Author's Note: This is sort of a parallel story to my most recent tale. With a bit of a tie in at the end. Perhaps a bit of a slow start but it picks up pace quickly. Hope I was able to entertain you both times!


Freddy still didn't understand how it all went so terribly wrong. The fantastically rich haul was only intended to be deposited in the little cartel owned small town bank for a few hours. But a change at the last moment nescessitated added security be sent in for the week long extended stay. Thinking only of his 3 million, possibly augmented by some opportunistic chicanery Freddy gave the go order for the bank takedown. His AR15 was down and his hands were up 3 seconds later. His amateur hour crew quickly followed suit.

Freddy had sold the family business and assets and quickly squandered his generous inheritance. He was broke and heavily in debt. Some of his less savory associates had made him aware of the bank heist of the century which would solve his problems. In spite of the almost comedic nature of the heist it was all still taken very seriously and it cost him the remainder of his hidden assets to avoid an extremely lengthy sentence. This included a very substantial payoff to the judge and a few other pertinent officials. To placate local outrage and mislead his substantial quota of outside enemies including gambling creditors, cartel crime lords and his former partners and their associates that he had testified against, his 30 year sentence was still substantial. But it would be changed to an 18 month sentence and he would be released after only 3 mos. The fix was in though it did include the proviso that the term would be served at a new privately run experiemental facility. But Freddy's attorney had assured him it would be the optimum of a modern amenities friendly facility and not unlike a relaxing country club.

Upon first arrival the facility seemed not unlike Carruthers, his attorney described. But the large number of female staff and guards and their haughty disdainful demeanor was a bit unsettling. Still his room was a large and comfortable with a private bath, television and an overstocked Frigidaire. But it all began to unravel after Judge Magruder had received Freddy's pricey inducement. Two tall guardesses in tight red and black latex respectively, entered his room at midnight and quickly confiscated his large collection of print porn even while he was naked and masturbating to a particularly slutty centerfold. They said nothing but merely smirked and looked down at him with loathing disdain. His cock remained on very stiff and shiney display . Well lubed with drooling pre cum.The hot smirking redhead in red latex said; "Your induction period ended after Midnight, Miister Parker. Masturbation is no longer permitted without written authorization. " They took photos of naked Freddy with his stiff cock in hand then walked out of the room with their spike heel boots clicking on the hardwood floor. Freddy watched their toned bubble bottoms undulating in tight latex and his hand, with a mind of its own raced at 90 along his shiney wet cock shooting copious salvo's of steamy jizz high in the air just as they exited.

Next morning a buff, bearded male guard entered and announced Freddy would be assigned a job in the mail room pending approval and his first assignment will be to deliver a package to Charlene, the wardresse's secretary and administrative assistant. Freddy was 27, dark brown hair and good looking though not exactly trim and fit his love of overindulgence and disdain for working out was only in evidence in his less than flat belly and somewhat prominent posterior. He was wearing a loose fitting light blue shirt over light blue pajama botton like pants and slip-on sandals. standard prison attire when he entered wardress Cordelia's office and met Charlene. She stood up and walked around her desk smiling mischievously. Her hair is golden blonde and her long curls fall down around her shoulders. She licks her full red glossed lips as though she is approaching prey. Curvy in tght fitting short black skirt, translucent low denier flesh toned hosiery attached with black garter belts, black high heels and form fitting pristine white blouse.

"Hello Freddy, we've been anticipating your arrival" Now get undressed!" Surprised, he hesitates. "Do as I say! Now! I need only press an alarm button or call out and all sorts of nasty things will come down on you!" " But I was given to understand that we had..." She laughs "A deal? You can speak to Cordelia about that later. Now get out of those silly clothes!" Freddy did as he was told . His cock payed tribute to Charlenes charms. Elongating and swaying in front of her. She smirked and walked behind him. She prods and pinches his prominent posterior and giggles. "Let yourself go a bit, huh Freddy?" You're likely to make some interesting new friends here with this caboose!" She macks his bottom sharply and smiles when he yelps." She reaches under him and painfully pulls back his balls and spanks them sharply causing him to howl in agony and surprise. "You were found to be masturbating after midnight, Freddy. You naughty boy! Didnt you read your induction instructions?" She relinquishes his balls, for the moment but reaches around him to pinch and twist his nipples most painfully. She laughs as he winces and groans. She moves back in front smacking his tumescent cock until it droops then grasping his balls and now semi soft cock and stretches them away from his body. She continues to pull and twist while Freddy groans and tries to form a sentence."On your hands and knees,now, Freddy." He quickly complies withoit thinking. She circles slowly around him . Her high heels click clacking on the wood floor. She prods and pokes his dangling balls and cock and makes painful indentions in his fleshy ass cheeks with her sharp heels.

"I thought we had a deal!" Freddy manages to groan out. "Well, you did. But you signed all that away when you delegated total authority to us. Perhaps you should read what you sign next time, Freddy!" (Giggle) "But... but.. I..." She pulls his head up by his hair "Shut the fuck up and suck my spike! Better make it nice and wet, too!" ( Giggle) She raises a shapely well toned leg and makes Freddy suck her 4 inch spike. When its shiney wet she walks behind him and slowly but forcefully inserts the big spike deep into Freddy's anus. He yelps from the brief but sharp agony of insertion and groans as she pumps it slow and deep in his tight asshole giggling all the while. She leaves Freddy with a raw swollen anus and seats herself on a chair in front of him. She isn't wearing panties and the propinquity of her wet, shiney snatch causes Freddy's dangling cock to drool pooling pre cum beneath him. She spreads her legs and extends her spikey shoes to Freddy's drooling lips. Making him tongue each shoe to a high shine. She giggles at his obsequious servility and his hot bulgey eyes staring at her twat. She makes him sit spread eagle in front of her. His hands on the fllor at his sides."Want to see my boobs, Freddy?" She unbuttons her blouse and unfastens her bra, spilling out her big pointy melons. Freddy's sore, swollen anus causes him to fidget uncomfortably on the hard floor but his cock instantly rises in tribute to her bodacious display as she fondles her bountiful boobs and teases and pinches her big pink nipples." OK Freddy, I know you want to. So go ahead and jerk it off for me."

Freddy's hand immediately began tugging and yanking his very erect cock Her sex scent is intoxicating and her hot wet snatch glistens from the ribbon of sunlight that plays across it . Freddy's loose fist is running at 90 up and down his slick shiney cock and he moans with pleasure as his throbbing cock erupts and geysers hot jizz high in the air. Charlene giggles like a nasty precocious little girl as his hot milk arches high and then splashes down across his chest and belly. She kicks off her shoes and straddles above him holding her arms akimbo. "Lie back, Freddy!" He leans back on his elbows and she scoops up great gobs sticky jizz with her nylonned feet and feeds them to Freddy with her stinky toes. Pushing them insistently in his mouth even as he tries to turn away. She laughs as she makes him lick away the last sticky gob.

"I guess you still don't remember me do you Freddy? I was skinny and nerdy and looked a lot different back then. A girl doesn't forget her first Freddy or how you ditched me and treated me so rotten and made me feel so hideous and worthless. Freddy's jaw drops; "Charly?" " Its Charlene now Freddy! Remember it! I'm an entirely different person now! You may remember my mother, your fathers former business partner until you took over control of her shares and sold off our property. Our family had owned that land for nearly 200 years!" Freddy is stunned and speechless as Charlene cooly buttons back up and slips her shoes back on. She thought you should be welcomed here with a good hard spanking. I suppose I embellished on that a bit but I concur. Charlene presses a button under the desk and two rough, muscular male guards immediately rush in. "He got naked and was masturbating in front of me!" They immediately pull Freddy to his feet and drag him away.

Freddy is ass up and strapped down over a a leather topped trestle. "Wait! You can't do this! There were certain arrangements! This is medieval! " The crude blackbearded guard laughs as he and his hairy buff, black haired partner each select thick ,leather prison straps off the wall. "Yeah, I guess it is kinda medieval ain't it JW?" They both wail ferociously into Freddy's fleshy out thrusted ass all the while rudely berating him for dishonoring Charlene and being such a perverted yankee.His loud howls and screams only encourage the sadistic guards to whip him harder and no one can hear him in the soundproof punishment room. They savage every inch of his soft, sedentary ass thoroughly enjoying their exertions and being pleasured by his agony. Finally stopping the bearded guard smiles when he notices Freddy's red, swollen anus. "You a queer too, boy? Looks like you done had some rear action." The rough guard rudely shoes a fat dirty finger deep in Freddy's raw anus and he yelps loudly. The guard laughs and thrusts in another eliciting an even louder response. His grinning partner dips his thick wooden nightstick into an open jar of greasy pomade then forces it in Freddy's asshole slowly pushing it painfully deep in his ass. Grinning with pervy pleasure as Freddy howls from the sharp burn and begs him to take it out. The bearded guard grins at the sight of his bruised heavily welted ass and his partners obvious pleasure in violating him most painfully.

What none of them are aware of, however, is Charlene watching intently from behind the large one way glass mirror and fingering her sopping snatch to her 6th toe curling climax. Or of mother Cordelia wearing only spike boots, panties and bra with her heavy legs spread wide. Watching the action below on hd widescreen, close circuit tv in her office. She feels familiar heat and swelling as moisture gathers between her legs. She speaksinto her intercom. "Come in here. Suki." A slim petite naked Japanese girl entets carrying a large hitachi and kneels between Cordelia's powerful thighs.

"Just a little taste, Freddy. Next you disrespect Miss Charlene we gonna have some real fun!" The guard pulls the greasy stick out of Freddy's asshole with a loud pop and they drag him back to his room. Charlene enters Freddy's room late that night and smiles as she inspects his roughly savaged ass and rudely violated anus as he sleeps soundly on his side, sans night clothing. The next few days are uneventful until the same 2 latex clad guardesses escort him to Wardress Cordelia's inner office.Haughty and cool they very fit and practically carry him along as though he was a large size rag doll.. Cordelia is a sagging but quite buxom powerfully built woman with strong thick thighs and an enormous round ass. Her prodigious posterior even more apparent in her tan jodhpur riding britches and boots. She has on brown jacket over a white blouse. Her raven hair is worn tighly up and she is carrying a riding crop.

'Hello Freddy. fancy seeing you here! Just when you think you'll never see some little scuzbucket of a prick bastard again he shows up right in your face and you totally have him by the balls! Thats right, freddy! I can do anything I want to your fat worthless ass because I own it, now!" Freddy is frantic; "But money was paid out. What about my arrangement?" Cordelia smiles. "Arrangement? You're talking about illegalities now, Freddy. Besides that ratprick Carruthers is abroad somewhere with his daughters age mistress, spending your money. And your here with me. You remember me, don't you, Freddy? You ruined my family, took advantage and maliciously mistreated my daughter and put us both on the street without a dollar to my name!" But its a misunderstand...." "I don't want to hear it,Freddy!" Gag him! Here use this!" Cordelia finds a particularly pungent pair of well worn panties in her drawer. Samantha stuffs it in his mouth and wrsps around a bandana. "Now strip him!" They quickly remove his loose prison garb "Bend him over and show me his balls!"Redhead Samantha locks his neck between her long well toned ,red latex ensconced thighs while dark haired Lissette agonizingly stretches and pulls Freddy's balls down and back behind him.

"They look a bit bloated, Freddy. We haven't put a crimp in your masturbation routine, have we?" She laughs as smartly smacks his balls with the flat end of her crop. He yelps muffled but loudly and she smacks them harder. "Told you I had you by the balls ,Freddy and I'm going to thoroughly enjoy every fucking minute of it. She smacks them hard 3 times in quick succession and he screams in high soprano and its audible through his gag. They all laugh and Samantha nearly loses her grip. She continues punishing his balls for a few minutes more having guardess Lissette twist, stretch and painfully squeeze them, as well. "Now lets see that cock!" Lissette briskly masturbates him to a tumescent state then lets his cock sway in front as Samantha holds his arms behind him. Cordelia spanks his bobbing penis sharply with her crop. Amusing herself with slapping her elusisive target just right as it bobs and sways and watching Freddy's face grmace and contort.Lissette disapears for a few moments and brings something to Cordelia. "Bend him over my desk!" Lissette holds his stretched arms in front of him and Samantha fastens his ankles to a spreader bar. Cordelia hefts the large heavy wooden paddle in her hand . "I've always dreamed of doing this should we ever meet again. So guess what happens next? She swings the hardwood paddle fiercely into Freddy's plump posterior eliciting a muffled shriek of agony. Cordelia goes positively medieval on poor Freddy's chubby ass Becoming a fierce avenging Amazon and ferociously punishing his fleshy, shuddering asscheeks. Hotly swinging the wicked wood,. sometimes using both hands and making Freddy scream like a rump branded swine.The large cutting board size paddle welts and bruises his hard belabored ass even worse than before. Cordelias arms finally tire and she's out of breath. Samantha and Lissette drag him back to his quarters and Cordelia smiles at her wicked handiwork, Freddy's groans of agony and the sight of hot tears running down his cheeks.

It was nearly a week later when the girls played a little game with Freddy. His balls were locked in a genital pillory while his cock dangled down, on top.His ass had been heavily striped by Charlenes flogger and though he had struggled to stay reasonably still. He had wretched his balls most painfully more than a couple of times trying to escape her wicked whip.He had been put to bed in a chastity device and denied any release for more than three weeks. Charlene, Lisette and Samantha hegin sensually teasing Freddy. Circling around him, tweaking his nipples, lightly brushing his cock and balls, teasing his taint and anus and lewdly stripping and displaying themselves close to Freddy's hot, sweaty body. He wretches his fat, swollen balls once again automatically thrusting forward to try and grasp at some friction to get himself off. Cordelia begins teasing his balls and stiffened cock with tiny taps of her crop alternating with painful snaps as the girls step up their wicked game of tease/denial. It isn't long before Cordelia's crop forces out a copious but partly painful and non orgasmic ejaculation and she laughs at his helpless frustration.

Its now just past the 2 month point and Freddy's now near daily life of pain, subservience and humiliation continues unabated. Charlene and Cordelia have forced him to reveal the last of his hidden assets. They have been liquidated and the funds transferred to Charlenes offshore account at his considerable expense. Today he is nearing the end of his now, twice weekly milking. He is upended his legs held up , in place by tawny Samantha while Lisettes long, handled nightstick is embedded deep in his ass. She works it back and forth slowly as Charlene masturbates his down dangling cock. She relinquishes it just as it begins to throb. Forcing his mouth open by pinching his nose shut and adroitly using her other hand to fist his down dangling balls most painfully. She causes him to hose out a most copious load mostly in his wide open mouth and partly in his face. Danielle has just entered with the news. The bidding war among angry cartel chief's had been a very lucrative success. El Castroto has just conceded to El Puerco and the mind boggling amount has just been deposited in Cordelia's offshore account. The girls giggle at a recently sent photo depiction. "Well Freddy, some good news. You're going to be released almost a month ahead of your original arrangement. But you will be going to a special clinic owned by El Puerco. He was most displeased with you after you attempted to rob him and caused him tons of trouble when his operation came under federal scrutiny. He wants you as a sex slave and a feature attraction at his "no taboos" elite brothel. "The House of Pain" Its also necessary that you change genders and become a woman. He and his cronies apparently prefer their women to be fatties and mucho voluptuous. So you will look like this in only a few weeks time!" She shows him a photo of a huge fat woman with enormous jugs, Godzilla thighs and a massive ass. She also has a big cock and balls dangling between her legs." No! You can't! I..." "Gag him, Lisette! " Lisette stuffs his mouth with her panties. "There actually is a bright spot, Freddy! A doctor there has developed an injection which will greatly increase the size of your cock and balls. Downside is it will just dangle there cause it won't be functional, anymore." ( giggle ) " Danielle whispers something to her. "Bend him over, Samantha!" Go ahead Danielle." Danielle approaches him with a large syringe. "Sorry Freddy, but they want you right away and money's been paid so..." She giggles as his eyes widen in stunned horror and he shakes his head frantically. But Samantha holds him fast and Danielle painfully pokes his bare bottom with the sharp needle and quickly sends him to dreamland.


Postscript

Place: Valkyrie Island, a femdom island nation not far from Martinique, owned and ruled by Madame Odette Rouchard, Comtessa Maddo's sister.

Freddy is face down and ass up on his knees. His arms are tightly held behind him in a chartreuse leather armbinder. He is naked and the flared end of a thick, same color buttplug can be seen protruding from his anus.His ankles are shackled and attached by a short chain as are his bound balls.His stiff cock is pointing down and is drizzling clear lines of pre cum.Tan, tawney and very fit and toned Charlene, wearing only a red thong top, is seated next to him and she is amusing herself squeezing, poking and spanking Freddy's purple boaty balls. His fleshy ass is well striped and making muffled groans he appesrs to be gagged. " Oh, Freddy! Be still! You are such a drama queen about your balls!" If you hush, I might let you cum later, maybe!" She smacks his balls again and giggles when he unsuccessfully tries to stifle a loud groan. "I'm so glad I decided to keep you. Especially since you signed away your freedom and agreed to be my permanent slave here on the island. We were meant for each other Freddy and this is the way it was meant to be! We've been recompensated beyond what you stole and even Cordelia is happy. Sorry I played that nasty trick on you a few weeks ago but you were so funny frantic and the looks on your face were priceless! I'm glad we used that swarmy little prick, Carruthers to replace you. They said he kept insisting he wasn't you but Puerco and his people weren't buying it. Now he is severely disciplined whenever he mentions it and in a few more weeks he'll be a different ma...er woman. (giggle). My friend Arabella will be here in a couple of weeks with her new consort, Harry. Can't wait to meet him! Perhaps she had him sign some papers he didn't read just like you! (Giggle)

She works him around, lifts his head removes her thong bottom gag and grinds his face into her soppy wet snatch. " Now lick my pussy, Freddy! AAAHH! Thats right! Good boy!"