(This story is also available as a downloadable file in my "Story Archive" thread.)
The sheriff smiled happily as he admired his latest catch. Ashley was bent over his punishment bench, stark naked and secured by leather straps. Her head was down, her ass high, and her long, tapered legs were spread wide. Her firm buttocks were separated, giving a clear view of her hairless mound and small pink asshole. The outer lips of her pussy had parted to show the delicate labia within, and both her openings glistened with lubricant, evidence of the humiliating strip and cavity search he had recently given her. He always conducted his searches in the front room of his station so that the townsfolk could watch through the window as he diligently probed his suspects, and the ordeal had been filmed by multiple cellphones.
He normally left his victims in a holding cell until their transfer to the prison farm, but Ashley was a special case. The lovely lawyer was not only an exceptional beauty - she was one who had been in his custody several times. Today he had decided to have a "chat" with her.
After the search he had taken her to his "interrogation room" - a former supply closet that had been renovated for a far more interesting purpose. Ashley had waited anxiously as he filled out paperwork in his office, knowing full well what would happen on his return. The wall opposite her was hung with a variety of instruments designed to inflict pain on the tender tushies of those who came into his clutches, and she had plenty of time to inspect the various straps, paddled, canes and floggers, wondering which he would use on her and how much they would hurt. Thanks to the approval of the townsfolk and the legal rubber stamp of Judge Search'em, the sheriff had full license to deal with miscreants as he saw fit.
One section of the wall held a different kind of device - dildos, buttplugs and vibrators. There were a few gags as well, though these were seldom used. The sheriff liked to hear his victims scream and cry, he only gagged those who annoyed him with their indignant protests. "A woman should submit to her punishment gracefully!" he liked to say. "Just because your ass is getting tanned doesn't give you the right to get bitchy!"
She could hear him whistle happily as he lovingly rubbed an oiled rag over the heavy leather strap he had named 'Old Betsy'. She had felt its sting on many occasions, but today it would only be the beginning of her troubles. A session in the interrogation room meant more than a mere spanking - she would be his plaything for as long as he saw fit.
The sheriff dropped his rag onto a small table and swished the strap through the air. Ashley shivered at the sound, her bottom tensing in anticipation.
"Do you know why you're here Ashley?"
"Uh, I was speeding, sheriff."
"Wrong."
The strap whooshed as he swung it around.
*SMACK!*
"AHHHH!" Ashley yelled, her slim body jerking against her restraints. Betsy had hit across the centre of her backside, sending ripples through her soft flesh. He paused to admire the wide red stripe that formed on her milk-white skin.
"That's not why. Well, it's part of the reason, but we both know there's more."
"I made a mistake. I didn't see the speed limit. That sign is covered by bushes - "
*SMACK!*
"OOOOOOWWWW!"
"Don't be silly girl. You've been here before, you know it drops from thirty-five to fifteen in front of my station. Sign or no sign, it's the law. And you are a lawyer, aren't you?"
A lawyer who has no legal rights in your county, thought Ashley grimly. "Yes sir, I am."
"So you should know better, shouldn't you?"
Ashley sighed. "Yes, sir."
"Indeed." He rubbed the strap over her burning bottom, letting her feel the supple leather that was being used to punish her posterior. "Funny how you smart girls seem to miss the simple things. Guess you think you're too important to follow the rules like the rest of us."
Ashley tried to think of an answer that wouldn't result in another swat - but she knew it was futile.
"I'm not too important sheriff."
"Good. Then you won't be making any fuss about taking your punishment!"
*SMACK!*
"EEEEaaaahhhh!"
The burn was worse now, each stroke building on the last. Her hands clenched as she tried to distract herself. "Gnnnnn!" she moaned.
"Nothin' like a good strapping to put a girl in her place, don't you agree?"
Ashley rolled her eyes. "Yes, sir."
*SMACK!*
"OOOOOOOOHHHHHHH!" Her legs twitched and she bit her lip. That stung so bad!
"But as I was saying," he continued. "That speeding ticket isn't the real reason you're here."
A large hand caressed her throbbing ass, feeling the warmth of her glowing behind.
"You're here because you're playing the game."
Ashley frowned. "What game!" she asked innocently. "I don't underst - "
*SMACK!*
"EEEEAAAAGGGG!"
"The game we always play, Ashley. The one that keeps me in this job when I could have retired years ago. The one that keeps you coming back for more. The game of cat and mouse."
"I'm here to speak to a client!" Ashley retorted. "I'm on legal business!"
*SMACK!*
"EEEEEEEEEEEE!"
"And what kind of business is it that you couldn't do over the phone, or the internet? And if you really had to see someone in person, why not have them come to you? Since when did lawyers make house calls?"
Ashley said nothing. It was true - she could have had Jane Saunders visit her office. She could have conducted her business on the other side of the county border, out of the sheriff's jurisdiction. So why had she driven to her client?
"I, um... I like to give personal service," she replied lamely.
"Ha! You sure do! This will be your third visit to the farm, won't it? And you'll be giving plenty of 'personal service' down at the truckstop!"
Ashley flushed crimson. The truckstop/brothel was famous throughout the state. Any attractive woman given a sentence at the local prison would be working shifts for the entertainment of the locals, both on-stage and on her back. She had lost count of how many men she had been forced to entertain.
"You make me do that!" she responded. "I don't choose to be a whore!"
*SMACK!*
"AAAHHHH!"
Ashley wriggled in her bonds, trying to shake the pain away. Her ass was now red all over, testament to the effectiveness of Old Betsy.
"Don't lie to me girl. You think I'm stupid? Seems we need to crank things up a notch."
The sheriff walked to the wall and hung Betsy back on her hook. He chewed his lip while examining the various implements. "Did you get paddled at school Ashley?"
"Yes, sir."
Like any pretty girl in a southern state, Ashley had caught the attention of her principal. He had frequently invented excuses to administer discipline to her young bottom, and grabbing her ankles in his office was a regular part of her education.
"Good! Then this should feel like old times!"
He took a wooden paddle from the wall. Holes had been drilled through it to reduce air resistance, allowing for a faster swing - and a much more painful swat.
"He give it to you bare?"
"Of course, sheriff. Girls always got it bare."
"Just as it should be." He stepped behind her and patted her crimson cheeks. "Nothing like a bare-ass whoopin' to teach a young lady, isn't that right?"
Ashley shuddered. She had never forgotten the feeling of a paddling, and now she was going to be given an unwanted reminder. "Yes, sheriff, it taught me to be a good girl."
*WHACK!*
"YEEE-OOOWWWW!" Ashley's cry of pain was much louder now. The impact of hard wood on her already burning bum was much worse than the strap. Tears filled her eyes and trickled down her cheeks.
"Where was I? Ah yes - the game." He tapped the paddle on her quivering buttocks. "See, you know what to expect when you come here, Ashley. You know how I run this county. You also know that driving through town in that red convertible of yours makes you pretty conspicuous. So why do you do it? Why take the risk?"
"Because..." Ashley thought hard. "Because I'm not going to be intimidated by a misogynistic redneck like you, sheriff!"
*WHACK!*
"WAAAAAHH-HAAAAA!!!" She couldn't hold back the sobs that punctuated her anguished wail. Her ass had been tenderised, red and swollen by repeated punishment. Her body shook as she started to cry, tears flowing down her cheeks.
"I resent that comment. Not the redneck part - I'm a country boy, and proud of it! But misogynist? That's just rude. I LOVE women! Nothin' more pleasing to me than the female form - or the female fanny!" he chuckled at his own joke. "Believe it or not, Ashley, I have a great affection for girls like you. Sexy, sassy - and good earners! I make a pretty penny from your shifts at the truckstop. Not as much as you do with your lawyerin' - the folks round here don't have much to spend - but still, I've got a good retirement fund thanks to you and your friends. Judge Fields for example - she's a favourite with the boys. Took a good leathering to break her in, but once she learned her place she sure brought home the bacon! You skirt-suit types make the best working girls."
Ashley sniffed back her tears. "Th- that's because you s-set our quotas so high!" she stammered. All the women working at the truckstop had a daily earnings quota to meet, or else face punishment when they returned to the prison.
*WHACK!*
"EEEEEEEEEE!!"
"I only set it so high because you're worth more! Can't expect a plain girl to turn as many tricks as a beauty like you, can I? That wouldn't be fair, would it!"
The concept of "fairness" didn't seem to have much consideration in StripSearch County, but Ashley didn't think it wise to point that out.
"But I'm getting ahead of myself." The paddle tapped against her bottom, making her flinch. "Fact is, you come through here when you don't need to. And don't tell me that you don't know what to expect - we all know how I run things around here. But that's part of the game, isn't it? When you drive down main street I bet your fancy little knickers are soaking wet. You know I might pull you over at any moment - and the stirrups in the front room are always waiting for you."
Ashley was well aware of that. Strip and cavity searches were the sheriff's main source of entertainment - and a source of amusement for the locals. There wasn't a man in town who hadn't seen her naked and spread out. Plenty of the women liked to watch the fun too.
"Gives you a thrill, doesn't it? You know there's a chance - just a small one, but a chance nonetheless - that you'll make it through town. I bet you go home and frig yourself silly, thinking about what would have happened if you got caught."
Ashley bit her lip. It was true, although she would never admit it in front of him. She often stripped in her bedroom, imagining that she was being ordered to do so. Her own fingers were much smaller than the sheriff's, but she explored herself eagerly as she played the scene out in her head.
"Remember the time you tried to stop one of my drug sweeps?"
"Y, yes, I remember."
Ashley could never forget that day. She had received a frantic call from a client who was about to be stripsearched under a "Jane Doe" warrant that gave the sheriff license to search any woman on the university campus who wasn't a student or staff member. She had managed to get a temporary restraining order while the warrant was reconsidered - but things had not gone to plan. Her client, along with nine other women, had been forced to kneel naked over a bench in the search position for a whole hour while the issue was reviewed. A few minutes before the order was due to expire, the Judge had faxed through his decision. Not only had the search warrant been upheld, but since Ashley herself fell within its description she had been ordered to strip and take her place alongside the others!
"What did you expect?" asked the sheriff. "You knew the case would be reviewed by Judge Search'em - and he was the one who gave me the warrant in the first place! You think he was going to cancel his own orders?"
"I... I was doing my job!" said Ashley lamely.
*WHACK!* The Sherrif laid another painful swat on the trembling bottom of the luckless lawyer.
"OOOWWWWW!"
"You shoulda known what would happen!" he lectured. "But there you were, dressed to the nines, just puttin' yourself in my reach. And you came hard, Ashley, don't deny it. Got it all on video!"
Ashley's ears burned. The humiliating ordeal had been recorded, each woman brought to orgasm during her searches. None of them could ever live it down.
"But that's what you really want, isn't it? You high-class ladies love to be taken down a few notches. That's why you do so well at the truckstop - because you get to be cheap and slutty while pretending it ain't your fault!"
"That's not true! I don't - AAAAAAHHHH!!!"
*WHACK!* The paddle smacked her ass again, cutting off her protest.
"Don't lie to me girl! Nobody fucks like you do. Most women wouldn't be able to walk after the reaming you take during a shift. But you - you can take it easy, because it Gets. You. WET!"
He punctuated the last three words with hard smacks on her defenceless derriere.
"AHH! OWW! AAAHHHHGGG!" Ashley screamed each time the paddle punished her posterior. Her buttocks were on fire, the glow spreading through her body. "Bwaaa-ha-haaa!" she wailed.
The sheriff walked to the wall again. She forced herself to look - she had to know what was coming next. The paddle was hung back on its hook, and she shivered with anticipation as he took his time choosing. Would it be the single-tail lash? The riding crop? The cane?
But it was the sex toy section that he reached for. Two huge vibrators, black and ridged. She swallowed hard. Taking one up her pussy would be bad enough, but there was no doubt as to where the second one would be going.
"Most women think these are too big," he mused. "But a pro like you - I reckon you can handle it."
Ashley tried to swallow the lump in her throat. Having her body searched was one thing, but these would stretch her to the limit! She tried to relax and prepare herself. Resisting only made things worse...
The sheriff stepped behind her again. A quiet buzz announced that he had switched on one of the vibrators. Ashley twitched as he rubbed it over her pussy.
"That's a lovely laser job they gave you. Not a hair to be seen, just smooth, soft skin."
All women sent to the prison farm received a complimentary lasering to ensure they were always picture-perfect for their clients. The permanent removal of their pubic hair was a reminder of how they had been put in their place - not that they were likely to forget it.
Ashley sighed. She could feel herself responding to the stimulation, a tingle spreading through her nether regions. The tip moved to her entrance, teasing her. She closed her eyes and took a deep breath. Would he thrust it in hard? Or give it to her slow? The sheriff liked to be unpredictable - he knew it kept his women in suspense. The pressure grew as he pushed forward, and her lips parted to admit the rounded end of the huge sex toy. She was being opened, stretched, filled...
"You sure are a tight one Ashley!" he said with satisfaction. "I bet you do those pelvic floor exercises, don't you?"
"I... *ahh* um... yes..."
"Course you do! A woman like you - you'd be embarrassed to have a loose pussy. That's one of the things I like about career women - they really take care of themselves." The vibrator worked its way deeper. "You eat right, you go to gym, you get your hair and nails done - everything perfect."
"Ahh.. th..thanks," mumbled Ashley. Most of her attention was taken up by the slow invasion of her love-tunnel - she wasn't in the mood for small-talk. God, it was so big!
She moaned softly as he pushed the vibrator all the way into her. "Oooohhhhhh!" Her body was clamped tightly around it, increasing the sensations from the buzzing motor.
"And now for door number two!" chuckled the Sherrif. "Going to be a tight fit, but you know how to take it up the ass, don't you?"
She did indeed. Ashley's gorgeous behind was her best feature, according to the men who paid for her services. There wasn't a single day she worked the truckstop without getting rogered senseless. Consequently, she was well experienced in how to open herself up and submit to a buggering. She pushed out with her ring as the second vibrator nuzzled against her sensitive asshole.
"That's a good girl!" said the sheriff admiringly. "Won't hurt a bit if you cooperate!"
Ashley wasn't so sure. She had taken plenty of impressive cocks from well-hung working men, but the male appendage was more flexible than the rigid plastic being forced into her rear entrance. "Mmmmmmm!!" she exclaimed, trying her best to accommodate the unwelcome intrusion. Her asshole was stretched wider, wider...
"Aaaahhhhh!" she gasped. "S-slowly! Please!"
"As you wish!" The Sherrif was in no hurry. He was also mindful of Ashley's value when turning tricks - he wasn't going to risk damaging her most popular attraction! The vibrator worked its way past her sphincter and slid easily into the space beyond.
"OOOOOOHHHHH!!!"
With her pussy already occupied, there wasn't much room inside Ashley's body for the second toy. She was more full than she had ever been, the artificial cocks buried deep inside her. She wriggled against the straps that held her down, trying vainly to relieve the pressure within.
"Steady now!" The Sherrif placed one hand on her back to settle her. His other hand reached between her legs, his skilled fingers teasing her clit. She was already wet, and he had years of experience. They both knew that her orgasm was just a matter of time.
"Don't fight it Ashley." His tone was gentle. "But I don't think you really want to, do you? You have to fight at work - you have to prove yourself to the men, work harder just to get respect. But you don't need to do that here. I'm going to treat you like a wanton slut - and you're going to enjoy it."
Ashley whimpered. She could feel the warmth spreading through her body, the slow build toward a shameful climax. She was putty in his hands, just a hot piece of ass to be used and sold. But more than that, she knew that everything he had said was true.
She chose to visit his county. She chose to put herself at risk. She kept herself in top shape because she loved to be desired. She knew what would happen to her when she fell into his clutches, and how she would be put to work at the truckstop, selling her body to lecherous men.
And she loved it.
The simple fact was, her job was intellectually challenging but emotionally unsatisfying. The men she met at work were patronising to her face and jealous behind her back. The few that she took to bed were self-absorbed and inconsiderate. As a woman, she was expected to be beautiful and sexual - but was labelled a slut if she actually wanted sex. Being the sheriff's prisoner was paradoxically liberating. She thought of all the cocks she would suck at the truckstop, all the men who would bend her over the hood of their cars and take her roughly from behind. Her body writhed and her pussy spasmed as a powerful orgasm took hold of her.
"OOOOOOHHHHH YEEEEESSSSSSS!"
Her scream was unashamedly loud. She gave full voice to her passion, not caring about the spectacle she was making. The sheriff had seen every part of her, explored every nook and cranny. She had no secrets from him, nothing to hide.
When it was over she relaxed, slumping in her bonds and gasping for breath. She barely noticed as he ceased to rub her clit and switched off the vibrators. The sheriff stepped back to admire the view. Her slender body glistened with sweat, her toned bottom was red and swollen. Juice dripped from her pussy and fell to the floor, filling the room with her scent.
"And that's why you play the game, Ashley. Because, deep down, you want to lose." His voice was filled with smug satisfaction.
Ashley panted heavily. She was exhausted from her struggles and spent from the powerful orgasm that had ravished her body. It was a few moments before she could reply.
"That's where you're wrong."
She turned her head and looked back over her shoulder. Her long blonde hair was in disarray, her makeup streaked by tears - but her eyes were sparkling.
"I don't 'lose', sheriff." She smiled at his confused expression.
"I just have a different definition of winning."
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