Tim's Sissy Day Part by Susan Roseybottom

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Tim's Sissy Day Part by Susan Roseybottom (2000)

part 1

Tim was a normal 10 year old boy. He liked to fish and and play ball with his friends. He also liked to tease the girls,especially Patty. Patty was a bit on the heavy side and liked wearing especially frilly party dresses. Tim just couldn’t resist making fun of Patty even though his mother often warned him to stop doing it. He often laughed at her and called her Fatty Patty. One day Tim saw Patty walking down the street in one of her frilly dresses. He also saw a mudpuddle just ahead of where she was walking. Timing it just right, Tim rode his bike through the puddle just as Patty was walking past it. He splashed mud all over her dress. He laughed and said “How’s the water Fatty Patty.” When he got home his mother was furious. “Patty’s mother called and said you ruined her dress” said mother. “I’ve warned you about picking on her many times and I’ve had it with you. You will be punished this time,no go to bed right now. You can forget about supper."
        The next morning Tim’s mother called him into her bedroom. “As you know,Patty and her mother are having a mother&daughter tea party this afternoon,she said. “As punishment for what you did yesterday,you and I will be attending that party”
        “But mom,that’s just for girls!”cryed Tim.
         â€śNever the less,we’re going,replyed his mother. “Now let’s get you properly attired for the party”.
        “You mean I not only have to go to an all girl party,but I have to wear my suit? groaned Tim.
        “Heavens no,repled his mother. “I said properly attired. You will be wearing a dress. Patty has been kind enough to lend you one of her prettiest pink dresses for the party.”

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part 2

        "Oh,No!" exclaimed Tim. "You can't make me wear a dress! Besides Patty is much bigger than me and her clothes wouldn't fit me!"
        "Well dear",replyed mother "This is a dress Patty outgrew years ago so it should fit you just fine." Mother went to the closet and got the dress and held it up for Tim to see. It was a very short pale pink dress with puffed sleaves. The hem,sleaves,and neckline were trimmed with delicate white lace. There were little pink satin ribbons addorning the sleaves and a pink satin sash went around the bodice to be tied in the back. "Isn't this just darling" said mother "You are going to look so sweet in this dress. Now lets get you out of those PJ's.
        Tim backed away in horror. "But..but that's a baby dress."he stammered. "You can't make me wear it. I won't wear!!! and he turned to run from the room.
        Mother caught him in a flash. "You most certainly will wear it." she cryed as she pulled the struggling boy over her lap. Mother pulled down Tim's pj bottom and delivered the first stinging swat to his bare bottom. "You will wear the dress and everything else Patty and I have picked out for you!" SLAP SLAP SLAP "You will be a good little girl for the rest of the day!" SLAP SLAP SLAP "You will do everything Patty and I tell you to do!" SLAP SLAP SLAP "Is that Clear?" SLAP SLAP SLAP.
        By this time Tim's poor little bottom was beet red and he was crying hysterically.
        "Please stop!" he cryed. "I'll be good"
        "Do you promise to be a good little girl and do everything Patty and I tell you?" asked mother.
        "Yes" he replyed.
        "Say it" said mother
        "I promise to be a good little girl and do everything Patty and you tell me. Please don't spank me anymore." said Tim.
        "That's better!" replyed mother. "Now off with those pj's and get on the bed. Patty and I decided your actions were so childish that you won't be allowed to be a big girl at the party. You will have to wear a diaper under your dress."

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part 3

"Oh No!" cryed Tim,"Please Mom,anything but that"
        "You deserve this and much more after what you did to Patty." replyed mother as she removed Tim's pj's. Tim started to cry as mother laid the naked boy down on the bed. "It's a good thing I recently gave birth to your sister" said mother. "We have plenty of everything we need." She rolled Tim over and sprinkled baby powder on his little pink bottom. Then she turned him back over,lifted his legs and slid a thick cotton diaper under him. Next mother took some baby lotion and began to rub it on his little wee-wee. "Just to give you something special to think about" said mother. "At some point during the party Patty is going to lay you down on the floor and,in front of everybody,she's going to change your diaper. Patty will be powdering your little bottom and rubbing baby lotion on your wee-wee." Tim's tears flowed as he thought about this new humiliation. Mother then pulled the diaper up between Tim's legs and pinned the sides together with large pink diaper pins. "Now lets get you into your plastic panties so you won't leak when you wet yourself" said mother. With that mother held up a pair of pink plastic panties with rows and rows of ruffles on them. "Aren't these just adorable?" she said as she slipped them over Tim's feet and pulled them up over his thick cotton diapers.
        "Now stand up and walk over to the chair and sit down" commanded mother. Tim's cheeks turned beet red when he discovered that his diapers were so thick that he had to waddle like a baby. After sitting Tim's mother produced a pair of white socks with pink ruffles at the top. "These are so sweet." she said as she put them on his feet. She turned down the tops and then got a pair of shiny black patent Mary Jane shoes and strapped them on his feet. "Now stand up." she said as she went to the closet.
        "What's that!" cryed Tim in horror,as he looked at what she brought from the closet.
        "Why these are your petticoats." she replyed. "They'll make the skirt of you dress stand out so prettily and will make a darling rustling sound as you walk. The petticoats mother held up had layer upon layer of pretty white ruffles trimmed with pink ribbons that were attached to a sheer lace top. "Hold up your arms dear." she said as she lowered the garment over his head. "There,now you're ready for your lovely dress"
        Mother had Tim raise his arms again and she pulled Patty's baby dress over his head. She spun him around and buttoned up the back and tied the sash into a big pink bow behind his back. Then she adjusted the skirt over the petticoats. "Oh,my" she said,Don't you look pretty! It's a shame your hair isn't long enough to put some pretty ribbons in it. I guess this will have to do." With that mother produced a frilly pink baby bonnet. It was pink satin in the same shade as his dress and had little pink and white flowers embroidered on the front. Mother placed it on Tim's head and tied the pink ribbons under his chin in a pretty bow. "Just on more little thing" she said as she held up a little pink pacifier. She placed it in his mouth and said,"Now you stand there like a good little girl and suc-k on your pacifier while I get ready.
        Mother dressed for the party and then packed Tim's diaper bag. She took Tim by the hand and lead him downstairs. She took him out on the porch and placed him in a baby stroller and pushed him out onto the sidewalk. Instead of turning right to head towards Patty's house,mother turned left. Tim's tears started flowing again as mother explained. "Before we go to the party,Patty thought it would be nice to take you over to the ballfield and show all your friends what a sweet pretty little baby girl you are!"

part 4

Poor Tim was absolutely distraught over the thought that all his friends were going to see him in his little pink dress. He hoped his best friend Alan wouldn't be there. He suc-ked nervously on his pacifier.
        Mother pushed the stroller to the ballfield. Tim could see all his friends gathered together,getting ready to start a game. They turned as mother called to them and asked them to come over. Mother lifted Tim out of the stoller and stood him next to her as the boys approached. "Do you boys recognize this pretty little baby girl?" she asked as they arrived.
        Tim could see that his best friend Alan was with them. The boys stared at Tim and then one suddenly realized who it was and shouted "Oh look guys,it's Tim. Why's he dressed like that?"
        "Well,replyed mother,"He's going to Patty's tea party so he's wearing his prettiest dress. Doesn't he look sweet? Darling,lift up your skirt and petticoats so the boy's can see what you're wearing underneath."
        Tim's cheeks turned bright red as he lifted his skirts. The boys started laughing. "Look he's wearing a diaper! What a sissy! " One boy cryed "Does the little girl go wee wee in her diaper?" Tim started to cry which made the boys laugh even harder. "What's the matter little girl?" said one boy. "Is the baby girl hungry? Does she need her baby bottle?"
        "You might be right." said mother. "I haven't fed my little girl in a while. Have you boys ever seen a mother feed her baby?"
        "Oh no!" thought Tim, "She's going to make me suc-k on a baby bottle in front of all the guys." However Tim had watched her pack the diaper bag and didn't see her add any bottles.
        "Alan" said mother, "Would you please get the blanket out of the diaper bag a spread it on the ground. Alan did as mother asked. Mother sat down on the blanket and pulled Tim into her lap,laying him down on his back. The boys gathered around to watch. "Now this is a very natuaral and wonderfull thing." said mother.
        Tim's eyes opened wide in horror. "Oh NO NO NO NO",he thought as she began to unbutton her blouse.

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Tim started to struggle but mother held him firmly. Her blouse was unbuttoned to show her white nursing bra. She reached up and unfastened the tab and exposed her swollen nipple. Cupping Tim's head in her hand she pressed his lips to her nipple. "Now be a good sweet little girl and take mommies nipple into your mouth and suc-k on it." she said. She also whispered in a tone too low for the other boys to hear,"If you don't you will really get punished."
        Poor Tim had no choice. Closing his eyes so he wouldn't have to see the looks on his friends faces,he took mommies nipple into his mouth and began to suc-k. Mother's warm sweet milk flowed from her breast into Tim's mouth. "There now." cooed mother. "Isn't that nice? Doesn't mommies sweet little baby girl look so peacefull nursing at my breast?"
        As mother's warm milk flowed into his mouth Tim started to get a little sleepy and his mind began to drift. He suddenly snapped back as he realized that he had just begun to wet his diaper. He tryed to stop but couldn't and was soon completely soaked. He couldn't believe he had wet himself. He stopped nursing and began to cry. "Oh dear" said mother "I think my little baby has wet herslf. Have you made a pee-pee in your didi?' she asked the poor crying boy. Tim only cryed harder. "As you can see boys",explained mother,"Little babys get very upset when they have wet diapers." Tim's friends were practically in tears themselves from laughing so hard. "Now calm down dear",mother said to Tim as she put his little pink pacifier in his mouth. "Mother's going to change that awfull wet diaper and her sweet little girl will feel much better."
        "Alan,would you please get me a fresh diaper,powder,and baby lotion from the diaper bag?" mother asked. Alan handed them to her. Mother laid Tim down on his back and asked two of the boys to hold up Tim's skirt and petticoats. Then she pulled his pink plastic panties down around his ankles and unpinned his diaper. "My,my" she said,"You really are soaked." As the boys watched and laughed,mother removed Tim's soggy diaper and cleaned him up with a Baby Wipe. Then she powdered his bottom and rubbed lotion on his wee-wee. Finally she slipped a fresh diaper under his bottom,brought it up between his legs,and pinned the sides together. Then she pulled his plastic pants back up. Mother stood Tim up and adjusted his pretty pink skirts over his white fluffy petticoats. "There",she said,"All fresh,dry,and pretty again."
        "Well boys" said mother, "I hope you've all learned something usefull today. Maybe someday I'll need one of you to babysit and now you know how to change a diaper. Now we really must be going to Patty's party."
        Mother picked Tim up and placed him in the stroller. "Wave bye-bye to the boys honey." said mother. Tim waved and the boys,still laughing,waved back. "Bye-bye little girl." they said, "Have fun at Patty's party!" Mother started pushing the stroller in the direction of Patty's house.

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part 6

        Finally they arrived at Patty's house. Both Patty and her mother met them at the door. "Oh!" exclaimed Patty's mother, "Doesn't Tim look adorable."
        "Does the sweet little baby girl like her pretty pink dress?" giggled Patty.
        Tim's mother lifted him out of the stroller and set him down. Patty took him by the hand and led him inside to show the other girls. They all laughed when they saw him. They made him twirl around in his dress and lift up his skirts so they could see his diapers. "I'll bet the baby girl is hungry." said Patty. "We should feed her. I have several baby bottles all ready filled with ice tea and I made some special pudding for the baby.
        "Good idea,said Patty's friend Mary,"But if we're going to give her pudding,she'll need a bib. We don't want her messing up her pretty pink dress."
        Mother overheard what the girls were saying. "Mary",she said, "I brought Tim's bib with me. It's in his diaper bag."
        Mary went a got the bib out of the diaper bag and held it up for all to see. It was white with pink ties and edge trim. Tim looked at it with horror as ,in bright pink thread, the words SISSY TIMMY were embroidered on it. "Isn't this just darling" exclaimed Mary as she approached Tim. Tim started to run away but was grabbed and held by two of the girls as Mary tied his bib around his neck. He was then forced to sit in Patty's lap as she fed him his first baby bottle of iced tea. The women smiled and the girls giggled as Tim suc-ked on his bottle until it was empty. Then Patty lifted him up to her shoulder and started to gently pat him on the back. In spite of himself he let out a little burp. Everybody laughed at that. One of the girls brought a bowl of pudding and a spoon and Patty began feeding it to him. It had kind of a funny taste but they made him eat every bit of it. Mary then took a turn giving him his second bottle of ice tea. Tim began to squirm as he realized he would soon have to pee in his diaper. "Well,I'll just have to hold it",he thought. But the girls had other ideas as they took turns feeding him bottle after bottle of tea. Suddenly he grimaced as he felt a cramp. "I think the secret indrediant we put in the pudding is starting to work."giggled Patty.
        "What did they mean?" wondered Tim. Then he was seized by another more powerfull cramp. He then knew that the girls had put ex-lax in his pudding. He started crying as yet another cramp happened and he couldn't hold back. Tim began to poo in his diaper and then his bladder let go as well. Poor Tim wailed as he peed and pooped in his diaper. "Oh dear" cryed Patty "I think the little sissy girl just messed her diaper!"

[archives]

part 7

“Whew” cryed Mary as she held her nose.
        Patty held the crying boy in her arms and tryed to comfort him. “It’s all right sweetie.” she said. “Little baby girls often do poopy in their diapers. The girls and I will take care of it.” Patty then popped Tim’s little pink pacifier into his mouth. A couple of the girls spread a pink plastic sheet on the floor and then they laid the still weeping boy down on his back. Mary held Tim’s skirt and petticoat up while Patty pulled down his pink plastic pants. “My My! she said as she unpinned his diaper, “This little girl sure is stinky!”
        Mary giggled and pointed “Look at his tiny little wee wee. My four year old brother has a bigger one! No wonder Timmy’s such a sissy!”
        Tim began to weep with embarassment as the girls all laughed at the size of his pen-is. “Oh,poor baby” Patty said, “Are the mean old girls making fun of the little sissy’s wee wee?” Patty reached down and started to tickle Tim’s wee wee. This caused the poor humiliated boy to pee again. It shot straight up into the air and splashed down all over the front of his dress.
        “Goodness!” said mother ,”What a mess! I don’t think baby wipes are going to take care of this. I think you girls better give Tim a bath”.
        Mother whispered something to two of the girls and they hurried off to prepare Tim’s bath. Patty and Mary cleaned him up as best they could with baby wipes and then they began to undress him. Soon Tim stood in the middle of the room surrounded by women and young girls. He was completely naked except for the little pink pacifier in his mouth. He couldn’t even cover his little wee wee as Patty and Mary were holding his hands.
        “Time for your bath little girl” said Patty and she and Mary began to lead the boy toward the bathroom.
        “Be sure to clean her both inside and out”,said Mother.
        “Oh,We will”,giggled Mary.
        Tim wondered what they meant by that as the girls led him away. Mary and Patty held his hands tighter as they entered the bathroom. Tim looked up and his eyes bulged in terror at what he saw. He struggled to break free but the girls held him tight. Hanging from a hook on the wall was a thick rubber bag with a tube running down from it to the wand that one grinning girl held in her hand. There was a clamp on tube.
        “Bring the little sissy over here.” she said, “And bend her over!”

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part 8

Tim struggled but Mary and Patty held him firmly and dragged him across the floor. They bent him over and Patty took the wand and pushed it all the into Tim's behind. She opened the clamp and Tim moaned as the warm water flowed from the bag into his bottom. He felt the pressure build and build. Finally the bag was empty and Patty said,"I'm going to remove the wand now but you had better hold it all in or you will regret it. Do you understand?" Tim groaned but nodded his head. Patty slipped the wand out of his bottom.
        "Now,I want you to thank your Auntie Patty for taking such good care of you." said Patty. and I want you to promise that from now on you will be a good and sweet baby girl."
        Tim moaned from the discomfort of holding in all that warm water. "Thank you Auntie Patty,he whispered,"for taking such good care of me. I promise to be a good and sweet baby girl."
        "Louder! shouted Patty,"Or you'll hold that water all afternoon."
        Tim repeated himself.
        "What do you think girls? asked Patty, "Shall we let the little sissy girl go potty?
        "I guess we better," replyed Mary,"Or she'll probably make a huge mess.
        The girls lifted Tim up and held him over the potty. "You can let it out now sweetie." said Patty. Tim let go and the water gushed out of him along with any remaining poo poo.
        "There,"said Mary,"The little girl is all clean on the inside. Now to do the outside."
        They picked Tim up and lowered him into the tub. It was filled with warm soapy water. The girls gathered around and began to wash him with their hands. Patty paid special attention to his little wee wee and they all giggled as it got very stiff and stuck straight out. After they had washed every inch of the boy they lifted him out of the tub and dryed him off. Then Patty took him by the hand and led the still naked boy back to the living room.
        "Our little baby girl is all fresh and clean inside and out." said Patty as she laid him down on a fresh sheet that had been spread out on the floor. Patty and Mary rubbed baby lotion on his bottom and his wee wee. Then Patty lifted him up by his ankles and slipped a fresh diaper under him. She drew it up between his legs and pinned the side together. Mary reached into the diaper bag and pulled out a fresh pair of pink plastic panties. She put his feet through the leg holes and drew them up over his diaper.
        "What can we dress her in?" asked Mary. "She peed all over her pretty pink dress and petticoats."
        "I think there are some of your old footed sleepers in a box in the closet." said Patty's mother."I'm so glad I saved them." She went to the closet and found the box. "How about this one?" she said as she held up a pink sleeper with little white lambs embroidered all over it.
        "Oh,that's so adorable!" exclaimed Tim's mother. "It's even the same shade of pink as his pretty bonnet."
        The girls dressed Tim in the sleeper. "Can we take the baby girl outside to play on the front lawn?" asked Patty.
        "Yes" replied Mother,"But first put his bonnet on him to protect him from the sun and bring a blanket for him so he doesn't get grass stains on his pretty sleeper."
        The girls put Tim's pink bonnet on him and tied a pretty bow under his chin. They carried him out into the yard and placed him on a blanket and stuffed his pacifier into his mouth. "Look!" pointed Mary "Here come the boys on their way home from the ball field!" She waved and motioned for them to come over.

Oh no”,thought Tim. “I’m going to be humiliated all over again in front of my friends.” But as the boys came closer Tim realized that it wasn’t his friends at all. Then ,to his horror,he realized who it was. It was Patty’s older cousin Tod and his friends. Tod lived on the other side of town so,thankfully,Tim hardly ever saw him. You see,Tod was an awfull bully and was really mean to Tim whenever they met.
Patty called out “Hey,Tod,come on over and see who we have here.”
Tod walked over with his pals and looked down at Tim. At first he just saw a big baby girl in a pink footed sleeper with matching bonnet lying on a blanket suc-king a pink pacifier. Then he realized who it was. “Hey look guys” he said,”That’s that little kid Tim I was telling you about. He’s all dressed up like a baby girl!”
“Yes” said Patty,”He’s also wearing a diaper. He was wearing an adorable little pink dress and petticoats but, while I was changing his poopy diaper .he peed all over his dress. We had to give him a bath and dress him in his pink sleeper.
The boys howled with laughter upon hearing this and were rolling on the ground when Patty told them that Tim’s mother had breast fed him in front of his friends and that his best friend Alan had helped change his diaper.
“Time for baby to have her ba-ba” said Mary. She sat down on the blanket and placed Tim’s head in her lap. She took out his pacifier and put the nipple of the baby bottle of warm milk to his lips. “Now be a good baby”,she cooed,”And take the nipple and make the milk all gone!” Tim had no choice but to suc-k on the nipple and drink the warm milk. There he lay in front of the towns worst bully suc-king on a baby bottle while wearing a pink footed sleeper and pink baby bonnet. It couldn’t get any worse....Or could it?
“His mothers boob,baby bottles,and a pacifier!” said Tod. “It seems the little sissy really likes to suc-k on things. We’ve got something special she can suc-k on. Right guys?!”
“OOOOOH what a good idea”,exclaimed Patty. “Little sissy girl Tim could certainly use the practise. Some day she’ll be a big girl with a demanding boy friend and will thank us for this. We’ll take her to the playhouse out back for privacy.”
“NO PLEA...” Tim started to shout,but Mary shoved the pacifier back in his mouth. They carried the poor frightened boy to the playhouse in the back yard. He was made to kneel down in the middle of the floor.
Tod stood before him and unzipped his pants. He took out his willy and waved it in Tim’s face. It was already hard. “Here little sissy,”he said. “suc-k on this!”
Tim shook his head but Tod grabbed him by his pink bonnet and stuffed his hard willy into Tim’s mouth. Holding him by his bonnet,Tod rocked his hips and slid his willy in and out of Tim’s mouth. Faster and faster and then he stiffened,let out a load moan and shot his load of boy juice into the sissy’s mouth. Tim tryed to swallow but some of Tod’s juice dribbled out of his mouth and down the front of his sleeper.
“Not bad sissy” said Tod as he withdrew his willy. “Some day you’ll make some guy very happy.”
“Thank goodness that’s over” thought Tim,but then he looked up and saw that all four of Tod’s friends were lined up in front of him with their willy’s hanging out. He groaned as the first in line grabbed him by his bonnet. Soon he lay on the floor of the playhouse exhausted,the front of his sleeper soaked with boy juice.
Mother was waiting in the front yard when the girls carried Tim back. She looked at the flushed faces on the boys and the mess on the front of Tim’s pink sleeper. “Well”,she said , “It looks like my little baby girl has been doing some grown up things! The poor dear looks all worn out. I guess it’s time to get her home and put her down for a nap.”
Mother picked Tim up and placed him in his stroller. “First,” she said, “I want you to thank the boys for treating you like a big girl and letting you suc-k their willy’s. Then thank the girls for being good big sisters and bathing you and changing your diaper.
Beet red,Tim thanked the boys for letting him suc-k them. “Anytime,little girl!” they shouted as they walked away. Then he thanked the girls for bathing him and changing his diaper.
“You’re quite welcome,” said Patty and Mary as they bent down and kissed his cheek. “You’ve been a very sweet little baby girl.”
After they arrived home Mother took Tim upstairs and undressed him and gave him a bath. Then she powdered him ,diapered him, and dressed him a sweet little pink baby doll nightie. She then carried him to his room and layed him on his bed. “You lie quietly,” she said. “I’ll be right back.
When Mother returned she was wearing her night dress. She sat down on the bed and cradled Tim in her arms. “Goodness” she said, “My little baby girl has had quite a day. I think a little warm milk will help you sleep.” Mother drew open a slit in her night dress and exposed her swollen nipple. She lifted Tim’s head to her breast and ,this time,he needed no coaxing. He was soon nursing contentedly at Mothers breast. He moaned as Mother rubbed the front of his diaper.
“I think you like being a little baby girl” she murmured,as she slipped her hand inside Tim’s diaper. “You looked so darling in your pretty pink dress,” she cooed has she stroked his stiff little wee wee.
Tim began to feel really good as he nursed at Mother’s soft breast and she gently played with his wee wee. Suddenly he bagan to tingle all over in wonderfull delight. “That’s Mommy’s sweet girl!” exclaimed Mother as Tim filled his diaper with something very special.
THE END