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.
“Never 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!"