Cross-Dresser - Awakening Pt. 02

Sam froze on the stairs, how did Penny know? He slowly entered the bedroom, trying to avoid her gaze. The TV was on and Penny sat on the bed playing and replaying one clip, Sam had been caught out by their home security when he ran to the top of the stairs. The camera showed him dressed in stockings and panties with a huge dripping cock, which he was lovingly stroking.

Penny switched the TV off and turned to Sam 'So you like dressing up do you?' Sam nodded but wouldn't meet her eyes, Penny walked over and stood behind him, then taking his arms she pulls Sam's hands behind his back, 'You like the feel of silky knickers don't you?' as she guided his fingers under her tight skirt to her thighs and panties, Sam moaned softly as he felt his senses going wild at the touch and his jeans began to bulge.

Penny pushed Sam face down onto the bed, he heard Penny's heels click on the hard floor and the rustle of clothes being put on. 'You can turn around now slut'. Sam rolled over, Penny stood before him in a tight satin dress and wearing her highest heels, 'Take off those clothes and put them in here' Penny pointed to the chest at the bottom of their bed.

Naked before her Sam felt so vulnerable as she locked the chest. Smiling Penny touched Sams' still firm cock and gave it a hard squeeze causing him to yelp and pump wildly. 'Now you be a good girl and remain here until I return' Sam nodded with a meek 'Yes' He watched as Penny left the bedroom, heard her car start up and she was gone.

Why had she used the words 'good girl?' it didn't matter, he opened his drawers to find some clothes to wear, it was empty, his closet the same, every single item of male clothing was missing.

Sam's thoughts now turned to where had Penny gone. He lay back on the bed. Without thinking He reached under the bed, the bag was there, 'May as well have some fun' as he touched the satin panties. He slipped them on, arching his back and caressing his arse before fastening his suspender belt. Stockings were next, rolling them carefully up each leg and fastening them to his 'susses'. Sam sighed with contentment as he felt his cock growing and straining against the material of his panties. His eyes closed as his fingers traced the satin tent then curled around his cock, moving slowly at first he pulled back making the material even tighter then up and down, growing in intensity until he could feel his cum rising, he stopped, letting his body relax before starting again edging closer and closer, but each time denying himself the pleasure of climax but enjoying the greater pleasure of edge and deny.

Sam pleasuring himself made him forget his other senses, he never heard Penny's car arrive nor her coming up the stairs with all her shopping. The first thing he heard was Penny stamping her heel, Sam froze and let his hard cock fall from his hand. 'I wondered where you hid that costume you slut' Penny scowled at Sam's manhood, but allowed her fingers to wrap around the shaft then squeezed hard while forcing the cock under Sams' arse, Sam gasped at the pain but said nothing. Once Sam's panties were nice and smooth in front, with all hint of a bulge gone Penny sat next to him stroking his hair, 'Now that you've decided that you like wearing women's clothes I've decided to indulge your guilty pleasure, but on MY terms'

Penny reached into her shopping, 'You will wear these' laying out white panties and bra, falsies, a silky blouse, short red skirt, white pantyhose and white pumps with a 3 inch heel. 'You will present yourself to me in 10 minutes and if I find one stain on your underwear you will be punished' Penny picked up her remaining shopping and left Sam alone in the bedroom. Sam's mind was racing, did she really want me to dress as a female? What was going through her mind? He quickly removed his black panties and stockings.

Taking a tissue he carefully wiped precum from his cock, he slipped on his new panties and pantyhose, the feel of them causing him to pump once more so he quickly tucked his now soft cock away making himself more presentable. Sam struggled with the bra, he was used to taking them off Penny not wearing one, but he eventually had it right and slid in the falsies Penny had provided giving Sam a nice bust which was firm to the touch, more twitching from his cock, He put on the blouse, skirt and shoes before looking at himself in the mirror, he couldn't believe how he looked and began moving his hands from his false titties to his crotch 'OOOhhhhh'

'Your 10 minutes are up' Penny's voice brought Sam back down to earth, he tottered towards the door, obviously high heels needed to be mastered, slowly he went downstairs and into the lounge, Penny sat on the couch, Sam couldn't believe his eyes, she sat wearing a red leather dress with black trim, a spiked collar, long red PVC gloves and red knee length boots with a spiked heel. She looked him up and down, 'Hmmm somethings missing' as she reached behind and produced a short blond wig which she offered to Sam.

He put the wig over his dark hair, now he was Penny's blond slut, Penny laid out rules 'Your name is now Samantha, you will not pleasure yourself without my express permission, and, for now, you will wear these when you leave the house' producing womens' trousers and jeans, a selection of blouses and a pack of white knickers. 'You will find your shoes in the hall', Samantha looked and saw a pair of low heeled ankle boots. I will inspect your panties & bedding daily for cum stains, and now your first lesson is learning to walk in your heels'

Penny watched as Samantha tottered around the room until after two hours she had begun to walk upright. Inside Sam was in turmoil, dressed as he was driven crazy, all he wanted was to cum and a growing bulge betrayed his feelings. 'Come here' Penny barked and Samantha stood before her, Penny checked her panties, 'still smooth at the front', 'but what's this?' Penny ran her finger along the shaft and drew off strands of cum. 'Kneel down cumslut, it's time you were taught some manners.

Samantha knelt in front of Penny, the scent of the new leather filled her nostrils. Penny spread her legs wide, 'now slut kiss my pussy', Samantha licked her lips slowly as she got nearer and nearer to Penny's red leather shorts, she softly kissed Penny getting a mixture of, leather,and pussy smell. Penny sighed with each delicate kiss, her fingertips slowly stroking Samantha's neck, more kisses, longer sighs until,

'''MMMMMmphhhh', Penny thrust her leather clad pussy over Samantha's mouth 'Lick me you bitch'. Samantha worked her tongue hard against Penny but found it hard to breathe, the more Samantha struggled the harder Penny thrust, moving her hips so Samantha's tongue could lick her pussy harder still.

Samantha was now struggling to be released from Penny's embrace, realizing her slut was weakening Penny let Samantha fall to the floor gasping for breath. Penny stood over Samantha, the leather dress coming just over her boots, Penny offered her boot to Samantha, which she kissed and sucked on the heel. 'Who am I Samantha?' 'You are my Mistress' came the weak reply. Penny stepped over Samantha giving her a brief glimpse of the pleasures under her skirt, 'and don't forget that slut, your training as my lesbian bitch will start properly tomorrow so off to the spare bedroom with you and don't forget to clean your soiled panties'

With that Penny left Samantha sprawled on the floor still gasping for air. 'No I won't forget Mistress, good night' Samantha lay on her back smiling, the taste of Penny's leather clad pussy still lingering on her lips and as she went upstairs to her bedroom she found two more surprises.

Laid out on the bed was a pair of cream satin pajamas and a pale blue baby doll nightie with matching panties. Samantha picked up the baby doll 'Good choice slut' Samantha turned towards the voice of her Mistress, Penny stood in the doorway wearing a matching baby doll, 'Thank you Mistress', and with that Penny closed the door and Samantha heard a soft 'click' as it was locked.

'What is to become of me?' Samantha thought as she undressed from her skirt, blouse. soiled white undies and hose. Samantha went into the en-suite and washed her panties and hose before slipping into the baby doll and curling up in her own bed Samantha felt content being dressed as she was, but still wondered about tomorrows bitch training and what it would bring.