A Halloween to Remember

 

Part 3: Finally the makeover is complete at the beauty parlor. Jeb leaves with mommy pouting like a baby. Debra has make up at home to apply later. Jeb is going to the party as a cute diapered toddler girl.
“You will be the prettiest little girl at the party,” mom said to Jeb on the way home.
“Yes mother but I will be the only little girl at the party,” Jeb said knowing the girls are young adults.
They arrive home around 4 pm after a traffic jam. As soon as they get home mother washes the diapers. They are dried and fluff up nicely and are snow white in color. The plastic panties are ready to wear. The leotard and tights are washed and dried too along with the training bra and 2 pairs of lacy socks. Ballet slippers were also purchased at Sears.
Being premature at birth made Jeb not grow leg or body hair.  He does not even have to shave his face. The only thing making him still look male are the shorts and shirt he is wearing.
“I just love this skirted leotard,” mother said, “white tights are perfect to go with it.”
Everything is washed, dried, and folded then placed on top of Jeb’s dresser in his bedroom. Supper is served at 6 pm which is left over beef stew. Jeb loves beef stew and has a second bowl.
“Soon I will dress you like a toddler girl,” mother said.
“Please don’t make me go to this party as a diapered toddler girl,” Jeb pleaded, “I would rather stay home.”
“No way are you not going to the party,” Debra said, “Sally is expecting you at 8 pm.”
At 7 pm mother makes sure Jeb uses the potty before she puts his first diaper on in many years. Jeb wet the bed up to age 5 but grew out of that. After taking a piss Jeb goes to his room. Mother has an old diaper mat already on his bed. She found a toddler’s pacifier and 2 old Gerber baby bottles in a box.
“Lay on the diaper mat on your bed sweetie,” mother said, “time to put your diapers on.”
Jeb reluctantly obeys knowing this will suck at his age. Debra folds 3 pinked edged diapers in half making a thick pad of diapers. She lifts Jeb’s bottom by grabbing both ankles and slips the diapers in place. Desitin is rubbed on Jeb’s diaper area and baby powder is used.
Mother pulls the front of Jeb’s diapers up between his legs and folds the ends in for just the right fit. The back of the diaper overlaps the front and is just above Jeb’s belly bottom. Mother pins the one side and then the other at the waist. She takes a second set of pink head diaper pins and pins the diaper closed at the thighs.
“You are so small these diapers fit perfectly folded in half,” mother said, “I pinned them on snugly and they are 6 layers thick.”
Mommy gets a pair of the milky white rumba panties with pink frills across the bottom. She slips Jeb’s feet in the small holes and works them up his legs over the thick diaper. They are a perfect fit like expected.
“Mommy will pack a diaper bag for you to take with you,” she said loading what is needed in a diaper bag.
“Diaper bag? What do I need a diaper bag for?” Jeb asked feeling nervous. “I don’t plan of using these diapers.”
“Once the girls at the party see you are diapered they will expect you to use the diapers,” mom assured Jeb.
This really sucks, Jeb is thinking and knows mommy is right. How would he undress himself to pee after being put in a leotard and tights with a diaper on? Jeb dreads the party already as mommy gets his tights. She takes the white tights and puts them on Jeb. The tights fit nicely over the diaper and plastic baby panties. He has the white training bra put on and fastened in the back.
“Step into your pink skirted leotard sweetie,” mommy said holding it out for him.
Jeb never wore a leotard and does as mommy said. She pulls the leotard up over the diaper and up higher. Jeb’s arms are put in the sleeves as the skirted leotard is pulled up over his shoulders for a perfect fit. The skirt flares out due to the thick diapers and plastic panties.
“You are making me into a sissy!” Jeb exclaimed as his lacy white socks and pink ballet slippers are put on.
Part 4: After getting Jeb completely dressed like a diapered toddler girl ballerina mother calls Sally’s mom before leaving for the party. She explains the situation to Rose knowing she will be pleased.
“No problem, bring the cute ballerina over,” Rose said, “I love the idea of your Halloween costume.” “I am sure one of the girls will know how to do a diaper change.”
Rose said the party is planned to last until midnight. Sally is having Jessica spend the night and Rose offers to let Jeb spend the night too. Debra giggles at the thought and agrees not to pick up Jeb tonight. He will not be told but can find out when he gets there. She feels the boy deserves this for acting like a baby and arguing with mommy about the party.
“I will bring Jeb over in about 15 minutes,” Debra said knowing it is 7:45 on Halloween night.
Rose informs the girls Jessica and Sally about everything. They giggle and can’t wait to see Jeb as a diapered toddler girl ballerina. They go to work with Rose’s help and set up a crib in the girl’s bedroom. Jessica and Sally can sleep in the double bed. Jeb will sleep in the crib.
“Mom this is going to be the best party ever,” Sally told Rose with a big smile. “Let’s put out some snacks before Jeb and the other girls arrive.”
“Enjoy your party sweetie,” Rose said helping to put out snack trays with cookies and candy.
The apartment is decorated with orange and black crepe paper hanging from the ceiling. Ghosts and witches are hanging on the walls along with skeletons. Coming over soon are Julie, Betsy, Mary, and Stacy. Counting Jeb there will be 7 girls at the party including Sally and Jessica. Everything is ready for the guests to arrive.
One by one all the guests arrive at 8 pm. They get there in time to be filled in by Jessica and Sally about Jeb’s situation. All the girls giggle with anticipation and can’t wait till little Jeb arrives. They all know Jeb from seeing him around the apartment complex.
Before walking Jeb over to the party mother put red lip gloss on his lips and a bit of blush on his cheeks. His costume is complete, no one would think Jeb is a boy.
Knock, knock, one more person is at the door. It is Jeb who was brought here by mother. They walked over with a packed diaper bag in hand. The rest of the girls are quiet while Sally and Jessica answer the door.
“Come in little girl, I don’t remember inviting you to my party,” Sally said already teasing Jeb.
“Ha, ha, I am Jeb and you know this,” Jeb said feeling embarrassed, “mother put this costume on me.”
Jeb goes in the apartment while mother gives the diaper bag to Sally. The door is closed, soon Jeb is surrounded by the girls at the party.
“Look everyone, Jeb is a sissybaby ballerina,” Sally said.
“Oh what a wonderful costume,” Jessica said, “and you are wearing a diaper.”
“Do you have problems wetting your panties?” Stacy asked while giggling. “Toddler girls need diapers.”
“I did not think 6 year olds are allowed at adult parties,” said Julie also giggling.
All the girls are either 18 or 19 years old. They know Jeb and think he is wimpy for an 18 year old boy. They know he never dates but did not know he was a sissy. Betsy and Mary stare at Jeb and burst out laughing.
“This is going to be a great Halloween party,” Sally said setting the diaper bag on the table.
“Is your diaper wet little girl?” Sally asks, “Do you need me to change your diaper?”
All the girls have babysat small children and have changed diapers. Jeb insists he is not wet and wants to get the heck out of here. He worries that he can’t run off dressed as he is. Jeb is stunned to find out he is spending the night along with Jessica.
He is taken to Sally’s bedroom along with the other girls. Jeb sees the crib he will be sleeping in and the diaper changing table next to it. He heads for the door but is easily blocked from leaving the bedroom. The front door is dead bolted with a key which is hidden away.
“Help! Let me out of this place now,” Jeb exclaimed.
Part 5: Jeb is nervous being the center of attention diapered and dressed the way he is. Rose comes in the bedroom to see what the noise is. She reminds Jeb he is spending the night and to enjoy the party.
“We set the crib up for you honey and the diaper table,” Rose said bringing in the diaper bag.
Sally looks inside to find 9 more of the pinked edge diapers, frilly plastic baby panties, diaper rash cream, and baby powder. Sally also finds 2 baby bottles in the diaper bag and a pink pacifier. She immediately puts the pink pacifier in Jeb’s mouth.
“I love your frilly plastic panties showing thru your tights,” Sally said flipping up the leotard skirt.
“I can’t believe an 18 year old adult boy lets mommy dress him this way,” Jessica said, “especially the diapers you are wearing.”
“I bet Jeb loves his costume and picked it out himself,” Sally said teasing Jeb more. “You need a girl’s name.”
“Let’s call him Missy, that is a cute name for a diapered toddler ballerina,” Julie pointed out.
“Oh what a pretty name for a pretty toddler girl,” Betsy agreed and so does Stacy and Mary.
Sally whispers a few things to her female guests. They giggle and this makes Missy nervous. Both baby bottles are filled with cold water in the kitchen by Sally.
Sally brings them back to the bedroom as Rose leaves the kids to have their fun. Jeb who is now Missy is held in Sally’s arm on the bed. She puts a baby bottle in his mouth and demands he drink it all up.
“Naughty diapered toddler girls get spankings if needed,” Sally said threatening Missy.
Missy starts nursing on the baby bottle not realizing the girls want him to wet his diaper. When the first baby bottle is empty Jessica bottle feeds Missy the second baby bottle of cold water.
“Don’t worry when you pee your diaper I will change you,” Sally said since it is her party.
Sally is dressed as Snow White and Jessica is dressed as Cinderella. Stacy and Mary are both dressed as mean witches. Julie and Betsy are dressed as vampires. The only girl in diapers is Missy of course.
After 2 full baby bottles of water Missy already has to pee and is holding it. They all go to the living room to have snacks. Missy is given 2 chocolate chip cookies and a peppermint patty. All the girls indulge in Halloween candy and cookies.
“I have just what you girls need,” Rose said, “fruit punch in a punch bowl that smokes like it is on fire.”
Rose sets the punch bowl on the coffee table. She put dry ice in the punch bowl to make it give off fog which is very scary. The girl’s dressed as witches start cackling!
“Ha, ha, ha, ha, ha, give me some magic punch,” they both chant. “Give some to the sissybaby!”
Rose has a sippy cup and puts punch in the cup. This way Jeb as Missy won’t spill any. All 6 other girls enjoy punch with their snacks. A scary movie is put on the television about Frankenstein and Wolf Man. Missy can hardly drink the punch already having to pee.
“Let’s tickle Missy and see if she wets her diaper,” Sally said with an evil grin on her face.
“No wait, I don’t want to be tickled,” Missy responded.
Soon she is laid on the carpet and tickled by Sally and Jessica. It is not long before Jeb as Missy pees his diaper. She could not possibly hold it any longer being tickled. Rose decides to leave the girls alone to have fun.
“Does our diapered toddler girl ballerina need a diaper change?” Sally asked knowing he does.
The girls could tell Missy flooded her diaper by the look on her face. Sally easily picks up Missy and carries her to the diaper table and lays her down. All the girls surround the diaper table to watch the embarrassing diaper change. They realize Missy needs to be standing up at first. She is on her feet and the pink skirted leotard is taken off. Missy’s tights are removed next with help.
“Stop this immediately,” Jeb as Missy said helplessly.
“We can’t let you get a diaper rash,” Jessica replied.
Part 6: Missy is picked up and laid on the diaper table again where her cute plastic rumba panties are taken off to reveal a soaked diaper. Sally unpins the diaper and sees it is 3 diapers folded on half.
Jessica knows what to do next, she folds 3 clean diapers in half and layers them together. Sally is wiping Missy clean with baby wipes found in the diaper bag. Mommy Debra set up this embarrassing situation for Jeb.
“Look! His little penis is standing at attention,” Betsy said giggling, “Little Jeb likes his diapers changed.”
Sally is sure to add diaper rash cream to Missy’s bottom and then front diaper area. She rubs Jeb’s erect penis and balls with Desitin. All the girls are giggling with amazement at the site of this. Sally quickly puts the clean diaper under Jeb’s bottom. She pulls up the front between Jeb’s legs and pins it on like a professional.
“Good thing you got that diaper on quickly,” Jessica said, “he may have wet in a different way.”
The plastic rumba panties are put on Jeb as Missy. The excitement is too much as Jeb masturbates in his diaper. He don’t say a word but loved this diaper change! Jeb is embarrassed about being a sissy. He is properly dressed again in tights and the skirted leotard. One girl said she loves the training bra but that he don’t need one yet.
Soon they are back in the living room watching the rest of the Frankenstein movie. The movie is very scary!
All the girls are liking Jeb since he is a good sport about being Missy. He also don’t stand a chance of getting away and don’t want any spankings. The movie ends around 11 pm and the television is turned off.
The girls all have more punch and snacks. During the party Rose has been giving out candy at the door for those who stopped by trick or treating. Jeb as Missy is the center of attention.
“Is your diaper wet again baby girl?” Sally teased. “I am glad you are spending the night.”
“Mother did not tell me about this but I guess I am if she does not come to get me,” Jeb as Missy said.
“Your mother knows you were invited to spend the night and approved of this,” Rose said, “you sleep in the crib.”
“I am not wet and don’t need changing,” Missy said.
The girls decide to tell ghost stories in the living room. Rose dims the lights for this and listens. After the scary movie ghost stories was easy. Several girls had scary stories of some kind to tell. By the time they were done the party is about over being midnight.
“Mom wants the party to end so thanks for coming,” Sally said to her guests. “Don’t be scared walking home.”
Four of the girls leave to walk home, they are a little nervous but know it is safe. Stacy and Mary live in the same building and walk together.
Betsy and Julie live in the same building and walk together in the other direction. They chat as they walk talking about Jeb being Missy. All 4 girls get home safely after the Halloween party.
Back at Sally’s house it is decided that Missy needs to be diaper changed and put in the crib. Sally and Jessica are happy to do this. They take Missy to the bedroom and find a nightgown for her to wear to bed.
“I wore this when I was 6 so it should fit you Missy,” Sally said, “you can sleep in my nightgown.”
Both Jessica and Sally undress Missy starting with her pink skirted leotard. They take off the white tights but leave on the training bra. The lacy white socks will be put back on. Missy is picked up and put on the changing table. She is feeling helpless to stop any of this.
“Don’t worry you can wear your frilly plastic panties overnight,” Sally said smiling.
Jeb is not excited and kind of drowsy since it is after midnight. Jeb has his frilly plastic panties removed to expose a wet diaper. Jeb is liking being Missy but is not sure how this could happen.
“I see you are not enjoying this diaper change as much,” Jessica commented embarrassing Jeb.
“I don’t know how that happened actually,” Jeb said embarrassed about the situation, “I sure enjoyed it but never had anyone diaper change me since I was 5.”

Conclusion: Jeb is naked on the diaper table while Sally cleans his diaper area after taking off a wet diaper. Jessica is nearby fixing the next diaper for Jeb who is now Missy.
“Should I layer 3 diapers together like before?” Jessica asked, “That will leave 3 more clean diapers in the bag.”
“Yes we have a washer and dryer to get clean diapers,” Sally said rubbing in Desitin and using baby powder.
The girls conclude that Missy will wake up wet and be changed in the morning. After that they can wash and dry all the diapers used so far. Missy can go back home dressed the way she arrived.
Jessica hands the 6 layer thick cloth diaper with pinked edges to Sally. Sally lifts Missy by grabbing both ankles and slips the thick diapers in place. Sally pins the fluffy white diapers on snugly like before. The same plastic panties are put back on Missy leaving one clean pair in the diaper bag.
“I won’t be needing another diaper in the morning,” Missy said, “Halloween does not continue the next day.”
Sally smiles at Jessica knowing Missy will be put in a clean diaper in the morning. After that the girls will do laundry and get clean diapers back in the diaper bag. One pair of plastic panties will need hand washing. Jeb is going home as a sissy diapered toddler girl ballerina.
“I have a little girl nightgown you can wear,” Sally said.
Sally gets the old white nylon nightgown with lace trim. It is hers from many years ago. The nightgown is short and has a rounded neck and puffy short sleeves. Sally has Missy stand and slips it over her head.
“Look how the nightgown goes great with Missy’s plastic panties,” Jessica said giggling.
Sally leaves the tights off but puts the white lacy top socks on Missy. Her white training bra is left on and fastened in the back. Jeb as Missy is tired when put in the crib to sleep. He still objects to sleeping in a crib. The sides are raised until they click locked.
“Goodnight sissybaby Missy,” both girls said sweetly.
Jeb is still adorable as Missy with bangs and curls at the end of his brown hair. The makeup still looks fine as the girls take a few pictures to remember this by. Rose enters the room to check on things. She notices Missy and said goodnight with a big smile.
“Toddler girls need their sleep so let Missy go to sleep,” Rose said taking the girls to the living room. “It was your party so do some clean up and get to bed girls.”
Rose helps the girls straighten up after the party. By 1 pm everyone is in bed for the night. Sally and Jessica sleep in the double bed next to the crib. This was a Halloween party everyone will remember.
The night is quiet and passes quickly while everyone sleeps. Missy wet her diaper twice during the night.
In the morning the phone rings around 9 am. It is Debra calling with urgent news. Her sister Laura sprained her ankle badly this morning and can hardly walk after seeing the emergency room doctor.
“Hello Rose, my sister Laura in Orlando sprained her ankle and can hardly walk,” Debra said, “I need to leave right away to help her for at least a week.”
“Oh no! That is bad news Debra,” Rose said, “Do you need me to watch Jeb while you are gone?”
“Yes, I hate to leave him home alone or bring him with me in this situation,” Debra said happy Rose offered.
In time Laura can walk with her ankle wrapped but she needs help right away now. Rose agrees to take care of Jeb who is still in the crib as Missy. Debra is packed and leaves for Orlando. Rose goes into the bedroom.
“Girls we have a house guest for at least a week,” Rose said, “Missy is staying here while her mother goes to Orlando to help her sister who sprained her ankle.”
“Jeb don’t have any clothes mom,” Sally said, “I have lots of old clothes he can wear as Missy.” “We better wash and dry diapers this morning.”
“Yes sweetie, we will keep Jeb as Missy since he has no other clothes to wear,” Rose agreed, “Jessica can stay a few more days and help babysit Missy.
“I will be glad to stay and help babysit,” Jessica said.
At this point Jeb is wide awake and heard everything. He is not happy this occurred or about remaining Missy still in diapers. He objects to being changed into a clean diaper and kept in diapers as Missy for a week or more.
“I don’t need diapers so don’t put another one on me,” Jeb stated firmly, “I will stay here if I have to but we can get our apartment key from the office.” “I can get my boys clothes and pack a suitcase.”
“No need to go thru all that trouble sweetie,” Rose replied with a smile, “Sally has clothes you can wear.”
Jeb as Missy struggles as Sally lifts him out of the crib after lowering one side rail. Missy is picked up and placed on the diaper table. He is easily kept there as Sally removes the plastic pantries and a wet diaper.
“You are going to love being diapered day and night for at least a week,” Sally said with a smile. “I have pretty little girl’s clothes you can wear.”
In a short time Missy is cleaned up, properly prepared, and pinned in a thick clean cloth diaper. The clean plastic rumba panties are put on Missy. She stands and her nightgown falls in place.
“We know you love your diapers and girl’s clothing,” Jessica teased, “I am changing you next time.”
Jeb as Missy is left in her white nightgown to have breakfast. The girls set up a highchair while Rose puts the wet diapers in the wash machine.     The End