Jessica and Tom 02: Meeting Up

She circled back to between his legs and giggled "My Tom you do have quite the collection of jizz leaking from you at the moment. I popped a bowl underneath you so we don't miss a drop." She slipped her hand out of sight and raised a wide stainless steel kidney bowl which ran with white fluid as she tilted it demonstrating his exploits. "You see I don't even need to stimulate you. The e-stim will slowly just milk all your cum from your balls and there's nothing you can do about it. The best part is you won't actually cum and I can hold you on the edge of ecstasy all night if I wanted to." She turned down the current to a minimum and herd Tom groan as he relaxed.

"How do you feel about eating your own cum Tom? Be honest."

"I don't like it Miss Jessica, its not nice."

"And yet you men think its ok to want women to eat your hot load? Do you not think its only fair you clean up your own mess?"

"Yes Miss Jessica."

"Yes you expect women to eat cum or yes you should clean up your mess?"

"I should clean up my mess Miss Jessica."

"Good boy but at the moment I think you likely would balk if I offered you up this white creamy buffet unless I compelled you to do so"

"No Miss Jessica, I'll try."

"Like we said before, do or do not, there is no try" she grinned "but you wouldn't remember that" she chuckled at his discomfort. "You see Tom you've been eating your own jizz for weeks if not months. It was one of the first things I had you do. Every time you jerked off you've been hungrily licking up all your man fat and slurping it down like a real cum slut but you just cant recall. Every time I've woken you up with a cock in your mouth you've been kinda committed to take the load so today we'll work on conditioning you to like the taste of your own fluids."

"Yes Miss Jessica I'll be good, I'll do it." he whimpered, still weakly grinding his hips in time with the electrical pulses despite them being turned to minimum.

She began to turn the pulses back up in intensity and he began to writhe in time with the pulses straining against the leather straps that held him firmly in place. "Oh yes its all flowing nicely down here now, you're dripping like a tap and your cock is so hard in its little prison, I guess that must be a bit uncomfortable?"

"Mmmmmmm." he moaned, it was all he could manage with the intensity she had set on the box. She had found the perfect setting. His cock dripped with every thrust and white salty cum flowed with each twitch into the kidney bowl. She kissed the inside of his thighs leaving a burgundy lip print on each, licking his sensitive areas around his panty line, teasing him more and more, knowing he was on the edge of orgasm, just where she wanted him.

After 15 minutes of teasing and stimulation the flow of cum began to slow and she recognised the signs of his balls becoming empty. His moans were more frantic as he desperately searched for release. She enjoyed every moment of his torment.

Another 5 minutes and she turned the box off stopping his stimulation, no drips had come for a while now, he was totally empty, and from that she could torment him even more.

Taking the kidney bowl with her she sauntered back to his side, his wide eyes following her as she went. She reached placed the bowl of cum on the table next to his head and then went into the drawers of the wheeled cabinet. He wrinkled his nose at the drifting aroma of his own cum so close to his nose.

"Open your mouth Tom."

"Why." He barely finished the word before he was arching his back, the pain washed over him as she pressed the quick shock button on the control box.

"We talked about this Tom!" She said firmly, "obedience is rewarded, disobedience is punished." His mouth was open anyway as he yelped from the shock so she slipped the ring gag into his mouth and quickly buckled it behind his head.

The strong metal ring prevented him from closing his mouth and with it tightly fastened behind his head he couldn't expel it with his tongue. "There, much better."

Taking a small funnel from the drawer she slipped the thin end inside the ring gag, the wide end facing up. She slowly poured a small amount of cum into the funnel and watched it dribble into his waiting mouth. His face screwed up in disgust but he couldn't prevent the salty liquid slipping over his tongue and into the back of his mouth mixing with the now pooling spit caused by the gag. He simply had no choice but to swallow. With each swallow she tipped another small measure of cum into the funnel until it was all gone.

"Good boy Tom, you see, once you've swallowed a few times its not so bad is it" The tears from his eyes made his mascara run more and she kissed him tenderly on the cheek. You've been such a good boy."

She slipped the funnel out of his open mouth and removed the gag then began to remove the straps and allowed him to move as she tenderly stroked his arms and cheeks whispering her delight in his submissiveness and how good a slave he had been.

"Why don't you go to the dresser and see if you can fix your makeup, I think you might need a few minutes" Tom slipped from the table and teetered, weak kneed to the dresser and began using the wipes to get rid of the worst of the smearing. His world was spinning with what had just happened but his arousal remained and his cock bulged in the silicone prison unable to get fully erect despite the punishment he had just received and knowing the experience wasn't over yet if she was asking him to fix his face.

He did his best to touch up the areas of his face that had run the most, reapplying foundation and blending bronzer over his cheeks. He reapplied his violet lipstick and gloss and checked his appearance in the mirror. Passable but he really did look like a $10 whore now, only a full removal and reapplication would get rid of all the smears and runs.

Jessica sat and watched as he clumsily tried to repair his face giggling to herself but happy that he was at least trying and even without Candi's help.

"Are you done my sweet?" She said as she stood closely behind him

"I think so Miss Jessica, I hope its ok."

"Its not perfect sweetie but we have to start somewhere." taking his hand she led him to the other side of the room where she placed his hand on the strange S shaped bench he had seen earlier. "This is my fucking bench Tom I can't wait to use it. Put your knees here and here" She used the crop to point "Then lean forward here" she tapped the soft leather top that was angled slightly downwards.

Tom knelt as instructed feeling the hard metal plug move in his ass as he positioned himself then bent forward, his cock slipped thought the gap between the leg supports and he let his weight rest solely on the bench, he was surprised at how comfortable it was. The mirrored walls allowed him a good view as Jessica began to fasten the multitude of straps and his arousal only grew as he felt the sweet sensation of submission wash over him as his bonds were tightened once again.

Held tightly in place he could now only move his arms but she would soon see to that. She slipped a thick soft leather cuff over each wrist and used the clips to fasten the cuff to the eyelets on the legs of the bench. The cuffs were too wide for him to get an angle on the small clips so he couldn't free himself that way. A further strap over each bicep completed his immobilisation.

He felt her tug at his ass and the unfamiliar sensation of the plug moving in his ass took him by surprise as she removed it with a slight pop, he sighed. Next she unlocked his cock cage and removed it allowing him to get fully hard for the first time today, the sensation of release and freedom was almost orgasmic on its own.

In the mirror he saw her step into a harness and watched as she slipped the rubber cock inside the harness into her snatch before she fastened the leather straps around her waist. Going to the oak cabinet she took her time searching for just the right implement before closing the door to reveal her hands holding a lifelike 8 inch cock. She un-popped the metal ring on the front of the harness and placed the dildo in place before re-securing the poppers. Using a healthy amount of lube she slid her hand up and down the shaft of the phallus slowly, making sure he was watching every moment of her show. "I'm going to slip this dick into your tight little ass and make sweet love to you my dear Tom and there's not a whole lot you can do about it. You see now your balls are empty and you still haven't cum you'll be very aroused and the slow sensual fucking I'm going to give you is going to drive you nuts."

Tom shivered in anticipation as she approached him. He felt the cold wet dick press against his rosebud and his sphincter gave easily having been stretched already by the butt plug. The dick slipped into him and he moaned deeply as it rippled over his prostate.

Jessica moaned too as she pressed the dick into his wanton ass, the other end of the harness pressed the dildo inside her deeper into her pussy rubbing against her G spot. She slowly thrust in and out allowing her desire to build with the rubber dick inside her hitting her spot perfectly.

Tom pressed against the dick as much as he could being strapped to the bench. He got into a rhythm his desire for relief outstripping the discomfort of being fucked in his ass. His moans became cries as the thrusting quickened both building quickly to orgasm.

As she reached her peak she was ramming the dick into his ass easily relishing his cries of delight as she rode him. It wasn't long before she exploded and felt her juices gently dripping down her legs as she squirted down the dildo inside her.

Leaving herself buried in his ass she reached around the leg supports and grasped his dick. Still slick with lube she began to rub up and down his shaft knowing he couldn't or wouldn't cum without his trigger. His moans were long and deep, sweat glistening on his exposed skin. "Candi gets to cum."

Tom bucked and strained against the restraints as he felt his release trigger. His cock throbbed and pulsed wildly but not a drop of cum remained, his orgasm was intense and almost unending as his body fought with the inability to ejaculate while his trigger compelled his fall over the edge into delicious orgasm.

Once she sensed his orgasm had relented she slipped her dong from his hungry ass "Aren't dry orgasms fun, you didn't know what to do with yourself did you?" Tom panted in place, speechless or unable to speak she couldn't decide which. She slipped the harness off and let it fall to the floor shivering in ecstasy as she felt every rib of the dildo slip from her slick labia.

She walked to the front of the bench watched his bamboozled face trying to comprehend the explosion of pleasure he had just experienced. She slipped her butt onto the bench in front of him his nose touching her soft hot slit, she slid her pussy onto his waiting mouth and commanded "Lick me slut!". He had no option but comply, the second part of his orgasm trigger making him a mindless automaton whose only desire was to obey. She squealed in delight as her third orgasm washed over her and her cum sprayed onto his already ruined face making his makeup run one final time.

Preparing for an outing

It took Tom two days to recover from the events in the play room. His mind had been truly blown. He had never known that a dry orgasm combined with a hypnotic trigger could cause such an explosive reaction. He had obeyed the rules of the agreement and dressed as a sissy but they had not played the day after. Jessica occasionally teased him with photos on her phone that had been captured by the cameras in the playroom. She particularly liked the one of his ruined face taken when she commanded his orgasm on the bench.

This morning Tom had arrived downstairs with his makeup done in subtle shades of plum, his wig now a copper red with plaits and sporting a short pleated schoolgirl skirt. His legs were in nude holdups and his black bra could easily be seen through the thin white blouse. Jessica enjoyed his choices, she did like him tarty and she wondered if he was wearing panties under there or not. "Good morning my sweet, don't you look good enough to eat today."

Tom curtseyed and gave her a twirl the skirt rising up as he spun allowing her to see his black silicone chastity device, no was the answer to that then. 'He's obviously playful today'.

"We need to go out today Tom, to get you a new outfit for a party we'll be attending on Friday." Toms face dropped, how could he go out in this outfit.

"I should change, he stammered"

"Oh no sweetie, you chose it, you get to wear it, it'll do you good to see what you do to the men folk. They won't even know you have a cock under that skirt." She mused "Besides we need to leave shortly so no time to change. Grab your bag and lets go." Tom grabbed a slice of toast from the counter then trotted upstairs to grab his bag as he had been told.

The black limo sat idling on the curb side as the came out of the house. The driver held the door open for Jessica then opened the other side for Tom ensuring he was on the street in full view long enough to get some stares from the passers by. He danced awkwardly on the spot before eagerly climbing into the car and his eyes glassing over as the leather seats hugged him into somnolence.

The drive took about 30 minutes and while Tom languished in his little daydream Jessica casually stroked his thigh knowing that when she woke him he would instantly feel the discomfort of his restrained erection.

The car pulled up at the curb and the driver opened the door for Tom first "Shake a leg sweetie, we're here" lurching back to reality Tom adjusted his skirt to try to cover his stocking tops and made a vain attempt to adjust his groin into some kind of comfort, both battles he would never win. He slipped along the leather seat and emerged into the bright sunlight right in front of the mall's main door.

He was instantly self conscious the deep blush spread instantly across his face. People stared at him as he stood waiting for Jessica to join him. Passing men slyly checking out his pert ass while women sneered at his tarty outfit.

"Come on then, just a few things to get here before we go to a more boutique place." Jess took his hand and guided him into the mall. She was pleased to see he was more comfortable walking in his heels now, he looked more natural rather than the clomping guy walk he had been previously. Practice makes perfect! She'd only chosen the mall to see if he would balk at a public appearance as Tom rather than the ever keen Candi.

They made a bee line for the large anchor department store, conveniently at the other end of the mall. Jessica made a point of stopping regularly to look in various windows at this cute dress or that adorable swim suit. Each time she knew Tom was being gawped at and she knew his self consciousness would be overflowing. At one such stop, a wolf whistle was heard from a passing group of college kids, even respectable gentlemen grinned and took time to drink in his slutty attire, imagining what it would be like to have a night alone with such a wanton creature.

"All these men are checking you out Tom, they think you are a real girl, isn't that divine. I bet you could have your pick and they'd gladly enjoy a blowjob from you in the toilets." she teased. Toms cheeks were glowing the kind of beetroot that even his liberally applied makeup couldn't cover.

As they entered the department store the familiar melange of perfume hit them, the bright lights and garish colours of the myriad of cosmetic and perfume stands dazzled the mind, just as intended.

"Now sweetie we need to find you a nice new red lipstick for the party, it has to be a nice deep red as that's the theme for the submissives at the party. Where should we start?"

"I have no idea Miss Jessica, I'm completely lost, I've only ever bought one lipstick and that was the one I bought you."

"And lovely it is too my darling but we need to find a one especially for you, come on lets start over here." She tugged his hand towards the end of the store with all the high end brands, Chanel, Dior, Armani all had concessions next to each other. The women who staffed each desk were all stunning and perfectly turned out, their makeup, hair and outfits were immaculate. Some were overtly feminine, preferring floral shades and floaty dresses whereas some were all business with harsh reds and business suits.

Jessica approached each concession and the pair were treated like royalty. Testers were proffered and demonstrated on the back of the hand before favourites were tried on by both Tom and Jessica. By the third concession Tom had begun to relax into it, forgetting his self consciousness all together as he enjoyed the fuss and attention. Not once did he feel he had been found out, or if he had, the ladies weren't making it obvious.

After an hour of to'ing and fro'ing, deciding if this shade is too blue a red or this too orange they finally settled on a glorious deep shade called Bonheur from Dior in a matte finish. Jessica said it would last longer and he would need it to be hard wearing for what she had planned. That comment had raised an eyebrow from the saleswoman as she was placing it in a reassuringly expensive looking Dior bag. Jessica whispered in his ear "$60 for a lipstick, how many cocks will you need to suck to pay for that I wonder?" Tom's blush returned as Jessica swiped her card and the saleswoman handed her the receipt.

"Come on sweetie, we have an appointment for your dress fitting in about 30 minutes, the car should be just outside." She said looking at her phone. They quickly navigated their way back to the store entrance and to the adjacent mall exit that Jessica had chosen not to use earlier and into the waiting limo.

The drive took a little over 20 minutes and they pulled up outside a very trendy looking parade of shops in the warehouse district. The shops had everything from vintage lingerie to expensive antiques all sporting ancient plate glass windows with ornate sign writing and heavy wooden doors with extravagant brass handles.

The car was parked in front of a much more subtle storefront. Rich silk hung in ripples down the double fronted window display pooling at the floor and appearing to run into ripples across the display area floor. Two mannequins stood clad in tight rubber outfits, one in each window hinting at the delights within.

"Shake a leg Tom, its time to try on a dress or two." She hopped out of the card after him and lead him to the door of the expensive looking store. A bell was rung and the door buzzed open and they entered. The store smelled slightly chemically, a mix of solvents and a heavy perfume Tom couldn't quite identify. There were only a few racks of clothing on each side of the small store and a central area showed off more of the rubber outfits on four full body mannequins. Ornate lilies sat in large vases intermingled with the inanimate models tempering the dark sinister looking black and red shiny outfits.

"Ladies, welcome to Fetish, Miss Jessica, how lovely to see you again." the sales woman was statuesque, standing at over 6 feet in her porn star heels, she was clad entirely in rubber. Her tight metallic purple pencil dress was extravagantly laced all the way up to her waist where it gave way to an over bust black bustier. The outfit finished with a black bolero jacket. She appeared to be in her late 40's but she was stunning. Her makeup was all business, fine winged eyeliner and light eyeshadow with a hint of blush and a shock of crimson lipstick gave her the class of a 50's pinup. She left Tom speechless.

Jessica returned the air kisses and the two embraced. "A pleasure to be back Miss Janice, This is Candi, the one we spoke about on the phone. Well he's Tom at the moment but Candi is in there somewhere." She squeezed Toms ass under his indecently short skirt.