hey there you're looking kind of cute please consider subscribing and check out our patreon let's have some fun 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 parents 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 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 brother's 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 I did something wrong I thought we were having it was all my 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 his 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 war 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 eye shadow 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 15 to 20 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 end 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 ask 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 I don't mind it a big 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 my underwear 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 ask 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 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 homework 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 do 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 hemis skirt or model a new outfit to let her get
an idea of what she'd really look like in it occasionally they even pulled 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 planning 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 won't 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 a 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 a 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 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 won't 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 stalkings being whisked across the Dance Floor what are you thinking Jill asked you've got a weird look on your face whoa 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 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 makeup and The Works do you mind 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 thanks for watching check out patreon if you want to have early access to the other parts if not it will be online in a couple of days
