Mothers Sissyboy by Sissy Ellen

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From our 1999 archives:

Mothers Sissyboy by Sissy Ellen

Part 1

story:   My Father died when I was just 12 years old leaving my mother to raise me(12 years old) and my youngers sister Becky who was 10 years old. After he was gone for a year we got on with our lives and life almost seemed normal. My mother was allways getting on my case for being over weight. After my dad died, I turned to eating for comfort. My little sister was always calling me fatty which really pissed me off. I could not catch her though, she was very athletic and fast. I would get out of breath and start to huff and puff when I tried to get her. My mother got more and more disgusted with my wieght problem as time went on and even urged my little sister to tease me, thinking it might help to motivate me to lose some weight.

Meanwhile I just sat in the house watching TV and eating as Becky played outside getting stronger by the day. Then one night my mother came into my room to talk to me. I had just got out of the shower and had a towel around my waist. My mother just stared at me with her mouth open, as she saw me standing there with just the towel covering my privates." My God" she said. Look how big and flabby your breast are. Your so fat that your boobs are as big as mine she said as she laughed at me. I am going to put you on a diet tomorrow morning she told me as she walked out of my room.

The next day after school, I was at home with my sister and her 10 year old girl friend. My mother would not be home for work for a few hours. I was sitting on the couch stuffing my face with a bag of chips when my little sister and her friend walked into the room. My sister walked over to me and quickly snatched the bag of potato chips out of my hands. Dont you think you have had enough to eat Fatboy, she asked me.

I was so mad I stood up and tried to hit her, but she was to fast. She moved out of the way of my weak punch and then she very quickly hit me in my stomach with her fist. Her punch knocked the breath out of me, and I fell to the floor gasping for air. What a fat whimp my sister said as she grabbed me by my hair and smacked me in the face so hard it brought tears to my eyes and I could not see. All I could do was to sit on the floor crying as she kept hitting me in the back of my head with her hand. What a fat sissy tub of lard my sister said as she grabbed me by my shirt collar and tried to lift me off of the floor. I was to heavy and my shirt ripped off of me. She had my ripped shirt in her hand as she and her little friend looked at me and started to laugh. My sisters friend told becky that I had bigger boobs then her mother and her 16 year old sister.

Then Becky grabbed me by my ear and twisted it. Follow me fat sissy, she said as she dragged me by my ear up to our mothers bedroom. Then my sister told her friend to open the second drawer of my mothers dresser. Then Becky told her friend to hold my ear, while she looked for a bra for me to try on. If he moves a muscle, twist his fat sissy ear off she instructed her friend. I was crying and to afraid to move at all, so I just stood there while my little sister looked for a bra for me. This is perfect said Becky, and she turned around and faced me and held a pink bra up to my chest.

I think this should fit our fat sissy just fine she said as she guided my arms through the bra straps. After she had fastened the bra on me from behind. She then adjusted the bra cups a little and fiddles with the bra straps until she was satisfied that the bra fit me just right. I was so ashamed as I looked into the mirror and saw that the bra fit me just fine." Now thats what our fat sissy has needed for a long time", said my mother as she walked into her bedroom.

Part 2

There I stood in my mothers bedroom wearing a pink bra that my little sister and her little
girlfriend forcefully put on me. My sister friend held my ear tightly in her fingers as Becky
adjusted the bra straps. Then I heard a voice come from behind me. "You seem to fill out
my bra better then I do,said my mother as she walked into the room. She walked up
behind me and put her arms around me and cupped my bra covered breast in her hands. As
she held my boobs in her Hands , she gently massaged my nipples with her fingers through
my bra. It seems that my chubby sissy son needs a C cup bra. The bra you have on is a B
cup bra and it is to small for my chubby big boob sissy, she said as she took my other ear
in her fingers. My mother told Becky's friend that she could let go of my ear, I have the
sissy now she told her.

My mother led me over to her make up mirror and sat me down on
the seat in front of the mirror. She stood behind me adjusting my bra straps as she told me
how cute I looked in my first bra. This is a special day for my fat sissy son, she told
everyone as she fondled my breast through my bra. My sissy son has needed a bra for a
few years now. But my sissy skipped her training bra and went right into a womans bra.
Then my mother started to brush my shoulder length hair and pulled it into a pony tail and
and told my little sister to go to her room and bring her a pink ribbon so she could tie my
pony tail. When my little sister got back, she handed my mother the pink ribbon and then
she tied my hair into a pony tail. Next my mother sprayed some of her perfume all over my
neck and rubbed it into my skin. Now my big boobed sissy smells as sweet as she looks,
said my mother. Then my mother told Becky to go to her dresser and get her the satin
pink blouse out of her top drawer. When becky came back with the pink blouse, my
mother told me to hold out my arms, and she slipped the pink blouse on me and buttoned
up the back. Then she led me over to the mirror so I could have a look at myself. I was
horrified. My boobs pushed the front of the blouse way out. Plus you could plainly see the
out line of my bra through the thin material of the blouse. Then she tucked the blouse into
my jeans and told Becky that we were all going to the mall to buy your sissy brother some
bigger bras that fit him properly, my bras are just to small for him. We will get our big
boobed sissy's ears pierced while we are at the mall she told becky and me. I looked at my
mother and told her that i could not go to the mall like this. She said you are right honey,
then she took me back over to her make up vanity and sat me back down on the chair.
Then she made me pucker my lips for her as she put some pink lip stick on me. Then she
put just a little blush on my cheeks and also put some eye liner on me and mascara. She
then warned me that if I opened my mouth again, she would make me wear a dress to the
mall.

Part 3

After my mother had buttoned up the the pink blouse that she put on me, she took my hand and walked me over to the mirror. Then she tucked my pink blouse into my jeans. I looked at the mirror and almost died. I saw that my boobs pushed out the front of my pink blouse way out. I also noticed that I could plainly see the outline of my bra through the material of the blouse I was wearing. The blouse was to tight on me and made my tits loook hudge. Plus my boobs bounced up and down in the bra when I walked.

Then my mother kissed my cheek and told me that my perfume made me smell as sweet as I looked. Becky and her friend Linda and my mother all busted out laughing at me. I was now mad at myself for having shoulder length hair. My mother had tied in tightly into a pony tail and tied it in place with a pink ribbon that she tied into a big pink bow.

Then my mother said "come on girls, lets go to the mall and shop till we drop". Then becky grabbed my hand and my mother grabbed my other hand and they dragged me to the car.

On the way to the mall becky told me how well my pink blouse matched my pink lipstick and the pink bow in my hair, and all of them busted out laughing again. After we pulled into the Mall's parking lot everyone got out of the car but me. My mother asked me to get out of the car and I refused. Then my mom asked Becky to help me out of the car. She said if you can make the sissy wear a bra, getting her out of the car should be easy. becky got back in the car and told me to get out. I just sat there and she told me if I knew what was good for me that I should get out of the car. Then she told me that when we got home she was going to whip me with a belt, as she grabbed my ear and dragged me out of the car.

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Mothers Sissyboy by Sissy Ellen

Part 4

 After Becky grabbed me by my ear and yanked me out of the car, she told mother, that she was going to whip me with the belt when we got home. Then mother told Becky and Linda that they could not have a sissyboy that wore a bra disobeying his little sister. Then mother had Becky and her little girl friend Linda each grab one of my hands and walk me inside of the mall. As soon as we got to the JC Pennies store inside of the mall, my mother took us to the womans Lingerie department. My mother led us to the bra section, and found a woman sales lady who could help us. The sales lady was my mothers age and took us to a dressing room. Then my mother told the dales lady that I was wearing one of her bras, but it was a bit to small for me, and I needed to be measured to determine my proper bra size.

The sales lady started to unbutton my blouse, as my mother and Becky and her friend started to giggle. After the sales lady had unbuttoned my bouse , she took it off of me so I was standing in the dressing room in just my bra and my jeans. The sales lady just stared at my bra, and commented on how it was with out a doubt to smalll for me. The sales lady told my mother that i was very well developed for a young girl. As the sales lady felt my breast through my bra, she said that I had quite a set of boobs for such a young girl. Then she reached around and unhooked my bra and took it off of me. She almost fainted when she saw my small nipples and knew right away that I was a boy and not a girl. She looked at my mother and asked her what a boy like me was doing with breast larger then her and my mother. My mother then told the lady that since I had boobs like a woman, I was going to start to wear a bra like a woman. The sales lady said that with boobs as large as mine that I really did need to wear a bra and that she would help me. She then took her measuring tape and measured me around my boobs. She told my mother that i was a full C cup. She told my mother that for a proper fit that I needed a 36 "C" cup bra. Then my mothe rotld me to stay in the dressing room with my sister and her friend, while she and the sales lady went out and picked out a few bras for me to try on.

Part 5

As I stood in the womans dressing room wearing only my blue jeans, my sister Becky and her little friend Linda started to tease me. Becky held me tightly by my ear as her little friend started to feel my boobs. As Linda held my boobs in her hands Becky told her that it looked like the sissy was enjoying the attention Linda was giving me. Just think sissyboy, mother and the nice sales lady are picking out a nice new pretty bra for you right now as we speak, said Becky as Linda fondled my breast. Just then my mother and the sales lady came back into the dressing room holding a bunch of bras. Mother told me that she had picked out 7 bras for me to try on, one for each day of the week. Mother handed me a white playtex cross your heart bra and told me to put it on for her. We want to see if it fits you properly she told me as they all started to laugh at me. The sales lady told me to slip my arms into the bra straps and pull the two ends of the bra behind me and fasten them behind my back. I was standing there fumbling with the bra trying to hook it when Beckies little friend Linda, hooked my bra for me. My mother adjusted the bra straps for a moment until she decided that it was right and smiled as she looked at me in my new bra. It fits you like a glove said my mother as she turned me around so I was facing the mirror on the dressing room wall. I saw how my breast filled out the bra cups. I also noticed how this bra was not to tight on me like my mothers bra was. Then the sales lady commented how this bra did not push my boobs up aganist my chest like my mothers bra did, it supports them like a bra is supposed to. See how the little sissys boobs fill out the bra and puch out in front, said the sales lady as she stood behind me with her arms around me cupping my breast with her hands.

My mother reached behind me and unhooked my bra and took it off of me and handed me another bra to try on for them. I whispered into my mothers ear and told her that I needed to go to the bathroom. You should have gone before we left the house she told me. You will have to wait until we are through trying on your new bras she told me. I had to pee really bad and started to kind of dance around from one foot to the other one. The sales lady told me to hold out my arms as she slipped a pink bra on me and fastened it in the back. She adjusted the bra straps a bit and turned me around so my mother and Becky and her friend could see how well my bra fit me. Then I felt the urge to per again really bad.

Part 6

As I stood in the womans dressing room wearing the pink bra that the sales lady had just put on me, I felt the urge to pee growing stronger. I whispered in my mothers ear, and told her that I had to pee quite badly. She told me that I should have used the bathroom before we left home. She told me that I only had four more bras to try on and then we would go home and I could use the toilet then. I had to pee so badly that I started to move around from one leg to the other. Becky and her friend Linds saw this, and Becky commented on how cute my pee pee dance was. My mother decided that the pink bra I was wearing was a bit to small for me, and she took it off of me. Then she and the sales lady went back out to find another bra for me to try on.

Becky grabbed my ear again and told me to stand still. She twisted my ear until it hurt so bad, that I stood still for her. Linda threw a bra that I had allready tried on to me and told me to put it on. She slipped the bra straps over my arms and fastened it in the back. Becky held my ear tightly as her friend linda started to massage the front of my bra. I had to pee so badly and here I was being held hostage by my little sister and her friend. My mother and the sales lady came back into the dressing room and held out a bra for me to try on. I was told to take of the bra I was wearing and to try on the one that they just got for me. I lost the battle with my bladder and started to wet myself as I stood there. Becky saw that I had wet my pants and started to tell everyone how her sissy brother had just wet his pants like a baby.

The sales lady looked at my wet pants and told my mother that I needed a few more things then just a bra. It seems that our sissy needs to work on his toilet training a little bit, said my mother as everyone started to laugh at my perdicament. Then she told my sister Becky and her friend to run over to the baby department and get some diapers and plastic pants for me to try on. I started to cry as I stood in the dressing room in just my jeans and a bra. It's OK baby, my mother told me. I will get my sweet sissybaby into some dry brtiches just as soon as your little big sister, gets back with your diapers. When my sister and her friend got back, they had a whole shopping cart full of stuff.

My mother made me lay on the floor, as she folded a few diapers together. She then pinned the thick bulky diapers on me and slipped the plastic pants on me over the diapers. It is a good thing that this store has a good incontinence section said my mother as she stuck a paciafier into my mouth. Just then the sales lady told my mother that she should make me wear just my diapers and plastic pants home. My mother started laughing and said thats a great idea. The sales lady handed my mother a pink sports bra and said the sissy should wear this as well. Then after my mother had put the sports bra on me, she told Becky and her friend to each take one of my hands and help me out to the cashier, so we could pay for all of my new things.

Part 7

There I stood in the dressing room with my mother and sister and the sales lady and Beckies friend Linda wearing nothing but the pink sports bra and the thick diapers and plastic pants with a pink paciafier stuck in my mouth. Becky and her friend each held one of my hands and started to walk to the door of the dressing room. I started to cry very hard and tried to plead with my mother not to take me out into the store with me dressed like this, but with the paciafier in my mouth my words were all muffled and garbeled. Pweeese modder, pweeese done make me wear dis bwa and baby diapers and wubber pants to de store, I pleaded through my paciafier. Linda laughed and told every one that the cute sissybaby sounded as cute as he looked and all of them burst out laughing.

My mother told Becky and linda to go out to the little girls department and find me something appropriate to wear home over my bra and diapers. When Becky and Linda came back they were holding this really small sissy looking pink party dress. My mother took the pink dress from Becky and held it up to me and said it was darling, and it would be fine for me to wear home. I cried through my paciafier and said, " pweeese ma ma, done make me wear a wittle girl thisssy dwess, I am a boy. My mother started to laugh and asked me if I was a boy then how come I had the largest and plumpest boobs in the room. I mean the sales lady and i are grown woman and you have much bigger boobs then either one of us. The bra you are wearing right now is at least one full cup size bigger then anyone else in this dresing room.

So you definantly need a bra, and you will wear one at all times like any other self respecting lady should. Now hush up any more back talk from my sissy and I will make you wear just your bra and diapers and rubber pants home, she told me as she slipped the pink dress over my head. All I could do was to cry as she fussed with the dress until she had it on me just the way she wanted it. Dosent my sweet sissy look pretty in her new pink dress my mother said as she turned me towards the mirror so I could see myself. I looked in the miror and was horrified, My breast pushed out the front of my dress very much.

You could see my bra through the thin material of the dress, and the dress was so short that it bearly came down to cover my diapers and plastic pants. My mother tied the big pink bow in the back of my dress. I just stood there crying as my mother handed me all of the bras that she wanted to buy for me. You carry your new bras, she told me. that way everyone will at least know that even though you have to wear diapers, you need a bra like a good sissy. Then my mother pushed me out of the dressing room and Becky and her friend Linda each took one of my hands and walked me to the check out line.