Dressing Up and Masturbating With My Sis

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CROSSDRESSING and MASTURBATING with my SISTER I started cross-dressing when my sister got a new all round knife pleated skirt and she was going round the house twirling that skirt and making the pleats fly right out at every chance she got. Well that really caught my eye and I could not keep my eyes off the way the pleats moved and swirled, it was just like they had a mind of their own.


It was some time later when I was in the house alone when that skirt came into my mind, don't ask me why, but I just wanted to try it on to see how it would look and feel on me. Well I slid the skirt up to my waist, fastened the button and zip then on looking down at the pleats, the skirt was poking out like a tent. I never knew about erections or wanking at that time and on lifting up the front of the skirt I found my willy to have grown very big and hard and I wondered what had happened to it and I was worried if it would ever go soft again. But I still could not resist giving the skirt a twirl just like my sister had done, I also loved spreading the pleats out, then I just walked about the house feeling every movement of that skirt and the magic way it moved. It really was lovely the way the skirt moved from side to side with every step, I then understood why my sister enjoyed wearing dresses and skirts; they felt so lovely and just looked so nice. I turned the skirt round to get the zip at the front then unzipped it and let my willy out the zipper which made the pleats hang and look much nicer. I was worried about my willy as it took ages before it went soft again but I took a whole lot more interest in my sisters clothes after that. Later I tried on her full skirted dress and petticoat and loved the way it made the skirt stick right out, then I gave the dress skirt the biggest twirl I could and I was hooked, petticoats are just so sexy and my sister and her friend were always trying to see who could get their skirts to stick out the most.


One time when I was wearing her dress I heard the front door open but I could not get the dress off in time as it was a dress with no back zipper but one that you put on over your head and I was not used to that. The only thing I could do was hide under my bed still wearing the dress and hope for the best, it was my sister, she looked into our room, but never saw me so she turned round and went right back out again. It took me quite a while to get the dress off, but it did give me such a fright, could you imagine getting caught wearing your sister's clothes. It was lovely to watch my sister wearing that same skirt and her not knowing that I had been wearing it just as much if not more than she was, but sadly I did not wear it for as long as she did.


One day my sister came rushing into the house very excited and told me that the boy next door had shown her his willy then she told me that he pushed the skin back and this thing popped out the end then he asked her if she wanted to try it and she told me it was great fun to push back the skin and make his thing pop out the end, but I never knew about what thing she was talking about as then I never knew my foreskin could go back, then she told me that she showed him her pee-pee as she called it and he had a very close look at it and said it was very nice. I was always very close to my sister and she was very excited at having seen the boys willy so I told her that she had never let me look at her pee-pee when without batting an eyelid she just lifted up the skirt of her dress, tucked it up inside the waistband then just slipped down her knickers and showed me her pussy then she spread her little pussy lips wide open and I was amazed, it was the first time I had seen inside one and it was so beautiful and very neat and she kept opening her lips very wide which made her pussy look quite big. Then she asked me if she could look at my willy, so I took my cock out and she could not get her hands on it fast enough but it did not get hard at that time but she had a very close look at it but she never tried to push my foreskin back, and at that time I never knew it could go back. It was then that the front door opened and our mother came in and my sister only just managed to get her skirt back down into place then she went into the bathroom to pull her knickers up properly.


Well my sister had got me so excited that when we went to bed that night we talked about the boy showing her his willy and I still never knew about what had popped out and she kept saying you know what I mean but I was that interested in my sister's pussy that I asked her if she would show it to me again. She told me she would love to show it off again then she just lifted up her nightshirt and rolled onto her back drew her legs up and spread her pussy wide open for me to look inside then I noticed two other smaller lips that joined together at the top and went out of sight so I asked her what they were for but she said that she did not know. It was then that my interest was drawn to where her pee came out so I asked her and she pointed to halfway down her pussy but I could not see anything and I thought she was kidding me on, but she said it was hard to see even by herself so I asked her if I could watch her do a pee and she said she would when it was safe but I forgot all about it as all I had on my mind was my sister's pussy and her lovely skirts and dresses.


I really did not think it was fair that girls had such lovely clothes to wear and also such a choice of styles when us poor boys had only trousers to wear or until I wore my kilt on a Sunday which I really enjoyed and I got to wear a pair of knickers under it, but it did put me on a level starting point with my sister's skirts as I was taught to smooth down my kilt pleats before I sat down so that came naturally to me. Later that week my sister was wearing that all round pleated skirt that I liked so much and I did so want to tell my sister that I liked her skirt, so I plucked up the courage and told her that her skirt was very nice and sexy but never in my wildest dreams did I expect what she said next, she asked me if I would like to try it on which left me quite speechless as I never thought for one second she would ask me that. Much as I wanted to try on that skirt again then wear it in front of my sister, I just could not bring myself to say yes. I told her that boys did not wear skirts but she said it did not matter and she would like to see me trying her skirt on, then she promised she would not tell anyone and it would be our secret, you never know you might even enjoy it and you have sort of worn a skirt with wearing your kilt, so I said ok and she unbuttoned her skirt slid the zip down, took it off and handed it to me then she went into our bedroom and slipped into her kilt. I pretended to be shy and told her I did not know how to wear it then she told me to take off my trousers then she made me step into the skirt, pulled it up and fastened it, telling me that most skirts fasten to the left hand side then it happened, I got hard again. There I was wearing my sister's pleated skirt standing in front of my sister with the skirt sticking right out in front so I covered it with my hands when she asked what was wrong and I said, Wearing this skirt has made my willy hard and she asked if she could look at it. I took my hands away and the pleats were pushed right out by my hard willy, she asked me to lift up my skirt and told me that now you know that wearing a skirt gives you such easy access to your willy and you only have to let go of the skirts and they fall back into place. I slowly lifted the skirt up and my sister took down my underpants then my willy sprang up and her eyes nearly popped out her head, she told me to sit next to her but remember to smooth the pleats under you like I do before you sit down, it keeps the skirts pleats looking nice, I said that when I wear my kilt I always smooth my pleats down before I sit. I dropped the front of the skirt and smoothed the pleats under me as I sat down then my sister lifted up the front of the skirt to expose my hard willy then asked if she could hold it and I said ok. My Willy was so hard when she held it then she did something that I never knew about, she pushed my foreskin down quite hard and the tip of my knob came part way into view then I stopped her going any further as I had never even seen my knob before or pushed it back before, I thought she had harmed it as my foreskin was very pointed at the end and I thought the hole in the end was just for peeing with, also I was frightened but I just told her that I was shy. My sister told me again that the boy next door had pushed his skin back and that he had let her push his foreskin right back and it was alright so I let her hold it again and she slowly pushed my foreskin right down behind my knob which was by then fully exposed for the first time and by my sister as well, I was amazed but I never knew it could go back that far and it felt quite tight, I pretended that I had pulled it back many times before but I was more interested in seeing my knob than my sister was, then she touched my exposed knob and it was so painful and when she tried to get my foreskin back over my knob she could not, it was stuck behind my knob but as it was not sore I just left it there and my sister told me to leave it there as it should go forward again when it goes soft. It was then she saw my balls and asked what they were for, but I did not know then, so she asked if she could hold them and I said yes, but be gentle so she cupped her hand round my balls and squeezed them just too hard and I pulled back and told her just to play with my willy. After my sister had played with my willy for quite a while I asked her if I could play with her pee-pee and she said of course you can then she stood up reached up under her kilt and slid her knickers off then she sat down smoothing her pleats under her as she had told me to do then she lifted the front of her kilt up. She then lifted her legs up and spread her legs wide apart so I got off the couch to sit in front of her when the front of my skirt fell down and the skirt was rubbing on my newly exposed knob which was still very hard and very very sensitive which made me squirm and my sister asked what was wrong and I said that the skirt was rubbing on my willy and it was very tickly then she just reached over and rubbed the skirt against my bare nob and I nearly passed out with my first ever orgasm, a dry one but I did tell her it felt so nice when the skirts pleats were rubbing against my bare knob. But there I was kneeling in front of my sisters pee-pee and I asked if I could open it up this time and she said yes so I spread open those lovely pink lips and there were so many things inside and I again saw the smaller pair of lips that disappeared under a sort of cover or hood so I tried to pull it back to see inside when my sisters legs began to tremble then she told me she gets very excited when she gets touched there, so I put my finger on the top of the hard bit and rubbed it and before long my sisters hips were bucking up and down then she grabbed my hand which was so wet by then and asked me to stop, but as I tried to touch it again she said to leave it for a minute as it was very sensitive to touch just like your willy was when it was rubbing on your skirt, but at that time I never knew girls could get an orgasm, in fact I never knew what an orgasm was before that day. We both stood up and our skirts dropped down into place except my skirt was still sticking out with my still hard willy but my sister wanted to kiss so I held her and she pushed hard against me making the rough material of my skirt rub against my still bare knob then she reached down and again rubbed the pleats against my willy and I came again but this time I ended up on my knees on the floor as I nearly passed out then my willy went soft and my sister was laughing at how her just rubbing the skirt on my bare knob was having such an effect on me but my knob was very sensitive and she knew fine well what she was doing and the effect the skirt was having on me. We both sat down and my sister lifted up my skirt and seeing my willy was soft she tried to get my foreskin forward again but every time she touched my knob I jumped which she found very funny, but we managed to get it forward between us.


It was getting near time for my mother to get home, so I told my sister that she was right, I really enjoyed wearing her pleated skirt, and I would like to keep it on, but I better take it off before our mother gets in as I do not want to be caught wearing your skirt, then she said she loved seeing me wearing her skirt and I could wear it again any time. Well after that day I took a lot more interest in my cock as thanks to my sister that was the first time I had seen my knob and I spent every minute I could wearing my sisters skirts and pushing my foreskin back and forward as many times as I could so I could look at my new found knob and I could not stop touching my bare knob or rubbing the pleats over it just as my sister had done. I never told my sister that I had been wearing her skirts and dresses before she dressed me up, but I told her that I loved wearing that skirt in front of her, in fact I loved seeing us both wearing skirts together and I told her that it's a pity we could not wear the same skirts at the same time and she thought that's a great idea in fact we could play dress-up together like real sisters do. My sister and I used to dress up together at every chance we got and I never tired of trying on every skirt and dress she had, in fact I started picking out the skirt or dress I wanted to wear myself and I always looked forward to when my sister got a new skirt or a new dress as she could not wait to show them to me, or ask me if I liked it or if I wanted to try them on, but I always wanted to try on her clothes.


My sister used to ask me what skirt or dress I liked the best and I told her the all round pleated skirt that I wore before, also I told her I liked her gymslip but she could not understand what I liked about it and I said I loved the deep pleats and the way they opened and closed and it looked nice, also I told her I loved her full skirted dresses with a full petticoat underneath but I did tell her that I liked pleated skirts the best as pleats give a skirt such ease of movement with style.


The next week I came home from school my sister had laid out her gymslip and a full skirted dress and petticoat, and then she said which one do you want to try on first, and as I like pleated skirts best, I said I would love to try your gymslip on first. I could not get my clothes off fast enough and by now I was not shy at showing my willy off then my sister slipped the gymslip over my head but I will never understand why they have buttons on both shoulders as my sister was able to slip it easily over my head with the buttons fastened. My sister said that most girls undo the buttons then step into their gymslips, pull them up and fasten the buttons. I thought it looked so lovely and I could not stop playing with the pleats on the skirt and stretching them right out and I knew to smooth the skirts under me as I sat down. It was just so lovely to walk about in that gymslip and feel the skirts swirling round my legs and watch the pleats open and close as I walked about. I had tried on that gymslip and her other dresses and skirts so many times when my sister was not there but it was even better when I was dressing up with my sister and her giving me a helping hand or her picking something for me to try on.


My sister must have been talking to her friend about willies and how to wank boys because she sat me down and lifted up my skirts and as I was naked under the gymslip she grabbed my willy and said I have something to show you and she proceeded to rub my foreskin up and down, I wondered what she was doing but before I knew it my willy got very hard and my nob was poking out at every stroke but at that time I never knew how to get it hard even when I wanted it hard, but here was my sister showing me how to get it hard. I was amazed and then that lovely feeling started, I told my sister I want to pee but she said don't worry and she kept on wanking me and I was now holding my skirts up with excitement or in case I would pee on them, then it happened I had the most fantastic orgasm then I sprayed white stuff all over my sister's lovely gymslip and I felt terrible at getting her gymslip dirty, then I thought she would be mad and I told her that I did not know what happened and I'm sorry I got your gymslip dirty, but she said don't worry, it's called spunk and I will wash my gymslip before mum sees it. Well my sister took off my gymslip and put it in the washing machine but she was still not finished with me and asked me if I would like to try and do it again as she wanted to watch my spunk coming out as she had missed it, so I said yes, she wiped my willy clean and went to get the dress and petticoat. My sister said that I was to be careful not to get her dress dirty this time or I would need to wear an underskirt or a pair of her knickers to keep her dress clean but I said I loved wearing her clothes and I would do my best not to get my spunk on them.


She put the petticoat on me first then slipped the dress over my head then down over the petticoat, I was always amazed at how much further my skirt stuck out when wearing a petticoat under it then my sister asked me to give her a twirl which I felt embarrassed at doing in front of my sister, but she gave her skirt a twirl for me then I could not resist copying her and giving my own full skirt a big twirl, it was fantastic, the way the full skirt flared out as I spun round, after that, I was never shy at twirling my skirts for my sister, then my sister asked me to sit down. I told my sister I did not want to sit down in her lovely dress in case I crushed the skirt so I got the foot stool and held my skirts out at the back and sat on my bare bottom then I spread the skirts right out all around me which made the dress skirt look even better. My sister asked me if I would wank myself like she showed me and make myself cum then she would show me her playing with herself, so of course I said yes, but this time I was to tell her when I was about to cum then hold my foreskin right back and she would catch my spunk in a tissue.


Well as my foreskin was still back, my nob was rubbing on the stiff material of the petticoat and was nearly hard already so I stood up, lifted my skirt and petticoat up and held them up with my left arm then I pushed my foreskin forward with a bit of trouble and started wanking myself with my sister very excited watching me until I told her I was about to cum but she could not get the tissue in time so she grabbed a towel and put it on her knees, just in time to catch my spunk as I pulled my foreskin as far back as it could go, and came all over the towel and I did not get a drop of spunk on her dress but she wiped my willy clean which was really sensitive now then she pulled my foreskin forward for me then I dropped my skirts and petticoat back down then smoothed my skirt down. Getting my sister's gymslip dirty with my spunk was the one and only time I got any of her clothes dirty and I did feel terrible afterwards but I really wanted to keep all her skirts and dresses as nice as possible and I always took good care of them and my sister trusted me as well.


When I found out about wanking I started wearing my sister's clothes even more on my own but I was careful not to get her skirts dirty so I would hold my foreskin closed when I came then pee down the toilet, I told my sister that little trick later on so I never did have to wear knickers or an underskirt so when my sister came up behind me and put her hand up my skirts she had easy access as did I when she left her knickers off which was every time we dressed up together. My sister just loved dressing me up and fussing with my skirts to make sure the skirts hung properly and looked right and she made sure I did the same when we were dressing up together. When I still had the dress and petticoat on my sister said her friend had shown her how to masturbate and she wanted to show me, so she sat down in front of me and lifted up her skirt. She was not wearing any knickers under her skirt as usual then she slid one finger between her little lips and started rubbing up and down and before long her slit opened up just like a flower and something was sticking out from under her hood and I asked her what it was. She stopped rubbing and told me that that was her little stiff and it gets hard just like your willy but it is very sensitive just like your nob, so I asked her how far can you get your little stiff out and she used two fingers to pull her hood right back and her little stiff just popped out, just like my nob does when my foreskin is pulled back. I put my finger on her fully exposed clitoris and she pulled back right away and told me that it was much more sensitive than touching your exposed nob, but my nob was getting far less sore to touch and I told her this as she always loved retracting my foreskin and touching my nob.


When I was close to my sister's pee-pee I saw a small hole at the bottom of her lips and asked her if that was where your pee comes out and she said no, it comes out that tiny hole just above that hole but I could not see another hole, so I asked her what the bottom hole was for and she said her friend had told her that is where babies come out but neither of us believed it at that time. My sister said her friend had showed my sister her own hole and she had put three fingers in it, but when her friend tried to put her finger into my sister's hole she had trouble getting even one finger in at first, but her friend kept on trying and pushing until she finally got one finger in, but my sister's hole did not look big enough to even put one finger in but she told me again that her friend had managed to put her finger in her hole and she had put her own finger into her friend's hole and her friend asked her to put more fingers in her hole. I asked if I could try to put my finger in her little hole like she said her friend had done, she said that I was not to be rough, and don't just force it in and to do it slowly and make sure my hands are clean. I started to put my finger in when my sister told me to wet my finger or it will be sore so I dipped my finger in the slippery liquid coming out her hole and put it at the entrance to her little hole and started to push it in very slowly but it was not going in. I was really amazed as I was starting to push harder her little hole suddenly opened right up and my finger slid right in, it was just so elastic, then my sister asked me to leave it in for a minute until she gets used to it as it feels quite tight.


I waited until she told me that it was ok then I pulled my finger back until it was nearly out then I pushed it back in again; once I had one finger in for a while it went in far easier. A clear liquid was running out which made her hole very slippy then I tried using my other finger at the same time on both sides to stretch open her hole gently so I could look inside, when my sister said it was getting very tight and a bit sore, so I stopped and slipped one finger back inside her and started pushing it in and out. I watched my sisterâ......s legs tremble as I pushed my finger into her hole but I was really amazed at every time I took my finger out, her hole closed right back up again and you would never think that you could get your finger into such a small hole then again I put my finger at the entrance to her small hole and pushed and again it opened right up and my finger slipped in again then she said that she wanted me to make her cum. I never knew then that girls could have an orgasm so this was something new for me and I was very excited. I sat down in the chair still wearing my dress which made the skirt lift up at the front with the full petticoat so I held my skirts down and my sister sat on my lap facing me with one leg either side of mine, then she told me to rub her hood over her little stiff as her little stiff was much too sensitive for direct touch. So there I was rubbing her little stiff and my sister was moaning away when she asked me to put my other finger into her hole again which was so wet by then that it went in so easily, then my sister lost all control and had a huge orgasm then she grabbed my hand and told me to stop as her little stiff was too sensitive to touch but I felt the most amazing contractions on my finger that was still in her hole, it really clamped down hard on my finger then when her orgasm finished my finger slipped out so easily and I felt her hole close back up again.


When my sister stood up the back of her kilt was soaking wet from the amount of liquid that had come from her hole then she got a tissue to wipe her pee-pee clean when I said let me wipe yours clean as you wiped mine clean so she gave me the tissue and I wiped her clean but she jumped when it passed her little stiff and I knew that feeling when my sister had touched my nob after I had my orgasm. I asked my sister if she played with herself and she said she did but only after her friend told and showed her how to masturbate then I asked her if she puts a finger into her hole and she said she sometimes puts the tip of her finger in and sometimes she puts the handle of her hairbrush into her hole but her friend puts lots of things into her hole but her hole opened up much easier than mine and she was always wanting more of my fingers pushed in.


My sister said she needed to pee so I reminded her that she said she would let me watch her pee and she said she would love to pee for me so we went to the toilet and my sister flipped up the back of her skirt and sat down on the toilet but I could not see where her pee was coming out from so I told her to stop peeing which she did with some difficulty as she was bursting. I told her I wanted to see where it comes out and she said to go and get a bowl from in the kitchen sink then my sister sat on the very front of the toilet and spread her legs open then she opened up her little lips of her pussy and told me to catch her pee in the bowl but said to hurry up as she was bursting to pee. I was holding the bowl below her pee-pee not knowing what angle her pee would come out when my sister's pee started gushing out and it was a flood and when it hit the bowl it splashed up onto my face which made my sister laugh but then with her pee gushing out I saw the hole her pee was coming out from and it looked quite big as her pee widened the hole but I was really surprised how strong her pee came out and for how long it lasted. When she stopped peeing her pee-hole seemed to disappear and was hard to see just as my sister had said but now I knew where her pee-hole was then she got a toilet tissue and wiped her pee-pee dry and when she stood up I said now I have watched you pee do you want me to pee for you and she asked if she could hold it for me and I said ok. I lifted my dress and petticoat up out of the way and my sister held my cock then she pushed back my foreskin and said you can see your pee-hole so clearly when mine is very hard for me to look at, I told her to point it down the toilet and I started pissing then I told her that she has a very strong piss, far stronger than mine and she said you can hold and point yours but I cannot then I said that she could pee far further than any boy I know. I finished peeing and my sister wiped my nob clean and asked me to leave my foreskin retracted so she can look at my nob later then I dropped my skirts down and we went back to our room, I kept the dress and petticoat on for a long time that day and I enjoyed every minute and said that I was sorry that I had to take it off when my sister took off her kilt and put on the dress I had been wearing saying that she wanted to wear it after me then I told her that she was so lucky to be able to wear such nice dresses and skirts whenever she wants and I told her she looks lovely in that dress and I would have loved to be able to get up in the morning and wear it all day to which she replied that I can wear it again another day.


My sister came over and sat in my lap and I could not stop myself pulling her hemline down for her and smoothing her skirt down then I told her that it was lovely knowing that just a short time ago I had been wearing that lovely dress and it felt so lovely and right wearing it. My sister loved me trying on her clothes as I always looked after them like they were my own and she knew it. As she grew older she kept her old gymslip for me and some of her dresses and skirts and one time my sister got a new grey box pleated school skirt and as she knew I liked pleated skirts she asked me if I wanted to be the first to try it on and of coarse I said yes it will be a privilege, so I put the skirt on and strutted round the room modelling it for her and I thought it looked fantastic and had lovely pleats, in fact it was the first time I had worn a box pleated school skirt, and it looked better than her all round knife pleated school skirt. When my sister came home from school she always teased me by spreading the pleats out and playing with her skirt and asking if I wanted to wear it when she took it off, but my mother was usually about so I had to make do with thinking about wearing my sister's new box pleated school skirt. My sister was never shy at showing off her pussy and I could look and play with it any time I wanted and she would often remove her knickers to surprise me or if she was wearing a straight skirt she would make it tight by spreading her legs to show off her pussy.


My sister also said that she liked looking up my skirts to see if my willy was soft or hard and wearing skirts or dresses made it easy for her to play with my willy and that she liked slipping her hand up my skirts to hold it as well. I let her take out my willy whenever she wanted although it was far easier for her to play with my willy when I was wearing a dress or a full or pleated skirt and if I was hard she would lift the hem of my skirt and sit it over the top of my willy then the first thing she would always do is push my foreskin right back behind my nob then tell me to leave it there until she gets it forward herself which at first was quite hard but it soon stretched and of coarse she was always interested in getting my willy hard and I was always wanting to open her pussy and spread her lips open wide but the best thing was watching her little hole close up after I took my finger out. When we were dressing up together we never thought about trying to put my cock in her little hole and I wonder what would have happened if my sister had asked me to put it in her little hole, but at the time we never thought about doing that. I remember one time we were going to church, my sister in a nice tartan pleated skirt and me in my kilt she said why don't we leave our knickers off? and I said ok but in church I had my jacket over my knees and my sister put her hand up my skirts and got my cock hard so much so when I stood up my kilt was sticking out at the front like a tent which amused my sister and I had trouble hiding it without my knickers keeping it in place.


I loved wearing my kilt on Sundays also I loved the swing of my kilt with it's deep pleats and I knew it would not blow up to reveal I was not wearing my knickers but still I would rather have worn my sister's tartan pleated skirt as you could see the pleats at the front also I could turn the skirt round to get the zip at the front and take my willy out without lifting the skirt up and my sister loved that as the skirt hung properly. I used to let my sister wank me this way when I was wearing a really nice skirt then when I was about to cum ,I told her and she held my foreskin closed and it filled up with my spunk thus keeping the skirt clean then I would take off the skirt with my sister still holding my foreskin shut and she only let my foreskin go after it had ballooned up with my pee then bursting down the toilet The other thing that we enjoyed together was watching her breasts grow from tender little buds to a lovely full pair with jutting nipples but when her breasts started growing my mother moved my sister into another room saying she needed her own space but my sister did not want to move. But we still checked out her breasts every day to see if they had stopped growing and I would sit behind her holding her breasts in my hands, telling her that I wished I had breasts just like hers and she loved it. Then her pussy grew hair which my sister hated and it was hard to see her slit anymore.


Then years later my sister rushed in to tell me that she was wearing stockings and suspenders and I must try a pair on as they feel so lovely but I was not so sure but my sister told me to take my trousers off then she pulled one on me and the feeling was incredible so much so I told her I wanted to wear them under one of her skirts or dresses. It was quite hard the first time I wore stockings as I had to learn how to fasten the suspenders especially the ones at the back, but now I am as good as any woman and wearing them feels so cool under my skirts and dresses or wearing them under my trousers and sometimes my sister would check for the tell tale signs of the suspenders My sister really surprised me next day by introducing me to a new found love, her new sunray pleated skirt and as I had never seen that type of skirt before I thought it looked so beautiful that I could not get that skirt on fast enough, and with the cool feeling of the stockings under the skirt and the way those pleats moved and swirled round my legs,I was on cloud nine then I spread the pleats right out to see just how full the skirt really was then my sister said that I could find the skirt in her wardrobe anytime I wanted to wear it, and I wanted to wear it a lot, funny thing is I never could sit down in that skirt unless it was on a footstool so I did not sit on the pleats as I did not want to get them crushed but sat on my bare bottom with the pleats spread out all around me.


Fourteen years I had worn that sunray pleated skirt and it was still as good as new and now I am over sixty and my love of wearing skirts and dresses has not changed, if anything it has got worse and I still like my willy to hang free under my skirts. I bet the number of boys that tried on their sister's clothes especially schoolgirl uniforms is really high but not many people would admit to it, I only admitted to it to my mate after he told me when he was drunk that he had tried on his own sister's school uniform to see how it would look and feel on him, but when he was sober he was embarrassed when I told him what he said, until I plucked up the courage to tell him that I had done the very same thing as he had done and I told him that I had wanked myself when wearing her skirts, but I never told him I dressed up with my sister. Then we talked openly about what sort of clothes we had both tried on and which ones we liked the best which was box pleated school skirts and full circle sunray pleated skirts, but we never dressed up together.


What happened between my sister and I started when we went to my sister's friends house and as we were at the bottom of the stairs her friend started kissing her brother who was younger than her and he was touching her pussy through her skirt and fondling her breasts but we were shocked and did not know what else they did but I think she was the one who told my sister how to wank me so I think she was masturbating her brother,we went home and talked about what we had seen and I said would you like me to kiss you like that and she said yes but I never got to even look at her pussy then and only got to touch her very small breasts once then as she said, they were growing and were very tender so that was that until she came rushing in to tell me that the boy next door had shown her his willy, she was really very excited about it and the rest is history. I don't know if they had sex together but my sister and I never did go that far and as much as I can tell my sister never told anyone about me wearing her skirts and dresses but she said she would have liked a sister and I think I took that place as she wanted me to dress up with her as much as possible and for as long as possible. My sister told me that that girl was the girl who first showed her how to masturbate by masturbating in front of her and also she showed her where to put a finger inside her hole by doing it to herself first and that she got three fingers into her own hole but she said the first time her friend tried putting a finger inside her little hole it was very tight and my sister said that she did not think her friend would get her finger in her little hole and was about to stop her trying when after a bit more pushing, all of a sudden, her finger went in and my sister was hooked then her friend told her how to masturbate her and she said that her finger went into her friends hole much easier than her friend got her finger into her own hole but it did get a bit easier each time her friend put her finger in and when they were fingering each other they always kept their dresses on with their knickers off so they could just push their skirts down or stand up, letting their skirts fall down into place just in case someone came in.


My sister also told me that when she got home after visiting her friend that day she sat down and for the first time ever she tried putting her own finger inside her own little hole, and she just got her finger in when I walked in and caught her messing about under her skirt. My sister told me later on that when her friend showed her how to masturbate by masturbating herself in front of her that she had a huge little stiff that looked like a very small willy and that she liked my sister to play with it by pushing her foreskin, as she called it as far back as possible then rub her bare stiff, but my sister did not like her little stiff played with in the same way as hers was very sensitive and her friend always wanted my sister to see how many fingers she could get into her hole as she said it felt nice and tight. I will always remember my sister's friend as she always wore the most beautiful dresses which showed off her lovely big breasts and her skirts always stuck out more than any other girl in the street and when she bent over she always gave a good view of her lovely full petticoats and her very large firm breasts, I even told my sister that I would love to try on some of her dresses to which she replied quite angrily, you know fine well you can wear any of my dresses anytime you want, she just has more petticoats under her skirts. My sister told me later that her friend once removed her bra and her breasts instead of sagging down, they sprung up into the air and gave that magic wobble as she walked about her bedroom.


I have been married over 40 years and my wife knows about my cross-dressing as I told her soon after we met and she buys me dresses and skirts whenever I see one that I like, but sometimes the dress or skirt I love is being worn by another woman and I would love to ask her where she got it. On our wedding day my wife was given a lovely tweed skirt suit as a going away present but when we got to our hotel I noticed she was not wearing it and I asked her why and she said she did not like it, but I said it was very nice. Then she just said well if you like it then you can wear it as I don't want it, so being quite tipsy I said ok then I will and I slipped on the skirt, it was the very first straight skirt that I had ever tried on as I never really had any interest in straight skirts at that time but it felt so different to wearing full or pleated skirts also I found it very restrictive but at the same time it felt so lovely when I spread my legs or walked about it made the skirt even tighter but it was easy to move in as it had a small deep single inverted pleat at the back, even my wife said that the skirt looked nice on me, so that was the first skirt suit that I owned. In the morning when I woke up I thought I was caught up in the bedclothes then I discovered that I was still wearing the skirt that I had put on the night before, much as I would have loved to wear it all day I knew it was not possible so I took it off and put on my boring male clothes.


I never try and pass as a woman and I am not gay and have no sexual interest in men, I adore women, I simply love the look and feel of some woman's clothes also most women nowadays don't know what being feminine is all about, with them wearing jeans or trousers, you hardly ever see women in skirts or dresses these days. I wish the fashion of the 50's would come back as full skirts and petticoats were so lovely and I am so glad I was there at the time to enjoy them. Last and much more important is that I have talked to a lot of ladies about their pussies and there are very very few that think that their pussies look nice but they are really beautiful and they should enjoy them and be proud to have one and to show them off. I always call my wife's vulva her flower because that is what it is, a beautiful flower. My own thoughts about them is that women cant see their own pussy properly without using a mirror and they rarely touch them to pee except for wiping them dry after, so they rarely give them a second thought but they do worry a lot about their smell which I think is lovely. The first thing I notice about a woman is what she is wearing, I never give a woman wearing jeans or trousers a second thought, but if she is wearing a nice dress or skirt I always think about what it would be like to try it on and go out for a walk. Hugh.

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