0 comments/ 198486 views/ 19 favorites Karen's Story By: Lisa433 Chapter One - In the Beginning My name is Charles Ankersby. Well, at least it used to be, and this is the story of my life. It tells the tale of how I came to be Karen Miller. No, you're wrong. This isn't just another autobiography of a transsexual. I'm a transgenderist and, if you're not aware of it, that's a whole different thing. It's an almost true story. It happened just the way I'm going to tell it to you. I have changed some names in order to assure anonymity for the other people involved. Later, if they're proud and want to brag, they can identify themselves, but I won't. I suppose my Aunt Jeannie, my mother's younger sister, had a lot to do with the way I turned out. My parents died when I was young. Aunt Jeannie came to me after their funeral and said my parents had asked her to look after me if anything ever happened to them. She said she'd love to take care of me. Jeannie was twenty-four at that time, and one of the loveliest women I've ever seen. At five-foot four inches tall and weighing just over one hundred pounds, she was in wonderful shape. She had shoulder length dark auburn hair and green eyes that enthralled anyone who looked into them for more than a second. I had always liked her a lot, probably because she'd always spoiled me so. She spent a lot of time at our house and was like a second mother to me. In some ways I had been closer to her than I was to my parents, so when she told me I'd be living with her, I was pleased. It worked out well for both of us. Between the insurance settlement from my parents' estate and her alimony, Jeannie could afford to quit work and stay at home while she looked after me. That made it easier on her as she had always detested working for someone else. A year or so after I'd moved in with her, she came home unexpectedly one day from shopping and caught me trying on some of her lingerie. I was panic stricken but thankfully she didn't make a big fuss about it. All she said was, "Chuck, we're going to have to talk about why you like wearing my clothes. Please don't misunderstand me. I'm not angry with you. I don't mind it at all, but I think if wearing my clothing is important to you, it's something we must discuss." I decided I had to be honest with her and trust her. There was no point in my denying it. I was standing right in front of her, wearing her pink full slip and panties, with a very obvious hard on. I felt completely ridiculous. There were tears rolling down my cheeks. "I don't know why," I explained, "but I like the way your clothes look on me and the way they feel. I've been wearing your things for a couple of weeks, but I didn't want you to find out about it because I was afraid you'd laugh at me or punish me." The look on her face told me she'd do neither. She took me in her arms and said softly, "I love you and I want to make you feel comfortable living here. So if it's important to you, then it's something I'll have to deal with. Please don't ever be afraid to tell me anything. I'll always try to understand and I promise I'll never laugh at anything you feel is important." "Ok, Aunt Jeannie, I promise I'll tell you everything from now on. Thanks for not being angry. I love you so much," I said, and I meant it. From that day on, when I'd come home from school, she'd be waiting for me at the door. We'd talk about my day and then she'd have me take a bath. When I got out of the tub, some of her lingerie and clothing would be on my bed, just waiting for me to put on. As she has a small build, almost everything of hers fit me or was slightly large. I'd spend the rest of the afternoon with her, helping her get dinner ready or doing my homework. After a few months, I became very comfortable in her clothes. I even got so I could walk in heels without breaking my neck. One day when I was older, Aunt Jeannie told me it was about time that I stopped dressing in her things. For a moment I was very afraid, thinking she wanted me to stop wearing her clothes, but that wasn't it at all. "After all," she said, "you're not a child anymore. You're at the age where little girls become big girls. I think we should spend this weekend changing you into a young lady. Would you like that?" "Oh, yes," I exclaimed. I was excited, but a little embarrassed by my enthusiasm. But, as usual, she always seemed to know exactly what was on my mind. "I've been thinking about that a lot lately and I'd really like it. Some of the girls in school have begun to develop and I guess I'm jealous. How can I be a woman, though? I know I'll never grow boobs." She smiled at my embarrassment. "That's probably true, but there are ways to make up for what nature hasn't provided. Women have been doing it for centuries. I'll make you beautiful, you'll see. Just trust your Aunt Jeannie. She knows what she's talking about." "Oh, I hope so. I'd love to look as pretty as you do, or like some of the other girls at school. I see the boys staring at their chests as they walk down the hall. It's very confusing for me. When I look at them I feel turned on but envious too. Maybe it's because even though I like girls, I guess I want to be one too." Aunt Jeannie gave me a very surprised look. "That's the first time I've heard you say you wanted to be a girl. When did you decide that?" "I don't know. I guess maybe I've always felt that way. Spending a lot of time in your clothes has made me realize I'm much more comfortable as a girl. I guess I'd have been happier if I'd been born that way. Does that make me weird or something?" "Believe me, you're not weird. There are a lot of people in this world who feel exactly as you do. Many of them eventually end up having operations that change their sex to the one they feel they should have been born as. It's becoming more and more common all the time. So don't think you're a freak. You're definitely not. "But enough talking," she said. "Let's see what you're going to look like as a young lady. Go hop in the shower. Make sure you shave your legs and underarms well. We want you looking your best today." She gave me a pat on the rump to speed me on my way. I felt a lot better knowing I wasn't alone in the world. I didn't want to be a freak. I quickly undressed and got into the shower. I couldn't wait to see how I'd look as a mature woman. I shaved my legs and underarms, making sure that not even the smallest hair remained. It didn't take long as I've never been very hairy. After drying off, I softened my legs with a moisturizing lotion, then covered my whole body with perfumed dusting powder, just Jeannie had taught me to do. She was waiting for me in her bedroom sitting on the edge of the bed. She checked me over to be sure I'd shaved well. "I want you to wear the things I choose for you, but just for today. That way I can be sure you look as good as possible the first time you see yourself as a young woman. From then on, you can wear whatever you like. All right with you?" "Sure, that's fine with me," I answered. I was so happy that she was going to let me get dressed up as adult that I didn't care what she'd selected. Besides, I knew she had great taste in clothes, so whatever she picked out for me would look good. First, she had me put on one of her pretty pink uplift bras, and then insert some foam rubber falsies she told me she'd bought just for today. With the falsies in, I felt as if I were complete for the first time. So feminine! But when I put on the matching pair of pink panties, my erection made the whole thing seem silly. Jeannie was determined she was going to do something about that problem. She knelt down in front of me and caressed my penis through the soft fabric of the panties. Just before I was ready to come, she took it out and sucked it between her lips. I lasted about three seconds before I gushed into her mouth. To both our surprises, my erection didn't disappear. She had to do it again before I finally went limp. But even after all that, the bulge in my panties was still considerable. We tried several different things to conceal it, but nothing seemed to hide this very unfeminine protrusion. Finally, after several other methods failed, much to my embarrassment she tried a sanitary belt and napkin. The belt was made of elastic, about an inch wide. She slipped it around my waist and then attached the sanitary pad to the two hooks that dangled from the belt. She tucked my balls and penis back and with the sanitary pad pulled very tightly, it turned out to be the perfect answer. I put the wispy panties on again and this time they looked like they were made for me. Not a bulge in sight! "Oh, Aunt Jeannie," I said, "I can't believe how well it works. By the time I get on all my clothes, there won't be any sign of it at all." Jeannie and I decided that, as we were going to dress me as a young woman, not a girl as we had in the past, a pink garter belt and stockings would be fun for me to wear. She showed me how to put the garter belt around my waist and then helped me put on the sheer stockings. I was amazed at how pretty my legs looked and the feeling of the stockings on my legs was wonderful! If it hadn't been that my cock was so tightly compressed by the sanitary napkin, my erection would have caused another unsightly bulge. Next, she handed me a pink slip that had a wide band of lace at the top and hem. Jeannie had learned early on that pink was my favorite color for lingerie and just about anything else. I wriggled into the lovely slip, adjusting the straps to fit. The smell of my perfumed dusting powder, combined with the soft, silky caress of all this pretty lingerie, was making me feel very feminine. It seemed so very natural for me to feel that way. She picked out a pair of black patent leather shoes with three-inch heels for me to try on. They fit perfectly, but when I tried to walk across the bedroom, I nearly broke my neck. Jeannie laughed and said she knew I'd get used to wearing higher heels very quickly. We completed my outfit with an off-white blouse and a short pleated plaid skirt. The skirt was a bit loose on me around the hips, but she told me not to worry. She would be able to make minor adjustments to many of her pretty things so that I could wear them. All this time I was becoming more excited, thrilled really. I was somewhat nervous, yet pleased at each step as we continued my conversion into a young woman. She tried several wigs on me, but all the styles seemed too adult. In the end, as my hair was rather long, Aunt Jeannie used her curling iron and did my hair in a very pleasing feminine style. We went through the whole business about makeup and jewelry. She said I'd have to learn to do this myself in the future so she'd explain each step as she went along. Putting makeup on properly, she told me, was an art. Too much makeup made you look cheap, and not enough made you look plain and unhealthy. Jeannie was an expert. By the time she was finished, I looked exactly like a very pretty young girl. My reflection in the mirror was stunning, especially to me. I had never imagined I could look as nice as I did. The makeup, the foam rubber breast pads and the grownup clothes made all the difference. We left the bedroom went into the living room as Jeannie wanted to show me a few more things about being a lady. She led me to a chair and said, "I'm sure you don't want to look all wrinkled, so when you sit down, make sure your skirt isn't all bunched up in back. You have to be conscious of how you sit as well. A lady either crosses her legs or keeps them together. Try it and see how you do." I had been watching women and the way they do things for quite a while, so it was very easy for me to slip into their role. I smoothed my skirt out in back and then slipped onto the chair. As I experimented with crossing my legs, I was enthralled with how sexy my stocking clad legs looked peeking out from under my skirt. I loved their silky feeling. When I got up, she hugged me and said, "You seem to be a natural at being a woman and you look much more like a pretty girl than I'd ever hoped for. So much so, that we'll have to pick out a name that's more suitable for the new you. Calling you Chuck would seem silly now." "How about Karen?" I suggested. "I know a girl at school by that name, and I like it a lot. I'd like to use Anne as a middle name." She knew why. It had been my mother's name and I still missed her very much. "That's a great idea. We'll start calling you Karen right away. I know your mother would be pleased. If she were here today, I think she'd be as supportive of your need to be feminine as I am. I'm very proud of you, honey. I've just got to show off my pretty niece. We've gone to too much trouble today to just sit around the house without anyone seeing how lovely you've turned out. Let's go shopping at Northland mall. That's perfect. Then we can buy you some pretty clothes of your own." I looked at her like she had suddenly gone crazy. "You've got to be kidding! I can't do that! People would point at me and laugh," I complained. "Honey, they'll not only believe you're a girl, but I'm sure once the boys see you, they won't leave you alone. Come to think of it, that might prove to be a problem. How will you feel if men pay attention to you? Are you going to like it or will it make you nervous?" "I've thought it once in a while, but I'm not sure how I'll react. I've had some dreams about meeting a man, but I'm not sure how I'd feel if it actually happened. Do you think it means I'm gay?" "No, probably not. Most people have similar fantasies. You might be bisexual, but judging from the way you reacted earlier, I'm sure you're not a homosexual. Bisexuality is becoming very prevalent these days. I found out a few years ago that I'm bisexual and so are some of my friends. So even if you are, don't worry about it. It just means all the people in the world are your potential lovers, not just half of them. What's so terrible about that?" I knew I was blushing, but I couldn't help it. Sex wasn't something I'd ever discussed with anyone before. "I guess that makes sense," I said. "I've never thought about it that way. I know women have always turned me on, but I think I fought any attraction I felt for men because all my friends hate gays so. I didn't want them to think I was one." "Most children act that way because they don't understand gays. As they grow older and get to know some gay people, they realize they're not very different than anyone else." I had to admit it was comforting to know I wasn't as strange as I'd thought I was. She took my arm and told me, "You and I are going to go shopping now, Karen. We're going to buy you some pretty things of your own. How would you like that?" "I'd like it a lot but I'll be scared to death," I admitted. "Are you sure no one would be able to tell I'm not really a girl? I'd die if anyone found out." She gave me a reassuring look. "No one will be able to tell you're not a girl because, in my opinion, you really are a girl. You think like a girl, you act like a girl and now you even look like a girl. You look more natural now than you ever did as a boy. So don't even give it a second thought. Don't you feel as if this is the real you? I'll bet you're a lot more comfortable with yourself now." "I guess I do, but I'm so nervous about going out in public in a skirt. Won't people who know me be able to tell it's me? You know how the other kids in school would treat me if they ever found out about this. I'd never be able to go back there again." Well, the flattery eventually worked and I reluctantly agreed to go. Jeannie spent a few more minutes putting the finishing touches on me. "Here," she said, "you can carry this handbag. Let's put some makeup, a brush and this wallet in it. Oh, and here's a watch for you to wear as well. What about a necklace? Would you like to wear one with that outfit?" I knew just which one I wanted to wear. "Could I wear the pretty braided gold chain you got in New York last year? I promise I'll be extra careful with it. I've always wanted to see how it would look on me." "Sure, it's in my jewelry box. Help yourself. Here, put this money in your wallet. We'll have to get you some identification with your new name on it eventually. There are so many fun things we'll be able to do now... just us two girls." We both had a good laugh at that. Her reassurances had calmed my nerves and I was beginning to enjoy myself. I knew she was right, but I guess I couldn't help fearing discovery by someone I knew. After a final check in the mirror, we left for the mall. I was still very nervous. It was a new experience for me to be outside as a girl and, as we approached the mall, I was tempted to ask Aunt Jeannie to turn around and take me home, but the thrill of being out as a girl outweighed my fear in the end. As we got out of the car I felt as if everyone was staring at me. I told Jeannie, but she said it was because I was so pretty, not because they thought I wasn't a female. She said it's something every pretty girl has to get used to. "There are so many things I want to buy for you, Karen," she told me. "I think you should have some pretty things that will be your very own, like shoes and lingerie and so many other things. Not that I mind you wearing mine, but I think every girl should have her own very special feminine things. You'll see. I know you'll love being a young woman as much as I did when I was your age. It's so much more fun than being a boy." "You're right," I conceded. "It is fun. I feel so strange, but it's a good feeling." I felt like I was in a different world. I was so much more aware of everything around me. I kept up a non-stop conversation, talking about everything that popped into my head. As we were approaching the mall, Jeannie stopped me and said, "Karen, you've been getting dressed as a girl at home for a long time. I've been watching you. You behave perfectly as a girl when you're wearing a dress. As the saying goes, you've come a long way, baby. So stop worrying. I guarantee you no one will know the difference." Walking through the mall, it pleased me to notice that we were getting many admiring glances from men. Jeannie noticed it too and asked me what my reaction was. I had to admit I loved it. Almost immediately I became more relaxed and began to enjoy the feeling of being a woman. It was fantastic! I loved how my skirt caressed my legs as I walked, and the clicking of my heels sent chills up and down my spine. Maybe it was the novelty of the situation or the fact I also felt more grown up as well. I didn't know why for certain, but I truly loved being a girl. So many men stared at me and I could see desire in their eyes, and that thrilled me sexually. It really did. Jeannie and I had a great time shopping for my new wardrobe and trying on clothes. We went into almost every store in the mall. I spent at least a half hour trying on lingerie at one of the better department stores. I didn't even get too nervous when one of the saleswomen walked in on me. All I had on was my bra and panties. She clearly didn't think of me as a boy. Luckily, my sanitary napkin hid the bulge in my panties perfectly. She just handed me a nightie to try on and then walked out. We stopped at Jeannie's favorite shoe store and she bought me four pairs of shoes there. There was a particularly cute young salesman in the store who waited on me. He became friendly very quickly. I was amazed when I discovered that he was trying to look under my skirt each time he helped me try on a pair of shoes. That made me very nervous, but I knew I was also flattered. I did purposely cross my legs a few times and I'm sure he liked what he saw. I had to choke back a laugh. Wouldn't he be shocked if he knew what was really inside those lacy pink panties he was sneaking a look at! I must admit I even flirted a bit with him. Aunt Jeannie watched all this, trying to hide her laughter. While she was paying for the shoes we'd bought, he asked me for my phone number. I was tempted to give it to him, but I knew I couldn't. Karen's Story When we left the store, I told her what had happened. She teased me about having made my first conquest and told me I should have given him our phone number. This time she had a huge laugh when she saw the horrified look on my face. "You can't be serious," I replied. I couldn't date a boy. What would I do if he wanted to kiss me, or worse, if he wanted more? I'd be in big trouble." "Look, Karen, you're going to spending a lot more time as a girl and if you think you'd like to date, it's certainly fine with me. There's no reason you can't. You can kiss and go as far as you like, as long as you don't drop your panties. Your breasts are not any smaller than a lot of other girls your age. A boy would never know the difference, believe me. As I recall from when I was a teenager, they're so happy to get anywhere at all, they don't even realize what they're doing. So relax and enjoy being a girl, will you please? I won't let you get into situations I don't think you could handle." I was sure it would take a giant leap for me to adjust to being with a boy, but knew I would eventually like to. "I guess you're right, but I think it'll be a long time before I could date. It's not that I don't want to, but I don't think I could relax enough to enjoy myself. There's so much I need to learn first." "I'll teach you all you need to know about boys, honey. They're so eager to get you in bed, it makes it a very simple matter to control them. Any girl with brains has no problem at all. I want you to be just like any other girl, that is if you truly want to be." "Oh, Aunt Jeannie, I do. I really want to be a girl, in every sense of the word. I know you're right about boys, so if you'll teach me, I'll be a very willing student. Do you actually think it's possible for me to date?" "Karen, you'll not only be able to date, but after I get through teaching you a few tricks, you'll have them eating out of your hand. You're now a beautiful young woman. It'll be easy for us to make you one of the more popular girls in town. Believe me, I know what I'm talking about. Your mother taught me all I know about men and she had a very special knack with them. You may have even inherited her talent." We continued our shopping, stopping at the discount pharmacy to buy all the necessary feminine things I'd need if I was going to be spending a lot more time as a girl. We bought makeup, nail polish, shampoo, hair spray, big pink hair rollers, perfume and bath powder, a blow dryer, two more boxes of sanitary napkins and six more of the wide elastic sanitary belts. I'd never realized how many different things a girl needed to make herself pretty, but I was learning very fast. Next we stopped and had a bite to eat at the restaurant in one of the big department stores. We both ordered a crab salad plate and iced tea. Again I had time to practice my ladylike manners. I made sure I kept my legs demurely crossed and tried, as best I could, to copy Aunt Jeannie's other mannerisms. Jeannie must have noticed my efforts. She reached over and touched my hand. "I see you're being conscious of how you eat. Make sure you take nice little ladylike bites. This is part of your education as a young woman. You've never had the opportunity to learn a lot of things other girls your age have known for years so I'm going to make sure you have a chance to discover them, that is if you want to." "Oh, yes, please, Aunt Jeannie. I want to be as much a girl as anyone else. I promise to be the best student in the world. I know I've got a lot to learn, especially about boys, so whenever you think I need to know something, please tell me." "I will, and I'll try to make sure you know all about boys before too long. I've got the feeling you're going to need learn quickly, judging from the looks the boys have been giving you today. You really are a very pretty girl, and I'm not just saying that because you're my niece." At that I blushed, not knowing how to handle flattery, but loving it all the same. After we had eaten, I realized that I was in very serious trouble. I had to take a pee. When I finally mentioned it to Jeannie, she just smiled. "Come with me," she said, smoothly and quite casually. "I have to go myself." When I realized what she was suggesting, I was horrified. She laughed at the expression on my face and as we walked toward the powder room, and she told me something that was to become quite important to me. "You're a girl now," she said, "so when nature calls, you'll just have do the same thing the other girls do. You'll learn." "You can't mean I should use the ladies' bathroom," I stammered. "I'd never be able to walk in there. I'd faint, I know I would. Please, let's just go home before I burst." "Karen, I've told you at least a dozen times today you can do anything, go anywhere you want. Absolutely no one is going to realize you're not completely female without seeing you in the nude. You've got to stop being so paranoid. Now follow me. I have to go too, so let's just get it over with." "Ok, but I want you to know I'm scared to death," I admitted. "Please let's get in and out of there as fast as we can. From now on, I'm going to make sure I go before we leave the house." As we entered the powder room I began to tremble and, while I had a smile on my face, it felt like it was pasted there and wasn't working too well. There were several women standing in the outer room, but Jeannie and I ignored them and went into the room where the facilities we needed were. There were several toilets in little stalls with the door that could be pushed closed. I ran into one of the empty stalls, locking the door securely behind me. I hung my coat and purse on the door hook, then used some paper to clean off the seat. I quickly lifted up my skirt and slid my panties down as far as the tops of my stockings. I carefully sat down, all the time watching the door to be sure no one was spying on me. When I was satisfied that no one was watching, I slipped my cock out from under the sanitary napkin and quickly peed. What a relief! When I'd finished, I patted myself dry with some paper, then pushed my penis back under the napkin, feeling so much safer with it hidden. I stood up, pulled up my panties, again being thrilled with feeling so feminine. I dropped my slip and skirt back into place after adjusting my stockings. Finally, I sensed I was gaining some self assurance. I thought about how no one had given me any strange looks all day. On the contrary, all the looks I'd received had been very flattering. I decided Jeannie had been right all along. I'd been silly to doubt my appearance. As I'd been warm all day wearing my coat inside the mall, I now decided I'd carry it. Before I'd felt too self-conscious to take it off. It was, I decided, time to be brave. I was starting to enjoy myself for the first time that day. I was now a real girl. I knew it, no one else seemed to doubt it, so I might as well enjoy it. What a phenomenal feeling! I strolled out to the mirrors and checked out my appearance, just as most of the other women there were doing. What a pleasant picture. I loved my feminine reflection. I couldn't remember any time in my life I'd ever felt better. I fussed a little with my hair, then went and sat in one of the chairs to wait for Jeannie. It was even fun just sitting there, crossing and uncrossing my legs, feeling the slippery smoothness of my stocking clad legs as they rubbed against one another, and it was especially wonderful that there was no longer any ugly bulge to get in the way. How I loved being a girl! I noticed how nicely the room had been decorated. The walls were papered with soft pink flowers on white background. The carpet and chairs were a light gray. So pretty and so unlike the men's rooms I'd been in. When Jeannie finally came out, she immediately noticed me sitting there looking like the cat that had eaten the canary. She gave me a radiant smile and, when she's finished washing her hands, we walked out together. "What's come over you, Karen?" she asked. "You're acting like you own the world now." "I guess when I had time to think about what you've been telling me, I realized how right you were. No one all day has treated me any differently than they treated you. I just love being a girl and now I think I finally beginning to relax and enjoy being Karen. Thanks for being so helpful, Aunt Jeannie. I want you to know I love you, and I really appreciate all the effort and expense you've gone to. You're the best friend and the best aunt anyone ever had." I could tell she was pleased. "You're a very good nephew as well. Whoops, I better make that niece in the future." We both laughed at that. We continued our shopping, buying me all the pretty things that Jeannie had promised. I had such fun picking out a whole new wardrobe. All the pretty lingerie, dresses, jewelry, shoes and hosiery. I was in seventh heaven. I guess the main reason we stopped shopping was that we couldn't carry any more boxes. By the time we arrived home, I was dying to get into the house and try on all my pretty new things. Jeannie and I carried everything into my bedroom. I couldn't believe all the boxes and bags. It was going to take hours just to put everything away, much less try them on. Jeannie left me to play and experiment while she went and started dinner. We had a fabulous meal, special because Aunt Jeannie felt this had to be a extraordinary day for me. She let me have wine with dinner and we just sat at the table when we were done, drinking coffee and talking, reliving our day. "Karen, honey," she said, "this truly was a terrific day. You know, I feel as if you've been a girl all along. I guess I'm more comfortable with you as Karen than I ever was with Chuck. Somehow you never seemed at ease with yourself or with me before. Are you happier now?" "I know I'm happier," I answered, quite honestly, "but today has given me so many things to think about. I'm a little scared about the future. Do you know what I mean? If I'm really more female than male, I'm going to have a lot of problems to solve. I'm going to need your help now more than ever." "You know I'll always be around to help you," she said, "so don't worry. We'll work everything out, you'll see. If you decide you want to be a girl all the time, then we'll simply register you in another school as Karen. That will be easy. I know people who can get any kind of identification we'd need. If you're sure at some point that you'd like to consider a sex change, we'll explore that possibility, too. So why don't you just relax and enjoy being your new self." "I will," I explained. "It's just that I just need some time to get used to all these changes and to learn more about being a woman. Once I do, I'll have to think more about what the future holds." "That's the idea. Now scoot. Go and try on the rest of your new clothes. It's already late, so you'll have to hurry if you want to finish before bedtime." I didn't need any more encouragement. I went to my room and spent the next hour or so trying on the rest of my new outfits, rushing back into the living room and modeling each of them for Aunt Jeannie. All in all, we had bought six dresses, four sweater and skirt combinations, seven blouses, two pairs of pants, six pairs of shoes, two blazers, a coat, three handbags, five bras, twelve pairs of panties, three full slips, a half slip, a camisole and matching tap panties, a gorgeous pink silk teddy, two garter belts, three nighties, six pairs of pantyhose, four pairs of stockings and all kinds of scarves, jewelry and makeup. Parading around in front of Jeannie in all my new fashions was, to me, the perfect end to a perfect day. Everything seemed to fit well, except for a skirt which needed shortening. Jeannie told me I should wear short skirts because, when a girl has legs like mine, she should show them. Gradually I was learning the feminine art of walking in high heels. I was also learning how, with many suggestions from Jeannie, to properly accessorize my outfits. What jewelry for dressy occasions, how to coordinate shoes, or what shade of eye shadow went with each color and style. The last thing I modeled was my new very sexy peach negligee with matching bikini panties. Jeannie insisted I keep it on. "Karen, I'm not ever going to let you sleep in anything other than a pretty nightie," she said as I twirled before her. "I always hated those pajamas you used to wear. You look so cute now. Do me a favor and throw out all those pajamas tomorrow." I went over and gave her a hug. "I will, I promise. I hate them, too. Please don't ever make me wear any of those dumb clothes again. I know I'll be much happier as a girl, you'll see." She held me in her arms and said softly in my ear, "I already know that. I just love the way you feel in this nightie and your perfume smells so good." Her hands moved down my back, gently caressing me through the silky fabric until she reached my panties. She slipped her hand inside the waist band, softly kneading my buttocks. Even though I was tired, I immediately became erect under the sanitary pad. I pressed my pubic bone into hers, lightly kissing her on the neck. "Karen, it's about time you learned more about women. I'm going to give you some first hand experience on how a woman makes love. Give me just a moment to change into my nightgown, then we'll get in my bed. I'll show you how a woman likes her loving. Do you think you're ready for that?" I just shook my head, letting her know I was willing. I was too excited to talk. We went into her bedroom, turned down the bed and then I got in. Jeannie slowly undressed, knowing very well that my eyes never left her for a moment. She unzipped her dress and let it fall to the floor. She slid the straps of her slip off her shoulders and let it fall around her ankles. The sight of her in her bra and panties almost made me come. She turned toward me as she reached back to unhook her bra. Her bra slide down her arms and she smiled at me as I stared at her breasts. They were perfect, not too large and perfectly shaped. Her nipples were as erect as my penis. I couldn't wait to touch them. She walked over to her dresser, wearing only almost transparent pale yellow panties, and got out her nightie. Then she came over to my side of the bed, laying the gown on the bed next to me. "Karen, I want you to finish getting me ready for bed. Take off my panties for me and then help me get into my nightgown. I think you should pamper me a little tonight. After all, we spent the whole day doing things for you. Now it's my turn." "Oh, Aunt Jeannie, I always would do anything for you, but after today, I want to spoil you forever. You just tell me what you want and I'll do it, anything at all." "Just get me undressed and into my gown. I can tell you're still wearing your sanitary belt and pad. You can take them off. We're going to be putting your penis to work shortly, so let it out of its cage." I got out of bed and stood next to her. My heart was pounding. Although it seemed as if my arms were made of lead, I finally managed to move. She just stood there, smiling. I took hold of the elastic waist band of her panties and slowly slid them down her legs. I knelt in front of her as she stepped out of them. I looked up to see her vagina a few inches from my face. I moved forward and kissed it, feeling her slit against my lips for the first time. The smell of her sex was addicting. It was all I could do to stand up and put her nightie on her. My cock was very hard by this time, so I was glad to be able to take it out from under the sanitary napkin. I pulled my panties back up, barely covering my erect penis. The feel of the fragile silky fabric against it sent shivers through me. I got into bed, letting Jeannie take the lead. She immediately took me in her arms, kissing me and delicately exploring my body. My hands roamed over her. I was amazed at her softness and suppleness. Our bodies pressed together, her hips slowly rocking her mons against me. I took her breast in my hand, feeling the stiff nipple. What wonderful things breasts are. How I wished they were mine! "Karen, I'm going to make love to you now. I want you do as I tell you, and if there's anything you don't understand, ask me. If there's anything you'd like to try, we'll do it, but not now. Tonight I want to teach you all about my body and yours, how a man pleases a woman and how a woman pleases a man. You're going to have to learn both. Someday you may want to be able to please a man yourself." With that, she kissed me again, slipping her hand down to stroke my erection through my panties. She had learned earlier how much I loved that. I needed no encouragement to follow suit. I trace her cunt lips with my fingertips, trying to remember her response to each caress. I wanted so badly to turn her on as much as she turned me on. She finally sensed I was getting too excited. She slipped my panties down, then lowered her head and softly nibbled at the tip of my hard on. "I want you to get on your back and then just relax. I'm going to get on top of you and put your penis in my vagina. Don't do anything. If we don't go slowly, you'll come right away. That's not what I want. I hope to keep you erect for a long time." She placed me as she wanted, then straddled my hips. Very slowly she lowered herself on to my cock. As the tip touched her lips, I fought to control myself. It was incredible! When she'd finally inserted it all the way in, all my attempts at control weren't enough. I came and came, the throbbing seeming to concentrate all sensation in my cock and balls. But fortunately I didn't lose my hard on. She stopped for a few minutes, leaving my cock inside her, and then went right at it again. This time I lasted for ten minutes and Jeannie was able to have several intense orgasms. "Honey, you're a fast learner," she said. "We'll rest for a few minutes and then I want to teach you how to please a woman orally. It's the best way to make sure a lady enjoys herself, so I want you to be good at it. It's one of my favorite forms of sex. The best part about it is I can get satisfaction from either a man or a woman. I bet you'll learn to love it as much as I do." By now I was relaxed enough that I felt comfortable asking her a question. "It felt so nice down there, especially when we were making love. Does it tastes as good as it feels?" Her response was completely honest. "I think it does. I've always loved the taste of a woman's sex and I love how it turns a woman on. I love the way a man tastes, too. Their cum has a salty taste to it. I think you'll learn to like these tastes as much as I do." Our rest period lasted about five minutes. Jeannie starting licking my soft cock and in no time my erection reappeared. She took of her nightie and taught me how she liked her breasts sucked and massaged. Then she had me slowly kiss my way down until I reached her pubic mound. I spent a few minutes there, then moved straight down to lick her cunt lips. She was right. The taste was super. She coached me on just how she wanted it done. She told me the names of the different parts of a woman's organs. I'd never even heard of a clitoris before that night, but I was an expert on hers by the time it ended. I loved pleasing her. She'd been so wonderful to me that I was more than willing to reciprocate. We fell asleep in each other's arms, sleeping like newborn babes. I dreamt all night about being a woman. What a day for me! My first official day as a girl and my first time making love to another woman. Yes, that's what I said, another woman. By that time I felt very strongly that nature had truly intended me to be a woman and that I probably would think of myself that way for the rest of my life. Karen's Story Chapter Two - Becoming a Girl The next morning we got up around eight. Jeannie and I showered together and then went into her room to get dressed. "Karen, today I want you to pick out your own clothes. I don't want you to get used to me doing it for you. You've got to develop your own sense of style. Experimenting with different outfits is the only real way to do it. You're welcome to wear anything of mine or any of the new clothes we bought you yesterday. I'll make an occasional comment, but if you disagree, then you do what you feel is best, ok?" I was anxious to get into my pretty clothes once again but I took time to consider what Jeannie was saying. "I'm going to need all the help I can get for a while, so please let me know if there's something you see that doesn't look right. I want to look as good as I can and until I learn all the things a girl needs to know, I'll probably make a lot of mistakes if you don't give me hints." "You've been wearing girl's clothes for a while now," she answered, "so just go with your instincts. You look very pretty when you take the time to get all dressed up. I think you know more about being a girl than you realize. Have you decided what you're going to wear today?" I'd been thinking about it all morning and, after considering just about every possibility, I finally made a decision. "I guess I'll wear my new red sweater and red plaid pleated wool skirt. If we go shopping again and I'm going to be trying on clothes, wouldn't that be easier to get in and out of than a dress?" "See, you're thinking like a girl already," she smiled. "You're not going to need much help from me at all. That's my favorite of all the things we bought yesterday. You look so pretty in it, Karen. Hurry up and get ready. We're going to have another incredible day today, I can just tell. It's so nice to have a girl friend to do things with, don't you think?" She laughed when I blushed at the thought of being a girl and being her friend. God, being a female was so terrific. I don't think anything could have made me unhappy that day. I went into my room to get dressed. I began by tucking my privates under a sanitary napkin. I pulled it tight to be absolutely sure nothing at all would show. I picked out a pair of white bikini panties with lace around the waist and leg openings and the matching bra which also had pretty lace insets. With my breasts pads in place, I once again began to feel like a true girl. I decided to wear beige pantyhose and, as I had learned to love full slips as much as Jeannie did, I selected a white one with matching lace. Aunt Jeannie helped me with my makeup and hair. She also gave me a manicure, then painted my nails with a shade of polish called "Passionate Red." I was thrilled! I couldn't stop looking at my nails. She finally rushed me off to finish dressing. I removed all the tags from my new sweater and skirt and carefully put them on. Lastly, I put on little pearl earrings, my watch and a bracelet, then just a hint of perfume. I was very cautious as I didn't want to risk ruining my pretty nails which were not completely dry yet. Jeannie found me in front of the mirror, staring at my reflection, as usual. I knew I'd never tire of seeing myself as a woman. We spent an hour or so sitting around the breakfast table, discussing yesterday's events. Jeannie was particularly interested in my reactions to having spent the day as a woman. "You seemed to be more at ease," she said. "No typical teen-age hostility about having to spend time with your aunt. You know, like the way you used to act. As a boy, you're very quiet and unsure of yourself, but you seemed different when you became Karen. You talked to me like any other adult would. You appeared to be more comfortable, even with yourself." "I was very nervous at the start," I said, "but as soon as I realized people didn't take me for anything other than a girl, I relaxed and began to enjoy myself. I liked the way men stared at me and the attention I got from the salesman in the shoe store. But I guess I'm confused about why I enjoyed it so much." Jeannie looked at me for a moment, as if deciding whether she should tell me what was on her mind, then replied, "I've always sensed a lot of femininity in you, even at an early age. I thought it was better to encourage what was natural in you rather than try to force you to be something you weren't, so I gave you every opportunity to express that side of your personality. The reason I think you enjoyed yesterday was because you finally accepted that this is the real you. If you agree with me and want to continue to explore, then I'm more than willing to let you develop your female side as quickly as you want." I had to admit I'd never been very happy as a boy. I was much smaller than the rest of the boys my age and very quiet, so they teased me a lot and rarely allowed me into their group. I spent most of my time playing with the girls in the neighborhood. I guess I liked playing with them better anyway, and they always treated me as one of them. I know there had been times I wished I'd been born a girl, but would rather have died than admit that to anyone. That is, until now. "I guess that's why I was always happy when you allowed me to wear girl's clothes," I admitted. "I've even worn panties under my clothes at other times. I love the way they make me feel." I could feel myself blush as I admitted that to her. She laughed and told me she'd known it all along. "The reason I took so much time and effort yesterday was to let you experience being a real girl. I think you're old enough to begin making some decisions for yourself. If you want to try living as a girl, then this would be the perfect time to start. You're just about to graduate from grammar school, and if you decide to be Karen all the time, then all we'll have to do is to switch school districts and register you in high school as a girl. You don't have to make up your mind yet. We've still got about six weeks left before registration. Think about it for a while, and we'll discuss it again before then." The prospect of living as Karen enchanted me, but to be honest, it also scared the heck out of me. It meant becoming another person and committing to a completely different way of life. "I think I want to try it, but first I need to know what you'll expect of me. Does that mean I have to remain Karen for the rest of my life? And what about if I meet somebody and get serious? There are so many things to consider." Jeannie reached over and took my hand in hers. "You can always be anything you want as far as I'm concerned. If you find being Karen is not what you want, then we'll try anything you feel might be right for you. And as far as the opposite sex goes, if you're a girl I'd expect you to act like any other girl and date the boys you go to school with. It's up to you to tell someone you care about whatever you feel is right for the two of you. Just remember, I'm completely open to anything you want to try. As long as you're happy, that's all that really matters." "How about if we try it for the next few weeks," I said, "and if I like it and want to continue as a girl, then we can register me in school as Karen." "Then Karen it will be," she smiled, "at least for a while. Let's get the dishes out of the way so we can begin working out all the details. This is going to be fun! I don't think we'll have any problems with the people in the neighborhood. They're all so snobby. They never take much notice of us anyway. If someone asks, I'll say my nephew went to boarding school and you're my niece from upstate who's come to live with me. I refuse to sneak around. We're going to go wherever we've been going. You look so different and so much more mature as Karen, I'm sure no one will ever recognize the old you." As we were determined to finish all the shopping we hadn't completed the day before, we hurried through the dishes and then drove off to the mall. We arrived at the mall just as it was opening. Jeannie felt positive we'd finish all our shopping that day. She wanted me to be able to settle in as Karen and she thought it would help if I had my own wardrobe. "Karen," she said, "if you see something you'd like and it's not on our list, be sure to tell me. We've got plenty of money to spend and I want to get as much as we can today. Once all this shopping is out of the way, we can concentrate on completing your training to be a young lady." "Ok, I'll tell you if I see something. I guess I won't be sure of everything I'll need until I get some more practice though. What more do I need to know right away?" "Honey, you got to learn more about makeup and more about doing your own hair. If you like, we can let it grow longer. It's a nice length now, but most girls your age have longer hair. Besides, I think it'd be cute. Many boys these days have long hair, so I don't think anyone will say anything about it if you decide not to dress as Karen. We can even get your ears pierced." "Also," she added, "I want you to take some time every day to experiment with clothes. I'll get you some fashion magazines and they'll give you some ideas, but you should also look at what other girls your age are wearing." "Oh, I'd love to let my hair grow," I answered excitedly, "and it'd be fun, especially getting my ears pierced. Please don't think I'm silly, Aunt Jeannie, but I'm so happy when I'm Karen and wearing girl's things." "What's silly about that? I loved being a girl when I was your age and I still do. Half the fun of being a teenager was dressing up in new clothes or reading about them. The other half was talking about boys with other girls my own age. You can do that once you make some friends as Karen." "Do you think I'll be able to, Aunt Jeannie? It's so hard for me to believe I can pass myself off as a girl that well. I don't know what I'd do if someone realized I was really a boy and then told everyone I know about it. I'd just die of embarrassment." "Karen, you're as much a girl as I am. How many times do I have to tell you that you look and act just like any other girl. All you need is to develop some self confidence. Don't worry, it'll come in time and then you'll have as many girl friends and boy friends as any girl your age." Well, I guess I had to believe her. No one had treated me as if they were aware of my being different, so they must think of me as a girl. I know I was beginning to think of myself that way. We continued with our shopping, buying a robe and more pretty lingerie. Jeannie insisted I buy one very dressy dress. I finally found one at Nieman-Marcus. It was a beautiful shade of pale rose eyelet lace, with cap sleeves, a scalloped neckline and a full skirt. I felt like a princess in it. Once I had it on, I didn't want to take it off. We went to the cosmetics counter and the saleslady showed me what makeup would look best for my complexion and skin. She showed me how to apply it and how I should change it for evening wear. She was so wonderful to me. Aunt Jeannie said she had even learned a few tricks. Next, we went to the junior sportswear department, where, much to my dislike, Jeannie insisted I buy some more pants in addition to some of the skirts and blouses I'd already selected. She said all girls my age wear pants, usually jeans, so I had to wear them occasionally, just so I'd fit in. I hated them, but I knew she was right, so I picked out jeans and one pair of dressier pants. After that, we went to the shoe department where I bought some dressy shoes to wear with my new dress and some casual shoes for everyday. We finished up at one of the jewelry boutiques where I bought some necklaces, four pairs of earrings and two rings. I also had my ears pierced. It was too early to go home, so we returned to the tea room where we had had lunch yesterday and then, after going to the car to lock up all our packages, we took in a movie at the theater in the mall. It had been another great day for me. I'd spent it totally as a girl with no one wondering if I was a male. We'd spent tons of money on a new wardrobe for me. I'd can't remember ever having been more excited. When we returned home, I held another fashion show for Jeannie, this time behaving like the models I'd seen on television. I swirled, trying to look sophisticated. I acted so outrageously that she was in tears by the time I'd finished. "Karen," she said between bursts of laughter, "you really were meant to be a girl. I've never seen you so happy, or so comfortable with yourself. You used to act like such a child when you were a boy. Now, you don't act any differently than most of my friends. You've grown up in one weekend and come out of your shell. I want you to stop thinking of me as Aunt Jeannie. Let's just pretend we're girl friends, not aunt and niece, Ok?" That made me stop and think. "You mean you'll treat me like a girl friend, rather than a niece? That's fine with me. I feel like we're friends already." "I want us to continue as we started this weekend," she said, "as equals. You'll learn about being a girl faster that way and we can share a lot more time if we're friends. I'll teach you all the feminine wiles and show you how to act around men. Would that please you?" "It guess it would, but I know I'll be very embarrassed, so you'll have to be patient with me. I know if I spend most of my time as a girl, I'll need to know more about men. It's just that I'm still a little tense about having any kind of relations with a guy. I think I'd like to try it, but yet I'm afraid of what it means." "I understand what you're saying," she answered. "I won't push you into anything you don't feel comfortable with. I'll just teach you what you need to know if you decide you want to date men. You're more girl than boy now, or so it seems. It would only be natural for you to date men. Besides, do you remember what I told you about being bisexual? Many people are these days. It's nothing to be ashamed of." "If sex with men is as fun as it is with you," I said, "then I'm sure I'll try it. You make me so horny, even though you're female and I feel I am too. So maybe it doesn't matter to me what a person is. Is it as much fun with a man?" "You'll love dating as Karen, I'm sure of it. It's great fun to have a man fuss over you and buy you presents. Being pampered is one of the best parts of dating, but I'm sure you'll find sex with a man just as wonderful. Just try it a few times and if it doesn't turn you on, then you can try some alternatives. But whatever you do, don't knock it until you've tried it." I had to admit she was making sense. "I guess it'll be fine once I learn how to act. Do you think boys will really want to date me?" "Honey, when you get prettied up like you did this weekend, you're as beautiful as any other girl, really you are. Please don't think I'm saying that just because I love you. It's absolutely true, I swear it." I knew from my many trips to the mirror that I wasn't too bad looking. I knew men liked my appearance from the looks I got at the mall, but I couldn't quite believe I was beautiful, in spite of what Aunt Jeannie said. I decided I'd work hard to make the best of what I had. I'd learn all about makeup and clothes and I'd listen very closely when she taught me how to act around men. Maybe then I'd be able to find someone who liked me. The rest of the day we spent talking. She gave me tons of tips on being a lady, taught me how to act around men, especially on a date and told me many funny stories about her dating days. We'd never been so close or spent so much time talking to one another. I guess we both loosened up once we had things in common to discuss. The next seven weeks flew by. We went everywhere together and quickly became close friends, and I was more comfortable as Karen with each passing day. We both knew after about the first week I was truly meant to be Karen. So somewhere in the second week we sent a slightly altered record of my grades (we only had to change my first name) to the high school I'd be attending in the fall. Jeannie had called there earlier and was assured I'd be accepted for September. The next day she called a close girl friend of hers who was a doctor. She explained that her niece Karen from Cleveland had come to live with her and would be starting high school in the fall. She said as I was extremely shy and couldn't bear to get undressed or shower in front of the other girls in school. It would be a very traumatic experience for me if I had to take gym classes. Her friend was very understanding and agreed to send a letter that would get me excused from gym classes, but only if Jeannie would promise to get a professional to help me with my problem. Jeannie assured her she would. When she hung up, she laughed and said, "If you had to shower with the other girls, I'm sure it would be more traumatic for them than it would be for you. You'd probably love it." "By the way," she continued," I've got a surprise for you. I decided last week that we needed to redecorate your room, so I ordered new furniture for you. Also, there's a new carpet coming and a man will be over today to put up new wallpaper. All those boy's things in there looked ludicrous. But that's all I'm going to tell you about it. We're going out to lunch and a movie and when we come back, I was promised all the work would be done." "Oh, Aunt Jeannie," I said. "You're so good to me. I swear I'm going to work very hard in school so you'll be proud of me. Thank you, thank you, thank you!" I ran over to her a gave her a hug. God, I was so lucky! We went to the movies, but I don't even remember what the film was about. When we left the theater, I ran to the car. "Come on," I shouted, "I can't wait to get home." I let out a squeal of delight. Jeannie looked at me with obvious pleasure in her eyes. As we drove home, she reached over and held my hand. "Karen honey, every day I'm more sure we're making the right choice. You were meant to be female, I just know it. In the last month you've almost caught up for a lifetime of not being a girl, and you now act like every other teen-aged girl I've ever met, even to that squeal of excitement you let out a few minutes ago. I'm so happy for you and I know you're a lot happier, too." As we pulled into the driveway, I saw the decorator from Sampson's, a local furniture store, standing in the doorway. She was a very pretty, petite blonde, somewhere in her early thirties I guessed. She waved and told us everything that all the work had been completed as promised. I began to run into the house, dying to see what my room looked like, but Jeannie took me by the arm. "I know you're excited sweetie, but that's no excuse for not acting like a lady. I want to introduce you to Mrs. Brooks. Joan, this is my niece, Karen." I made myself slow down and be polite. "I'm very pleased to meet you, Mrs. Brooks. Thank you so much for helping with my room." She gave me a warm smile. "I'm very glad to meet you, Karen. You're just as pretty as your aunt said you were. But you don't have me to thank for your room. It was all your aunt's idea. I hope you'll be very pleased with it." Sensing that I couldn't hold back any longer, Jeannie released my arm and said, "Let's go see what it looks like. I'm almost as excited as you are, Karen." I rushed in and, when I finally saw what had been done, I was beside myself with joy. I couldn't believe it. It was beautiful, like something out of a dream. More beautiful than I could have hoped for! There was a double bed with a canopy, a matching triple dresser and a lighted makeup table, all made of maple. The wall-to-wall carpet was a pale shade of pink and felt like it was a about a foot deep. The walls had been redone with a flowery pink and green wallpaper. The bed was covered with a white eyelet spread and the windows had white curtains that matched the bedspread.