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Tickle Tutor: Collateral #4 'Due Process' M/f


4th Level Red Feather
May 5, 2001
Tickle Tutor: Collateral

A Short Story Collection From The World of Tickle Tutor

By TickleMantis


‘Due Process’

For thirty years or thereabouts Lola Romito had seen her fair share of different jails. She’d been arrested young and kept up the habit across most of the Midwest, some of the South and into the Rockies. Now nearing her mid-forties, the feeling of handcuffs tight around her wrists was all too familiar. After the first few times the cold steel and distinctive click no longer fazed the tall and heavily-tattooed woman, not until she’d got together with Roy at any rate. Now those small metallic clicks caused an anxious twist in her belly, just as it did when Sheriff Mackleroy caught up with her at Rusty Rocco’s.

Rocco’s was one of three less than reputable bars in town and every bit as charming as the name suggested. Roy had simply stood by and laughed as the mustached old lawman dragged his girlfriend out of the dimly lit joint and into the bright afternoon sun. In fairness, Lola would have done the same were their situations reversed. It was not the first time for her, nor her man, that Mackleroy had slapped the cuffs on either of them. Two years in that Podunk mountain town and the busty blonde must have been tossed in the local lockup at least four times.

“The hell is this?” Lola asked twenty minutes later when the cowboy of a sheriff pulled from a quiet rural road onto a dirt stretch of dust that could barely be called a driveway. High trees and overgrown grass bordered either side, the leather-clad woman’s ballooning and colourfully-inked cleavage jiggling over every bump. “God damn it, where are we going?”

Shifting her shapely behind forward, tight leather pants sliding easily on the seat, the perplexed prisoner peered through the black mesh cage that split the patrol car in two. Up ahead were two more vehicles, another beige car with ‘Deputy’ printed boldly on the side, and a police motorbike. It was half the sheriff’s department, all apparently come to gather at an abandoned hovel in the middle of nowhere. Noting the building they were parked around, the dilapidated thing could scarcely be called a shack. No glass in the windows, a great hole in one side of the roof, the chimney half collapsed. This was no police station by any stretch of the imagination.

“Mackleroy?” Frowning when the engine stopped, Lola raised her raspy voice as the sheriff climbed from the car. “Mackleroy!”

Pausing outside to put on his white Stetson hat, the wrinkled and wiry man let the driver’s door glide gently shut behind him. To the muffled sound of the sheriff’s boots upon dry ground, his worrisome detainee watched as he slowly took the two steps to the back door. Hands clamped behind her back and the rest of Mackleroy’s small posse obviously nearby, Lola figured there was no sense trying to fight her way out. Maybe she could run if given the chance, capable as the old officer was he probably wasn’t near as fast as he used to be. Still, Lola was plenty familiar with the town deputies and knew for a fact at least a couple of them would have no trouble chasing her down.

“Out you get.” Said the old man as opened the door and stood off to one side.

“Uh uh, no way.” Wriggling toward the opposite side of the car, the confused woman ducked a little to keep eye contact with her capturer. “Not until you tell me what we’re doing here! You didn’t even tell me what I was picked up for. I don’t have any warrants right now.”

“Maybe not in this state.”

“So what, you’re collecting bounties now?” Lola sneered. “You can eat me! Take me back to the station, I want my lawyer.” And with that she sat upright and starred straight ahead.

Mackleroy huffed, more tired than angry. “Sure you want your lawyer?”

Of course she could hardly afford a lawyer and in that town there wasn’t one. At best there were a trio of public defenders in the nearest city a forty minute drive away, and Lola had burned through two of them already. Were it not for her boyfriend and the fear of what he’d do to her, the life long petty criminal would have already left town months ago. But, as was so often the case in Lola’s life, the decisions she made were dictated by men. Men like the sheriff and Roy, or the bikers she so often ended up hanging around with in any given place. Tall and busty with a great mane of blonde hair, she was always going to attract attention. Sadly it so happened to usually be the attention of those who felt their own desires held priority over her’s.

“Come on.” The sheriff’s tone turned a little stern. “Behave yourself or I’ll have Carson and Whitmore come up here and drag you out.”

Lola took a last moment of defiance before relenting. “Fine.” She said and shuffled toward the open door. There would be no escaping the deputies, especially those two. Carson was all brawn and mean as a bull, and the younger Whitmore had been a star quarterback in high school just a few short years before. “But you better tell me what the hell we’re doing here, I swear to god. Bringing my ass all the way out to wherever.”

“Yup.” Mackleroy swung the door shut behind his prisoner, the waft of air brushing the exposed small of her back. “Answer’s in there.” He pointed one thumb back over his shoulder.

“I’m not going in there.” Shaking her head, the puzzled Amazon furrowed her brow at the broken down cabin. “Seriously…” She turned focus to the sheriff. “Wh…what is this, Mackleroy?”

“Do you need assistance?”

“I’m not going!” Lola took a step back, and with surprising speed for a man of his years the old cowboy closed the gap between them.

“That’s enough out of you.” Bony hands grabbed at the fitful woman’s right arm and forced her to twist toward the car. He might’ve been wrinkly, but he was strong.

“Hey!” Staggering about, the slender woman stomped her heeled boots into the dust as the sheriff maneuvered himself behind her. “Let me go! This isn’t right!”

“Now you’re concerned about what’s right?”

“What’s that supposed to mean?!”

“Mean’s you oughta be more careful about who you muddle with.”

“What? What are you talking about?!” Lola winced as the older man held both her arms, just above the elbows, and forced her around to face the ruined little house.

Pushed from behind, each step was an off-balance jolt toward the cabin. As they passed between patrol cars, the restless blonde racked her brain to think who she might have upset to get her in such a predicament. It was a sorrowful realization that the list was startlingly long, even in a town so small. She’d ripped off the scrap yard guy, seduced and subsequently blackmailed an owner of one of the two cafés, shoplifted from every shop on Main Street, ripped off the scrap yard guy again, and that was just in the last month. There was also what she’d done to Deputy Armstrong out in the back country, though it couldn’t be that. For her own sake Armstrong would never tell a soul about their encounter. There was no way.

Into the decrepit hole of a door, the floorboards creaked underneath and daylight faded. A few reluctant steps through a narrow hall, the walls warped and bowed, it took a moment for Lola’s eyes to adjust. Stopping and blinking hurriedly, she looked down to see a gaping rectangle opening in the floor, a set of rickety wooden stairs descending into darkness. Mackleroy urged onward and the squirming woman struggled a little harder, pushing back in the knowledge that nothing good would be waiting for her down there.

“Mackleroy, damn it!” Lola squawked as she slipped, landed on the top step and nearly toppled clean down into the void.

“Easy now.” The old man spoke as if he were trying to calm an ornery horse. “Don’t want you getting hurt.”

Had she known exactly what those words meant at the time, the bosomy outlaw would have gleefully thrown herself down the entire flight of stairs. Looking back, being in traction would have been preferable to what became of Lola in the weeks and months that followed. In the moment she’d thought nothing of the sheriff’s line about not harming her, expecting a few threats or maybe getting run out of town. Worst case scenario the deputies would have their way with her and send her limping back to Roy. It’d hardly be the first time she fucked a cop to get out of trouble.

Dully illuminated by two narrow windows at the top of a cinderblock wall, the basement felt considerably colder than the overgrown building above. Oddly clear of weeds or much in the way of debris, the dank sublevel had a concrete floor with a dark green rug at the center of it. It was quite tidy all things considered, well-kept even. Stepping down the last flimsy stair, Lola looked back, the half of the room behind the stairs cast in shadow. Predictably, deputies Carson and Whitmore were waiting, both stood below a window each and both with their muscular arms folded.

“In trouble again eh, Lola?” Carson grinned, daylight reflecting off his bald head. Sporting a big black goatee, the burly bastard would have fit in a lot better with the local bikers than he ever did in a police uniform.

“She’s got a thing for it, I’m pretty sure.” Whitmore stood off the wall, all boyish good looks and lantern jawed. “You know, one of those women who likes being…disciplined.”

“Look-“ Coming to a stop at the middle of the rug, Lola looked up to the low ceiling where a clip-style carabiner hung from a chain, the other end bolted to one of the crisscrossing wooden supports above. “How about I just suck all your dicks and you let me go?”

The two deputies chuckled and Mackleroy stayed eerily silent. Fidgeting around behind her, the old lawman turned a tiny key and let one side of the handcuffs fall loose. Relieved, Lola forced a smile as she bought both hands around to her front. Just before she could nurse her free wrist with a rub, Carson strode to within inches of the unbound captive and grabbed both of her forearms. Pulling back, the outnumbered woman felt the taller deputy’s grip tighten, her arms failing to move in the direction she wanted.

“Not so fast.” Said the hulking man as he forced her wrists back together.

“Whatever you want, whatever I’ve done-“ Lola began, her arms shaking as the much stronger man raised them upward. “This –whatever this is- you don’t need to do it. I’ll leave. I’ll just leave, okay? You’ll never –nff- see me again!”

Her boyfriend be damned, she meant it too. Roy would try to find her and if he did the consequences for running would be unbearable. Far and fast, Lola thought as she winced against her gradually rising arms, she’d just have to flee far and fast. Corrupt members of law enforcement always had their unconventional ways of getting what they wanted, usually that meant money or sex. A chain hanging from a basement ceiling was a new one on the well-seasoned offender, and what the three men had in mind she couldn’t quite figure. As she clenched her fists in one final effort, the chain of her handcuffs was pushed through the carabiner clip, trapping Lola’s arms above her head.

“You should have left already.” Mackleroy’s gruff voice came from behind. “If you’d have done that, we wouldn’t need to be doing this.”

“Okay! Okay, I get it!” Twisting to face the stairs and the eldest of the trio, the firmly trapped woman’s elbows bent slightly either side of her head. “I-I know where Roy’s money is, I do! He keeps it all in cash and-“

“Ttt.” The sheriff scoffed. “Roy Wenterlant’s barely clever enough to call himself an idiot. If he’s got any money it ain’t much, and that boy hasn’t hid it anywhere we couldn’t find in a matter of minutes.”

Deputy Carson was still looming less than a foot behind Lola’s back. “Besides, we got better things to do than waste time on that pissant.” And with that the bullish officer used his thumbs and index fingers to pinch directly into both the svelte blonde’s exposed sides.

“Eeiieha!” Arching her back sharply, the surprised captive’s eyes shot wide and her boots raised to stand instantly on her toes. Rocking back and throwing her generous hips from side to side, the abruptly squealing woman tugged wildly at her arms as the deputy’s prodding digits moved lower. “Eiieiiahaha! Stop it!”

“What did you think this was, Lola?” Mackleroy spoke loud enough to be heard through the spasming Amazon’s girlish giggles, his eyes unashamedly fixed on her bouncing cleavage. “Did you think you’d get away with what you did? That you wouldn’t be punished?”

“Macklereeiehehehe! Sh-sheriffahaha!” Unable to stifle her increasingly panicked laughter, the voluptuous detainee pulled her knees up high, dangling from the short chain as Carson’s fingers poked up and down her bare, heaving sides. “Stop him! Eehahaha! No-nonohohoho!”

“No can do. We’re here to tickle you, and ticklin’s what we’re gonna do.”

Hearing the word tickle, especially in the throws of having unwanted fingers jabbing at her flesh, caused Lola’s stomach to plummet. There was nothing worse as far as the bosomy bandit was concerned. Beatings she could take just as well as she could dish out, it was simply part of The Life. Tickling on the other hand, that nightmarish sensation, the hellish loss of control and humiliation as laughter poured from her uncooperative body, doing a year in lock-up was easier than a even a moment of it. Tragically, as it had always been for the hopelessly sensitive crook, just a few quick strokes or pokes across her soft skin could easily dismantle that hard-earned tough girl reputation.

Lola slammed her boots down and tried to turn around, the deputy easily keeping her facing away from him. His thick fingertips wormed up and under the bottom of the alarmed woman’s sleeveless leather top, thin shoulder straps straining to remain intact. Wiggling his index fingers, Carson drilled cruelly into the tender spots between her lowest-most ribs and she lurched forcefully forward. Her expression contorting through fury and goofy, open mouth grins, there was no direction that offered any respite while she danced awkwardly in the small space the restraints would allow.

“Please! Ahheehahaha!” Lola squeaked after nearly a full thirty seconds of desperate struggling. “I’m sorreeeihehehe! Stahahahap!”

“You even know what you’re sorry for?” Said the sheriff plainly, and in truth the fitfully laughing blonde didn’t have an answer.

“Okayeehahaha! I’m done! Ahahaha! I’m dooooneeiiehehe!”

“Oh, you hear that boys? Lola here’s done.”

“Guess we’ll pack up and go home.” Carson bought his remaining six fingers into the fray, each one tapping hurriedly against her upper sides.

“Eieeehahaha! Pleheeheease!” Closing her eyes tight. the cripplingly ticklish captive tried to distance herself from the overwhelming assault. It was an impossible feat that had never once worked, yet she still couldn’t help but try every single time. “Enohahaugh! Eieiehaha! J-just stopahaha!”

“Don’t tell me you’re not enjoying my deputy’s administration of justice!” Mackleroy took a step forward, bought both hands up into the air and quickly clawed at the busty criminal’s flat tummy. “Maybe I can help!”

“NOOOOEeeeiiii! Nopleaheeahahaha!”

For all the times she’d been teased into insuppressible laughter throughout her life, rarely had Lola ever been tickled by more than one person at a time. It was a small and sorrowful thing to be thankful for, yet it made a big difference in the face of it. One tickler could be convinced or distracted, if she were lucky, into doing something else. Two ticklers, well they had a tendency to egg each other on. Aside from the added chaos of all those additional wiggling fingers, trying to change the minds of two people at once wasn’t just doubly difficult, it was borderline impossible. Between Mackleroy and Carson, the likely chance of any mercy felt like less than zero.

As the sheriff’s ten digits crawled up and down her convulsing tummy and the bald deputy dug at her ribs, Lola’s whirling mind forced forward a memory she’d have much rather forgot. It’d been New Orleans damn near twenty years before and the then less ink-covered blonde had taken two particularly strapping seamen back to her rented, crummy trailer. She’d met them at a bar frequented by navy personnel and the handsome duo didn’t need much of any convincing toward an illicit ménage à trois. Quickly disrobing, the three tipsy twenty-somethings eagerly piled into the creaking bed, only for a rogue fingertip tracing up her thigh to make Lola squeal just a few seconds into the fun. Spurred on by their new friend’s display of hyperticklishness, the two boisterous lads gleefully set about squeezing, groping and poking every painfully sensitive spot they could find.

The two navy boys hadn’t tied her up, that wasn’t a torment which even occurred to her until she’d met Roy. Still, the excited hands of those young men were no less inescapable as handcuffs. Lola had lay sandwiched between the two masses of muscle, constantly trying to sit up or wriggle away, her harrowing and very genuine pleas utterly undermined by riotous laughter, and the sailors’ seemingly endless amusement. Somehow, in some way she couldn’t recall from the fervor of it all, the outnumbered girl had ended up facedown at which point one of the men helped himself to her pussy. While he rode her from behind the other lad kept tickling, the pair of them switching roles once the first was satisfied. In the end they both fell asleep and Lola robbed them blind of their drinking money, just as she’d planned all along. It had been a lot more work than the young thief ever intended though, and no amount of cash had ever been worth that kind of suffering before or since.

“You’d think a woman as ticklish as you would be more careful who she messes with!” The sheriff danced his nimble digits along the prisoner’s lower tummy, just above her beltline. “Course I’d hardly expect someone who dates a dope like Roy Wenterlant to make good decisions…”

“Hell, maybe we should’ve done this when she first came to town.” Carson added as he snaked his hands further up and under her severely stretched top. “Save us all a lot of trouble!”

Between all the jostling of her large bosoms and the already skimpy nature of her clothing, having the deputy’s fingers creep between the leather and her agonizingly sensitive skin was putting the straps and stitching both to the ultimate test. The kind of outfits Lola usually wore weren’t mean for a lot of rigorous motion, the thin silver zipper down the front of her chest already beginning to part. As her squished, quaking cleavage slowly became further exposed the poor woman’s laughter was interjected by hoarse gasps for air. Every squealed, begging word required a good deal more willpower than the one before it, all that energy wasted as neither of the men so much as slowed.

“Had enough?” Mackleroy withdrew his deft digits and shot a nod to the younger lawman.

“Y-yes! Ah-ah! Yesyes!” Lola wheezed when Carson slid his fingers out from under her top. Squirming in place, she tried to free herself of the left over tingles. “I swear! I swear, okay?! Whatever you want from me, I’ll do it!”

“Mmhm…that’s kinda your problem, ain’t it?” The Sheriff moseyed toward the stairs, put one hand on the railing and turned to sit upon one of the lower steps. “What we wanted from you was the opposite of what you already did.”


“He’s saying-“ Taking hold of the panting woman’s hips and making her flinch, the hulking deputy forcibly turned her to face the opposite direction. “Unless you’ve got some way of going back in time, the damage is already done.”

“So-so what?” Her steely composure returning, the scowling captive gave her best deathly stare to the two younger men. “I’ll make up for it! Whatever I did!”

Mackleroy made a sort of disapproving grunt from his perch back on the stairs. “Isn’t the fact you can’t figure which of your many sins got you into this mess a damn sad indicator of a misspent life?”

“I don’t know!” Lola huffed, almost as irritated by the sheriff’s high-horse judgment as she was by being trussed up in some abandoned basement. “Why don’t you just tell me what you’re all so mad about and I’ll-“

“Oh, we ain’t mad.” One corner of Carson’s mouth perked up in an unnerving smirk. “The folk you’ve wronged, now them? They’re mad as hell.”

“One in particular.” Deputy Whitmore’s lips parted to show pearly white teeth.

“So I’ll apologize! I’ll-“ The bound blonde began, only for the bulky man who stood much too close to cut her off a second time.

“This ain’t something you can undo.”

“Then…then…” Lola stammered as she tried to figure out the intent of her three capturers, all the while purposely shunning the most obvious idea. They’d already told her of course, yet even with that knowledge at hand it was a fate too terrible to think about. Too atrocious to truly accept. She had no illusions that law enforcement personnel weren’t capable of such vile cruelty, only a prayer that the trio now surrounding her had a lot more bark than they had bite. It was all talk, it had to be. Threats to keep her scared, that was all.

“Justice, punishment. Call it what you want.” Carson raised both hands up to shoulder-height and wiggled all ten fingers in the air. “We just call it tickle torture.”

“N-nono! No please!” Instantly wriggling, the tattoo covered prisoner glared between both sets of dancing digits as she yanked wildly at the chain above. “Not my pits! Not my PIIEEEEIIEHEE!”

Before she could finish, the brawny deputy’s hands darted forward, every one of his skillful fingertips scribbling all over the trapped woman’s underarms. Jerking furiously at her unbreakable restraints, Lola shrieked, unable to bring her arms down enough for any protection. Failing horribly, the second idea worked just as well; Going on tiptoes in the hope that somehow she could pull her body up high. Neither panicked maneuver achieved anything helpful as Carson’s digits ran freely over the smooth, defenseless skin of her hollows.

“Where you going?” The burly lawman’s hands followed as his loudly laughing victim twisted away.

“STOAHAP! STOPIIIIT!” Now facing away from the man, Lola screamed, his hands reaching around and continuing their evil task. As she fought to pull away, the big bald fellow stepped in close behind, the bulge at his crotch pressing firm into her shapely, leather-clad butt cheeks. “EEIIAHAHA! NOT THEREEEHAHAHA!”

“Ohh, not there?” Carson cooed, raking his short nails down to the edges of her bosoms and back up to the bewildered woman’s biceps. “You mean here, where I’m tickling you?”


Apparently undeterred by the sporadic whipping of thick blonde locks in his face, the noticeably erect deputy kept his fingers frolicking. From the vibrantly coloured undersides of Lola’s shaking arms, the officer’s speedy strokes ran amok over her lethally ticklish underarms. Dancing downward, Carson effortlessly explored the exposed fleshy creases where the helpless woman’s jiggling bosoms met her rapidly swelling ribcage. Pressed up against him and caught between the man’s beefy forearms, there was no more twisting or turning to be had, only a quick series of clumsy steps that lead nowhere.

Eyes bursting wide and closing tight at random, the laughing yet miserable jailbird continued to catch blinking glimpses of the all too relaxed sheriff. Lounging on the steps, his elbows rested behind him, Mackleroy looked upon Lola’s anguish like he was watching a sunset from his front porch. A haunting thought occurred then, atrociously emphasized by Deputy Carson’s devilish touch; that the leisurely older man had seen such sights before. Perhaps the two deputies as well, strange a theory as it certainly was, had previously indulged themselves in similar fashion. Thinking back, there did seem to be a whole unspoken process to the horrid ordeal, like the three men had practiced it numerous times. Far from encouraged by the oppressive idea, Lola shook madly as she longed for immediate escape.

Her own fingers pawing aimlessly in thin air, the half-crazed Amazon’s stretched cheeks had taken on a pinkish hue. Bucking endlessly, the entirety of her frenzied focus lay firmly on the fingers spidering around her hollows. It was only through instinct that the more primal parts of Lola’s mind recognized the feeling of Carson’s rock hard erection rubbing against her bouncing ass. Despite knowing she was giving the brutish deputy a lewd massage there was no way to get control over her own untamed movements, every push, pull and erratic jump unwittingly caused by those damn tickling digits. As the large man’s covered cock swelled, another involuntary blast from the past unburied itself from the cackling woman’s bank of unwanted memories.

No rest for the wicked, it was only a day after her hellish encounter with the two navy boys that Lola once again found herself on the receiving end of poking, prodding fingers. She’d ducked out long enough for them to give up looking for their money and go home, anything of worth hidden in a plastic tub that sat behind some garbage beneath her trailer. Upon her return home the then overly cocky young woman found a few short hours of peace before her landlord came calling.

A barrel-chested and slovenly fellow with thick black eyebrows, the owner of the trailer park always knocked his fat fists against the door in the same bashing, pounding manner. Not a single other tenant Lola ever met liked the man even a little, the women of the park all despising him a good deal more than the men. The men disliked their landlord because he was an openly obnoxious oaf, so too did all the women, yet it was his leering eyes and groping, pinching hands that instilled an extra level of disdain in the girls. Up until that day Lola had done a fair job of avoiding the landlord’s handsy advances, either that or he simply hadn’t made much effort.

The ogre-like man’s claim, after she opened the door in nothing but short-shorts and a low-cut t-shirt with the lower half removed, was that her rent was due early that month. Why exactly the landlord couldn’t say, and though she had very recently acquired more than enough money to pay, the bold and bosomy girl refused on principal. It was an uncomfortable interaction but nothing Lola hadn’t gone through before, and overall should have been easy enough to argue through. Only when the beastly proprietor made mention that he’d heard her laughing hysterically late the evening before did the conversation take a turn into uncharted territory. Stumbling over her words and unsure how to respond, the busty young tenant had attempted to close the door.

Large as he was and flimsy as trailer doors tend to be, the human bulldozer of a man shoved his way inside. Powerless to stop him, Lola recalled later how silly she’d been for trying to drive the invading man back outside instead of just running away. What exactly the landlord said in those first few moments couldn’t be recalled twenty years on, and she’d hardly been listening even back then as he wrapped the much smaller girl up in his grasp. There had been some nonsense about paying the rent in other ways, that if she couldn’t pay he’d make her pay, all thinly veiled excuses to get his rough hands on soft, supple skin.

As with Mackleroy, Carson, Roy and numerous others before them, Lola had begun laughing in the landlord’s arms despite her very real distress. Like a curse that followed her always, the hopelessly ticklish girl could never keep from squealing and smiling no matter how upset she really was. Once that trailer door was kicked closed behind them, the nubile blonde’s body belonged to the oafish man for as long as he liked, and he knew it too. Stumbling together onto the living room rug, Lola’s knees almost instantly turned to jello and she’d collapsed to the floor. Giggling and fighting with the weight of her landlord coming down upon her, the poor girl hadn’t stood a chance as he’d savagely squeezed her bare midriff.

Facedown on the rug, rickety trailer rocking, the pleading, swearing young tenant had kicked and flailed as her landlord straddled the backs of her mostly bare thighs. Before she could slip away, he’d laid down atop her, his burly chest pressing into her upper back. Pinned under him with his heavy breath hot against her neck and ears, Lola had only been able to wail with laughter as he goosed her ribs and sides. It was that moment in particular that she recalled many years later pressed up against Deputy Carson, that same feeling repeated of a hard cock throbbing against her curvaceous ass.

If there had been anything to be thankful for during that experience with the landlord, it was that he didn’t last long. Within a matter of a few dreadful minutes the great lummox shivered, groaned and huffed as he made a lustful mess of his sweatpants. To that day, decades on, Lola wished that one visit had been the end of it, but the permanently unkempt man managed to get his hands on her three more times after that. The second time played out much the same as the first, he’d shoved his way in and pinned the busty girl against the couch cushions, fondling her as she’d cackled and tried to wrestle away. On the third and what should have been final time, he’d used a master key to let himself in while Lola had been in the shower. There hadn’t even been time to reach a towel.

That was it, the final straw, she’d figured while laying nude, soaked and breathless on the bedroom floor where the landlord had dragged her. Passed time to move on, there was no help and no way to avoid it. Naturally, Lola wasn’t about to run off completely undefeated, she simply couldn’t let a Neanderthal like that claim total victory. To his house then, late the night of rent day, her bag packed and ready to go. She’d snuck in, confident as the most sly of cat burglars, certain it would not take long to find the landlord’s stash of cash. What the stealthy girl found instead was that even a man of his lumbering size could move with surprising silence in the dark. Until that point in her life Lola had never been tickled so hard and for so long, waking half the trailer park with her cries.

Deputy Carson proved to have much more self control than that oafish old landlord from years gone by, and considerably more precise hands. “You going to do any work, Whitmore?” Said the cue-ball headed man as he drilled the tips of his index fingers into the chained blonde’s upper ribs. “Or just stand and watch?”

“I didn’t want to interrupt…” The youngest of the three men said dryly, though their overly flustered prisoner could hear none of their conversation.

“AAHGODAHAHAHA!” Lola howled, tendons protruding in her neck, and laugh lines deep around her bright red face.

“Besides, we’ve got time…don’t we?” Whitmore wandered around to the pleading captive’s front as he eyed the sheriff curiously.

“Plenty.” Mackleroy nodded lazily.

Wide eyed and heaving for air, the agony clear across her worrisome brow, Lola watched helplessly as the handsome deputy turned his attention to her. While Carson continued his relentless assault around her underarms, Whitmore reached up and caught the jangling zipper of her top between his thumb and index finger. Aided by the swaying, jiggling movements of the laughing woman’s large breasts, the hunky boy drew the zip downward, her squished cleavage spreading apart. With the zipper an inch from the bottom of her top, one especially sinister jab from the other deputy’s digits caused Lola to squeal and jolt sharply, the shocked jump causing both heavily tattooed breasts to spill free.

“Would you look at that?” The dark haired former quarterback tugged the zipper open, letting both halves of the leather top fly open. “Couldn’t bring yourself to get inked around there, eh?” He swiped a single fingertip across one of the maddened woman’s large, pink nipples.

“YEEEIIHA!” Lola shrieked, planted her feet and shoved backward so hard it made the bulky deputy behind her stumble.

“Ohh, I get it!” Whitmore’s lips turned up to a shark-like grin. “Our convict’s got ticklish titties!”

Amid the chaos of uninvited memories, uproarious laughter and merciless fingers exploring her flesh, the now bare breasted crook took note of very little else around her. Few words made it through the riotous clamor, the trio of despicable lawmen’s deep voices all lost or not worth listening to. Only the most important pieces of conversation caught in Lola’s mind, and the hunky young deputy’s flick at her nipple made his following observation sink in deep indeed. There were some areas no other human was permitted to touch, whether it be with an ink-gun or wiggling finger. Like her feet, thighs, ass and underarms, the area around the half naked blonde’s nipples was so hypersensitive even the briefest contact caused a reaction not unlike being struck by lightning.

“Look at that!” The young deputy traced a single fingertip around the neatly rounded edge where Lola’s chest tattoo ended. Stopping an inch from either nipple, the canvas of multicoloured ink delved down between both quaking bosoms, leaving a distinct inch-wide space from her puffy pink areoles.

“NOHO! PLE-PLEEEHEEHEEASE!” Shuddering violently, the increasingly unhinged woman shook her head.

“Don’t you love how they always give themselves away?” Whitmore looked back and forth to his fellow officers as he bought both index fingers into the air, and curled them into wiggling hooks.


For as wildly as she spun and yanked and begged there may have been some chance to keep her nipples free of the deputy’s touch, had it just been the two of them. Ganged up on as she was, the poor captive was held firm when Carson slid his large hands up under her biceps, clamping her securely in place. Horror strewn across her face, Lola watched on as Whitmore’s fingertips came close and closer still, all the while she kicked and strained until the very moment that simple motion grazed the edges of her tragically ticklish skin. The shrill cry that escaped her lips could have shattered glass, and the laughter that bellowed forth immediately after was so loud it threatened to bring the whole place crashing down upon them. What mercy that would have been.

Prying a couple of fingers free, Carson let his companion enjoy a few sadistic seconds of solo torment before reentering the inhumane punishment. Still managing to hold Lola tight beneath her shoulders, the older deputy wormed a couple of fingers from each hand into her unprotected hollows. Utterly overwhelmed by the two-pronged attack, a look of abject lunacy crossed the thrashing woman’s face, her mouth open wide and her eyes staring blankly as she cackled. Knowing beyond the shadow of a doubt a single stroke more would surely be the end of her, Whitmore soon proved the raving outlaw wrong as his double digit dancing turned to all ten fingertips flickering around her preposterously ticklish nipples.

“STEEIHAHAHA! STUHAHEEEIII!” Single syllable words no longer within her capabilities, the fuming blonde roared with deranged laughter as her sanity quickly slipped away.

Carson’s hard cock still pulsating against her bubble like butt, somewhere deep inside Lola could only pray that the beefy bastard would soon finish himself off. Removing one man wouldn’t improve her situation all that much, desperate as she was however the equation simply became; any relief no matter how minor was better than none at all. More worrying even than being tickled by two men at once was that so far at least one of them was always waiting in the wings. Classic cops, the smart ones always had back up. The way Mackleroy sat there with his old, experienced eyes watching on, it made every scream-inducing stroke and poke from the deputies all the more unnerving.

“That’ll do.” The mustached cowboy muttered after many more arduous minutes.

“EI! AHA!” Lola squawked as both deputies made sure to get a last jab in before obeying the sheriff’s order. Her upperbody falling limp, bare chest rising and falling, a light drizzle of sweat ran down the breathless prisoner’s collarbone. Knees wobbling, it was all she could do to not hang her full weight from the handcuffs.

“Let’s lose this.” Mackleroy waved a finger in the general direction of his topless detainee’s torso.

“Pants too?” Whitmore smirked while Carson slipped some sort of multi-tool from his belt and drew a short blade.

“Soon enough.” Said the sheriff without taking his squinting gaze off the panting blonde’s naked breasts. “Remember what I told you before?”

“Don’t go all in right away.” The lantern jawed lad took a tone like he was repeating something he’d heard a thousand times before. In that same moment, Carson sliced one of Lola’s shoulder straps in two.

“And why is that?”

“Cause it’s worse for ‘em if you prolong the process.”

“There you go, you are learning.” Mackleroy said as the second shoulder strap was cut away and the now ruined leather top fell to the floor.

“Gotta make ‘em think there’s still hope.” Carson folded the blade back into his multi-tool. “Like this one, right now she’s thinking ‘maybe someone will stop them before I lose my boots’. Or ‘maybe a call will come in an they’ll have to go.’ Don’t matter if she’s got nothing to back it up, keeping that hope alive is what matters.”

A disheartening shiver ran through Lola’s shoulder blades. The threat of having her boots removed was always a cringe inducing prospect, and the way the three men discussed her torment was so casual. They were nonchalant, like discussing a baseball game around the water cooler, and perhaps the thing that made it even worse was that they right. Despite their overtly spoken plans to continue stripping her, the half naked, half exhausted queen of the misdemeanors did still hold out hope. Maybe they would get a call for some emergency, maybe they’d decide she’d learned her lesson. Hope as she did, Lola also knew she’d never been that lucky.

“Please…please let me go…” The buxom captive whimpered, her voice trembling as she caught a few more breaths.

“Y’know-“ Began the sheriff, pausing to hoist himself up of the stairs. “If I thought for even a second that you were genuinely regretful of the things you’ve done, I might actually consider letting you go.”

“I am! You-you think I want this? I’m sorry!”

“You ain’t sorry.” Mackleroy strolled closer, and as he did the youngest deputy stepped aside. “All you’re sorry for is, you got caught. And jail, for you, hell girl you can do a stint in lockup like most people brush their teeth. No…for you and your crimes-“ He waggled a finger like the tough-as-nails woman before him was a naughty schoolgirl. “You need a real lesson in consequences.”

“No! Wait!” Lola sucked her tummy in and pushed her ass back as the old cowboy’s one scolding digit turned to ten flexing claws. “Noeeeiiieehaha! Stopitstoooopeeieihee!” A stream of helpless giggles burst forth when the sheriff’s fingertips dug into either side of her abdomen, her large bosoms swaying as she danced about.

“I’ll keep her busy.” The mustached man’s hands darted up, down and around the fitful woman’s tummy, never staying in the same spot for more than half a second. “You boys get the table.”

Try as she might to balk at whatever the sheriff intended to do with a table, the endless string of guffawing laughter thwarted any angry protest. Monstrous though Mackleroy was revealing himself to be, Lola couldn’t entirely fault the man for treating her like an unruly teen. She shouldn’t have been so ticklish, a little bit perhaps, but not to such excruciating levels. It was ridiculous, a woman who’d been around as much as her and done the things she’d done, lived the life she’d lived. The very idea of being reduced to a witlessly laughing mess, and so easily too, it was beyond infuriating. If it were any other woman chained up in that basement the pleading, twisting captive would have had no pity. It would have been their fault for being so sensitive, their fault for not being tough enough. Weakness deserved to taken advantage of. As far as Lola saw it; ticklish women should be tickled. Except for her, of course, that was as unjust as it was unfair.

While Carson and Whitmore disappeared into shadow behind the stairs, their boss seemed determined to prove age hadn’t slowed him any. Scurrying his pinching digits up to the frazzled blonde’s lower ribs, the rosy hue of her cheeks quickly spread to her stretched neck. Yelping and jumping from every rough handed pinch, Lola forgot all about the deputies and their table, instead struggling to pull her arms down as that light sheen of sweat across her chest grew thicker. Her fractured pleas going unanswered, the inability to protect herself was maddening as Mackleroy spidered his fingertips along the undersides of the blushing blonde’s jiggling breasts.

“AIIEHAHA! NOEEEIEEE!” Rocking her arms furiously, unstable giggles exploded into wailing laughter as the voluptuous victim’s boots stomped hurriedly against the rug. Turning sharply, Lola pivoted away, the sheriff’s frolicking fingers continuing to tease under her arms, around her back and once again across her bosoms when she came back around.

Caught in a whirling, spinning cycle of cackling mayhem, all the buxom woman’s limited freedom achieved was to offer up more of her hypersensitive skin up for attack. Just as she would have done if it had been some other dreadfully ticklish girl strung up there, Mackleroy didn’t even have to move a single step to explore every inch of the pitiful woman’s body from beltline to underarms. When Lola turned her back the old man would goose her ribs and claw at her sides, when she turned side-on he’d rake short nails down whichever exposed hollow was nearest. Facing him again meant the sheriff had full access to her bouncing bosoms, a fact he reveled in by speedily stroking her appallingly sensitive nipples.

Whether the table was buried behind a bunch of junk or the deputies decided to hang out in the shadows, it took far too long for them to return. Lola was in no rush to find out what the wicked trio of lawmen had in store for her next, yet by the time Mackleroy started drilling a fingertip into her belly button she was longing for a break like never before. Held from behind with one arm coiled under her pushed-up breasts, the howling blonde kicked in agony as the sheriff’s lone digit vibrated deep inside her navel. Thick hot beads of sweat were snaking down the ballooning sides of her bulbous breasts, a crazed look permanently plastered across the trapped blonde’s reddened face.

“Got yourself a bucking bronco there, sheriff!” Deputy Carson quipped as he finally emerged from the dark. One end of a thick wooden coffee table in hand, the brawny man walked cautiously backward.

“I bet she’s a hell of a ride!” Whitmore appeared a second later while carrying the other end of the rather hefty table.

“If you’re lucky I’ll let you find out.” Mackleroy held tight as the breathless woman shook desperately in his grasp. “Now get that thing down here and let’s get her sorted.”

“Ah-ah-ahh! N-no-ah…please!” Lola blubbered between deep, raspy gasps when at last the sheriff stepped away. What she was begging for precisely was unclear, her mind clouded by the older man’s rigorous onslaught, but as the deputies set the heavy table down beside her the ravaged Amazon knew she had no interest in whatever was next.

“Legs up!” The cruel cowboy’s hands clamped around her ankles and began to pull.

“N-nono!” Tugging forward, the breathless, blushing prisoner hadn’t even noticed Mackleroy crouching down behind her.

Standing up and moving backward, the cunning sheriff dragged his panicked captive’s boots into the air. As she twisted and fought to break free, Carson and Whitmore shuffled their weighty wooden table beneath Lola’s jerking legs. Once the table was set in place, Mackleroy lowered her back down, leaving the panting detainee no choice but to kneel upon the flat surface as he pinned her ankles upon it. In quick, practiced fashion the two deputies then unclipped a pair of handcuffs each from their belts and moved in to assist their surprisingly strong boss.

There it was again, that familiar metallic clicking. It was a sound that could turn Lola’s stomach to knots on a good day, and as she felt the hard touch of steel through the leather around her calf muscles she could scarcely remember a time it had frightened her more. Right above the top of her boots the two deputies wrapped their pairs of cuffs, each one almost at the limit as they clinked shut. Pulling her ankles back a little more, the wincing woman was forced to lean forward, her feet dangling off the edge of the table as Carson and Whitmore secured the open ends of their handcuffs to the table legs behind her.

“Mackleroy! Mackleroy, PLEASE!” Lola strained to look back, jolting suddenly when she felt the two younger men start to fidget with the zippers that ran down the sides of her boots. “I’ll snitch! I’ll tell you anything! I’ll wear a wire!”

It was the lowest of the low, something even a career criminal could take pride in not doing. Ratting on others, siding with the law, only the scummiest of scumbags could bring themselves to snitch. Real outlaws would sooner do hard time, years if necessary. And Lola would have, five years, ten, a lifetime behind bars if it meant never being tickled again. Free food, a bed, maybe a skinny little cellmate to boss around. There were enough warrants out in other states for the topless fugitive to get a long stretch. As her boots loosened and the zips came down she decided turning herself in, even if it did require the indignity of ratting first, would be more than worth a halt to her misery.

“If we wanted you to be wearing a wire-“ Mackleroy wandered around to the front end of the table. “You’d be wearing a wire.”

“Sheriff, please!” Staring the wiry man directly in his pitiless eyes, the whining prisoner curled her toes as she felt her boots start sliding away. “Y-you don’t have to do this! I’ll get you something good, whoever you want! The bikers, their bosses, anyone! All of them!”

“Heh.” The sheriff smirked and maintained eye contact as he said. “Take her socks too.”

“NONO! Come on, PLEEEASE!” Lola thrashed hard, harder still when she felt her boots slip free.

“Ticklish feet?” Mackleroy poked the tips of his index fingers into the bound woman’s ribs.

“Eeieieheehee! Nohohoho!”

Torn between the devil’s digits prodding at her sides and the feeling of her thin black socks in the open air, Lola looked back just in time to see Carson and Whitmore toss her boots aside. Unstoppable girlish giggles caused a fit of squirming, the sheriff’s fingers unavoidable as the deputies hooked a finger each under the tops of her socks. Begging more to keep her feet covered than for the rib tickling to stop, the fearful captive’s wide smile betrayed the soul crushing horror she felt within. Squealing louder and pleading more intensely, Lola shook and tugged and strained as her socks were slowly peeled back, her marshmallowy soft heels painstakingly exposed. Gradual as the removal of her socks was, it was still happening much too fast for the crazed woman’s liking.

In unison the two men kneeling behind her plucked both socks free, and just like that Lola’s slender feet were out in the open. Spread apart and upturned as they were, the fretful crook knew there was not a thing in all the world that could protect her bare and vulnerable soles. Curling her long toes, the struggling captive continued to giggle mindlessly even as abject terror turned her firmly restrained limbs to quivering jello. It was then, stricken by dreadful anticipation and squeaking with the sheriff’s fingers prodding at her ribs, that the big breasted prisoner thought of Roy.

It was some small mercy that the numerous memories of her current boyfriend had stayed silent throughout most of the basement ordeal. Only staring down the barrel of what was rapidly turning into the worst tickling of her life did Lola finally think of Roy’s god awful antics. Until that exact point, bound, half naked and bare foot at the whims of those three cops, Roy Wenterlant had held the inglorious title of the curvaceous criminal’s most merciless tickler. For nearly eighteen months the small time conman had kept his Amazonian lady in line, his initial charms soon giving way for the sadist he was behind closed doors.

Lola had fallen for Roy just as the notably absent Deputy Stephanie Armstrong had before her. And, just like Deputy Armstrong, she’d fallen victim to the smooth talking bastard’s sinister side too. He was all rebel charm, the dangerous bad boy, as quick with a smile as he was with a scheme. My kind of man, she remembered thinking when they’d first crossed paths, and the fact he’d romanced a woman of the law while leading the life he did only added to his appeal. Roy started slow at first, a poke to the side here, a stroke of the neck there. By the time Lola found herself tied to the seductive swindler’s bed she was in too deep with his various scams to think about escape.

Two months into their relationship she’d taken what she could, their plans be damned. Like she’d done countless times before, Lola made flight in the wee small hours of the morning with a mind to getting out of town and never looking back. How Roy tracked her down she never did find out, some curious phone call from a contact who saw her skulking away most likely. In a town that small it wasn’t hard to believe, everyone knew everyone in one way or another. She’d stolen his car too, which admittedly probably did look rather suspicious.

Without a word from him, Roy had driven the apologetic blonde back to his place on the outskirts and escorted her rather forcefully indoors. Lola babbled the entire time, trying to find some version of events that would excuse why she ran and why she’d stolen from her so called boyfriend, of all people. He was having none of it, the slick operator’s normally jovial demeanor nowhere to be found. She’d seen Roy be mean before but never like that, never that quiet, expressionless fury. When the handcuffs came out she’d begged and begged, and begged more still once her boots came off.

The navy boys, the skuzzy landlord, even that one truck driver she’d hitched a ride with through half of Missouri years before, none of them held a candle to Roy Wenterlant’s cruelty that morning. He’d been cruel before, that much was true and it was most of the reason why’d Lola had tried to run, but it never reached the point of outright torture. As much as she hated being tied up and tickled by him those first two months together, the slick-haired criminal had at least maintained an air of playfulness. There was no playfulness after she’d stolen his car. Roy had simply placed a pillow over her shins, straddled the handcuffed woman’s ankles and went about running his fingertips around her bare feet until she lost her voice and beyond.

It occurred to Lola then, as deputies Carson and Whitmore hovered near her bare feet like hungry vultures, that perhaps it had been Roy who’d told Sheriff Mackleroy how best to make her suffer. Too afraid to try running again after that first failed attempt, the half naked outlaw now wished she’d found the courage to get out from under her man those last sixteen months. How could she, of course, with almost daily reminders of what he’d do to her, and tying her up at least once a week for good measure. There was no escape. There never had been.

“Royyeehheehe! Royeeeiihaha!” Lola shook her head, thick mane of blonde hair whipping about her face as the sheriff crawled his index fingers up her ribs like caterpillars.

“You think he’s coming to help you?” Mackleroy leaned back and folded his arms. “There’s only two other people outside of this building who know you’re here, and Roy ain’t one of them.”

“Nuh-no...” Blowing a few strands from her weary face, the buxom captive breathed heavy. “I know it was him….he-he set me up.”

“Got it all figured out, do you?”

“Why…why now?”

Frowning, the sheriff closed one eye. “I appreciate you got no reason to believe a word comes outta my mouth, but your dimwit of a boyfriend hasn’t the slightest god damn thing to do with any of this.”

“Then…then…” Lola’s voice trembled as she looked up at the old man, all puzzlement across her bright red face. “Then why? Was it the scrappers or…the café thing…or…”


“Nono…she wouldn’t…she wouldn’t say anything…”

“Way she tells it, Steph tried to warn you.”

“Oh….no.” The topless prisoner’s bottom lip shook.

Stephanie Armstrong’s humiliation in the back country was so total, so absolute, Lola scarcely ever thought for a moment the diminutive deputy would say anything to anyone. How she had even broached the subject with her fellow officers, the fear struck blonde couldn’t begin to imagine. It made sense now, it all made sense in the most devastating, apocalyptic way. What a fool she’d been, if not for accosting the deputy than certainly for admitting their shared experiences with Roy at the time. Experiences Armstrong had no doubt conveyed to Mackleroy and the rest. A damn, stupid fool.

“Tickle her feet, boys.” The sheriff said.

“NO PLE-“ Lola began and so too did Carson and Whitmore, both of them pouncing upon her tissue soft soles with swiftly stroking fingers. “EEEEIIIIGGGHHAAA! AAAIIEEHAHAHA!”

Arching her back, the shrieking detainee rocked with such force that the heavy table below tipped a full inch off the floor. From a horrified stare to bug-eyed hysteria, Lola’s whole face turned in one berserk instant. Each deputy danced ten digits around the bottoms of both the flailing woman’s rapidly shifting feet, the handcuffs catching noisily on her ankles over and over as she tried to pull away. Through manic fervor her large naked bosoms bounced wildly, stomach heaving as shrill cries of laughter echoed off the walls. In a blurred whirl of flying hair and crazed movement, Lola caught flashes of the stoic sheriff, standing idly by as he watched the first few terrible seconds of her hyperticklish agony.

Planned or not, the two crouching men at her back had no synchronicity, their differing techniques making the torment all the worse. Whereas Roy was only one man and his hands would more or less do the same thing at any one time, Whitmore and Carson could split Lola’s massively fractured attention more than it already was. Short nails raked up her high arches and fingertips slid over the balls of her feet, demonic digits buried under her toes and spidered across the bewildered outlaw’s insteps. While one man stretched her toes back and kept her foot from moving, the other scurried fingertips around a wrinkly arch, the appallingly sensitive skin quickly turning pink.

Lost to the hectic hell that was her own ticklishness, Lola didn’t notice in the slightest when the sly-handed sheriff started to unbuckle her belt. Laughing wordlessly in ballistic dismay, there was nothing left of the broken woman’s mind to focus as Mackleroy unbuttoned the top of his latest victim’s pants, unzipped her fly and revealed the dark red g-string panties beneath. Only when she felt a tug at either side of her tight leather pants did the unhinged woman recognize the stealthy undressing, and even that was somewhere deep in the back of her desperately disordered thoughts.

Using a thumb at either side, the mustached cowboy hooked the howling prisoner’s pants and panties both behind the waistline. Between her uncontrolled movements and the effort Lola spent fitting her well-curved ass into the leather each morning, sliding the practically painted-on pants off perhaps took more effort than the sheriff had expected. Sure enough however, with some gritting of the teeth, Mackleroy was soon able to inch the cackling crook’s last two pieces of clothing around her plum shaped behind and down to her thighs. All but nude now save for her long legs, Lola’s gyrating bare butt and smooth shaven pussy were out in the open for all present to admire.

Being naked and tied and tickled out of her mind was sadly not a new experience, nor was being tickled by two handsy men at once. Never before had all those factors combined at the same time, and it was a great deal more awful than the poor prisoner had dared to imagine. Tragically, it was only a few seconds later that Lola learned what it felt like to be naked, tied and tickled by three men in unison and the result was abject insanity. Starting at her madly thrusting hips, Mackleroy pinched up the breathless blonde’s slender sides and down again, her Amazonian body shaking like she were on fire.

Unable to pry her thighs apart due to her own tight pants being wrapped just above her knees, the hysterical criminal’s lower legs spread awkwardly out to her bare, bound feet. Restrained in every direction and woefully outnumbered, Lola’s soles were turning a darker hue of raw pink where the deputies’ fingers continuously ran without rest. Higher up her struggling frame, the sheriff’s bony digits were sure to roam across every inch of nightmarishly ticklish, sweat gleaming flesh they could find, certain to flicker over the tattooed woman’s nipples with torturous frequency. Devolving into a creature of pure tickled madness, the excruciatingly straining plaything couldn’t have mustered the mental capacity for begging words even if she’d been physically able.

“If only you could turn back time, eh Lola?” Mackleroy leaned close and scribbled his fingertips down the trapped woman’s arching back and onto her flexing butt.

“YIIIEEEHAHAHA!” Jerking forward sharply, the old man’s devious fingers feathered gently between the screeching captive’s cheeks, deep dimples forming at as she squeezed.

“’Course you’d have probably ended up in here eventually.”

Carson chuckled, though their demented victim was too far gone to register any of the trio’s conversation. “Heck, if we’d known you were this much fun we’d have had you down here every week!”

“Think we better have a chat with Mr. Wenterlant after this.” Deputy Whitmore added as he held Lola’s middle toes open and drilled a finger in between. “Keeping you all to himself, he oughta know better.”

“Roy ain’t on the agenda.” Said the sheriff while running his digits around to the soft spots between the furiously bucking woman’s hips. “He don’t matter to the powers that be, their only interest is right here.”

“Still shitty of him not to share.” The youngest of the men grumbled. “At least the bosses let us have a round with her first though.”

Mackleroy lifted one hand back and looked at his watch, his remaining five fingers left to prance impishly around Lola’s puffy pussy. “Speaking of, better get your licks in soon if you’ve a mind to.

“Don’t mind if I do.” Deputy Carson planted his large hands onto the coffee table and hoisted himself up. “Keep at her feet, Whitmore. You can go next.”

“Think she’ll have any energy left for a blowjob after this?” Said the former quarter back as he moved one hand over to the ravaged prisoner’s other bare sole.

While Mackleroy moved his attentions up from Lola’s pussy to her vulnerable underarms, the bulky deputy at her back had already drawn his trousers down below his hips. Though she could not see Carson’s large pulsating cock as he swung one leg over the table and her lower legs, she did feel it when he pressed against her ass. Rock hard between her butt cheeks, the brawny man slid his slick and throbbing erection comfortably into place, his big paws wrapping around the disheveled woman’s waist and pulling her close. Sliding his hands up as he thrust and grunted, the muscular man’s fingers pinched across Lola’s heaving ribs, cupped firmly around the sides of her large squishy breasts and immediately set about fondling her nipples with merciless glee.

Every vein in the mindlessly laughing blonde’s forehead and neck stood out, sweat dripped off her aching jaw and, though she had not cried in near thirty years, tears rolled from her unblinking eyes. Deputy Whitmore’s skillful fingers skated freely around Lola’s soles and the undersides of her spreading, tightening toes, his boss’s digits performing the same unhindered evil beneath her arms. Carson, with his great bear-strength wrapped around her from behind, continued to pleasure himself against the helpless jailbird’s shapely behind all the while sending anguish through her hopelessly ticklish nipples. Seconds were minutes and minutes were hours and the whole unendurable horror continued until burst after burst of thick hot cum shot up the curved small of the blonde’s back.

“God….DAMN!” The bald headed deputy exclaimed as his hard thrusts slowed and all three men finally relented their teasing fingers. “I’m inclined to agree with Whitmore…ahh…” Carson stepped back, leaving a mess of white lust splattered over Lola’s back and the top of her ass. “That asshole Roy should have told us about her sooner.”

“If it’s any consolation-“ Mackleroy reached overhead to the handcuffs. “I’m pretty sure Wenterlant’s never getting his mitts on her again.”

That was a nice thought, or it would have been if Lola’s tickle-addled mind could have made sense of it. Wheezing and whimpering incoherently, the dreadfully degraded woman barely fought back as the wiry sheriff pulled the cuffs from the carabiner and lowered her bound hands. As she collapsed into the older man’s arms, Deputy Whitmore unlocked the other handcuffs that were held around her ankles. Sadly, the hunky young man didn’t set her free due to some sudden kindness, her feet dragged a moment later across the tabletop as Mackleroy lifted her forward.

“Your turn, Sheriff?” Whitmore grabbed at the dazed captive’s pants and pulled, stripping her entirely nude.

“You go ahead.” Said the remorseless cowboy as he lowered the now stark naked prisoner to the rug. “Besides, I’m plenty content getting mine at home with the wife.”

Carson looked up while pulling the coffee table away. “Does Mrs. Mackleroy still even laugh anymore, Sheriff?” He set the table beside the stairs and stood back to his full, imposing height. “After all these years hasn’t she got used to your…affections by now.”

“Don’t work that way.” The old man rolled his shuddering, twitching mess of a detainee on to her back. “Mrs. Mackleroy still laughs plenty. Was a long time ago she gave up on begging me to stop, but the laughs come all the same.”

Deputy Whitmore began unbuttoning his shirt. “Isn’t their begging half the fun?”

“Sure, but it ain’t all about the words.” Mackleroy took hold of Lola’s wrists and pulled her arms up and over her head, only the tiniest amount of resistance making her tattooed muscles flinch. “You take a look in my wife’s eyes when I tickle her. Hell, look at this one here. Just cause they ain’t screaming ‘no no, stop!’ don’t mean the message isn’t there.” He kneeled down at the edge of the rug and pinned the bound woman’s arms to the floor.

“I just can’t believe you don’t get bored tickling the same woman, year after year.” The dark haired Adonis’ shirt and undershirt both were at his feet. Unbuckling his belt, the topless deputy’s chiseled abs and steely pecks flexed.

“Then you are missing the point, Grasshopper.”

Deputy Carson wandered over to join his cohorts on the rug. “What the sheriff’s saying is, you tickle someone once or twice they’ll be upset but life goes on, right?” The big man looked to his boss who nodded in the affirm. “Now, you tickle someone week in, week out for years on end. A decade now, for the Missus?” The mustached lawman nodded again. “Imagine the toll that takes on a person. Imagine Mrs. Mackleroy’s state of mind these days.”

“Oh, I get it…” Whitmore stepped out of his now crumpled pile of pants and motorcycle boots, the young man’s huge, manscaped cock throbbing eagerly and erect. “You’re playing the long game.”

“Anyone can torture a body, Deputy.” The sheriff’s grip tightened a little more around Lola’s forearms as the nude young man stepped over her writhing, sweat-soaked body. “It takes an iron will to keep someone else’s mind locked in hell.”

Whitmore towered in silence for a moment before lowering himself to his knees. Straddling the destitute woman’s ribs, the deputy’s well-toned rear end pressed into the upper half of Lola’s stomach, her gasping breaths restricted just a touch. Clamped between the strong lad’s thighs and what measure of weight he didn’t hold up himself, the poor prisoner’s entire torso was rendered wholly immobile. Just as she started to regain a modest amount of composure, the teary eyed criminal caught Deputy Carson out the corner of her vision, the big man maneuvering himself down toward her feet.

“n…no…” Lola managed, wincing a second later when Whitmore’s large hands cupped the outer sides of her large, bare bosoms. Unsure where best to put her admittedly foggy focus, it didn’t much matter as she couldn’t stop Carson from crouching near her bare soles, nor the man straddling her from sliding his thick cock between her breasts.

“Tickle tickle!” The youngest of the trio looked the terrified woman directly in the eye as he squeezed her fleshy boobs and thrust his shaft through her squished cleavage.

Unnerving as the deputy’s teasing words were it was his toothy, pearly white grin that really caused Lola’s skin to prickle. In time with that fiendish smile, Whitmore’s thumbs stood to attention and quickly curled inward, right toward the blonde’s painfully sensitive nipples. A strange, panicked kind of hoot-noise escaped the desperate woman’s lips and as those vile thumb-tips stroked across her areoles, so too did Deputy Carson’s fingers wiggle up the soles of her feet. A loud screech tore from Lola’s gaping mouth, her back arching what little it could under the muscular man. Her legs kicked and flailed, toes stretching and curling at random as the other officer’s digits chased close behind.

“AAAHAHAHAH! AAIIIEEHEEIIE!” Long, disheveled locks flying as she shook, the newly-crazed crook’s miniscule composure disappeared in an instant. Bellowing with laughter, every bit of struggling mayhem helped to rub Whitmore’s pulsating hard-on between her breasts, a fact the lantern jawed deputy clearly enjoyed. He no doubt reveled in sadistic joy from the contorting looks of agony across her face as well, the head of his cock slick and glistening.

Abandoning his hot pursuit of their quarry’s soles, Carson snatched both of Lola’s ankles and pinned her legs firm to the floor. Trapped entirely save for her rolling head, the howling captive jerked desperately at all four limbs, her legs becoming even less agile when the burly bald deputy pressed one of his knees down over the lower parts of her shins. Even at her most energetic the bewildered blonde would have had little hope slipping free, weakened as she was there was no chance at all. Try as she might, through pure instinct now more than any conscious effort toward escape, Lola kicked and pulled and yanked. When the big man’s deft digits danced up her arches all that effort meant just as much as it had a second before, her slender feet wiggling with nowhere safe from the terribly ticklish touch.

“Ngh!” Deputy Whitmore growled, his grip around the hysterical woman’s bosoms pressing a little tighter.

“YEEEIIGHAHAHA!” Tears drained down Lola’s dark red cheeks as the young man’s nimbly moving thumbs sped up the cruel flickering of her nipples.

“Ahn! Yeah!” Suddenly releasing her bulbous breasts, the nude lad’s hands darted straight for the blonde’s taut underarms, his fingertips scribbling right on the bullseye. He grunted again and his short nails raked down the shrieking woman’s hollows, his swollen cock shooting one thick load after another across her chest.

Riding out his orgasm, Whitmore’s fingers gradually slowed, though Lola’s laughter remained at an all time high. Deputy Carson, either unaware of his coworker’s climax or simply uncaring, continued racing all ten of his fingertips around the cackling captive’s soles. A minute, two minutes, even as the former football champion climbed wearily off of her the other officer showed no signs of relenting. With Mackleroy still holding her arms firm, the defenseless and cum-drenched outlaw continued to wail like a psych ward lunatic, the only pauses as brief as possible to gasp for much needed air.

Blurry eyed and quite firmly out of her mind, the thrashing Amazon had no idea Whitmore was taking his leisurely time to get dressed, sit on the stairs, strap up his boots. She had no concept of anything beyond Carson’s digits spidering up and down her feet, skating across her pillowy-soft balls and circling around her heels. He dug in under her toes and Lola rolled so hard to one side that her bare ass almost pointed directly toward the ceiling. When at last the bearded officer finally ceased, that raspy tinge in the voluptuous jailbird’s voice was present in every, deep draining breath and the tittering giggles that continued long after.

“Alright.” The sheriff tapped his wrist and with a little groaning and a hand on one knee, stood upright. “Let’s get her upstairs.”

“I got her.” Said Carson, who had been sitting on the coffee table for several minutes watching their prisoner wheeze.

Whitmore stood too, getting up from his perch on the stairs. The three lawmen gathered around their outstretched plaything who hadn’t so much as lowered her arms, even though the sheriff had released her wrists from his grip when the tickling stopped. With a stern, purposeful look about him, the biggest of the men reached down and put both of his great bear-like hands under Lola’s arms. It was only then, in shakily and much slower than normal fashion did the tattooed woman bring her hands down from above her head. Far from regaining her sanity, if that were still possible, the nude captive did little more than feebly squirm as she was hoisted up off the floor and slung head first over one of Carson’s brawny shoulders.

Dangling down behind him, her long hair and handcuffed hands swayed passed the deputy’s beltline as he turned toward the stairs. Whitmore and Mackleroy went first, the bald headed beast of a man taking a moment to securely curl one thick bicep around the backs of Lola’s thighs. Her bare butt protruding in the air beside his head, Carson evidently wasn’t done with the day’s torments as his free hand crept across one ass cheek. Flinching weakly, the frazzled woman squeaked almost inaudibly as the brutish officer’s five fingers crawled between her legs and stroked gently across her taint. Ascending the stairs, one jostling step after another, Lola twitched and squirmed the entire way back to the top.

Outside, the sunset was well into dusk. As the small house of horrors was left behind them, Deputy Carson persisted with his fondling, the busty and exhausted prisoner meekly squirming over his shoulder. Passing by the motorcycle, the patrol car with ‘Deputy’ on the side and the patrol car she’d arrived in with ‘Sheriff’ painted across it, the bulky man soon came to a stop at the far end of the dusty clearing. The persistent teasing of her taint halted, and Lola’s world turned upright as she was hoisted up and over only to be set down in what at first appeared to be a dark box. Looking up to a dimly orange and dark blue sky, the handcuffed and naked Amazon groggily realized she was laying in the trunk of an unknown vehicle.

“Til next time.” Carson smirked before wandering out of view.

A second later, Sheriff Mackleroy appeared and as Lola heard one of the car doors open. All the weight shifting, to her dazed and befuddled state of mind it felt like the driver getting out. No small occupant either, based on how much the vehicle raised up again followed by footsteps on the ground. Eyes fixed on the sheriff, the utterly perplexed blonde watched as the old man turned away from her worrisome gaze and acknowledged the new arrival.

“Sir.” Mackleroy’s tone was one of familiar respect.

“Mackleroy.” A tall, well-dressed black man came to stand beside the lawman. He was bigger than any of the other men in both height and muscle mass, with even less hair atop his head than Deputy Carson. His cold, haunting eyes cast down over the tattooed woman in the trunk. “Caught another criminal?”

“Completely remorseless, this one.” Said the sheriff. “Still hasn’t learned her lesson.”

“A good thing then…” The big man put one great hand up on the open trunk lid and slowly bought it down, the light inside fading to total darkness. “That I happen to be an excellent teacher.”

The End​
Hot! Your stories getting darker and darker ;). Loved this one although I usually dont like stories where the ticklee is oder than me ;)
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