("`-''-/").___..--''"`-._ `6_ 6 ) `-. ( ).`-.__.`) (_Y_.)' ._ ) `._ `. ``-..-' _..`--'_..-_/ /--'_.' ,' (((' (((-((('' (((( K R I S T E N' S C O L L E C T I O N _________________________________________ WARNING! This text file contains sexually explicit material. If you do not wish to read this type of literature, or you are under age, PLEASE DELETE THIS FILE NOW!!!! _________________________________________ Scroll down to view text -------------------------------------------------------- This work is copyrighted to the author © 2010. Please don't remove the author information or make any changes to this story. All rights reserved. Thank you for your consideration. -------------------------------------------------------- The Tomboy Tapes by Karen Elizabeth L. (address withheld) *** One day I was reading a newspaper and suddenly found myself drawn to an advertisement for girl's clothes. I stared at that page for five minutes straight and when I was finally able to put it down I had an overwhelming urge to put on some of my sister's clothes! Luckily no one was home and I quickly raced upstairs and threw open the door to Cindy's closet. There, pushed to the back I saw what I wanted, a simple, pink mini-dress that Cindy had worn once when dad took us out to celebrate a promotion at work. I grabbed the dress and quickly ran back to my room and locked the door. (m-teen-cd, fetish, tg) *** It was going to be another one of those mornings at the breakfast table, I thought as my mother and sister began arguing. "Why can't you dress up a little bit for school Cindy," Mom sniped. "It wouldn't hurt you to look a little more like a girl now and then you know!" "I look like most of the other girls mom," Cindy replied in between bites of toast. "The days of wearing dresses and heels to school went out with hoop skirts! Do you want me to look like some kind of freak?" "I just want you to look your best that's all," sighed mom. "I want everyone to see what a pretty daughter I have!" "You're sweet mom," Cindy smiled as she chugged down her juice. "Sweet but so old fashioned!" As Cindy ran out the door mom had already turned her attention to poor dad , hounding him about Cindy's looks and grades. "She could do much better in school if she were motivated, I know she could be getting A's and B's instead of the C's she gets now. If I could just find some way to motivate her to dress better and work harder." Mom lamented. "I understand dear but I can't suggest any new ways to motivate her either," Dad was just as upset as she was but Cindy remained cool and calm no matter how hard they tried to change her. Sometimes it seemed as if they were pushing a big mound of Jell-O, but that couldn't be right, I thought, Jell-O could be molded! Several weeks later I saw Cindy dumping several cassette tapes into the garbage then trying to cover them over to prevent their being found. "I've never seen you work so hard Cindy," I joked walking into the room. "What's up?" "Motivational tapes," She sneered as she mixed up the trash. "A little present from mom and dad. They figure that if I listen to them I'll work harder in school and it'll even spill over into my home life. I sort of hate to disappoint them but they're not brainwashing me into becoming some little "Goody Two Shoes!" "Hold on a sec, I've heard a lot about those kinds of programs and they're supposed to be really helpful! Why not try them and see, what can it hurt?" I asked eagerly. It wasn't so much that I was eager to help Cindy, more that I saw a chance to be a real pain in her side! Cindy shrugged and pointed to the trash. "If you're so thrilled about them, help yourself, have I mentioned lately that you are such a suck up?" She called, leaving the room. "But a well motivated one!" I laughed as I cleaned off my newly acquired treasures. Here was a golden opportunity to show Cindy up, I'd just listen to the tapes myself and when our parents see my report card I'll tell them about the tapes! I put them in the back of one of my desk drawers so that mom wouldn't accidentally run across them, no point ruining my own surprise! I put the tapes on before going to bed but even with the volume nearly all of the way up I had to listen intently to hear anything then closed my eyes and went to sleep. The next morning I tried my best but just couldn't remember much about the tape. I did know though that it had been a very sound night's sleep and that I was feeling very refreshed and anxious to get started! "You're looking good this morning Jim," commented dad. "Ready for that big test today? You need an "A" to pull your grade up for the year you know. " "Studied all evening dad," I smiled wondering what kind of an edge I'd get from that tape I had listened to. "I can't wait to take it!" "That's wonderful Jim," Mom said as she gave him a hug. "I'm sure you'll get an A!" "Suck up!" Scoffed Cindy as she came into the room. I just smiled and stuck my tongue out at her, I enjoyed being mom's favorite and I wasn't going to start an argument with Cindy at breakfast, that was mom's job! Mom started up right on schedule. "How were the tapes Cindy, feeling more motivated today?" "They were great mom, I can't wait to get to school!" Cindy shot a quick look at me to see if he'd give her away. We both knew the only motivation for her to get to school was to see her friends but I'd keep quiet for now! "Gotta run, nice chatting!" She called on her way out the door. Mom smiled broadly, "I think they're starting to help her already," she told dad. "I can't wait to see her report card! This is going to be a turning point in her life, I just know it will" "Yes dear, I'm sure they've helped," he mumbled through his newspaper. "What was that about her report card?" "Go back to your paper dear," Mom said with an exaggerated sigh. "I'll let you know when your daughter makes the Honor Roll!" "Betcha I get there first!" I offered as I took small bites of toast and sipped at my juice. Somehow I just wasn't in my usual hurry to gobble down breakfast, must be that tape calming me down for the test today, I thought to myself. Mom smiled sweetly and patted me gently on the back. "We're sure you can make it dear, it's Cindy we're worried about. Of course with those tapes she may just pass you up!" "Fat chance mom," I was suddenly defensive. " Cindy will never be as good as me so passing me up would be a fantasy!" "Give your sister a chance Jim," Dad suddenly put down his paper. "You'll feel awfully silly if she beats your grades so don't start gloating." "Stupid too." I mumbled under my breath. Dad took a swipe at me with his rolled up paper. "I heard you, now shut up and give the girl a chance. We went through a lot of trouble getting her to listen to those tapes and we're expecting to see results." "All right, I'll keep quiet," I replied as I sulked out the door feeling very let down. "But don't expect too much, we all know there isn't that much to work with!" I wanted to add; "Especially since she's not even listening to them He thought to himself," but I'll just bide my time! "Thanks for not giving me away at breakfast," Cindy told me later. "That was very sweet of you." "I didn't do it for you," I insisted. "If I gave away the story mom would've taken the tapes away from me and I want to keep them." "Hey I don't care either," Cindy shrugged as we walked to class. "You're welcome to all the stuff mom and dad give me. Maybe there will be lessons on being a better suck up in one of them!" She laughed derisively. "Suck up? Me?" I exploded angrily as my face becoming to burn. "Dad rushed to your defense at breakfast this morning, so maybe you've been doing a little sucking up yourself? Playing the old "Daddy's Girl" routine again?" Cindy laughed and brushed her hair back with a quick flick of her wrist. "A little kiss goes a long way with guys, especially when it comes from their daughter!" "I bet them that you'll never be nearly as good as I am and kisses to dad won't make a difference," I scoffed unable to help but feel that she was somehow cheating. "I'm smarter, more motivated and with those tapes I'll pass you in a flash!" "Don't care, I'm still way prettier that you!" She laughed as she threw back her head and fluffed her hair. * Weeks went by with Cindy and mom still occasionally arguing over breakfast, Cindy was a slacker, there was no doubt about that but her grades weren't that bad. They both knew that the argument had deeper meaning for mom, Cindy had never been the sweet little girl of mom's dreams, she despised baby dolls, and fought being dressed up in pretty outfits even as a child. Even if Cindy had made the Honor Roll mom would not have be satisfied unless Cindy accepted the award in a beautiful gown! "Are you doing better in school Cindy?" Mom would ask in an innocent tone. "School still sucks mom," Cindy would nonchalantly shoot back to mom's horror. "Sucked then, sucks now, and it will go on sucking forever!" "I saw a really cute outfit at the mall yesterday honey," Mom would venture in a vain attempt to move the conversation around to what she really wanted to talk about. "Maybe I'll pick it up for you, it would make a nice school outfit." "Got enough jeans and stuff mom thanks," Cindy would shoot her down in flames. "Besides I'm not going to school in one of those "Little Miss Muffet" outfits you like so much. Too frilly for me!" Suddenly a picture of a frilly dress with puffy sleeves and a full skirt popped into my head. "Such a pretty outfit," I found myself thinking. "Cindy's so lucky and she just doesn't realize it! I'd kill for a dress like that." I nearly choked on my milk as I struggled to regain my thoughts. "What made me think something that crazy," I wondered. "Why would I want to wear a dress?" "What's your problem?" Cindy asked. "Thinking of getting one of the cheerleaders into an outfit like that? I'd bet you'd love that!" "I wasn't thinking anything at all!" I insisted, afraid that somehow she knew about the words that wouldn't go away. "But now that you mention it mom's right, you would look nice in a pretty outfit like that. It wouldn't hurt to look a little more like a girl you know! Think of how nice you'd make mom feel." "If you're so concerned about mom's feelings why don't you take the job?" Cindy shot back maliciously. "What job, what are you talking about?" I asked puzzled that I had somehow lost track of the conversation. "Daughter of the family!" Laughed Cindy as she waved her hand towards me. "There you go mom, your very own sweet little girl just waiting for you to dress her up in a pretty little dress with patent leather shoes, a little purse and gloves. You two could have a great time shopping for cute little party dresses!" "You're nuts!" I shouted ready to reach across the table at her. "You're a sicko too talking about stuff like that! It's just that... oh forget it!" Cindy looked at me strangely for a second or two before rushing off to meet her friends. I suddenly had a terrible feeling in my stomach. How did I let myself get involved in a discussion about my sister's wardrobe, I must be losing my grip! "Gotta roll," I blurted, grabbing my books and running out the door. I pushed myself to think of an upcoming trigonometry test to prevent those strange thoughts from returning. "Here ya go Jim," Cindy announced as she tossed several new tapes onto his bed a few days later. "Mom's motivational series, part two!" She laughed as she threw herself into a chair. "I don't know if I want these after our argument," I said even as I pulled the tapes towards me. "You were awfully nasty to me that morning you know." "You're breaking my heart Jim," Cindy sneered. "I seem to remember that you jumped on mom's side and took a cheap shot at me! Now you've got the nerve to sit here and pretend you're precious little feelings have been hurt. Bummer!" "But honestly Cindy," My voice took on a tone of sadness, of being misunderstood. "I was really trying to help you, you could look so pretty if you got dressed up once in a while..." Cindy dropped to her hands and knees and began scouring the room. "Come on out, I know you're here," She called out. "I'm trying to have a serious conversation with you if you don't mind!" I shouted as Cindy continued her searching. "What in the world are you doing?" "Looking for mom of course," She grinned. "I know she's hiding here somewhere, I can hear her! I can't figure out how she got your mouth to move as if it were really you talking but I am impressed!" "Get out of here you idiot!" I screamed as I finally lost my patience. "You're too stupid to realize how nice you could look and how happy you'd make mom!" Cindy turned and smiled. "The jobs still open and you can help yourself to any dress in my closet!" As she slammed the door behind her I threw myself on my bed and fought back the tears. Cindy was right, I had sided with their mother against her but why? It wasn't even my usual cheap shot at her, I was really trying to help! Now though Cindy thinks I should be some kind of sissy running around pretending to be a girl and if that's not bad enough there are those thoughts! The thoughts kept popping into my head at the most inopportune times, just that past week I had been in the middle of a History test on Victorian England and couldn't seem to force a picture of myself all done up in a pretty lace dress with a floppy hat and parasol from my mind. Not long afterwards I began to let my hair grow even though my parents badgered me daily to get it cut. "I think I look good with long hair mom," I patiently explained. "Lots of guys wear their hair long and some even pull it back in sort of a ponytail! It looks really great and it's the latest style." "The latest style for boys is to look like girls?" Dad asked with barely concealed scorn. "Sounds great, first you got an ear pierced and now you're letting your hair grow. Are you nuts or what?" "Gotta keep up with things dad or I'll end up as a nerd." "You already are a nerd," Laughed Cindy. "Now you're just a funnier looking nerd!" "Enough from both of you," scolded mom. "Jim, If you're going to have long hair you better make sure it's kept neat and clean or I'll cut it off while you sleep! And Cindy, listen to those tapes, I don't plan on throwing money away!" "Don't worry mom, I'm making good use of them!" Cindy assured her after a quick glance my way. I knew that I wasn't about to call her a liar, I enjoyed the tapes far too much to cut off my supplier. "And I'll keep my hair nice mom, I promise," I added feeling relieved that I could let my hair grow. Lately having long hair had become very important to me but I just couldn't seem to focus on a reason. "Maybe," I thought to myself. "I'm just trying to outdo Cindy again by showing her that I could look good in long hair when she insisted on keeping hers short." What I couldn't bring myself to admit though were the thoughts I was having of how pretty I would look with long curly hair! The arguments between my sister and mother continued on as did the tapes which as far as I was concerned kept getting better and better. The last bunch promised motivational messages mixed in with songs from some of the hottest rock groups, I would spend hours playing the tapes over and over while studying or drifting off to sleep. I kept waiting for my grades to take a giant leap forward, after all I played the tapes religiously and mom had promised Cindy they'd make a big difference in her life if she only relaxed and let the messages work. I'd spent many an evening with just a small light on in my room, headphones clamped to my ears, relaxed, listening, absorbing, and waiting. One reason I concentrated so hard on those tapes was because those goofy ideas kept coming back to me, you know the ones about wearing pretty dresses and having long curly hair. No matter how much I concentrated on those tapes though the thoughts kept coming. One day I was reading a newspaper and suddenly found myself drawn to an advertisement for girl's clothes. I stared at that page for five minutes straight and when I was finally able to put it down I had an overwhelming urge to put on some of my sister's clothes! Luckily no one was home and I quickly raced upstairs and threw open the door to Cindy's closet. There, pushed to the back I saw what I wanted, a simple, pink mini-dress that Cindy had worn once when dad took us out to celebrate a promotion at work. I grabbed the dress and quickly ran back to my room and locked the door. I swiftly removed my shirt, undid my belt, unfastened my jeans and stepped out them. My heart was pounding and my hands were shaking as I pulled Cindy's dress over my head then tugged it over my hips. Just as I finished adjusting it I was overcome with the most wonderful, peaceful, feeling I'd ever know. I stared at myself in the mirror, unable to move, unwilling to change. "This is Heaven!" I thought. I must have worn that dress for nearly half an hour, I practiced posing in different positions, walking, and sitting until just as suddenly as the urge hit me to put it on I felt that I had to take it off. I couldn't stop for a second until I had the dress safely back in Cindy's closet and had my pants back on. My heart was still beating wildly and my hands were sweaty and shaking. I couldn't believe that I had actually put on one of Cindy's dresses but my unbuttoned shirt and loose belt were proof that something terrible had happened. Or had it? I just wasn't sure and it was driving me mad! After that I found myself doing strange things that made me think I was going nuts. One day I was taking a shower and reached to shut the water off only to pick up the razor Cindy used to shave her legs. I stared at the razor and then at my legs. Suddenly I was disgusted by the hair on my legs, lathering up with a bar of soap I sat down on the side of the tub and removed every strand of hair from my ankles to my butt! Whatever demon was possessing my mind wasn't satisfied though and without giving it a second thought I shaved my underarms too! I ran my hands along my now smooth legs and admired the shapeliness I never before realized they had. They were smooth, silky, very pretty and I was very happy! I smoothed lotion over them to help keep my skin soft and silky then carefully patted myself dry with the fluffiest towel I could find before reluctantly pulling on my briefs and jeans. It wasn't until I was sitting on my bed putting on a pair of socks that I realized with horror what I had done! "What's wrong with me?" I wondered as I absentmindedly counted the strokes of the brush through my hair. After it happened I was sure that everyone I met could somehow tell that I tried on my sister's dress, fortunately I quickly realized that there was no way for that to be possible. It happened in the privacy of my room, I took it off and put it away again and there was nothing left to show for it, I was safe. Or at least I was until now! Now I'd be stuck wearing long pants even though the weather was warming up and everyone else would be wearing shorts. I was stuck until the hair on my legs grew back, if it ever would! If that wasn't bad enough there was always the problem with my underarms, if I wore my favorite muscle shirts, I couldn't raise my arms lest my girlish underarms be seen. "Boy, I really screwed up this time," I thought as I began my hundred strokes on the other side of my head. Once I finished my daily brushing routing I gathered my hair and pulled it back into a ponytail. "Too bad I can't use one of Cindy's scrunchies to hold my ponytail," I thought to myself as I put a rubber band around it. "These rubber bands are giving me split ends." At school I tried to concentrate on what was going on in class but I kept getting distracted by the girls in my classes. I couldn't stop staring at some of them, especially if they wore a skirt or dress! I didn't care what Cindy said about not wearing dresses to school, these girls wore them and they looked great! Judging from the way they acted they really seemed to enjoy being dressed up, they walked differently, they sat differently, everything they did seemed so feminine that it drove me wild and to my amazement jealous! I had to be crazy! I'm supposed to be a normal teenage boy lusting after pretty girls yet more and more I was envious of their pretty clothes, the way they wore their hair, and the way they moved. I wanted to be just like them, to have long, pretty hair, to wear pretty dresses and nylons, to tantalize with a slight scent of my perfume. It was insane, positively insane but I couldn't control the feelings building up in me, I wanted to be the daughter mom always wanted Cindy to be! I wanted to wear pretty dresses to school, to do my nails in pretty colors, I wanted to experience the delightfully wonderful world of a pretty young woman! One day in school there was a pep rally and the cheerleaders were allowed to wear their uniform's to class. I was in Hell as I watched those pretty girls in their short skirts walking down the halls laughing and having the time of their lives. Why was I stuck in these awful pants and plain shirt when I should be wearing something colorful and pretty? I had to do something about it but until I got home I would have to endure the torture of seeing these girls so self confident in their femininity practically daring me to join them! I couldn't begin to figure out why I felt the way I did, I never noticed those things before but suddenly they seemed so important to me! I tried to force the thoughts out of my mind but as before they came right back, stronger each time. One day I walked into the house after school and was relaxing with a sandwich and cold glass of milk when I was overcome with a strange feeling. No one was home but I'm not sure that would have made a difference, I had something to do and I'd simply die if I couldn't get it done! I went straight to Cindy's room and quickly pulled the pink dress from its exile at the back of her closet. This time though I wasn't going to rush back to my room to try it on as I had many times in the past few weeks, this time I was going to do it right, the way Cindy should! I opened every drawer in her dresser until I found exactly what I wanted, a pair of pretty satin panties that still had the tags on them, a bra, white pantyhose that Cindy had worn once, and a white half slip trimmed in lace. Carefully cradling my treasures I hurried off to my room before I came to my senses and put everything back. Just as I had done so many times in the last few weeks I locked my door and carefully checked to make certain that it couldn't be opened. I considered pulling my drapes shut but there aren't any other houses close enough for anyone to be able to see in my windows but the possibility made what I was about to do all the more exciting! I quickly removed every stitch of boy's clothing I had on then with trembling hands I pulled the satin panties up to my waist. I had tried on Cindy's panties before but they had all been cotton, softer than any of my briefs but nothing special, just plain white cotton without even a pretty little flower to brighten them up. Of course it felt very exciting to wear girl's panties but the feeling was nothing compared to what was happening to me now, the satin was so soft, silky, and cool against my skin that I had an instant erection! What a contrast, pretty satin panties being pushed out of shape by something that they were never meant to hold! I thought of an assignment I had recently done for English class on contrasting things, too bad I could never write about the contrast of the utterly feminine panties and an utterly masculine erection! It took a bit of work to get the bra on, this was to be my first time, guess I was saving it for a special moment, but finally I had it hooked in back and stuffed with some socks until I had close to what I figured Cindy's bust size was. The pantyhose were tough, I'd seen commercials and movies where a woman would start pulling on a pair but once again it was my first time and I was scared to death of putting a run into them, I'd never explain something like that away. I carefully inserted my right foot then slowly pulled them as far up as I could before putting my left foot in. When I finally had them worked up as far as my thighs I hesitated for just a second feeling that I was on the verge of taking a very important step. A deep breath and I slowly worked them all the way over my thighs and unrolled the waistband, my heart pounding in my ears, goosebumps popping up on every piece of flesh! "What was wrong with Cindy?" I wondered. "I'm only partially dressed and I can't believe how wonderful these clothes feel! How could she prefer cotton panties to these dreamy satin ones I wore, why would she ever wear socks when she could wear these stockings which were making my legs look so pretty and sexy!" The slip made me look much better hiding the unsightly bulge in my panties. The pantyhose helped keep it in check but now with the slip on I looked more like a girl with my pretty, nylon covered legs extending beyond the lace hem of the slip. Even though I was still excited I was becoming much calmer, more sure than ever that I should dress this way! I lowered the dress over my head with all the confidence and self assurance any girl my age would have. Every part of my brain was now telling me that this was natural, I was a young woman and this is how I was expected to dress! Completely dressed I was shocked to see Cindy's reflection in the mirror, I nearly panicked until I realized that Cindy wasn't in the room, I was alone, the girl in the mirror was me! Sure there were a few rough edges, Cindy had a few more curves than I did but I was sure that with a little padding here and there I could easily look every bit as pretty as Cindy did on those rare occasions when she did get dressed up. I'd love to have her see me now and tell me that although I'm smarter she's prettier, I'd show her who the prettier sister was in this family! My time in Heaven ended all too quickly, I had to hurry to undress and put things away before anyone came home. I was sure of one thing as I put the clothes away, something had gone terribly wrong, I'm supposed to be a pretty girl, not an average looking boy! From now on I vowed, I'd work harder until I could do everything a girl did and do it the way a girl did. When I was finished my family would realize that although Cindy was just an overgrown Tomboy I was a young lady and they'd treat me like the young woman I was meant to be! I admired myself for a little while until the feeling vanished as suddenly as it had come on and I found myself utterly disgusted by what I had done. I stripped off Cindy's clothes as fast as possible then quickly donned by own. After I finished putting my sister's clothes back I returned to my snack but found it difficult to eat with the tremor in my hands. What had happened to me? I had seemingly lost all control over my actions but I was too ashamed to talk to anyone about it Things kept happening more and more after that, I had an unquenchable desire to dress in Cindy's clothes, to shave my legs and underarms, and keep my hair long and pretty and I wasn't feeling nearly as guilty about it anymore! Keeping my legs and underarms smooth and silky became a part of my daily shower ritual, brushing my long hair wasn't a job, it was fun! I even graduated from wearing Cindy's clothes alone at home to wearing panties to school! It was so scary yet exciting, I'd be dressing after a shower and boom the urge would hit me! I'd wait until Cindy was downstairs then sneak over to her room and borrow a pair of panties. In school I had to be extra careful in the way I moved, sat, or stood to prevent anyone from seeing the waistband of my panties peeking over my pants. I was trapped, terrified that I'd be caught! Every afternoon when school ended I breathed a sigh of relief that I hadn't been discovered and vowed that I'd never do it again but the next morning would find me once again pulling on a pair of panties! The feelings had grown so intense that I started to dress more and more often and wanted to wear different things other than Cindy's pink dress. I tried on her jeans, her shorts, and her nightgowns, if it was in her closet or her drawers I at least tried it on, sometimes as I did with her panties, wearing them with my boy's clothes. It was nearly impossible for example to distinguish her white socks from mine but it made me feel like I was fooling people when I wore them instead of my own! I'll never forget the first time I wore them instead of my own, I was sure that mom, dad, Cindy, and the entire world could somehow tell that I was wearing a pair of girl's socks but no one said a thing or even looked at my feet! After going through Cindy's boring wardrobe I somehow came up with the idea of checking out my mother's clothes. She and Cindy were about the same size and whenever she went somewhere special she wore some of the most gorgeous outfits! I figured if she hounded Cindy so much about wearing more feminine clothes mom might just have some really pretty things stashed away in her drawers and I couldn't wait to try them on. I held out for over two more weeks before I finally had to give in to the urges. Mom and dad were going to be spending a Saturday visiting some out of town relatives and Cindy would also be gone until late evening. The instant I had the house to myself I locked all of the doors then ran to mom's room undressing as I went. When I reached her closet I had a strange feeling of excitement seeing the dresses, skirts, and suits of every color and style which called out to me to try them on! The first outfit I picked to try on was a dark blue dress with sheer sleeves that mom wore when she and dad went out for their anniversary dinner. The material was very sheer but there was something like a built in slip under it to keep it from being totally see through. I couldn't wait to try it on but I wanted to check out mom's lingerie first in the hope I'd find something pretty to wear under the dress. When I opened her dresser drawer I couldn't believe my luck, instead of white cotton I was staring at satin, nylon, and silk in so many different shades it was as I was staring at a rainbow! Almost every pair of mom's panties were lace trimmed, some were made of nothing but a stretch kind of lace, while others were so sheer and sexy I found myself blushing! For a moment or two I was shocked to think that my own mother wore these kinds of clothes then my heart began to pound as I realized that soon I too would be wearing such feminine and sexy items! I picked out several different matching panty, bra, and slip sets to try on but the one I couldn't wait to wear was black, beautiful, shimmery, silky, black with lace at the waistband of the panties, lace at the bottom and side slit of the full slip, and if that wasn't enough to drive me crazy the top part of the bra's cups were nothing but lace! I couldn't get out of my regular clothes fast enough, I was all set to tear my shirt when my fumbling fingers finally undid the last button. I pulled down my briefs but instead of placing them on a neat pile with the rest of my things I gleefully kicked them across the room, I wanted to have nothing more to do with such ugly, confining clothes, I was a young woman exploring my femininity and boy's briefs had no place in that world! If I still had any insignificant doubts about what I was doing they were erased forever when I slid the dress over my head, over my bra, panties and a pair sheer black pantyhose. I wanted to run out into the street and shout "I love being a girl" but I hadn't yet gotten the hang of the black heels I had also borrowed from mom's closet. I found a string of mom's pearls and after a few seconds work I managed to get them around my neck and fasten the clasp. I slipped a delicate gold bracelet on my wrist, fastened a dainty chain around my ankle, then set off on wobbly ankles for mom's vanity and makeup across the room. I reached the vanity without breaking an ankle then smoothed out my skirt as I'd watched girls at school do before sitting down. My reflection in the vanity mirror was pretty good, I looked a lot like Cindy might look in this dress without makeup on, but that wasn't good enough for me. I wanted to be the pretty sister and in front of me were the tools I would need to complete my journey from plain to pretty. I just hoped I could master them without anyone discovering what I was doing, I wanted to surprise mom with a daughter who was pretty and feminine, a poised and confident young woman! I spent the rest of the morning and the entire afternoon in mom's room experimenting with makeup, clothes, and hair all the while worried about the feeling that I was supposed to have been a girl. Fighting the feelings wasn't possible any more, I was caught in a web of satin and lace and there seemed no way out. I began to think of how happy I would be to let mom buy me skirts and dresses to wear to school! Cindy might rebel at the thought of wearing a pretty dress now and then but I wouldn't! I would learn the proper way to dress, do my hair, wear makeup, and behave as a proper young woman and mom would be so proud of me! I had so much to learn but I wasn't finding a whole lot of time to study. Mom and dad were staying home more on the weekends and with finals coming up Cindy was actually coming straight home from school to study. Luckily I was able to sneak some of mom and Cindy's things into my room where I hid them in the back of my closet. In the afternoons I'd go to my room to study but it wasn't school work I was studying, instead I was hard at work trying to master makeup and hairstyling. One Saturday afternoon after finishing showering and shaving my legs and underarms I was sitting on my bed combing out my hair as Cindy walked past my room. "Your hair's getting pretty long," She laughed as she watched me carefully pull a comb though his hair. "Almost ready for some pretty ribbons and bows!" Cindy's comments brought the old feelings crashing back on me, I shouldn't want long hair and I certainly shouldn't have been wearing the panties I had on. I wanted to cut my hair off right then and there, to change into a pair of boy's briefs and burn the panties. I wanted to, but then I thought of how pretty my hair would look tied back in a ponytail with a pretty ribbon holding it in place. I thought of how smooth and soft the panties were and how rough and heavy my briefs were and it wasn't a contest. I couldn't do anything about what was happening to me and I knew it. Lost in thought I dropped the brush I had in my hand and bent over to retrieve it. "Those are my panties!" Cindy exclaimed as she spotted her satin panties. "What are you doing wearing my underwear you little pervert?" "I can explain Cindy, just gimme a chance," I begged. What are you trying to pull?" Cindy asked suspiciously. "What are you doing with these things?" I spent a long time trying to explain things to Cindy who seemed to have a hard time understanding what made perfect sense to me, at least at that time. Cindy stared at me as if I came from another dimension. "I don't understand but I think you'd better tell mom. Dad's gonna freak, that's for sure!!" "I guess he will," I said sadly. "I can't help it though, I should have been a girl, just like you. Only thing is that I really like getting all dressed up and wearing frilly stuff, I want to be the kind of girl mom wants you to be, all satin and lace and stuff!" "So what do you need from me?" Cindy asked cautiously. "I can't do anything about dad, I'm sure mom will be proud of you, surprised as all heck but proud!" "I'm having a lot of trouble learning to apply makeup and fix my hair," I told her. "I was hoping you could help." "But you're a boy!" Cindy exclaimed, exasperated. "Boys don't wear dresses, they don't wear makeup, and they don't run around in their sister's underwear! Look, you and I weren't exactly close friends but I just don't think I can handle helping my brother become a girl." "Please Cindy, I'll be a great sister I promise," I begged. "If you're that serious about being a girl, why not ask mom to help? She knows more about makeup and hair styling than I do." Cindy suggested. "You're going to have to tell her anyhow you know, why not do it now and let her help?" "You don't understand Cindy, I want to surprise mom. I don't want to say anything to her until I can do everything any other girl can do, until I'm as much of a girl as I can be!" "But what if someone finds out about you? What about the other kids at school?" Cindy challenged, obviously trying to weasel out of helping me. "I guess they're bound to find out," I shrugged. "But that's not going to make any difference at all. I'm going to be a girl whether they like it or not! It took a lot of convincing before Cindy agreed to help but it's not every day that a girl's brother asks her to teach him how to be a girl. She didn't wear makeup so she couldn't teach me much herself but she did promise to pick me up a few magazines and she even agreed to buy me my own makeup! She was never this nice to me as her brother, it was obvious that being her sister was going to be much nicer! Mom wasn't letting up on Cindy, the constant battle over Cindy's dressing continued but Cindy didn't complain as much anymore. She simply take the clothes, jewelry, and makeup mom would buy her and put them in her room for me to use. It was a good system, I got the latest styles, makeup that was perfect for me and since mom occasionally checked and found that the stuff was being used she eased up on Cindy. Mom was happy, Cindy was happy, and I was ecstatic! After a few weeks had passed Cindy seemed to forget her reservations about turning me into a girl and became very helpful in my drive to replace my boy's clothes with girl's clothes. The first thing to go were my briefs of course, replaced by the prettiest, silkiest panties Cindy could find for me. I replaced my white sweat socks with girl's socks, bought several girl's tee shirts like Cindy wore and even found a pair of girl's sneakers that were plain enough to pass as boy's sneakers. It was so wonderful for me to go off to school wearing panties, a girl's tee shirt, girl's socks and sneakers, the idea that I was somehow trapped, that I couldn't possibly change into boy's clothes was both scary and exciting! No one ever batted an eye though, I was just another long haired guy as far as my friends and family were concerned! One day after school had ended for the year though mom started picking on Cindy wondering why she'd spend so much money on makeup and pretty clothes then never wear them out of the house. "Don't worry 'bout it mom," Cindy replied trying to avoid ruining my surprise. "Maybe someday when you quit bugging me about it I'll get dressed up and let you take me shopping. Until then don't bug me!" That was the wrong thing to say to mom and Cindy quickly found herself on the receiving end of a tongue lashing that would have gone down in the history books as the greatest of all time. She was being grounded for a month, her phone privileges were being taken away, and there was more to come until I spoke up. "Please don't yell at her mom," I pleaded. "She's only trying to help me surprise you." Mom stopped suddenly, her momentum in the argument lost. "You're not involved in this Jimmy, please mind your own business." "That's just it mom, I really am involved and I'll prove it!" I told her as I left the table. I went to my room and from a box I had hidden in my closet removed pictures that Cindy had taken of me modeling different outfits. returning to the kitchen I laid them in front of mom and proudly announced, "This is my surprise, the daughter you always wanted Cindy to be!" Mom studied the pictures for a few seconds then smiled broadly. "I'm sorry Cindy, you look lovely in these. Were you planning on surprising me?" "Not exactly mom," Cindy hesitated for a long time then glanced towards me. "That's not me those pictures." "Of course it's you?" Mom seemed puzzled, glancing at the pictures then at Cindy. Finally she took note of Cindy staring at me. "If it isn't you then who is it?" She asked looking straight at me. "It's me!" I replied filled with pride. "I hope I look good enough to make you proud of me!" "T..t..this is you?" Mom gasped as dad pulled the pictures from her hand. "What in God's name are you up to?" "Oh my Lord, " Dad uttered softly. "Tell me this is some sick joke you're pulling Cindy." "I thought so too at first dad but Jimmy convinced me that it wasn't," Cindy explained, "Believe it or not, that's Jimmy in those pictures." Mom looked at me dumbfounded, "Jimmy?" She asked, her voice strained. "You'd better have an awfully good explanation for this." "How can he possibly explain these!" Dad thundered as he threw the pictures in front of me. "This is sick!" "I don't understand," I said sadly. "It just seemed to happen all of a sudden, I don't know why." "Will everyone please calm down," Mom interjected stepping between me and dad. She laid the pictures in front of me. "Now young man would you please explain why you're wearing girl's clothes in these photos?" I thought for several seconds on just how to answer mom's question before deciding not to drag things out. "I want to be a girl, that's why." "You what?" Dad asked seemingly stunned at my announcement. "Are you serious?" Mom gasped. "You can't be serious!" "A girl, you want to be a girl?" Dad was obviously shocked, his face had lost all color and his eyes were bulging. "When did this happen? You've never mentioned anything like this before." "I can't remember wanting anything more than I want to be a girl," I explained as best I could. "Maybe I didn't realize it before but now I'm absolutely certain that I want to be a girl." "But why?" Mom asked trying to remain calm even though she appeared to be on the verge of crying. "What made you decide you want to be a girl?" "I don't really know how it happened mom, I tried to ignore it and be like any other boy but I couldn't help feeling that something was wrong. I started trying on Cindy's stuff and then I knew for sure, I should have been a girl." By now I was on the verge of tears. "Please daddy don't be mad at me, I can't help how I feel." Dad stared at me but the look of disgust was beginning to fade. "When did you start thinking that you should have been a girl? What could suddenly make a normal boy decide that he'd rather be a girl?" "I'm not sure," I said as I wiped a tear off my cheek. "The idea of dressing up seemed to come a couple of months ago and it just got worse and worse. I tried not to give in but the feelings were just too much for me, one day I was taking a shower and wanted to shave my legs and underarms, before I knew what was happening I was wearing Cindy's dresses then mom's underwear." "Wait a second," Cindy announced, an odd look in her eye. "Mom, when did you start getting those tapes for me?" "I don't know," Mom replied offhandedly. "Three, maybe four months ago why?" "And they were just supposed to motivate me more in school right, nothing else?" Mom hesitated before answering. "Not exactly, school was just a minor part of it, actually they were supposed to make a young lady out of you but I guess they were a waste of money." Cindy started to laugh and soon had tears rolling down her cheeks. "No, actually they would have been worth every penny you paid for them, if I listened to them!" "I'm confused," Dad said. "Those tapes were supposed to make you act like a young lady but you never listened to them, what's the joke? "I wanted to throw them away," Cindy laughed as she dried her eyes. "But Jimmy stopped me, he's been listening to them all along! You got the sweet young lady you wanted mom, it's just that she's your son!" I was wearing a big smile when mom and Cindy turned to look at me, I was thrilled that mom had referred to me as a girl and I knew I'd show Cindy that I was no bimbo! "You're really getting into this aren't you? Cindy prodded me. "The idea of having to spend the rest of your life as a girl doesn't bother you in the least does it?" "I admit that it's a little bit scary but if I'm going to be a girl at least I'm going to be pretty!" I smiled as I tucked a strand of hair behind my ear. "Those tapes worked so well that I'm really looking forward to becoming a girl! I'll get to wear soft pretty clothes like these, have my hair done, and I don't have to pay to see a movie anymore!" "That's a definite plus, I gotta admit," Cindy laughed as she gave me a hug. "It's going to be different having a sister around, mind if I borrow an outfit now and then?" "No sweat, you were nice enough to share your things with me so help yourself to anything I get!" I felt a closeness to Cindy that I never really felt before. We'd always kept each other at arms length, I didn't understand her world and she didn't understand mine. Now our worlds would be the same! "Let's quit gabbing, dad's waiting to meet his new daughter." With that mom gently took me by the elbow and led me to where dad was waiting. He seemed somewhat confused at first but then he smiled and told me I looked very pretty. That compliment from dad was the sweetest thing he'd ever said to me, if he could bring himself to accept me as a girl my life had just become so much easier! "Thank you daddy," I whispered as I kissed him on his cheek. "I promise I'll make a good daughter for you." The kiss seemed to cause dad to fall into a trance for a few seconds. Shaking his head he snapped out of it and sighed. "I love you very much Jamie but it's going to take a little adjustment before I'll get used to your calling me daddy and kissing me like that." I kissed him on the cheek again then threw my arms around him. "Tough daddy, you'll just have to get used to it!" Mom got all misty eyed and threw her arms around me. "Oh Jamie, it's so wonderful to have a daughter that would want to wear such feminine things! I can't wait to buy you all sorts of pretty outfits and show you how to look pretty and sexy!" We had a wonderful time that evening, dad seemed proud to have three lovely ladies for dinner dates and mom was happy when Cindy relented and wore a dress too! I don't remember having such a wonderful time with my family before and knowing that it meant dad's acceptance of me as his daughter just made things that much more wonderful! * The next morning I wondered if I had been dreaming until I noticed the nightgown and panties I was wearing. In all of the months that I'd been dressing up I never had the courage to dress up overnight but now I was wearing a very cute little nightgown and if that wasn't proof enough there hanging on my closet door was the dress I had worn. It was true then, I really was a girl! At breakfast everyone acted as though there was nothing unusual for me to be wearing my pink babydoll nightgown but I got a very rude surprise when I sat down on the cold wooden kitchen chair. I always wore some type of bottoms as Jimmy and it simply had never occurred to me that the thinner fabric of girl's clothes would not be much value against a cold chair! "Now do you understand why I don't wear nightgowns to breakfast?" Cindy laughed as my eyes grew wide with shock. "Guess there's a few little tricks you still need to learn, like making sure you're wearing something warm in the mornings!" "I'll make sure I remember that!" I laughed as I struggled to pull my nightgown further down. "Gotta admit, I never thought of that before!" After breakfast I was thankful to change into a pair of cutoff shorts which made me feel much more secure on cold seats! Cindy reached down and pulled out a large brown envelope she had been sitting on. "Here are a few other things to get used to Jamie dear". I opened the envelope and nearly fell off the chair when I saw a birth certificate made out for a Jamie Lynn, with the sex clearly marked Female! The surprise didn't end there because the next thing to fall out was a temporary driver's license also made out to Jamie Lynn! "Put on something pretty Jamie," Dad said as he kissed me on the cheek. "Once you get your picture taken you'll officially be female!" I was sobbing tears of joy and had to muster all my composure to thank everyone for being so good to me! It seems like so long ago that I became Jamie but looking back it has only been months since I had the final operation. I'm in college now having a wonderful time and have no regrets over what happened to me within the last year. Dad has accepted me completely and has even managed to be civil towards my dates when they pick me up. Mom is thrilled to finally have the daughter she always hoped for, Cindy and I have become much closer and to add to mom's delight she has even begun taking an interest in her looks, frequently borrowing my clothes! It all worked out for the best, mom got the change she was looking for in Cindy, I got a whole new lifestyle that I've really come to love, and dad now has three women to pamper him! END ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ Please keep this story, and all erotic stories out of the hands of children. They should be outside playing in the sunshine, not thinking about adult situations. ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ Kristen's collection - Directory 66