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  1. #1

    To Tame a Cougar Pt. 1

    To Tame a Cougar
    Alternative title: Jennifer's Blackmail

    Warning! This story is ideologically sensitive and may trigger or offend. Just a polite FYI.

    “Please remember that these issues do effect you and your families, so please take the time to vote on November 6th, and have a safe weekend,” said Jennifer to close her site meeting. Her audience of around ten people then left the room to either go home or back to their offices. Jennifer was in charge of political outreach for a public sector union for municipal employees. She would often schedule times to visit worksites, usually during lunch, and talk to union members and others about state elections and why they needed to vote for the union-endorsed candidates.

    Jennifer believed wholeheartedly in her cause and would often volunteer in her spare time to knock on doors for local Democratic candidates. She was a smart woman, she possessed a master’s degree and had years of experience in political and union organizing. She was a tall, fit woman in her late thirties, probably 37 or 38, and she had the most beautiful, long, luscious legs. Her thighs were just a little plump, as was her butt, just enough to drive all the younger men crazy. She was a brunette with a silky head of hair and an infectious smile. She was drop dead gorgeous and aged like fine wine. Make no mistake about it, she wasn’t some “baby girl,” she was a real woman. She had no kids, not even a husband. She said she wanted those things, but somehow never acquired them.

    As she was putting away her papers and other materials and planning on leaving, a strange man entered the room. He dressed in black and white business casual attire. He was clean shaven and of modest height. He approached her with an air of arrogance that only a man in his mid-twenties could have. Jennifer looked up and greeted him, thinking he wanted to ask her questions about the state election or something. Nope. He produced a small gun from his pocket.

    “Don’t scream, just do what I say and you’ll leave here alive,” he said.

    “OK fine, please don’t hurt me, I can give you,” Jennifer said before being interrupted.

    “Shut up, I don’t want your stuff,” he said. “Now walk in front of me, go this way.”

    The man led her to the basement of the building. It was a modest office building for county workers who handled billing and taxes and other boring stuff, so its basement wasn’t exactly impressive or intimidating. The man locked the entrance behind them and flipped on the lights, drawing Jennifer’s attention to the middle of the room. She noticed a chair that looked like it was designed to strap someone down spread eagle, except it was a chair. It had a place to strap her arms above her head and individual legs for strapping down her feet.

    “Take your clothes off,” he ordered.

    “Please, please don’t,” she begged, trembling.

    “Take them off or I take them off for you,” he said firmly but calmly.

    Jennifer gave him a look of shock, then she slowly removed her light red dress. Then she removed her flats, her panties, and her bra. She was now naked and being held prisoner by a strange man. Although she was older, she was still fit and her body was gorgeous. She was definitely a cougar, a MILF without kids, a real head-turner.

    “Now get in the chair,” he said, waving his gun around.

    She reluctantly complied and got in the chair. She wasn’t comfortable spreading her legs apart, but did so anyway out of fear that it would get worse. He then strapped her in tight, securing her wrists, ankles, and legs. Jennifer’s body was entirely his now to do what he pleased with.

    “Who are you?” she asked as the man put his gun away.

    “My name is Ed, and I have pretty much the same job as you except I work directly for the local GOP,” he answered. Sweat could be seen breaking across Jennifer’s brow. “I know for a fact that you have access to the financial information of the union and the local Democratic Party, and I need those numbers.”

    “Please, this is so illegal, and it won’t end well for you-HAHAHA!” she said as Ed began tickling her feet.

    Her slender toes would wiggle around and scrunch up as he prodded every sensitive spot on her soles, heels, and the balls of her feet. She took good care of her feet, and Ed really appreciated how she painted her toenails with a glittery, purple nail polish. He hated how women his own age never bothered to paint their nails, wear dresses, or act like women. He was so enamored by the squirming of her pretty feet that he almost forgot it was an interrogation. Ed wasn’t immune to the charms of “slightly” older women, but he regretfully had to shake off his amusement for the moment.

    “Come on, tell me,” he said, snapping out of it.

    “No, think about what you’re doing,” Jennifer pleaded. “Oh shi-ha-ha-ha-t,” she giggled as he clenched her precious toes and gently dug his nails along the bottoms of them. “No, no, no,” she said, shaking her head from side to side, but it didn’t help her endure the tickling. Ed than gave the top of her foot a firm squeeze, forcing her toes apart, and produced a pipe cleaner from his pocket.

    “Nobody has to know you gave it to me,” he said, wedging the fuzzy pipe cleaner between her toes.

    “AHAHA, no please st-ah-ha-hap,” Jennifer begged as he flossed the toes on her left foot, and then on her right foot. He would pull the cleaner slowly out from between each toe, making sure she would feel every bristle against her skin. She would try to wiggle her feet out of his hands, but he was too strong. After about ten minutes of the flossing, he decided to take it up a notch.

    “Mmm, nom nom nom” Ed blurted out tauntingly as he began to suck each one of her toes individually, flicking his tongue all over them.

    “EEWWW HAHAHA” she squealed nervously. He then began to gently nibble on the sides of her feet and toes, driving her crazy. Jennifer laughed harder, but her laughter was more pained because she knew this wasn’t just tickling and he wasn’t playing around by doing that. Without speaking, he was sending her a message that he could easily hurt her. At any second his teeth could sink into her toes and possibly injure her. Just knowing this was a possibility terrified her.

    “You’ll have to tell me eventually,” he said.

    “I don’t even know that stuff, you’re crazy,” Jennifer insisted.

    At this point, Ed figured she might be more sensitive elsewhere, so he turned his attention to her ribs. He began to firmly trace each of her rib bones with his fingers, causing her to squeal and squirm to avoid him, but he was too fast and she was secured too tightly.

    “Oh god, ple-he-he-ase,” she laughed as Ed began to gently poke each of her ribs.

    “Let’s make this worse for you,” he said, pulling a pen out of his pocket. He then grabbed one of her tits and gave it a good, strong squeeze.

    “Ow, fuck!” exclaimed Jennifer.

    “OK, so I’m going to write all over your ribs, and if you mess up my writing by squirming around I’m going to squeeze this boob until it pops, got that?”

    “Fine,” she said, trying to avoid getting hurt. Ed kept his hand on her vulnerable breast as he began to write. Each ticklish stroke of the pen made her skin crawl. She wanted to move away, but knew he’d hurt her if she did. Her agony only intensified when she realized he was writing the name Trump over and over again on all of her ribs. Her face turned red with humiliation.

    “Let’s see, I don’t think the T is clear enough here,” said the captor, retracing his lettering as he increased his grip on her breast. It tickled so bad that she wanted to twitch involuntarily, but she had to hold it back or else her boobs would be in a world of pain. Her ribs were extremely ticklish and each stroke of the pen was very disorienting for her. She tried so hard to keep herself from twitching, but it slowly built up with each tedious, ticklish stroke of the pen against her ribs.

    “I’m so sorry, please don’t hurt me,” Jennifer begged. Her reaction to squirm had finally built to a breaking point and she twitched and shook involuntarily, messing up her torturer’s writing.

    To Jennifer’s surprise, he let go of her boob, threw his pen on the ground, and jus t looked at her. Ed breathed a depressing sigh, but Jennifer’s heart was racing, fearing what might happen. She looked at him with her frightened expression and her girlish eyes, her fear and weakness showing in them. He then began to gently run his fingers through her hair while he tried to fight back a smile.

    Ed was just a young man who was tired, lonely, and hungry. He had a lonely life at home, and he had left it to come work for his party in a strange city. He had spent most of his time alone, he had no friends growing up, and he spent most of his life being abused. He was ready to have a wife and kids, but the women his own age were so cold and rejected him.

    “I bet she cooks really well, and I bet she gives the best hugs,” he thought to himself as he enjoyed the feeling of her hair between his fingers. He began to think she could fill the voids in his life and give him the love and affection he so desperately wanted. He imagined coming home to her every night and eating a home-cooked Midwestern meal that she made for him. He imagined her polished nails finding that sweet spot on his back every night. He imagined being loved by a woman for once instead of them calling him a “misogynist” and a “racist” and all the other crazy things young women have been indoctrinated to say.

    “Uh, um,” said a confused Jennifer trying to find some kind of words or idea to communicate to him. It was so weird, yet frightening at the same time. Ed met her eyes and slowly snapped out of it. He removed his hand from her hair.

    “Don’t make me hurt you, I don’t want to hurt you,” he said, walking out of her sight to fetch something.

    “Look, there’s another girl whose name is also Jennifer, and she’s your age, and she’s really pretty,” she said to him. “She has all the information AND a cute laugh,” she continued her bargaining. “I’ll tell you where she is and you can tickle-rape her instead,” Jennifer pleaded.

    “That isn’t going to work, I know it’s you we want,” he said as he reentered her sight. “Now hold still or there will be trouble,” he said as he pulled a long stretch of duct tape.

    Jennifer gasped as he taped down a Hitachi vibrator to her midsection, with the head of the vibrator making good contact with the top of her pussy. She was too stunned to be scared. Just the thought of a stranger trying to force her to orgasm. That stun soon returned to fear as he produced to clothes pins from his pocket and slowly approached her chest.

    “No, please, you have the wrong girl,” she begged. It was futile, the pins clamped down on each of her nipples. “AAHHH!” she let out, shaking her head in pain. She began to breathe heavily, then she winced as the vibrator was turned to its highest setting. “I will never cum for you,” she said after a soft roar.

    Ed silently left her sight again, causing her anxiety to grow. “I couldn’t care less if you cum,” he said as he reproached her holding a candle. “I just need some campaign plans and some bank information,” he said, lighting his candle.

    Jennifer tried to ignore him as she squirmed in her torture chair. She had these pleasurable sensations all over her body, especially her pussy, but every time they wanted to grow and build up, they were knocked back by the sharp pain on her nipples. All she could do was moan and grow red in the face. She didn’t know if she wanted to cum, to resist the urge to try and cum, or scream from the clothes pins biting her tits. This conundrum had distracted her so much that she didn’t realize the candle was starting to drip hot wax and Ed had it right over her toes.

    “OW, FUCKING SHIT!” she cried out as the hot candle wax dripped between her unsuspecting toes. The wax would give her a sharp, piercing burn, but would fade away quickly without any injury. “Ow, oh, oh, ow you’re a monster,” she whined as he dripped a line of scorching wax across the top of her foot, stinging her like a giant bee.

    “Come on Jenny, it only gets worse after this,” Ed told her as he pulled her big toe to the side and dripped a big glob of hot wax between it and her second toe. He smirked as he looked up and saw her pussy was crazy wet.

    “ERR, AHH,” she groaned as the sensations began to build in her pussy. She was inclined to focus in on them, but she knew she couldn’t cum in front of him, especially because he was likely to keep that vibrator on after the orgasm, giving her a tickling from hell.

    Jennifer had never had someone else manipulate her body like this before. She didn’t know what to think, all she knew was that she hated it, but somehow in the moment it hurt so good. The sensations in her clitoris began to build and she was at the breaking point, but she was held back by the pinching, the burning, and the anxiety. She wanted to cum, and she wanted to go home.

    “OK, OK, look, the bank numbers, I’ll tell you, just stop hurting me,” she begged.

    “Alright, I’ll give you permission to tell me, but first you have to do something for me,” he said.

    “What?” she said exasperated, fighting back tears. She couldn’t wait anymore.

    “Tell me you love this, and that you love Russia and the Donald,” he said.

    “I love,” she said, pausing to gulp, “BDSM,” she finished.

    “And what else?” Ed asked tauntingly.

    “I love President Putin and President Trump,” she said as a sick feeling pierced her stomach.

    “Can I grab you by the pussy sometime?” he asked mockingly.

    “Ouch, ouch, yes, whatever you want, just stop hurting me,” Jennifer said.

    Ed dripped one more bit of wax on her foot before blowing out his candle and removing the clothes pins from her boobs. He then pressed the vibrator more firmly against her vagina so she could really feel it. All of that restrained, repressed sexual tension burst like a volcano causing Jennifer to squirt her juices all over the place.

    “OH, OH, OH, OH, GGGOOOODDD!” she exclaimed as the orgasm rocked her. “OH GOD!” she exclaimed again as it began to tickle. It was the worst tickling ever. She tried to squirm, but it was no use. It was disorienting, it was intense, and it consumed every centimeter of her vagina.

    “Now, tell me that stuff you promised,” Ed demanded. “Because I can tickle your pussy all night.”

    She talked. She betrayed her party, her union, her friends, and her conscience just to stop the torture.

    Jennifer closed her eyes for a minute as he switched off the vibrator. Her orgasm had been ruined. She felt sick, exhausted, humiliated, but worst of all she felt like she had lost any shred of dignity.

    “Now,” he said, “You’re going to come visit me every week and give me updates.”

    “No, no I’m going right to the police,” she said, exasperated.

    “No you won’t,” Ed laughed. “I have this whole thing on video,” he said pointing to a hidden camera. “I can edit the footage to look like you loved this. I’ll put it on every website out there,” he threatened. “PornHub, xHamster, YouTube, Clips4Sale, the Tickling Media Forum, all of them. Your career will be over and you won’t ever get hired above minimum wage again, you’ll be just some slut from the internet.”

    “OK, please don’t do that. You win.”

    “Good, and you’ll also keep me company when you’re done updating me on your side’s happenings and finances,” he continued. “You’re going to let me do whatever I want to you from now on. When I call you, you come running. If I want to tickle torture you every week, it’s going to happen. If I want to fuck you in the ass, it’s happening. I own you.”

    Jennifer began to cry a little, but she was out of tears, the torture was too much. “OK Ed, you’re my boss now,” she said in a defeated tone.

    “Get your nails done, wear some revealing shoes, and a revealing dress too,” he ordered. “Don’t ever come visit me in pants, you’re a woman,” he went on. “As a matter of fact, you’re my woman now. Do you have a boyfriend or husband?”

    “No, not for a long time.”

    “Good, think of me as your secret boyfriend now,” he said. He then bent down and picked her purse up off the floor. Jennifer watched as he pulled her wallet out of her purse. “I’m going to reward myself tonight with a nice steak dinner,” he said, pulling out Jennifer’s credit card. “I have a reservation at the Russian restaurant.”

    After Ed collected his things, he untied his prisoner. She gingerly got up and put her clothes back on. As she walked down the hall out of the building, she felt like everyone knew she had just been sexually dominated in the basement. She felt humiliated as the workers looked at her with inquiring eyes. It’s almost as if they knew what happened. They could tell something happened to her, but they weren’t sure what.

    Jennifer walked slowly back to her car. Her feet hurt, her pussy hurt, her tits were throbbing, and she couldn’t feel her face. She sat down in the driver’s seat and held her head in her hands for a few minutes. Her life was over.

    Will Jennifer’s colleagues discover that she gave out classified information? Will Ed’s blackmail video destroy her career? How will Ed treat his new, sexy cougar now that he has tamed her? Find out in part two!
    Last edited by Angra Mainyu; 09-09-2018 at 10:21 PM.

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