Jayden’s desk at the insurance company was reasonably private, separated from the other booths in the office by semi-permanent dividing walls to afford him a degree of privacy for phone calls etc. At 23, he was still in a junior role. Jayden’s boyish good looks, strawberry blonde hair (now long enough for a pony tail to his manager’s distaste) and slender frame had proven quite popular amongst the younger female staff at the firm when he had first arrived. Indeed one or two had caught his eye, however his mind was often elsewhere…
His personal phone, face down on the desk, buzzed for his attention. His pulse raced. If it was whom he sincerely hoped it was, then checking at work might not be appropriate. It was unlikely anyone would stand on a chair to peer over the divider into his booth. Jayden swivelled his chair in a silent reconnaissance 360 and judged that the coast was clear. He removed his headset and checked his message.
1 new message: TickleMASTERNYC
Jayden’s palms were a little sweaty and he wondered if anyone might be able to tell how excited this message made him. Was he fidgeting? Sweating at the temples? He opened it excitedly.
‘TickleBoiToy. Your Master is horny for your ticklish feet. Go and take a picture of your soles and send it to me immediately. Wear your ankle charm. I will reward you with my cock if you are lucky.’
Jayden loosened his collar and switched his availability to away from desk to forward calls to his colleagues. Then, checking nonchalantly for prying eyes, he made his way out to the hall and down the men’s room. Once in a cubicle, he knelt on the closed toilet lid, stripped off his shoes and socks, rolled up the legs of his suit trousers and carefully clipped a slim silver chain around his right ankle. From it hung a charm engraved with the words “Property of TickleMASTERNYC”. Jayden snapped a few pics of his bare feet, posed as seductively as he could manage and ensuring the charm was visible. He sent several back to TickleMASTERNYC along with a message.
‘Here are my ticklish sissy-boi soles and toes Master. I can’t wait for tonight. Please send me your delicious hard cock. My tootsies want to stroke it.’
Jayden put his shoes and socks back on as quietly as he could, flushed and headed back to his office to turn in a Friday afternoon of distracted work answering calls for insurance claims from angry people he didn’t care about. No one got much done on Friday afternoon right?
When the end of the work day finally came around, Jayden politely declined work drinks despite the persuasiveness of some pretty female colleagues and slipped out. He headed straight from midtown to the upper east side and buzzed the intercom for the penthouse flat of a luxury apartment block overlooking the park. The buzzer was answered.
‘Hi, It’s Jay. I’m here Sir.’
‘Who is Jay?’ Jayden gulped, waited a few seconds for an elderly lady resident to get into the lift and for the doors to close, and then replied.
‘It’s your TicklBoiToy Sir.’
‘Well up you come then.’
Jaden waited for the elevator to come back down then rode it up to the top floor where his Master’s suite awaited. He was about to knock on the door but it swung open and his knock whiffed into empty space. TickleMSTERNYC, Curt to his friends, stood before him breathing heavily. Master was clearly in a rush to get the evening’s merriment underway.
Jayden knew his Master was a big guy but after a day of getting into his subby sissy obedient headspace (and sporting a raging boner all day from it), he was always intimidated by Curt’s physicality. Curt was 6’5”, fully 9 inches taller than diminutive Jayden, and a square 250lbs. He certainly wasn’t a bodybuilder, but he wasn’t tubby either, just built like a Silverado full of steak. He shaved his chin but wore a full moustache. He usually wore expensive casual chinos and loafers costing more than Jayden’s monthly salary but on this occasion, he had answered his door in just a robe.
Curt grasped Jayden firmly by one suit lapel, pulled him inside and deposited him gently against the hallway wall. He closed the door with one hand and flicked open his robe with the other allowing it to fall away from his thick cock, fully erect at 9 inches. No matter how many times Jayden “familiarised” himself with that monster cock, the first sight of it always rendered him rabbit-in-the-headlights awestruck. Curt smiled.
‘You’re so cute when your eyes go wide like that. What are you waiting for? Greet your Master properly.’
Jayden knelt before his Master and gingerly reached up his hands to gently stroke the shaft of the eager throbbing cock before him. Transfixed by it, he began licking around the tip and taking the head into his mouth as he stroked the shaft with his hands. Curt looked up at the high ceiling and growled in approval as Jayden’s delicate fingers and mouth Licked, sucked and gently tickled all over his cock making it throb all the harder. Jayden was pushed comfortably but inexorably into his fully submissive headspace by the ramrod hard cock looming over him and he willingly embraced it. He couldn’t wait to leave all traces of his masculine persona behind and submit his soft boy soles to whatever sadistic tickle tortures Curt had in store.
Curt reached down and stroked aside a lock of blonde hair which had fallen over Jay’s cheek blocking the view of the sprinkling of freckles on each blushing cheek.
‘Hello TickleBoiToy. I’ve missed you. We have all weekend.’ Jay looked up and nodded as he continued sucking. ‘However, your Master shoudn’t have to prompt you to greet him properly should he?’ Jayden gently shook his head, his mouth very much full. ‘Maybe we need to make you squeal extra loud this weekend huh? Are those cute little tootsies of your feeling ticklish?’ Jayden nodded. ‘Good.’
Curt reached down, took hold of jayden by the shoulders and forced him down to lie on the plush carpet, still only just inside the front door. Curt rolled his TickleBoiToy over on his belly and sat down straddling him, sitting on his butt and the small of his back and facing his legs. He then lifted Jayden’s feet up and quickly stripped off his shoes and socks. Jayden’s view comprised the inside of the front door and nothing else. Even though not yet tied in the bondage he knew he had to look forward to, he would have been utterly powerless to try to buck Curt off him. Curt, rolled his suit trousers up to his knees and began to half tickle half stroke Jayden’s calves, checking that his TickleBoiToy had shaven his legs as instructed. They were smooth, pale and baby soft. Curt examined the charm anklet. He held Jayden’s feet in his hands and leaned in for a long sniff of their scent, his moustache tickling Jaden’s toes. Jayden creased and fought back the giggles but Curt had noticed. A few giggles, while silent, had caused Jay to wriggle a little and Curt missed almost nothing where ticklish reactions were concerned.
‘Wow TickleBoyToi… You’re that ticklish? Just my moustache? Awwww, breaking you is going to be too easy!’
With that, Curt licked from Jayden’s right heel all the way up his soles to the toes and then stuffed all five dainty toes into his mouth at once. Jayden laughed out loud and squirmed. His fate was sealed. Curt moaned urgently as he tongue-probed the ticklish toes before him. The he grabbed the other foot and repeated the process lick-tickling every inch of both of Jayden’s feet as he giggled and squirmed about uselessly beside the shoe rack.
‘Oooooh fuck me Boi, I want you right now but I insist on the proper ceremony. You know where the changing room is. Everything you need is waiting for you. Go and get changed very quickly and then step into the playroom and offer yourself to me for tickle-torture.’
Jayden still had the salty taste of Curt’s pre cum on his lips as he hurried into the snug ground floor study Curt used as the changing room. There on the daybed was his Master’s choice of initial outfit for the evening, all laid out: A tiny white waistcoat with two buttons exposing a generous length of midriff, a pleated high-waisted grey tartan schoolgirl skirt (exceptionally short), tiny pale pink frilled ankle socks, black patent leather Mary Jane shoes (which he knew existed only for the pleasure of stripping them off in the first minute), pale pink frilled lace gloves to match the socks, tiny white panties and a black silk choker collar. All of his clothes were perfectly fitted, bought specifically for him by his adoring Master, all apart from the panties which looked wholly inadequate to contain Jayden’s excitement. There were also two elasticated hair ties with little pink bows. He quickly stripped off his suit and underwear and savoured the pleasure of getting dolled up like a girl for Master. He added the final touch using the mirror of the dresser: He braided his blonde hair into French plaits with the pink bows, one right and one left, just long enough for Master to grab. He admired himself in the mirror. He noted with excitement that the curve where his buttocks met his thighs was visible when he bent as much as a few degrees – just as Master liked.
He took a deep breath, left the room and stood in the corridor where Curt was waiting.
‘Oh, my dear little TickleBoiToy! Wow. You look just delicious. I could just tickle you silly with a feather duster right here in the corridor. Give me a twirl.’
Jayden obliged and turned 360 to show his Master how well his sissy outfit fitted him. Curt, practically drooling, allowed his robe to part and his hard cock to stand to attention pointing at the object of its desires, Jayden’s svelte young body.
‘Ok Toy. Upstairs now.’
Jayden climbed the stairs with Curt following a few steps behind, gazing up his skirt at the tiny snatch of white fabric visible at the top of his butt.
Jayden entered the Master bedroom where most of Curt’s toys and bondage gear were assembled. There was a four poster bed with various attachments for cuffs both ankle and wrist. A set of heavy ankle stocks was bolted onto the foot of the huge bed. A wooden pillory stood in one corner of the room, height adjustable naturally. A camcorder on a tripod stood facing the stocks. Along one wall was arrayed a selection of cuffs and restraints and on a dresser opposite the bed lay a devilish selection of tickle tools including assorted feathers, electric toothbrushes, banjo picks, a pair of pet grooming gloves, hairbrushes, vibrators and large tubs of both coconut oil and Vaseline. Curt watched Jayden taking it all in and smirked with predatory intent. He walked up behind and held Jayden by both arms, allowing his cock to nudge against Jayden’s mostly bare butt cheeks and to nestle into his crack and leave snail trails of pre cum.
‘Well, my little TickleBoiToy, here we are in my special tickle dungeon.’ Curt reached over and hit the record button on the camera. ‘I hope you’re feeling ticklish. You owe me a great deal of laughter. I want to make you laugh and squirm and beg until you can’t breathe. Do you submit to me as our Tickle Master boy?’
‘Yes Master!’ Jayden nodded eagerly. Curt leaned in to whisper in Jayden’s ear as his grip tightened subtly on Jayden’s arms.
‘You like it that your sexy little feet turn me on don’t you boy?’
‘Yes Master.’
‘You like teasing real men with your sexy soft ticklish sissy feet don’t you? You like making real men’s cocks hard with your cute little toes don’t you?’ Curt pushed his hips forward and his cock slipped upwards to push against the small of Jayden’s back.
‘You want it don’t you? You want my cock?’
‘Yes Master, I do want your cock.’
‘Well, your feet pics teased me a little already, but before you earn my cock I think I need the real thing. Sit on the bed and place you ankles in the central holes of the stocks.’
Jayden, guided by Curt’s strong hands on his arms, walked over to the bed and climbed on exposing his barely covered little bubble butt under his skirt. He sat down and offered his ankles to be locked in the stocks, nestling each into the padded notch and allowing Curt to drop the stocks closed with a loud ‘clack’. He offered his wrists to be cuffed behind his back and Curt obliged firmly. Curt pulled up a stool at the foot of the bed where Jayden’s gorgeous smooth size 8 feet protruded vulnerably, still in their little pink ankle socks and black Mary Janes.
‘Well don’t you just look as pretty as a picture?’ Curt said it largely to himself as he settled in and started to savour the ritual of slowly unbuckling Jayden’s little black shoes one by one. He stared regularly into Jayden’s eyes transmitting his predatory energy and making Jayden’s pulse race, making him both genuinely apprehensive and excited about how ticklish his feet were and the ordeal they were about to be put through.
‘What’s in here? What’s in this cute little shoe huh? Aww, is it a little wiggly tootsie in a pretty pink sock? Awww and it can’t go anywhere… Oooooh coochie coochie coo little tootsie.’
Curt, speaking again mostly to himself, gave Jayden’s right foot a few seconds of very light tickling through his sock. Jayden creased up, closed his eyes and curled his toes over, trying and failing to hold in the giggles. Curt watched his reactions, drinking them in like fuel, before starting to unbuckle the second shoe. He gave the left foot a similar light tickling and Jayden shook his head and began giggling silently, punctuated with shrill yelps of ticklishness, surprising even himself at their girly pitch.
‘Awww, is somebody tick-a-lish? Yes, I think so? Huh little TickleBoiToy? Aare your cute little tootsies ticklish?’
‘YES… MMMMM… OH crap oh crap OOOHOHO…!’ Jayden hyperventilated to try to get enough breath to provide the full answer he knew his Master demanded. ‘YES MASTER… They ARE TICKlish oh my god OH MY GOD EEEEEP!’ EHEHEEE!’ The tickling rendered his voice unreliable, seesawing between his own wobbly but recognisable register and loud panicked squeaking. Curt was as vocal as ever with his teasing, all of which made the tickle-humiliation even hornier for Jayden whose own cock had long since escaped its tiny whites and now stood visibly to attention betraying how much he secretly loved to be sissified and tickle tortured on his soft boy feet.
‘Ooooooh yes they are, yes they certainly are! And that’s with the cute little pink sockies still on. How’s about we peel off those little sockies huh?’
Curt began unrolling the socks of both of Jayden’s feet from the ankles, tickling as he went, until finally he had rolled socks covering just the toes. He held onto the left and tickled the bare arch beneath allowing the foot to involuntarily wiggle itself free. Curt repeated the process with the right foot and then straightened out the socks and draped the carefully over each side of the stocks where Jayden could see them. Then he sat back a little and took in the beauty of Jayden’s young bare soles and his vulnerable slender toes just begging to be tickled. The playful smile dropped from his face for a moment as the true predator took hold.
He reached his hands out and began stroking and tickling and tweaking at Jayden’s captive feet, enjoying them and harassing them with light darting unpredictable tickles. He was breathing heavily and his smile had not returned.
‘So soft…’ Curt mumbled to himself.
Jayden continued laughing and yelping and squealing and trying to catch his breath, the unpredictable attacks almost worse than sustained tickling. He looked at his Master’s face but Curt looked only at his feet now, absorbed.
Curt picked up the pace and began tickling the arches of both feet causing Jayden to try to curl his toes over and point his soles to the ground. This didn’t help of course, save possibly to be so adorable that Curt throbbed closer to a hands-free orgasm.
Abruptly Curt stopped.
‘Point your toes up.’ Curt spoke the order bluntly. Jayden obliged, stretching his soles out taut, arches down and toes up, accentuating the curve of the ball of his foot.
‘Spread the toes.’ Curt pulled the camera tripod a little closer as Jayden spread his toes exposing the super ticklish spots in between.
‘Wiggle the toes.’ Jayden wiggled.
‘Say “I’m a little slutty foot tease and I deserve to be tickle tortured”.’ Jayden repeated the phrase.
‘Say it again while wiggling the toes.’
‘I’m a little slutty foot tease and I deserve to be tickle tortured,’ said Jayden, humiliation causing his voice to stumble over the words. Curt stroked his cock a little, his need becoming more urgent. He stood up and hurriedly retrieved two long feathers from the dresser arsenal.
‘Hold the toes still and spread. I want to film your reaction to feathers being dragged slowly between your toes. If you clench your toes up, I will make you suffer more. Understand?’
‘Yes Master.’
Curt worked the feathers in between the outermost toes of both of Jayden’s feet. Jayden giggled and wiggled his feet.
‘I warned you boy.’
‘I’m sorry Master, I couldn’t help it!’
‘I want to get this on tape. I want to watch your face contorting with ticklish concentration as you try to hold still. You get one more chance.’
Curt once again threaded the feathers in between Jayden’s toes. Jayden, a little better prepared for it now, began a torrent of loud non-stop giggles but managed to keep his trembling shaking feet semi-still and his toes spread. The rest of his body channelled the reactions he had to let out somewhere and he fell backwards onto the bed, lying to one side with his cuffed arms under him, clawing at the duvet and making an assortment of delightful ‘yips’ and moans and giggles. With his eyes closed there were only the sensations of the feathers between his unbearably sensitive toes, the sounds of his own giggles and squeaks and, if he listened carefully, the animalistic breathing and bass grunts of his Master’s pleasure. Jayden had to admit that concurrently with the panicky torture flavour of the tickles, the sensations also felt divine. The two mutually exclusive reactions stormed around each other like oil and water creating a paradox of tickle-pleasure he couldn’t have explained if he’d tried. He physiologically needed to get his poor toes away but psychologically needed them to be tickled. His opposed urges did have one thing in common though: They both served to drive him senseless with lust. His cock was throbbing, in need of release. He tried desperately to restrict the movement of his toes to mere trembling, not full wiggling, struggling to keep them fully available for his Master’s enjoyment.
The feathers went from the pinkie toes, to the next toes, to the next soft little toe crease, then finally the last where they swirled a maddening little dance around his big toes before heading out towards the pinkie toes again.
Much more of the delicious torment of the feathers on his toes and Jayden was in danger of spraying much as, unbeknownst to him, his Master was from the lust of tickling his toes. Jayden opened his eyes and looked down the bed through eyes filled with tears of laughter. He was too weak from laughter to get back to seated position. He couldn’t make out his own feet from lying on the bed, only the unyielding wood of the stocks where his shaven legs passed through. The stocks were tall and sturdy and obscured his feet from his sight entirely. Everything below his ankle had been surrendered into some other realm of super masculine tickle monsters. He had no way of knowing what was being done to his feet other by feeling it as it happened. He couldn’t even make out much of Curt, only the top of his head and his wide shoulders hunched over, completely absorbed in the task at hand.
‘Oooooh God…’ growled Curt as he dropped the feathers to the floor and sent his fingertips diving under the toes and then skittering south to the arches. Jayden’s feet reacted immediately to the new attack and wiggled for all they were worth, no longer able to keep still for the tantalising soft feather tickles. Curt was too lost in tickle lust now not to dig in looking for screams from his young lee.
Jayden’s sexy soft feet wiggled and curled over wrinkling the soles, then stretched spreading the toes, then alternately one up and the other down as Curt varied his attack, his fingers exploring precisely wherever they pleased over Jayden’s ticklish feet.
Jayden’s mind was in turmoil. His eyes were closed. His little bubble-butt was clenched tightly, and his options quickly narrowing to one: To cum just from the tickling of his feet. It was as he was hyperventilating through that thought that Curt leaned over and French kissed his left foot. Curt’s fingers carried on tickling the right but all five petite toes of the slender left disappeared into Curt’s mouth to be feasted on and thoroughly tongued.
Jayden arched his back and came immediately sending a jet of cum up into the air to splatter back down over his toned belly and white button vest. Curt looked up over the stocks with a raised eyebrow.
‘Oh really? TickleBoiToy likes getting his toes sucked huh? I didn’t give you permission though…’
‘I’m… Sorry… Master… I couldn’t… help it…’
‘No, I see that. Well, I’ll reduce your punishment from 5 minutes to 2 then.’
Curt retrieved a stopwatch, a grooming glove and a bottle of baby oil from the dresser. He oiled Jayden’s feet causing him to moan in pleasure, slipped on the glove and then administered 2 carefully timed minutes of unbearable post-orgasm foot tickling with the scratchy grooming mitt. Jayden squealed and cried and bucked in genuine distress and Curt adhered strictly to the timer, watching the suffering of his darling pigtailed sissy tickle boy until the last second elapsed. Then he climbed onto the bed, lifted Jayden to a sitting position and, still wearing the oily mitt, grabbed both pigtails and looked into Jayden’s eyes.
‘You won’t cum without Master’s permission again will you boy?’
‘No Master,’ whimpered Jayden.
‘Good. Now you will make Master cum and then we will get started with the evening’s actual foot tickling. That was just the warm-up.’
‘Warm-up?! Oh my God Master… That was so ticklish, I don’t know if I can…’
‘Ok, ok. No more talking.’
Curt guided Jayden’s face back down and started to rub his immense throbbing cock all over his blushing face. Jayden nuzzled it and stared at it, always wide eyed at its size. He kissed and licked at it as it passed his mouth. He accepted the lashings of stringy pre cum Curt wiped onto his face, leakages from the pent up dam of pleasure Curt had been building up since their last torrid tickle-session. Finally Curt had edged and teased himself enough and he presented his steeped cock to Jayden’s lips to be sucked.
His grip tightened on the pigtails and it slipped into Jayden’s pretty mouth. Jayden began doing the best he could to bob his head back and forth on Curt’s cock, looking up into his eyes lovingly. Curt grunted and moaned and cursed as he watched his tickle toy obediently pleasuring his cock. Jayden’s cuffed hands grabbed the duvet again as Curt gripped the pigtails and took control, fucking Jayden’s mouth and throat. Jayden began squirming, at times unable to breathe as Curt forced the cock down his throat, but he always rallied and continued sucking, his face a mask of foamy pre cum and saliva. Jayden looked up at Curt’s powerful hairy torso as the thick arms held his pigtails in vice-like grip. It didn’t take too many rallies for Curt to reach the peak of his pleasure and moan loudly as he sprayed quarts into Jayden’s mouth and all over his face. Jayden tried spiritedly to swallow but what felt like litres of pent up cum dribbled down his chin onto his button vest to mix with his own polite offering. He licked and sucked his Master clean and swallowed all he could. He looked up just as Curt looked down and their eyes met. Curt grinned hungrily and got up to return to his seat by Jayden’s feet.
TBC
His personal phone, face down on the desk, buzzed for his attention. His pulse raced. If it was whom he sincerely hoped it was, then checking at work might not be appropriate. It was unlikely anyone would stand on a chair to peer over the divider into his booth. Jayden swivelled his chair in a silent reconnaissance 360 and judged that the coast was clear. He removed his headset and checked his message.
1 new message: TickleMASTERNYC
Jayden’s palms were a little sweaty and he wondered if anyone might be able to tell how excited this message made him. Was he fidgeting? Sweating at the temples? He opened it excitedly.
‘TickleBoiToy. Your Master is horny for your ticklish feet. Go and take a picture of your soles and send it to me immediately. Wear your ankle charm. I will reward you with my cock if you are lucky.’
Jayden loosened his collar and switched his availability to away from desk to forward calls to his colleagues. Then, checking nonchalantly for prying eyes, he made his way out to the hall and down the men’s room. Once in a cubicle, he knelt on the closed toilet lid, stripped off his shoes and socks, rolled up the legs of his suit trousers and carefully clipped a slim silver chain around his right ankle. From it hung a charm engraved with the words “Property of TickleMASTERNYC”. Jayden snapped a few pics of his bare feet, posed as seductively as he could manage and ensuring the charm was visible. He sent several back to TickleMASTERNYC along with a message.
‘Here are my ticklish sissy-boi soles and toes Master. I can’t wait for tonight. Please send me your delicious hard cock. My tootsies want to stroke it.’
Jayden put his shoes and socks back on as quietly as he could, flushed and headed back to his office to turn in a Friday afternoon of distracted work answering calls for insurance claims from angry people he didn’t care about. No one got much done on Friday afternoon right?
When the end of the work day finally came around, Jayden politely declined work drinks despite the persuasiveness of some pretty female colleagues and slipped out. He headed straight from midtown to the upper east side and buzzed the intercom for the penthouse flat of a luxury apartment block overlooking the park. The buzzer was answered.
‘Hi, It’s Jay. I’m here Sir.’
‘Who is Jay?’ Jayden gulped, waited a few seconds for an elderly lady resident to get into the lift and for the doors to close, and then replied.
‘It’s your TicklBoiToy Sir.’
‘Well up you come then.’
Jaden waited for the elevator to come back down then rode it up to the top floor where his Master’s suite awaited. He was about to knock on the door but it swung open and his knock whiffed into empty space. TickleMSTERNYC, Curt to his friends, stood before him breathing heavily. Master was clearly in a rush to get the evening’s merriment underway.
Jayden knew his Master was a big guy but after a day of getting into his subby sissy obedient headspace (and sporting a raging boner all day from it), he was always intimidated by Curt’s physicality. Curt was 6’5”, fully 9 inches taller than diminutive Jayden, and a square 250lbs. He certainly wasn’t a bodybuilder, but he wasn’t tubby either, just built like a Silverado full of steak. He shaved his chin but wore a full moustache. He usually wore expensive casual chinos and loafers costing more than Jayden’s monthly salary but on this occasion, he had answered his door in just a robe.
Curt grasped Jayden firmly by one suit lapel, pulled him inside and deposited him gently against the hallway wall. He closed the door with one hand and flicked open his robe with the other allowing it to fall away from his thick cock, fully erect at 9 inches. No matter how many times Jayden “familiarised” himself with that monster cock, the first sight of it always rendered him rabbit-in-the-headlights awestruck. Curt smiled.
‘You’re so cute when your eyes go wide like that. What are you waiting for? Greet your Master properly.’
Jayden knelt before his Master and gingerly reached up his hands to gently stroke the shaft of the eager throbbing cock before him. Transfixed by it, he began licking around the tip and taking the head into his mouth as he stroked the shaft with his hands. Curt looked up at the high ceiling and growled in approval as Jayden’s delicate fingers and mouth Licked, sucked and gently tickled all over his cock making it throb all the harder. Jayden was pushed comfortably but inexorably into his fully submissive headspace by the ramrod hard cock looming over him and he willingly embraced it. He couldn’t wait to leave all traces of his masculine persona behind and submit his soft boy soles to whatever sadistic tickle tortures Curt had in store.
Curt reached down and stroked aside a lock of blonde hair which had fallen over Jay’s cheek blocking the view of the sprinkling of freckles on each blushing cheek.
‘Hello TickleBoiToy. I’ve missed you. We have all weekend.’ Jay looked up and nodded as he continued sucking. ‘However, your Master shoudn’t have to prompt you to greet him properly should he?’ Jayden gently shook his head, his mouth very much full. ‘Maybe we need to make you squeal extra loud this weekend huh? Are those cute little tootsies of your feeling ticklish?’ Jayden nodded. ‘Good.’
Curt reached down, took hold of jayden by the shoulders and forced him down to lie on the plush carpet, still only just inside the front door. Curt rolled his TickleBoiToy over on his belly and sat down straddling him, sitting on his butt and the small of his back and facing his legs. He then lifted Jayden’s feet up and quickly stripped off his shoes and socks. Jayden’s view comprised the inside of the front door and nothing else. Even though not yet tied in the bondage he knew he had to look forward to, he would have been utterly powerless to try to buck Curt off him. Curt, rolled his suit trousers up to his knees and began to half tickle half stroke Jayden’s calves, checking that his TickleBoiToy had shaven his legs as instructed. They were smooth, pale and baby soft. Curt examined the charm anklet. He held Jayden’s feet in his hands and leaned in for a long sniff of their scent, his moustache tickling Jaden’s toes. Jayden creased and fought back the giggles but Curt had noticed. A few giggles, while silent, had caused Jay to wriggle a little and Curt missed almost nothing where ticklish reactions were concerned.
‘Wow TickleBoyToi… You’re that ticklish? Just my moustache? Awwww, breaking you is going to be too easy!’
With that, Curt licked from Jayden’s right heel all the way up his soles to the toes and then stuffed all five dainty toes into his mouth at once. Jayden laughed out loud and squirmed. His fate was sealed. Curt moaned urgently as he tongue-probed the ticklish toes before him. The he grabbed the other foot and repeated the process lick-tickling every inch of both of Jayden’s feet as he giggled and squirmed about uselessly beside the shoe rack.
‘Oooooh fuck me Boi, I want you right now but I insist on the proper ceremony. You know where the changing room is. Everything you need is waiting for you. Go and get changed very quickly and then step into the playroom and offer yourself to me for tickle-torture.’
Jayden still had the salty taste of Curt’s pre cum on his lips as he hurried into the snug ground floor study Curt used as the changing room. There on the daybed was his Master’s choice of initial outfit for the evening, all laid out: A tiny white waistcoat with two buttons exposing a generous length of midriff, a pleated high-waisted grey tartan schoolgirl skirt (exceptionally short), tiny pale pink frilled ankle socks, black patent leather Mary Jane shoes (which he knew existed only for the pleasure of stripping them off in the first minute), pale pink frilled lace gloves to match the socks, tiny white panties and a black silk choker collar. All of his clothes were perfectly fitted, bought specifically for him by his adoring Master, all apart from the panties which looked wholly inadequate to contain Jayden’s excitement. There were also two elasticated hair ties with little pink bows. He quickly stripped off his suit and underwear and savoured the pleasure of getting dolled up like a girl for Master. He added the final touch using the mirror of the dresser: He braided his blonde hair into French plaits with the pink bows, one right and one left, just long enough for Master to grab. He admired himself in the mirror. He noted with excitement that the curve where his buttocks met his thighs was visible when he bent as much as a few degrees – just as Master liked.
He took a deep breath, left the room and stood in the corridor where Curt was waiting.
‘Oh, my dear little TickleBoiToy! Wow. You look just delicious. I could just tickle you silly with a feather duster right here in the corridor. Give me a twirl.’
Jayden obliged and turned 360 to show his Master how well his sissy outfit fitted him. Curt, practically drooling, allowed his robe to part and his hard cock to stand to attention pointing at the object of its desires, Jayden’s svelte young body.
‘Ok Toy. Upstairs now.’
Jayden climbed the stairs with Curt following a few steps behind, gazing up his skirt at the tiny snatch of white fabric visible at the top of his butt.
Jayden entered the Master bedroom where most of Curt’s toys and bondage gear were assembled. There was a four poster bed with various attachments for cuffs both ankle and wrist. A set of heavy ankle stocks was bolted onto the foot of the huge bed. A wooden pillory stood in one corner of the room, height adjustable naturally. A camcorder on a tripod stood facing the stocks. Along one wall was arrayed a selection of cuffs and restraints and on a dresser opposite the bed lay a devilish selection of tickle tools including assorted feathers, electric toothbrushes, banjo picks, a pair of pet grooming gloves, hairbrushes, vibrators and large tubs of both coconut oil and Vaseline. Curt watched Jayden taking it all in and smirked with predatory intent. He walked up behind and held Jayden by both arms, allowing his cock to nudge against Jayden’s mostly bare butt cheeks and to nestle into his crack and leave snail trails of pre cum.
‘Well, my little TickleBoiToy, here we are in my special tickle dungeon.’ Curt reached over and hit the record button on the camera. ‘I hope you’re feeling ticklish. You owe me a great deal of laughter. I want to make you laugh and squirm and beg until you can’t breathe. Do you submit to me as our Tickle Master boy?’
‘Yes Master!’ Jayden nodded eagerly. Curt leaned in to whisper in Jayden’s ear as his grip tightened subtly on Jayden’s arms.
‘You like it that your sexy little feet turn me on don’t you boy?’
‘Yes Master.’
‘You like teasing real men with your sexy soft ticklish sissy feet don’t you? You like making real men’s cocks hard with your cute little toes don’t you?’ Curt pushed his hips forward and his cock slipped upwards to push against the small of Jayden’s back.
‘You want it don’t you? You want my cock?’
‘Yes Master, I do want your cock.’
‘Well, your feet pics teased me a little already, but before you earn my cock I think I need the real thing. Sit on the bed and place you ankles in the central holes of the stocks.’
Jayden, guided by Curt’s strong hands on his arms, walked over to the bed and climbed on exposing his barely covered little bubble butt under his skirt. He sat down and offered his ankles to be locked in the stocks, nestling each into the padded notch and allowing Curt to drop the stocks closed with a loud ‘clack’. He offered his wrists to be cuffed behind his back and Curt obliged firmly. Curt pulled up a stool at the foot of the bed where Jayden’s gorgeous smooth size 8 feet protruded vulnerably, still in their little pink ankle socks and black Mary Janes.
‘Well don’t you just look as pretty as a picture?’ Curt said it largely to himself as he settled in and started to savour the ritual of slowly unbuckling Jayden’s little black shoes one by one. He stared regularly into Jayden’s eyes transmitting his predatory energy and making Jayden’s pulse race, making him both genuinely apprehensive and excited about how ticklish his feet were and the ordeal they were about to be put through.
‘What’s in here? What’s in this cute little shoe huh? Aww, is it a little wiggly tootsie in a pretty pink sock? Awww and it can’t go anywhere… Oooooh coochie coochie coo little tootsie.’
Curt, speaking again mostly to himself, gave Jayden’s right foot a few seconds of very light tickling through his sock. Jayden creased up, closed his eyes and curled his toes over, trying and failing to hold in the giggles. Curt watched his reactions, drinking them in like fuel, before starting to unbuckle the second shoe. He gave the left foot a similar light tickling and Jayden shook his head and began giggling silently, punctuated with shrill yelps of ticklishness, surprising even himself at their girly pitch.
‘Awww, is somebody tick-a-lish? Yes, I think so? Huh little TickleBoiToy? Aare your cute little tootsies ticklish?’
‘YES… MMMMM… OH crap oh crap OOOHOHO…!’ Jayden hyperventilated to try to get enough breath to provide the full answer he knew his Master demanded. ‘YES MASTER… They ARE TICKlish oh my god OH MY GOD EEEEEP!’ EHEHEEE!’ The tickling rendered his voice unreliable, seesawing between his own wobbly but recognisable register and loud panicked squeaking. Curt was as vocal as ever with his teasing, all of which made the tickle-humiliation even hornier for Jayden whose own cock had long since escaped its tiny whites and now stood visibly to attention betraying how much he secretly loved to be sissified and tickle tortured on his soft boy feet.
‘Ooooooh yes they are, yes they certainly are! And that’s with the cute little pink sockies still on. How’s about we peel off those little sockies huh?’
Curt began unrolling the socks of both of Jayden’s feet from the ankles, tickling as he went, until finally he had rolled socks covering just the toes. He held onto the left and tickled the bare arch beneath allowing the foot to involuntarily wiggle itself free. Curt repeated the process with the right foot and then straightened out the socks and draped the carefully over each side of the stocks where Jayden could see them. Then he sat back a little and took in the beauty of Jayden’s young bare soles and his vulnerable slender toes just begging to be tickled. The playful smile dropped from his face for a moment as the true predator took hold.
He reached his hands out and began stroking and tickling and tweaking at Jayden’s captive feet, enjoying them and harassing them with light darting unpredictable tickles. He was breathing heavily and his smile had not returned.
‘So soft…’ Curt mumbled to himself.
Jayden continued laughing and yelping and squealing and trying to catch his breath, the unpredictable attacks almost worse than sustained tickling. He looked at his Master’s face but Curt looked only at his feet now, absorbed.
Curt picked up the pace and began tickling the arches of both feet causing Jayden to try to curl his toes over and point his soles to the ground. This didn’t help of course, save possibly to be so adorable that Curt throbbed closer to a hands-free orgasm.
Abruptly Curt stopped.
‘Point your toes up.’ Curt spoke the order bluntly. Jayden obliged, stretching his soles out taut, arches down and toes up, accentuating the curve of the ball of his foot.
‘Spread the toes.’ Curt pulled the camera tripod a little closer as Jayden spread his toes exposing the super ticklish spots in between.
‘Wiggle the toes.’ Jayden wiggled.
‘Say “I’m a little slutty foot tease and I deserve to be tickle tortured”.’ Jayden repeated the phrase.
‘Say it again while wiggling the toes.’
‘I’m a little slutty foot tease and I deserve to be tickle tortured,’ said Jayden, humiliation causing his voice to stumble over the words. Curt stroked his cock a little, his need becoming more urgent. He stood up and hurriedly retrieved two long feathers from the dresser arsenal.
‘Hold the toes still and spread. I want to film your reaction to feathers being dragged slowly between your toes. If you clench your toes up, I will make you suffer more. Understand?’
‘Yes Master.’
Curt worked the feathers in between the outermost toes of both of Jayden’s feet. Jayden giggled and wiggled his feet.
‘I warned you boy.’
‘I’m sorry Master, I couldn’t help it!’
‘I want to get this on tape. I want to watch your face contorting with ticklish concentration as you try to hold still. You get one more chance.’
Curt once again threaded the feathers in between Jayden’s toes. Jayden, a little better prepared for it now, began a torrent of loud non-stop giggles but managed to keep his trembling shaking feet semi-still and his toes spread. The rest of his body channelled the reactions he had to let out somewhere and he fell backwards onto the bed, lying to one side with his cuffed arms under him, clawing at the duvet and making an assortment of delightful ‘yips’ and moans and giggles. With his eyes closed there were only the sensations of the feathers between his unbearably sensitive toes, the sounds of his own giggles and squeaks and, if he listened carefully, the animalistic breathing and bass grunts of his Master’s pleasure. Jayden had to admit that concurrently with the panicky torture flavour of the tickles, the sensations also felt divine. The two mutually exclusive reactions stormed around each other like oil and water creating a paradox of tickle-pleasure he couldn’t have explained if he’d tried. He physiologically needed to get his poor toes away but psychologically needed them to be tickled. His opposed urges did have one thing in common though: They both served to drive him senseless with lust. His cock was throbbing, in need of release. He tried desperately to restrict the movement of his toes to mere trembling, not full wiggling, struggling to keep them fully available for his Master’s enjoyment.
The feathers went from the pinkie toes, to the next toes, to the next soft little toe crease, then finally the last where they swirled a maddening little dance around his big toes before heading out towards the pinkie toes again.
Much more of the delicious torment of the feathers on his toes and Jayden was in danger of spraying much as, unbeknownst to him, his Master was from the lust of tickling his toes. Jayden opened his eyes and looked down the bed through eyes filled with tears of laughter. He was too weak from laughter to get back to seated position. He couldn’t make out his own feet from lying on the bed, only the unyielding wood of the stocks where his shaven legs passed through. The stocks were tall and sturdy and obscured his feet from his sight entirely. Everything below his ankle had been surrendered into some other realm of super masculine tickle monsters. He had no way of knowing what was being done to his feet other by feeling it as it happened. He couldn’t even make out much of Curt, only the top of his head and his wide shoulders hunched over, completely absorbed in the task at hand.
‘Oooooh God…’ growled Curt as he dropped the feathers to the floor and sent his fingertips diving under the toes and then skittering south to the arches. Jayden’s feet reacted immediately to the new attack and wiggled for all they were worth, no longer able to keep still for the tantalising soft feather tickles. Curt was too lost in tickle lust now not to dig in looking for screams from his young lee.
Jayden’s sexy soft feet wiggled and curled over wrinkling the soles, then stretched spreading the toes, then alternately one up and the other down as Curt varied his attack, his fingers exploring precisely wherever they pleased over Jayden’s ticklish feet.
Jayden’s mind was in turmoil. His eyes were closed. His little bubble-butt was clenched tightly, and his options quickly narrowing to one: To cum just from the tickling of his feet. It was as he was hyperventilating through that thought that Curt leaned over and French kissed his left foot. Curt’s fingers carried on tickling the right but all five petite toes of the slender left disappeared into Curt’s mouth to be feasted on and thoroughly tongued.
Jayden arched his back and came immediately sending a jet of cum up into the air to splatter back down over his toned belly and white button vest. Curt looked up over the stocks with a raised eyebrow.
‘Oh really? TickleBoiToy likes getting his toes sucked huh? I didn’t give you permission though…’
‘I’m… Sorry… Master… I couldn’t… help it…’
‘No, I see that. Well, I’ll reduce your punishment from 5 minutes to 2 then.’
Curt retrieved a stopwatch, a grooming glove and a bottle of baby oil from the dresser. He oiled Jayden’s feet causing him to moan in pleasure, slipped on the glove and then administered 2 carefully timed minutes of unbearable post-orgasm foot tickling with the scratchy grooming mitt. Jayden squealed and cried and bucked in genuine distress and Curt adhered strictly to the timer, watching the suffering of his darling pigtailed sissy tickle boy until the last second elapsed. Then he climbed onto the bed, lifted Jayden to a sitting position and, still wearing the oily mitt, grabbed both pigtails and looked into Jayden’s eyes.
‘You won’t cum without Master’s permission again will you boy?’
‘No Master,’ whimpered Jayden.
‘Good. Now you will make Master cum and then we will get started with the evening’s actual foot tickling. That was just the warm-up.’
‘Warm-up?! Oh my God Master… That was so ticklish, I don’t know if I can…’
‘Ok, ok. No more talking.’
Curt guided Jayden’s face back down and started to rub his immense throbbing cock all over his blushing face. Jayden nuzzled it and stared at it, always wide eyed at its size. He kissed and licked at it as it passed his mouth. He accepted the lashings of stringy pre cum Curt wiped onto his face, leakages from the pent up dam of pleasure Curt had been building up since their last torrid tickle-session. Finally Curt had edged and teased himself enough and he presented his steeped cock to Jayden’s lips to be sucked.
His grip tightened on the pigtails and it slipped into Jayden’s pretty mouth. Jayden began doing the best he could to bob his head back and forth on Curt’s cock, looking up into his eyes lovingly. Curt grunted and moaned and cursed as he watched his tickle toy obediently pleasuring his cock. Jayden’s cuffed hands grabbed the duvet again as Curt gripped the pigtails and took control, fucking Jayden’s mouth and throat. Jayden began squirming, at times unable to breathe as Curt forced the cock down his throat, but he always rallied and continued sucking, his face a mask of foamy pre cum and saliva. Jayden looked up at Curt’s powerful hairy torso as the thick arms held his pigtails in vice-like grip. It didn’t take too many rallies for Curt to reach the peak of his pleasure and moan loudly as he sprayed quarts into Jayden’s mouth and all over his face. Jayden tried spiritedly to swallow but what felt like litres of pent up cum dribbled down his chin onto his button vest to mix with his own polite offering. He licked and sucked his Master clean and swallowed all he could. He looked up just as Curt looked down and their eyes met. Curt grinned hungrily and got up to return to his seat by Jayden’s feet.
TBC
