Cross-Dresser - Awakening Pt. 10

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Mistress Penny returns & Samantha knows it's the End Game.
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Part 10 of the 10 part series

Updated 06/11/2023
Created 07/18/2022
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Tuesday morning and Samantha arrived to a happy workplace. Gerri was gleefully wriggling in her office chair as her fem under clothes drove her wild.

Susie had returned and was relieved at not being Gerri's centre of attention.

Janet was dressed in leather as usual and giving herself hourly orgasms now she was free of her cage.

Samantha caught Ginger and Alice in the stationary cupboard so many times it was pot luck as to who would be found pegging who.

As the week went on the tension rose, everyone was dreading Friday. Samantha tried to calm her Gurls and calmed herself by staying away from home and sleeping with Louise.

Friday came and there was a distinct lack of the carefree existence, Ginger was back in her drab suit, Gerri was trying not to squirm or smile too much, Al stayed away from the main office while Samantha, Janet and Susie got on with their work not daring to look up.

10:45am and everyone heard the dreaded click of steel heels on a marble floor, SHE was back.

Her first call was the main office floor where Penny pointed at Susie 'You, come with me.'

Susie looked forlornly at Samantha, who could do nothing but silently mouth 'Go on hon.' Susie got up and followed Penny at a safe distance.

Everyone heard the screaming. It was aimed first at Ginger, then Susie, all looked at each other in vain.

After what seemed an eternity Penny dragged a crying Ginger and a very frightened Susie into the office. Gerri went to get up but one icy glare from Penny and she thought better of it. 'You, SLUT,' Samantha looked up, 'I've got a little task for you.' Samantha swallowed hard and got up, as she got nearer Penny grabbed her, 'Take my car and deliver these two to this address, Ginger knows the way, and stay there until their correction is complete.'

'Correction?' thought Samantha.

'And don't take too long about getting there, Joanna is waiting' snapped Penny.

It was a slightly happier pair who went with Samantha to Penny's Jaguar, 'It's the perfect chance' said Samantha 'Penny's last slave.' Ginger was still worried, she'd heard all about Joanna and she wasn't like any of the other gurls..

'In what way?' asked Samantha.

'She has a cruel streak, almost as bad as Penny's but providing she worships Penny then she is allowed to operate as she wishes.'

Samantha thought hard, 'We'll go along with her games and while she's having her fun with you two I'll have her.'

'Some plan Mistress, thanks' remarked a sarcastic Susie.

Samantha stroked her face, 'Don't worry it'll be alright.' Samantha looked ahead trying not to show any signs of worry

Ginger guided Samantha to Joanna's home, a vast mansion in it's own grounds. As they approached the door there was a brass plaque 'Mistress Penny's House of Pain & Correction.' It was a nervous Samantha that rang the bell.

The door was opened by a large, muscular female wearing a lab coat, 'not Penny's type' thought Samantha.

'Yes what do you want?' was the abrupt greeting,

'I'm here with some soiled goods from Mistress Penny.'

Joanna smiled, 'Oh yes, I was expecting you' she pinched Ginger's cheek. 'Follow me.'

They were led into a spacious reception area, Samantha was told to take a seat while Ginger and Susie were manhandled into a room marked Correction Suite.

Samantha relaxed a little waiting for the right moment. As she flicked through some girly magazines. 'AAAAIIIIIIEEEEEEEEEeeee'.

A blood curdling scream focused her attention, 'That was Ginger' and second scream 'Susie, what's she doing to you.'

Samantha opened the door a little. On the floor was a box marked Bondage Pants. Ginger had her arms tied behind her and her ass stuck out, she was wearing nothing but a pair of these latex pants, which buzzed ominously and very high heels. Joanna amused herself by lazily flicking a soft red whip across Ginger's ass.

Susie was bent backwards, her hands tied and stretched behind her. She was wearing the same outfit and her solid clitty was engulfed by a cum milking machine which was effortlessly draining her sacs.

Joanna saw Samantha, 'Come in my dear, this is what happens when you displease Ms Penny.' Joanna had removed her lab coat revealing her flawless ebony skin. She wore a dazzling white swimsuit and white knee boots

Joanna approached Ginger, she was trembling, beads of sweat covered her body. 'This will shut you up' as she ball gagged the helpless woman and turned up her vibes.

Ginger gave a muffled scream as both butt plug and dildo shot waves of both pain and pleasure through her already wrecked body. 'Always nice to have a female occasionally, two holes to play with,' remarked Joanna

Joanna now turned her attention to Susie, 'Pity only one hole, but there's always this' as she produced a cock ring, forcing it over Susie's clitty and refitted her to the unfeeling machine.

The pain was too much, Susie cried out as her clitty swelled and her sacs ached. 'I do love the sound of pain, don't you?' laughed Joanna.

Ginger was barely able to stand, she tottered in her heels, her body glistened with moisture. She looked appealingly at her Mistress.

Susie was now in worse shape, Joanna kept forcing her butt plug in deeper trying to break her..

It was obvious to Samantha that she was watching a callous individual who loved sexual torture.

Ginger's head dropped, she moaned loudly into her gag as hot juices flowed down her thighs, Joanna glanced across to her 'Good, only seven or eight more and you'll be much more co-operative.'

She turned her attention back to Susie, 'Come my dear, it's time you squirted another full load' Susie sighed but refused the invitation to cum.

Samantha hated what she was seeing, she couldn't even stop her own clitty being aroused, something which Joanna couldn't help but notice. 'Here honey let me help you with that' stroking beneath Samantha's skirt. Samantha was in heaven, Joanna was very proficient at the art seduction.

She returned Joanna's affection and was soon running her hand up her dark thigh, Joanna smiled 'Go a little higher dear, it's alright' Samantha eased the swimsuit crotch across and found..........a female pussy 'MMMMMMMmmm moaned Joanna 'That's it go higher.' Samantha obeyed and found.....a swollen clitty, which strained against a tight clitty collar firmly squeezing on it's shaft, Joanna was an hermaphrodite.

Samantha went down on her knees transfixed on Joanna, she kissed the throbbing mass and slipped two fingers inside the hot, moist pussy.

Joanna spread her legs 'YYYYYEEESSSSSSsssss, Ms Penny said you're a gifted bitch' as she ripped the crotch material and forced her clitty into Samantha's mouth.

Samantha willingly sucked, lapped and played with Joanna until she shuddered 'Your such a good little slut let me reward you, AAAHHHHH' despite the pressure of the collar her clitty pumped a full load, Samantha's mouth was awash with thick, salty, hot cum.

Joanna's pussy tightened around Samantha's fingers as she lay back onto her consulting couch.

Samantha forced her fingers to move in the tight hole widening Joanna's pussy before adding a third then 'OMG YEESSSSSSSSSSs'. Samantha forced her hand and wrist within the cavernous hole, fisting Joanna for all she was worth.

'Your mine slut', demanded Samantha as she pumped Joanna's pussy whilst giving her cock a fast hand job.

'Never, I belongggggggg, belong to Mistress Penny' the helpless Joanna cried. Samantha tugged on Joanna's cock while still forcing her hand deeper inside her pussy, 'AAAIIIIIEEEEEEEE,' tears rolled down Joanna's cheeks..

'Just say it cumslut'

Joanna frantically shook her head, 'No No I only take commands from Mistress'......... she arched her back as her pussy was stimulated, .........'PENNY.'

Joanna writhed and bucked getting ever closer to sexual fulfillment 'Faster, faster bitch, yes that's it, don't stop, don't STOOOO.............PPP.'

She could take no more, she both gushed and pumped bathing Samantha's fingers in both pussy juice and cum.

Samantha forced her sharp nail deep into Joanna's cum hole and kept probing until her victim could take no more. Samantha hoped this was her moment, Joanna's body quaked, her mind was awash, but still she wouldn't submit to Samantha.

Joanna was out of control and shrieked as her cock was once more forced to cum squirting it's salty treasure high into the air, 'No more, pleas'......Joanna passed out.

Watching Samantha at work didn't help Ginger nor Susie, their bodies were already in a weakened state and now their minds were driven sexually insane, both were near to submitting to the evil Joanna.

Seeing their plight Samantha switched off both vibrating bondage pants, Ginger visibly sagged, dripping juice from her soaking pussy.

Samantha released her gurls from their rope bonds, helped them out of the dreadful devices and told them to dress.

She then turned to the still unconscious Joanna, no matter what she did to her Samantha knew Joanna would never break and betray Penny.

Staring at Joanna's soft cock and wide pussy Samantha had an idea. The three of them trussed up and gagged the helpless Joanna, bundling her into the boot of the Jaguar.

Going back inside they opened Penny's Cupboard Of Correction and selected a number of choice sex toys with which they would later entertain their 'guests'.

It was a breathless and very, very wet Ginger and Susie who got back into the car. They instantly marked the seats. Samantha giggled, 'What will Mistress Penny say?'

Ginger at first frowned, looked at the sopping wet seat, then burst out laughing.

'Did you make the call Mistress?' Samantha turned to Susie, 'Everything's' ready baby, EVERYTHING.'

Evening was drawing near as Samantha skidded the Jag into the office car park, the three of them then staggered inside carrying the helpless Joanna.

Samantha made one more call. 'Hello, Mistress Penny I'm back with your sluts but something terrible has happened and I really think you should come down here right away.'

Penny screamed down the phone, 'What, what's happened, is it my car, did Joanna go too far, what?'

'Best you come and see for yourself' and before Penny could reply Samantha hung up.

By the time an angry Penny had caught a cab and arrived at work it was dark. She checked her beloved car for damage sighed with relief and went inside the building.

When she arrived at her floor all was in darkness, she tried the lights, nothing happened.

After crashing her way through Ginger's office she opened her own office door

She tried the light switch, nothing, all she could hear was a soft buzzing and someone panting 'Who's there?' she cried

'Who indeed, SLUT' came the sinister reply

Before she could make good her escape several pairs of hands came out of the darkness grabbing Penny, she screamed, but her anguished cry was cut short as a PVC glove covered her mouth.

Penny felt a mask being placed over her eyes.

The lights came on.

Penny felt herself being stretched out on what she assumed was her desk. Her black dress was torn from her as were her silk panties and bra..

Leather wrist and ankle cuffs were fastened tightly restraining her to the desk The glove over her mouth was replaced with a pony gag which Penny licked and sucked on..

Penny could hear many clicks of heels which seemed to be all around her and the buzzing now grew more intense, as did the grunting.

'Who are you, what do you want money, jewels, I can pay you' mumbled Penny

A voice whispered hoarsely in her ear, 'We want our freedom, BITCH.'

The voice was familiar but Penny couldn't place it, she felt the ankle straps being removed and hands lifting her legs higher, 'Stop stop it' she cried,

'The voice was back 'And this is just for you.'

She felt something slip over her legs then pressing against her pussy and ass, slight pressure and 'AARRRGGHHHHH.' The tight fitting bondage pants caressed her as the dildo and butt plug slid neatly into place.

Penny's pants were set to pulse, it was pure torture, she was allowed to relax before it hit her again. 'MMMUUUUUWAHHHHHHh.'

Hour after hour Penny's torment continued, her pussy ached, her ass felt worse, all she wanted to do was orgasm.

A stiff clitty rubbed against her.

Her firm nipples were twisted, kissed and sucked, Penny was being driven sexually insane.

Slowly the latex pants and pony gag were removed, juice dripped from both dildo and butt plug. Penny moaned as her pussy was released but her relief was short lived.

She felt pressure being applied to her ass, 'NO NO NO NO NO I've never taken analllllllllll.' Her back arched as a monster clitty filled the void and a single finger flicked her clit.

Penny was begging to be allowed to cum and be pussy fucked, but the huge clitty was probing her in ways she never imagined, her resistance was gone, she was helpless.

She squirmed as she was filled by the mystery clitty and groaned in ecstasy.

Penny felt the clitty slowly withdraw and gasped as the tip softly stroked her flesh,

'MMMMMMmmmmAAAARRRRARRR' Ecstasy turned into more pain as now her pussy was slammed by an equally hard clitty.

Penny's flesh was covered in beads sweat, her normally pristine hair hung lank and wet over her face. She had an orgasm at least four or five times and each time she had been fucked the clitty showed no sign of becoming soft nor sacs empty.

That voice again 'Had enough slut?'

It was a breathless Penny who cried out 'Yes, Yes I'm yours, do whatever you want' Samantha smiled and lifted Penny's mask, 'You!!!..I'll make you paAAAIIIIIEEEEEEEE.' A vicious vibrator was slammed against her pussy, Penny couldn't fight any more.

'You were saying bitch.' Penny had tears rolling down her cheeks as she looked round the room. Susie, Samantha, Ginger, Gerri, Janet, Al & Louise all dressed in basque, stockings and heels looked down upon her helpless body.

Penny twisted to see the other moaning figure.

A helpless Joanna was trussed up in a corner of the room, Penny's own sex toys continually pumping her pussy and sucking on her cock giving her multiple forced orgasm. Penny slumped, she knew they were both finished,

'Yes Yes you can have what you want' the gurls all moved nearer to her body. Samantha was at the end of the table resplendent wearing a red PVC basque and wicked thigh boots, her clitty now pressed against the pussy of her former Mistress,

'Gurls, you heard the bitch, do what you want' as she slammed her clitty fast and hard inside Penny causing her to scream.

Ginger silenced Penny by spreading her pussy over her mouth, the Gurls meanwhile rubbed their clitty, brushing them against a trembling Penny's body.

Penny struggled weakly and moaned when her breasts and tummy were bathed in hot cum.

Ginger felt Penny's tongue probe deep into her pussy and moaned in ecstasy as Penny's nipples and breasts dripped thick, warm cum.

Penny was spent, but didn't care, she felt Samantha's clitty fucking her hard and was gladly tasting Ginger's moist pussy, she sighed in contentment. Even when Samantha told her she was her slut Penny just nodded and moaned louder.

Sensing Penny's wicked reign was now at an end she was released from her remaining shackles and her hands immediately wrapped around Gingers legs as she buried her tongue even deeper into her pussy.

This time it was Ginger's turn to moan loudly and Penny was rewarded with a gush of pussy juice.

Samantha gently slipped from Penny's pussy and felt her inner thighs, they were soaked with hot juices.

She smiled at Louise, who, as usual, was very hard and rubbed the tip of her clitty against Penny, there was more moaning as Penny willingly lifted her legs high and wide wanting another anal session, Louise gladly obliged.

After many hours Samantha led her slaves out of Penny's office, each kissed her as they passed, Louise was the last, Samantha kissing her tenderly. 'Hi Honey' whispered Louise as she snuggled close.

Samantha held two leashes, she tugged on both.

Now dressed in white PVC bra, panties, stockings, white ankle boots and a white, studded collar spelling out the words Slut & Bitch. Penny and Joanna crawled out on all fours. They kissed Mistress Samantha's red thigh boots, both sluts purring like kittens.

Samantha looked down, smiled and thought 'Well Penny, you've certainly had quite an Awakening'.

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