Saving Grace Part 2

 18/25

This is from my Pink n Prissy Collective series. All captions for this ongoing story are in order on my index page.

Grace watched Terri working away furiously at the touchscreen of the tablet with quiet admiration. The Pink n Prissy Collective's tech guru was like its leader Josie in that she was a certified tomboy, but where Josie was thick and muscular from hours in the gym, Terri was slender, passive and wore spectacles perched on her freckled nose.

“I know the other girls think I try way too hard with this,” Terri said without looking up, “but without me, the Pink n Prissy Collective wouldn't have a website,” she finished typing with a flurry, “or any of its best projects!” She beamed at Grace with satisfaction and looked down the corridor. “Any minute now...”

Both girls watched in silence as a figure pushed through the high-school's double doors dressed in platform heels, white knee-high socks, a knitted mini-skirt and a fitted cardigan.

“Someone's late...” Terri muttered and Grace realised that even though they were the only other people remaining in the corridor after the students had all gone to class, the new arrival did not acknowledge them at all. “Must be still getting used to the dressing process...” Terri nodded profoundly as if realising something. “He'll get used to it.”

“He?” Grace stared hard at the face of the oblivious newcomer. It was heavy with thick and clumsy makeup but she thought she saw the hint of an Adam's apple. Regardless, the outfit and cosmetics combined gloriously to make a creation indistinguishable to the untrained eye from a regular, albeit slightly slutty, female student. “You did this?” She stared in wonder at her friend.

“He did it to himself.” Terri's head was in her screen once more. “With a little help...watch!” They watched as the girl stumbled awkwardly on the platforms over to a locker and fumbled at the combination with long acrylic nails. Finally, the door was open and the girl was staring mesmerised into it. “Six inch flatsreen glued to the back of his locker.” Terri explained. “Programmed to show hypnotic suggestion of the feminising variety. He has seen it five times a day for the past two months – long enough for him to accumulate what he needs for his new wardrobe without questioning why. At end of day yesterday, I pulled the trigger. The video changed to activate his dormant thoughts so that we may witness his debut this fine morning.”

“So this is him now?” Grace marvelled. “He will just go to class? As a girl? Not knowing why?”

“For the most part,” Terri smiled as her, “except when the bell rings... Every time that happens, he will remember who he is and realise what he is doing...just long enough to be humiliated, but not long enough to do anything about it.”

Saving Grace Part 1 (Pink n Prissy Collective)

 8/25

This will be a three part story with the other two parts coming later in the season. It is a continuation of my Pink n Prissy Collective story, which is linked in full on my index page.

“All of us in the Pink n Prissy Collective have our style when it comes to making boys pretty.” Charlotte nodded sagely to Grace, who was still wearing an oversized hoodies and the expression of a frightened mouse. The recently liberated member of the group was having a hard time readjusting to the position of power that came with feminising guys and the other girls had agreed to take turns mentoring their friend. “Josie uses her physical power,” Charlotte continued, “she basically bullies boys into dresses. Terri is a tech wizard – I don't know how she does it, but if a gadget can humiliate a guy, she will find a way. And Cassie...she is devious and scheming. She is manipulative, psychological...but don't tell her I said that...”

Grace smiled timidly. “So, what does that make you? How do you dress up boys?”

“Me?!” Charlotte pressed her glossy pink lips together and stuck out her chest. “I use my charms!” She turned her attention to the figure that had just entered the loft space of the Pink n Prissy house, which Charlotte called her bedroom. The timid creature had smooth skin and heavy eye makeup and was dressed in a short white dress and strappy heels. It hesitated in the doorway before entering the room to make space for its partner, a taller but equally feminine creature wearing a daring black dress and hoop earrings, following behind. Both clutched matching purses awkwardly.

“So, are you going to show us your boobs now?” The first boy asked shyly. “You said you would if I brought a friend.” He beckoned to the blushing boy behind him and then to Grace. “Do we get to see hers too? We better. Putting all this stuff on was so humiliating. We had to get Jim's sister to help us with the makeup,” he nodded to his friend again. “The wigs are hers too.” The boys seemed to huddle together before them, holding their bags like pathetic defensive shields against their embarrassment.

“She sounds like someone I would like to meet!” Charlotte beamed and reached for the bottom of her vest top as if she was about to pull it up. “But...” she let her hands fall to her side, “I don't think you are ready just yet. All our boys have to say the pledge...but it can't just be for me and Grace. All the Collective must see it. That's why we need to go to the mall to get Cassie and then to the library to get Terri.” Both boys blanched at the idea of being paraded around such public places in their current state. Jim glanced at Charlotte and then Grace, his eyes wide, before evidently deciding that seeing two sets of boobs was not worth the inevitable humiliation and started to remove the hoop earrings. Charlotte shook her head sadly. “Fortunately, Josie is right here at home. She just won't be best pleased that a couple of cutie-pies like you two think you can spoil all Jim's sister's hard work without first the others meeting you...and you doing the pledge...and maybe a few pictures!”

Grace gave a small smile as both boys froze in horror and the heavy steps of Josie, the Collective's leader, echoed through the house as she ran up the loft stairs to meet their prey.

A Pink n Prissy Pact Part 4

 

The buttplug was cold. Brent regretted not warming it up as soon as it popped in between his cheeks. But warm it how? He wasn't going to put it in his mouth... Besides the temperature was the least of the indignity the device offered. He was so full he felt like he might burst open from the inside. It was too late now anyway and if he didn't hurry, it was going to be buzzing around inside him, driving him giddy with pain, pleasure and humiliation. The corset was another poor choice. The Pink n Prissy Collective had sent him home with a suitcase of degrading costumes but choosing the one that actively squeezed his middle around the throbbing toy was a mistake. It pressed his caged cock tight to him too, and unlike the plug he hadn't been allowed to remove it for temporary relief so his once manhood felt like it was being relentlessly crushed.

He had to hurry. The girls would be expecting him and waiting with thumbs over phone screens ready to punish him if he was late. He had chosen the glittering corset and bikini bottoms with the fur lining because it was all one piece but pulling on the gloves and stockings and then attaching them to the garter belt had taken time – not to mention bending over to strap on the towering platform heels had been excruciating as his ass hugged its invader ever more tightly. Every moment made him want to crawl up inside himself and never come out, and today was just the first day of his new life. At last, he was satisfied that his appearance was appropriately pathetic that the Pink n Prissy Collective wouldn't punish him by activating his devices remotely using Emi's app, and he lined up his phone with the giant wall mirror in the living room.

“Once a boy...” his voice quivered as the recording started, “...now a Miss.” He couldn't believe he was actually doing this. “Once of gloom...but now of bliss.” He wanted to stop but knew he had no choice. “Once free will...but now a sissy. Now and forever...Pink n Prissy.” He swallowed hard and pressed send.

“It's here! It's here!” Cassie hollered holding her phone aloft. “Brent's first remote pledge is here!” She held her screen in front of her and the rest of the girls joined her in the kitchen of the Pink n Prissy house to watch the recording.

“No fair!” Charlotte exclaimed. “He's at home. Give him a zap and tell him to do the next one in public. Tell him to go to the mall. I want onlookers!”

“Hey, Terri. Can I ask you something?” Grace asked timidly pulling the Collective's tech geek aside as the rest of the girls continued to yell demands to further Brent's humiliation. “When you looked up Emi that time on your tablet. You know the community on OnlyFemmes... There were so many accounts there...”

“There were!” It was Josie, the group's leader who answered. “There are many of us out there who share our particular interest. Some of them go way further than we do... Scarily so... But, you know, each of us has our own method...our own little trick for getting boys like Brent into panties. And, guess what Grace? So will you!” Grace looked up to see that the rest of the Pink n Prissy Collective were now crowded around her. “We promise on all things pink and prissy that you will get your mojo back. We will help you find your little trick! If it's the last thing we do...”

A Pink n Prissy Pact Part 3

 

Emi was good to her word and within a week she had dropped off Brent at the Pink n Prissy Collective house wrapped in a big bow. Literally. Collecting him at the front door from a muscle-bound courier in a tuxedo, the girls were almost surprised not to have to sign for their gift-wrapped package. Once inside, Brett stood in the entrance hall in abject terror wearing a dress not dissimilar in shape to the one they had seen on Matty the week before at Emi's except this one was shimmering satin and had matching mittens that encased Brett's hands. His legs were encased in delicate white silk stockings that fed into high-heeled ballet pumps and his face was painted with exaggerated doll like makeup beneath a long blonde wig that smelled more than a little of resin. Emi had certainly not pulled any punches in feminising the boy.

“That's not the only bow!” Cassie exclaimed gleefully as she lifted the petrified victim's dress to reveal a delicate satin ribbon tied around a mercilessly small cage clasping Brent's genitals. “Hey, look! A gift tag!” She pulled a note that had been attached loosely to the ribbon and turned it over in her hands. “Lot's of Love – Emi x” She read aloud for the other members of the Pink n Prissy Collective. “P.S. He's fitted with all my usual toys but no remote. Just scan the QR to get the app and go wild. Thought you might want to release this one into the wild!”

“Emi has her own app!?” Josie, the Collective's leader whistled. “Terri, why don't we have an app?” She turned to the group's resident tech genius.

“This is going to be the best revenge ever!” Charlotte strode forward, grabbed Brent's hand and began pulling him into the house while Cassie was busy installing Emi's app on her phone. “Hey, Grace, help me welcome our guest.” She nodded to the timid girl swamped in a massive black hoodie. “We have the mother of all pledges to prepare for!” She led the sissyfied boy into the living area and pushed him to his knees. Pulling a brush from under a sofa cushion, she began working it though his hair.

“So, Brett...I bet you thought you had seen the last of us!” Cassie entered the room, her head in her phone. “You thought your sister would protect you forever? Well, last time we saw Kirsten she was wrapped in latex and squealing like a prize pig against the business end of a vibrator!” She looked up from her screen and locked eyes with their gift, whose lip was quivering and looked close to tears. “Now, let's give this thing a test drive, shall we?” She opened a new window on her phone and slowly dragged a finger up the screen. Brett's pink lips dropped open and his eyes closed. A crackle sounded from beneath his dress and a low cry escaped his lips.

“Once a boy...” It was an hour later and Brent was beginning his pledge. Sixty minutes of torture at the hands of five girls armed with Emi's app had put a wrecking ball through any resistance he had still had and he was willing to say or do anything to end it or just even earn a respite. “Now a miss...”  

A Pink n Prissy Pact Part 2

 

“Welcome to my humble abode!” Emi announced proudly, waving her arms theatrically to a lavish apartment that was not remotely humble. The entire Pink n Prissy Collective including Grace, who was still swamped by another oversized hoodie, were squeezed into a single leather sofa and they gazed around in wonder at the vaulted ceilings, life-sized marble statues and moulded walls embossed with unashamed bondage straps and fixings. “It is always a pleasure to welcome fellow artisans of the craft.” She smiled broadly but the girls were no longer looking her way. Instead, their attention had been captured by a meek feminine creature in a flowing black lace dress perched nervously on the corner of a plush seat.

“As you can see, sometimes I bring my work home with me,” Emi chuckled softly. “I do manage almost all of my sissies remotely, but it is good to bring them in from time to time for...recalibration...” She crossed the room and stroked the long brown hair of the frightened figure gently with a latex gloved hand. “This one is Matty. He signed up for my services via OnlyFemmes about a month ago. A volunteer, believe it or not. Lord knows I prefer a bounty, but a shark's gotta eat...and I am a man-eater.” She flashed her teeth. “Grace!” She switched her attention suddenly and the timid girl in the hoodie almost jumped out of her skin. “How are you enjoying Kirsten? You must be a pro at taming her by now? Say, you wanna give dear Matty here a test drive?” Emi strode over to an impossibly large television on six-inch heeled boots and swooped up one of the remotes. The figure that had been identified as Matty visibly wilted at the site of it and he pulled back in his seat, holding his arms behind him and bringing his knees together in a clear posture of retreat. “Give it a go!” Emi tossed the remote into Grace's lap.

“Okay...” Grace stammered looking down at the device. It had just two buttons – one with a tiny but clear image of a cock-cage, the other with a picture of what seemed to be a bejewelled buttplug. Not wanting to upset the terrifying mistress, Grace softly pushed the first button. On cue, Matty gave a high-pitched squeal and lurched in his seat, dragging his towering heels across the wooden floor. Grace stopped immediately and the sissy sat there panting, his stockinged legs pushed firmly together. The second button had a noticeably similar but different effect. Grace pressed this one longer, keen to endear herself to Emi, and Matty's initial jolt of shock appeared to quickly subside into something else. His painted face became foggy and sweat appeared on his brow. Realising she was enjoying her power over the boy, Grace held her thumb down and Matty's short breaths started to hitch irregularly. The rest of the Collective watched on in delight and she slowly but surely brought the sissified boy to orgasm albeit one smothered by his cage. A surreal silence filled the room.

“So, you will get Kirsten's brother for us – Brent?! Josie finally asked.

“Not like this,” Emi shook her head. “I am going out of town next week for some reality TV thing. I am sure you will hear all about that very soon... But don't worry, I will deliver Brent to you with all the toys you need to control him. As my fellow artisans of our noble craft, I trust you to enact your own brand of justice.” She winked and continued to stroke Matty's hair as he softly groaned.

A Pink n Prissy Pact Part 1

 This is a new 4 part story to build on my Pink n Prissy Collective. The rest of this series is on my index page

“I think this one is nearly ready for the pledge!” Charlotte announced folding her arms. The subject of her proclamation was Hunter, who hours earlier had been stuffed into a latex French maid costume and shoved in a closet in the shared area of the Pink n Prissy House. The boy had just been delivering pizza ads and the Collective's tech wizard, Terri had spotted him through the doorbell camera. Never ones to pass up a chance to feminise an unsuspecting boy, the group of girls had grabbed him and pulled him inside. Josie, the Pink n Prissy Collective's leader, as well as their muscle, had held him down while her comrades frantically tore Hunter's clothing away before waxing and painting him into an overwhelmed glossy mess. Hours later, he was their latest trophy, stewing in his new panties, waiting to be inducted into the Pink n Prissy hall of fame.

“Do you think he is broken enough, yet?” Cassie called over. She was the group's innocent faced assassin. As sweet as she looked she had an arsenal of toys for breaking down boys and was also a master, or should we say mistress, manipulator. “I know he's been in there hours, and that rubber dress does look super uncomfortable, but I have ways to make him squeal!” She stared the boy in the face and licked her lips like a kitten.

“No, Cassie. I don't think we need your buttplug right now...” Charlotte shook her head and then grinned broadly at her blushing friend. “Besides, this isn't just Hunter's pledge. This is for Grace too.” She nodded to the fifth member of the Pink n Prissy Collective, who was bundled up in a massive oversized hoodie and looking almost as vulnerable as the boy in the closet. “This is the first one since we got Grace back from that bitch, Kirsten. This is her first steps to recovery!”

“You know what doesn't seem fair?” Cassie sighed. “Emi took care of Kirsten for us – she is now some kind of OnlyFemmes plaything...and even Stephanie is whoring it up every weekend in biker bars. But that dweeb, Brent, Kirsten's brother is the one that started this whole thing...the reason Kirsten did what she did to Grace, and he has got away with it pretty much scott-free. We don't even know where is he? He got away with it and there's nothing we can do...”

“Maybe there is...” Terri smiled, pulling out her tab. She opened an app and angled the screen so that Grace could see it was OnlyFemmes. “This is a community page. It is where we communicate with like minded individuals.” Grace could see she was scrolling through a list of usernames in alphabetical order – Aiko<3, Alice@Law, Anna_ownsJ&R, Artist(Inactive), AzaleaBN, Bunnimacher(Inactive), CassiePnP, CharlottePnP, CLAIREbrody, drlilith... Finally she reached EmiTheShark and opened a DM. “If anyone can find Brent, it is Emi. I would just hate to be in his heels when she does... Now we have pledge to be getting on with...”

“Come on, you!” Commanded Charlotte leading Hunter from the closet by his chin and giving him a firm swat across his latex covered butt with her free hand. She pushed the broken boy to his knees as the other girls crowded around, camera-phones in hand. “Repeat after me, 'Once a boy...'”

Even the Biggest Fish Fears a Shark

9/25

The Pink n Prissy Collective and all their captions (and storyline reboots...) are on my index page.

Grace sat swaddled in the oversized hoodie alone in her room in the house shared by the members of the Pink n Prissy Collective. It had been six months since her friends had rescued her but time as the monstrous Kirsten’s personal plaything still haunted her. Hiding her body behind baggy clothes, she hid inside a shadow of her former self. There was a soft knock on her door and Josie, Charlotte, Terri and Cassie, the rest of the Pink n Prissy Collective, appeared in its frame. Terri, the group’s tech guru, was holding a laptop.

“We’ve got a surprise for you!” Charlotte skipped into the room and the four girls planted themselves on Grace’s bed. The computer screen was open to an app called Mugshot and Charlotte spotted Grace’s confusion. “It’s a new face-to-face video chat app. It launched while you were…away. It has lots of features that I am sure you will get used to over time.” She nodded to Terri who was in the process of setting up a call with a user named Emi_theShark.

“Don’t worry, she’s not scary,” Cassie soothed, “well, I guess she is…just not to us. To us she is sweet! She’s kind of like our idol!” The videocall connected and the laptop screen was filled by the face of an attractive yet powerful looking woman with long bangs framing a pair of startling eyes. Grace noticed with surprise that a shiny latex top rose all the way over her throat.

“Hey, you guys!” Emi greeted them cheerfully. “And I suppose this is Grace?” She sipped a glass of champagne and smiled warmly. “Is she ready for my gift?” Emi appeared to adjust her screen so that the girls could see a wider angle of her room and Grace gasped. Emi was sat at a large extendable dining table with a hole that someone had added between two of the slats. A fully encased black latex head was trapped by the hole – the only visible parts of its occupant a pair of pink painted lips and a set of piercing eyes.

“Kirsten…” Grace whispered in disbelief. “But how?!”

“There’s always a bigger fish, kid!” Emi grinned. “And then there are sharks!” She shared a link across the chat and Terri opened what looked like an OnlyFemmes profile belonging to Emi. The page showed numerous video feeds of different figures in various arrangements of bondage and Terri clicked the newest post at the top. The screen now displayed a wide angle view of Kirsten’s predicament and the girls could see that the rest of her body below the table was also clad in seamless black latex and strapped in place with leather and metal clasps. “I have set you up as my newest subscriber, so let me show you how this works,” Emi explained. “Our ‘big fish’ here is equipped with a selection of my toys that can be activated by the subscribers’ keyboard. ‘N’ is of course nipples. Give it a try!” Grace tentatively pressed the keyboard and watched as her former tormentor gave an uncharacteristic squeal.

“’A’ is Cassie’s favourite,” Terri chided her friend who was known to have a buttplug in her bedside drawer, and pushed the corresponding key. This time Kirsten gave a yelp and jumped up, banging her shoulders on the underside of the table.

“Finally, most of my guests are male,” Emi continued, “so ‘C’ is usually to activate the toy attached to their cock. “But, unintentionally, I think it still works!” Grace pressed the ‘C’ key and within a few seconds, Kirsten’s eyes started to roll back into her latex clad head. When she removed her finger, the eyes returned with a clear film of shame at the degradation she was enduring. “I agree,” Emi nodded, “use that one sparingly.”

“Grace, we are so glad to have you back!” Josie the leader of the Pink n Prissy Collective took her hand. “I know we can’t take back what Kirsten did to you, but I sure hope this helps get your confidence back. There are a lot of boys out there – and we need your help to feminise them all!”

Whatever Happened to the Pink n Prissy Collective? Part 4

 21/25

The rest of my Pink n Prissy captions are all listed on my index page

“It was at that exact moment that Stephanie realised we had set her up. It clicked who Kirsten was and her eyes went wide with horror as everything that had happened to Grace must have been flashing through her head along with whatever might have been about to happen to her. She just gaped at us, knowing we weren't going to come to her rescue, and something visibly broke inside her,” Josie paused for dramatic effect, her eyes locked with Sam's over the campfire.

“That moment was perfect,” Charlotte chimed in. “You could tell she knew she was toast. I enjoyed it almost as much as what came next. She just kind of mentally crumpled. I mean, Kirsten is one scary bitch, but knowing we were throwing her under the bus must have made her feel so helpless. Kirsten told her to strip and she just kind of did it.”

“Stephanie was a hardcore tomboy like me,” Terri continued, “so I get how humiliating it must have been for her to become someone's private Barbie. But when Kirsten pulled out those hideous leggings that make your body look like it was made of liquid metal she seemed almost relieved – like she was expecting a dress or something. It was like she forgot about the massive dildo strapped to Kirsten's waist was a second.”

“It was the heels that were the killer,” Cassie took over. “Obviously, Steph had no experience in shoes like that but they were so high she couldn't even stand. She kind of just toppled forward and put both of her hands on the dresser with her ass sticking in the air like a giant shiny bubblegum.”

“Brent must have got the thrill of his life when Kirsten told him to expose her butt,” Josie snorted. “He was still in that stupid nurse's outfit and shaking like a leaf as he peeled that shiny material slowly over her ass like it was a banana. Stephanie was trying to look back over her shoulder but she was struggling to balance. She saw us sat against the wall and I winked at her.”

“Yeah, Kirsten really thought we were a captive audience,” Charlotte said. “But I was enjoying every moment of it. Kirsten started rubbing Steph's pussy, gently at first then harder and harder, slipping one finger in, then another and another. By the time Kirsten started fucking her with the dildo, Steph was sopping wet.”

“Kirsten moved her to lean on a stool,” Cassie explained, “so Steph had to look right at us while she was getting pounded. With every thrust she made these little squeals like a horny mouse. I can still hear that sound when I close my eyes. After about ten minutes, Steph came hard and Kirsten took the strapon out and looked us dead in the eye. She was actually stroking the dildo as she said if any of us feminised another boy and she found out, we would be next. Then she grabbed Steph by the hair.”

“And that's why the Pink n Prissy Collective has been inactive for four years,” Josie sighed. “None of us want to risk it after hearing that awful howl as Kirsten jammed that giant cock in Stephanie's asshole. At least not until now. With your help, Sam, we're going to take Kirsten down once and for all.”

Whatever Happened to the Pink n Prissy Collective? Part 3

 14/25

This is the latest caption in the Pink n Prissy story. The rest can be found on my index page.

“We didn't realise it at the time but Kirsten was like the OG of sissifying boys at our school.” Josie warmed her hands against the flames of the campfire. She glanced at Sam and shook her head. “She was humiliating the likes of you back when we were still in middle school. If we were a few years older, we would have looked up to her like a God. This is probably why Grace got it so bad. In dressing up Brent, she was pissing in a much bigger and much more experienced dog's yard. And we were banking on the same happening again.”

“When Kirsten came home, everything suddenly got really quiet,” Terri carried on the story. “She must have been only like twenty back then but there was something so commanding in her presence. She just stood in the doorway in her work clothes glaring at us. She had stopped yelling and somehow her not saying anything was even scarier. We were all frozen in place. Even Stephanie hadn't budged from her position bending over Brent to taunt him. Finally, she screamed at us to get upstairs.”

“This is where we took our biggest chance,” Josie said. “The logical thing would have been to run for it. We probably would have got away but if we did that, Stephanie would have escaped too. I made a comment that we should do as she said or she might call the cops and started to lead us up the stairs. Thankfully, Steph followed. We were all so terrified that it wasn't surprising. She was probably on autopilot.”

“Kirsten herded us into a bedroom at the top of the stairs. She waited until Brent sauntered in behind us still dressed in that silly nurse's outfit and locked the door.” Cassie continued the story with fists clenched so tightly that the knuckles turned white. “She was so scary. She didn't even say a word. She just calmly unzipped the back of her work skirt and let it slide down her legs. She looked over her shoulder at us once, took something out of a drawer and fastened the biggest dildo I had ever seen right over the top of her nylons.”

“That thing was enormous,” Charlotte gasped. “It was so veiny and thick. I think you could have played softball with it. I will never forget what happened next. She stood there with her hands on her hips and that big rubber dick pointing at us like it was interrogating us or something. Then she pointed at Brent and asked who had done that to him.”

“Look,” Josie raised her hands defensively, “we're not snitches. We didn't actually say anything. That said, when Kirsten asked that question, not an eye in that room didn't stare straight at Stephanie. We watched her turn white before us and Kirsten just smiled this evil little smile. She looked Stephanie up and down as if appraising her tomboyish appearance and then cracked her knuckles slowly and threateningly. Finally she said, 'I see you like wearing boys' clothes. That's the first thing we are going to change!'

Whatever Happened to the Pink n Prissy Collective? Part 2

 7/25

A bit convenient this one fell of a Friday. The rest of the series is on my linked captions page

“The thing you need to understand about Stephanie is that she loved power,” Charlotte began the story and the rest of the Pink n Prissy hushed quiet. Only the crackle of the campfire accompanied her voice. “Not just the power that comes with dressing up boys either – we all had that, as I suppose you have experienced,” she eyed Sam across the flames. “No, with Steph it was always about being number one – whether it meant making a sissy serve her, or treating us like her slaves...like we were undeserving of her leadership. She totally had coming what we did to her but there was no way she was ever going to leave it there. She was going to come for us and we needed a pre-emptive strike.”

“I reached out to her,” Terri stood and took center stage. “I knew she always respected me a bit more than the others. We both dressed alike – tomboy stuff.” She gestured at her boyish outfit sheepishly. “I told her things weren't going so well with Josie as leader after what...errrm...happened to Grace, and that if she could show she still had 'it', I could get Cassie and Charlotte on board to reinstate her as leader. Basically, an audition to reprove herself. She wasn't thrilled about having to jump through hoops but I think she would have done anything to boss us around again. She took the bait hungrily and all we had to do was set the trap.”

“Terri provided Stephanie with a target and told her she had to go all out so that we would all be reminded of how amazing she was at sissifying boys,” Cassie continued the story from her position next to Terri. “You might have already figured it out, but the boy she picked out for Steph was Brent, Kirsten's younger brother. Stephanie knew what Kirsten did to Grace – she wouldn't shut up about it actually, but she had never actually seen Brent and so when Terri pointed him out, he was just like any other future victim.”

“Stephanie followed Brent home from school with us all tagging along, supposedly to witness her genius,” Charlotte took over. “She had a sports bag full of clothes and makeup and as soon as the kid opened his front door, she bundled him inside.”

“In fairness, she did a pretty good job on him,” Terri said. “And it was actually really satisfying to see that pipsqueak prissified like that. It was his squealing that put Grace in Kirsten's crosshairs after all. She just straight up overpowered him and stuffed him into this kind of frilly nurse outfit complete with headband and heels. The makeup was a bit slapdash but what can you do when they wriggle about like that. When all was said and done, Brent just sat there on his own kitchen floor in a daze. He looked truly pathetic.”

“Steph probably should have realised something was wrong when I walked in,” Josie grinned. “This whole plan was to overthrow me, remember? She sure as shit knew something was wrong when Kirsten got home from work five minutes later and started yelling.”

Season 6 Prologue (Whatever Happened to the Pink n Prissy Collective? Part 1)

 0/25

Surprise!! Not a Flashback Friday but a whole new set of captions. I think I have been a bit mean this time around. Not deliberately but it just ended up that way and a lot of my 'nicer' ideas got pushed back to the next batch because I accidentally made too many.

Today we have the prologue and it is the first part of a story that will run right through the season. It is a continuation of Pink n Prissy series, which you can find on my index of linked captions. I hope you enjoy what's to come...

zoli

The Pink n Prissy Collective huddled around the campfire. Wrapped in a faux-fur lined coat, the girly-girl Cassie cosied up to the leather jacketed tomboy Terri as she flicked through photos of their recent haul of sissies. The last remaining of these prissified boys sat next to them- still unable to speak after his friends had been released from their silence by the antidote to the vocal chord freezing serum. Clad in a short skirt and heels, Sam shivered against the cold and burned with humiliation. He shuddered as Charlotte waved a small pink box at him from across the fire. The tushy tickler was no longer rammed in his backside but the painful aftermath was still being felt. The blonde girl opposite turned her attention to Cassie, shaking the buttplug in its container and winking, receiving a roll of the eyes in response from her fellow Collective member.

“Alright, girls,” Josie stood above them holding a smore. “It has been a few years since we did this.” She smiled sadly. “It had been a few years since we did any of the fun things we have done recently. You see Sammy-kins, as wonderful as it was sissifying you and your friends – good ole' times and all that – we didn't do it just to torture you. There is method to our meanness after all. No, actually we need your help.” Sam looked up at her startled.

“You see, Sam,” Terri took the lead. “We've been dormant for four years and we need your help to fix that. But before we can tell you what we need, we need to tell you why we've been laying low.”

“You'll get your chance to earn back your voice,” Josie continued, “but first you need the facts. You need to know about Stephanie and Kirsten.” She paused to take a bite of marshmallow. “I wasn't always the leader of this merry little group. First there was Stephanie – you think we are mean, well, you should have seen Steph... Okay, long story short, we kicked her out and she did not take it well...”

“Next came Grace,” Charlotte took over, “and sadly, she picked the wrong boy to stuff in a dress. What seemed like a routine sissification went badly wrong and the boy's maniac older sister got involved and...well, let's just say we don't see Grace any more...”

“The point is, Sam,” Cassie looked him solemnly in the eye, “we had two hardcore women gunning for revenge against us and what happened next shaped the last four years of our lives. We brought you here tonight for a campfire story. I know that you didn't come willingly, but I beg that you listen so that you understand what needs to happen next. Listen carefully, because we're going to tell you a tale of betrayal, revenge and sex. And it all begins with a sissy...”

Whatever Happened to Grace? (Flashback Friday)

 Happy Friday everybody!! Today's flashback is for Out of Retirement, which was a three part story from 2016 and can be found here (Part 1, Part 2, Part 3). This is part of my Pink n Prissy Collective series, which can be found in my linked captions index.

“Ohh poor baby. Don't clench. You will only make it worse,” Kirsten cooed and stroked Grace's cheek in the twilight of her bedroom. “Look, you've drooled all over my sheets. You'll want to be more careful with that mouth.” She grabbed her toy firmly by the hair and pulled her up into a deep kiss, her tongue sliding forcefully down Grace's throat before she yanked the girl's head back and used her face to mop the damp patch on the bed covers.

“S-s-sorry,” Grace whimpered. She was silently cursing her firm gym-sculpted body as her firm ass seemed determined to suck on the buttplug tail Kirsten had stuffed inside her like a lollipop. With every swat, with every hair-pull, her body tensed even more and her asscheeks clenched tighter around the perverse object until she thought she might explode. Desperately, she tried to pry her cheeks apart but the leather cuffs securing her wrists only allowed a few inches movement and her futile fumbling just resulted in her hole massaging the steel device. She moaned softly.

“Oh, you are such a little slut,” her mistress grinned. “I knew it from the first time I laid eyes on you. Even in those tomboy clothes, I saw your potential. I could see you were just waiting for someone strong like me to make you their whore. You thought you were cut out for sissifying boys? I wrote the book on sissifying boys. And you know what? I'm even better with girls...”

“S-s-so s-s-sorry,” Grace watched helplessly as the powerful girl took out a keyfob and the cold metal of the buttplug began to pulsate in her backside. “Nooo,” she cried gently and tried to send her mind elsewhere. It only worked in as much as she cast her thoughts back to earlier that day when Kirsten had sent her off to school in that humiliatingly feminine outfit. Everyone knew she was now a pet. How could they not? She had gone from wearing jeans and hoodies to being draped in frilly dresses and cute stockings with bows at the top. Even her former Pink n Prissy Collective sisters looked at her with a mixture of horror and pity, fully aware that one wrong move could lead to them suffering the same fate.

“Hush,” Kristen demanded, “there are much better uses for that tongue.” Grace noticed that she had slipped out of her pyjama pants and was sitting with her legs spread wide at the top her bed. The taste of the older girl's pussy was by now familiar yet it was no less unpleasant. The one plus of having her nose and mouth pressed into the sopping gash was that it momentarily took her mind off the thrumming steel ruining her ass. With one hand on the back of Grace's head pulling her closer, Kirsten stroked the tail through her fingers as if it belonged to a cat. As the pleasure from her licking subject grew more intense, her fondling became erratic until finally, in a moment of ecstasy, she moved both hands to Grace's head and pulled her in as she gushed over her face. Kirsten sighed loudly and began to mop herself slowly with her slave's face.

Eventually, the buttplug stopped throbbing and Grace gasped as it was slid out of her ass with a pop. She knew what was coming next and didn't even bother to open her eyes even as Kirsten's juices dribbled down her lashes. She simply opened her mouth ready as she always did. Obediently, as she always was...

Vice of the Voiceless - Tom

 23/25

This is the final of the four victims of Pink n Prissy's silence serum. Remember there is only enough antidote for three of the 'boys' so you can vote for which sissy you think should remain at the collective's mercy for some further punishment in the comments of today's cap. The other three boy's captions can be found here (Carl, Timothy, Sam) and the rest of the Pink n Prissy Collective story is on my index page.

She would never admit it to her fellow Pink n Prissy Collective members but Josie was beginning to feel a little nervous. As their leader it was necessary to show strength and that's why when she handed the preference cards out to the muted boys, she made sure Tom got hers. She could tell he was the alpha of the group and in breaking him she would be asserting dominance over not only her band of friends but also their rival sex. However, with the deadline fast approaching, her sissy was nowhere in sight.

She was scouring the school grounds for her target. The final bell had long since rang yet there was no sign of Tom. Maybe she should have been more assertive... She knew some of the girls had played active parts in feminising the other boys but she much preferred to see them break alone, desperately debasing themselves for her pleasure, and she had a motto – the tougher the guy, the prissier the sissy. But where was Tom?!

She rounded the side of the school. As a former pupil she still new lots of people at her former hunting grounds but her heart thumped in her chest all the same. Finally, she turned another corner and found a group of boys circled around something next to the wall. Josie tutted on hearing the homophobic slurs they were shouting yet found refuge in the fact she had found what she was looking for.

“Hey! Get out of here!” she yelled at the gang. They stared at her menacingly but began to disperse all the same. Josie made a mental note of their faces, vowing to punish them sometime in the future the only way she knew how. The area now clear, their target was on full show. “My card said I wanted a Bad Bitch,” she smirked, “not a total pussy. Why d'you let them pick on you like that? And I thought you were the alpha...”

The gangly Tom gaped at her despairingly from his position on the concrete ledge, unable to respond. His long stockinged legs dangled beneath him capped with a pair of fierce heels. A red leather jacket draped over tight hotpants and long wavy locks cascaded wildly over his shoulders. Tom might not have been acting like a Bad Bitch but he certainly looked the part. Josie was impressed.

“You got balls dressing like that to school. I would have expected you to slip into something at the last moment. Maybe 'balls' is the wrong word...” Josie gave her prize a satisfied smile but Tom continued to stare nervously past her at the departing bullies, “Come,” she gestured, “the Pink n Prissy Collective is waiting. It's time to vote on whether you deserve your voice back.”

Vice of the Voiceless - Sam

 15/25

This is a new caption from the Pink and Prissy Collective storyline. The rest are on my index page.

I am playing around with different caption designs in an attempt to make them more readable. A few people have said my recent ones have been a bit difficult on the eyes and I want to fix that.

“You got Cassie's, didn't you?” Charlotte grinned at the sheepish looking Sam. She had waiting for him at the bus stop home from school and finally she had been rewarded with the terrified, silent student. “Let me see!” She snatched the notes her prey had instinctively reached for and read her fellow Pink n Prissy member's request aloud. “I want my sissy to be cute, sassy and fashionable....ha! What rubbish!?” She balled up the paper and threw it away. “Listen, I'm going to give you a little quid pro quo because Cassie is my best friend and, well, if she's happy, you might stand a chance of getting your whiny little voice back. You want that right?”

Sam nodded feebly.

“Good! Look, I'm not saying clothes don't matter, because they obviously do, but if you really want to get Cassie's heart racing and by proxy your tongue wagging again, you're going to need to step it up a notch.” Charlotte produced a small pink box from her purse. This should do it.” Sam gave her a pleading look as he took the gift, swallowing hard as he read the logo on the box, 'The Tushy Tickler.' “Don't worry,” Charlotte smiled widely, “there's lube in there too!”

The next day, Charlotte and her Pink n Prissy Collective co-member, Terri, were watching the bus stop once again from the privacy of a large tree. There was a solitary figure waiting on the bench, an apparent girl dressed stylishly in a white top and cardigan with a short skirt over a pair of glossy nylons, all pulled together with a large chequered scarf.

“Are you sure that's her, errrr...him?” Terri nudged Charlotte. “He looks almost too good. The other boys might be in trouble.”

“Of course it is,” Charlotte giggled, “no real girl would ever sit with her legs wide like that. Though I must say, they do look sensational. Anyway, there's one way to know for sure.” She pulled a small black keyfob from her pocket.”

Terri pursed her lips in excitement. “You know Cassie's going to lose it with you one day if you don't stop teasing her about that buttplug. Do you believe her about it being for torturing a boy?

“Does it matter?”

“I guess not.” Terri replied. “Hey, I wonder if Sammykins here followed through on your suggestion.” Charlotte gave her a wink and pressed the keyfob. Both girls had to stifle their laughter as the dolled up boy's formerly spread knees clenched together as he leaned his body forward in a first unearthly groan.

 

Vice of the Voiceless - Timothy

 8/25

Captioning 101 - check the picture is big enough before deciding to use it. Sorry if this one is hard to read.

It is a continuation of the Pink n Prissy story. The rest are on my index page.

Cassie shouldn't have been surprised when Timothy turned up at her door – she had asked her younger sister to slip him an invitation in class after all – but still, seeing him standing there silently looking down at his feet brought her an unexpected feeling of joy. He had come because he needed her help. He had come because he had no other options. He couldn't say so since the serum Josie had given him had paralysed his vocal chords but the message was loud and clear and could be described by a single word that hovered between the high school boy and the Pink n Prissy member – Desperation.

Cassie held out her palm and Timothy placed his card in it and slumped past her into the house. She didn't need to look at it to know Terri's preferences – FRILLY, SWEET AND GOOD ENOUGH TO EAT. Her fellow collective member may be the tomboyish computer nerd of the group but when it came to how she liked her sissies, there was no ribbon, petticoat or lace to be spared.

“This way,” she led her despairing captive up the stairs and into her room. She pushed through another door, pulling the boy by his hand and Timothy's jaw dropped as he realised he was in a walk in closet surrounded by rails of pink outfits and prissy dresses. “Don't worry, you're not the first boy to react to my torture chamber like that – won't be the last either. They usually protest a bit more though. I can't decide if I miss it. Oh, well, by the time we're through, you'll be dying on the inside. At least you will be if you ever want to speak again...”

And so Timothy's transformation began. Cassie took painstaking care over every detail, drawing out every moment of her prey's humiliation – carefully folding his clothes as he removed them and covering his naked body in hair removal cream. After giggling in mock embarrassment when he became aroused by her touch, she pulled a pair of layered panties up his legs followed by a pair of sheer stockings. Breast forms inside a lacy bra were next and then a carefully sized flowery dress was chosen and pulled over his head. By this stage, Timothy's erection was well and truly gone and terror gripped his features as Cassie painted them liberally with her cosmetics A few finishing touches; a nylon cap to contain his hair under the long feminine wig, modest white heels, delicate wrist-length gloves, and after two hours of hell the high-school boy was a sight to be beholden.

“You look delicious!” Cassie exclaimed to Timothy, who was unable to meet her proud gaze. “I am almost sad you look so good. You will get the antidote for sure. I would love to keep you like this as my little pet.” She continued to look at him thoughtfully. “You're probably wondering why I have so many outfits than fit Terri's preferences,” she looked around her at the wall-to-wall clothing and blushed a little. “Oh whatever, who are you going to tell...” she grinned at Timothy and pulled back a rail of dresses on their hangers to reveal the wall behind. It held a collection of photographs arranged lovingly, not trophies of prissy sissies she had created but something much more dear. She reached to adjust her favourite picture of Terri and beamed.

Vice of the Voiceless - Carl

 2/25

So the Pink n Prissy Collective have four poor guys with frozen vocal chords and only three vials of antidote. What a predicament!? Over this season we will see how each unfortunate boy tries to earn back their right to speak and in a cruel twist there will be a 'choose your own adventure' style vote to pick which sissy has to go that one step further for their release. First up is Carl...

The story so far is of course listed on my index, albeit quite far down.

Carl pulled the crumpled card from his hoody pocket and pretended to study the words he knew by heart. There was a futile hope every time he stared at it, something different would be there. Something less humiliating. Something other than Charlotte's dream sissy. - 'I WANT A MIAMI BARBIE – SUNKISSED, SWEET AND SEXY. BLONDE AND BLISSFULLY PINK – CHARLIE X' - He stuffed the note back in his pocket and pulled the black hood as far as it would go to hide his face. Crowds of customers milled around him in the department store and he was determined to hold onto some male dignity for as long as possible. All the careful preparation – all the plucking, scraping and painting of skin and hair was still covered by the boyish exterior of his hoody and jeans.

It had been five days since Carl had last spoken and he was getting desperate. An initial hope the serum that had frozen his vocal chords would fade after a day or two had now lingered and died along with the idea he might come out of this without having to debase himself to the four college girls that called themselves the Pink n Prissy Collective.

He had managed to get a surprising lot done without alerting anyone to his feminine motivations. The internet had provided purchasing opportunity and instruction for makeup, hair and nail extensions and waxing strips and when he had visited a spray-tanning booth, he hadn't even been the only guy there. Clothes ended up being the roadblock. The sizes were an alien language to him and with time running out before the deadline set by the girls, he couldn't afford to get something that didn't fit and he wouldn't have dared ask for help even if he weren't vocally challenged.

Carl approached the checkout with a pink tennis dress draped over his arm and a pair of strappy wedge sandals clasped between his acrylic tipped fingers. A flash of panic ripped through him as he noticed the girl serving and realised it was his cousin, Becca. He would have to remove his hood to make the purchase and even beneath the layers of glossy cosmetics and synthetic hair, she would surely he recognise him and his humiliation would extend far beyond the evening deadline of dolling himself to get his voice back. Making a on-the-spot decision, he grabbed a tote bag from a rack and dashed for the changing rooms.

In the privacy of the booth, Carl pulled off his jeans and hoody and his mounds of blonde hair flopped over his face. He tugged the pink dress over his smooth body and sighed with relief that he had chosen the right size as he stuffed his own clothes into the tote. Now in his final form – sunbleached skin, pouting pink lips and cute pink outfit- he gathered the bag and half-sprinted half-stumbled on the wedges to the store exit.

“Hey, you! Hey, Miss! Come back here!” He glanced back in horror to see a security guard chasing him from the shop. “Stop thief!” Another gave pursuit and crowds of shoppers stopped to stare. Realising he was surrounded, Carl stopped, wide-eyed with fear and the words 'I can explain' running through his mind over and over. But, of course, he couldn't..