait to get upstairs. I simply sank to the floor right there in the living room, pulled my panties to my knees, and began to stroke myself furiously. The rest of the week drug by at an agonizing rate. All I could think about was that I was going on my first real date. I wasn't sure what I was going to tell my mom, but finally decided on the truth. I told her everything that happened, well except for the kiss and the jacking off. I was afraid that she would be mad, but I guess I should have known better. "It's about time." She told me. "A young lady as pretty as you should never be sitting at home on a Saturday night." Everything was working out better than I could have hoped for, except for the way that time seemed to stand still. At last it was Saturday. I spent nearly the entire day getting ready. I changed my mind about what to wear seven different times. At last I settled on a short red dress, with a moderately modest neckline, the cleavage wasn't real after all even with the breast forms. I also chose a pair of red lace panties and matching bra and garters. I was forced to wash my face and redo my make-up three times as I was so nervous I kept making a mess of things. I was just about finished when I heard the doorbell ring, and my mom answer the door. I nearly chickened out, but just then my mother came in to get me. "You're beautiful, sweetheart." She said. "He's here, and I think he's just as nervous as you are. I sure hope you kids have fun. I won't be home until late tomorrow, but try to be home by midnight. You can tell me all about it when I get home from work tomorrow." I thought Mike's legs were going to give out on him when he looked up and saw me coming down the stairs, and I felt some of the fear I felt begin to fade. The entire evening was a blur. I don't remember tasting my food when we ate, and I don't think that I could tell you what movie we saw. The only things I remember are Mike's smile, and the heat in my groin. When we got back to my house, Mike walked me up to the door. "Do you want to come in for awhile?" I asked him. "Is it okay?" He asked. I nodded, unlocked the door, and led him by the had into the dark house. We went over to the couch and sank down on it, our lips joined before we hit the back of the thing. At first, all I was aware of was the feel of his lips pressed against mine, but then I felt his hand on my thigh, and he began to rub it up and down. I parted my legs and encouraged him to move his hand upward even as I placed my hand on his thigh. Then, with little in the way of finesse, I reached up and began to rub his cock through his jeans. I've always known that my cock is somewhat pathetic, but even though his jeans, I could tell that Mike's cock was huge. Somewhat awkwardly, I managed to get both hands between us, and began to pull that monster out where I could get a better look at it. I broke away from our kiss so that I could look down and behold the object of my lust. I used both hands to rub his cock, and watched, fascinated, as it continued to swell even more. It was the most beautiful thing I had ever seen. At last I couldn't take it any more. Scared but determined, I bent down and took him into my open mouth. I tasted the pre-cum on the edge of his dick and savored the salty flavor. The blow-job I gave him probably wasn't very good. There was certainly more sincerity than talent in my efforts, but it didn't seem to bother Mike any. I was looking forward to tasting his cum, but Mike had other ideas. After some time, he pulled my head from his lap, and laid me back on the couch. He pulled my dress up, and pulled my panties to the side. Soon I felt the tip of his cock pressing against my ass hole. It was just like my fantasies as I looked up at Mike's face as he pushed his cock inside my virgin ass for the first time. I had always enjoyed fucking myself with a dildo, but that was nothing to the pleasures I was experiencing with a real cock. It didn't last very long though. Before I knew it, Mike was slamming his cock into me with wild abandon, and his hips began to jerk as he orgasmed. I felt the hot jets of semen shoot up in my ass, and it drove me over the edge. For the first time, I orgasmed without anyone ever touching my cock. I buried my face in Mike's chest as I was overcome by new and very powerful sensations. After a few moments, I felt my body begin to relax. I pulled my face from Mike's chest, only to have my lips meet his in a deep, lingering kiss. I was in heaven. After some time, our lips parted, and Mike pulled his now flaccid cock from my ass, and laid down beside me on the couch. I began to rub my hands around his chest, and told him, "I don't want you to go. Do you think you could stay for a while?" "I was hoping you would ask that." He told me, "I already told my mom that I would probably be spending the night over here. Of course, she doesn't know about Leah, but why bother her with details. As sexy as you are, it won't be long before I need to have you again." "Why don't you go and get cleaned up," I told him, " I want to change into something a little more appropriate for an overnight visitor. Give me about twenty minutes, and come meet me in my room." "You got it." He said, and got up and walked upstairs. I was getting aroused again already, just watching the way his muscular body moved through the shadows. When I heard the bathroom door close, I ran upstairs to my room. I knew just what I was going to wear. I soon found my sheer lavender gown, with matching satin panties. I wouldn't be able to wear the breast forms, but I hoped that would be okay, and the panties were snug enough to hold my tiny cock against me so that the front would look nice and flat, like a real girls. Once I was dressed, I lit several candles around the room, and was just getting on the bed when Mike walked in. Mike had shed his clothes, and as he stood naked next to the bed, I was overcome with desire all over again. I wanted him even more now, than I had when it had just been a fantasy. Not a word was spoken, as Mike leaned over and kissed me. I threw my arms around his neck and pulled him close to me as he climbed into the bed with me. His hands roamed freely over my body, bringing me to ever higher plateaus of desire, until my dick was straining against its satin prison. I reached down between us and began to stroke his cock, which was once again as hard as a rock. I began to push him up, and started to kiss my way down his chest and stomach, until he was sitting on his knees, and I could easily get my mouth to his cock. I continued to stroke him, as I began to run my tongue along the length of his shaft, and the bulge of his nuts. On sheer impulse, I sucked one of his nuts into my mouth, and Mike let out a moan of pleasure, and I felt his cock swell even more in my hand. Mike reached down, and gently rubbed my face as I sucked on his balls, first one, then the other, and finally both at once. After a while, he pulled his nuts from my mouth, and placed the purple head of his cock on my lips. I eagerly opened my mouth and let him in. When I had done this downstairs, it had been a quick, shallow head job, but this time, I wanted more. I pushed my head forward, until I felt the tip of his cock rub against the back of my throat. I suppressed the urge to gag, and pushed my way down even further onto him. At last I had his entire length in my mouth, and his nuts hung tightly against my chin. With one quick swipe of my tongue against his balls, I began to move my head up and down inviting him to fuck my face. At long last, I felt like a real women. I had been searching for this feeling since I was thirteen. Only recently had I realized what I had been searching for, and only now had I found it. For several minutes, I sucked on his dick like a women possessed, until at last I felt his muscles tense, and his hips began to jerk. Mike was going to cum, and this time, I was going to get a mouthful of it. I moved my head back, until only his head was still in my mouth, and when he came, the seamen exploded against the back of my throat. I stroked and sucked on his cock until I had milked every last drop of that salty elixir from him, and he pulled himself away from my grasp. After I had swallowed the last of Mike's cum, I looked up to smile at him, and was pleasantly surprised when he bent down and kissed me again. As we kissed, he pushed me back, until I was once again laying on my back, with him hovering above me. When our lips parted, he began to plant kisses down along my throat, to my chest, where he began to kiss my nipples through the thin material of my gown. He then pulled the strap of my gown down, so that he could uncover my breast, and then began to suck on my nipple in earnest. As he sucked on my nipple, Mike moved his hand until he was rubbing the inside of my thigh. He continued to rub my thigh until I felt it begin to rub against the crotch of my panties. When I felt his hand begin to rub my swollen little cock through the satin fabric of my panties, I just about came right then. Mike then deserted his attention to my breast, and began to work his way down, until he was running his tongue under the waistband of my panties. To my utter delight, he then pulled my panties down, exposing my dick, then placed it in his mouth. Given my small size, Mike had no trouble taking the entire thing in his mouth, and in no time, I was shooting my load in his mouth. Mike then pulled my panties off completely, and moved up until he could look in my eyes. When we kissed again, I could taste the salty flavor of my cum lingering in his mouth. I had to feel him in me. I reached down between us with my hand, to see if I could coax his cock back to life, and was pleased to discover that he was already set to go. I guided the head of his cock to the entrance of my ass, and pleaded with him to fuck me. Mike eagerly obliged, and in several slow, steady thrusts, soon had his cock buried in my ass. My own cock soon responded as well in response to overwhelming sensations of once again having a real cock fuck my ass. Mike started slow, but soon began to pick up speed. He then placed his arms behind my knees, and moved them until they were on either side of my head, and I was bent nearly in half. He then began to fuck me for real. Mike began to thrust his cock harder and harder into my ass, eliciting louder and louder moans of ecstasy from my lips. I was soon overcome once again by a powerful orgasm, and I felt my body twitch and spasm as it began in my belly and soon spread all over my body. Evidently, this was all that Mike could take, because he soon began jerking as well, and even before my own orgasm had faded, I felt the rush of hot seamen fill my insides. Once the rush of passion had passed us, we got cleaned up, and went back to bed. I had put my gown and panties back on, and Mike had put his boxers back on, and the two of us snuggled up together and fell asleep. When I woke up the next morning, Mike was still asleep, and I went downstairs to fix some breakfast. I was famished. When I walked into the kitchen, however, I stopped dead in my tracks when I saw my mother sitting at the table eating a English muffin "Mom," I said, "I didn't know you were home." "I took off early." She told me, "I got in early this morning." "What time did you get in?" I asked her nervously. She had a wicked sort of smile on her face when she answered, "I'd say right about the time you and Mike started screaming with passion. You were both quite vocal you know." "Are you mad at me?" "Of course not sweetheart. I've known this day was coming for quite some time. I'm just really glad it worked out okay for you. You're a young lady now, and you should enjoy all the things a young lady enjoys." "So, what happens now?" "Well, I'd say that's up to you. Now that you've truly experienced womanhood, though, you need to give some thought to how you want to live the rest of your life." "I don't think I understand what you mean, Mom." "I mean, are you satisfied being Leah part-time, or are you ready to make the switch to full-time. We could talk to a lawyer, and have your name changed to Leah permanently, and get you started on some hormone therapy, so that you could grow you're own breasts. Of course if we did, we'd have to move, not too far away, but at least a couple of towns over. Or we could leave things the way they are. I'm not going to tell you what to do. You're almost seventeen, and I think you're old enough to make this decision on your own. You don't have to decide right now, but think about it. I think I hear Mike moving around, so I'm going to go hide in my room for a while. I doubt that he's ready to face me yet. We'll talk about this later." With that, Mom grabbed her coffee, and headed to her room. Later, after Mike and I had made love again, and I had sent him home, Mom and I went out to eat and talked about my life. I made my decision that day. I was tired of being Lee, for even a small part of the day. That very week, I legally became Leah Standover. My mother and I moved at the end of that school year, and by the time we did, the hormones were beginning to take effect. Mike and I broke up that summer. He found himself a man to take my place, and last I heard, he was starting to wear dresses as well. It didn't take me long to move on either. By the time school started, I had met Justin, who has asked me to marry him as soon as graduation's over. I couldn't be happier. My fate was sealed when I was thirteen, but now it's set in stone.