Sissy Summer Vacation

[sweatergirl]

Part 8

 Carol was awaken by her two cousins first thing the next morning.

"Carol lets get pussey dressed for today" said Amy.'After all the sissy has sooooooo much work to do, scrubbing all the bathrooms and kitchen floor again, sweeping, washing and ironing everyone's underwear and clothing from yesterday,'

"and don't forget Uncle Todd wants the cars washed and waxed again" laughed Wendy " and pussey has to bring all the beach chairs, beach umbrellas, towels and coolerr to the beach and set up everything for all of us first thing"

Carol yawned " ok then lets get the sissy ready"

With that the three women walked backed through the kitchen to the laundry/garbage room which was also pussey's room. The sissy was locked in his pink baby crib, in a classic spread eagle position with each hand tied to the crib railings and his feet also spread apart and tied to the crib sides. Brit had put him a white baby doll pjs covered with lace and pink bows over three pair of thick overnite diapers. The sissy had spit out his big pink p..s pacifier which now hung down his chest.

"Wow it sure is hot in here" said Wendy as she looked down at her sissy uncle. "and garbage oder is not too pleasant either" said Amy with  a smile.

The poor sissy looked up at the three girls. "my wiaper tis wery wet, pwease pwease take it off, pwease".

Amy laughed outloud. " oh my did pussey wussey go wee-wee. Is pussey wussey all wet like a betsey wetsey doll"?

Carol looked down with some disqust at pussey. " I certainly don't plan to clean pussey up. So unless one of you do, I think pussey should get use to wear wet diapers."

"ohhh N- I mean pwease change me" said the sissy , stopping himself from using the dreaded "No" word.

"Did I hear a No from the sissy" asked Amy with a big grin.

"Yep thats what I heard" said Wendy.

With that Carol untied the sissy's spread legs while Amy pulled off the wet diapers. Carol whispered to Amy who giggled as she took the wet diapers and place them over pussey's face with the pee stained side facing inward.

Wendy grabbed the big p..s pacifier and shoved into pussey's mouth through the diaper so now the sissy's mouth was filled with his own pee soaked diaper. Wendy wound the pink rope at the base of the pacifier aroud pussey's head so the pacifier and diapers could not fall out of his mouth.

The poor sissy shoke his head and tried to protest but his mouth was so full he could not utter a sound. All he could do was suc-k and taste his own cold pee.

Just then Brit and Kathy walked iin, both taking one look at the diaper faced sissy and breaking out in gales of laughter.

"HI Mom" said Carol," We came to get pussey dressed and his diapers were soaked and then he said the "N" word again. So I thought the punishment should fit the crime."

Looking down at her sissy husband, dressed in his lacey baby doll top, with his little thing in cruel chastity and on display and his faced covered with pee diapers, Brit shook her head , and then tickled pussey's balls.

"And just think pussey the day has just begun!"

[sweatergirl]

Part 9

 Carol finally pulled the pacifier out of the sissy's mouth and took pee soaked diapers out of his mouth and off his face.

"Now you be a good pussey baby or you will tasting your diapers for the rest of the day" and with that Carol gave the sissy a hard smack on his rear end.

"Mom can you unlock pussey's little thing "

Brit looked at her daughter , gave a little shrug and unlocked the cruel chastiy device and pulled off the sissy's p..s.

pussey immeadiately got excited, hoping that the girls intended to let him finally c..m.

Wendy laughed " pussey must think he is going to get some relief, though with such a widdle widdle wee wee I don't see why he needs any"

Carol looked down at her frustrated step father " Not a chance pussey, you haven't earned the right to c...m yet."

pussey heard his step daughter and wanted to protest, but realized it was hopeless and just frowend.

Meanwhile Amy grabbed a small bag. "Are we going to clean pussey up first before diapering him?" she asked.

Carol and Wendy both emphatically shook their heads no. " pussey has to learn to do his stuff only with our permission. And I think leaving his damp will lead to a nice case of diaper rash which is a perfect punishment " said Carol.

"Ok with me" giggled Amy, as she pulled out a stack of diapers from the bag.

Kathy , who with Brit, was just watching let out a gasp " oh my is that what I think it is?

"Yes Mom" said Wendy. " We made some very special diapers for pussey"

pussey squirmed some more as he saw the special diapers They were made from burlap!

"But before we diaper baby, lets make sure he is all nice and shaved" said Carol as she took a razor and began shaving the sissy's crotch. Even though pussey was already shaved down there, Carol shaved him again so he was totally hairless from his crotch to his rear. She made no effort to be gentle, and in fact shaved back and forth till pussey's crotch was red and irritated.

Wendy quickly took one burlap diaper and slip it under pussey's a..s and then pulled it through and over his  damp crotch, making sure first to take his dic-k and pull it back under him so it pointed toward his rear.

She pulled the burlap diaper tight , and then added three more layers of burlap diapers making sure the prickly coarse fabric pressed right against pussey's p...s, balls and rear end. Using two pink diaper pins she fastened the diapers on either side.

Amy then added three more thick soaked cotton diapers over the burplap and tightly pinned those down.

Brit and Kathy just watched with amused grins.

"Now we don't want you to leak" said Wendy " as she then pulled on a pair of pink rubber pants with ruffles across the rear.

"Walk for us pussey" Carol commanded.

pussey struggled to get up and climb out of his crib. He felf a hard wack on his rear, though the layers of burlap and cotton soaker diapers cushioned the smack.

Then he tried to walk but with the layers of diapers he could not close his legs together so all he could do is waddle like a toddler. And with each step he felt the coarse burlap rubbing his wee-wee and rear, causing extreme itching.

The five women clapped their hand and laughed at the sight of the waddling sissy.

" Wow I think the rubber panties are really going to make the sissy sweat" said Kathy.

"Yep Aunt Kathy," said Carol" that is just what we thought. The itchy burlap against his already pee soaked skin, sealed in thick rubber pants will soon feel like a furnace down there."

Amy then took out the rest of pussey's outfit. There was a hot pink baby dress knitted in fuzzy mohair, with puffed short sleeves, a high waist with a big bow just below his chest, and then a skirt that barely came to his waist that flared out, showing off his rubber pants and diapers. Cute little white wool socks that folded over with pink laces went on his feet, with pink mary janes strapped on. A nice big pink wool baby bonnet and matching mittens completed the sissy baby outfit.

pussey looked in horror at  the outfit, but could do nothing but let them dress him. Just as Carol had said, he began feeling the warmth between his diapered legs. And just like a baby, the sissy began to cry, much to the amusement of the five women looking at him.

[sweatergirl]

Part 10



 Kathy gave sissy a wicked grin as she pulled one last item for his outfit out of a bag. She held up a pink leather baby harness for everyone to see.

"waddle over here pussey" Kathy said. The sissy slowly waddle over to Kathy. She fit the harness down over his chest, pulled his hands through on either side, with each wrist being chained to the side of the harness, then Kathy pulled the straps down through his legs and back up and fastened them to the rear of the harness. She then took the shoulder straps and brought those over his shoulders, crossing in the rear and fastening to the harness.  On the front of the harness, in the middle was an emblem shaped to resemble a p..nis. On the straps and emblem were little bells.

"Now we will know wherever pussey is!" laughed Kathy" and here are some pink leather reins that can be hooked to the harness to make sure the sissy does not get lost."

"And I see there is just enough slack in the wrist chains so pussey can scrub toilets and floors, do laundry and serve us" said Brit. "Sis that is perfect!"

The poor humilated sissy could only stand there in his pink wooly short dress, bonnet, mittens with his little baby harness, his crotch diapered in successive layers of coarse scratchy burlap, heavy cotton and thick rubber pants.

"Now pussey, if you are a good sissy girl we will potty train you " said Brit.

"When you have to pee you are to hold your hands up, wiggle your bottom back and forth like you are shaking your little wee-wee and say very loudy in your sissy lisp " sissy has to go tinkle tinkle""

"lets practice pussey" Brit ordered.

The sissy hestiated and felt a hard slap on his face. "Now  sissy" said his wife.

With that the sissy raised his hands to his side like a dog hold up its paws, and began wiggling his diapered bottom back and forth, sayind' thisssy hath to go twinkle twinkle" . "Louder, sissy, I can't hear you" said Brit.

The sissy's face was brite red as he almost yelled "thissy hath to go twinkle twinkle." to the amused stares of the women around him.

"And if you have to poop, you will move your rear up and down like you were trying to poop, and say "sissy has to make boom booms" said Brit.

"Now lets here the sissy " said Brit.  And poor pussey, now even more embarrassed began to bounce up and down saying "thissy hath to make boom booms" while the women were now laughing their asses off at him.

"And pussey, if any of us ever find so much as a drop of pee or poop in your diapers and you have not first did your tinkle or boom boom dance, you can forget getting relief for the next year!! " said Brit. "so keep practicing while we have some coffee."

[sweatergirl]

Part 11



The women, joined by Todd, sat inside the cool porch drinking their morning coffe. pussey was standing in the backyard, the sun beating down, in his pink wooly dress doing his potty training.

'sissy hath to go twinkle twinkle" lisped the sissy in a loud sing song voice, his hands held up at his sides.

"sissy hath to do boom booms" the sissy yelled again, bouncing his burlap diapered a..s up and down.

Wnedy clapped her hands with glee while Amy just grinned. Kathy and Brit giggled. Todd drank his coffee and smiled at the poor sissy.

Carol however wasn't satisfied. "pussey you better tinkle and boom boom with a lot more enthusiasm if you hope to get our permission to do your pee pee and poo poos."

The sissy double his efforts , and as he shook and boucned harder, everyone just laughed more at the ridiculous picture he made.

Before the sissy could feel sorry for himself, more humiliation befell him.

"pussey go into the shed and you will find a wagon, bring it out" ordered Brit. pussey waddled over to the shed, and looking in he saw a brite pink child's wagon. He pulled it out. "now pussey load up all our beach chairs, umbrellas,towels, and get the cooler with drinks from the kitchen.'said Brit.

Pussey did as he was told and soon the wagon was totally filled.

Brit got up and walked over to the sissy. She took pulled sissy mitten cover hands behind him, tied them together with coarse rope adn then tied a short rope from the rope around his hands to the handle of the wagon. "Ok sissy you are to pull the wagon down to the beach, Amy and Wendy will go with you to make sure you don't get into trouble. And when you get to the beach they will untie you so you can set everything up for us."

"He will be like a little girl pony pulling a cart" laughted Todd.

Amy attached the reins to sissy's harness. "Wendy we will need to stop by Kelly Sue's house, I promised her we would pick her up on the way to the beach". Wendy grinned. " That's fine sis, I am sure Kelly Sue will enjoy meeting our pony girl!!"

[sweatergirl]

Sissy's Summer Vacation- Part 12



 As if the pink short wooly dress which just reached the sissy's waist, under which the sissy had 3 pair of coarse burlap diapers and then 3 pairs of pee-soaked cloth diapers AND then a pair of pink frilly rubber panties, with white wool baby socks, pink mary janes, thick pink woolen mittens and a big pink wool baby bonnet were not humiliating enough, Carol pulled out a pink dog collar with little bells on it and clasped in around pussey's neck. Amy took the reins from the harness which went over sissy's chest and also had lots of little bells, all of which went tinkle tinkle as the sissy waddle off pulling the pink child's wagon which was by its handle to pusseyls hands which in turn had been pulled back.

Brit had handed whips to both Amy and Wendy- " just to make sure pussey obeys you" laughted Brit as she gave her nieces the whips.

  pussey began walking down the street. "lift those legs up pussey' said Amy as she brought the whip across the sissy's exposed thighs.

The poor sissy winced iin pain, but having no way to avoid his niece whippin him he sort of waddled along, raising his legs up high.

"sure is hot and humid today, Sis" Amy said to her sister. " even this t-shirt feels hot over my bathing suit"

"Yea, can't wait to jump into the ocean and cool up" said Wendy.

"pussey wouldn't you like to jump in the ocean" laughted Wendy.

"the sissy will have no time for that, given all the house chores and ironing he has to do" said Amy. then looking at pussey " and I want ALL my clothing freshly washed and ironed today!"

By now the wooly dress, bonnet and mittens were damp with the sissy's sweat. And just as the girls had thought, the combination of the burlap diapers covered with the pee soaked diapers and the rubber pants were having there intended effect. The trapped heat was making the now wet burlap miserably scratchy and pussey, who had been cleaned up from his peeing last nite, desperately wanted to scratch between his legs to relieve the tormenting itchy feeling.

The threesome- two beautiful teenage girls and one pink wooly sissy stopped in front of Kelly Sue's house. Kelly Sue , Wendy and Amy were all sorority sisters. Kelly Sue was another cute blond, about 5'8" with a great figure. She was sitting on the porch of her parents summer house talking with her Mom.

Kelly Sue took one look at pussey and began to laugh. the poor sissy was now standing in front of the house, squirming and trying to rub his legs together to relieve the horrible itch between his legs.

"Kelly Sue" said her Mom " I thought you were joking about Wendy and Amy's having a sissy, but I guess not. That is the most pathetic looking thing I have ever seen" and she too broke out laughing.

"Hi Kelly Sue, Mrs. Carr" said Amy. "Hi girls" said Mrs. Carr, why don't you come up here on the porch where it is nice and cool.

Wendy took the harness and tied it around the lamp post in front of the house, leaving the sissy with no way to move.

"didn't think you wanted the sissy with us" said Wendy.

"Oh no , no sissys on this porch!" laughed Mrs. Carr.

"Is that really your Uncle?" asked Kelly Sue. " tell us all about this"

[sweatergirl]

Part 13



"So girls, please tell me all about pussey" asked Mrs. Carr as she, Kelly Sue, Amy and Wendy sat on the covered porch cooled by a big ceiling fan.

Amy and Wendy proceeded to describe how thei Aunt had turned him into a total menial house sissy, how he was punished, made to dress as a wooly sissy girl and baby, and his potty rules. Mrs Carr and Kelly Sue just laughed. Kelly Sue loved the "Old McDonald Had A Farm" wee-wee smacking punishment.

"Was pussey crying ?" asked Kelly Sue. "just like the little sissy girl he is" said Wendy with a big grin.

"You know girls, pussey must be so hot and thirsty, dressed in his cute pink wool dress and bonnet. I think he needs something to drink." With that Mrs,. Carr went inside the house. Five minutes later she came out with a baby bottle.

"Come girls", said Mrs. Carr as she walked to the lamp post to which the poor sissy was tied.

 The women gathered around the sissy. " You must be sooooo hot with that big baby bonnet on your head, lets just take it off" said Mrs. Carr, and she untied the bonnet and put it in the pink wagon.

Wendy and Amy were wondering if Mrs. Carr was feeling sorry for the sissy. pussey seemed relieved, and certainly felt a little cooler with the the bonnet off.

But that certainly was not Mrs. Carr's intent. She pulled out some lipstick, and before pussey could react, began putting it on his lips. The lipstick was a wet glossy pink and she put on it really thick. "dont' want those lips to get sunburnt now that everyone can see your face!" said Mrs. Carr. And pussey suddenly realized that while the baby bonnet had been hot and itchy, it had kept his face hidden. 'pwease can i have my bonnet back" whinned pussey.

Amy and Wendy picked up on what was happening as well. " Why pussey you should thank Mrs. Carr fr being so concerned. And every little girl loves to wear lipstick and show off to everyone!" said Amy.

Mrs. Carr then took the baby bottle and shoved it into pussey's mouth.

pussey made a face. "Why what is wrong" asked Wendy. "Gee", said Mrs. Carr, maybe pussey doesn't like hot water flavored with castor oil."

Kelly Sue, Wendy and Amy could not contain themselves as they laughed.

"you better drink every drop pussey." Wendy said as she looked at pussey.

"And I have two more bottles for pussey after that" said Mrs. Carr.

pussey suc-ked on the bottle, drinking the horid tasting water.By the time he was done with all three he felt bloated.

"Someone is going to doing a potty dance very soon" said Wendy.

[sweatergirl]

Part 14

 Just as pussey finished the third and, at least for him, thankfully last of the horrid hot water castor oil flavored bottle, three young women walked up to the hosue.
"Hi Kelly Sue, Hello Mrs. Carr" said one of the women. " Hey guys how are you" Kelly Sue responded. "Heather, Tracey and Kris, meet my sorority sisters, Amy and Wendy. Amy and Wendy, Heather, Tracey and Kris are all life guards on the beach here."
Amy and Wendy said Hi.
"Good to see you girls" said Mrs. Carr. "bet you are wondering about ths cute little girl and why she is tied to the lamp post"
The three life guards turned to look at pussey in his cute pink wooly dress.
"Well I have to say I am curious" said Heather. "Me too" added both Tracey and Kris." "I mean is that a guy?" asked Kris,  trying hard not to laugh .
"Well maybe anatomically its a guy" said Wendy, 'but he is really a sissy girl. pussey say hello to the nice women."
pussey paused every so slightly, so Amy picked up her whip from the wagon and smacked the sissy's diapered rear end. "Say hello sissey and tell them what  little sissy you are" ordered Amy, as Heather, Tracey and Kris watched.
pussey jumped, feeling the whip. ' mmyy name ith pussey, i am a sissy."The three life guards just looked and grinned.
"pussey is my Aunt Brit's second husband' said Amy. " And as you can see he sissy."
"Whats with the wagon and the harness" asked Heather.
And why is he wearing such a wooly dress" asked Tracey.
And what is underneath that dress" asked Kris.
Amy and Wendy explained how pussey had to take all the stuff to the beach, that his dress was a punishment outfit meant to make him look like a sissy girl and also be miserable to wear, and that he was wearing burlap and cloth diapers with rubber pants und the dress.
"So pussey is coming down to the beach?" asked Tracey. "Yes, in fact we need to get him down there to set everything up before my Aunt , cousin and Mom get down there. " said Wendy.
"Well thats where we are headed as we have to set up the life guard stand." said Heather. " Are you all ready to come to the beach now, we would just love to watch pussey for a while.:
"sure' said Kelly Sue, "just let me grab my stuff and lets go.Mom are you coming now?
"No Kelly Sue, you and the girls can take the sissy and go. I will be down there shortly.
Amy untied pussey from the lamp post. "get moving pussey", taking the harness and swatting the sissy's rear again.
30 minutes later Heather, Tracey and Kris were on duty as life guards. Amy and Wendy were sitting comfortabley on the beach chairs under the umbrella set up by pussey. Brit, Carol, Kathy and Todd, along with Kelly Sue's Mom had joined the girls. Mrs.Carr had told Brit about her hot water castor oil bottles.
"pussey do you need to ask us anything before you leave. " Brit said, llooking up at the sissy from her beach chair. " We all plan to stay at the beach all day, and remember what happens if you do anything in your diapers without permission.
"Sis, I bet pussey wants diaper food for dinner tonite" laughed Kathy.
The poor sissey had to go, but had hoped to avoid having to ask permission at the beach in front of everyone. But between the preasure and the thought of what he would have to do if he used his diapers without permission, he knew he had no choice.
'pussey hath to go tinkle tinkle" pussey said quietly humping back and forth.
"pussey hatht to do boom booms" pussey said again bouncing up and down?
"Louder pussey, I can't hear you " said Brit with an evil grin.
"pussey hath to go tinkle tinkle, pussey has to bo boom-boom," the sissy said in a louder voice.
" Sing it out loud pussey" said Carol,
"And put much more effort into showing us just what you have to do" said Kathy," because to me it doesn't look really have to go at all with those half hearted movements."
So the sissy began singing his potty requests and really shakng and bouncing up and down. The bells on his doggie collar were ringing and he was attracting lots of attention from people on the beach.
"Keep singing and doing your potty dance" said Brit. " I will let you know when and if I think you can do potty in your diapers."
The three life guards walked over to see what was going on. Heather began clapping , and was joined by others watching ' do your potty dance to the beat" said Brit.
Soon lots of people had gathered round to watch the entertainment.
One little girl asked Brit " is he being potty trained". Brit laughed " yes he is"
"Well my Mom makes my little brother sing his potty song for a long time before he can go. she says it is teaching him to hold it in."
"Yes thats a good idea" said Brit. 'We will keep him sing for a while to"
pussey was straining to hold his stuff in."pweeease psweaase, pussey has to go tinkkle tinkle and boom boom " the sissy was now begging and crying..
"Ok pussey go tinkle and boom boom" said Brit. pussey started to waddle away to do his thing in private. "Where are you going pussey" asked Brit.
'pussey it going to do tinkles and boom-booms' the now humilated sissy said.
"I said to go tinkle and boomboom, and I meant do it here so we all can watch" Brit said in a stern voice.
pussey looked at his wife in horror, but before he could protest, he began doing everything in his diapers. It was obvious to everyone.
"he is going potty" laughted the little girl.
"thats pathetic" said a man to another woman who were watching. "yes but it is hilarious" said the woman back.
Soon pussey's diapers were full with his boom booms and soaked with his tinkles.
Carol walked over to the sissy. " are you all finished pussey"
"yeth i am"
"Well then bend over pussey" and with that pussey's step daughter took a ping pong paddle she was holding and began smacking the sissy's full diapers taking care to smash the boom boons and make sure they were spread out and filled the burlap diapers.
"Just want to make sure your diaper rash is evenly spread" said Carol as everyone just laughed.