Sissy Summer Vacation

[sweatergirl]

Part 15



 pussie spend the next five days dressed in winter girl wooly sweaters, burlap diapers and wool tights, with thick woolen mittens and a wooly baby bonnet scrubbing floors, cleaning toilets, serving everyone at the house. There was no such thing as free time, as someone always found a menial boring chore for the sissy. He continued to have to do his tinkle and boom boom dances and , with permission used his diapers. Brit only allowed pussie to have his diapers changes once every two days, so for most of the time he smelled, and had loaded wet diapers. The result was a very nasty case of diaper rash which meant pussie constantly had a hot, burning, itchy rear. The rough burlap diapers did nothing to help the poor sissy, and so he was constantly squirming around to everyones amusement.

 Friday late morning pussie tackled the ironing. Brit insisted that pussie launder and iron everyone's clothing including their underwear! Sheets also were to be laundered and ironed daily. The ironing board was set up in pussie's "room", which had no ac, and constanly smelled of pussie's dirty diapers which were kept in a pail in his room until Brit allowed him to hand wash them in the backyard. Brit made pussie were 6" stiletto heels while he ironed, and he was leashed to a pole in the room so he barely move. A wooly turtleneck sweater, diapers, bonnet and wool mittens completed his "ironing" outfit and kept him miserable, hot and itchy.

pussie could look forward to a full afternoon of ironing that Friday. So he was totally surprised when Brit came in and told him he could stop.

"Its a bit overcast today pussie, so we are having people over this afternoon just to relax." pussie immeadiately worried that he would be made to serve and entertain. Brit could see the ooncern on his face. " Relax pussie, I have decieded that you have been working very hard and need a break, so this afternoon you don't have to do anything, just hang around." pussie could not believe his ears. "oh tankyou Mistreth".

Brit unleashed pussie from the pole. " Go take everything off, , wash off your diapers, and then you can use the outside shower and clean up."

pussie hurried off, and soon was in the shower. True the shower had only cold water as its purpose was for people to rinse off sand when they came from the beach, but still its was the first shower pussie had taken since they had come down to the beach.

As he stepped out of the shower , Brit and Kathy were waiting for him. Kathy examined his rear end.' I have never seen a case of diaper rash like pussie's" she said to Brit. " Poor pussie's rear must be on fire"

"yes pussie sure is a hot sissy" giggled Brit.

"Well sometime out of diapers would do pussie some good" said Kathy.

"hmm, well I see no reason why pussie needs diapers this afternoon" said Brit. "so pussie you can hang around with no diapers"

"but he needs something to wear" said Kathy with a grin.

"And I have just the outfit for a sissy who is hanging around to wear" Brit said with a giggle.

[sweatergirl]

Part 16



  "What do you have for pussie to hang around in" giggled Kathy. Brit slowly pulled something from a bag she had been holding. "My friend Darla Smith, who loves to knit, made this just for pussie" Brit said as she held up what could only be described as a baby romper.

Kathy took one look and roared. It was a one piece romper with very a very short panty bottom , a heart shaped bib on top with straps , the straps fasten to the top of the bib by big pom-pom buttons.

The panty bottom was knitted up of a thick coarse white wool with pink lace trim around the leg holes and a band of pink wool around the waist. The heart bib top was knitted up of a fuzzy mohair in dark pink. "Pussie" was knitted across the front of the bib.

'Lets get dressed pussie" said Brit, handing the romper to the sissy. The poor sissy, knowing he had no choice, put each leg trhroug the panty leg hole and pulled the romper up until the rounded tops of the heart shaped bib reached just passed his chest. Brit grabbed the straps and pulled the over his shoulders, crossed them in back and button the two straps to matching pom-pom buttons on the rear waist of the panty bottoms. Brit pulled the straps taunt so that the entire romper fit tight, with the coarse wool panty being pulled tight into the sissy's crotch and rear.

"Now twirl for Aunty Kathy and show her your romper pussie" Brit said with a stern look at her sissy spouse.

pussie twirled as ordered showing off the wooly romper, There was a big pink pom-pom  on each side of the panty, and 3 buttons on both the front and back of the panty.

Brit handed pussie a pair of pink wool baby socks with lacey bows which he obeidently slipped on his feet along with pink girl keds with lacey ties.

Then thick pink wool mittenswith matching pom-poms on the top of each mitten and another awful pink wool baby bonnet that tied with a pom-pom tie under the chin.

"now jump up and down pussie" . pussie jumped and Kathy and Brit again laughed for each of the pom-poms on the romper and mittens had a bell so as he jumped the bells went tinkle tinkle .

"What a perfect little baby girl outfit" said Kathy.

"Yes: agreed Brit. "Now pussie lets go show off our new romper."

Ohhhhhhhhhhhh, pweeeeeeeeeeeeeease, pweeeeeeasse, can't i just say here,? whineed the sissy.

Brit took one look and gave the sissy a hard slap on his face.

"just for that, you will crawl out, just like the big baby you are."

If pussie had thought he was going to have an respite from his constant does of humiliation this afternoon, he was clearly mistaken.

[sweatergirl]

part 17



 The sissy slowly crawled out the rear porch and into the backyard. Todd, Brit, Carol, Kathy, Wendy and Amy were all having cool drinks.Brit had invited Craig and Laura, Kelly Sue and her mom.

 The coarse wool panty part of his romper outfit added more irritation to his already suffer rear-end with its diaper rash. But the wooly bottoms also rubbed his free wee-wee, which for the first time in weeks was not in its cruel chastity cage or tied in some fiendish burlap bow. that is freed for the first time since the day before he came to the beach, when Brit had taken the chastity cage off so that she and the girls could punish the sissy by smacking his wee-wee around.

So as pussie crawled into the backyard his wee-wee did what was natural and began getting excited. Even though pussie's wee-wee was no more than 41/2 inches when it reached its maximum size, it still made an obvious bump against the tight tight panties. The sissy immeadiately realized what was happening and was trying desperately to will his c..k to get small before anyone could see how excited he was.

"Aunt Brit, look at pussie" said Wendy. " 'pussie must just love his new baby wool romper, just look at the bump in front".

Brit looked down at the sissy. "Stand up pussie and lets take a look".

The sissy slowly got up and quickly put his mitten hands in front of this panties to try and hide the small bulge. "SMACk" Brit wacked the sissy's hands away. "Don't be shy pussie, you hae nothing to hide". With that everyone laughted.

Wendy, Amy and Kelly Sue began singing " I see England, I see France, I see pussie's wooly underpants!" The girls could barely get the words out as the giggled and pointed to the poor sissy.

"OK pussie I said you could just hang around this afternoon and I meant it." Brit said as she grabbed her sissy husband's hands and pulled him toward an old swing set. However in place of the swing that had been there, there was now 2 bungee cords which were attached to the metal bar across the top of the swings. The bungee cords criss crossed each other at the bottom to create a seat of sorts.

"Ok pussie stand in front of your new "swing" said Brit with a wicked grin but don't sit down yet. The swing set was almost 12 ft tall, and the bungee cords appeared to hang down about half way.

Carol, Kathleen and Brit walked over to pussie, Carol took one of the sissy's arms and pulled it up along one of teh bungee cords which went to the top of the swing. She tied the sissy's wrist tightly to the bungee cord, while her Aunt Kathleen did the same to pussie' other wrist. As a result pussie was forced to stand on his tip toes.

Brit then unbuttoned the buttons which were on the rear of pussie's rompr bottoms. "Perfect fit" laughted Brit, " as she spread open the rear area to expose the sissy's a..h...e. Carol produced a big thick black dil-do and waived it in front of her step-father's face. pussie began to whimper when he understood what was going to happen. "I bet every sissy wants a big hard one!" said Carol. "But this does need some lubrication so it doesn't hurt the tender sissy." With that Carol took a bottle of Liquid Xra Strength Icey Hot and began coating the dil-do in front of the sissy's face. "Puts lots on Carol, we want to be sure its slides right in" said Kathy watching as her niece painted the dil-do with coat after coat of the icey hot.

Brit then took the icey hot coated dil-do and slowly shoved it up the sissy's a..s pushing it as far as it could go.

Brit then walked in front of her sissy husband who was starting to squirm a bit. She unbottoned the front buttons and pulled out his wee-wee for all to see.

"Not much there" said Kelly Sue's mom who was totally excited at what she was watching.

"Nope its a wee-wee alright" laughed Brit' but still we want to make sure it gets its fair share of attention." Brit took a small rubber ring and held it up.  Everyone could see that the inside of the ring had little rounded pin heads.

"Oh my" said Kathy " as Brit put the rubber ring, pins facing inside, over the sissy's still hard wee-wee and tighten the ring so it could not slide off.

Then Brit clipped a large weighted bell to the ring so that it hung straight down.

"Todd give me a hand please" said Brit. Todd grabbed pussie ahd hoisted him up and sat in down on the "swing seat" created by the two bungee cords. The cords streched down just enough so that pussie's feet were just touching the ground.

Todd then gave the bungee swing a hard push from the back and pussie swung forward. As he did his legs left the ground and the heavy weighted bell yanked down on the ring attached to his wee-wee, pulling the pins against his tender shaft. "OWWWWWWWWWW" screamed the sissy.

The sissy swung high and then began to swing back. He involuntarily kicked his legs, adding more momentum to the swing and tus pulling him back even further. The weighted bell stop yanking his wee-wee but as he swung back the dil-do was driven further into his rear. "OHHHHHHHHHHHHHHH" screethced the sissy feeling the burning sensation of the dil-do up his rear end.

And as he screamed he began swinging forward, meaning the bell again yanked his wee-wee. "OWWWWWWWWWWWW"

and soon the horrible rythm of having his wee-wee yank and the pins from the rubber ring pushed into his very sensitive wee-wee, and then swining back and having the dil-do shoved more deeply in his burning a...h. was established.

With his face framed in the wooly bonnet, the little pom-pom bells on his romper top and bottoms ringing, the sissy became the afternoon's entertainment.

Wendy ,Amy and Kelly Sue could not stop laughing. Brit could only grin, enjoying the total humiliation her sissy was experiencing. Kathy and Kelly Sue mom decieded to stand and push the sissy back and forth, higher and higher and the result was even louder sissy screams.

Later in the afternoon it started to rain. Everyone went up to the porch, that is everyone but pussie who was left to hang outside in his baby wool romper, his rear end buring and itching, his wee-wee sore and frustrated.

[sweatergirl]

It has been quite a while since I added the last chapter -July 28th to be exact. I will finished up Sissy's Summer Vacation and then, if there is interest, begin telling about pussie's home and work life. It may help for readers to go back to the July posting to refresh their memories about pussie.



Part 19

  Poor pussie was left strapped to the swing dressed in his itchy woolly romper with the icey hot coated butt plug up his rear and the cruel pin linged ring around his wew-wee for over an hour as the rain poured down. As often happens with a summer rain, it only beceme more humid as the storm ended, so not only was pussie bound into a hot heavy throughly soaked wool romper, but the air was thick and heavey as well adding to his misery. Of course pussie's diaper rash, which was made worse by the coarse tight wool romper rubbing against his rear only made him that much more uncomfortable

Pussie's wife Brit, her boyfriend Todd, pussie's step daugther Carol, along with Brit's sister Kathy and her two teenage daugthers, Amy and Wendy, their friend Kelly Sue and Kelly Sue's mom, and Brit's neighbors were all comfortably inside the cool house having drnks, talking and laughing themselves silly as they looked out at the bound sissy.

Finally everyone left .Brit anc Carol came out. "We all sure enjoyed having you "hang around" with us" said Brit with a cruel grin to her sissy husband. "did you have a fun afternoon?" The poor sissy knew he had to say yes as he wa never allowed to say the word "No" .

Carol chimed in " he must have Mom, look his wee-wee is all excited"- looking at her step father's p..is which Brit had left exposed.

"Oh I am so glad pussie enjoyed herself" Brit responded.

Brit and Carol freed pussie from the swing. "ok inside pussie, we are taking you out tonite as this is our last nite of summer vacation" said Brit.

pussie went to put his wee-wee back inside the romper and button it up in some effort of modesty.' Don't you dare touch yourself" scolded Brit". "Sissies have no modesty, and anyway there is almost nothing to see there".

Carol laughed 'just waddle back inside pussie with your widdle widdle wee-wee hanging out"

pussie had no choice. Given the thickness of the woolen jumper, and his diaper rash, all he could do was take small waddle steps back to the house.

Amy and Wendy, who had been given the responsiblity for dressing pussie each day were waiting ."oh pussie lets go, we are going to make you s0000000 pretty for tonite" Wendy said as she clapped her hands.

"We are all going to a club and we want to be sure you are a hot sexy sissy tonite so everyone will notice you. Isn't that what everyone hot girl-I mean sissy wants? asked Amy.

"Well answer Amy" Wendy said in a stern voice to her sissy uncle.

pussie looked down and mumbled 'yeth tats what i want"

"Speak up pussie.Tell us what you want to be tonite" Wendy said " or I will maybe you would prefer a nice hard spanking right now on your tender cute rear right now?

pussie certainly did not want a spanking on his diaper rash covered rear, so in a loud sissy voice he responded ' i want to be a hot sexthy sisthytontie".

"Well then we are going to make sure you get your wish" laughed Amy

pussie

"

[sweatergirl]

Part 20



pussie waddled back to his room with Wendy and Amy right behind.

"Bend over pussie" Wendy said. As pussie did as he was told, Wendy grabbed the end of the butt plug and yanked it out of pussie' rear end.

"ouch" cried pussie. Wendy was about to put the butt plug on the shelf when Amy said " geez Wendy that thing is dirty, don't you think pussie should clean it first before you put it away?"

Wendy looked at her sister and quickly understood what she was saying.

"You know you are right Amy" and she put the butt plug on the floor.

"pussie you need to get this butt plug nice and clean" Wendy said to her sissy uncle who was still bent over. pussie started to stand up.

"Where do you think you are going?" asked Amy.

"i am goink to take the butt plug and wash it at the sink" lisped pussie.

Wendy and Amy both grinned.. then Wendy bent down and looked into pussie's face"Not a chance pussie. You are a sissy and sissies clean butt plugs, dil-do's and c..ks with their sissy tongues,.Get licking girl and you better lick that butt plug till it shines"

Kathy walked in just as Wendy was done speaking. " Wendy, that thing was deep inside pussie's a..s, just think how dirty and smelly it must be"

"gee Mom am I being too hard on pussie" Wendy asked?

pussie looked up, hoping Kathy, being a doctor, realized how horrible it would be to have to lick the butt plug. Finally someone coming to his defense, pussie thought.

Kathy grinned"Oh not at all Wendy, I am just wondering how long it will take pussie to lick it clean as are leaving to the club in an hour. Just make sure pussie licks hard and fast."

Amy clapped her hands in delight. "You heard us pussie, get licking lickity split."

pussie looked at the horrid dirty big black butt plug. He wanted to say No but couldn't. He started to wimper and beg/" pweasse pwease let me wash it , peassssssse.

"We said lick and suc-k, so get going pussie" Wendy said and with that Amy, who was standing behind pussie, who was back on all fours, gave th e sissy as swift kick in his crotch. 'OWWWWWWWWWWWW" screamed sissy, clutching his wee-wee.

"Start licking or there will lots more of those pussie" said Amy.

pussie had no choice but to crawl so his face was over to the butt plug and lower his face until his lips slid down over it. It smelled and he could see how dirty it was, but he began licking and suc-king it to get it clean. The girls watched with huge grins. " Consider this a learning experience pussie" said Wendy. "yea sissy, you need to learn how to suc-k c...k to please real men." said Amy.

10 minutes later, pussie finished his task. Wendy leaned over to look at the butt plug. "Not bad pussie, it looks clean enough for now."

"Ok hop up pussie, go out and take a shower and get nice and clean, so we can get you all sissied up for the club tonite" said Amy.

[sweatergirl]

pussie went outside to take his cold shower- the awful taste of the butt plug in his mouth. No sooner had he stepped into the shower then Amy pulled back the plastic shower curtain.
"Put your hands on your head, face me and spread your legs wide open pussie" ordered Amy, with Wendy by her side.
"Just what I thought, Wendy, the sissy has some hair growing- not very girlish". Amy took a long handle scrub brush, pour some liquid on it and began to roughly scrub pussie all over. The scrub brush was hard bristled and Amy made no effort to be gentle. pussie squirmed and tried to move away. "Don't you move pussie if you know what is good for you" Wendy said sternly.
When she had throughly scrubbed pussie's front, Amy focused on his wee-wee and balls. She scrubbed them extra hard, making sure to lift the sissy's wee-wee to get all around it and around his balls. Then she made him turn around and she did his back, and finally had the sissy bend over.
"Ok sissy take your hands down and spread your a..s cheeks for me."
Wendy giggled as the sissy followed orders. Amy took the brush and scrubbed there as well.
At first pussie only felt the rought brush, but soon he felt some tingling and almost a slight burning sensation. After a few minutes, Amy told the sissy to turn the water back on and rinse off.
Amy pussie the bottle- it was Nair. And as pussie watched in horror, all his body hair from below is neck was soon flowing down the drain.
Amy and Wendy closely examined pussie. As they did, Brit and Todd came by. "Aunt Brit, Uncle Todd, look how cute pussie looks now" said Amy. Brit and Todd looked at the poor sissy standing in the cold shower totally hairless. " What a cute widdle sissy" laughed Brit. Todd grinned as well. enjoying Brit's sissys husband's humiliation.
Ok pussie, let's get you dressed as a "hot" sissy for the club tonite" Amy said as she took the scrub brush and smacked pussie's wee-wee.
The girls took the sissy into their room in the house.
"Lets get pussie' make-up on first" said Amy. They had pussie sit at the make-up table. Wendy first did pussie's finger nails in a glowing candy pink nail polish with stars and then did his toes to match. Amy put some dark pink eyeliner on the sissy first, then did his eye lashes, which were quite long, with sparkely pink. Next came some blush-on with more pink and white sparkles. Wendy did his lips with a frosty glossy candy pink lipstick. The girls had pussie put on long pink dangling pen-is shaped earrings with the little bells on the end.
Brit had not let her sissy husband have a hair cut since she turned him into a full sissy in May, so now his hair was long enough for Wendy to make two pig tails, one on each side, using pink yarn which she wrapped so tight that it hurt pussie.
"Stand up pussie" said Amy. She handed him a dark pink bra, that was at least one size too small for pussie. "put it on and make sure you use the last and tightest clasp" said Amy. pussie struggled to get the bra on- it felt like a tight band around his chest- he could barely breath. Wendy handed the sissy two gel false breasts to stuff the bra. " 42DDs" laughted Wendy. pussie could only groan as he felt the weight of the false breasts.
Next came thigh high pink fishnet stockings. Amy and Wendy just giggled as pussie wiggled into them with his wee-wee bouncing around.
Amy gave the sissy 6" stilleto pink heels with locks on each shoe. "We don't want you to lose your come-f..k me shoes "said Wendy as she locked each shoe on.
"Walk for us pussie" ordered Amy. pussie could only take very short steps so he would not fall. The heels forced him to stick out his chest, and sway his rear as he walks. "Very hot pussie" laughed Wendy.
Amy then gave him a true mini skirt- it was pink and white thick itchy wool with pleats. When it was on, the bottom of the skirt just grazed pussie's wee-wee. The slightest movement would have pussie showing off his wee-wee and rear to any one around.
"Usually the AC is on full force at these clubs" said Amy, as he handed pussie a hairy white angora/mohair cropped turtleneck puffed shortsleave sweater.  As pussie put on the sweater, he realized that while he now had 42DD breast, the sweater was at least two sizes smaller. Even worse it was knitted so that the chest area was more open weave so his bra clearly showed.
Amy and Wendy looked over pussie who only wanted the floor to open up so he could fall into a dark hole. "something is missing Wendy" said Amy.
Wendy looked and then went to the closet. She came back with a necklace for pussie. " I think this is it" said Wendy as she put the necklace around pussie''s neck. It was a silver chain with a hugh realistic pen-is which hung down between pussie's double ds!
"Perfect' said Amy."pussie you are now one 'hot " sissy!!

[sweatergirl]

Parat 22



Amy and Wendy each took one of pussie's hands and led him into the living room where Brit, Todd ,Caroland Kathy were sitting.

"oh my girls, pussie looks like a Barbie doll" laughed Kathy.

"She sure does" added Brit,"what with that tight fuzzy sweatr over her big boobs, that short short skirt that barely hides her widdle clit and thos come f..k me red heels, and those adorable pig tails. And I do love her pink glitter make-up. I am sure every guy is going to want a piece of pussie tonite"

"But I have a few additions to pussie's outfit" said Brit. "Walk over and stand in front of me, pussie."

pussie walked over in his little mincing steps, wondering what his wife had in mind. "Hold up that cute skirt pussie."

pussie looked around as Kathy, Todd and the girls just grinned.

"NOW" said Brit, "We don't have all day to wait for a stupid sissy to to as he is told" pussie jumped at his wife's stern command and lifted the skirt- all 10 inches of it, up.

Brit picked up some pink fuzzy yarn and and wrapped in back of the sissy's b..l,  tiying a huge pink bow which framed the b..ls, then took a pink scrunchy. She showed the scrunch to the others. " Carol thought we should dress up pussie widdle clitoris and so she took an old scrunch, cut down so if would fit over pussie and before gluing it  back together put little tacks inside it." Brit took her husband's wee-wee and slid the tack filled scruhcy over and just behind the head. The scrunchy was sized so that it could not fall off but as long as the wee-wee was not erect, there was no contact with the tacks.

"I call this a sissy clit prettyfier" laughed Brit "pussie walk over and show everyone how pretty your prettyfier is".

pussie minced over to Kathy and Carol " I think pink is pussie's color" laughed Kathy. Carol added " yes it sure is. Just don't get excited tonite pussie, you don't want those nasty tacks touching your pretty clit."

Brit walked over as pussie stood in front of Todd. She put a pink leather dog collar around pussie's neck, under the turtleneck sweater and buckled it so its fit extremely tight. Then she put mathcing pink wrists cuffs on pussie. She ran two chains through the D rings on each side of the dog  collar and hooked each wrist cuff to a chain so that pussie's hands hung on each side of his chest. He couuld move the hands around but could not lower them.

"I bet you thought I would leave your hands free and you could go off and get off tonite" laughed Brit. " Well I just don't want you doing anything nasty like that little girl, so for your own good I have chained your hands, aren't I thoughtful"

"Aunt Brit you really are too nice to pussie" said Amy.

OK we need to get going" Todd said to everyone.

Kathy stepped up to pussie with two blue pills 'open up pussie" she said to her sissy brother-in-law.

pussie could only gasp as he saw the pills. He realized they must be Viagra. He had not had a release in four months and he could only imagine what the result of taking the pills would be.

He tried to keep his pink lipstick lips shut. Kathy merely laughted at the sissy's pathetic protest. She grabbed his prettyfied balls and gave them a hard squeeze. with his hands chained to the side of his boobs, pussie could not protect himself and he could only scream. As soon as he opened his mouth, Kathy shove the two pills in."Now swallow" Kathy said as she continued to squeeze pussie's balls. pussie had no choice.

"ok I think we are ready to have a fun nite, lets go" said Todd.