BREWBOTTOM by Joe Doe A PLUCKY NEW WARDEN DECIDES TO GO UNDERCOVER AS AN INMATE, BUT SHE IS QUICKLY "EXPOSED." Natalie Brewbottom strode confidently into the exclusive club near her law offices in lower Manhattan. Although only a few years out of law school, she was already fabulously successful. She was dressed in a natty blue Armani suit with a crisp silk blouse, stylishly high heels, and a tasteful broach that the Governor of New York had given her after she had won a particularly important case back in her days at the DA's Office. Life was good for Natalie. But today there was something else on her mind. The governor of a small southern state had offered her the warden's job at a hopelessly corrupt prison for women that he was desperate to reform. It was not exactly a move up for Natalie, but money was really no longer a major factor for her. There was another aspect of the job that appealed more. She had recently seen the Robert Redford movie "Brubaker" and had become fascinated with the idea of going "undercover" in prison. It would be very dramatic; one day she would be a nameless inmate, and the next day she would be the new warden! But there was a darker side to her fantasy. She had always had fantasies of being strip searched, which were difficult to fulfill when you were a lawyer in Manhattan making six figures. But somehow she had a feeling that a beautiful young Yankee locked up in a cracker prison would have no trouble at all fulfilling THAT fantasy. Her cousin, Holly, was the governor's assistant, and she was the one who had suggested Natalie for the job. She had phoned Holly about her plan, and the latter had agreed to help if she could first talk to Natalie face to face. Accordingly, Natalie had flown her up to New York for a visit. She was glad Holly had actually showed up for the 8:00 AM breakfast at the club. Although Holly was a good friend, Natalie knew how much her cousin loved to play pranks. "This isn't like one of those stunts we used to pull back in college," Holly pointed out. "This place is corrupt and mean; if they find out who you really are, you won't be coming back." "That's why you and I have to be the only two people who know," Natalie explained in a conspiratorial whisper. "I'm telling my partners that I'm going on a sabbatical, and you will be the only one who will know where I am." "Natalie, they're not just going to take away your clothes there," Holly explained. "Those hillbillies are going to strip you of EVERYTHING...your freedom, your money, your identity. The warden and the Sheriff don't allow phone calls or mail, so you will be utterly at their not-so-tender mercies." "The prison is in the middle of a big swamp, and they use bloodhounds to track escapees. In over 100 years, no inmate has ever escaped. So, once you're on the farm, you'll be there until I release you." Holly smiled, obviously amused at the thought. For some reason, Natalie suddenly felt a cold shiver run down her spine. Was the air conditioning too high? Holly continued. "There are some rumors that the warden has some pretty unsavory parties on Friday nights," she said, impishly. "Which is why I want you to spring me Friday morning," Natalie explained. "All you have to do is arrange some paperwork to get me in." "Getting IN to that prison isn't the problem, girl," Holly said, with a laugh. "A woman like you shows up in that little town, dressed the way you are, and they'll have you touching your toes before lunch!" Natalie blushed. Holly went on to explain the plan. "Just make sure the Sheriff sees you when you get to town. He'll toss you onto the prison farm for something minor, and then the warden will find something major to pin on you when you're at the prison itself. The warden doesn't like to slap on the hard time until the girl is already wearing those prison blues and he's damn sure she can't fight back." "I won't be there long enough for that to be a problem." "Well...yeah...probably not," Holly said, waffling. "Sometimes they force inmates to work at this horrible strip club down by the highway." Holly paused. "I just thought you should know that in case...anything comes up. I mean...Friday is my definitely my TARGET date, but flexibility is the key to a good plan." Holly smiled. Natalie was too distracted by the thoughts of her upcoming search to notice her cousin's evasive tone. She was almost afraid to ask the next question. "Do you think that they'll...strip search me, Holly?" "Girl, take a look at yourself in the mirror!" Holly said, with a laugh. "Ain't one of those Bubbas that would miss a chance to strip you butt naked! "But don't worry, Natalie," Holly said, with a cryptic smile. "If a strip search is what you really want, I'll make sure you get what's coming to you...and then some!" Holly started laughing again, finding the whole situation very amusing, and Natalie tried to laugh along with her friend. But already she was feeling a growing dampness between her legs.... ************************************* Less than 3 hours later a confident, well-dressed Natalie strode into the Sheriff's office, map in hand. She explained that she was trying to get to the state capital, but she'd gotten lost and her cell phone had gone dead. She asked if the Sheriff knew of any good hotels in the area. The Sheriff rather artlessly asked Natalie about her background and whether she knew anyone in the area, or if anyone was expecting her. She explained that she was miles off course, and she doubted anyone knew where the heck she was, since she sure didn't. The Sheriff also wanted to know if that was Natalie's blue BMW rental car out front, and Natalie told him that it was. He smiled and nodded to his deputy, who quickly went outside to look at the car. "So you're sure nobody knows you're here?" the Sheriff asked as nonchalantly as possible. She was extremely unimpressed with the Sheriff's cross-examination techniques, but decided to play along. "How could they, Sheriff?" she said, innocently. This place is really in the middle of nowhere." He frowned. "Well, it's not Manhattan, young lady, but it is our home," he said caustically. "You city girls seem to think you live at the center of the universe, and we country folks are out here because we're too stupid to find the interstate." She laughed and looked around the run-down jail. "The thought had crossed my mind, Sheriff," she said, sarcastically. The Sheriff obviously didn't appreciate city-girl humor, and Natalie enjoyed watching his pig-like face getting redder and redder. Just when he was about to explode, the deputy walked in and earnestly reported that there was "a problem with the young lady's car." They walked out to the car, and the deputy pointed out that it didn't have a license plate sticker. "Well, the currency exchange up the interstate is closed today, and we certainly can't let you drive around in a car with no sticker. If you go back in and sign the citation, I'll make arrangements so that you can have some accommodations for tonight." Pieces of her sticker were still visible underneath the idiot deputy's fingernails, and Natalie could see the rest of it stuck to the top of his shoe. Fighting the urge to laugh, she dutifully went inside to sign her "confession." She wondered how in the world the Sheriff was going to inflate this relatively minor violation into a stay on a hellhole prison farm for women. It wasn't until the Sheriff's squad car pulled through the front gate of the "Honey Pot Prison for Women" that she realized what the his idea of "accommodations" was. She protested that she thought she was being taken to her hotel until the currency exchange opened in the morning. "If you wanted us to do that, you should have paid your $10 fine back at the office. It clearly states on the back of page 3 of your citation that, if the prisoner doesn't notify the arresting officer of intent to pay the fine, then the alternative prison sentence takes effect. The Sheriff smiled. "You've just sentenced yourself to 180 days at the prison farm, sweet cheeks!" Natalie quickly pulled out her wallet and tried to pay him, but he took her money and purse away, explaining that "inmates aren't allowed to carry contraband." He then introduced her to a very butch-looking prison matron, and they all marched into the administration building at the front of the prison. The first floor of the admin building was a large office area with about a dozen prison employees of various genders sitting at desks, processing paperwork. The matron marched Natalie to the back of the area and selected a cardboard box. It was an old box for JASPER'S CORN FRITTERS, but someone had written her name and prisoner number on the side with a black magic marker: BREWBOTTOM, NATALIE 555-58-03483-A "OK, honey buns, it's show time!" the butch matron said, harshly. "Shuck off all them fancy duds and drop them in the box. I want you wearing nothing but your pretty little smile in two minutes." Natalie looked around her in disbelief. There were at least a dozen prison employees, most dressed in civilian clothes, who could see her perfectly. A few guys had even come out of the mailroom to enjoy "show time." Another group of office workers had emerged from the lunchroom, sandwiches in hand. But, what was worse, the grinning Sheriff and his toady deputy were standing just a few feet away, with their arms folded, obviously enjoying Natalie's predicament. "HERE?" Natalie said in disbelief. "In front of EVERYONE?" She had wanted to be strip searched, but she hadn't imagined that it would be in front of twenty of the local yokels. "No need to be modest, sugar," the matron said, acidly. "Of course, if you want some of the guys here to give you a little bit of a hand with your striptease, I'm sure they'd be more than happy to oblige...." Natalie didn't need to be told twice. She quickly took off her expensive shoes and put them in the cheap recycled box. Next came the Armani jacket and fashionably short skirt. Then she surrendered her diamond earrings, pearl necklace, broach, and expensive watch. Next was her silk blouse, which left her in garter belt, stockings, and bra and panty set. "GOL-LY!" the slow-witted deputy exclaimed. "I feel just like I'm watching one of them Victoria's Secret fashion shows on the TV!" "Yeah, except on TV, this is the point where they cut away for a commercial," the Sheriff said. "But we actually get to see the little Yankee's KNOCKERS!" "You heard the fellas, babe," the matron said with a sneer. "This here is a CAVITY search, which means we need to strip you from top to toe! Don't start acting all uppity just because we finally got to the good part. Drop those fine, white frillies into the box, girl!" Soon Natalie was standing there with her hands on top of her head, turning slowly in a circle while the rubes "appraised the merchandise," as the Sheriff called it. "What a little slut!" "That sure looks like one sweet piece of ass." "I hear college girls make a lot noise when you pork 'em." "That pussy fur is so soft and downy...I bet you could make a pillow out of it!" "Look at them sweet lips. I say she's a natural born cock sucker!" "Forget THOSE lips! Look at her sweet PUSSY lips!" "I can't hardly wait to see the cavity search!" "Oh-oh, it looks like the poor little doe is blushing!" "You ain't gonna cry on us, are you, sweet pea?" "She won't look so high and mighty when they lay some strap oil on that sassy tight bottom!" And so on. Natalie flinched at the reference to strap oil. Holly had warned her that they used corporal punishment, but Natalie had thought she was joking. After all, Natalie was an educated, sensible young woman, not some misbehaving teenager who needed a trip to the woodshed to keep her in line. She had assumed that her strip search would be just that, and she hadn't anticipated a cavity search. What made it worse was that her probing was obviously going to be done by a lesbo guard in front of a staff of hillbilly paper-pushers. While Natalie was dancing around in circles, the burly matron put on a "pinky cheater," essentially a one-finger condom. While Natalie continued to turn round and round, the matron playfully held up her finger and lovingly greased it. Appropriately enough, she was holding her hand up in the classic "fuck you" gesture as she did this, which left little doubt about where the greasy digit was going. The matron told Natalie to stop turning. "Face front! "Spread your legs! "Now squat 10 times and cough! "No, SQUAT, till your butt almost hits the floor! "That's right! And keep those juicy white thighs spread nice and wide when you do it." Natalie complied with each humiliating command, giving the office workers quite an eyeful. "Now turn left!" Natalie turned again. Now it was the lunchroom's turn for the gynecological show. "Do 10 more squats!" And so on, until everyone in the room had seen Natalie's twat and spread buttocks, front and back. Next the matron made Natalie put her leg up on a chair, for her cavity search. Under the guise of getting a better look, she had Natalie change positions several times during the search, making it a "theatre in the round" performance. Despite her embarrassment, Natalie's pussy was hot and wet, a fact that wasn't lost on the matron, who helpfully pointed it out to the crowd. Naturally, this led to another round of catcalls, which embarrassed Natalie still further...and made her even more excited. The matron also performed the rectal search from a variety of angles. Four times Natalie had to bend over and put her hands flat on the floor with her knees spread while the matron probed her thoroughly. Throughout the ordeal, comments from the on-lookers burned in her ears: "She's sure a wet little floozy. What she needs is a good butt-reaming." "That's what all those fancy college girls need." "It would be fun to fuck a lawyer up the ass once, instead of the other way around." "Man, a trip up that cute little Hershey Highway." "Yeah, fancy college girl, she looks like she could really use a good fudge-packing." At last the seemingly endless search did in fact end, and, with a quick slap on the bottom, Natalie was ordered into the next room. She looked sadly behind her at the cheap cardboard box containing her ID, her money, her clothing, and her dignity. Natalie wasn't too happy when the Sheriff, his deputy, and a group of her lunchroom buddies followed her into the next room to watch her take her shower. The concrete shower area was large, and it was easy for everyone in her audience to make sure they got a good view as she lathered herself up. The grinning matron gave the blushing girl pointed directions, in order to make sure that she didn't "miss a spot." Natalie noticed that the smell of the stinking soap quickly overpowered her expensive perfume. It was only when she looked at the label on the soap container in the shower that she realized why the odor was so pungent and why the liquid was burning her tender skin.... It was delousing soap! She knew now what a dog felt like when it was put through flea dip. But it got worse. As soon as the shower was over, the matron put on an old gas mask (that might have been left over from World War I) and ushered Natalie over to a large green hose that was hanging out of the wall. Natalie knew that this wouldn't be good, because her attentive male audience quickly excused themselves, a few promising to "see you later." Like there was any more of her to see! The matron told Natalie to spread her arms and legs so that she was a human X while the matron pointed the menacing hose at her. The fluid that came out of the shiny nozzle stank like fury, and Natalie was soon coughing and wheezing. It was bad enough to delouse her, but did they have to do it with fluids that smelled like they were just pumped out of the septic tank? At last the matron finished, and the sputtering Natalie was given a towel. The matron left, and Natalie quickly dried herself and wrapped her naked body in the scanty towel. Then she waited. And waited. And then she waited some more. After about an hour, the matron returned, accompanied by the warden, a tubby man in a white suit and hat that reminded her of Boss Hog on the old "Dukes of Hazard" TV show. Since the deputy was a cross between Barney Fife and Roscoe P. Coltrane, it was obvious that they got Nick-at-Nite in this part of the country, Natalie thought, bitterly. "Here she is, sir. This one was wet as a pistol when we searched her, despite her fancy college degree and those big city airs," the matron said. "She may be a Yankee, but she's got a hot, spicy, Cajun cunt!" Natalie blushed as the piggy warden looked her up and down, starting his examination at her long bare legs, and working his eyes up her body to her silky brown hair. Natalie swallowed hard. Her cheap green towel wasn't much, but she was glad that she had it to cover her nakedness. Obviously the warden wasn't. He nodded to the matron, who immediately barked at Natalie, "Open up your towel!" Natalie stared at her in disbelief. She had to be joking. She couldn't just open up her towel...in front of HIM! She had been naked in front of more than a dozen people today, but the casual way that the warden had walked in to strip away her last bit of dignity and crush it beneath his feet was just too much to bear. Somehow, asking her to open up her towel like she was a piece of meat there for his inspection was infinitely worse than being made to shower in front of the lunchroom morons. Natalie was snapped out of the reverie by the matron's impatient voice. "I said, 'Open up your towel!' NOW!" What choice did she have? Slowly, reluctantly, Natalie complied, exposing her nakedness to the warden's gaze. He didn't say anything, but Natalie could see his gold tooth when he smiled at her. Once again his eyes ran down her naked form. His lust was unmistakable, but his demeanor and white suit were preposterous. "Why do these guys always dress like they're the Governor of Devil's Island?" Natalie thought. The warden reached out and slowly ran his finger down Natalie's tummy and over the soft furry patch between her legs. He smiled as his finger wormed its way between her thighs and felt her wetness. He gave the matron a simple command, "Saturday, 6:00 PM." Then he walked out of the room. Natalie swallowed hard as she remembered Holly's warnings about the "unsavory parties" that the warden held on weekends. ************************************* Within 15 minutes of the warden's welcome departure, a very sweaty Natalie found herself working on a chain gang on the outskirts of town. Except for the chains around her ankles, they had dressed her like a cheap imitation of a "Hooters" girl: white sneakers and white socks, tight orange short-shorts, and a midriff-baring crop-top t-shirt (with no bra). Other girls were swinging pick axes to bust up the lane under repair. Natalie's job was to haul the heavy pieces of broken asphalt back to the dump truck, which was conveniently parked a mere 30 yards from where the roadway was torn up. Natalie thought of suggesting that they move the truck closer to the debris, but she decided that the guards weren't really interested in efficient work techniques. Earlier that morning one of the other prisoners had volunteered to call her father, explaining that he owned a machine that could "tear up this whole road in about 10 minutes." The guard quickly bent her over, pulled down her shorts and underwear, and then delivered a painful and humiliating strapping right by the side of the road, much to the amusement of passing motorists. "Maybe they wanted her to use the Suggestion Box instead," Natalie thought, bitterly. The gawking hecklers were the worst part. Natalie's t-shirt was soon soaked with perspiration, which provided an amusing wet t-shirt contest for local hicks who drove by or parked their cars by the side of the road to taunt the helpless women: "Bend your knees, sweetie!" "I hope y'all are learning your lesson!" "Would you like some water? Well, that's too bad, because yo're not gonna get any!" "How'd you like to get yerself some of that hot jailbird pussy?" "I bet you they're insatiable, with no real men to satisfy 'em!" "No, the little lesbos just lick each other all night!" "Look at the titties on that little brunette! Her nipples look like thimbles!" "Isn't she that fancy college girl we saw at the gas station, in her hot little sports car?" "Well, she sure don't look so snooty now!" That was certainly true. A few hours ago, Natalie had been a self-confident career woman, dressed in the height of fashion. Now her soft, expensive silk clothing, designed to flatter her, had been replaced by cheap cotton scanties designed to humiliate her. A few hours ago she had been ordering these Goobers around at the gas station, warning them to "be careful with the car." Now they were gawking at her protruding nipples and mocking her with their humiliating commentary on her ordeal. She hadn't realized that she could fall so far, so fast. She had flown down early Monday, expecting that it might take a few days to get picked up, and a few days for her trial. Holly had warned her that "Southern slowness" didn't apply to the processing of pretty young female inmates, but Natalie had ignored her and based her schedule on her experiences with "due process" in New York. The net result was that Natalie had thought she would be put in prison on Wednesday or Thursday, and Holly would release her on Friday morning. But now she was hauling rocks, and it wasn't even lunchtime on Monday! It had taken only a few hours to transform her from a successful young attorney into just another "babe behind bars" in a bad prison movie. They had taken away her old self, and she was now doing manual labor under the threat of the prison strap. She grunted as she moved the heavy rocks under the taunts of the rednecks. It was like the powerful woman she had been had disappeared, replaced by a helpless bimbo who existed only for hard labor and sexual humiliation. She tried not to let herself cry, knowing how much her tormenters would enjoy breaking her. (Besides, she would need all the salt and water she could get.) The next five days were a backbreaking nightmare of humiliation, hard labor, and helplessness. They worked her hard out on the road, and all of the inmates were strip searched and showered by leering guards after every "road trip." The food consisted of mush she wouldn't feed to a stray dog. At least she didn't have to worry about lesbian sexual assault; the inmates were too exhausted at the end of each day to do anything but collapse into the cheap steel bunks in the large dormitory. Friday couldn't come soon enough, as far as Natalie was concerned. At last Friday morning came...and went. And there was no word from Holly! On Friday afternoon, Natalie was excused from her work on the chain gang so that she could rest for the "party" that evening. She dreaded the thought of going to the warden's disgusting party, but took advantage of the time to sleep, sleep, sleep. Promptly at 6:00, the proud lawyer found herself dressed in an extremely short black cocktail dress, making conversation with the local tycoons who helped the warden run his illegal schemes. She met with the contractor who was happily charging the taxpayers a fortune for the road she was building. She met with the "caterer" who provided the inmates with their savory collations, pocketing the difference between the cost of real food and the cost of the slop she was actually given. She met the sleazy manager of the local strip club, who promised her a large crowd of farmers and truckers waving dollar bills at her debut Saturday night. Natalie flinched at the thought. Surely Holly would rescue her before THAT! She met a local farmer who "complimented" her by telling her that it was cheaper to use female prisoners to pick cotton on his farm than it was to use slaves back in the 1850s. "Plus, you gals are way more fun to look at!" Natalie tried to look happy at the news, but, not being a particularly good actress, she failed miserably. She even met Jasper, whose corn fritters box now held her money, ID, and clothes. Natalie had wanted to meet with these people in her efforts to ferret out corruption at the prison. But here the term "meet" was actually a euphemism. By the end of the evening, she had given a blowjob to almost every man in the room. On the brighter side, she knew that she would remember all of their names. It was pretty hard to forget a guy once you'd had his disgusting, spurting ding dong in your mouth. She was sure that her cousin would spring her Saturday morning. Holly wouldn't let them force her to strip and dance BUCK NAKED at some sleazy club. But dance she did, to the delight of the cheering, whistling, stamping crowd! When another 3 days on the road gang passed with no word from Holly, she became desperate. Her chance came when she was ordered to go into the warden's office and polish the shoes of the 18-year-old blonde harpy who worked as the warden's secretary. She remembered the secretary from her first strip search. Natalie was much prettier than the chunky girl, who had remarked that she was going to enjoy seeing "that stuck-up college girl taught a lesson." The secretary relished her power over Natalie and was soon bossing her all around the office doing menial tasks. As soon as the secretary left the room to get herself yet another candy bar, Natalie vaulted over the desk to get to the phone. After 8 rings, there was finally a pickup. "Hello, this is Holly Smith's office," the bored secretary on the other end of the phone said. "I am an old friend of Holly's, and this is an emergency, and I need to speak with Holly RIGHT AWAY!" The words tumbled over one another as Natalie whispered in a breathless panic. She knew she didn't have much time to waste with chatter. "Miss Smith is on a four-week vacation in Hawaii and can be reached only in case of emergency," the secretary replied, going through her standard speech. "I already SAID that this IS an emergency!" Natalie whispered, desperately. "I need to talk to Holly, or ANYONE in charge, right NOW!" "One moment, please," the secretary said, mechanically. "I will put you on hold and see if someone is available." "No, don't put me on hold, listen to me!" Natalie cried, breathlessly. "My name is Natalie, and I...." It was too late. The secretary had already cut her off, and the music had started playing. Appropriately enough it was a muzak version of the old Eric Clapton song "I Shot the Sheriff." Natalie loved government bureaucracies! She couldn't believe she was ON-HOLD! She couldn't believe that her cousin had gone on VACATION without releasing her! Holly had played some mean tricks on her before, but this was the worst. While Holly was tanning on the beach, guzzling drinks with little umbrellas in them, Natalie was being worked like a horse and strip searched EVERY DAY. Then Natalie had an awful thought. "I hope Holly remembers me when she gets back," she thought, grimly. Eric Clapton's famed accordion work was interrupted when the chunky secretary snatched the phone away from Natalie and slammed it down on the receiver. "NO PHONE CALLS!" she shouted. The malicious girl had Natalie right where she wanted her, and they both knew it. "Please, miss," Natalie pleaded in her most pathetic voice. "Please don't tell anyone...." The girl looked Natalie up and down with an angry stare. Even in that stupid Hooters outfit, Natalie was still cuter than her! The tubby girl smiled and picked up the phone to dial the matron, singing playfully, "Nat-a-lie's getting a SPANK-ING! Na-ta-lie's getting a SPANK-ING!" Natalie involuntarily reached back to rub her bottom cheeks as the girl continued taunting her with that humiliating song. Natalie felt her throat go dry as she remembered that all strappings were given on the bare bottom. Natalie was still undercover, but she knew that, once again, she would soon be exposed. She knew that, somewhere, Holly was smiling. ************************************* SINCE NATALIE WAS KIND ENOUGH TO SAY THAT SHE ENJOYED MY "HOT AND FUN" STORIES, AND THAT SHE IMAGINED HERSELF AS THE HEROINE, I DECIDED TO GRADUATE HER FROM COLLEGE AND GIVE HER A STARRING ROLE. THIS STORY WAS PARTIALLY WRITTEN TO SATISFY THE NERDLY'S REQUEST FOR ONE WITH PROSTITUTION, AND MORE BLOWJOBS, CHAIN GANG WORK, AND CORPORAL PUNISHMENT. I HOPE BOTH NATALIE AND NERDLY LIKE IT, AND I HOPE OTHERS SEND IN FEEDBACK LIKE THOSE TWO DID SO THAT I CAN USE THEIR IDEAS IN MY STORIES. THANKS TO ALL! Edited by C. Lakewood