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Permanent Sissy

I have been crossdressing for years now not known to my mother (or so I thought). she is the only person I live with at the moment. when she was going to be out for a few hours I went to her underwear drawer and inside was the most sexy, silky, feminine underwear set I had ever seen complete with calf length stockings and a garter belt. I wasted no time stripping off and sliding on the sexy underwear, next I found her makeup bag and applied some red lipstick and black mascara. that was when I heard the front door open, my mum was home early!! I tried to hide but before I could she strode into my bedroom and said "well what do we have here" I whispered "mum, I like wearing girls clothes" "well of course you do I've known for years and I've been preparing for this day, I came home early on purpose just to catchmy little sissy son and I left that underwear which you seem to be enjoying at the top of my drawer on purpose as well" "come upto my room in 5 minutes panty boy and don't you even think about taking off your new underwear or makeup. I did as I was told and after 5 minutes I knocked on her door with shaking hands. "come in prissy sissy" I heard from inside. I went in and the first thing I saw was a bright pink nightgown covered in lace. "don't worry sissy you will be wearing that soon enough" she said when she saw me staring at it." now since you are so desperate to become my little girl I will fulfill your fantasy" I opened my mouth to beg her to let me go but she put her finger on my lips and said "ssssshh sissy you don't want to smudge your lipstick that you applied so perfectly" "now slip this gown on and slide into bed its long past your bed time little girl" I did as she said and put on the gown, I have to admit I loved the feel of the silk rubbing against my bra, it was heaven. I then got into her bed and lay down that's when she put her hands on my wrists and held them against the bed then put her legs on my chest to completely pin me to the bed." you see sissy, I have done my research and I've found out that once many crossdressers have jacked off they suddenly hate girls clothes and want to get out of them, this is what I am going to use to teach you a lesson prissy sissy. she then slId her knees of my chest and put her hand underneath my gown an panties and pulled out my ****. she then started rubbing it and whispering in my ear "*** sissy" "*** for me" "*** for mummy" "be a good girl and *** for me sissy" she rubbed faster and faster until I covered her hand and the bed sheets in *****. "good girl" she said. "now get in the shower and wash off all this horrible man juice we are going to have some fun sissy" I got up and showered quickly I wanted this nightmare to be over as soon as possible. "good job now go and sit down in that chair" I tried to reach for a towel but she said "no I don't think so sissy" she could see I was embarrassed about being naked so she said "I wouldn't worry I can barely see it anyway" "you have seen some of the toys I have for you to play with but now lets see my favourite one" she walked over to her wardrobe and pulled out a long black box, she opened it and showed me what was inside, I was absolutely terrified. it was a long black leather riding crop, I instantly tried to curl up but she said spread your legs sissy. "no please don't" I begged. you must obey! I spread them and she brought the crop down as hard as she could on my ****. I screamed with pain. it was the worst pain I had ever felt in my life. "I am your dominatrix, I am your mistress, I have the power to cause you immense pain whenever I want and from now on you will obey my every command" I nodded and she whipped me again. "Say YES MISTRESS!" "yes mistress" I yelled " better sissy now you have learnt who is in charge and now the fun can begin!" "now go and run yourself a bath you need to remove all of that disgusting man hair. I went to the bathroom and ran a bath. once I had finished she said get in, then she handed pulled out a razor from her cupboard and said "say goodbye to your manhood prissy you are a young lady now. she then shaved my legs completely bare and then moved onto my chest, back and balls. I began to cry while she removed every single one of my pubes and she said "don't cry prissy I'm giving you exactly what you wanted, I'm turning you into my girly girl. after the shaving she pulled out some red nail polish and painted all of my fingers and toes then I had to watch her as she tipped all of her nail varnish remover down the sink which was my only chance of everyone not knowing i was a sissy. then my mum said" now for my favourite bit of your sissification, choosing your underwear, it will have to be something sluttish beacuse I no what a naughty girl you are" "let's see perhaps we will go for a similar set to the one you were wearing earlier beacuse you so obviously loved that set. "I think we will go for these first" she pulled out a pair of black stockings with a flowery pattern and a matching black garter belt. "the most important part of your feminization is that I don't put any of these delightful clothes on you, you will put on all of this yourself because you wish so much to be my little pink princess. she walked around me with the whip stroking my skin with it and rubbing my **** with it. I pulled the stockings up my legs one by one and as each one slid up my legs she kissed my neck softly and told me what a good girl I was. "well done sissy now it's time for your lacy panties which I know you have been just dying to wear. "answer me sissy" "thankyou mistress for giving me these lovely panties to wear" I said."well done, now just slip on the garter belt and fasten the clips and we can move onto your bra. she picked up the bra and slipped it over my arms and fastened it at the back, that's when i heard a small click and looked round."oh don't worry sissy I'm just putting a padlock on your bra so you never ever ever have to take it off."and now we have the best part, your brand new outfit..." she pulled out from her wardrobe a French maids outfit from victorias secret and I began to beg that I had learnt my lesson and I was a boy. "of course your not a boy, boys have pubes don't they and it looks like you don't have any so your my special sexy beautiful girl arnt you sissy?" "now enough of this nonsense I need to put on your new dress. knowing I was defeated I stepped into the outfit and cried as it was zipped up and the padlock was put on and I was sealed into femininity."that's it sissy you are now a girl you can never go back you are and always will be a girl." "now just a few more things and you will be the girl you always wanted to be. she took me to her wardrobe and pulled out some red 4 and a half inch heels and slid them onto me." why do they feel wet" I asked. "oh that's just the superglue setting and don't you dare try and take them off". "let's move onto your hair now so you already have beautiful shoulder length hair so let me just put it in a more girly style for you. "and finally its your makeup, now pout your lips sweetie and i will apply the lipstick. I kept them tightly shut so she held my nose until I had to open my mouth and she grabbed my lips and smeared lipstick all over them. "and now you really are my special little girl and since you are also my maid I have some jobs for you to do" "the first is to clean the entire house, you can start in the living room, now come downstairs with me and I will show you exactly what I want you to do" I went downstairs first but it was hard in the heels and I kept wobbling but my mum just said "stop being silly princess I no you can walk in those heels you have worn mine enough!" when I reached the living room I opened the door and my mum pushed me onto the floor really hard. when I looked you realised why. sitting on the sofas were my aunt, my grandma and my girlfriend. they screamed with laughter at me laying on the ground helpless. they took loads of photos and using the whip my mum forced me into posing for the camera. she made me suck on my finger and pout my lips at the camera, and stroke my legs. she made me say stiff like "ooh I've been a bad girl" and "I'm such a naughty sissy" and each time they laughed hysterically. mum handed the whip to each one of them and one by one they bent me over and whipped my *** as hard as they could. then they found a permanent marker and wrote SISSY in huge letters on my forehead and my chest. then my girlfriend said has our little sissy got a name yet?" and my mum replied "no good idea can you think of one?" my girlfriend thought for a bit then said "well since her old disgusting boy name was Charlie how about we call her Charlotte?" "that's brilliant! do you like that charlotte" I didn't answer so my mum grabbed my chin and forced my head up and down and said "yes charlotte does like her new name" then my aunt said "well it looks like Charlotte is getting very excited, can you see her erection under all those petticoats?" "yes I can" my mum said "and we now how to fix that don't we Charlotte?" she grabbed my **** from underneath the dress and began rubbing it and once again she was saying "*** for me" "*** for me charlotte" "be a good sissy and *** for me!" I couldnt resist and again covered her hand in ***. "wow I could barely find it it's so small!" she showed my **** to my girlfriend and aunt and grandma and they said "haha it's so tiny we can barely see it!" once that was over my mum said "I've got bored of this now let's see how Charlotte likes showing the world how pretty she is" mum and grandma grabbed my arms and my aunt and gf grabbed my legs and together they carried me into the back garden. my mum picked up a nearby chair and ordered me to sit on it. I did as I was told and they then tied ropes around my arms and legs and tied me to the chair. my mum then got some pink panties out of her pocket and forced them into my mouth, then used tape to secure them so I couldn't speak. one by one the neighbours came up to the fence and asked who the pretty young lady was, then my mum told them everything that I was her son that liked wearing her clothes and she was teaching me a lesson. they all laughed and jokingly told me off for being a bad girl. I was totally humiliated and had become completely submissive to my mum, I was now her sissy plaything and there was no point trying to fight it. after a few hours they took me back inside and sat me down on the sofa. my mum then said "now you have learnt how it feels when people know you are a sissy, however this must happen a lot more for you to learn not to wear girls clothes. I have decided that for every piece of my clothing or possessions you were wearing when I caught you, you will spend 1 month wearing only your new sissy outfits, that includes to school, at home and anywhere else. now let's see when I caught you you were wearing my pantyhose, my bra, my panties, my garter belt and my lipstick that's five months as Charlotte. oh but I don't want you wearing my clothes so I will have to take you underwear shopping and dress shopping, I'm sure all of us and many of your school friends will help you with this. after the five months you are free to return to manhood, but if I ever catch you being a sissy after that time you will stay as Charlotte forever, now be a good girl and go and make us some drinks!" the end
silkysissy silkysissy 16-17 27 Responses Feb 6, 2012

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such a nice story

Your moms a *****

oh crap, i've super glued my false nails on.

wow, just wow.

Well, looks like mama, granma, aunti and your ex-girlfriend know best. And wirtha ll the neighbors knowing as well and spending 5 months as a girl, there is no turnoing back. Of course Princess your morgher said that you can rreturn to being a man after that, but she knows you would never want to be again. You are now a girl for life Whan yould be really nice of your ex-girlfriend is if she could find some noice boys foir you so you could double date with her Your mother playing *** your little thing iwas simply a first step in making you realize no woman would ever actually be interested in that. No little girl, you nreed to develop your oral talents and also your *****. Once you have excperienced those girlie ******* you will realize hom much better those are than tyhose terrible male type. And now that it is allout in the open don't ypou realize you should have let your mum know about this years ago? Silly girl. Be sure to thank your mum and ask her to help you be all the girl you can bge. Promise here you will not remove your clothes unless she pleases or of course some lovely man you want to please removes them.

It depends on how old he is. If he's an adult then its just mom getting even and there is nothing wrong with teaching him a lesson. it maybe he be Charlotte forever.

I take it you took your mom up on the offer to go shopping and become her special daughter.


you do realize that super glue is bad for your skin, right? it can cause chemical burns and I really don't think you want that **** on your feet....

who mentioned anything about super glue?

"she took me to her wardrobe and pulled out some red 4 and a half inch heels and slid them onto me." why do they feel wet" I asked. "oh that's just the superglue setting and don't you dare try and take them off". "

I wish my mom would have done that

I think many of us would have liked that to happen to us. I know I would.

great story


Oh that sounded like fun, the mother sounds like a true mistress. Would she like a another to turn into a true sissy?

Glad to see more sissy boys getting what they need to get.

Not sure why you don't want anyone to see your profile. But, please add me. Would love to chat with you about our desires.

hello lets chat

I'd do the time then leave them behind. The mother if she had been so concerned about him wearing girls clothes she would have stopped it before right? How long had he been doing it and she gave him a five month punishment? And that punishment is for him to do what she wants him to stop doing? The threat of being outed was preventing him from doing it more. Once the moms punishment breaches the barrier/threat it no longer stands as an impediment. She is either stupid or lying.

Why leave them behind? Simple... overkill. A demonstrative lack of respect that can only get worse. Again the punishment gives carte blanche to everyone to disrespect the guy. The mom may have put a timer on his punishment but she has no off switch to turn off the abuse of others. This petticoat punishment is the most irresponsible type of sensationalistic bravado and has no benefit to the subject. It can destroy a person mentally and emotionally as well as their reputation. THAT IS WHAT MAKES IT A PUNISHMENT the damage it can/will do.

It's only a Transgender story. People (neighbors) wouldn't really react that way. They'd probably call the police.

did you have to spend the time after 5 months as a girlie too?

I really hope that was a fictional story. If it wasn't your mum is pretty twisted. I enjoyed reading it though. Please add me so I can see more!

omg do it all too me!! I wish tht was me sooo bad

i wouldn't like this at all your mum sounds soo brutal. and as im typing this i my hands are like super shakkey soo sry for the speelinnggg erorrs

I just tuck my sissy **** between my legs, pull my panties up and let the juices fill my panties I'll wear them the rest of the day.

I just tuck my sissy **** between my legs, pull my panties up and let the juices fill my panties I'll wear them the rest of the day.

Could I be your friend?

Please add me. I want to hear more of your stories and about your adventures.

she would have you tied up, wearing a dress and begging for mercy in ten seconds! you must have been a very naughty boy!

Sounds so wonderful

I would love to be married to your mom. I wonder how i would wind up.

Such a wonderful story. Wish that could have been me.

I wanna be next!