Sissy Summer Vacation

[sweatergirl]

Its been a while but I am going to pick up with Pussey's experience as a total sissy! I am not going to redesribe the characters so if you did not read Sissy's Miserable Life, you might want to at least read the first and last chapter just to get introduced to the characters.



At the Beach



 Brit loved her beach house. She and had first husband had built it, and it remained hers. It was a large two story home about one block from the beach. It sat on wooden stilts, about 5 feet off the ground to protect it from ocean storm surges and had a large porch going around the first floor and a large deck off the master hall and front bedrooms on the second floor facing the water.

 Brit and Todd drove down to the beach in Todd's truck because Todd wanted to bring some new cabinets he had made for the Master Bedroom to hold a new large HD TV. Kathy and one of  daughers, Amy had driven in Kathy's convertible, while Brit's daugher Carol and her niece, Wendy had driven down in Carol's car. Everyone was in t-shirts and shorts as it was a beautiful hot sunny August day and everyone was looking forward to two weeks of nothing but playing, suntanning, swimming and going to fun bars and restauraunts in the evening. And no one had packed more than a few bathing suits, some more t-shirts, shorts and a few cotton shirts or tops

 That is everyone but pussey! pussey was dressed in a thick black lopi wool crewneck sweater that had a pink snowflakes fairisle type design running all around just below the crew neck. The hot wooly sweater was a size 34 and was truly tight and streched over pussey's 42 D stuff bra.The sweater was cropped so it just came down to pussey's waist. Brit had added some matching thick black wool leg warmers, pink lopi wool thumbless mittens and pussey's white wool baby bonnet tied with a big pink bow under his chin.

After he loaded all the luggae, Brit called pussey into the breakfast room where everyone was just finishing breakfast. "Gee pussey you have such pretty sweaters!" laughed Wendy. "But they don't cover much do they?

Amy chimed in " yes and your widdle wee-wee looks soooooooo very red and sore from yesterday ". And Amy was right, pussey's wee-wee was still very very sore and sensitive following the smacking it had endured yesterday, though at the capsasian had finally worn off.

"Amy I do think pussey needs something for that wee-wee, would you go into the study and I think you will find something" said Brit with a smile.

Amy went to the study and soon was back with a strip of pink burlap. "Is this what you meant Aunt Brit?.

"Yes Amy, now why don't you tie a nice big bow around your Uncle's wee-wee." "and tie it very tight dear, we don't want it to fall off", said Kathy, laughing at the thought of how ridiculous her sissy brother-in-law was goingn to look with a big pink burlap bow.

"pussey get over to me rigth now" said Amy, who was beginning to appreciate just how much of a submissive sissy pussey was. The poor sissy walked over the stood before his niece. Amy took the coarse pink burlap strip and first wrapped it around pussey's hairless balls, and pulled in tight, causing the sissy to wince it pain. Then she tied a second bow on the middle of pussey's shaft, making sure that burlap was tight and was flat againt the poor wee-wee so as to continue to irritate it.

" how cute your red wee-wee and pink bow look against your black sweater" said Wendy.

Brit scraped the crumb, and any remaining uneaten food from the table into a dog dish. "Lick your bowl clean pussey, then do the dishes, clean everything up and we will be off to a fun two weeks at the beach!

[sweatergirl]

Sissy Summer Vacation Part 2



 pussey ate his breakfast scraps on all fours out of the doggie bowl. Wendy, being the considerate niece she was, had noticed how dry pussey's breakfast looked so she came over, and dropped a big wsd of her spit into the bowl. Brit loved that her nieces were clearly understanding pussey's place in the household " Why Wendy that was just so thoughtful of you, I am sure pussey's breakfast will taste so much better now". The poor sissey looked miserable as he licked up the scraps with his niece's spit on top.

 Once everythng was cleaned up, everyone got into the cars to leave. "pussey you will ride with Ms Kathy and Ms Amy in their convertible.

But since you failed to say thank you to Ms Wendy for her addition to your breakfast you will have to be punished yet again." Everyone waited wondering just what Brit was going to do.

Brit pulled out a hugh black dil-do-easily 10" long and 2" round. She walked over to pussey who was standing in the drive way in his short sweater and knee socks with his rear and burlap bowed tied wee-wee exposed. "Bend over pussey" she said as she grabbed the chin strap of the sissy's big baby bonnet and yanked it down. "

"Mom" said Carol with feigned concern, "you aren't going to put that up pussey's rear with some lubrication, it will rip the poor thing apart."

Kathy quickly opened a bag " here sis, I have some more capsasian" and with that she opened the tube and coated the dil-do.

"Oh you are so thoughtful Aunt Kathy " giggled Carol.

pussey's eyes open in pure terror. He began to squirm, but to no avail.Brit took the big black monster and with no concern for the bent over sissy slave, shoved the capasian coated dil-do deep up his rear end.

Within seconds the sissy was squirming and writhing, his rear end doing obscene circles, hopping up and down on his feet as the burn from the capasian intensified up his rear end.

Carol, who had no use whatsoever for her sissy step father, said" You know Mom, pussey's wee-wee is still so red, I bet it would feel better out in the fresh air"

"Carol is right " said Kathy " the fresh air blowing on that wee-wee should feel really good". Todd, who had been quiet, but also enjoyed seeing his lover's sissy husband suffer, then spoke "Kathy since you have the convertible, why don't we have the sissy ride with you".

"Todd, that is just what I was thinking" said Kathy with a grin.

Amy, who was going to drive with her Mom, asked " but Mom I thought we were going to drive with the top down." "We are" said Kathy "and your uncle can ride in the back seat. " With that Kathy grabbed the sissy's and  pushed him over to the car. "Go sit in the back seat pussey"

pussey got in the back of the car, and gently sat down, but even so the dil-do was pushed further up his now sore invaded a..s hole.

"spread your legs wide apart pussy" Kathy ordered. "Amy and Wendy would each of you get some rope from Todd and tie each of pussey's ankles to the brackets under the front seats so his legs are spread far apart. " The two girls readily complied and soon the sissy was sitting spread legged in the rear of the car with no way to bring his legs together, thus leaving his wee-wee and balls fully exposed. " Todd be a dear and tie the sissy's elbows together behind him so he doesn't do anything nasty in my car. I want them tied together very tight ." Todd shoved pussey forward, grabs his arms and pulled them back  and tied them together at the elbows."

Meanwhile Carol had been busy with a large piece of white cardboard, using a dark pink marker she had written ' I AM A BAD SISSY WITH A WIDDLE WIDDLE WEE-WEE'  on the cardboard , then had punched two holes near the top and had run rope through the holes. She walked over and hung the sign aroud pussey's neck so that the front was pushed out by his 42C chest but leaving his burlap wrapped balls and wee-wee fully on display so anyone passing by could see them.

"Ok I think we are ready to go" said Brit, "I am sure it will be a nice drive but there will be lots of traffic and the road is very bumpy so go slow sis."

Kathy laughed, "No problem "

"Hold on Mom" Amy said. " it always hard to hear in the back seat with the top is down so I think we should do something to make sure pussey will know when we want to talk to him." With that Amy took another  length of coarse rope and tied it tighly around the sissy's wee-wee. She got into the car and pulled the rope through the arm rest. "Now pussey when we want your attention I will just yank on this rope" and with that the teenager gave a sharp tug which forced the sissy to thrust his hips forward or have his sore wee-wee pulled painfully away from his body."

"Good idea Amy" giggled Brit." I am sure he will pay attention to you during the drive".

With that the two cars and truck left together with Kathy's convertible, top down in the middle. Kathy turned the AC so that Amy and she would be nice and comfortable in front. For pussey dressed in the thick tight ithcy lopi pink and black sweater ,matching leg warmers, mittens and his baby bonnet with a big dil-do up his rear and his burlaped ribboned and leash tied wee-wee on display, the rid was going to be anything but comfortable!

[sweatergirl]

At the first stop light, Kathy looked back at her boud and displayed sissy brother-in-law. 'Amy, pussey is probably going to sweat a bit in the hot sun as we ride, and don't want the sissy to stain the white leather seats. Be a dear and jump out and grab the black wool blanket in the trunk and slide it under you Uncle so the seats are protected"

Amy quickly did as her Mom asked. As she grabbed the coarse wool blanket, she realized how scratch and itchy is was.

"OK pussey raise your a..s off the seat so I can put this nice soft blanket under you" Amy said. The sissy, having little choice, did as he was told .

Amy slid the blanket on the seat, jumped back into the car and grabbed her wee-wee rope leash just as the light changed and her Mom shot forward. Amy yanked on the leash, forcing her sissy uncle to lift his hips so that his wee-wee would not be pulled off, and then fell back.But as soon as he did, he felt the coarse wool blanket against his still very very sore spanked rear and he thrust his hips up to get away from the blanket.

Of course he could not keep up like that for long, and as soon as he dropped his hips he began squirming as he felt the itchy wool blanket.

Kathy and Amy just laughed watching the poor sissy squirm.

As they drove cars honked as they past the sissy display. Amy kept on yanking the wee-wee leash forcing the sissy to lift his hips. As Amy anticipated, the sissy soon became tired and after each hip thrust up he would drop down hard, driving the hugh capasian coated dil-do deeper into his rear. The poor sissy was soon crying and moaning, but all his sister-in-law and niece did was giggle and laugh at him.

Soon they were a long traffic backup  for the bridge toll both. Another car pulled up beside them and a young woman leaned out "What's with the sissy in the back" she asked Kathy." oh he is being punished".

Since the traffic was truly crawling, the woman got out of the car to take a closer look." Hey you guys have to see this" she said to her fellow passensgers, all women. and soon 3 other women were had rolled down the car window and were looking at the sissy and laughing.

"pussey wave hello to the nice women" said Amy. pussey could not wave as his hands were tied under his rear end. "Oh " said Amy, you can't waive with your hands so just shake your wee-wee instead."

The sissy hestiated not wanting to further humiliate himself. All of a sudden he felt a sharp tug on his wee-wee followed by more tugs as Amy yanked hard on his wee-wee leash. "You better listen to Amy" said Kathy," or I can assure you sissy you will suffer".

With that the sissy began shaking his hips to make his wee-wee "waive".

The women in the next car were hysterical watching the sissy make such a spectacle of himself.

And for the rest of the ride the sissy had to do his wee-wee waive to every car and truck that passed. By the time they got to the beach it was hard to tell who had more tears in their eyes- pussey crying from his shame and the pain of the dil-do, his sore yanked on wee-wee and the hot itchy sweater outfit, or Kathy and Amy from their laughing at pussey.

[sweatergirl]

Part 4



     As soon as everyone arrived at the beach house, they quickly changed into bathsuits and were off to enjoy the ocean and beach.That is all except pussey. Brit had instructed her sissy husband to unpack and neatly put away everyone's clothing, make the beds, scrub the bathrooms and toilets and then wash all three cars. She had untied his hands and taken the sissy sign off. She had of course put pussey back into his hated chasity device to make sure he would not do anything naughty. Of course his wee-wee was soooo red and sore both from the smacking session the day before and Amy's constant yanking of the coarse rope leash during the ride down that is was unlikely the poor sissy could even touch himself much less play with it.

Left in the cropped sweater, knee socks, bonnet and mittens with his wee-wee and rear exposed there was no chance the sissy would try to leave- and if he did where could he go with no money and looking as ridiculous as he did.

Some 4 hours later everyone returned home to see pussey washing the cars. He had drawn a small audience as the cars were all in front of the beach house and there was no way the sissy could cover his exposed wee-wee and rear. As Brit walked up to the house, a middle aged couple stopped her " Is that your husband", the man asked Brit. Brit was always very open about her relationship with her husband. "yep its is", she said.

"Wow that must have been some bet he lost", said the man. "where did you get the idea he lost a bet" asked Brit. "Well that is what he told us when we asked why he was washing cars in a thick wool sweater and baby bonnet with his  thing exposed" said the woman with the man, obviosuly his wife. Brit held out her hand" Hi first let me introduce myself, I'm Brit, and no he did not lose a bet. He is a sissy maid and has to do all the house work. The outfit is just to make sure he remembers that he is a sissy".

"My name is Laura and this is my husband Craig" said the wife shaking Brit's hand. "That is really amazing. I have read about people doing things like that but always thought is was just fantasy. Gee Craig, I wonder how you would look in one of my fuzzy sweaters", Laura said with a smile. "No, don't get the wrong idea Brit, Craigi is no sissy". Craig laughed, "you can say that again." Just then Todd came over. Brit introduced him to Laura and Craig as her "friend".

"Is he everyone's sissy maid?" asked Laura. " Brit answered yes.

Just then Amy and Wendy came over. After being introduced to Craig and Laura. Amy asked Brit in a sweet innocent voice "Did pussey give Craig and Laura a proper hello? Brit did not understand her niece at first, but then Kathy chimed in " Yes Sis, Amy spent the entire ride down here teaching pussey how to waive hello".

Brit turned to her sissy husband. " Did you say hello as you were taught",

The poor sissey mumbled ,' no, Ms.Brit.  Wendy grinned" did you hear the word he used, the sissy said the no word."

Brit turned to pussey " pussey first you lie, then you fail to greet Laura and Craig as you have been taught and then you use the 'no' word. I think one sissy is in for some strong discipline. Now say hello and apolgize for lying and tell these nice people just why you are dressed like you are.

The sissy slowly turned to face Laura and Craig and began shaking his wee-wee up and down, his "hello" waive. " pwease pwease, i am soooooooo sorwy for saying i wost a bet. i amm a sissy with a widdle widdle wee-wee, pweease i am sooooo sorwy for not telling wo thad."

Laura could not believe what she was seeing and hearing and could not help but begin laughing. Craig just grinned at the sissy.

"is that his punishment" asked Craig. "No not at all" said Brit, "why don't Laura and you join us for coc-ktails later and you can see how a sissy is punished. " Laura quicly agreed and then took Craig's hand. " We will be glad to join you "

[sweatergirl]

PART  5



 Craig and Laura dropped by Brit's beach house around 8 pm. Brit, Todd, Kathy , Wendy and Amy were sitting on the rear screened in porch having some beer and pizza.

"Glad you two came over" said Brit to her guests. " With that Todd handed them two beers. " Grab some pizza" Todd said. Craig and Laura did just and pulled up two more chairs to the table. The sun was just staring to set and it was still warm and humid, the cold beer tasted great.

Laura looked around and not seeing pussey asked where he was.

Brit stood up and grinned "Come with me". The two women left the porch and went through the kitchen toward the side of the house. Brit opened a door to a small windowless room that had 4 garbage pails, an ironing board, on some shelves were cleaning supplies and near a door leading to the side yard was a large pink kitty litter box filled with kitty litter. Across from the garbage pails was an adult size pink crib, and on the floor was a 3'ft wide by 4' long by 3'high metal dog cage. And in the dog cage was pussey. The sissy was on all fours with a big pink leather dog collar around his neck with a short leash that was wrapped around the bars at the front of the cage making it impossible for the sissy to move his head. As Laura walked around the cage, she saw the naked sissy's legs spread apart in the rear with each ankle locked to a side of the cage. His sore wee-wee was stilled locked in the cruel chasity device but a piece of rope had been threaded through a "D" ring on the chastity device and pulled back and tied a rear bar of the cage, yanking and streching his balls straight back. Over the sissy's head was a thick wool knit baclava (??spelling) with only a small opening for his mouth. The sissy was streched apart in the small cramped cage, unable to move. If he tried to move forward his balls were yanked back and he could not move backward since his neck was tightly leashed to the front of the cage.

Laura looked for a few seconds than began to laugh. " Brit that is amazing. I never saw anyone so uncomfortable and in such a humiliating position in my life. Can Carl see this?"

"Of course " said Brit. "I will get him while you enjoy pussey , and you can use this cane to make him "dance" for you." With that Brit took a bambo cane leaning against the cage and put it through the cage bars and poked the sissy's stretched out balls. The sissy tried to squirm way but could not and helplessly yanked both his balls and neck.

Brit was soon back with Carl who gasped " wow is that the sissy's punishment for this afternoon?

"Oh no "said Brit, " pussey is in the cage just to think about what he did today and how he will be punished." Whle Carl and Brit talked, Laura was having fun jabbing the sissy's balls and watching his helpless struggles.

"you know its really warm in here" said Carl." is the ac not working?"

Brit laughted " Carl when Todd added this room we decided not to waste money on AC. I mean its only for garbage, storage and for pussey to use."

Laura sniffed " the garbage doesn't make it very pleasant".

Brit giggled " I guess its suc-ks to be a sissy!"

[sweatergirl]

Part 6

While Craig and Laura went back to the porch, Brit unlocked pussey and lhad him crawl out of his cage. Connecting a leather leash to his pink dog collar Brit dragged the sissy to the porch.
Brit left pussey on all fours in the corner of the porch facing the wall. "Don't move or make a sound, pussey" Brit said in a firm voice.
Everyone chatted for about 30 minutes, not paying the slightest attention to pussey.
"Ok everyone" said Brit,' it is time to deal with pussey". Brit had the sissy crawl over and then stand in front of everyone with his legs spread apart and his hands on his head.
"First some new rules for our stay at the beach" said Brit.
"Carol, Amy and Wendy ,, the three of you are in charge of what pussey wears or does not wear while we are here. And Amy and Wendy I asked your Mom and she is ok with the two of you having the same control over and right to punish pussey as the rest of us do."
Amy and Wendy grinned from ear to ear. " You mean Aunt Brit, we can do WHATEVER we want with and to pussey." "You got it" said Brit.
Kathy chimed in  " but girls if we think you are not being strict enought then both of you will get spanked! So I expect you to try hard to make your uncle nice and miserable". Kathy luaghed as she said the words and the girls understood.
Amy and Wendy nodded. "oh don't worry Mom" said Amy,"pussey is going to be the most sissyish dressed sissy around" and said Wendy," the most sorry sissy you ever have seen."
Wendy then whispered to Amy. and then said" and pussey our first order to you is that since you are such a widdle widdel baby, you will wear diapers as long as we are here and use them! And you must ask, no beg, our permission to do anything in your diapers. If you go without our permission , you will have the worst case of diaper rash ever."
"Girls I think you will great with pussey" said Brit.

[sweatergirl]

Part 7



"Diapers" said Brit with a loud giggle." how perfect for a widdel widdle sissy ".

"So sis is that pussey's punishment for his back talk and bad behavior this afternoon" asked Kathy.

"No not at all" said Brit.

Laura who was clearly getting into the fun of humiliating pussey clapped her hands " Can you wait a minute Brit, I need to go to the little girls room". "Sure Laura" said Brit as she leaned over and whispered into Laura's ear. 'Oh my" giggled Laura.

Soon Laura was back. Brit yanked on pussey's leash, pulling him back down on all fours. "Everyone just follow me" said Brit. Brit walked toward the bathroom pulling the leashed sissy . Everyone crowded around the door looking into the bathroom. Birt stood with pussey, in his thick pink wool baclava covering his face. What the sissy could not see was a big bar of ivory soad with a long piece of rope tied around it.

"pussey you are going to learn to speak only when spoken to, and then only in the most respectful way " said Brit. "Mom. are you going to wash pussey's mouth out with that soap bar"asked Carol.

"Yes I am Carol, but first I need to get the bar nice and soapy. Usually one would use hot water, but I have a better way thanks to Laura." With that Brit put on a pair of rubber gloves , took hold of the rope around the  soap bar and dunked the soap into the toilet.

"Since pussey talked back to Laura, I asked Laura not to flush the toilet before, so now instead of hot water, I am dunking the bar in Laura's hot pee!" While everyone watched and laughed, Brit grabbed the pee soaked bar of ivory soap. "Get up on your knees pussey" Brit barked as she yanked on the leash. pussey had no choice but to obey. "Now open wide sissy " said Brit. pussey tried to keep his mouth shut so Brit just gave him a quick hard kick on his b..ls. pussey opened his mouth to moan and as soon as he did, Brit shoved the pee covered soap deep into his mouth and began to wash his mouth out.

"Yummy, yummy " giggled Amy. "Make sure you wash pussey well' laughed Wendy.

pussey struggled and squirmed but the soap was lodged deep into his mouth and soon his mouth was filled with soapy pee tasting bubbles.

"Dont you dare spit out one drop" said Brit as she yanked on pussey's leash. "Laura would you like to help?: asked Brit. Laura walked over, put on another pair of gloves, and smiling at pussey removed the soap bar and dunked it back into her pee in the toilet bowl. Satisfied that the bar was fully soaked,  she took it and , like Brit, shoved it deep into pussey' s mouth and then began pulling it in and out."suc-k it sissy, suc-k it hard" ordered Laura, who was totally turned on by the domination of the poor sissy.

"Gee I have never seen a mouth washing like this" said Todd. Craig nodded " I bet the sisssy never wants to wash with soap again"

Finally after 15 minutes more of having his mouth washed out with the pee soaked soap, Brit took the bar out of his mouth. She pulled the sissy's face over the toilet so he could spit out the soap and bubbles, but of course the foul taste was left.

"I don't think pussey will be saying No or lying any more" said Brit. "But just to drive this lesson home, I think a good paddling is in order". With that she handed the pink painted sorority paddle with the drilled holes in the business end to Craig. " I think 25 from you and Laura should do the trick".

Craig and Laura paddled the sissy with gusto till his rear end was brite red and steaming hot. As soon as they were done the sissy began doing another "spank" dance to everyone's amusement.

Brit grabbed the leash and pulled him to the corner of the porch. "hands on your head, nose against the wall and don't you move for 30 minutes or we will double the amount of smacks you get."

With that everyone went to have a few after dinner drinks, that is everyone but pussey who could only stand in the corner with the taste of soapy pee in his mouth, his red rear on display.