Cross-Dresser - Awakening Pt. 03

Samantha woke early, she stretched thinking 'that was a lovely dream'. Her hand went to rub her cock, eyes now open as she stroked her pale blue baby doll and the cold realization that this was no dream. The locked clicked and Mistress Penny opened the door, she was already dressed and ready for work. Her black hair was slicked back and tied in a tight pony tail that gave her power dressing a sinister feel as she had put on a new two piece pinstriped suit comprising jacket and short skirt both very tight fitting. 'Up slut, and put these on, several garments were draped at the bottom of the bed.

Samantha stood and went to wash, quickly she checked her baby doll for stains, the tell-tale cum stain was there for all to see, she groaned and tried washing the nightie out before she was caught. Penny had been waiting for this moment, 'We still can't control our excitement, CAN WE?' Samantha had her head bowed awaiting her fate. 'Little cum sluts don't deserve my generosity' as she removed the top and trousers she had planned for Samantha to wear, Penny returned with another hanger and threw the clothes on the bed. 'I was going to be easy on you for your first day out but now you can learn what it's like to be a woman in the workplace.

The door slammed and Samantha looked at her outfit, there was the bra and falsies, white panties, a white blouse, which proved difficult to button as Penny had increased Samantha's breast size, a tight, black skirt, black hose, tie and a straight, shoulder length, blond wig.

Samantha dressed, tucked her cock away and admired herself in the mirror, again she approved of her look, then went downstairs. Both she and Penny had a light breakfast but when Samantha got up to retrieved her car keys. 'Going somewhere?' queried Penny, 'To work Mistress' Samantha began to squirm, 'we're going in together slut, I don't want you failing to arrive' Samantha zipped up her ankle boots and they both went to Penny's car.

The journey to work was uneventful, Samantha was loving the feel of long hair as it brushed her neck and face but was dreading what would happen once at work. On arrival Samantha was forced to walk hand in hand with Penny, once inside they traveled in the crowded elevator where Samantha had her first unwanted attention as she felt fingertips rubbing her arse, she turned and saw the office junior with a guilty look on his face, Penny smirked.

Though they worked together Penny had a much higher position with the company so while she went to her office Samantha took her place in the open plan work space. Her desk was shielded on three sides so she relaxed a little, but waited for the first comments.

As the morning progressed there had been a few double takes and the odd whistle but Samantha's work had kept her mind from dwelling on her situation. She had seen Penny go into the Supervisors office so wasn't surprised when she was called forward. Gerry sat at his desk and looked up as she entered. 'Well Penny had told me to expect a change in appearance, but this, WOW' Samantha blushed 'so what do we call you cutie? Samantha resented his manner 'Samantha, Sir' she replied 'Is that all?. Gerry seemed stumped for words at her casual reply and gestured for her to leave.

As she walked back to her desk she heard Gerry call out, 'The new girl is Samantha folks. jeering and laughter filled the air until Samantha got back to her work place, at least now most of them couldn't see her. As she sat down she noticed that the girl opposite, in the next row, was looking at her. She looked stunning wearing a figure hugging dress that left nothing to the imagination and knee length, tan coloured boots, 'You look fantastic' she silently mouthed, 'Meet me at lunchtime'.

Samantha vaguely knew the girl, she was an old friend of Penny's who had been to their wedding where a drunken Sam had made a pass at her. The morning dragged on until lunch, Samantha just wanted to get out of the building away from her colleagues. She found a shady bench and sat down with a sigh, she had not been ready for this. After a few minutes the mysterious girl joined her. 'Hi I'm Susie, your very brave, it took me months before I dare wear Fem in public. Penny told me you had come out but I never expected this'. Samantha was dumb struck, 'You mean your....?' 'Yes' laughed Susie 'I've been Trans for years and take no notice of Gerry, he's a queer and gets his kicks going out with me' Samantha smiled for the first time that day, a least she had one kindred spirit in the office or so she thought.

Susie whispered something to Samantha which made her giggle, then slid her hand up Samantha's skirt, 'Just checking your all smooth at the front' Samantha was shocked but willingly opened her legs, soon Susie's fingers were feeling their way along Samantha's shaft, it firmed immediately 'OHHHhhh babe you were doing so well, now I'll have to tell Mistress Penny you've been a bad girl'. Samantha quickly shut her legs, trapping Susie's hand, 'Let's not waste this honey' as Susie stroked the shaft and curling fingers around it. Samantha was in heaven, slowly her legs opened again and she felt Susie's expert manipulation of her cock and balls. She found herself moving her hips forcing Susie to wank her harder, she gladly obliged. Samantha's grunts were starting to get louder, Susie stopped this by placing her lips over Samantha's giving her a long, lingering, hot kiss until a final soft moan and Samantha gave up her load.

Susie ceased her embrace and tucked Samantha's limp cock back in place slowly rubbing and patting the cum soaked panties and hose then slowly sucking her fingers, she saved the last finger for Samantha who's eager tongue lapped at the salty reward.. 'Now that's another thing I have to report you for' Samantha cringed 'Please don't' she whimpered, 'but I must, Mistress Penny told me to report ALL your misdemeanors, and I must obey her'

Susie gave Samantha a peck on the cheek 'Never mind, you'll soon learn obedience and control, we all have' with that final kiss she was gone. Samantha slowly licked her lips, they still had the taste of her cum and the thought of Susie's kiss, it had been so sexy and Susie knew it would bring her off. So Susie spied for Penny, Samantha wondered how long Susie had been Penny's slave and who were 'We'. She looked at her watch, time to get back to work

The afternoon passed with little incident, except for when Samantha went into the stationary cupboard only to be joined by Gerry who squeezed his body next to hers, it was obvious he had a hard on, which Samantha took as quite a compliment. At the end of the day Samantha was walking to the car park when she heard a squeal of delight from Susie, Gerry had whispered something in her ear which highly delighted her. Penny was already outside, she and Susie smiled at each other and Samantha caught what she thought was a crafty wink. 'Enjoy your first day slut?'

Penny's phone sounded and she quickly checked the message 'Get in the car slut' she hissed, Samantha knew the message was from Susie and no words were spoken on the way home. Penny strutted into the house, her long legs looking even more magnificent then usual, Samantha followed, closing the door and falling to her knees, looking at the floor. 'So who's the slut who still can't control herself' 'I am Mistress' came the sorry reply. 'Get upstairs bitch and be undressed by the time I get there'

Samantha ran upstairs falling and tripping in her boots, quickly she undressed, Penny came in to find her sat on the bed. 'I checked your sheets earlier and noticed your baby doll drying, you've had a really bad day, HAVEN'T YOU'

Samantha again fell to the floor, her head by Penny's steel heel which she kissed, softly 'Please, Please Mistress I did try so hard to be good. I will do better tomorrow' 'I'm sure you will' remarked Penny 'Now put these on and remain on the floor. A pair of white PVC shorts were dropped by Samantha, she loved the intoxicating smell they gave off.

Samantha struggled into the tight fitting shorts which left nowhere to hide her bulge, so she tucked it as high as possible in the hope Penny would be too busy to notice.

Penny returned resplendent in black leather, her thigh high boots and corset were giving Samantha very improper thoughts as she tried to control her cock. 'On your hands and knees slut' Samantha obeyed 'Now onto your front and lift your arse'

Penny walked around her slut, 'I have a new rule for you slut' as she ran her hand over Samantha's tight shorts feeling between Samantha's buttocks and pressing on her hole. Samantha winced 'This my dear Samantha is now your pussy, 'Yes Mistress' 'And this', Penny prodded Samantha's throbbing cock with her long steel heel 'This dirty little thing is your clitty, UNDERSTAND?'. Samantha felt the pain of Penny's heel but stopped herself reacting for she was sure more pain would follow. 'Yes Mistress I understand I now have a clitty and a pussy'

Penny purred with pleasure as she reached inside a bag she had brought with her, Samantha felt the shorts being stretched and a cold, oily liquid flowed over her pussy it felt so good that she began moving her hips in an attempt to spread the substance. A quick slap focused her attention. 'Now cumslut when you feel this against your pussy I want it to remain exactly where I put it, clear' 'Yes Mistress' Penny pulled back the shorts and giggled at the butt plug in her hand. Running the tip against Samantha's body she waited for her to flinch as it found her pussy. Samantha tightened her pussy, exactly the reaction Penny wanted.

With the shorts acting like a clamp that was trying to force the butt plug inside Samantha's pussy. she concentrated hard to resist the force. Penny straddled Samantha's back, her thigh boots rubbing against Samantha's sides, 'That's it you slut try your best to fight the urge, you'll take it before long' Penny's eyes were transfixed on the bulge over Samantha's pussy, it moved slowly inwards and Samantha screamed forcing it out of her pussy, Samantha knew it was an unfair fight but to give in too soon would lead to a greater punishment. Penny was impressed so decided to take things one stage further.

Penny rose, 'Do you know what this is slut? As she held a small device in front of Samantha, 'No, no, nooooo Mistress' 'Well it does this' A soft buzzing filled the air and Samantha squealed in delight, her whole body quivered with excitement as waves of pleasure shot through her body. 'No Mistress PLLeaseeeeeee please it's too big I can't take it all' The protest was hopeless, Penny watched with glee as the bulge got smaller and smaller until Samantha's shorts became smooth, she had taken the plug whole.

Samantha was now at Mistress Penny's mercy, the vibrations increased and Samantha screamed for her to stop. She was helpless, her pussy started to squeeze against the plug, she was having her first pussy orgasm. Again and again she squeezed against the vibrating monster until, out of her mind with lust, she collapsed to the floor totally spent, crying with the joy of cumming and no longer in control of her mind or body.

Penny watched, her eyes transfixed at her slave writhing both in pain and pure sexual fulfillment..Penny's thighs glistened as her juices freely flowed from her own pussy, she ran a finger along the hot flesh until it was dripping, she smelt her own scent then pressed the fingertip onto Samantha's lips, they parted and Samantha lapped greedily. 'MMMMMmmmmm, is that nice bitch?' Before she could answer Penny switched the plug off, 'AAAAAHHHHHhhhhhh' Samantha sighed and as her wet pussy opened and the monster butt plug slowly slipped out. 'Now clean it slut' the butt plug now being forced through Samantha's lips 'Does this taste as good as Susie, or your cum?' Penny raged 'You cheating fucking bitch' Samantha gagged on the plug as she sucked and licked it clean.

'Now you know what it's like to be fucked Samantha, did you enjoy it? An exhausted Samantha nodded 'Yes Mistress' 'Now what happens after your former self fucked me?' hissed Penny, 'Oh yes. What's for dinner darling?' Penny grasped Samantha's hair pulling it hard and glaring into her eyes, 'Guess what? Time for dinner darling slut, I'll expect to be served in 45 minutes so clean yourself,get dressed and get into that kitchen.

Penny stormed off, Samantha listened as the click of heels faded, a smile came over her face for her orgasm hadn't finish and she was now pumping warm lube from her pussy, wishing it was hot cum.

Poor Samantha, read her continuing road to cross dressing heaven in Awakening Pt 04, that's if you want me to write it.