Panty Raid Gone Awry

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The only time that Chantelle was allowed to stop work was at 12pm, when she had 30 minutes to have a salad (with a protein of her choice), a protein shake and some more vitamins and hormones. After that she had to finish cleaning before returning to the kitchen and cooking herself a low calorie meal from her approved recipe list, as well as her final handful of pills.

It used to be the case that Heather, May and Skylar would follow Chantelle, still thinking of himself as "Charles", in order to make sure she was working properly, punishing any slacking with a kick to the balls or a harsh smack from a riding crop. Luckily, Chantelle had been on her best behaviour for close to a month now. This allowed the girls to focus on themselves, Heather and May had actually started dating each other and usually shared a bedroom these days, while Skylar spent most of her time with her new boyfriend who, from the state of the lingerie that Chantelle hand washed every weekend, was sexually insatiable.

That's not to say that Chantelle still didn't hate being the sorority's sissy slave but she now knew that there was no escape through defiance, but maybe through obedience she would eventually be released from her pink prison. With this coming weekend, "Pink Prison" definitely had a double meaning as the girls had promised Chantelle time out of her chastity cage if she managed an entire month without any disobedient outbursts. As such, Chantelle had smiled and curtsied at every command, acting as quickly, efficiently and effeminately as possible to complete them.

------

"6 months ago, these three lovely sisters of ours caught an intruder," Amber, the sorority president, said into a microphone with a smile, addressing the assembled membership in the basement meeting room. She was stood on the raised dais looking out at over 60 girls from across campus (as well as a few of the staff alumni who had helped them), joining her on the dais were Heather, May and Skylar, who were currently taking a bow as the crowd cheered and clapped for them.

"At first, they were naturally outraged by the presence of an uninvited guy within the walls of Zeta Tau and we were ready to kick him out into campus in handcuffs and panties." Amber continued. "However, these angels pointed out that, maybe, that's what he wanted. His little dick got so hard when we put him in panties it could only mean one thing. He wasn't a man, was he?"

"NO!" Came the crowd's response.

Amber laughed and then asked in mock confusion, "So, what was he?"

"A SISSY!" The crowd shouted back in excitement.

"Yes, and as the kind and charitable ladies that we are, we decided to help that sissy become the best girl she could be."

The crowd cheered at that again and it took a moment for Amber to bring silence again.

"It took time and a firm hand but I think Chantelle has finally learned her place. When her training started, it was agreed that if she behaved perfectly for an entire month she would be rewarded. No one has reported any disobedience or feigned masculinity from our wonderful maid this month, so I think it's time for that reward. Does anyone disagree?"

There was no response from the crowd, so Amber continued as Skylar sauntered over to the side of the dais, "Ladies, please welcome our wonderful, obedient, slutty sissy, CHANTELLE!"

The crowd broke into applause and cheers as Chantelle was brought out from behind a curtain. She was led by the leash that was in Skylar's hand and attached to a white leather collar that was wrapped around her neck, in silver letters on either side of the leash's D ring it said "sissy" and "bride" and that's what she was.

Heather had explained earlier that as a reward for being the perfect sissy, Chantelle would be allowed out of her cage and was going to lose her virginity tonight, to a sorority sister of her choosing and there was no better outfit for a virgin sissy than a wedding dress. Or rather... the pornographic equivalent of a wedding dress.

She was wearing sparkling silver 6 inch platform heels with a thin ankle strap, white fishnet stockings, the garter straps of which were attached to her excruciatingly tight satin overbust corset, the padded cups squeezing her hormone enhanced tits delightfully. She wore no panties, and her tiny pink cage hung free for all to see. In her lace-gloved hands, she held a bouquet of pink roses that matched her pearlescent lipstick and nails.

Her makeup was immaculate as always, her ever so generous mistresses had tutored her specially for her current look: soft pink lipstick, pink and purple eyeshadow, winged eyeliner, perfect contour and fake eyelashes, heavy with thick mascara. Her blonde hair was styled into an intricate, braided bun with her veil trailing down her back to just below her bare ass. The only jewellery she wore was a tiara on top of her long tresses and a pair of chandelier earrings.

Amber lifted her hand to the crowd with a dramatic flourish to show she was holding a tiny key. She then swept towards Chantelle and bent down, unlocking her cage and removing it with slow certainty to reveal the soft, hairless two inches between the sissy's legs.

"Freedom from your cage is only part one of your prize," Amber said, speaking directly to Chantelle but loud enough for everyone to hear, "for part two, you're going to lose your virginity to a sister of your choosing."

The crowd cheered as Chantelle froze in stunned silence. She had hoped to get out of her cage but this was above and beyond her wildest dreams.

"So, Charles," Amber mocked, using his male name for the first time in 6 months, "who's it gonna be?" She asked as she gestured around the room.

Chantelle looked around the room, a million thoughts going through her head but there was one girl she'd thought about repeatedly over her imprisonment...

"Lucy..." she practically whispered.

"Oooh, Lucy" Amber repeated into her mic, "looks like our sissy likes sporty girls, must be that stamina she's after." She added the last comment with a wink to Lucy who was making her way towards the stage.

For her part, Lucy must have expected to be picked to take Chantelle's virginity. She had her hair tied up in a tight, high ponytail and her makeup was more severe than her usual look with pink eyeshadow and red lips. However, her body was covered by a long, black, leather trench coat but Chantelle could see her pink snakeskin boots peaking out with each step.

Lucy ascended the steps onto the stage and stood across from Chantelle with broad smile and an evil glint in her eyes. She took the sissy's leash from Skylar and whispered to Chantelle, "I knew you would pick me, so I chose my outfit just for you."

Chantelle was too busy staring into Lucy's beautiful face that she almost missed when Amber announced, "Lucy, you may now kiss the bride."

Lucy placed one delicate hand on the back of Chantelle's head and pulled her into a deep kiss. The poor sissy couldn't help moaning in near ecstasy when Lucy's other hand took her tiny, rock hard cock in hand and started to stroke it, allowing Lucy to slip her tongue into her sissy mouth.

6 months without orgasms, locked in a tiny pink cage, constantly surrounded by beautiful women and dressed in sexy lingerie. All of it came crashing down in that moment as Lucy's probing tongue and soft hands sent Chantelle over the edge. She broke off the kiss and moaned loudly as she came, practically humping Lucy's hand to milk every last drop from her sissy clit.

"Oh dear," Lucy said kindly and placed another gentle kiss upon the sissy's lips, "don't worry Chantelle, we can still have lots of fun. Why don't you get down and clean that up first though."

This wasn't the first time Chantelle had been ordered to clean up cum, though on the previous occasions it had not been her own. The sorority sisters had taken great pleasure in making their sissy drink out of condoms or clean their freshly fucked pussies with her tongue. On those occasions, the cum had been thick, warm and sweet yet salty but the orgasm that Chantelle now had to clean up was thin, watery and barely had any taste.

On her knees, Chantelle licked her cum off the stage as the audience of sorority girls whistled, laughed and cheered. There were a few droplets on Lucy's boots and Chantelle began eagerly licking the pink faux leather. As the sissy lick her boots clean, Lucy slowly and deliberately unbuttoned her coat and let it fall to the floor. Chantelle kept licking Lucy's boots but looked up in curiosity as to what she had been hiding under the coat. She could not make out most of her outfit though, as her view was blocked... by the BIGGEST BBC strapon she had ever seen.

The strapon was over 13 inches long and nearly as wide as Chantelle's wrist and the kneeling sissy could not help drooling at the sight of it as it reached down to Lucy's knees.

"This is what you've been waiting for," Skylar whispered into Chantelle's ear, "a chance to lose your virginity and have sex with Lucy. Just do what comes naturally to you and she'll take care of the rest."

"What do you think Chantelle?" Lucy asked seductively, "don't I look beautiful?"

"Yes, Mistress," Chantelle responded without hesitation. It was true, in the black latex bralette and high waisted booty shorts, Lucy looked divine, regardless of the cock that dangled from the leather harness that she wore.

"Why don't you give me a kiss, then?" She asked, raising the big, black cock to Chantelle's lips. The sissy couldn't help it, placing a gentle kiss on the tip of the cock as she stared up at Mistress Lucy's beautiful, smiling face and, with the slightest pressure on the back of her head (she wasn't even sure which of the girls had pushed her), her lips parted and she began taking the cock deeper into her mouth.

"C'mon Chantelle," Lucy admonished as she weaved her hands into Chantelle's hair, "you can do better than that. Zeta Tau didn't spend months training you to give bad head."

She was right, of course. Heather, May and Skylar had started Chantelle's dildo training on day one, teaching her the art of stroking, sucking and deepthroating but her asshole cherry was yet to be popped other than her buttplugs. Doing as she had been trained, Chantelle readjusted her position on her knees and relaxed her throat, allowing Lucy to slide more and more of the monster cock into her sissy throat. It took some doing but, on the 4th attempt, Chantelle managed to touch her nose to Lucy's crotch, the dildo's large balls resting on her chin.

With that accomplished, Chantelle pulled back until only the head of Lucy's cock remained in her mouth and proceeded to rub the full length of the saliva covered cock. Lucy then told her sissy bride to assume a position on all fours, which Chantelle immediately did, facing the audience of cheering women. She then positioned herself behind Chantelle, one hand on her her hormone enhanced hips and the other guiding her giant phallus to its target.

Chantelle gritted her teeth as Lucy's strapon began stretching her sissy-pussy. The BBC was only slightly wider than the largest of the training plugs that Heather, May and Skylar had been sliding into Chantelle's ass. After a moment's resistance the head of the cock pushed into Chantelle's anus with a *pop*.

"Congratulations Chantelle," Amber announced on the microphone, as Chantelle's three trainers let off handheld confetti cannons showering everyone with glittery pink confetti, "your virginity is a thing of the past and, from the sounds of it, being a full blown sissy slut may be in your near future."

Amber was right on that point, Lucy was still rocking her hips back and forth, thrusting more and more of the cock into Chantelle's ass with each buck of her hips. In response to her anal invader, Chantelle was moaning like a slutty pornstar her eyes practically rolling back into her skull.

True to her athletic appearance and reputation, Lucy had the stamina of an Olympian and once she got into a rhythm she just kept going and going and going, fucking Chantelle in doggystyle to start, flipping her into missionary, before finishing reverse cowgirl. Chantelle had probably dribbled a dozen little cum loads onto the floor or her own body during the 2 hour fuck marathon that Lucy had taken her on.

When Lucy finally pushed Chantelle off her cock, the sissy's legs were too weak to support her and she collapsed onto the stage, into her own pool of cum. She was on the verge of passing out from exhaustion when Amber stood over her again, looking down with a cruel smile on her face.

"I think you enjoyed that, didn't you sissy?" She asked and Chantelle nodded weakly, "in fact, I don't think you'll ever want to touch your clit again. Not that you'll get the chance."

Heather, May and Skylar then descended on Chantelle. Heather stuffed her sissy clit back into her tiny, pink chastity cage and locked it shut, she also pushed Chantelle's largest plug into her ass. May shoved a cock shaped gag between Chantelle's lips and buckled it behind her head, followed by a padded leather blindfold, leaving her in darkness. Chantelle was then flipped onto her front and her hands pulled behind her and forced into some sort of restraint sleeve, it didn't take much to realise that it was Skylar's armbinder that she regularly used to restrain Chantelle.

Being too exhausted to move, Chantelle was actually relieved when the girls picked her up and laid her down on something soft, she wasn't sure what it was but it was padded. She was in the foetal position but when she tried to stretch her legs out, she found she couldn't, they hit a wall of some sort, as did her head when she tried to lift it and her arms when she pushed them out behind her.

"I think she's putting two and two together," came Skylar's mocking voice, "you're in a box, a steamer trunk to be precise, don't worry we got it in pink just for you. You see, my boyfriend is super excited to meet you but we can't exactly have you walking across the campus dressed like that."

"Say goodbye to our sissy, Zeta Tau. She's going to be leaving us for a long time." Chantelle could hear Amber say to the crowd as her heart started to race in panic.

"GOODBYE CHANTELLE," the crowd shouted as the trunk's lid was slammed shut and locked, muting Chantelle's muffled screams.

"Time for bed I think," Skylar said with an exaggerated fake yawn, "we'll have to be up early to take her over."

The basement slowly emptied, leaving the trunk on the stage, rattling ever so slightly as they shut the light off.

------

Chantelle woke up the next morning still restrained surrounded by darkness. The only hint that she received that it was morning is that she could hear voices talking and music outside of the trunk and she was tipped slightly on its side and was jostling, as if she was being carried on some sort of dolly.

She couldn't make out what the voices were saying but she thought that one of them could be Skylar, who was currently talking to someone with a much lower voice, definitely a guy... her boyfriend, maybe? Chantelle honestly had no idea but something the guy said elicited comments from two new voices that were either side of the trunk, making it clear that it was May and Heather who had been carrying her around on the dolly.

Chantelle then heard the locks being clicked open and she guessed that the trunk had been opened as she could feel a slight breeze. A pair of hands reached around her head and removed the blindfold so that her world was suddenly filled with light.

Standing above her, Chantelle could she the cocky smiling faces of Skylar and, shockingly, DeShawn, the Alpha Sigma Phi frat president.

"Sweetie, meet Chantelle," Skylar said, rubbing DeShawn's broad chest, "Chantelle, I'm sure you've met my boyfriend, DeShawn, haven't you? At the very least you've tasted him more than a few times." Everyone laughed at that, except Chantelle, who was still gagged and thinking about those all condoms that Skylar had made her lick clean over the past months.

"So, here's the deal, baby," Skylar smiled at DeShawn as if there was nothing unusual about the context of the trunk, "you keep the panty raids away from Zeta Tau, and you boys get to keep little Chantelle here as your own house maid."

"What's the catch?" DeShawn smiled back, grabbing a handful of Skylar's ass, as Chantelle began to seriously panic. Being a maid for a houseful of hot sorority girls was one thing, but horny frat bros was entirely different.

"No catch," Skylar responded with a soft kiss, "she's fully trained and very obedient. She comes with a fully stocked, slutty wardrobe," she gestured to something outside of the trunk that Chantelle couldn't see, "she's got no record on file with the school seen as she officially dropped out a couple of months back. Y'know her father wrote some really rude letters to the school asking why he was getting a dismissal notice about a girl called Chantelle when he had a 'son' called 'Charles'. He started calling and texting her nonstop. Luckily it only took a few paragraphs explaining Chantelle's new outlook to explain his mistake, that and a few photos of our little maid during her training."

Chantelle, no, Charles suddenly had a sliver of hope, his father knew what was happening, he'd call the cops, he'd do something, anything to help his son escape.

Clearly, DeShawn had the same thought process, "what'd the old man say?" He asked.

Heather provided an answer, waving her hand dismissively as she leant upon the trunk's open lid, "oh, there was some long rant, lots of swearing and a liberal use of the word faggot sprinkled throughout. A masterpiece of bigotry, really."

May picked up where her girlfriend left off with a chuckle, "we responded with a video of Chantelle bouncing on her dildo. Daddy hasn't sent any response to that but all of Chantelle's family have blocked her number and social media."

"Wow, you girls are thorough," DeShawn responded with an impressed whistle. "Looks like someone didn't like your story," he added looking down at Chantelle, who now had tears streaking down her face.

"Who cares?" May shrugged, clearly meaning it.

Skylar then leant over the box and grabbed Chantelle's face so that she was looking straight at her.

"Let me break it down so your dumb, bimbo brain can process it." She said, emphasising every word in an overly sweet singsong voice. "Your family don't want you. You have no money. No ID. No options. You are the slutty, cock-sucking, anal-loving, empty-headed, hormone-filled, chastity-wearing sissy maid of the Alpha Sigma Phi fraternity."

Her voice became very harsh at her final three words: "is that understood?"

She unbuckled Chantelle's gag and raised an eyebrow in anticipation of a response.

Chantelle's brain was wrecked, the girls had ruined her, they had truly thought of everything. There was no way out. So she spoke the two words that would seal her fate forever.

"Yes Mistress."

------

The girls headed back to the Zeta Tau house as the frat guys carried the 2 trunks containing their new maid and all her clothes bad toys into their house. Undoubtedly, they'd soon "welcome" Chantelle to frat in a variety of ways.

DeShawn had certainty made an interesting counter offer that they had to take back to Amber. Instead of keeping all the panty raids away from Zeta Tau, the frat would direct all the short, scrawny pledges their way, with a heads up for the Zetas, of course. Heather, May and Skylar thought it was an excellent idea, after all, the Zeta Tau house wasn't gonna clean itself and Chantelle could definitely do with some feminine company.

As they walked back across campus, the girls were already making a list of the preparations for next year's pledge week.

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MCJOHN11708MCJOHN117088 months ago

The story was amazing, up until the point of the sorority selling off the sissy to the fraternity. Disapointing. Hoped they'd keep the sissy around, maybe even pawn her off to one of the sisters as a permanent bitch bride. Oh well.

3/5 - 2/5 can't quite decide.

XamdXamdabout 1 year ago

It was ok. It seemed a little rushed in the transition phase, the guy barely put up a fight. And then it ended too soon, you know what we wanted...

AnonymousAnonymousabout 1 year ago

This reminded me of Sorority Boys ch.1 Panty raid by wittlesissybaby. That one has diapers but love both stories.

AnonymousAnonymousabout 1 year ago

This reminded me of Sorority Boys ch.1 Panty raid by wittlesissybaby. That one has diapers but love both stories.

AnonymousAnonymousabout 1 year ago

Love the story. However the transition from being caught to doing chores was a little forced. Maybe you could fill in more on the training done to making the sissy, instead of sprinkles throughout the story. Thanks and keep writing.

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