Cross-Dresser - Awakening Pt. 07

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Samantha meets Janet and takes her from Penny.
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Part 7 of the 10 part series

Updated 06/11/2023
Created 07/18/2022
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On her way back to the main office Samantha paid a visit to Accounts, she looked through the window and scanned the room. 'No not her, maybe, ahhhhh got her.'

Janet was sitting quietly at her desk and her love of faux leather was obvious, red leather waistcoat, matching knee length skirt and spiked heels. She looked striking with shoulder length jet black hair, full lips and very dark eyes.

Now Samantha had seen her she worked out a plan to get to know her.

Samantha was pretty spent but thought by this evening she would have regained all her strength and guile. She went downstairs and back to her desk. On her way past Gerry's office she waved and blew him a kiss, he was so frustrated without Susie and Samantha wanted him to become besotted with her, then she would tame him.

At the end of the day Samantha hurried outside and waited for Janet, she saw her, very tall with long legs, Samantha glossed her lips and strolled up to her, 'Hi hon, your Janet aren't you?'

The girl looked perplexed, 'Yes, do I know you?'

'No, but we both know Mistress Penny.'

Janet's eyes were full of foreboding 'She's sent you hasn't she, I've been good I can't help getting excited. Please don't take me to her I can't stand it any more.'

Samantha put her arm around her waist, brought her head up and looked into her eyes, 'Don't worry hon I'm a friend. Penny doesn't even know I'm here and we need to talk.'

Janet smiled 'OK I'll trust you, but any tricks and I'll contact Penny..... about you.'

They went to Samantha's car 'Would you feel more comfortable talking at home or would you like a drink?'

'A drink would be nice' replied Janet as she got into the car.

Samantha drove to a quiet little bar she knew. They found a table and it was Samantha doing most of the talking.

'Janet I can see by your reaction that you want to get out of Penny's clutches' Janet nodded, 'And you'd do anything to make that happen?' Again she nodded and took a sip of her drink. Samantha's fingertips stroked Janet's hair,

'Mmmmmmm that feels nice' moaned Janet as she shuffled a little closer.

The more Samantha stroked her hair the more relaxed Janet became until she gave Samantha an unexpected kiss on the cheek.

'I'd like to go home now, please' kissing Samantha softly on the lips. They went to the car snuggled together, their arms around each others waist. On the way home Janet stroked Samantha's thigh, 'Your jeans are so tight' Samantha smiled and blew her a kiss.

At Janet's Samantha saw nothing untoward, that was until Janet showed her the bedroom. A leather and chain harness hung above the PVC covered bed, 'That's where she puts me when I cum too soon and she makes me wear this' Janet undid her leather skirt and let it fall to the floor, her panties too and hung her head in shame.

Her clitty was caged, she couldn't get a hard on without severe pain and cum constantly dripped from her swollen head.

'Where are the keys?' demanded Samantha,

'Up on the shelf, but I mustn't touch them. No Samantha leave them Penny will find out.'.

Samantha found the keys and released Janet from her clitty hell.

'OHHHHhhhh Yesssssssss' Janet pumped instantly as her clitty grew to it's full length and thickness.. Samantha took down the harness and sat on the bed next to her.

'You feeling better?'

'MMMmmm, can't you tell?' as Janet touched her swollen clitty.

Janet slowly unzipped her waistcoat revealing her ample breasts and firm nipples. 'Penny gave me implants.' they looked so good that Samantha leaned across and kissed both, while running her finger under both nipples. Janet shivered and her clitty twitched, Samantha knew that before long Janet would be hers.

Samantha undressed, her own clitty still under control, she removed her jeans and top, then put her boots back on for they formed part of her plan. Samantha's soft red lips kissed the tip of Janet's clitty, 'OOOHHHHHhhh' she moaned.

A hot tongue flicked at the thick vein on the underside of the solid member. The more Samantha used her tongue the more Janet was falling under her spell. Precum seeped from Janet's cum hole, Samantha ran her finger over the purple tip and rimmed her own pussy with the sticky juice.

Samantha lay back on the bed and gestured for Janet to make use of her clitty. The tip sought out Samantha's love hole 'AAAHHHHHHhhh' Samantha's pussy ached as she was invaded, Janet started to move her hips, slowly at first, then thrusting harder and deeper.

Samantha curled her legs around Janet's body, the leather boots caressing and heels scratching her back and ass.

Janet sighed and squirmed until.............'OMG OMG no no not yet.'

Janet's unused, swollen sacs shot their load, Samantha screamed as it flooded her but still held Janet firmly between her thighs and boots

'You liked that, didn't you?' Janet said nothing, 'Didn't You?' as heels were dug deeper into Janet's flesh.

'Yes, yes you know I did' Janet cried as a spent clitty fell from Samantha's pussy.

'I thought you did.' Samantha spun her victim onto her back, the boots now stroking Janet's sides as she straddled her.

Janet was beginning to panic, 'What now, what do you want?'

Samantha curled her fingers around Janet's limp clitty rubbing slowly the until the stiffness returned, leaving Janet purring as she surrendered to the hand job. Samantha offered her pussy to Janet's mouth and was rewarded with a soft kiss, then a hot tongue probing her hole and eagerly licking at the dripping cum.

Janet's second climax covered Samantha's fingers in cum, the third and fourth made Janet cry in pain as her empty sacs had nothing more to give, 'Mercy MMMPPPPHHHhh' she cried. Samantha gagged her by lowering her pussy further onto the sluts mouth.

'Oh baby, I'm sure we can find a little more' as Janet's clitty hole was opened and a sharp finger nail pushed within, Janet bucked and twisted but Samantha wouldn't let her go.

As her clitty was being assaulted Janet also had the pleasure of her shaft being stroked and the soft leather against her sides.

Samantha sat tight until Janet stopped struggling. Now she moaned and squirmed on the PVC sheets as all her senses began to melt into one, she was under Samantha's control and she wanted more.

There was pain, but unlike Penny it was a nice sexual pain that drove her mind into wanting much much more, Samantha let her breathe, 'Thank you Samantha, that was perfect' Janet was running her hands over Samantha's boots cooing and kissing pussy.

Now it was Samantha's turn to moan as she released her own clitty from it's pantie prison. It was a breathless Janet that first saw Samantha's throbbing clitty 'Please Mistress, would you like me to roll over?' She had her. Samantha lifted from Janet and the obedient slave went instantly on to all fours, her pussy open and expectant.

Samantha moved behind her and let her clitty rub juice around Janet's pussy.

Janet tensed, then relaxed as Samantha stroked her hips and gently pulled her back. Samantha groaned as her firm tip slowly widened and entered Janet's body. Her pussy was so tight, Samantha stroked Janet more but though she became more relaxed, her pussy flesh wouldn't yield.

'Am I doing anything wrong Mistress?' inquired Janet, 'It's my first time.'.

Samantha smiled, 'No honey your doing just fine' pushing slowly, but firmly until Janet gasped, her virginity now gone forever. Samantha pegged Janet in a tender and loving way. The virgin squealed when her pussy was filled with cum for the very first time.

Slowly Samantha withdrew and lay next to Janet, who cuddled up immediately and kissed her new Mistress.

They lay together for many hours, Samantha contemplating whether she had been right to seduce someone who had known only Penny's cruel love just so she could take Janet for herself.

Janet began to tell of how she met Penny. 'She found me in a bar, I was new to cross dressing and it was my first time out. She told me she could make me look more feminine, and how leather suited me.She bought me lots of clothes which did make me feel really feminine for the first time.'

'After that things changed, Penny's cruel streak soon took hold forcing me into a life of bondage and making me her sex slave. She got me the job in Accounts just so she could keep me near her and called me her cumslut. The pain from my clitty cage, being in harness and hung was just so Penny could fondle and punish me. It became my life, it was like a drug'.

Samantha again ran her fingers through Janet's hair, 'That's all over now, you belong to me and I won't hurt you, understand?'

Janet nodded 'Yes Mistress Samantha.'

Samantha dressed and left a cum soaked, but happy Janet, laying in PVC heaven purring and rolling her palm over the tip of her clitty.

Taking the list Ja was marked with an X

Samantha had already picked her next target. Gerry must be gagging for it by now and Samantha was just the Gurl to ease all his troubles, but that could wait until Monday. Penny would be back in a week and Samantha had to complete the turning of all of Penny's slaves.

Sighing as she got into her car she hoped that a week would be enough time to find who Lo was from the list.

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