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A Prisoner's Tail	By : FairySlayer Category: +S through Z > Simpsons Views: 20401 -:- Recommendations : 0 -:- Currently Reading : 0
Disclaimer: I do not own "The Simpsons" or have any association whatsoever with it or Fox; I do not make any money for writing this story.

Chapter List
- 1-A Prisoner's Tail
- 1
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“But it didn’t go so well the last time,” Lisa squeamishly told her mother. “It wasn’t a good fit, and it really hurt me a lot. And I think Bart also had some pain associated with that incident.” Sitting sideways on the couch, she nervously drew her outside foot back and forth across the carpet while looking down, avoiding her mother’s gaze.

“Oh, sweetie, you were just a little uptight, and you tried to take control of every little detail,” Marge assured her. “Sure, maybe your father and I shouldn’t have put you in that position at such a young age, but I’m positive that you and your brother could get through it now.”

“I don’t know,” Lisa said with more than a little hesitation. “Bart just goes so wild sometimes...”

Marge leaned forward on the couch. “Lisa, your father and I don’t like forcing you to do it, but we’re desperate. We’re even willing to pay you $20.”

“Fine,” Lisa said unenthusiastically. It wasn’t that she wanted the money so much, but she knew her mother must really need her badly to pay double her normal rate.

“Oh, thank you, Lisa!” Marge leaned in and, with both hands on the little girl’s shoulders, kissed her on the forehead. Then she jumped off the couch and started rattling off various thoughts as she headed for the kitchen. “I’ll call them back now and put the phone numbers on the ‘fridge. There’s plenty of formula and a new bag of diapers, and you can order pizza. Besides, Mr. Flanders is just next door if you have an emergency.”

She stopped at looked back at Lisa, who was still fidgeting nervously. “And Lisa? Don’t worry too much about Bart. If you leave him alone he’s not likely to try any funny business. But just make sure he doesn’t burn down the house or anything.”

“I understand,” the little blonde said while picking herself up off the couch. Marge simply went back to preparing for her evening out with Homer.

Lisa headed up to her room, telling herself she’d take a nap to be ready for her brother’s hijinks, but she knew deep down that she would just lie on her bed and worry. Her heart sank as Bart walked by her in the hallway, but she decided to get it over with. Why should she be the only one dreading the evening, especially since it was all his fault anyway? Besides, he might tire himself out whining to Mom and Dad about it.

Suddenly, inspiration struck and her heart began beating faster. “Oh, Bart,” she said while trying to sound calm. “Mom just told me that they’re going out tonight, so I’ll be babysitting Maggie and we can order pizza.”

“Cool,” he said in passing, not even stopping to acknowledge her information. Lisa stood still, feeling more relieved with each of his footsteps, but she heard him stop a few steps later.

Slowly, Lisa turned around to find Bart glaring at her.

“Wait a minute. Who’s babysitting me then?” he demanded.

“Uh, Mom and Dad feel that you’re responsible enough to behave, and I’ll be here to keep an eye on you in case, uh,” she stumbled. “If anything happens to either one of us, the other will be here...”

Bart stared at her with more disappointment than disbelief. “You expect me to laugh at that lame joke?”

“Okay!” Lisa admitted, “They want me in charge, but you can pick the toppings and I won’t tell you what to do. Just don’t get me in trouble and you can have half my fee.”

“Hmmm, I was just going to threaten to hurt myself and blame you all night, but okay,” he said with a grin before disappearing into his room. “Make the pizza ultra-super-meat deluxe,” he called out as an afterthought.

Lisa laughed to herself for a moment, as she hadn’t told him about the double pay, but then she realized she wouldn’t hold back because, even if he didn’t find out, she’d just have something different to feel bad about. She thought to herself, “Maybe nothing bad will happen tonight. Or at least nothing too terrible.”

Lisa kept her cool. When Bart left messy dishes in the living room, she quietly picked them up; when he switched the channel to a horror movie, she just took Maggie upstairs and played with her until it was time to put her to sleep. She was convinced he’d do something to freak her out, but she secretly wished that he’d just try to make her worry about it all night and then forget to actually pull any stunts.

After tucking Maggie in and putting her to sleep with a bedtime story about Platonic solids, Lisa decided to call it a night herself. She went into the hallway and walked towards the bathroom, but she heard sounds coming from Bart’s room yet also heard the television still on downstairs. So, she took a detour to the living room and, seeing that Bart wasn’t there, shut the TV off. Then she washed the dishes and made sure everything was neatened up before returning upstairs.

As she got to the top of the stairs, she realized that she really had to go to the bathroom now. Without paying attention, she hurried towards the bathroom when she was suddenly grabbed from behind. “Baaaart!” she cried out, more angry than scared as she was pulled backwards. “Cut it out! I really need to pee!” she protested while struggling against the arms around her.

The only answer she got was to be lifted off the ground and carried backwards. Then she noticed that she was up pretty high. “Bart?” she half-whined as fear began to set in. “Did you invite someone over to scare me?” she asked timidly before finally squeaking out, “’cause it’s working.”

She was pulled into Bart’s room, which was dark except for the hall light shining through the doorway. Her captor turned her to face the bed and she gasped in horror: Bart was lying on his side, gagged and bound with his hands behind his back. He looked up at her with intensely fearful eyes. Before she could say anything else, her assailant pressed her face-down on the bed and grabbed her arms. She was too frightened to resist as her hands were tied together behind her back and then her ankles tied together.

Bart tried to speak, mumbling excitedly through his gag, but Lisa couldn’t understand any of it. She turned to face him as he suddenly fought to free himself, but a large hand forcefully whacked him on the side of his head. He inhaled with a slight squeal and stopped fighting his bonds. Tears formed in his eyes as he watched his little sister being subdued.

“Please don’t hurt us! I’ll do whatever you say!” Lisa begged, but there was no answer. “Take whatever you want. We don’t have much, but it’s all yours. I don’t know what you look like and Bart’ll promise not to tell.” There was no answer other than for the intruder to test the bonds on her hands and feet. Bart closed his eyes and slowly shook his head as Lisa desperately cried for an answer, “Why won’t you tell me what you want!?” She began shaking with fear and blubbering uncontrollably.

Lisa suddenly noticed something odd about her attacker’s shadow: whoever it was had wild, untamed hair that sprouted out in all directions. She realized who it was. “Sideshow Bob?”

“Oh, so much for terrorizing you with the unknown,” the evil ex-clown said with some disappointment. He roughly rolled her over onto her back and put his face right up against hers. “But tell me this, smart girl: weren’t you just trying to assure me that you wouldn’t identify me?” Lisa couldn’t speak, so he raised his eyebrows before laughing malevolently at her.

Finally, she mustered up the courage to speak. “I’m sorry.”

“Sorry!?” he shouted while getting up off the bed. “Sorry for what? For letting me capture you so easily?” He began to pace around the room, gesticulating wildly as he continued. “Sorry for not knowing when to keep your trap shut? Oh, yes, like when you helped your brother to expose me and sent me to jail for all those years? Or are you sorry for spoiling all of my schemes every time I managed to find a way out of that hellhole? Or is it for shocking me -- for no reason at all -- when I was trying to save your father’s life?” He grabbed her shoulders violently and pulled her face up to his. “IS THAT WHY YOU’RE SORRY!?” he screamed.

Lisa jerked her head back and closed her eyes. She trembled and panted, trying to control her fear and keep from wetting herself. He held her close and kept glaring at the scared little blonde. Her tear-streaked cheeks burned every time he exhaled, even snarled, his hot breath over her reddened face.

Finally, she got her breathing under control. She opened her eyes and whispered, “I’m sorry for hurting you.”

Slap! He hit her face with an open hand and let go. She yelped while falling back onto the bed, closing her eyes tightly in fear. “Funny,” Bob noticed while standing up again. “I don’t feel sorry at all for hurting you.”

Lisa cracked her eyes open at first and, believing he wasn’t about to strike again, opened them and just stared sadly. “What are you going to do to us?” Bart turned his head slightly and looked up at him too.

“Oh, come now, Lisa,” he said in a condescending tone. “You both know that I’ve always wanted to kill your brother for what he’s put me through time and time again. But...” He just stared at them, not saying anything else for what seemed like an eternity. “But, it’s not like I didn’t have my share of chances: on the houseboat, at the dam, or after Grimes’ son was captured. So, maybe that’s not what I really want. True, the urge to kill is strong as ever, but I don’t feel I’d get true satisfaction by only killing you.” He leaned over and patted Bart on his head gently for a few moments.

“No, I think my thirst for vengeance won’t be fully quenched until I really hurt you,” he said before laughing wildly again. Lisa and Bart looked at each other in fear but didn’t try to say anything. Bob sat down on the bed next to Lisa and put one hand on her shoulder while running the fingers of his other hand up behind her head, taking a firm yet gentle hold of her hair. He turned her face up to meet his glare. “And, I think you’ll agree, that what could hurt Bartholomew J. Simpson more than anything would be making him watch helplessly as his adorable, sweet, innocent sister was tortured horribly right in front of his eyes.

“Who knows? Maybe she’ll accidentally die during her maiming. Heh, that would be the best of both worlds for me: I get to indulge in a little bloodlust, which I can convince myself was accidental while also depriving Bart Simpson of his better half, the one who does all the thinking. Yes! Best of all, you’d be a broken shell of your former self and completely powerless to ever oppose me again!”

Lisa went limp and sobbed uncontrollably, but Bart struggled for all he was worth, wrestling with the ropes between his legs and hands while trying to chew out the tape over his mouth. He jerked and tried to bend his waist and knees to move at all -- just anywhere. After relishing this for half a minute, Bob simply let go of the crying little girl and punched Bart in the side of his head. It was no use: he stopped struggling and began crying uncontrollably too.

“There, there,” the clown reassured him while rubbing his back and shoulder in mock compassion. “It will only hurt for, oh , I don’t know, the rest of your life!”

With that, he grabbed Lisa’s upper arms and made her stand on the bed, though her knees where shaking so badly that she couldn’t stay up by herself. While holding her by one arm, he unzipped her sleeveless red dress and yanked it down, revealing only a pair of white cotton panties. “Yes, that’s better, don’t you think, Bart? With her red dress we wouldn’t get to see all that blood.” He pulled the dress from her feet and, without thinking, Lisa lifted each foot in turn so he could take it. He threw it across the room and, after steadying the terrified girl, let her stand on her own: sniffling, shaking, crossing her legs in pain, and looking at him with the saddest blue eyes he’d ever seen.

Suddenly he smiled and ran two fingers down her face, wiping away a tear. “You know, all of my chums in prison would give anything to be in my shoes, or rather, my oversized shoes right about now. Ah, there are some appetites you just can’t fulfill in the big house.” He brought the fingers to his mouth and, eyes half closed, gingerly licked off her sweet tears of defeat. “Of course, mine were for decent Merlot and goat-cheese quiche, but perhaps I shouldn’t let this tender delicacy go to waste.”

Lisa winced and doubled over in fear and pain. Goosebumps went up all over her skin. “Please, don’t,” she choked out between pleading whines. Bart tried to tell her something, but his noises of protest couldn’t be understood. Humiliated, she continued softly, “I’m saving myself... for...” Bart was suddenly louder in his protests, but Bob already knew what she was about to say.

“Marriage? Well, you’re assuming that you live through the night,” he teased. Bart sighed in disappointment as Lisa gave Bob a curious look. “Oh, who do you think arranged for this ‘once in a lifetime’ dinner invitation that your parents couldn’t turn up, hmm? Rest assured that they’ll take up their hosts’ invitation to stay the night. I made sure of it.” He smiled at her. “Oh, and I must thank you especially, Lisa, for being such a good girl and babysitting. I thought I’d have to deal with some mindless boy-crazy girl planted in front of the refrigerator with the telephone receiver stuck to her ear, but you saved me that trouble, which, in turn, gave me extra time to enjoy with you.”

Between the pain in her bladder, her extreme fear and the degradation she felt, Lisa didn’t know what to say. Her mind was in a panic just trying to figure out what she needed to try to do first: free Bart? Placate Bob? Escape herself? However, Bob had something in mind, so he grabbed her hair again and pulled her towards him. “What do you do when someone says ‘thank you,’ Lisa!?”

Lisa shuddered before weakly saying, “You’re welcome.”

“That’s a good girl,” he said while easing his grip. “And good girls get a reward.” Instead of standing her up again, he put his face against hers and kissed her lips. She was too scared to resist as his lips pressed against her, working them back and forth warmly. Soon, his tongue began to stroke her mouth, firmly working its way between her lips and across her chattering teeth. It reminded her of Nelson, but it was more skilled and much more passionate. Also, its tender warmth was in stark contrast to the chill she felt through the rest of her exposed body.

Almost as if he sensed this, he brought her in close to his body, his arm cradling her neck and head behind her. With the other, he stroked her hair back, caressed her cheek, and slowly slid it down her neck, her collarbone, and onto her undeveloped chest. She tried not to react to the strange chills and twinges she felt at his touch and, instead, tried to wrap herself in the heat of his kiss. She kissed back, hard, even though she knew he only wanted to make her suffer.

He moved his lips off hers and kissed across her cheek to her ear while moving his hand still lower across her stomach. “I must not be doing a very good job of torturing you if you like it so much. Perhaps I should try something else.” He bit into Lisa’s earlobe, gently at first, but gripped it firmly between his teeth while teasing it with his tongue. Suddenly, he jabbed his fingers into Lisa’s vulva through the cotton panties, making her thrust her hips back with shock and pain. He matched her movements and dug his fingers into the top of her love zone, roughly touching, pinching, and squeezing her labia and roughly stroking her clitoris.

When he wiggled some more and hit her urethra, she went wild and pulled away hard enough to take her ear from his mouth. Lisa screamed, “No! Stop it, please! I can’t hold it!” A bit shocked at this, he stopped fingering her for a moment. She looked into his eyes and begged, “Please, I really have to pee!”

A wicked smile took over his face and he seemed to be staring off into space, as if looking right through her. He stood her up straight again and blinked once, slowly, while looking into her eyes. “Well, go right ahead.”

Lisa just looked at him in confusion, scanning his face with her eyes and trying to figure out exactly what he wanted her to do. She couldn’t possibly imagine what he was thinking.

“What’s the matter? Oh, you may be the most-mature young lady in all of Springfield, but you’re still only eight years old. And eight-year olds sometimes wet the bed,” he said flatly while standing up. “Come on! After all, it’s not even your bed -- it’s Bart’s. You know, the smell of your urine might be the only thing he’ll have to remember you by.” As she cried in shame, he untied her legs, eased down her panties and, still holding her waist, walked around the bed to Bart’s side. There he used his free hand to grab Lisa’s right ankle and lift her leg over her brother before putting both hands on her waist and making her squat over his face.

“Go ahead,” he told her kindly. He suddenly slapped her bare bottom and growled, “I can assure you, if you don’t go now and end up urinating on me later there will be Hell to pay!” Lisa wasn’t accustomed to being spanked, or ever hit by an adult. Unlike when Bart or other kids hit her, this made her feel like she was being punished for something that was her fault.

Sensing her sudden tenseness, Bob reached in and began massaging her clitoris and lips again, running his finger across her urethra and even flicking the outside of her vagina. She squirmed as he urged her, “Just remember all the times he was mean to you, hurt your feelings... or just really pissed you off, heh heh heh. Actually, Lisa, you’ll be doing him a favor: when they find him, your parents won’t be able to tell that he was crying like a little girl.” Bart felt tiny splatters of moisture on his face and forehead, but he realized they were only his sister’s tears as she quietly cried.

Bob shifted his hands to the small of her back and her lower stomach, just above her pelvis. He squeezed his hands together as hard as he could, but he didn’t have a lot of leverage. Frustrated, he impulsively hit her in the stomach with the bottom of his fist, making her cry in pain and start to fall over, but he used the hand at her back to grip her hair and make her stay up. Then he began alternating between rubbing and squeezing her private bits again and pressing her lower belly.

Through teary eyes, Lisa looked down at her helpless brother as Bob relentlessly tried to make her lose control. Finally, Bart slowly nodded at her while closing his eyes. With a final sharp breath, he inhaled and then scrunched his eyes and taped mouth tightly. Lisa knew he couldn’t hold his breath for a very long time, but she still had to force herself to let go.

Bob excitedly spread her lips open with two fingers as the first thin spray emerged from Lisa’s pee hole, but soon she couldn’t hold back at all and the warm yellow liquid streamed down onto her brother’s face, neck, and chest while splattering all over his bed, the headboard, and her own legs. So much was coming out that it also streamed down the inside of her thighs, across the backs of her knees, and then down to her feet. Bart turned his head from side to side, occasionally breathing through his nose while trying to endure his sister’s coerced assault. He tried to make himself believe that if he could just “take it like a man” then it would somehow save his little sister from the sheer humiliation.

Lisa was convulsing and bawling loudly as it continued steady for over a minute. Still holding the little blonde’s vulva open with one hand, Bob moved the other down to her behind and fondled the cheeks, back and forth. As her stream slowed down to a trickle, he cupped her left bum cheek awkwardly and jabbed his index finger right up to her asshole, making Lisa release a sudden hard spurt of piss onto her brother. Then, after a few seconds, he roughly jabbed and squeezed again, eliciting yet another geyser of smelly pee. He did this a few times, but each time the squirt was less and less, and Lisa was finally done.

Lisa’s blubbering subsided and she simply whimpered at the evil man’s painful ministrations. Her legs ached from being in such an awkward pose and she was visibly shaking from the strain. Finally, she opened her eyes and looked down at her brother. He was trying to open his eyes, but it stung too much so he kept blinking.

“Ahh, what a wonderful show,” Bob said with delight as he let Lisa stand up. “When I was a young boy I used to wonder how girls did that, with their ‘different equipment’ and all. And now I know.” Then, he looked down at Bart as he still struggled to see what was going on. “Oh, Baaaart, I’m so sorry that you didn’t get to enjoy the visual part of the presentation too. My bad.” He then nonchalantly spit on Bart’s face and then rubbed it in his eyes before finally wiping them off with a dry corner of the bedspread. “After all, the whole idea was for you to watch, wasn’t it?” The malevolent ex-con then used one of Bart’s pillow cases to perfunctorily wipe down Lisa’s crotch, thighs, and legs before tying her ankles together again.

Soon, Bart was able to see again but was still breathing somewhat erratically due to the uncomfortable and smelly wetness in his nose. With a quick yank, Bob ripped the tape from Bart’s mouth. “Ow!” he cried but was instantly embarrassed, seeing his sister still standing above him, shivering and naked except for her pearls and wet socks. He turned his head away, but Bob grabbed his chin and made him look up again.

“Oh no you don’t,” the large man commanded. “I’m putting on the performance of a lifetime, and I certainly won’t allow it to go to waste. Hmmm, maybe each time I catch you not watching I’ll just have to do something that gets your attention... like this!” With that, he spanked Lisa’s bottom a few times, much harder than before, immediately making her yelp and bringing fresh tears to her eyes.

The grimacing villain looked down at Bart, who was now staring wide-eyed at his crying little sister. “So, do I have your attention yet? Good. Now, where were we?

“Oh yes, deflowering Bart Simpson’s adorable know-it-all little sister,” Bob reminded them while looking up and down at Lisa’s quivering naked body. “Shall we, my dear?” he pretended to ask while taking hold of her arms and guiding her back down on the bed next to her brother. Though she kept quiet and didn’t resist, she was screaming on the inside, desperately hoping that they’d somehow be saved in that instant.

Sounding more fearful than brave, Bart cried out, “Don’t hurt her! I’m the one you want.”

Bob answered with a sneer. “Oh, Bart, you have a lot to learn. Sure, little Lisa may not be much to look at, but if she’s anything like your aunt Selma then I’m in for quite a ride.” He stopped for a moment and thought before adding, “Then again, if she’s anything like Selma, she won’t be much to look at ever.”

Lisa began to sob quietly.

Bart reassured her as best he could. “Don’t cry, Lis. That’s what he wants. We’ll be all right — I’m sure of it!”

“Oh, I’m so sorry, Lisa,” Bob told her, but his tone was exactly half-way between sarcasm and sympathy. Leaning over, he briefly stroked the hair on her forehead. “You are, truth be told, quite a lovely young lady who obviously takes pride in her appearance. I dare say you shant grow up to look anything like your aunt. Of course, we still haven’t determined whether or not you actually will have a chance to grow up at all, but don’t give up hope. That takes all the fun out of it.” He stood up and moved over to the foot of the bed, where he gingerly removed her damp socks as Lisa cried even harder.

“What is it!?” he demanded to know. “I just gave you a compliment. You should be, well, relatively happy.”

“Stop saying mean things about my aunts,” Lisa choked out. “Please.”

“Oh,” Bob said, genuinely surprised. “Well, then I’ll get right down to business.” He pulled a five-inch hunting knife out of a sheath on his belt and held it about a foot from Lisa, slowly turning it so that it reflected the hallway light in her face. Lisa froze in horror, staring at the blade as he spoke. “You know what this is, and I can assure you that I’m more than willing to use it if you should try anything. And, if you don’t fear for your own safety, just imagine what I could slowly cut out of your brother without actually killing him. Or perhaps even your baby sister, who’s sleeping so peacefully in the other room. My goodness! I hope you two don’t make too much noise and wake her up. Because then I’d have to,” he made a slashing motion with the knife before ending with, “silence her. Understand?”

Lisa could only nod.

“Excellent. Okay, since you’re a bit small we’ll have to loosen you up first.” He carefully dragged the flat edge of the blade down her pounding chest, across her heaving belly, and then slid it into her inner thigh. Lisa tensed up, closing her eyes and clenching her teeth as the cold metal touched her love lips. She let out a small squeak as he stopped. Then, he slowly dragged the blade down her left thigh, down her leg, and then suddenly stabbed at the rope around her ankles. Lisa jumped in place as the ropes fell off, freeing her legs.

“Now, I’m going to teach you something I learned all about in prison, after you two sent me there,” he scowled. After putting the knife on the nightstand, he unbuckled his pants and let them fall to the floor. His penis had already started to stiffen, pushing out on the Krusty boxer shorts he was wearing. Bitterly, Bob reminisced, “Yes, I learned a lot about this in prison, over and over again...”

In a flashback, Sideshow Bob and the other prisoners were sitting at separate desks in the prison classroom. A TV cart was up front, and a guard pushed a tape into the VCR. “Hi, I’m Troy McClure,” the set called out. “You may remember me from such correctional institution health education videos such as Soap on a Rope and Other Tips for Successful Showering and Your Heart And Why You Don’t Want to Get a Shiv Stuck In It. Today we will be talking about oral sex. First, let’s look at what diseases can be transmitted by oral-genital contact...”

Back in Bart’s room, Bob climbed onto the bed and pushed Lisa up to the headboard, pulling her up onto her knees. With a squishing sound, he got on his knees in front of her, right next to Bart. Then he pulled apart the front of his shorts, which had Krusty’s face on it, and slipped his semi-stiff tool out from where Krusty’s nose should be. “You love Krusty, don’t you? Now, it’s time to kiss his nose, Lisa. Don’t worry, I’ll talk you through it.”

Lisa hesitated, just starting at the perverted phallic face of Krusty. Bob gripped her hair with one hand, eliciting a yelp of pain from the girl. However, he pulled her forward with little resistance. “Come on, lick it. Just pretend it’s a lollipop.”

Bart begged, “Please stop it, Sideshow Bob! You’re already making her cry, so just leave her alone. It’s me you want!” Bart continued pleading but then started sobbing to himself.

Nervously, Lisa closed her eyes and blindly stuck out her tongue, though not very far. Bob pulled her forward, forcing it to make contact with his tool. At the first taste Lisa fought to keep from taking her tongue back in. Instead, she extended her tongue further while closing her lips tightly around it, trying not to let any of the taste actually get in her mouth. However, Bob’s penis hardened at her touch and he started guiding her around it and moving his hips so that it rubbed against her mouth as she clumsily flicked her tongue across the head and upper part.

Suddenly, Bob slapped the left side of her face, surprising her. “Bart! You’re not paying attention,” he reminded the bound boy. Bob gripped a soggy pillow and forced it under Bart’s head, making it too difficult (besides wet and stinky) to turn his face down into the bed.

“Come now,” Bob chided her. “That’s not how one really sucks on a lollipop. Open your mouth and suck the top a bit.” With his free hand, he gently pinched a cheek and then parted her lips. When she hesitated, he pinched her nose closed until she had to open her mouth to breathe. She looked up at him with pleading eyes. “No teeth!” Bob commanded as he gripped his shaft and ran the top of it against her lips, gums, and then the roof of her mouth. “Lick and suck a bit slower,” he told her, so she closed her lips around the end of his cock and rolled her tongue over the tip. Fully erect, it was about six inches long and a bit thinner than most, but to Lisa it looked like a deformed snake that was ready to strike. She closed her eyes and tried not to think about what she was doing.

“Now, you like music, don’t you, Lisa?” Bob asked without waiting for an answer. “So, just pretend it’s a harmonica and run your lips up and down the sides.” Bob guided her head back and to the side of his tool, making her kiss and lick up and down one side for a minute before switching her to the other. Then, he brought her head down underneath it, her lips pressing against his sack with his prick up beside her nose and across one eye. He twisted her head sideways and made her suck one of his balls before slowly drawing her back up, making her suck his cock's underside thoroughly.

Since Lisa was diligently obeying him, he let go of his penis and eased his grip on her hair. Afraid of what might happen next, Lisa actually increased her efforts in hopes of keeping her tormentor satisfied so he wouldn’t do something else to her. However, he was already reaching for her groin again and soon started rubbing and trying to work his fingers down between her legs. As his excitement grew, he fingered her more roughly, causing her to instinctively try to pull back, but he just tightened his grip on her head as a reminder. She just tried to resist the urge to escape from this latest assault on her previously unexplored slit.

Much to Bob’s dismay, Lisa was not getting wet at all. He had hoped that, despite her age, she would at least have some reaction to his ministrations. And while the idea of a tight virgin pussy was turning him on more and more, the thought of it being bone dry didn’t appeal to him at all. Without warning, he picked Lisa up by her upper arms and lifted her so that she stood on bent legs with her head and upper back against the wall. “I can see that we’ll need to do a little work here,” he said with some concern as he guided Lisa’s knees apart and pressed his face into her nether region. “Maybe I should have let you use the bathroom, after all. Hmm, now’s not a good time to stop and give you a bath.”

After staring at her cute little pussy for a moment, inspiration struck. He leaned to the left and pulled Bart up to his knees, making him face his sister. “Baaart, your little sister has a boo boo. I guess it’s up to you to kiss it and make it all better.”

Bart looked curiously at his sister’s cunny, having never seen one before. “She doesn’t look hurt there,” he observed.

Without hesitation Bob punched Lisa in the stomach. She immediately crumpled and slid down the wall, stopping with her neck and head still on the wall and her knees bent around her brother's head. As she cried quietly, Bob gritted his teeth and warned him, “Do what I tell you or she will be.” With that, he pushed Bart’s head into Lisa’s crotch and rubbed his mouth and nose against it. Reluctantly, Bart noisily kissed away, trying to keep from actually making contact, but his captor kept pushing his face in and rubbing it around. Finally, Bob edged Bart a little to the side and got a look at what was happening. “Oh, come now! Get in there and rub it with your lips. Use your tongue. Weren’t you paying attention to what I had your sister doing before?” He raised his fist again.

“I’m trying! I’m trying!” Bart protested as he clumsily ran his tongue over his sisters lower lips. Lisa gasped uncomfortably at this new low.

“Really, Bart,” Bob sighed. “Do it slower... okay, now move your tongue up and down. That’s good, now take that between your lips and massage it. Yeeeeeess.” Bob deftly ran a finger in and wiped off some of the juices that were starting to flow. He brought it to his nose, sniffed it briefly, and then raised his head to face the confused little girl. He lifted her head with one hand and made her look at his face as he slowly, deliberately, pushed his wet finger into his mouth. With great exaggeration, he moaned and closed his eyes as he sucked off the little bit of pussy juice he’d retrieved. “Mmmmm, you may be just a girl, but you are starting to taste like a woman.”

As Lisa stared back at him sadly, he realized that Bart was neglecting his assignment. “Pick up the pace, Bart. We only have six or seven more hours, and I think your sister is starting to like it. Don’t you, Lisa?”

She immediately bit her lower lip and tried to look away, but he lifted her chin up until she couldn’t help but look at him. “Well, do you like it?” Lisa just nodded slightly. “I already know you do, but Bart can’t see you — he’s too busy giving you pleasure. Now tell your brother how much you like it when he kisses your genitalia.”

After a sniffle and a few labored breaths, Lisa tried to speak but only managed to squeak, much to Bob’s annoyance. “If you don’t, that’s okay,” he said calmly while picking the knife up off the nightstand. “If he can’t satisfy you then I’ll just have to cut out his tongue.”

“No!” Lisa cried out.

“Ah, you can speak. I suggest that you do,” he said while tightening his grip on the handle. “Tell him, now!”

Lisa stared at the blade in fear as she spoke. “Bart. It feels good when you do that.” Bob stared at her and slowly tilted the knife down towards the back of Bart’s head. Lisa started talking much faster, “It feels great when you kiss me there. Don’t stop!” She hiccupped and began to moan in short pulses as she began to cry again.

Bob pulled Bart away and dropped him on his back with a squish. “My turn!” the tormentor cried out as he moved in and started licking, sucking, and fingering wildly at her exposed sex. Lisa’s squeaks of humiliation gave way to short moans of pleasure, which only made her feel more ashamed. Bob kissed, sucked and poked at her, occasionally making Lisa jump in surprise as he massaged out a good coating of her natural lubricant and spread it throughout her slit, between her legs, and even worked it into her tight asshole with his fingers.

Bob suddenly stopped and moved up to his knees, bringing his softening penis back to the young blonde girl’s mouth. Without waiting to be told, Lisa opened up and started licking and sucking it. He put his hands behind her head and pulled her forward, which was very uncomfortable for Lisa but she didn’t complain. His manhood quickly stiffened again and he began to move his hips, pushing it deeper into her warm, inviting mouth. Soon he was slowly humping her face and she had no control whatsoever.

Eventually, Bob got a little carried away and stuck it in too far, jamming it down her throat. Lisa gagged violently and tried to move but couldn’t, so she just started choking on it. Bob stopped and then slowly pushed it in even further for a few seconds, just to see what he could get away with. Her gag reflex tickled the end of his penis, but Lisa’s choking and attempts at coughing made him realize she wasn’t getting any air. He pulled out and gave her time to recover. She was coughing violently and spitting, though most of her saliva ended up on her lower lip and chin.

Bart yelled out, “What are you doing to her! Stop it! Stop it! Do it to me instead!”

Bob just smiled. Lisa had been choking, powerless to move, and he had even tried to make it worse, yet she still knew better than to bite him. “There, there, that’s a good girl,” he consoled her while gently stroking the side of her face as his penis rested inches from her mouth. He thought about taking Bart up on his offer, but he didn’t want that boy’s teeth anywhere near his manhood. “Perhaps it’s time we move on,” he said to Lisa as he lifted her up and moved her so she was lying flat on her back. Still between her legs, he laid down over her stomach and kissed her gooey lips while positioning his shaft between her legs, slowly moving it up to her clitoris and then down past her vagina. He let the glans rub against her back door.

Lisa began to weep softly, “Please, I wanted to save myself...”

“Oh, all right!” Bob said as he got up on his knees, much to Lisa’s surprise. However, he simply rolled her over onto her stomach, untangling her legs from his and then pulling her backwards up onto her knees. With her hands still tied behind her, her face landed on the damp bedspread, so she turned to the side and looked at her brother who was still helplessly lying on his back. He had to strain to see what was going on, but when he tried to look at her face she turned it towards the hallway instead.

“This was all the talk in prison, though they all said I wasn’t pretty enough to try it with.” Lisa began to squeal each time she inhaled, shuddering as Bob once again milked her clitoris and rubbed her vagina. He gathered her pussy juice and deposited it in and around her tight anus. She quivered as he began to rub his hot flesh stick across her slit, flicking it up and down. Occasionally, he pressed it right against her hymen, threatening to tear her cherry anyway, but he always backed away and kept working it until Bob Jr. was nice and slippery.

Without a word, the evil man grabbed Lisa’s hips and began rocking her slowly back and forth as he moved his own hips and positioned his tool at her pucker hole. “Now just relax and it won’t hurt, at least not nearly as much if you fight it.” He pressed gently at first, getting the tip of his pecker into the dimple, but then he started pushing with more force and grinding his hips, working it into the slippery spot. He looked down and let some saliva fall from his mouth, though it missed the mark and landed on her bum cheek. He rubbed it into the right spot with one hand before taking hold of her sides and rocking her again.

Lisa felt his throbbing meat as it pushed her apart and entered the wrong way, but she tried to think only about unclenching and letting him have his way. Hopefully, if he got what he wanted, he wouldn’t need to go any further. Mom always told me to just ignore it when kids picked on me and they’d stop, she thought. She didn’t realize it would hurt this much to take her mother’s advice. She let her tears fall but didn’t make a sound.

Bob finally worked himself about halfway in and then drew back. Going out, it actually felt a bit good to Lisa, like a relief, but soon he was pushing in again, this time a little deeper. His pace quickened and he worked it in a little farther, then farther still. At one point he stopped, waited a few seconds, and then pushed it all the way. She felt his loins pressing hard against her butt cheeks as he wriggled it around, celebrating his conquest of her little ass. He grunted in satisfaction.

“What’s going on?” Bart asked after so much time had passed without Bob saying anything and hardly a sound he could recognize. Lisa was too emotionally numb to say anything, and Bob didn’t give him the satisfaction of an answer.

Next, he slowly drew it almost all the way out, only to slide it back in rather quickly again. Lisa jumped at the sensation, but it was a little easier to deal with now. He slid it back and forth slowly a few more times, then pulled out completely. Lisa suspected that wasn’t the end of it, and she was soon proven right as he steadily pressed his penis inside her again, this time stopping halfway to tease her. Then, he quickly forced it the rest of the way in and began pounding her bottom, back and forth, making her grunt with each thrust. He went on pumping for a full minute before pushing all the way in, pressing hard against her bum, and stopping. The force of his tool lodged deep inside her small rectum made Lisa wince. She groaned in pain but didn’t try to move.

“What are you doing to my sister? Why are you hurting her?” Bart cried out.

Bob only focused on Lisa’s minimal reaction. “Oh, getting bored with this, I see,” he said casually. Perhaps I can find a way to make this a little more interesting for all of us.” As a final tease, Bob quickly thrusted forward one more time, shoving Lisa forward, before pulling completely out. Her stretched anus throbbed and didn’t close all the way. Any sense of relief she felt was overshadowed by the fear of what he meant to do next. She watched helplessly as Bob picked up the knife again and came back over her. He then rolled her onto her left side, facing Bart, before moving to his side of the bed. Then he rolled Bart onto his side, facing her as well.

When the boy looked at her she bent her head and averted her eyes, ashamed. “Are you all right, Lis?” he asked sadly. She just nodded without looking at him. Not knowing what else to say, he asked, “Did it hurt a lot?”

Bob answered, “Right now you should be worrying about your own ass.” He thrust the knife down behind Bart, making both children gasp. Lisa looked at her brother’s face, afraid of what she’d see. Besides a look of shock, he seemed all right as Bob pulled on the knife that connected the ropes on his hands to the ones on his feet.

“What are you doing!?” Bart cried out. Lisa was relieved to hear the anger and fear in his voice, an indication that he hadn’t been hurt.

Without answering, Bob slipped the knife into the back of Bart’s shorts and underwear before yanking it through the fabric. He pulled them down to Bart’s ankles and then lifted the boy’s right knee, spreading his legs.

“Aye carumba!” Bart yelled out. “Let me go you pervert!” he demanded indignantly.

“What?” Bob asked. “You wanted to know if it hurt, so you’ll get to judge for yourself.”

Lisa looked at Bart’s face, full of sheer terror and hopelessness. “Just relax and it won’t hurt as much, Bart,” she advised. “Pretend you’re pushing out a big one and had to stop for a rest partway.”

Embarrassed by her staring and icky advice, Bart groaned and tried to turn his face down into the wet bedspread. Bob spit generously into his hand and then worked it into Bart’s brown eye, even sticking a finger all the way inside for good measure. Then, he lined up his cock and steadily pushed it in, right to the end without stopping. Bart growled and groaned, even biting the bedspread despite its odor. He tried to take Lisa’s advice, pushing with his rectum, but in the pain and humiliation he couldn’t help but also squeeze his cheeks together.

Bob slowly moved his love salami in and out a few times before stopping all the way in. He leaned down and grabbed Bart by his hair, making him turn to face his sister. “I’m not into little boys, but doing this to you, Bart Simpson, is somehow very liberating. And I want to see your face.” He reared back up and looked at Lisa. She had curled her legs and body into the fetal position, except for her bound hands, and had her eyes closed tightly. “That’s okay, Lisa, you don’t have to watch. You already have a very good idea of what I’m doing to your brother.” With that, he resumed slowly pulling his meat out of the boy before plunging it back in again.

After a few minutes of this, Bart’s muscles were too tired to keep fighting back, so Bob began working himself a little up and down, side to side, to vary the sensations a bit. “Tired already, Bart? That’s okay, you’re still doing great. I’m sure that someday, when you’re old enough to be tried as an adult, you’ll make some inmate very happy.”

“Oh, Bart!” Lisa gasped as she opened her eyes. She wished more than anything that she could comfort him and take away the pain and humiliation he must be feeling. However, though she expected him to be crying, his eyes were wide open and his face was red with a burning, intense anger. She was genuinely confused.

Suddenly, much to both kids’ surprise, Bob began singing, “I am the model of a modern rapist pedo / Going at some poor waifs stuck living in a ghetto / It may make them cry or get quite upset, though...”

Unable to contain himself any longer, Bart spat out, “You know, I always figured you’d be the lead in ‘Ass Pirates of Penzance.’”

Bob busted out laughing so hard that it echoed off the walls of the tiny room while he paused the assault on Bart’s hole. Lisa was shocked at the evil clown’s reaction yet terrified that he’d kill her brother for insulting him. Bart was just confused by Bob’s reaction, but also very disappointed. After a few more guffaws, Lisa’s fears were intensified as Bob picked up the knife and, letting himself slip out of his brother’s bottom, moved over towards her.

“I’m sorry!” Bart called out. “I won’t say anything else — just don’t kill her! Please! I’ll do anything, man!”

Her mind in a panic, Lisa thought of rolling off the bed and running away, but she was too scared to move her unbound legs. As the wicked Savoyard pushed her onto her stomach, she realized that she couldn’t get out of the house quickly with her hands bound; even worse, if she did get away then Bob would just kill Bart and Maggie. Though she had many other reasons to, it was that thought which made her start bawling again.

Bob cut the ropes from her hands. “Seriously, you are just wound way too tightly, Lisa,” he complained while rolling her onto her back again. She looked at him as he leaned over her, pants less, smiling, his hard-on pointing between her legs. “I just need your help making your brother, hmmm, a bit more responsive again.” He leaned back and guided her up onto her hands and knees, facing her brother’s torso. He took her left hand firmly and placed it on Bart’s scrotum and made her get down on her elbows. “That, you just pet and squeeze. Now, since you were doing such a wonderful job for me before, and Bart did fellate your genitalia for a while first...”

Without waiting for more instruction, Lisa leaned her face in and started flicking her tongue across her brother’s limp penis. It jumped as soon as her warm tongue touched it and she gently suckled it. Bob watched in amazement as Lisa, with her eyes closed and her cheeks stained with tears, massaged Bart’s nuts while kissing and sucking on his Simpson maker. Bart clenched his jaw and tried to fight it, but a ten-year old boy can’t even control it when he’s sitting in match class, never mind when a cute girl is running her soft, moist mouth up and down its length. Soon, he was at full staff and, under Bob’s watchful, leering eyes, Lisa kept running her lips and tongue up and down its sides and occasionally sucking the tip.

“Now, take it in slowly and get used to it gradually,” he instructed her as his own tool got so hard that it ached.

“But his is bigger!” Lisa complained.

Bob’s eyes went wider than saucers and he punched Lisa in the side of her face. She collapsed on her side, crying hard as blood trickled from her earlobe. “I’m sorry! I’ll do it! I’ll do it!” she begged hysterically.

“Lisa!” Bart yelped. “Bob! Please! I’ll let you buttfuck me all you want, and I’ll even kiss it if you. Please! Just stop hurting my little sister!”

Terwilliger immediately regretted his harsh response, and he further realized that, from her perspective, Bart having a larger wang was actually a bad thing. He even felt like apologizing but didn’t want to show any more weakness. Instead, he put his right hand behind her head and leaned in before kissing her squarely on the lips. He wasn’t sure why, but it had seemed to calm her down before, and it would make it too difficult for her to cry. Besides, there was something wonderful about kissing a girl who was as intelligent as him. Correction: as intelligent as he is.

Lisa felt her terror melt away. In fact, she was so emotionally drained that she couldn’t tell what she felt anymore. Before she knew it, Bob had guided her back to her brother’s half-hard cock and, with a final sloppy kiss, moved her lips from his to it. Almost in a dream state, she began to work it over again, this time taking it into her mouth and throat, a little deeper at a time, while Bob repositioned himself behind the boy. “That’s a good girl, Lisa. Make your brother feel really good and I’ll give you an A.”

Bart’s rear entrance had dried a bit in the meantime, but Bob plunged ahead anyway, if a bit gingerly at first. Soon he was working away slowly, enjoying the sensations passed to his shaft by Bart’s reaction to his sister’s efforts. He reached with his right hand and took Lisa’s, which he then placed on Bart’s ball sack again, both of them rubbing and petting it.

He bent forward around Bart’s back, resting his chin on Bart’s neck and whispering in his ear. “Bart, do you know why I’m going slowly now?” he asked without waiting for an answer. “You see, when you ejaculate, your anus and other muscles have involuntary convulsions that help you ejaculate with more force, and it’s a great part of orgasm, in my opinion. However, with my John Thomas holding your backside open and pressing on your prostate, it will be almost impossible for you to have a satisfying climax. In fact, it will be very painful and you’ll actually feel like your cum cannon is going to explode because all the semen got stuck inside. It’ll still be very sensitive afterwards and, for a while at least, you’ll dread the thought of ever coming again.

“Meanwhile, your anus will want to close up very tightly. Perhaps you’ve experimented on yourself and know this to be true? Sure you have. Anyway, if what I’m doing is uncomfortable now, it’s going to get a whole lot more painful. Shhh! Don’t tell your little sister. She thinks she’s making you happy, and you wouldn’t want to hurt her feelings, especially after all she’s been through tonight.” He waited for Bart’s reaction, a resigned sigh, and then began rolling his hips and poking the boy with harder thrusts. Bob’s nutsack caressed the inside of Bart’s left thigh as he methodically and quite literally fucked the shit out of him.

He weaved his fingers with Lisa’s as they played with the helpless boy’s sack and stimulated him on both sides. Soon, Bob could feel Bart’s sack tightening up and hear his breaths getting shorter. The boy’s face was grimacing as he tried to fight back the building sensations, but it was no use. Bob waited as long as he could for the right moment and suddenly pulled back, taking his cock out of the boys ass and separating him from his sister’s mouth.

He grabbed Bart’s penis with his left hand, jerking and squeezing while still making Lisa rub his balls. Bart gasped and cried out. As Lisa opened her eyes to see what was happening, Bart shot off a load of gooey boy juice in her face, landing across her left eye and cheek. She blinked and then started rubbing it off with her free hand as another hard spurt landed across her mouth and on her nose.

Bob smiled and explained, “Get a good taste, Lisa. This could be helpful for you making friends and keeping your grades up later on in life.”

As soon as she could see again, she tried to move forward to take it in her mouth, lest Bob get upset, but his hand kept her from doing more than sucking on the tip as Bart was rubbed into pumping out a few more spurts into her waiting lips. It tasted salty and sour — just horrible, but she didn’t dare spit it out. Instead, she let it drizzle out of her mouth, onto Bart’s retching shaft. Bob finally let go of the boy’s tool. Meanwhile, Lisa kept licking and mouthing Bart Jr. until he started to go soft, trying to swallow as little as possible.

“Bravo! Bravo!” Bob commended them. “You see, Bart, I just couldn’t go through with it. After all, she went all over your face earlier, so it just wouldn’t have been fair. Besides...” He slowly forced himself into Bart’s asshole again, making the boy bite his lower lip and moan in pain. “This is much tighter now.” He began to drive in and out, relishing Bart’s tightened insides. “Lisa, be a dear and get some towels, maybe a few of your sister’s wet wipes. I’m going to need to clean up in a minute,” he grunted. “Oh,” he said while picking the knife up again, “I trust you’ll be back quickly, not using the phone or leaving the house.”

Though her legs were still sore and her bottom smarted, she got off the bed and started walking towards the door. As Bart moaned and whined, her legs felt weaker, her knees wobbled, and her hands shook as she got to the doorway. She thought this might be a trick of some sort, but she didn’t know what else to do. Somewhat dazed, she steadied herself and walked towards Maggie’s room as Bob started commenting on how close he was. She quickly got the wet wipes and hurried to the hall closet, getting out towels as Bob’s exclamations became louder. Lisa had to get back before he was done, to both prove she had obeyed him and to keep him from doing anything else to her brother.

Meanwhile, Bob shoved himself in deeply and cried out, “Oh my!” He tensed up and squirted inside the precocious boy a few times; then, he carefully worked his sensitive shaft in and out, just a bit, to get the last few squirts into Bart’s rectum. Bart barely felt anything deep inside, but soon he felt the gooey cum leaking out of his behind. Bob squeezed Bart’s cheeks together as he withdrew, trying to squeegee off any yucky stuff that had stuck to him. For the rest, he simply used the pillowcase as more dirty semen drizzled out of Bart’s stretched hole.

When Lisa walked back into Bart’s room, her brother was quietly lying on the edge of the bed, on the side where she had been for most of this horrific evening, and he was still wincing with pain. “Ah, thank you!” Bob’s voice boomed from the shadows behind her. Lisa jumped with fright and couldn’t move as Bob walked to her side. She turned to face him and saw his limp, dirty penis hanging down, a strand of cum still hanging off of it. “What are you waiting for?” he asked.

“Oh,” Lisa said as she dropped the towels and pulled out a wet wipe. With only a little hesitation, she wiped off his mons and then wrapped it around his penis, gently working off the traces of her and her brother’s “dirt” off of it. She was adept at cleaning her baby sister, so that part didn’t really bother her so much, but she had a hard time dealing with his patch of pubic hair. She wadded up the first wipe and tossed it at Bart’s trash can, missing. She hesitated, thinking she should pick it up, but instead pulled out another wipe and gently massaged her tormentor’s loose scrotum, working it over until she realized that almost nothing had gotten on it. She worked the pubic hair at the base of his shaft a bit harder, using a few more wipes in the process.

To Bob’s surprise, he began to stiffen up as the little girl wiped and cleaned his package. Her expression was like that of someone taking a test or doing a lab experiment, not a scared victim. Finally, she gave his growing member one more pass and, certain that it was clean, tossed the wipe, again missing the target, and bent down for a towel.

When she stood up again, Bob grabbed the towel from her unexpectedly and then, oddly, draped it around her shoulders and back. Suddenly he pulled it tightly around her arms and gripped the ends together in front, immobilizing her. “You did a much better job than I expected, Lisa. I dare say it looks clean enough to eat off of.” Then he smiled as fear ran across her face and goose bumps formed on her arms. “As a matter of fact, why don’t you test that theory.” He drew her in close.

Knowing what he wanted, most of the fear dissipated quickly and she complied. She even realized that he had positioned Bart and her so that Bart could see everything. Leaning forward, she opened her mouth and took the tip in, massaging the head with small circular motions of her tongue while caressing the end of the shaft with her lips. Bob pulled her in a bit closer, so she moved her head forward and took it in farther before backing off a little bit. Again she went forward on it, taking it all the way to the back of her tongue. Having choked several times on Bob and her brother, and knowing that she could back off in an emergency, she was able to mostly control her gag reflex as she took it in deeper. Meanwhile, she ran her tongue most of the way around his meat while also gently squeezing with her lips.

“You can go a little faster. It takes more work the second time,” he explained as she got used to moving in and out a little more quickly, then a little more still. Her neck and legs strained, so she slowly lowered herself onto her knees, and Bob, still gripping the towel, spread his legs wide and bent his knees to accommodate her. With his free hand, he roughly petted her hair and stroked her cheek. “Oh, yes, you’re really good. It’d be a real shame to kill you after how good you’ve become.” Lisa didn’t know what he meant to do anymore, and she really had no way to react. Bart, however, felt pain in the pit of his stomach because Bob was showing a proclivity for saying he’d do one thing and then doing the opposite. His aching butthole was a powerful reminder of that lesson.

Still, watching his little sister sucking on Bob’s cock, as she had sucked him off so wonderfully earlier, was starting to make him hard again. Worse, there was no way he could hide it, so he just prayed that neither of them would notice.

Bob looked at Lisa’s beautiful little face as she sucked away at his manhood, struggling to keep her head up enough and her eyes closed. If not for the tears, the red cheeks, and her expression of utter defeat, she’d be a little blonde-haired angel. He felt himself getting close much sooner than he thought possible, so he pulled back. Without warning, he pulled Lisa to the floor by the towel and then let it go. He grabbed the wet wipes and then spread her legs. “Front to back, right?” he said while starting to clean off her reddened vulva and back to her dirty bum. He quickly used up several wipes, cleaning her private parts and then working down her thighs to wipe away most of the remaining pee. Then, he looked down at her lying on the floor, legs spread, arms limp at her side, and a look of dreadful anticipation on her face.

He grabbed one more wet wipe and then turned sideways above her. Gently, he brought it down and began to wipe her tear-stained cheeks off before carefully cleaning Bart’s jizz out of her eyes. He also got the snot that was stuck under her nose from all her crying, and then even wiped out the inside of her lips and teeth. He flicked it away on the floor and then looked into her eyes. Lisa looked up at him with wide eyes and inhaled deeply through her nose, expecting another kiss. He didn’t disappoint her. He brought his lips against hers, and this time she surprised him by kissing back hard and sticking her well-used tongue into his mouth. He put a hand behind her head and reciprocated. Meanwhile he tickled his way down her neck and started fingering one of her nipples.

Bart couldn’t help but watch as the large-footed man and his sister made out. Bob moved his hand down further, tickling her ribcage and belly before going back to her privates. Sliding the tips of his long fingers between her pussy lips, he gently rubbed and squeezed her hood and teased the clit inside. He darted his pinky down lower, feeling that she was becoming wet again. He raised his head and looked into her face. “See, you’re starting to feel better already.”

Lisa turned her head sideways, to Bart, but he was staring at her so she quickly turned her face towards the hallway and looked down. Bob simply turned her head back to meet his gaze and smiled. “Come now, you’re the only one of us who hasn’t had any release yet.” He kissed her again, seemingly working his entire face into her until she was as caught up in it as he. He pulled away quickly, leaving her to shudder and let out a sigh of longing. He brought his face down and licked her tiny ear before breathing into it hotly. “If anyone asks, it was just Stockholm syndrome.”

Bob licked and sucked on her ear for a moment before working his way down to her cheek and neck, then quickly to one nipple. When she seemed to have little reaction to that, he moved on to her belly, sticking his tongue deep into her navel. She felt a strange tingling sensation that shocked her lower body, making her squirm uncontrollably and put her hands on his head to push him away. However, her lingering fear made her stop short of doing that, so she instead rubbed and massaged his wild, palm-tree-like hair as he mercilessly teased her sensitive spot.

Bart was feeling more excited and tried to turn himself over, despite the other side of the bed still being wet with Lisa’s golden spray. As he writhed in his bonds, his hard penis rubbed slightly against the bedcovers and caught him by surprise. He stopped and then, tentatively, tried to reproduce the feeling again by slowly moving his hips and back. He continued watching his tormentor on his sister as he slowly, carefully, stimulated himself as best he could.

After a minute or two, Bob put his hands over Lisa’s, holding them up to his head as he moved down to his target: her slit. He kissed it gently at first, but without pulling away he then slid his tongue inside at the top and slowly, lovingly, drew out little circles. He slid down further, crossing her clitoris, and dabbing at her closed pee hole. That made her tense up and groan in discomfort. Realizing this, he moved on, going to her love hole, where he kissed and tongued around the outside. Despite her feelings of apprehension and fear, Lisa couldn’t help but moan appreciatively at his loving attention. She continued rubbing his hair and face while spreading her legs even wider for him. She felt something building inside her, like the feeling she used to get while thinking about Corey, but much stronger.

When Bob raised his head and smiled at her, she couldn’t help but smile back. He leaned forward and kissed her again, making her taste her own girl honey. Bending forward, he continued to kiss her mouth and face while bringing his prick up between her legs. She gasped when she felt it rubbing against her slit. He slowly drew is back and, with careful hip motions, flicked it up and down across her sealed entrance.

“But...” Lisa quietly protested in his ear.

Bob raised his head and looked into her fearful eyes. “Lisa, my dear, you are about to gain a very special distinction: a woman who lost her virginity twice in one night.” Lisa gasped in fear. He put his arms around her and deftly rolled over onto his back, landing her on his stomach with her legs around him. “Don’t worry. This will make it a bit easier for you to take.” She had heard how much the first time hurts even for a grown woman, so she expected it to be excruciatingly painful.

He squeezed her hips with his hands and raised her up onto her knees while shimmying forward to line himself up with her. He started teasing her groin with his penis again and she began to whimper, so he used one hand to guide her head to rest on his chest, with her face looking in her brother’s direction. Then, he grabbed himself with that hand and brought the other to the small of her back, steadying her as he found her entrance and worked the head of his cock into it. Every time he pressed in a bit, the thin skin protecting her insides would push it aside, so he brought his hand up to guide it better. He brought his thumb up to her slit and rubbed her clitoris while moving the tip of his penis up and down at her tender opening.

Lisa couldn’t help but get wetter as he worked her love zone so expertly. Obviously, Bart’s earlier comment was way off: he definitely knew how to work a girl, even if he didn’t always know how to treat her. Slowly, Lisa began moving back and forth, matching Bob’s motions and rubbing herself a little more. Part of her just wanted to get it over with, but another part was anxious to find out what new feelings she’d be experiencing next.

Feeling her juices dripping down his tool, Bob pressed down on Lisa’s back while moving up with his hips and butt cheeks. Lisa began to pant and bite her lip as she felt her cherry bulging into her atop Bob’s pocket rocket. She tried to relax her muscles, even though she’d never tried to use some of them before, and spread her legs open a bit more. Still not in, Bob pulled her down harder as her knees slid out. Lisa felt herself tearing as a wave of pain shot through her. She yelped and imagined that this was what being stabbed felt like, but it wasn’t over yet.

Returning to squeezing her legs as hard as she could, she was able to hold herself on her knees again as Bob slowly made small strokes in and out, ignoring the blood trickling down his penis, hand, and pelvis. He had to tense up his erection while getting it beyond Lisa’s frontier and was worried that it had softened too much, but now he felt more excited than ever. Taking his hand away, he kept working himself into Lisa’s love hole. He moved his free hand to stroke Lisa’s face, but when he realized it was bloody and switched it. He wiped away the tears that had barely formed in the little girl’s eyes and then stroked her cheeks lovingly. He even paused to lean forward and kiss her forehead.

She began to move again, trying to help Bob and get this over with. Bart looked in amazement as Lisa absentmindedly brought her arms up to Bob’s side and began feeling his sparse chest hair between her fingers. Bob was making more progress now, and she winced each time he got a little deeper inside her until he was almost completely in. Then, despite the pain in her vagina, she felt something different as the top of his one-eyed snake began rubbing up inside, a few inches above her opening. She gripped his sides as the mixture of pain and pleasure ran through her.

Having opened her up just enough, Bob began taking longer strokes, back and forth. Every few times, he’d stop deep inside her and wiggle his crotch around to both tickle her insides and stimulate her clitoris. He’d also read that the clitoris had an inner structure that went all the way under the pussy lips and surrounded the vagina proper, though Wikipedia had a warning that this could not be confirmed. “Meh, better safe than sorry,” he said out loud, without thinking, as he carefully rocked his hips to massage as much of the young girl’s zones as possible.

As she lay pressed against him, his deep voice had run through her and added to the building sense of euphoria she was experiencing. “Oh, yes, tell me more,” Lisa replied, though she hadn’t heard exactly what he said.

Bob stroked her head again while feeling and kneading her buttocks with his other hand. “Oh, Lisa, you are a fantastic young lady. If not for our age difference, our completely-opposing political views, and the fact that I want to kill your brother, we probably could have been wonderful together.” He kissed her forehead again. She looked up and pushed herself up to his face, almost letting Bob Jr. slip out of the pussy that they’d just spent so much effort getting it into.

Without a word, she kissed him on the lips and then, to his surprise, pushed herself back and took his cock all the way back inside of her. Bart was so surprised that he stopped trying to rub the bedspread, though it wasn’t doing much for him anyway. Lisa gripped Bob’s chest, at his nipples, and pushed herself up. With her back arched, she began to ride him, trying to concentrate on the strokes of his hot rod whenever it made her feel best. Though it took a few tries to synchronize their motions, she and Bob were matching each other’s moves.

Missing the warmth of the little girl pressed against his chest, Bob bent forward and tried to kiss her, but she was angled too high. He laid back again and just played with her tiny dark-yellow nipples between his fingers. Lisa closed her eyes and started breathing hard as she fought to keep in sync, but her legs were tiring and her excitement was getting the best of her. Sensing this, Bob grabbed her hips and, though difficult at his angle, pushed and pulled her body back and forth. The guiding was enough to get her back in step. Bob started bucking harder as Lisa dug her fingers into his skin. He gripped tightly onto one of her bum cheeks and pulled it aside, letting the cool air all the way up between her crack.

“Oh Buddha, oh Buddha, oh Buddha...!” Lisa chanted as she felt something strange building up — strange but wonderful. Suddenly her insides tensed up around Bob’s cock and her anus clenched for a moment, then released. “Aggh!” she cried while falling forward on his stomach and chest. The sensations ran through her again, shaking her insides uncontrollably. Bob took over all the work, driving in and out of her as she experienced her first orgasm. He could feel what was happening inside of her: it wasn’t strong enough to affect him much directly, but the thought of making this cute little girl cum suddenly drove him insane with lust. He drove into her harder several times as she started to come off her contractions, and soon he shot off inside of the petit blonde, even more forcefully than before.

Lisa lay on his chest, covered in perspiration and catching her breath as the last pulses of Bob’s orgasm finished. With a smile on his face, he stroked her hair and back as she calmed down. He sighed and raised his head, noticing just a tiny bit of drool on the corner of Lisa’s lips. He tried to rub it away, but she moved her head forward and took his finger into his mouth, sucking and gently biting it with her eyes closed.

“Hmmm, I should have asked you to use your teeth earlier,” he said sweetly. Suddenly, she remembered how this had all started and tensed up, pulling away from his finger. “Oh, don’t be like that,” he complained while sitting up. Realizing what she had done — what she made happen — she turned her face away from him and started sobbing quietly. She felt his softening penis plop out of her as he put his arms around her and held her tenderly, just hard enough to keep her from pulling away.

“Well, it was good while it lasted,” he said before looking away. He noticed Bart laying there, his erection hanging over the edge of the bed as he breathed slowly. Bob let go of Lisa for a moment as he pushed himself up. Then, he stood her up and turned her towards the bed. “If you don’t want to be with me anymore that’s fine, I suppose, but it looks like someone else could use your help.”

Lisa and Bart looked up at him in utter shock. “You didn’t think I was finished with you two yet, did you? Anyway, Bart, I believe that I’ve loosened your sister up for you, and you certainly seem ready to go.” Bob guided Lisa over to the bed and pushed Bart on his back. He lifted Lisa over him and put her down between his legs, her knees together. Bob grabbed an ankle and moved it outside of her brother’s leg, but he stopped after gripping her other one.

“No, I think a little variety is better,” he said while using his grip to turn Lisa onto her back. She landed in the damp, smelly side of the bed. Bob grabbed his knife and cut the ropes on Bart’s hands before forcefully rolling him on top of his sister. He lifted himself on his elbows, on either side of her, and looked down at her deeply sad face.

“Bart!” Bob barked as he put the knife against Lisa’s neck. “Here are your two choices: either I stab her or you ‘stab’ her — get it?”

Bart started to cry, which made Lisa’s eyes well up as she reassured him, “It’s okay, Bart. I don’t care what happens as long as he doesn’t hurt you or Maggie.”

“Sorry, Lisa,” he said. “I don’t want him to hurt you anymore, but I can’t...”

“Yes you can,” Bob said while picking up Bart’s hips and pushing him forward. Though Bart’s ankles were still tied and bound with his clothes, Bob pushed his knees apart, reached between the boy’s legs, and grabbed his still hard cock. “See, you couldn’t stop yourself if you wanted to.” Bob pressed it inside Lisa’s dripping box, easily pressing it in the stretched, cum-soaked opening. Bart closed his eyes in shame.

“It’s okay, Bart,” Lisa told him. “I can barely feel anything there now.”

Bob snickered and then pressed Bart forward, getting him completely inside of her. “You know what to do, Bart.”

Reluctantly, Bart started moving his hips, rubbing his love stick inside of his little sister. Soon, he felt the pressure building and tried to slow down, but Lisa started breathing heavily and put her arms around him. “Let’s get this over with,” she said weakly while pulling him deep inside. She began to push back as he pumped her harder. She brought her arms up to his head and kissed his cheek. “I love you Bart, no matter what.” She gripped him tightly as her orgasm began to build up again.

“Oh, how sweet,” Bob commented as he gave Bart’s butt an extra push.

“Right back, ahhh,” he said as his power tool spasmed inside her, shooting more boy juice deep inside of the little girl. Though it was sensitive and hurt to move it, he kept going as Lisa bucked back.

“Guhhh!” she grunted as her second, somewhat weaker orgasm came. She rubbed against him a few more times, milking what she could out of this one, but she soon stopped.

“Hmm, perhaps that was a bit too much,” Bob wondered aloud as he brought the knife to Bart’s feet and cut the ropes. “I probably should have given you more time between orgasms. Do you think so?”

Bart rolled over, off of his sister, and sat up. “I just can’t believe you actually butfucked me! And after you did Lisa — Ewwww!”

“Oh, Bart,” Bob answered gleefully. “For all the times you figuratively fucked me up the ass, it was only fair. Besides, you said you didn’t want me to hold back — that I should really scare you. Well, not that I don’t have other thoughts in mind... Lisa, are you all right?”

Lisa was still lying on her back, panting. “Oh, role playing fucking rocks! But for the first time in my life, I’m actually glad we don’t have school tomorrow. I’m exhausted.”

Bob and Bart looked at her in surprise and then laughed. She sat up and joined in their guffaws. “God, Bart, I hope you remembered to put the plastic mattress cover on. This reeks.” She started to take the sheets off the bed while mumbling about checking Maggie, doing laundry, taking a bath, and other tasks to be completed before morning.

Bart replied, “Yeah, yeah. If any got on the floor I’ll just tell Mom that Maggie’s diaper came loose while we were playing in here. She’ll be so happy that I paid attention to her that she won’t care.”

“Anyway, I’d better get back to prison and try to get some sleep before breakfast,” Bob interrupted. “Next time, how about you two catch me breaking in and, not believing the police are capable of dealing with me, you two decide to teach me a lesson?” Lisa tiptoed over and opened her arms as he knelt down and put his arms around her waist. He lifted her into the air as they kissed deeply.

“Geez, you’re almost as bad as Mom and Dad,” Bart complained. “Anyway, we really need to find a fourth ‘cause, no offense Lisa, but I’d rather kiss a monkey’s butt than my own sister. How about Sherri or Terri?”

Bob and Lisa busted out laughing and, once he realized what they’d heard, he laughed with them.
The End
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A Prisoner's Tail