Jessica and Tom 02: Meeting Up

He hung the dress on the clasp of the sash window next to the dresser knowing that he'd need to match the colour to get the look just right. He sat eagerly at the dresser and began his routine with concealer over his eyes and cheeks then blended it to create an even base for what he hoped would be dramatic eyes. Hoping for a sharp line of colour he slipped on some tape at an angle at the outer edge of his eyes to provide a mask before starting to add colour.

He found a colour that was close to the purple silk in the corset and another shade that closely matched the hue the lace took when it overlaid the silk. He carefully lined the crease with the dark kohl grey before carefully blending and softening its lines. Then taking the deep raspberry purple he packed the powder into his outer lids and again blended the colour to diffuse it into a smokey effect just like Miss Sarah had taught him.

Next he needed some sparkle so took a shimmery light pink shadows and placed it into his inner lid and blended it with the grey and purple before finally highlighting his tear ducks with a bright glittering cream. Carefully he drew in his eyeline with a dark kohl pencil and carefully smudged it to keep with his sultry smokey look. After repeating the process for the other eye. Once he was satisfied he slowly removed the tape and smiled broadly at the clean line of colour he'd managed to create. Adding a smudged line of the deep purple under his lower lid added to the drama.

He found the foundation that Miss Sarah had said best suited him and applied it liberally over his face before adding his contours and highlights. Tarty meant being over the top on colours so he chose and overly dark grey contour shade then highlighted with a glittery metallic highlighter before adding a hint of pink blush to give some colour back to his flawless cheeks.

Saving his favourite for last he slipped the soft applicator from a vivid violet lip stain and applied it to his lips. Once sure it had dried sufficiently he used an equally delicious purple gloss to really scream wanton slut.

He slipped his platinum blond wig onto his head and coiffed the flowing locks into place trying not to get the fine strands too stuck to his sticky lips.

Stockings were next to be rolled onto his smooth legs, he fussed with the lace tops to get the seems perfectly straight before he fastened the fat garter straps which hung from the black lacey belt that now gently cinched his waist. Once his stockings were perfect he slipped a pair of black satin french knickers on before delving into the shoe closet.

A pair of stiletto ankle boots were the order of the day. Their patent leather spoke to his inner harlot as did the 4 inch spiked heel that he knew would enhance his shapely legs. Finally he needed to slip into the dress which would be easier said than done since corsets so far had been a two person job.

He carefully unclipped the metal clasps at the front and loosened the lacing down the back. Once he was happy with the rough size of the lacing he tied it off before he stepped into the open dress and slipped it up his body. It was snug, very snug, as he wriggled into place and fastened the metal clips up the front. He felt the air being squeezed out of him at the expense of a perfect figure. He sat uncomfortably on the dressers seat and admired his handy work as he gasped slightly from the effort. Something was missing.

The lightbulb came on, he delved into the box and found a pair of over the top feathered false lashes. Carefully he applied the glue to his lash line before using his tweezers to position them just right. Finally he applied a thick coat of mascara once the glue was set and batted his eyes in the mirror marveling at his work. Miss Sarah really was a splendid teacher.

He clip clopped his way carefully onto the landing getting used to the ridiculously high heels he had chosen, the taffeta and lace skirts swishing and swaying as he walked. The stairs would be a challenge until his feet got used to the angle the world was now at. Gingerly he used the warm oak balustrade to teeter down the stairs to meet Miss Jessica.

Jessica relished the cautious steps she heard on the wooden stairs as Candi made his grand entrance. Dressed to kill in an above the knee black skin tight skirt and white blouse her consuming gaze washed over him drinking in the possibilities of this violet burlesque sissy that stood before her. She looked every inch the strict school principle down to the slick tight pony tail and large horn-rimed spectacles that she wore for effect. In her hand she held a vicious looking leather riding crop which she took pleasure in tapping on the inside of her other hand as she approached him.

She circled him like a lioness circling her prey licking her burgundy lips as she took in his work. As she approached his rear she slipped the crop onto his bare thigh and used it to raise the explosion of taffeta and lace below his waist to reveal his panties and garters. She traced the tip of the crop around his thigh as she completed her circuit and slipped it under his balls and tapped the chastity cage just hard enough to get his attention.

"Well Candi you have gone all out haven't you. I've always wanted my very own saloon girl. I wonder how much we could make whoring you out to the local gentlemen of the area in that getup?" Slipping the crop away from his groin she led on to the basement door. "Follow me sweetie, we have a lot of work to do."

Candi teetered on his heels as he tried to follow at the same pace. As much as she had enjoyed his outfit Candi felt his loins stir as his eyes slipped over her pert buttocks in that glorious skirt that was so tight he could see her lingerie beneath.

Jessica slipped easily onto her ornate throne at the foot of the bed. She crossed her legs knowing that would cause the skirt to ride up enough to give her submissive an eyeful of her lingerie. Candi followed slowly, still trying to master the overly tall heels he had chosen. What he lacked in deportment he made up for in ambition and enthusiasm she thought to herself.

She pointed to the large soft cushions at her feet "Kneel Candi, your rightful place is at my feet so whenever we come into this glorious place you will come to the foot of my throne and kneel." Candi flopped to his knees, a rather ungraceful descent, having obviously lost his balance on the way down. He adjusted his blonde locks and knelt proudly at her feet gazing up at her with desire.

"As you have seen there are many interesting things to play with down here. Some inflict pain, some restrain, some humiliation but they have one thing in common, they are all for my pleasure." she idly stroked the soft leather arm of her throne. "When you are here in this place, you are no different, here for my pleasure so you understand Candi?"

"Always Miss Jessica, I can't wait to pleasure you."

"And what about our manly man, do you understand Tom?"

Tom slipped back into control of his body. The sensations of his restricted breathing, painful feet, soft sensual lingerie and heavy makeup all hitting him at the same time and it was almost over whelming "I um er, I guess."

"You guess 'what' Tom?"

"I guess I'm here to serve you?" he said meekly

She rolled her eyes as she exhaled heavily and picked up the cane and swatted his leg enough to make him yelp "your servitude is not in doubt, look at yourself all tarted up like a saloon girl whore!" She pointed to a mirror on the wall so he could realise his current status "The fact that not only did you dress yourself but that you chose to wear this outfit only underlines your inner desires to submit."

Tom gawped as she spoke, he looked hot, like a real pornstar about to get into some really hardcore action "I did this?"

"Of course Tom, well your sissy alter ego did but its all you ultimately. You needed a helping hand so I let her off the leash for the morning to see what she would come up with. I'm very pleasantly surprised. The gentlemen callers I know would have a field day with you dressed like that. I can see them jamming their hard cocks into your mouth and cumming all over your perfect face melting that perfect makeup. Or perhaps they'll flip up that devilishly short skirt and pound you tight little ass till your hole is dripping with man fat."

She fanned herself with her hand mockingly "The ideas are getting me all hot and bothered but that's not what I was getting at. How should you address your Mistress?"

"Mistress or Miss Jessica" he obediently replied

"Good, so would you like to adjust your response or do I have to persuade you further?"

"I am here to serve you Miss Jessica."

"Excellent Tom, I Think I'll keep you in play, Candi is a darling but tormenting you is far more fun." She leant forward and tapped his imprisoned cock before playfully running the tip of the crop down his thighs. "What to do first I wonder, so much choice but we should start slowly." She opened the drawer in the arm of her throne and pulled out a thin leather collar emblazoned in diamonte's with the word SLUT admired it briefly then slipped it round his neck and fastened the buckle. "Every slave needs his collar and it does so set off your outfit."

"I think we'd best start getting you fitted out for training" she slipped out of the throne and walked to his left and wheeled back the black latex medical screens that hid the darkly threatening devices behind. "Come on sweetie pop your pretty butt on the chair" she pointed at the gynaecologist chair. Tom hesitated, dread creeping in realising he had agreed to pretty much do anything for the next 2 weeks and she was starting strong.

"Tom, be an obedient submissive and come and sit in the chair." he felt himself move without thinking and tottering on the heels across to where she indicated. Once he sat she swung his legs up and over into the stirrups and and began to fasten the myriad of leather straps. "Can't have you fidgeting." she chirped as buckles jingled and leather creaked around his upper and lower legs. She reclined the back of the chair flat and slipped a thick leather strap over his waist and another over his chest further restricting his breathing.

"As you were sweetie, there doesn't it feel so nice to be completely restrained?" she quipped releasing him from his obedience as she secured his arms to the swing out leather pads at his side and finally placing a thick leather strap around his neck and buckling it in place. Almost instinctively Tom struggled against the restraints but soon realised with so many he had no chance of getting free.

Completely immobile his breathing quickened, she sat on the stool next to him looking through the large glasses which made her exquisitely made-up eyes larger to him. She watched him try to wriggle against the restraints enjoying his helplessness "Just how I like my slaves, helpless."

She pulled a wheeled cart to the side of the table and opened a drawer. From it she found some black rubber gloves, a set of cables, a bottle of clear liquid and a polished metal buttplug. The neck restraint allowed him to turn his head a little so he could see what she was doing. She pulled on the black rubber gloves making sure he could see her tugging and stretching them as she made sure they were perfectly fitted. Next the butt-plug was lubed with the clear liquid and placed on top of the cabinet. Then she arranged the wires she had got out into some order only she knew before she wheeled her stool to the foot of the table dragging the cabinet with her.

Loosening the stirrups she slid them apart allowing her access to his intimate areas without protest. She secured them once his legs were in the correct position to stop him trying to close them. Pressing a button she raised the back of the table so he was no longer flat and could watch at least some of what she was doing. A deep sigh came from her "What slut puts panties on?" She exclaimed.

"I didn't know if I should or not Miss Jessica."

"When I say slutty or tarty, I mean ready to serve at any moment, panties do get in the way!" She opened the drawer and theatrically produced a pair of scissors. Tom's heart skipped a beat as he felt the sharp cold steal slip along his skin and start to cut until he realised only the panties were being cut from him. "There, much better although it does gaul me to ruin a lovely pair of panties."

She added a generous blob of lube to her fingers and slipped them between his buttocks "you'll just feel a cold sensation and some pressure" She said jovially as she slipped two fingers into his tight ass. The lube allowed her to slip easily into him and quickly found his p-spot. He groaned in pleasure as she pressed it gently before slipping the out again. "Now for the main event."

Once again she lubed the butt plug and placed the tip against his hole. He felt the cold tip against his ass and the small pressure combined with the slick lubrication pushed him open allowing the plug to slip into him. He felt himself clench instinctively and the pressure eased slightly as she allowed his spasm to pass but soon it resumed and inch by inch the plug slipped into him until it reached its inward curve at which point his ass hungrily closed around it.

"There that wasn't so bad was it?"

"No Miss Jessica." he managed to whimper as he felt the cold plug slip into place on his prostate and his sphincter muscles adjusted to the intruding phallus. She smiled broadly her, plum coloured lips glimmering in the bright light shining from the suspended surgical light. as she continued to fuss around his ass and cock just out of his sight. He felt some tugging around the chastity cage followed by the cool sensation of liquid being dribbled into the device. She then grabbed the cage and twisted it as few times before letting it settle back between his legs. He felt a small tug on his garter belt as if something had been hung from it but what that could be he had no idea although he guessed he'd find out soon enough.

"All done" she chirped as she wheeled her stool back to his side. He turned his head as much a he could in the neck restraint to follow her movement. She now held a small black box in her hand which she casually waved in front of his eyes. "This is one of my favourite little toys to play with, its the very essence of bondage and dominance play" She pressed a button on the box and red glow appeared from two LED's.

"With this dial I can apply a gentle tingle to your cock and balls." she grinned as she turned the dial. Tom stiffened as he felt the unusual sensation of the tingling over his cock and into his balls. "With this one I can so the same in your ass" again she turned the dial slightly and Tom struggled against the restrains as he felt the tingle build in his ass. "Can you feel how pleasurable it could be Tom" She didn't need an answer, she could see the arousal on his pretty face and heard it in the deep moan he allowed to escape.

"If I am feeling naughty or think that you are misbehaving though I can also cause more than a tingle." She briefly turned the dial up to half way and Tom yelped as the tingle rapidly ramped up through extreme pleasure to tangible discomfort his body jerked in reaction to the sudden pain.

"Its called E-stim and this remote box means I don't have to be all tied up in wires to enforce or reward. Isn't it just a delight?" She turned the dial back to its minimum setting and watched him visibly relax. She stood and reached down to kiss him, their lipsticks slippery as they mixed and she forced her tongue into his mouth. "Delicious," she said withdrawing from the kiss. "Now don't go away." She chuckled as she stood and walked out of his view he expensive heels clicking on the hard floor as she went.

Tom struggled against the straps as he tried to follow her across the room but there was no way he could. The constant clicking of her heels served to fuel his imagination, what was she doing back there. He became more frantic shifting his body trying to get an angle. The tingles in his ass and on his cock ramped up to a more intense pleasure setting. He moaned involuntarily as he felt his arousal build as the pulses began to stimulate him.

"I didn't say you could struggle Tom but it is so divine to watch so this is your reward for entertaining me." The clicking of her shoes grew louder as she returned into view. The white blouse and tight black skirt gone now, a leather corset now in place. Ornate leather straps and silver stainless steel buckles adorned the front of the shiny garment leading the eye down to her black lace panties and black lace topped sheer stockings held in place by her signature. The crop had reappeared in her hand and she used it to tease his tender inner thighs as she walked back between his legs.

"It seems its having the desired effect" She leant over and used a gloved finger to retrieve a large pearl of precum from his cock which was now pressing against its cage as he tried to get hard. "Yummy" she reached forward and presented the salty liquid close to his lips, deliberately not touching them. "Lick" she commanded

Tom hesitated again, she had expected this, all this was relatively new to him as Tom. Had she allowed Candi out to play, she wouldn't even have had to ask, his tongue would have been out before she got close, the cum slut that he was, but Tom needed some nurture. She wanted to start to apply her dominance hence the e-stim currently attached to his private parts. She used her other hand to increase the setting and he yelped as its sensation once again became uncomfortable.

"Lick" she repeated, his tongue appeared from his violet lips and sought out her finger. She held it just far enough away so only the tip could reach. She delighted as he strained to obey and lick his juice from her finger. "Good boy Tom." she dialled back the setting to allow him to recover. "You see, obedience is rewarded, disobedience is punished, its as simple as that." She reached back to his straining cock and took another scoop and presented it to him again. This time he didn't hesitate and licked it straight from her finger. "Excellent."

Tom felt the table recline so he was flat once again and the whole unit seemed to lower slightly. She strode to the top of the table towering over him as his head now lay around her thighs. She slipped a finger into the band of her panties and let them drop to the floor revealing her glistening pussy then stepped forward so his head was between her lace covered thighs. She used the controls on the side of the bed to raise the table slightly putting his nose just inside her wet pussy lips, her juices making his nose shiny before she lowered herself fully onto his face.

"I think you know what is expected Tom." She could already feel his tongue begin to explore her sex as he searched for her hot clit. She placed the control box on his chest and tweaked the controls slightly and he squirmed in response as she intensified the stimulation on his balls and prostate.

She soon began to moan and could hear he was doing the same. She could see his pelvis straining to grind against the imaginary sensations that tormented his nerves. She rode his mouth smearing his makeup with her wet snatch as she went. Her familiar trembles began and she relished the building orgasm. "Oh Tom you have such a talented tongue, it really is a treat to ride you." Her cajoling increased his enthusiasm and she felt his tongue lapping frantically at her clit, occasionally slipping deep into her hot tunnel.

Her legs shook now as her orgasm began to crest, grinding her pussy into his mouth as her climax exploded and she screamed in pleasure using her hands on his chest to support herself as her knees buckled in pleasure.

As she composed herself she stood and allowed poor Tom up for air. His makeup was destroyed, his mascara running down his cheeks and his lipstick smeared all over his face. He looked tense as he became more and more aroused, she left the e-stim doing its thing at a mid range level of pleasure. His hips bucked and ground as he tried to fuck anything he could but all he found was air.