A Hidden Talent free porn video

A Hidden Talent By Karen Elizabeth L. Copyright 1999 This story may be archived provided the site does not charge a fee and no changes are made to the story. Chuck was feeling pretty low, he had managed to strike out every single time at bat that afternoon. Striking out was what Chuck did best, he was so good that he never once came anywhere close to the ball, much to his teammates disgust. The fact that Chuck was even on the team showed how very understanding his coaches were, he had no talent for the game despite intense training. Actually, Chuck hated the game but his mother insisted that 'baseball is what boys do!" , and he had to do what other boys did whether he liked it or not. Chuck preferred to stay home and, at least that way no one made fun of him or called him a wimp and a sissy when he struck out or dropped a fly ball. Chuck's dad had left the family years earlier and there was no one to teach him the things he needed to know to fit in. His coaches tried but it was really no use, Chuck just wasn't cut out for athletics. That afternoon though Chuck found something he was good at, a talent he never knew he had, something he was probably better at than most of the boys he knew. That afternoon he found that with very little work he could look as cute as any girl he knew! Chuck would probably never have made the discovery on his own, he was too involved in his reading to care about anything else. Fortunately for him his sister Jill needed some help with her home economics project and Chuck just happened to be handy! Jill was Chuck's older sister, she was sixteen, a Junior at the school they attended, he was fifteen and a sophomore. Jill had been taking Home Economics for several years but this year was different, this year she had to learn to sew. Learning the basic stitches was tough enough for Jill but now she had to put them together as an outfit. She had managed quite nicely so far, choosing a simple dress pattern that once completed she wouldn't mind wearing. The dress was a pink shift with zipper in the back and a sewn in belt around the waist. So far it hadn't posed any real problem but now she had to make sure the length was just right and that the side darts were perfect. She couldn't make any changes while she was wearing it so she turned to the only person she knew that was close to her size. "Chuck," She called sweetly. "Could you come here, I need your help with something?" "Sure Jill, be right there." He called back, putting aside the book he was reading. "What's up?" He asked as he entered her room. "I need some help with my sewing project and since you weren't busy..." "What kind of help could I be?" Chuck asked. "I don't know the first thing about sewing." "You don't need to be able to sew, all I need is for you to wear this for me while I make some changes." Chuck looked at Jill as if she were asking him to jump in front of a moving truck! "You're goofy!" He exclaimed loudly. " I can't wear your dress, what if someone sees me or something?" "Please!" Jill pleaded. "Mom's not my size and you do owe me for the help in Geometry remember?" "Yeah, I know I owe you but this is way too much to have to pay! If any one saw me.." "I'll close the curtains and I promise not to tell anyone. Please Chuck, I really need help!" Chuck wanted to refuse but his sister was his only close friend and she had always been there for him. "All right," Chuck said in a low voice. "But this makes us even for the Geometry!" Jill gave him an affectionate peck on the cheek. "You're a doll little brother, I'll make this up to you I promise. Now I'll wait in the hall while you get changed!" Jill quickly left the room leaving Chuck to get changed. As he undid his shirt and slacks he found himself thinking that this time he'd really gone off the edge. Imagine, a boy putting on a dress just to help his sister with a class! He could just imagine the teasing he'd get if anyone ever found out about it. After getting his shoes, pants and shirt off Chuck reluctantly slid the dress over his head and put his arms into the short sleeves. He pulled it down as best he could before calling Jill back into the room. "This is as good as I could do," He said shrugging his shoulders. "I can't reach the zipper." "No problem," Jill replied as she turned him around and zipped up the dress. "Let's see just how much work I still have to do!" Jill took a few steps back to admire her creation then had Chuck turn around so she could see how the dress looked from the back. "I need one more tiny little favor Chuck", She said slowly. "Now what?" Chuck asked skeptically. "Isn't it enough that I'm standing here in a dress? What else could you possibly want from me?" "A bra," Jill said softly. "I need you to wear a bra." "A bra!!!" Chuck shouted. "No way, no how! I'm getting out of this right now!" "Please Chuck! I know I'm asking a lot but it's really important to get this just right and without a bra there's just no way to tell if I have too much material!" "But a bra! What next, stockings?" "No, just a bra, I promise that's it! And I'll be forever in your debt!" Chuck thought for a second, he was already standing there wearing a dress so what difference was there in adding a bra? The curtains were shut, no one could see what he was doing. "Okay, but that's it." He said as Jill brought a bra from a drawer. "Promise me that you won't ask me to wear anything else!" "I promise!" Jill replied as she unzipped the dress and helped him take it off his shoulders. "Now hold out your arms so I can get this over with!" Chuck meekly held his arms out straight so that Jill could slide the bra up to his chest. A moment later she had it fastened and was reaching for some pantyhose. "Hold on!" Chuck shouted. "You promised!" "Calm down," Laughed Jill as she inserted the pantyhose into the cups of the bra. "I'm just adding a little padding! I think I look better that the average boy you know!" "Sorry," Chuck said sheepishly. "I was getting a little worried!" "Relax, we'll be done in a few minutes and you can take the dress off!" Jill proceeded to tuck here, measure there, and pin various parts of the dress. Finally she stepped back and smiled. Okay little brother, you're all done. Let me help you out of that before you stab yourself!" Jill unzipped the dress and carefully helped chuck step out of it before unfastening the bra. "You know you didn't look bad at all in that dress!" She smiled. "I'll bet that with little work you'd really look cute!" "Excuse me?" Chuck asked, shocked that his sister would even suggest what he was thinking! "I didn't mean it to sound nasty or anything," Jill replied. "It's just I'd bet that with a little makeup and a curling iron you'd look like a cut e girl! How about it? Want to give it a try?" "No thanks!" Chuck shot back. "I think I'll take a rain check on that one if you don't mind! I have enough problems as a boy without being turned into a girl!" "You're loss!" Jill replied. "Besides silly, I wasn't going to turn you into a girl. I just thought it would be neat if ..." Chuck cut her off before she could finish. "Thanks, but no thanks, Jill!" He said as he pulled his pants back on. "Help me out of this bra please." After Jill unfastened the bra Chuck pulled on his shirt and pants and went back to his reading. Weeks went by since he helped Jill and yet he couldn't get her suggestion out of his mind. Finally one Saturday when their mother was working he went to Jill's room where she was putting the finishing touches on her dress. "Hi Chuck, what brings you up here?" Jill asked as he entered the room. "I've been thinking," He said slowly. "Remember how you said you'd owe me big time for helping with your dress?" "Sure!" Jill replied. "Name it, help with Algebra again?" "Well," Chuck stammered "Actually I was thinking of different kind of help." "Like I said, name it and I'll see what I can do! I couldn't have finished this dress without you!" "Remember how you said that you thought I'd look cute?" Chuck mumbled as he stared at the floor. "I'm sorry Chuck," Jill said. "I didn't catch what you said." Chuck took a deep breath then knees shaking he repeated himself. "Are you serious?" Jill asked dumbfounded. "Please don't laugh," Chuck said, tears welling in his eyes. "I just can't seem to stop thinking about what you said and if you'd be right!" "I didn't mean any harm Chuck," Jill said worriedly. "It's just that for a second or so you looked sort of cute standing there in that dress. I didn't mean to upset you!" "I'm not mad Jill, honest I'm not. You said I could ask any favor of you and you'd do it. That's the favor I want!" Jill stared at him for a few moments before speaking. "Are you sure about this?" It was all Chuck could do to get the words out of his mouth but he finally did. "Please Jill, " He pleaded. "I haven't been able to get it out of my head since you asked me to help with that dress." "Okay already, if it's that important to you I'll help. You are sure you want to try on my clothes?" Jill shrugged her shoulders still unsure. "I'm positive. Mom's not going to be home for a couple of hours so I thought this would be a good time." "Okay by me Chuck! I promised I'd help with anything I could! There's just a couple of things you need to decide before we get started." Chuck's heart was beating so hard he thought it would burst. He'd thought about this over and over again for weeks now and finally he was about to go through with it! "Shoot!" "First of all, how far do you want to go? Just makeup? What about your hair? Tell me what you want and I'll take care of it!" Once again Chuck had to call up every last bit of strength he had left to answer his sister's question. "I want everything!" "Everything?"" Jill repeated. "As in a dress and everything?" "Everything." Chuck repeated. "Please !" Jill waited a second before she slowly asked her next question, wanting to make sure she really understood what Chuck wanted her to do. "As in a complete outfit, with stockings, shoes, and .." She paused again. "Underwear?" "Please Jill, this is hard enough." Chuck sobbed. "Please I want to wear a dress and all of the underwear and stuff you'd wear with it! Everything!" Jill handed him a tissue and told him to start getting undressed while she got some things ready. She kept talking to him the whole time, trying to calm him down and make him relax. "I think we'll start simple and work our way up," She said as she went into her closet. "Let's start with a pair of jeans and a top for now okay?" Chuck nodded agreement as Jill laid a pair of her jeans and a top on the bed next to him. She then went to her dresser and pulled out a pair of white cotton panties, a bra, and a pair of her socks. "Put on the underwear, socks, and jeans, then call me and I'll help with the bra!" Jill said as she gave him the underwear. "Enjoy!" Chuck's hands trembled as he removed his underwear and pulled on the ones Jill had given him. He noted that they were only about half as thick as his underwear and the waist band was much thinner too. He pulled on the socks then quickly pulled on and zipped the jeans before calling Jill. "Not bad!" Jill said with an admiring glance. "How's everything feel so far?" "Soft," Chuck said happily. "Soft and very comfortable!" "Great! Let's get your bra on then we'll get started with your hair and makeup." Chuck felt a little uneasy hearing Jill refer to "His bra" and "His makeup" but it was his choice to put on girl's clothes in the first place so he couldn't let this bother him. Jill showed him how to put on a bra by himself, 'just in case he ever wanted to', then sat him in front of her vanity to work on his hair and face. She took her time to make certain that everything was perfect then after about half an hour of spreading things on his face, eyes, and lips, sprayed his hair with water and used her curling iron on it. Once she was satisfied she padded the bra with pantyhose then helped him into the top to keep from messing up his face and hair. Staring at himself in a full length mirror chuck was stunned to see that his sister was right, he looked so much like a girl that he had to put his hand up to make sure it wasn't Jill in the mirror. "Happy?" Jill asked hesitantly. "I think you look pretty good if I do say so myself!" "Thank you!" Chuck cried as he hugged his sister. "I can't believe how nice your clothes feel! Even your pants feel better than mine!" "Yeah," Replied Jill. "Whenever I helped put away clothes I always noticed how soft my things were compared to yours. I guess girls are just luckier than boys!" "Way luckier!" Chuck said as he ran his hands across the top and over the jeans he was wearing. "These feel so nice, I wish I never had to take them off." "You look really nice Chuck, those jeans look great on you and you've got a really cute shape! Want to see what you'd look like in some other outfits?" Chuck was already pulling off his top so Jill went to find something else for him to wear. She came back with a pair of white shorts, a green top, and green socks. Chuck quickly pulled off the jeans and stepped into the shorts. He carefully pulled the top over his head then tucked it into the shorts before putting on the socks. Once again he saw a young girl staring at him in the mirror and once again he couldn't wait to try on another outfit. "So far so good Chuck," Jill smiled. "How about my school uniform?" "You mean your skirt and blouse?" Chuck asked hopefully. "Sure, any problem with wearing a skirt and stuff?" "You don't think I'm weird or anything do you?" "Well it is kind of strange for me to see my brother wearing my stuff but if you don't mind I don't care either. Now, ready for a skirt?" "What about the rest?" Chuck prodded. "You said I could wear everything you wore remember?" "I remember, start getting undressed while I get the stuff together." As he removed the shorts and top Jill handed him a half slip, knee socks, a pleated gray skirt and white cotton blouse which he eagerly donned. Although she didn't quite understand her brother's fascination with dressing up in her clothes Jill couldn't miss the satisfied look on her brother's face as he buttoned the blouse then tucked it into the uniform skirt he wore. His hands trembled as he zipped and buttoned the skirt before slipping on the blazer Jill held out to him. Chuck slipped on a pair of black loafers Jill always wore to school then picked up a stack of books. "See you after school!" He laughed as he pretended to leave the room. "Hold up!" Yelled Jill playfully as she handed him her purse. "I never go to class without my purse! I'd be lost without all the stuff in there!" Chuck accepted the purse then slung it over his shoulder the way he'd seen Jill do it. "Well, do you think anyone would notice the difference?" Jill studied him for several long moments. She looked at him from the front, then from the back, then from each side. As far as she could tell he was every bit a girl going off to school "I think they might get suspicious when you flunked every class and definitely in gym class but other than that I really doubt it! You look so much like me it's spooky!" Chuck suddenly noticed that Jill was getting a strange look on her face. "You're up to something, I can see it in your eyes!" "Oh , I was just thinking." Jill smiled. "You've tried on my jeans, my shorts, and even my uniform, how would you like to get really dolled up? "Sure, why not!" Chuck said. "I'm putty in your hands!" Jill went back to her closet and spent much longer than before searching for something. Finally she called out that she had what she wanted and for him to take off the uniform, slip, bra, and socks . Chuck was completely mystified, but couldn't wait to see what she'd come up with next! "I wore this when Greg took me to his parent's country club!" Jill said as she stepped out of the closet holding a dress. "I'll bet you'll look just darling in it!" Chuck broke into a smile as he saw the dress his sister laid out for him. It had cost almost two hundred dollars when their mother bought it for her and it was worth every penny of it! To Chuck the dress was breathtakingly beautiful, a pale green shift with a white lace shell over it. Jill had looked fabulous in it as any guy who had been at the country club that night would happily swear to. She had guys literally begging her to dance with them that evening! Jill gently set the dress on the bed and retrieved some things from her dresser drawer. Turning back to Chuck she smiled and showed him a pair of light green, nylon panties, a matching satin bra and full slip, and a pair of smoke colored pantyhose. "Still want to go through with this?" She asked innocently. Chuck was speechless looking at the items in Jill's hand. Finally he managed a nod of his head. "You're going to have to change into these," She told him as she handed him the lingerie. "The other stuff just isn't pretty enough to wear with this dress. You can change your underwear in the closet if you like." "This time they go on your legs my dear little sister." Jill said with a wicked grin as she handed him the pantyhose. "Hope you don't mind me calling you that by the way but if you're going to wear my clothes, you're going to have to get used to being my little sister!" "That's okay with me," Chuck replied. "I think I could get used to being your sister! This is great!" "I agree!" Jill said as she took the cotton panties he handed her and handed him the nylon ones. Next she showed him how to put the pantyhose over his feet and roll them up. "I used to love playing "Dress up" when I was little. I think that's why women like to shop so much, it's sort of like playing that game for big girls!" By the time Chuck had changed bras his hands were shaking again. All of the other outfits had been just a lark but the underwear he now wore along with the silky pantyhose and the dress that awaited him were more than a game. They were the things that separated the little girls from the women! Wearing them was the same as shouting to the world, "Hey look at me, I'm all grown up! I'm a woman now!" Chuck knew that he was standing in front of some invisible line, a line that boys just didn't cross! Yet he wanted to cross that line, he had to see for himself what was on the other side of that line! "What's wrong Chuck?" Jill asked as she saw a strange look cross her brothers face. "I don't know if I can wear these things Jill." He said in a low voice. "It's just not right for me to be wearing pretty clothes and stuff like that!" "But you asked me to help." Jill replied concerned that she had done something wrong. "I'm sorry if I did something wrong. I thought we were having fun!" "You didn't do anything wrong Jill, it was all my fault. I guess I thought that since I was a failure at being a boy I'd see what it was like to be a girl." "I thought that might be it," Jill said sitting next to him on the bed. "So what though, you're certainly not hurting anyone and you know I'd never tell, why not relax and have some fun?" "But don't you think this is going a little overboard?" Chuck asked gesturing to the lingerie he wore and the dress. "Look, " Jill said in a firm voice. "You wanted to see what it was like to look like a girl and that's what we're doing, making you look like a girl! We're not sending you off for any operation or anything that can't be changed back again. If you don't like the clothes you can always take them off and be a boy again!" "And what if I like them?" Chuck asked, his voice quivering. "What do I do then?" "Hey, if you like them, help yourself!" Jill replied as if it were perfectly logical. "As long as I didn't plan on wearing an outfit you're welcome to it along with anything else you might want to wear. I've got plenty of clothes!" Jill made Chuck feel so much better that after a few minutes with some tissues he meekly raised his arms and let her pull the slip over his head. She showed him how to pull it down properly and adjust the straps and then he was ready for the dress. There were no buttons to button and no zippers to zip on that dress. All Chuck had to do was to raise his arms above his head and accept the dress as it covered him in feminine beauty! When Jill finally lowered it over his head he felt as sense of pleasure he'd never known before. Somehow it just seemed so wonderful to be wearing his sister's clothes that he decided he never wanted to stop! Jill straightened the dress out to ensure that no sign of the slip Chuck wore was visible under the dress sand that all wrinkles were straightened out. She had him step into a pair of mid heel green pumps that went with the dress then led him back to the makeup table. This time she took off most of his old makeup replacing it with subtle shades of eyeshadow to match his dress and darker shades of lipstick and blush to make him look like a beautiful young woman rather than a cute girl. "How about a manicure Miss?" Jill asked with a smile. Chuck wasn't sure what his sister had in mind but he couldn't wait to find out so he quickly agreed and Jill went to work on his nails. She spent nearly fifteen to twenty minutes filing and shaping them before she reached into a drawer and pulled out a package of press on nails that would perfectly match his lipstick. After gluing them to his nails she clipped a pair of dangling Jade earrings on his lobes, the n fastened a gold necklace around his throat. One look in the mirror was all he needed, Chuck was thrilled at the young woman he saw. "Well, is it everything you hoped for?" Asked Jill. "I feel so good I think I'm going to burst!" Chuck shouted. "I can't believe how pretty you've made me look!" "Thanks but I just took what you had and fixed it up a little bit." Jill said with a shrug. "I hate to have to tell you this Chuck but actually you make a better looking girl than many of the girls at school!" "That's okay Jill, I don't mind it a bit!" Chuck said. "I guess it's a compliment in a way!" "Question is though little sister, what now? You can wear my stuff whenever you want but you better not let anyone see you wearing panties or you're going to be in all kinds of trouble!" "I know, I know , " Chuck replied sadly. "All dressed up and nowhere to go. Would you teach me how to dress and use makeup and stuff Jill, please?" "You're really stuck on this aren't you sis?" Asked Jill. "You want me to make a girl out of you don't you?" "I'll do anything you ask, I promise. I'll help with your sewing projects, I'll clean your room for you, anything you want!" "This is really freaky you know that don't you?" Jill asked. "But then again it would be cool to have a sister to talk to whenever I needed another girl's opinion. Sometimes mom just doesn't get it!" "Then it's a deal?" Chuck asked. "I'll be the best sister any girl could ever want!" "Sure Chuck, it's a deal. Who knows, we might be able to sneak out to a mall once in a while if you want!" Jill suggested. "How would you like to be my sister in public?" Chuck thought about the danger involved but something was pushing the words out for him. "That sounds great!" "Okay!" Jill shouted. "We'll try it in a couple of weeks, maybe just a pair of jeans and a top for now though. I don't think you're up to anything special just yet!" "Do I have to wear cotton underwear?" Chuck blurted out without thinking. Jill looked at her pretty brother and smiled. "You're a big girl, you can wear anything you want!" Chuck didn't reply but Jill could tell from the smile on his face that she had a new sister! She smiled as she thought of the new opportunities this opened up for her. There were those stupid events at school she hated attending. Maybe now her twin sister could go instead! Chuck spent the next several hours trying on different outfits from Jill's closet. He was thrilled to find that no matter what he chose the outfit fit like it was made for him! No problems with having to put an extra hole in his already small sized belt to hold his pants up, most of Jill's slacks fit him perfectly without a belt! Jill's tops were also a perfect fit for Chuck who couldn't decide which he liked most, Jill's silky dress tops or her ever so soft and comfortable casual tops. Since his mother was often at work when he got home from school it wasn't at all unusual to find doing his home work in a skirt and top with his nylon clad legs curled under him. He was always careful to change clothes long before his mother as due home and remove any makeup that he might have been wearing to prevent his mother from finding out about his new hobby. His mother did notice a change in his attitude, often commenting on how much happier he seemed lately. Chuck would just smile and tell her that there was nothing new, he just felt happy. He wasn't about to tell her that he wore Jill's underwear nearly as often as Jill did! Jill did her best to keep her promise to her brother, never complaining when he wanted to wear a particular outfit or borrow her makeup. Chuck was always very neat, replacing her clothes on their hangers, even pressing off an outfit that may have been wrinkled so she couldn't complain. She kept quiet to their mother since it really did seem to make him so much happier than he'd been. As far as Chuck was concerned things couldn't have been much better, he got to wear any of Jill's outfits and was always available to help her hem a skirt or model a new outfit to let her get an idea of what she'd really look like in it. Occasionally they even polled their allowances to be able to buy an outfit they both liked! Chuck was sure he had it made, tired of failing as a boy all he had to do was go to his sister's closet and in minutes he was an attractive teenage girl ! No one but him and Jill knew what was going on and he was very certain that it would stay that way! It was mid -October when Chuck's mother made the suggestion that brought him back to reality! "There's a Halloween party coming up at work in a couple of weeks" She announced as she walked in from work one afternoon. "Should be a lot of fun! Anyone interested?" "No thanks mom," Jill replied. "Amy and I are planing on going to the school dance that night." "How about you Chuck" His mother asked with a smile. "Unless you're going to the dance too?" "No," Chuck said dejectedly. "I wont be going to the dance but your company parties were never that much fun." "Too bad, I thought of the perfect costume for you too!" "What's that," Chuck sneered. "Head Nerd?" "Actually I was thinking more of Cinderella!" His mom replied with a grin. "Don't you mean Cinderfella, like that old Jerry Lewis movie?" Chuck asked suspiciously. His mother just smiled at him. "No I meant what I said - Cinderella, as in beautiful gown, glass slippers, handsome Prince, you remember it don't you?" "I remember that Cinderella was a girl, or did you forget that part?" "No, I remember it quite well, that's why I thought you'd enjoy it!" Chuck's heart was pounding in his chest, his mouth suddenly felt very dry and his palms very wet! He could see Jill looking at him then at their mother. Had she told? "Why in the world would I ever enjoy going to a costume party as Cinderella? Why not the Prince?" "I suppose you could go as the Prince but then you wouldn't get to wear a gown, some really pretty lingerie, makeup, slippers and things like that! I'm sure you wouldn't want to pass up a chance to get all dolled up, right?" Chuck was in a quandary, going as Cinderella would be a dream come true. But how could she know? Chuck wheeled around to face Jill, tears streaming down his cheeks. "You promised you'd never tell!" He screamed hysterically. "You promised!" "She never said a word Chuck, honestly." His mother said softly. "I figured it out by myself without ever asking her, I was confused at first but things made sense when I saw your feet sticking out of the blankets one morning. You must have forgotten to take the polish off the night before." "How long have you known," Chuck sobbed. "For a couple of weeks now. I wondered why I was finding almost twice as much of Jill's underwear in the wash and very little of yours. She also seemed to be going through a lot of other clothes and makeup. Once I saw the nail polish I knew." "I'm sorry mom," Chuck said, his voice trembling. "I promise I won't do it anymore. Please don't tell anyone!" "Calm down, I'm not about to tell anyone but I do expect you to tell me everything though." Chuck sat down along with his mother and sister and poured out his story from helping with the dress to wearing Jill's underwear almost daily. His mother stopped him occasionally to ask a question but never made any comment until he was done. "I don't believe that you'll keep your promise Chuck." She said quite solemnly. "I just don't see that happening." "I will mom, I swear I will!" Chuck cried. "I'll never wear girl's clothes again, believe me!" "I suppose you could try," His mother responded. "But I think you should know that from what I've read it's almost impossible to do!" "I don't care!" Chuck protested. "I can do it, I know I can!" "What if I said that I don't mind if you keep dressing up like a girl? Would that make a difference?" "Are you serious?" Chuck asked slowly. "You really wouldn't mind?" "I wouldn't have mentioned the Halloween party if I wasn't serious. Would you like to continue?" Chuck desperately wanted to say no, he wanted to be just like any other boy but it was too late, he was already hugging his mother and thanking her! "I take it you'll come to the party with me?" His mother asked with a knowing smile. "But wont people think it's kind of strange for your son to be Cinderella?" "Not if they were told that Jill was coming, not you!" Chuck was lost in a dream by then. He was picturing himself in a flowing white gown, stockings, and silky lingerie being whisked across the dance floor. "What are you thinking?" Jill asked. "You've got a weird look on your face!" "Oh nothing, nothing at all." Chuck replied, still caught up in his dream. He wondered what he'd look like when he was all dressed and made up. He could just picture the kind of dress he wanted, it would be a long white dress, flowing out from his waist in layers of sheer fabric. Underneath he'd be wearing the most beautiful long white slip he could imagine, with layer after layer of pretty lace attached to silky white nylon. He'd wear sheer white pantyhose, unless he could talk his mother into a garter belt and nylons. His panties and bra would be white satin trimmed with the prettiest lace! On his shoes would be a pair of white heels about three inches high, he 'd have to get them soon to practice walking in them! It was a dream he never wanted to wake from! "We'll pick your outfit soon Chuck," His mother stated, interrupting his dream. "Right now I'd like you to do me a favor." "Sure mom, what do you want?" A smile crossed his mother's face. "I want to see what my new daughter looks like all dressed up. Make up and the works, do you mind?" Chuck thought he was going to burst from happiness. "I'd love to! I know just what to wear too!" "Do you want some help Sis?" Jill asked with a grin. "No thanks Jill, I want to do this all by myself!" Chuck shouted as he ran for her room. Chuck already had his shirt off and his belt undone by the time he reached Jill's room and a moment later he was out of his pants and socks rummaging through her underwear. He picked out the satin panties and bra he had worn the first time he dressed in Jill's clothes, a full slip and the smoky colored pantyhose. He pulled his underwear off then quickly slipped on the panties and bra, delighted at the soft, silky caress of the panties against his skin. Slipping a few pairs of pantyhose in his bra he adjusted the straps to have as normal a bustline as possible. Sitting on the bed he slowly rolled the pantyhose up his legs then carefully adjusted them around his waist. He then lowered the slip over his head and adjusted the straps to fit the dress he planned to wear. His hands shaking he opened the door to Jill's closet, removed a pair of green pumps then slowly removed the green dress from it's hanger. Gingerly, he slipped the dress over his outstretched arms and pulled it into place. He slipped his stockinged feet into Jill's shoes and once again the feeling came over him that finally, all was right for him. He took extra time and effort to fix his makeup, eyeshadow in a dark brown to accent the dress he wore, light foundation and blush to blend in with his fair features, and a medium shade of red lipstick that he asked Jill to buy for him. He clipped on the earrings that matched his dress, added a gold necklace and bracelet, then fluffed and added a little curl to his hair. After taking one last long breath he went to show his mother. Jill was all smiles as he walked into the room. His mother had a slight smile that broadened as Chuck got closer to her. "You've had a lot of practice I see! " "I guess you could say that." Chuck replied shyly. "What do you think?" "I think you've been wasting you're time on sports, you're pretty enough to be a cheerleader!" "Thanks mom, it really means a lot to have you understand." Chuck's mother just smiled and nodded her head, she didn't really understand although she had read as much as she could find about such things these last few weeks. All of her research had led her to know that the best she could do was to make the best of things. As she had told him she found no indication that once a boy was deeply involved in cross dressing there was virtually no chance of stopping. In an effort to keep him from slipping away from her she would do her best to accept that her son had an uncontrollable urge to dress like a girl. She wasn't sure how it would work out but if he was going to dress like a girl she'd help him to be as feminine as possible. No one would ever know that the attractive young woman in the Cinderella costume was a boy! "You look very pretty in that dress Chuck but why don't you put on something more casual and we can talk about what's going on?" Chuck gave his mother a quick kiss on the cheek then went to get changed, carefully removing the outfit he had on before choosing another. In a few minutes he was back with his mother and sister. "Somehow I had the silly idea that you'd come back wearing boy's clothes!" His mother joked as she looked at Chuck wearing a yellow blouse with a denim jumper. "Whatever would make you think something like that?" Chuck asked, feigning innocence. Chuck, Jill, and their mother spent the next several hours talking about the changes that were about to take place in the family. Chuck would no longer have to wear boy's clothing except to school or anywhere else that he would be expected to be a boy. At home he would be permitted to dress as a girl but he'd be expected to act like a young lady. He'd be expected to keep his legs and underarms clean shaven and to wear his hair in a feminine style and to sit, walk, and even talk like a fourteen year old girl. Chuck happily agreed to the terms of his new life at home since he'd be able to dress up whenever he pleased but mainly to get to the next subject - the Halloween party! He couldn't wait to tell his mother all of the wonderful ideas he had for his costume! After listening patiently for several minutes as Chuck spoke of how he was willing to try on dress after dress to find just the perfect one and his preference for a garter belt and nylons to pantyhose his mother softly interrupted him. "Sorry to disappoint you but you're a little too young yet for garter belts and I've taken the liberty of picking out the dress for you. I saw it in a second hand store, the price was right and I really think you'll love it!" She then left the room for a few moments and returned holding a white wedding dress that as beautiful as Chuck could have hoped for! The dress had a full skirt made of several layers of Chiffon and lace over a Satin bottom skirt. A sheer section of the bodice extended from the high collared neckline to just above the bust to display a tantalizing amount of cleavage. The back of the gown closed by a row of small pearl buttons which seemed to catch and reflect the light from every angle. Chuck stood speechless in awe and stared at the dress, it was so beautiful that he just couldn't begin to describe his feelings for it. When Jill asked what he thought of it Chuck could only smile and shake his head. Just as he began to recover Chuck's mother showed him the elbow length white satin gloves he'd wear along with the Tiara she'd picked up at a costume shop. Overcome, all he could do was cry. The weeks went by with Chuck spending more and more time as a girl. He gave up trying different sports and spent his time learning sewing, cooking, and needlepoint. His mother styled his thick, wavy, hair into an androgynous style. For school he parted it and combed it into a relatively boyish style but at home a few brush strokes and he looked like a cute girl. The party was to be held on a Saturday evening and Chuck was a nervous wreck for the entire day. Finally it was time to begin getting ready starting with a perfumed bubble bath and careful shaving of his leg and underarms. After stepping out of the tub and drying himself thoroughly Chuck slipped on a white nylon negligee and peignoir set which his mother had insisted he wear to bed the past few nights to make him feel as feminine as possible. On his bed were a pair of lace covered satin panties with a matching bra that his mother had gotten from the same bridal shop as the peignoir set. He slowly removed his robe and nightgown then slipped on the panties and bra before pulling the shimmering white pantyhose up his legs and stepping into an ankle length half slip. By then Chuck's mother was knocking at his door asking if he was ready for her to do his makeup. He shivered with excitement as he followed is mother to her room, once his makeup was complete he'd have only to step into the dress and have it buttoned up. It took nearly an hour for his mother and sister to get Chuck's makeup right but once they were done there was little trace of the boy who lay beneath all the satin and lace. In his place was an attractive young lady who would most assuredly catch the eye of many a young man. Delicate pearl earrings were carefully clipped in place while a pearl necklace was fastened around his neck. Chuck couldn't wait to put on his dress but his mother asked him to wait a few more minutes while she sent Jill for one last surprise. While they waited his mother commented on his flat chest and how that it wouldn't look right in the sheer opening of his dress. Before he could nod in agreement she produced two small but quite realistic breast forms which she glued to his chest. Smiling, she told him that now things would look just perfect! Just as he recovered from the shock of having breasts, Jill returned holding a shoulder length brunette wig that ended in a cascade of loose curls. Placing it on his head the women adjusted it to get the best fit then removed several pieces of paper exposing tape which would hold the wig securely to his scalp. Once done with the wig the tiara was settled on his head and clipped into place. Finally it was time for his dress and Chuck's nerves were completely on edge. Jill held his arm as he delicately stepped into the gown and allowed his mother to work it up to his waist after which Jill worked the gown up further to allow him to place his arms into the sleeves. While his mother worked to fasten the dress in the back Chuck slid the white gloves over his hands and up his arms. A few minutes later the many pearl buttons were fastened and Chuck was helped into a pair of sparkling silver, three inch high heeled pumps which he'd practiced in for the past few weeks. Finally it was time for Cinderella to see how beautiful she looked for herself. The women removed a blanket which had been slung over a full length mirror then stood back to watch their now strikingly lovely son and brother admire the beautiful young woman he'd become. Chuck was amazed at how well his mother and sister had turned him into a pretty young woman. The dress fit him perfectly, his makeup was flawless, and he felt like a Princess! Tonight he truly was Cinderella! The party was the most exciting time in Chuck's young life. His mother's friends never doubted that they were looking at a sixteen year old girl nor did the many boys who sought after Chuck for dances and companionship. That night he won first prize for his costume but broke the hearts of the numerous boys who requested his phone number. He sweetly explained that he had just begun seriously dating a boy and didn't think it would be right to see other boys. The boy's mothers were impressed with the loyalty of the young woman although his mother was finding it hard not to laugh. As a boy, Chuck couldn't seem to get a date if he paid for it. Now as a girl, he had more requests for dates than his sister! That night at home Chuck recounted the thrill of the evening to Jill who sat enthralled by his stories. After reluctantly changing out of his costume into his peignoir set he tearfully thanked Jill for her help in showing him that he could indeed become the girl of his dreams. Seeing how happy Chuck was that night his mother vowed that whatever it took she'd keep him that way. There was the matter of a summer vacation coming up where a woman and two daughters could have a great time! After that maybe a private school for her daughters? (fin)