Cross-Dresser - Awakening Pt. 04

The evening meal was a cold affair, Mistress Penny didn't take her eyes off Samantha as she ate, Samantha in turn wouldn't meet her gaze and picked at her food, finally Penny spoke 'Not eating tonight, maybe you'd like some desert instead.

Samantha nodded, the thought of something sweet appealed to her, she heard a zip. 'Down on your knees in front of me' Samantha obeyed. Penny was still in her leathers and the zip had opened her crotch with an inviting pussy just inches from Samantha's face. 'You like what you see slut' Samantha nodded slowly and moaned as Penny brushed her pussy across her lips, Samantha took care not to touch and concentrated on keeping her clitty under control which was proving a job in itself.

'Are you ready for desert slut?' Samantha nodded, as she nodded Penny brushed Samantha's lips, the hint of pussy juice was intoxicating, 'Well go on slut, have your desert'. Samantha gently kissed Penny's pussy and ran her tongue slowly over the hot flesh, Penny sighed and moaned, widening her legs further 'OOHHHooo yes bitch that's so good' Samantha continued with the soft kisses and licking Penny's clitoris 'MMMMmmmmm, oh God yes, suck it suck me' Samantha obeyed and placed her lips around Penny's firm clitty and drew it towards her mouth, she could feel Penny tremble as she sucked, licked and kissed..

Penny's fingers went through Samantha's hair, Samantha tensed waiting for her mouth to be forced into Penny's crotch, but it didn't happen, as she felt the gentle caress of her hair her tongue penetrated deeper into Penny's pussy, the hot, wet flesh tasting so good and Penny's reaction proved she was enjoying her sluts performance. The tongue flicked Penny's clitty faster and then buried itself deep into Penny's pussy. Penny started to squirm and slowly grinding her hips so all of her pussy was serviced. Moaning louder Penny's head shot backwards as she cried out 'Yeeeessssssssssssssss' and Samantha was rewarded with a mouthful of pussy juice.

Penny was gasping for breath, 'Enough, enough no more hear me' Samantha stopped licking and resisted the temptation for one final pussy kiss, she instead knelt and waited, Penny's juices dripping from her chin. Penny composed herself, 'Come here slut and stand up' Samantha obeyed immediately feeling Penny's fingers exploring under her skirt. 'MMMmm a good girl all soft and dry, your learning fast'. Standing, Penny placed her lips over Samantha's and probed her tongue into Samantha's mouth, she moaned 'You like the taste of my pussy cum bitch' Samantha nodded and tried to dance her tongue with that of her Mistress. Penny stopped kissing her, 'AH AH AH, that's for another day. Now help me out of my boots'

Samantha first unzipped the left boot, resisting all temptation the suck on the heel, then the right boot. Penny stood up and turned around, 'Now my corset slut' Samantha gentle undid all the hooks and lifted Penny's corset from her breasts. Finally Samantha slid Penny's crotchless knickers down her long, sexy legs, 'That's better' as Penny shook her hair. Her perfect form now totally naked in front of Samantha. 'One day slut, one day' as if she read Samantha's mind.

Penny ordered Samantha to pick up her things and follow her, all the delightful leather was laid out in Penny's bedroom, 'Just removing temptation' 'Yes Mistress'. With that Samantha left her Mistress to relax while she did the dishes. After completing her chores Samantha went to her room, she opened her door and was shocked at the amount of rewards she had earned. Sexy satin dresses, boots and shoes, jeans, make up, several wigs and flowing nightwear. It was a happy Samantha that went to sleep wearing a soft, shiny, red satin nightie.

Next morning Samantha found a message by her bed, it simply said wear something flowing. She showered and had the closest shave she'd ever had and picked out some red cami-knickers, matching gown and open toed strap on sandals, the heels didn't bother her now, it was a happy Samantha who almost ran downstairs. Penny looked up approvingly 'Very nice baby' her tone shocked Samantha no curt remarks or put downs Samantha liked the new Penny.

'I've decided to work from home for a few weeks, you will stay here as my assistant', Samantha looked up, 'Yes Mistress, what ever you command' The next few weeks were to be brutal for Samantha, Penny's idea of working from home had no office tasks. Every morning Samantha was taught 'Pussy Control' She would parade in front of Mistress Penny wearing her tight PVC shorts, once Penny had checked her over she would get onto all fours and wait while Penny went through her assortment of butt plugs.

Each day Samantha would resist the penetration, her pussy muscles getting stronger against the intense pressure and vibrations until the day came where she was instructed to parade totally naked. Penny lubed Samantha's pussy hole and slowly pushed the butt plug halfway. She screamed with delight as Samantha sucked the throbbing monster from her palm, Samantha pushed the plug halfway out then sucked in, each movement brought Samantha closer to climax. Beads of sweat formed on Samantha's brow, Penny was quivering with expectation, gently rubbing her own, already soaked panties.

'MMMAAAARRGGGHhhhhhh' Samantha had the most intense climax ever, her whole body literally shook. Penny was quick to see Samantha's buttocks clench and pressed the base of the butt plug so every mind numbing wave of sexual fulfillment burst in Samantha's mind. Unable to remain in control of her body Samantha collapsed, rolling onto her back, something didn't feel right, her pussy continued to cum, her clitty was........Her clitty was enormous, thick, curving and dripping precum. Penny straddled her, pulling her own panties aside and slowly slid down it's full length, the thickness causing her to wince slightly. She drew herself up then slipped back down, Samantha wanted to push up but was afraid it would cause her Mistress to stop.

'Cum you bitch, cum damn you, it's what you want ISN'T IT?' Samantha knew this was her big test, Penny would get what she wanted but Samantha had to resist as long as possible. 'NO MISTRESS' she cried, 'You have always told me I mustn't soil Madams pussy AARRRRGGGGHhhhh' Penny manipulated Samantha's sacs, twisting and stretching the willing flesh 'Now you want to cum, you slut' 'No Mistress no MMMMaarrrgh' Penny released her grip and Samantha felt the surge of juice coming from her sacs, she shut her eyes and gritted her teeth 'No Mistress I mustn't cum, not without your permission' Samantha was ready to explode, she had already felt her first twitches and knew she couldn't last much longer 'Just a few more seconds, just a few more seconds' went through her brain until, at last, she heard a soft whisper 'You may fuck me bitch', 'AAAAARRRRGGhhhh' Samantha bucked and writhed under Penny, Penny gently stroked Samantha's firm nipples and gasped at the deepest thrust as it penetrated, Samantha's clitty pumped hard, pumped like she had never done before. Penny tensed as her pussy gripped tighter, squeezing every last drop of hot juice from her slave.

Once she was sure she had it all Penny slid off her bitch and snuggled up beside her. Samantha was still climbing, her clitty pulsing every few seconds, but her sacs were empty. She felt the soft caress of Penny's fingertips stroking her sides as she whispered in her ear 'Your such a good girl'

Over the next few days Penny and Samantha did standard office work at home, there was the occasional visitor who would take Samantha into the bedroom to teach her make up, nail care and how best to style her lengthening hair.

At the end of work each day it was Samantha's task to undress her Mistress, before she took her nap, then clean up the work desk, kitchen, table, any little job that needed doing. It was on one of these days that Samantha sat down on the sofa, the thought of Mistress Penny lingering in her mind. Samantha closed her eyes and stretched out, there was a thud. Samantha stopped daydreaming and looked on the floor to see what had happened.

She had knocked Penny's work bag over and to make things worse the contents spilled out. Samantha sighed and began picking everything up Filofax, make-up, diary and other bits and bobs found in a woman's handbag. As she put the contents back she noticed a small red book tucked deep inside the bag. Curiosity now got the better of her and Samantha opened the book. There was a strange list of two letter groups and a comment by each, Samantha's eyes widened;

Gi -- the perfect female slave, weakness is vibrating toys

Su -- complete cumslut, squeals and bucks when pegged

Lo -- loves to be feminized, easily controlled by manipulating clitty through silk

Ja -- quivers when stroked, needs restraint to stop cumming in her panties

GH -- likes being fucked but still resisting full fem, but I can wait

Al -- too young but one for later

Jo -- loves being pegged, clitty must be collared to prevent constant wanking

Sa -- ultimate sissy but too head strong, needs to be bested frequently to keep her under controlled.

She made a copy of the list and carefully hid it inside her bra, she replaced the odd little book and went to bed.

Samantha had a restless night, the contents of the little red book kept going round and round in her mind. Suddenly she sat bolt upright 'Too young, Al', could that mean Al the office junior, Su -- Susie and Sa, OMG it's Penny's list of slaves. Samantha had never considered that Penny had such a life outside of their marriage, a life that she had seen fit for Samantha to be now included.

There was no more sleep that night, instead Samantha lay awake trying to make sense of her new life, and was it what she truly wanted. She was happy being allowed to dress fem but she wanted more. Mistress Penny said that Samantha's new life would be on her terms, a cruel world where Penny would get her sexual kicks by inflicting pain and suffering. Samantha swore she would find a way to remove herself from Penny's slave list, A wry smile came across Samantha, 'Yes the list'

Samantha came down for breakfast, Penny drew breath as her slut came into the room, 'Very, very nice, I see you find the new clothes to your taste' Samantha was dressed in a satin blue chemise, tight blue jeans and high gray boots, as usual Penny checked her, gliding her fingers beneath Samantha's crotch, 'MMMmmmm so smooth, so soft and you've even tried your make up, not bad for a first solo attempt' Samantha had tried to make up her face, but with a little too much blusher, which Penny fixed, pale blue eye shadow and glossy red lips. Her now longer, natural hair had been slicked with gel and.styled into a short 'bob' She and Penny left for the office, Penny's hand firmly placed on Samantha's ass..

They arrived and took the elevator, once again Samantha felt the soft touch of fingers groping her, but this time, instead of rejecting the advance, she pushed her buttocks back crushing the foreign digits between her and, she turned, a red faced Al. Penny watched enviously as her latest slave was making a play on what would be her next victim, but made no comment. Samantha's entry to her work place brought, at first, stunned silence, followed by wolf whistles and moans, she just smiled and went to her desk.

It didn't take long until Samantha was summoned to Gerry's office, she was about to knock on the door when she saw it. Gerald Henderson -- Supervisor, 'GH' she whispered to herself. She knocked and entered, there sat Gerry. He looked up and smiled as she slowly & seductively moved towards him. 'Please sit down won't you, I was going to talk to you about the way you dress........., but, erm, I' 'Yes' purred Samantha.... Gerry couldn't take his eyes off her. 'I...er.... hmm...Well back to work now'.

Samantha brushed against Gerry's desk knocking some pens onto the floor 'Ooops clumsy me' as she knowingly bent down in front of him, her tight jeans causing him an instant erection..

Samantha left a flustered and blushing Gerry and went back to her desk. Susie was open mouthed when she saw her and slowly licked her lips, mouthing 'Later Honey' Samantha couldn't wait 'Squeals when pegged',.Samantha smiled back, 'Yes sweetie, we'll get together......... later.