5 comments/ 104776 views/ 39 favorites Seven Tasks of Poor Carrie By: storyteller1023 "Hey, are you almost done in there? I have a hot date tonight!" "Just another moment," Carrie called back. She was standing in the bathroom of her hotel room, admiring how her brand new violet prom dress clung to her body. "Beautiful," she said quietly to herself. "This is gonna drive Andy up the wall!" She was a beautiful young brunette teen-ager with bright emerald eyes and just a hint of freckles dusting her skin. Tonight, she knew she was going to be the object of every boy's desire at the prom. Tonight was going to be unforgettable. Brushing her silky long hair with one hand and downing another swallow of Jack & Coke with the other, Carrie was ready to start the evening. She took another long glimpse at her body, staring somewhat dejectedly at her modest bustline. She had just turned eighteen a few months ago, and it looked like a pleasant B-Cup was all she was going to get. But no matter, she mused. She may not have the rack, but she certainly had the best ass in high school And tonight, when Andy came back with her to the hotel, she was going to let him take her back there......she was actually starting to get wet just.... "Carrie! Shit, come on!" Tommy had always been a bit impatient, but he was a sweet brother for doing this. Buying the alcohol for her, renting the room in his name so Mom wouldn't find out.....it wasn't fair to keep him waiting. Carrie opened the door and stepped out of the bathroom, spreading her arms and showing off her dress. "Ta-da!" Tommy was leaning back in the bed, drinking a beer and watching some racy Cinemax movie. He smiled and gave her a thumbs up when he saw his younger sister in her prom dress. "Not bad, sis.....you look a lot better than my prom date did!" Carrie blushed and waved him off. It was only her brother, after all, but he was a handsome, rugged jock who had been with more than his share of young women. He didn't make light compliments, and he never said anything that he didn't mean. "Thanks again for everything, Tommy," Carrie smiled excitedly, grabbing her purse and shoes. "Ah, don't worry about it," Tommy winked, finishing his beer and turning off the television. "You only have one senior prom, so you gotta make it a good one. Just be safe, and for shit's sake, don't do any more drinking until you get back to the hotel room for the night! Mom would rip me a new one if she found out I was getting booze for you and your boyfriend." Mischievously, Carrie swallowed another big gulp of her drink and licked her lips at her brother. "I'll be good," she purred in a sing-song voice. Tommy had heard that one before, and he just rolled his eyes. "Let's get going, I'm supposed to meet Sarah for a movie in an hour." The two were just about to head to the door when there was a sudden, unexpected knock at the hotel room door. "Were you expecting your boyfriend to come pick you up?" Tommy asked his sister. "No, I'm meeting him at the school. He doesn't even know what room I'm in," she shrugged, taking another big drink. Tommy had a suspicious feeling, and stopped Carrie from drinking any further. "Why don't you hide the booze," he suggested in a hushed voice. "Just get in the bathroom for a second." Carrie obliged, taking the seven assorted bottles of alchohol with her, as Tommy opened the door to a crack. What he saw caused his throat to tighten! Three people were standing outside the hotel room door, all of them with a serious glare on their faces. His eyes took in the most intimidating details immediately-----badges, holstered guns, eyes hidden by sunglasses. It was a trio of police officers....and his underage sister with alcohol on her breath was just a few feet away "Is.....is there a problem?" Tommy exhaled The police officer standing closest to him, a tall woman with a clenched jaw, just stood there, looking around the hotel room with a quick glance. She was a few inches taller than Tommy----probably 5' 11-----but even if her height was being inflated by her boots, she didn't look like the sort of woman you could push around. She couldn't have more than thirty years old. She was a giant compared to the other female cop, a young, short Hispanic woman who had the physique of a pixie compared to the taller officer. She was looking around the parking lot of the hotel, as if to see if anyone else was watching. Flanking the tall woman on her other side was a large cop that looked like a tank. Six foot four, bald, and angry looking. Tommy's mind angrily reminded his body not to begin urinating. "I'm Officer Erika Tack. As you know, it's prom night, and we routinely patrol the area to ensure that there is no underage drinking." Tommy took a deep breath, hoping that his younger sister would keep quiet while he tried to talk himself out of this. "I graduated high school years ago," Tommy began, happy that he didn't have to lie. He was never a very good liar. "I'm not going to any prom tonight." The short Hispanic woman gestured towards a pink Volkswagon with her nightstick. It was decorated with blue and pink balloons and ribbons. Tommy felt his throat tighten up again. "Are you telling us that this little crap bug isn't your car?" "N-no, it's not mine," he stammered. "That's funny," said the tall man, taking off his sunglasses and glaring intensely into Tommy's eyes, as if wanted to shove his head through the television. "According to the front desk, that car is registered to this room. Are you lying to us, boy?" His voice sounded like a truck barreling through a tunnel, and the thought of it colliding into him caused Tommy to subconsciously take a step back. "It's my sister's car, actually," he finally admitted. The three officers looked at each for a moment, and seemed to nod in agreement. Officer Erika stepped into the frame of the doorway, and pointed at Tommy. "Step aside," she demanded in a quiet, but serious tone. Tommy hesitated for a second, until the giant man put his fingers on the handle of his nightstick and cleared his throat. Tommy backed against the wall immediately, and the three officers stepped into the little hotel room. Erika looked around the room for a few moments, and sniffed the air. She grunted, unsurprised. "Have you been drinking?" "That's not illegal," Tommy said defensively. "I'm over 21." "Are you here alone?" she continued, pressing her nightstick against one of the two beds. The sound of the springs bouncing filled the dreadfully silent room, and Tommy looked at his feet, unsure of what to say. "Sit down on the bed," she finally instructed, as the male cop walked to the bathroom door. He stood there for a moment, looking at the door, and then pounded against the wood three times. His fists were the size of footballs, and the noise filled the room with an deafening echo. It took only a few seconds for Carrie to sheepishly open the door to find the biggest man she'd ever seen staring down at her. The male officer motioned for her to have a seat on the bed next to her brother, which she quickly obeyed. The male officer began rummaging through the bathroom, while the two female cops began questioning the two siblings. "How old are you, miss?" Erika asked. "Eighteen," she whispered quietly. "Is this your boyfriend?" said the Hispanic cop. "This guy taking you to prom tonight?" "He's my brother," she replied quickly. The two cops looked at each other, slightly smiling in amusement. Before Tommy could ask what the joke was, the male cop lumbered out of the bathroom, carrying the bottles of alcohol in his hands. "Well, your brother is gonna spend the night in lock-up tonight, sweetheart," he said threateningly. "Providing alcohol to a minor is pretty serious around here." "I can smell it on your breath from here," Erika hissed. "You know what they do to boys like him in county?" laughed the Hispanic cop. "I hope you didn't have any big plans for tonight, 'cause you guys have fucked up!" Panicking, Tommy stood up pleadingly. "Hey, I'm sorry, I...." "Sit down," roared the male cop. "Don't make me have to use my stick on your ass!" Tommy slowly sat, nervously tucking his hands under his armpits. Carrie's lip was quivering in fear, and she was already sweating in her prom dress. Erika took her hat and glasses off, revealing a long sweeping mane of jet black hair. Tommy would have been turned on if he wasn't so terrified....even Carrie would have admitted that she was the most striking woman she had ever seen. "We see this every prom night," Erika said. "Kids breaking the rules, getting into trouble.....and when you get busted, your lives are never the same. It's a real shame." Carrie, unable to take it anymore, finally started talking. "Look, I promise I will never, never do this again! I don't want my brother to go to jail, my parents would never forgive him! It's my fault, I'm the one that begged him to buy the beer, okay?" "Sis, it's alright, I'm the one who...." "I think they deserve a chance to make this right," said Erika unexpectedly. Carrie and Tommy looked at each other in amazement, and back at the cops in confusion. "Ivan? Janie? What do you think?" "There were seven bottles in there," said Ivan, the male cop. "We could charge her with seven counts of underage drinking." "She should perform seven tests to fix this," suggested Janie. Tests? What were they talking about? "I'm going to give you a choice, young lady," Erika decided. "What's your name?" "Carrie," she replied. "What's your name, stud?" she directed towards her brother. "Tommy," he offered, not looking the woman in the eyes. "Carrie, I am going to give you seven tasks to perform. You will perform every task without argument. Your brother will also obey everything that I decide without argument. If you perform all seven tasks that I give you to my satisfaction, without any trouble from either you or your brother, we will forget that we ever saw you and your parents will never have to find out about this little episode. Do you agree to my terms?" "Hey, this is my sister," Tommy protested. "You can't do this, are you planning to have her get naked or something?" Erika laughed, and she reached down and began casually massaging his cock! "Tommy, I think you know where this is leading. And yes, you or your sister can say no. But would you rather a few minutes of paying for your crimes.....or a few years?" Carrie couldn't watch her brother getting stroked by some crazy woman, it was sickening! But Tommy stopped protesting, and Carrie quietly nodded in agreement. "Officer Janie," Erika said thoughtfully. "Go to the car and get the fun bag." "Yes, ma'am," she nodded, walking towards the hotel room door. "Tommy, strip down to your underwear. We're going to handcuff you during this first task." "In front of my sister?!" he shouted angrily. It caused the three officers to stop, and stare at the young man. Immediately, he knew he had made a mistake. Erika glared at him intensely for a full minute, without speaking. "This will be your first and last warning," she finally said in that quiet, intense voice. "If you disobey anything I request of you, the deal is off. You go to jail, your sister goes to jail, and your parents will be notified. Now take your fucking clothes off, you little shit-stain." Tommy quickly glanced at his sister, who returned his gaze with a pleading look. Neither one of them wanted to get busted....so Tommy finally decided to stop arguing, and began peeling off his clothes as Carrie shamefully looked away. Officer Janie, pleased with this, left the hotel room. Once Tommy had shed his clothes, Erika took out her handcuffs and locked his hands behind his back. Next, she guided the young man to lie face down next to her on the bed. "Now, the real games can begin," Erika smiled, stroking Tommy's back with a surprisingly gentle touch. "Do you have a good view of your sister, Tommy?" He nodded slowly. He was standing just a few feet in front of him, next to officer Ivan, but he couldn't look at her. He was nearly naked in front of his little sister, this was humiliating!.....but he had no idea how degrading this night was going to become. "Carrie, get on your knees, and place your hands behind your back," Erika said pointedly. "Right there on the floor, in front of Officer Ivan." Carrie took a deep breath and knelt, knowing where this was going. "You have seven tasks to perform if you and your brother want to stay out of jail. For your first task, I want to see you give my friend Officer Ivan the best blowjob of his life. You are not to use your hands, do you understand?" It wasn't the idea of going down on this cop that bothered her, she'd been doing that to boys for quite some time now. It was the idea of doing it in front of her brother that creeped her out. "For how long?" Ivan responded by giving Carrie a light, but harsh slap across the face. "For how long, Mistress Erika," he corrected her. Carrie bit her bottom lip, trying to adjust to the rules. "For how long, Mistress Erika?" Erika smiled, happy with how the night was turning out. "You can stop as soon as the last drop of Master Ivan's cum drips down your throat. Let's go....get sucking." Carrie's purple prom dress suddenly felt tight and constraining on her as she knelt in front of Ivan. She was torn.....she wanted to take off her dress, so as not to spill a mouthful of cum all over the fabric. On the other, she didn't want to show off her body if she didn't have to. Ivan was unzipping his pants now, so Carrie took a deep breath and decided to just be extremely careful. What was soon dangling in front of the teen-ager made her gasp unexpectedly. When Ivan's pants fell to the ground, it revealed the largest cock Carrie had ever seen....and it was only half-erect! It was longer than the quarterbacks cock, and thicker than her science teacher's package. It was a weapon, she realized. A dangerous weapon. "I'm waiting," Ivan urged her, impatiently. Carrie nodded apologetically, not realizing that she was just kneeling there, marveling at it in quiet terror. She edged her face forward and pressed the velvety tip of Ivan's cock against her top lip. Instinctively, she began to wrap her fingers around the base of Ivan's prick, trying to feel the thickness in her hand. This experiment was cut short when he flicked her left ear with his fingertips. "Ahhhhh, fuck!" she yelped, rearing her head back. "No fingers," Erika reminded her. "Now....proceed. This task doesn't end until you make my friend explode......and you still have six more fun little tasks after that...." Carrie opened her mouth a little wider now, and locked her fingers behind her back----she didn't want to feel something worse than a flick on the earlobes. By this point, Ivan was completely hard....and sporting a massive piece of wood that seemed to be as large as her wrist! It felt hot as she pressed it against her tongue, as although she wouldn't admit it out loud, extremely delicious. Erika watched in approval, as she started running her hands up and down Tommy's back and ass. Lying face down, he was facing his sister, but Erika noticed that he was closing his eyes. Disapproving, she smacked his ass with a painful, open-palmed slap that filled the room with an echo. "You have to watch," Erika insisted. "Watch your sister give my friend head, Tommy. You have to follow the rules, too." "Okay," he muttered. Erika responded with another smack, this time on the back of his thighs. "Okay, what?" "Okay, Mistress," he quickly amended. "Much better," she smiled. "Carrie, get back to it. I want to see that shaft in your throat." Carrie sadly moaned, and tried to get more than five inches past her lips. Her heart wasn't into it-----this was so humiliating!-----and her poor brother was being forced to watch this man violate her mouth! Then it occurred to her-----how much more painful would it be to have this giant fucking her? What if he was cruel enough to stuff it in her pussy....or worse yet, her ass?! True, she was ready to let her boyfriend take her black cherry tonight, but this man would destroy her! But....if she could get him off right now, she wouldn't have to worry about it, would she? Just make this man cum hard, and he'd probably be done for the night! Spurred on by this sudden revelation, something wild in Carrie broke loose. She began moaning like a porn star, and she started rocking her head back and forth. True, she could only get about seven inches into her mouth, but Ivan seemed to be enjoying it. It wasn't a few minutes later that she felt his hands slide through her hair, firmly clutching her head, and he began guiding the rhythm of her blowjob. As she couldn't use her hands, and he wasn't allowing her to rest, Carrie became aware of a steady stream of drool had begun cascading down her chin. Her collarbone was getting soaked as her first task continued, and so was her expensive prom dress. It just occurred to her that if she wanted to keep from ruining her dress, she was going to have to swallow every drop. ....and from the size of the large, heavy ball sack bouncing in front of her, she had a feeling that Ivan had a lot stored up. Over on the bed, Mistress Erika reached underneath her captive's body to massage Tommy's cock. The unexpected groping caused Tommy to jump suddenly, but with his hands cuffed behind his back and Erika's other hand firmly pressing down on his ass, he had little room to move. "Ooooh, Tommy...you're a little deviant," laughed Erika. "I can't believe you'd get so hard watching your sister sucking a big, juicy cock." At this point, Janie re-entered the room, carrying a large duffelbag full of unidentified objects. "Did I miss much?" she asked gleefully. "We're about to move on to the second task," Ivan said breathlessly, as his hands began moving Carrie's head even faster up and down his shaft. "Cool, I can't wait for the second task," grinned Janie. She knelt behind Carrie and pulled a second pair of handcuffs from the duffelbag, and quickly locked Carrie's wrists together behind her back. "Is that totally necessary," Carrie asked daringly, as she allowed Ivan's cock to slip from between her soaked lips. Janie responded by clutching Carrie's breasts and squeezing painfully! "Bitch, I don't want to hear you talking back to us," the Hispanic cop hissed into her ear. She slipped her fingers into the front of her gown, found one of her nipples, and pinched until Carrie screamed for mercy. "Janie, hold this little whore's head still, I'm gonna cum," Ivan shouted. Carrie tried to protest, still aching from the mistreatment of her nipples, but as soon as she opened her mouth, Ivan was ramming his cock deep into her throat! She was handcuffed, Janie was putting pressure on her legs by kneeling across them, while holding her head steady....there was nothing she could do! For thirty seconds—-it seemed longer-----Ivan pounded his cock so hard that his stomach pressed against her nose, and she could feel the tip of his cock touch the back of her throat. Happily, it didn't last much longer than that....and she could feel his first powerful jolt of hot cum fire straight down her throat-----it barely touched her tongue. She held her breath, preparing to swallow the entire load, but Ivan had other plans. He pulled out of her mouth, screaming blissfully, and wrapped both hands around his cock and fired the rest of it himself. With Janie holding her head still, she was helpless to resist the cumbath she was being subjected to. All she could do was close her eyes and mouth and wait for it to end. By the time Ivan's monstrous cock had finally finished pulsing, Carrie could feel warm, sticky fluids splattered across her cheek, in her hair, and across her neck. Worst of all, the front of the gown had taken a few spots as well.....and she knew that getting it cleaned up wasn't these maniacs top priority. Seven Tasks of Poor Carrie But at least, she realized, she had taken care of Ivan without having to feel him stretch her apart. And somehow, inexplicably, she felt a small hint of pride and accomplishment at hearing Mistress Erika applaud her efforts. "Well done, well done....you have finished your first task." "Thank you, mistress," she nodded, trying to lick Ivan's cum away from her bottom lip. With her wrists cuffed, she could only kneel there, feeling filthy. "Can someone wipe me off, please?" Ivan approached her again, and Carrie was amazed to see that his hands were literally dripping with dangling curtains of cum-----she thought that as much had splashed over her face, there wouldn't have been a drop left on his fingers! "Our little slave wants us to wipe her off," he laughed. "Janie, do you have a towel?" "I think there's one in the bathroom," Janie suggested. Ivan shrugged dismissively, and proceeded to run his cum-covered hands over Janie's face, through her hair, and over her shoulders until they were clean again. "That's okay, Janie, I found something better to use." Carrie scowled angrily, but dared not say anything more. "Well Ivan, I think you've earned a rest," Erika said. "Janie, why don't you get comfortable on the other bed.....it's time you had some fun, sweetie." "About fucking time," Janie grins, and Tommy watched in excitement as the short Hispanic cop took off her slacks, revealing a hairy snatch just begging to be licked. Tommy's cock twitched in Erika's hands, as his mouth began watering at the thought of being thought of being forced to go down on Janie, just like his sister had to go down on Ivan. Erika began laughing----something told Tommy that it wasn't going to be that simple. "Guys, our little slave boy is getting stiff.....he thinks he's actually going to be lucky enough to lick Janie's pussy." The other cops laughed, and Tommy's heart sank as Ivan handed Erika a large bottle of strawberry lubricant, and a few other items that he couldn't make out.. "Get up on your knees Tommy," she commanded. "Face down, ass up in the air." Tommy resisted for a second, shaking his head, but he was treated to three sharp spanks and a painful sensation on his inner thigh! This evil bitch had clipped a clothes pin to his skin! "You remember the rules, Tommy, you have to obey or you get punished....or worse yet, the deal is off and you two go to jail. Now get on your FUCKING KNEES!!" There was no more argument. Tommy obeyed, and choked back fearful tears as his underwear was ripped off of his body. He was exposed now, his stiff cock dangling below him....and his asshole vulnerable to anything that Erika wished to do to him. With his wrists handcuffed, he could barely move, let alone see what Erika was holding beside the lube and clothespins. Tommy heard a moan now, and it was coming from Janie. He slowly twisted his head to see the cop, expecting to find her fingering herself. Instead, he was shocked to find his little sister on her knees once again, by the bed, with her hair stuffed tightly between Janie's legs. His baby sister was going down on another woman! They must have guided her over while he was arguing with Erika. "Isn't that sexy, Tommy," Erika asked soflty. "Your little sister is licking my friend's pussy. I'll bet it's making her wet......I wonder if she's ever had her tongue is someone's cunt before." Tommy turned his head away, feeling too ashamed to watch his sister forced to perform such a degrading act. That's when he felt a second clothespin being attached to the skin of his balls! "This is a performance, Tommy,'" Erika said softly, but sternly. "You have to watch, or I make things tough for you!" Tommy turned back to see his sister's head bobbing up and down, each bob causing Janie to squeal pleasurably. He was ashamed to realize that his cock was getting stiffer....and even more ashamed to realize that he wished he had a better view. He closed his eyes, barely able to watch. "Eyes open," Erika reminded him, flicking the clothespin on his balls. He obeyed, and then was shocked to feel a warm gush of liquid drip over his ass. It felt like gel----obviously the lubricant-----and Erika had poured on far more than was probably necessary. It coated his asshole, cascaded down his balls and cock and onto his heels. What was she going to do? From the corner of the room, Ivan answered his question. He hopes that it wasn't going to involve him! "This is your second task, Carrie," Ivan smiled, stroking his cock as he spoke from his chair. Was it actually getting hard again? "You need to make my friend cum......" "And the longer she takes," Erika chimed in, "the more playtime I get with you." Erika's finger began circling Tommy's asshole now----and with his anus covered in lube, the only resistance was Tommy's own fear. Over by the other bed, Carrie felt degraded, embarrassed and filthy. She could still feel what felt like an entire quart of Ivan's cum covering her face and hair, and now she was having her face pressed against this woman's clit! It tasted salty and sweet at the same time------not at all what she thought a pussy would taste like. She didn't hold back----the quicker she completed her tasks, the faster they would get out of here----but she was only two tasks in, and she was already exhausted emotionally. She lifted her head back for just a moment, taking in a deep breath before continuing, when she head Tommy grunt with a hoarse voice. "Oh Carrie, you'd better hurry and get that pussy to scream," laughed Erika. "I already have two fingers in your brother's tight little ass....I'm not sure how much more he can take!" Concerned for her brother, Carrie shoved her face tightly into the dripping wet cunt that sat in front of her. Imitating what the football coach did to make her cum last year, Carrie began stroking the inside of Janie's pussy lips with the tip of her tongue, while using her fingers to vigorously stroke the cop's clit. The results were almost instantaneous-----Janie began writhing, moaning, and reaching up under her shirt to massage her own nipples. It wouldn't be long. Tommy couldn't believe what he was seeing, but he was too paralyzed with sensations he'd never known before. Amazingly, he felt his asshole stretch open even tighter as Erika slid a THIRD finger into him. "Don't worry baby.....I don't think she has much longer there," Erika commented. "Carrie, if you don't make her cum soon, I'm gonna have my entire fist in your brother's tight little ass...." Carrie stroked Janie's clit even faster, kept rubbing her tongue across her slit, and even managed to stroke Janie's soaked ass with her thumb. After a few seconds, Janie howled at the top of her lungs.....and a thick, powerful jet of liquid began unexpectedly firing from her pulsing pussy! Without any way to balance herself or sit up, the shackled Carrie could do nothing except feel her hair, mouth and gown get covered with the cop's juices...... She had just made another woman squirt! As Janie collapsed in astonishment, Tommy could only marvel at what he had just seen. He barely felt Erika's fingers slowly slide out of his ass. He realized that she had pulled out only when she began clapping in approval. "Bravo, Carrie, bravo," she smiled. "You're making me proud. But I think Ivan is back to full strength......let's move right on to our third task!" Carrie looked in dismay at Ivan, who was standing up again, grinning. He was hard again------harder than before, actually! "Are you ready to have a big cock in your mouth again, Carrie?" Erika asked. "Are you ready for your third task?" "Yes, mistress," Carrie responded quietly. Her jaw was already aching from sucking off Ivan a few moments before......how could it get any worse? "Flip over, Tommy," Erika ordered, as she thankfully removed the clothespins from his body. "Get on your back." Confused, Tommy did as he was ordered. Still handcuffed, he found it difficult to roll over as they asked, but he eventually succeeded. Smeared with lube, and his ass still pulsing from Erika's fingers, he was happy to at least be on his back, where his ass was protected from Erika. But his cock was standing at full attention, in full view of his sister. Janie and Ivan had uncuffed Carrie at this point, and pulled off her cum-covered prom dress, as well as her bra and panties. She was completely naked now, and she used her free hands to try to cover herself. Erika leaned forward and gently pinched both of Carrie's hard little nipples, pulling her towards the bed, and towards her brother. She didn't like where this was going. "We're going to give you a chance to make things a little easier on you and your brother," Erika explained. "Straddle your big brother......straddle him like you were going to have a nasty little 69!" "God, no!" she protested in shock! This was exactly what she was afraid of hearing, but Mistress Erika wasn't in the mood to hear any complaints. She pinched her nipples once again, twisting, and smiling cruelly as Carrie's body jolted in pain. "You don't want the handcuffs back on, do you?" Erika threatened, her voice getting louder as she barked. "If I have to put the handcuffs back on you, we're taking you to jail next. Sit your dirty little cunt in your brothers' face, lean down, and suck his cock!" Carrie started to cry, but it only seemed to amuse the cops even more. Trying not to make it worse than it already way, she straddled her brother's face, trying not to smother him by touching her pussy to his skin. She had to stand on the tips of her toes to keep her weight off of his face, which took all the muscles that she had in her legs. As soon as she wrapped her fingers tentatively around her brothers' dick, she felt pressure from behind her.......Ivan's thick, monstrous cock was pressing against her twat! He was going to fuck her, right over her brothers' face! She looked at Erika in horror, but she was only laughing with delight. Her pants were off now, and she was fingering her own shaved, glistening wet slit. Janie, now completely naked as well, got on the bed with Tommy and Carrie, rubbing her own nipples in excitement. She was holding a riding crop in her hand, and the sight of it frightened Carrie. She had no tolerance for pain, and she didn't want to feel it on her ass. "Here's the challenge," Erika said. "You have to suck off your brother, while Ivan fucks you. If you can make Ivan cum first, we'll skip your fourth task, and you'll be that much closer to going home. But if Tommy cums first, your fourth task is going to be really, really uncomfortable." No sooner than she said the words, she could feel Ivan's cock pressing into her! It was bigger than anything she had ever stuffed into her pussy, and she couldn't help but grunt in shock. Tommy's cock was quivering in front of her, and she tried to work up the courage to place it in her mouth. Of course, if Tommy didn't cum, they would skip the fourth task, so she briefly considered not giving her best effort. But then she found out what the riding crop was for, as it smacked her right ass cheek with a cruel crack. "I want to see a nice, slobbery blowjob," Janie insisted. "If I think you're holding out, I'll paint your ass red, girl." The left cheek was smacked now.....followed by her lower back........and then the right ass cheek again.....and Carrie finally submitted by deep-throating all six inches of her big brothers' cock. The riding crop ceased, and Tommy's body twitched uncontrollably. Carrie just sat there for a moment, trying to get used to the situation she was in. She held her brother's cock firmly in her mouth, the tip of it pressed tightly against the roof of her mouth, although she made no other movement. Ivan's cock was slowly edging deeper into her pussy, stretching her out.....she was being filled at both ends, and the sensory overload just shut her down for a moment. She was smacked again on the lower back, causing her to jerk. "Suck him, don't just hold his dick in your mouth like a dead hooker!" screamed Janie. And with that, she began earnestly blowing her brother's cock, pretending like it was her boyfriends. She used both hands on the shaft, and sucked vigorously....she knew that Tommy would probably explode before Ivan did, but she'd do anything to stay out of jail----or having that Hispanic bitch smack her again! The faster Carrie's lips glided over her brothers' cock, the faster Ivan's hips seemed to be bucking. Standing behind her, his fingers tightly gripped around Carrie's hips, he was slamming his cock unrelenting deep into her, causing her entire body to quake. It forced her mound to press against her brother's face, and she could feel her own juices dripping into his nose and mouth. She could only imagine what he was thinking right now, but she tried to put it out of her head. She tried not to think about her stiff nipples pressed against his chest, or how his cock was trembling in her mouth. Or worse......how close she was to cumming in front of all of them! Tommy was in agony, as he tried to hold back----but his senses had been overloaded by this point. He had watched his little sister suck off not only a huge cop, but another woman----and Erika had been teasing him the entire time. He didn't think it was going to be possible to not shoot a load in his sisters' mouth before Ivan was finished......he had already shot a wad, and Tommy was just too worked up. He had hoped that Carrie would hold back a bit, but every time she slowed down, that fucking Hispanic cop would smack her ass with the riding crop! So he did his best to think about anything else------anything--------he had no idea how good his cock would feel all the way in the back of his sister's throat.....he was twisting his hips, trying to pop his cock out of Carrie's mouth for just one moment..... Janie saw what she was doing, and she held Carrie's head down------Tommy's cock was completely stuffed down his sisters' throat now, and her sweaty clit was pressed against his nose! He could feel Ivan's balls slapping against his forehead, and he tried to focus on that to keep him from exploding, but it wasn't enough. Not nearly enough. An entire week's worth of his sperm exploded out like a volcano, as the other cops cheered-----he could feel his sister's mouth gulping and sucking and swallowing, as she was forced to swallow every ounce. After a long, ecstacy filled minute, she had sucked him completely dry, swallowing almost every drop. They had clearly failed the challenge, and Ivan celebrated by pulling his long cock out and cumming a second time! From the corner of his eye, Tommy could see Janie screaming with joy, using her hands to pump him off. He closed his eyes as wave after wave of cum coated Carrie's ass and cunt, as well as Tommy's forehead! Exhausted, Carrie sat back without thinking, smearing more cum all over Tommy's face. When the cops pulled her off of his body, Carrie had long streams of Tommy's jizz dripping from her mouth, and what seemed like a gallon of it raining off of her ass. She looked as if she had been beaten, and she sat in shock at the edge of the bed. How much more could they take, Tommy wondered? Would his sister ever be the same after this? He wished he could wipe his face off, the thought of Ivan's cum all over his face was repulsive, but he was still handcuffed. He looked at Carrie. She looked different now. Defiant, almost. "Do you have something to say, little girl?" Janie asked, stroking Carrie's cheek with the riding crop. "Are you going to cry now?" "Is that all you got?" Carrie spat back. "Who do I get to fuck next?!" The cops looked at each other and laughed. They seemed impressed, but Tommy wasn't sure it was a good idea to adopt such a confrontational stance. But it might have been the only thing keeping Carrie sane. "Both of you.....get on the bed, side by side," Erika ordered. "Get on your knees, face down into the bed.....I want your asses in the air!" Tommy and Carrie did as they were told, although they could barely look at each other. By now, they both reeked of sweat and semen, and they had no idea what was going to happen next. At the edge of the bed, they could both see Ivan leaning back in the chair in the corner of the room. His balls had been emptied twice and his cock dangled between his legs lifelessly, but he was slowly massaging his shaft, trying to bring it back to life. Janie kneeled next to both of the kids, and she began tenderly licking Tommy's face for a moment, and then Carrie's, cleaning them off with her tongue. From behind them, Erika was applying another handful of lube to both of their asses, and Tommy could hear the whirring noise of small vibrators. Erika had two in her hands, and she was preparing to use both of them. Her fingers were one thing....but he wasn't sure he was ready for this. "Oh yeah, bring it on," his sister was laughing. "Oh, that I will," promised Erika. "This is your fourth task.....make Ivan hard again. When he gets hard, we'll go on to your fifth task. Until then, you're both my bitches!" And with that, Tommy felt the thin vibrator slide into his ass! He tried to squirm free, but because he was on his knees and he was still handcuffed, he couldn't move. Worse yet, his asshole was completely opened to Erika because of his position. She wasted no time in gliding the vibrator deep into his ass, and she started stroking it in and out...... "Look at that," Erika snickered. "I think Tommy likes it up the ass....his dick is getting stiff again!" Tommy didn't think it was possible, but his cock was definitely twitching. How could that be? Janie was pulling more toys from her bag now. Janie had pulled out something Tommy had never seen before. It was a rubber object----shiny, black and thick. Tommy didn't know what it was....but it didn't look comfortable. "Come on, I thought you guys were going to get serious here," laughed Carrie. "Why are you holding back?" What was Carrie doing? She was actually egging them on! "Sis, shut up, will you?" Janie ignored her, and wandered behind Carrie and turned on the vibrator. "We're going to need your brother nice and stiff for this next task, honey," Janie explained. "We still have him all handcuffed, why don't you reach over and start fluffing him." Before Tommy could protest, Carrie did as she was told, and once again he felt the bizarre sensation of his sister's fingers stroking his cock! After a moment, she gripped his shaft rather uncomfortably, as she felt an entirely new sensation. Suddenly, she was twitching and gasping for air. "No...." she sqeaked almost voicelessly. Her defiant attitude had slipped away as Janie began forcing the butt plug past the teen-ager's tight little sphincter. "I told you it was going to be uncomfortable, you smart-mouthed little cunt," Erika hissed, as she continued gently sliding her dildo into Tommy's ass. "Are you going to behave like a good girl now?" Carrie didn't answer-----she only gasped in short panicked breaths. She finally responded with a tearful yes when Erika smacked her ass with the back of her hand, adding yet another welt to her backside. Tommy felt the vibrator slip out of his ass now, and he wondered why Erika had stopped. Then he realized that the fourth task had ended, and it was time to move on to the fifth task----because Ivan was on his feet now, fully hard, ready to punish his sister again, he assumed. He hoped. As much as he hated himself for thinking it, he'd rather have Ivan's cock in Carrie's ass, and not his. Erika leaned in by Tommy's ear and started whispering. "Tell me something, young Tommy," she asked. "Have you ever had another man's cock in your ass?" Seven Tasks of Poor Carrie Tommy nearly threw up at the question. He quickly admitted that he had not. "Would you like another man's cock in your ass?" "Please, no......I'm not gay," Tommy pleaded. "Neither is Ivan, but he does what I ask," Erika explained. She was silent for a moment, as Tommy thought about what was going to happen next. At last, she continued. "I'll make you a promise. I'm going to take off your handcuffs, so you can better help us finish completing your sisters' tasks. I know you probably want to wipe off all that nasty cum off your face and body, but I like it where it is. If you don't clean yourself up, no matter what happens after this, I promise you won't have to suck or fuck Ivan at all. Is that agreed?" Tommy quickly agreed, and they uncuffed him. It took a lot of strength to resist the urge to wipe the drying sperm from his face, but the alternative was even scarier. "Carrie, you stay right where you are," Erika demanded. Tommy snuck a glance at his sister......lying naked on the bed, with her ass up in the air and a thick black butt plug tightly wedged in her ass. The spark of defiance she had shown a few moments ago was all gone. The other women got on the bed next to Carrie, sandwiching her. Everyone in the room was naked now, and the sight of his sister and two other women lying across the bed----naked, with their asses up in the air-----actually made his sore cock grow another inch. "This is the fucking and sucking contest" Erika explained, as she rubbed her fingers over Carrie's ass, gently tapping the butt plug for effect. "Ivan, please get behind Janie and put that cock to good use." Ivan did as he was told, and Janie squealed happily to feel Ivan's cock penetrate her. "Tommy, you stand in front of me......you're going to fuck my mouth...and I want to feel every inch of you in my throat." Sounded good so far, Tommy thought. Carrie laid there, still trying to adjust to the butt plug. It wasn't helping that Erika kept tapping on it. "Every sixty seconds, you and Ivan will rotate around, switching holes. If Tommy can cum first, I'll let you take a shower and you'll get to sit out of the rest of the night's festivities. If Ivan cums first, then Tommy has to clean us girls up! So....let's get started!" And so it began, and Tommy had every reason to not hold back now. He put both hands on Erika's head and began pumping wildly. He didn't want to hold back, not for this vicious, cruel bitch! He wanted to make the woman cry for mercy, but it wasn't happening. She seemed to have total control over her gag reflex, and it she seemed to love the rough treatment. Even worse, Tommy wasn't sure if he could bust another nut so soon. Could he cum again sooner than Ivan, who had already shot twice? It wasn't but a minute later that Erika raised her hand, pointing towards her rear end. It was time to switch, and Tommy and Ivan moved counterclockwise around the women. Tommy was behind Erika now, and Ivan had already gotten around to Janie's mouth-----the little Hispanic cop didn't seem like her mouth was wide enough to fit Ivan's cock past her lips, but somehow, she did it. This was a race to see who could shoot first, so there wasn't any time to waste. Tommy maneuvered himself, parting the dripping folds of Erika's glistening cunt, and shoved himself inside. She must have had thigh muscles of steel----they clenched at his cock tighter than a fist! Soon, he had forgotten all about the hardening sperm in his hair and face, and focused on fucking the shit out of this dominatrix.....and the line of pussies that would follow. Tommy snuck a glance at his sister, kneeling there with her ass up in the air, with a thick rubber plug locked into her ass. If he didn't shoot inside Erika in the next few seconds, they were going to expect him to fuck his sister! If he could only.... "Switch," commanded Erika! Tommy moved without thinking, pulling his cock from her swollen, dripping hole. He stepped over, trying to forget that this tight little pussy belonged to his baby sister, and shoved himself all the way inside. Carrie gasped, a mix of agony and ecstacy, as her brother's cock filled her, and his stomach began jostling her butt plug. She could only groan for a second-----right now, her mouth belonged to Ivan, and he was stretching her jaw to the limit with his monstrous dick. Tommy fucked his sister wildly, while trying not to cum. He didn't want to shoot off in his sister, but he wanted to cum before Ivan.......the entire situation was driving him insane. If he could just hold out for a few more..... "Switch," Erika announced again. Carrie exhaled deeply and coughed a little as both Ivan and her brother's cocks left her....and Tommy couldn't help but find himself even more aroused as she drooled on her wrists while trying to catch her breath. Ivan was getting a vigorous blow-job from Erika now. Tommy could tell that Erika was trying to make Tommy lose.....and Tommy definitely wanted to win. Tommy decided to be daring, and take a chance. He stood behind Janie, who was wiggling her ass wildly, waiting for Tommy to start fucking her. She was fingering her own clit in anticipation..... Tommy just had to beat Ivan......and Janie's left hand was busy playing with herself. With one hand, Tommy gripped Janie's free right hand. With his other, he grabbed a handful of her hair and gently but firmly pulled backwards, all but locking her into position. As she groaned-----either in protest or excitement, although Tommy barely cared at this point-----he pressed his cock quickly past her tight little asshole, sliding in all the way to his balls. "What the fuck are you doing, boy?" she screamed. Erika, between slurps on Ivan's cock, just giggled. "Calm down, Janie, I never said which hole he could have, did I?" "Fuck you, Erika," Janie spat back, and although she tried to sound angry, a hint of laughter was in her voice. It was all Tommy needed to hear, and he began pounding Janie's ass as hard as he's ever fucked a girl. He was going to fill this woman's ass, he knew it.....it was just going to take a few more pounds.... And just as his balls started to explode, he was disheartened to see Ivan already cuming again! Thanks to Erika's hands, Ivan couldn't hold back.....one blast of cum fired over Erika's head, but the rest of it------there must have been another gallon!-----went right into Erika's mouth, and she seemed to swallow his load like a hungry animal. And as she gobbled Ivan's cock, Tommy came too----filling Janie's ass right to the rim. He lost the challenge again, but at least he got to have his way with one of these fucking cops. Tommy pulled out of her, his cock completely milked by this Hispanic woman's ass. Janie collapsed on the bed, lost in her own orgasm, as her fingers finished herself off. It was about the hottest fuck Tommy had ever had, but his cock was now getting terribly sore. The sixth task was starting now, and it looked like Janie wanted some payback. "Hands behind your back, you smart-ass," Janie commanded. She was doing all of the talking now, while Erika was still using her tongue to take in the last drops of cum dangling from Ivan's cock. Tommy was confused. "Aren't I supposed to clean you up now?" "Absolutely," Janie nodded, handcuffing Tommy's hands behind his back once again. "How can I wash you if my hands are cuffed," he asked. Janie answered by grabbing the skin of his testicles and pinching.....Tommy yelped angrily. He tried to step backwards, but Ivan----his cock having been fully emptied into Erika's mouth-----was now holding him in place. "We were going to make it easier on you, but since you decided it'd be funny to fuck my ass without warning me, you'll have to do it the hard way now. Ivan, put him on his back.....he has to clean up Mistress Erika first." Tommy couldn't fight the larger cop as he literally picked him up and tossed him face-up on the other bed. Then, Ivan sat down next to Carrie, who was still struggling to get used to the butt plug buried uncomfortably in her ass. Janie was straddling Tommy's chest now, and he could feel her dripping pussy and cum-soaked ass sliding over his stomach, while her knees pinned his arms down. He couldn't move, and Erika was approaching him with a sinister grin on her face. Why wasn't she talking? "Ivan made a mess of my friends' mouth," Janie explained. "Time to clean her up......clean her up completely!" Erika kneeled over and kissed Tommy, and her tongue easily parted his lips and forced its way onto his tongue. It was then he realized that it wasn't just her tongue that he was feeling. Something....foreign. Tommy realized with horror that Erika hadn't swallowed! Every hot drop of cum that Ivan had poured into her mouth was being dumped into his! He tried to jerk free, but it was impossible. Between the handcuffs and the two women holding him down, he wasn't going anywhere. "Swallow or drown, motherfucker," Janie laughed. He had no choice.....and against every instinct he had, he swallowed every ounce Erika gave him in that terrible kiss. Erika stood up now, and Tommy realized in horror that she was wearing a strap-on cock, nearly as large as Ivan's! "We were going to make this easy on you, but that was before you ass-raped my friend," Erika explained. "So here's the sixth task......take a look at your sister....." Fear was starting to overtake him now! Tommy glanced at his sister.....she was lying on the other bed on her back, while Ivan laid next to her, fingerfucking her. He had three fingers inside of her, thrusting in and out, while he used the other hand to keep the butt plug from esacaping. Carrie was breathing quickly, as this man banged her mercilessly. She looked to her brother in panic, but he was otherwise occupied. "Here's what's going to happen, Tommy," Erika continued, as she poured a generous amount of lube on her strap-on, and coated the entire shaft with her fist. "Janie's going to sit on your face now. You stuffed her ass and emptied your load, and that's what you're going to have to clean. Every single drop, boy, you need to lick her clean. And since you got the fun of some ass fucking, you'll have to be on the receiving end now. I'm going to fuck your little virgin ass, Tommy-----and that's the sixth task. As soon as Ivan can get his whole fist up your sister's tiny fuck-hole, this task ends....and we'll move on to the last task. Do you understand?" Tommy was about to answer, but Janie was already pressing her pungent ass against his face, while she painfully pinched his nipples! It caused him to gasp----and as he did, his own cum began to waterfall from Janie's ass, and over his nose and mouth. "I don't feel your tongue, boy," Janie complained, pinching his nipples again. "Clean me up!" After that, Tommy was overloaded with so many conflicting sensations and tortures. The only time Janie wasn't painfully twisting his nipples was when Tommy explored her gaping asshole with his tongue. The deeper his tongue pressed in, he could taste the salty contents of his own balls dripping over his lips. Frightened by the taste, he withdrew his tongue and tried to turn his head away.....but that only resulted in Janie twisting his nipples. When that didn't force Tommy to return his tongue, Janie began flicking the tip of his exhausted cock.....and he quickly complied, stroking his tongue in and out of her ass, as Janie purred contently. Then, he felt his legs being lifted in the air.....this was going to be worst than having Erika's fingers inside him, he was certain! Perhaps she would be gentle? The tip of the rubber cock was pressing against his asshole, and he could feel himself trying to tighten up, hoping to prevent her from entering, but the lubricant was making him so slippery. Just as he wondered why the hell his cock was getting stiff from this treatment, he was penetrated! Erika laughed cruelly, triumphantly even, as she started to press the thick dildo into Tommy's defeated anus. Her hands were busy keeping his legs hoisted into the air, but her hips were doing all of the work. Slowly, she pressed forward.....inch by inch, stuffing Tommy's ass with its first dildo. Tommy tried to grunt, but his tongue was stuffed too far up Janie's ass to make a sound. "Are you clean, Janie?" asked Erika, once she had fully inserted her strap-on in Tommy's ass. "I think so, Erika, I think he completely cleaned me out," replied her friend. "Good, I think you can get off of him now, just hold down his shoulders," Erika requested. "I want to see Tommy Boy's face....." Janie did as she was asked, dragging her cum-slickened ass over his face as she dismounted. Janie knelt on the bed behind Tommy, putting her weight on his shoulders. He saw on the other bed his sister, now breathing rapidly, as Ivan had clearly shoved four fingers into her pussy, while using his other hand to quickly stimulate her clit. He couldn't tell if she was in pain or pleasure, but she was clearly not fighting anymore. Erika looked more terrifying than any of them----a wild look in her eyes, as she had buried herself all the way into Tommy's ass. He could barely feel anything now as she wasn't moving, just an overwhelming sensation of submission. Erika smiled at him, tightening her grip on his ankles as she kept them lifted in the air. "I want to see Tommy Boy's face as I fuck the shit out of him!" With that------like so many times that Tommy had done to other girls he had known and used------Erika fucked him. Not boned, not drilled......fucked. She pulled all the way out, and slammed back into him, with as much force and anger as Tommy had done to Janie a few moments ago. His ass was being assaulted and there was nothing he could do about it. He heard an agonized moan from the other bed, and he turned his head to see his sister-----she had Ivan's entire fist inside her pussy! "Oh," Janie pouted. "I was gonna get to ride his ass next!" Janie was wearing a strap-on now, too! She must have just now slid into it. "No, rules are rules," Erika announced. The giant dildo slid out of Tommy's ass, and his entire body quaked from the overwhelming sensations as he just lay there.....not even aware that his cock had once again become engorged. Ivan had carefully removed his fist from Carrie, and her pussy was now a gaping, pulsing wet hole. She barely fought back as Ivan picked her up off the bed with one hand and brought her towards Tommy and Erika. "You've done very well today, children," commended Erika. "Last task.....our little underage bitch gets all her holes stuffed. When you can make Ivan cum again, this is all over!" What happened next happened quickly. Before Carrie or her brother could contemplate what was happening, Ivan had dropped her on top of her brother. With the help of the female cops, they guided Tommy's cock into his sister's snatch----and with that, Carrie was once again being fucked by her brother. Ivan knelt behind her and slid his massive, inexhaustible cock into her ass! Carrie wailed as she continued to be punished by this double penetration, she couldn't believe that she had endured to much sinful behavior-----and she was especially astounded by how many times she had tasted and felt her own brother's cock. Her wails were cut short by Janie, who stood in front of her and forced her to deep throat the strap-on dildo she was wearing. Erika did the same thing to Tommy, and he nearly gagged at the realization of where that dildo had been just a few moments earlier. For fifteen agonizing minutes, Carrie was a fuck toy. Every hole filled, every trace of her innocent ripped away. Eventually, her entire body involuntarily spasmed into orgasm, and she felt the two men inside her doing the same....filling her once again with more sperm than could possibly fit. And with that, they were done. The cops quickly dressed, unlocked Tommy's handcuffs, and left the siblings emotionally broken and physically spent, lying next to each other in pools of sperm, vaginal juice and spit. "I love prom night," Erika laughed as they left. "It's amazing how much sex three friends with fake badges can bag in one night!" As she left the room, laughing cruelly, Carrie could only collapse into her brother's exhausted arms. She felt his cock stiffening again next to her wrist. She felt her own clit begin to tingle. Wordlessly, quietly, as she mounted her brother's cock one more time and began to slowly grind, she wondered if they would ever be the same again.....