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Catching Karen Ch. 01

By: baybabe36



The six eighteen year old teenage boys had cut class again and were hanging out on the steps of one of their homes, as usual. They were all seniors and about to graduate. They spent a lot of their time that way, smoking, and talking about girls or women that they knew or had seen. The boys were very close friends and shared everything. 

Over the past months, they had started a new hobby. This hobby was picking some girl or woman that they thought was attractive and planning on how to get what they wanted from her. They discussed classmates, neighbors, teachers, and even a few family members.

Half of the group had never had actual sex before and the half that had done that had limited experience. All were either eager to try it for the first time, or to try it again. The more the boys talked about it, the more it excited them. They went so far as to actually make plans, which included putting together a place to do what they wanted. 

The place they picked was an old abandoned warehouse that was down the street from their usual hangout. The building was condemned, very large, and had been a haven for homeless persons, until the local police ran them out. The homeless left behind an assortment of old bedding and odds and ends that the boys put to good use, making a place to take their imagined girl or woman.

They were talking, when they noticed a shiny black car park further down their street. The boys definitely noticed the woman that got out of the car, angrily talking on her cell phone. She was about five feet seven inches tall, had short blonde hair, and was about 35. 

They were amazed as the blonde started walking up the sidewalk, passing them without a glance, and continuing down the block. She was wearing a tight black dress, tan pantyhose, and a pair of shiny black high heels. 

All of the boys noticed the swaying of the woman's big hips and the way her tight dress highlighted her very full bottom.

Karen Hill's heels clicked on the sidewalk, as she continued her angry phone conversation. The mother of two did not notice the teenager walking up behind her. The boys had picked the most innocent looking one of them to go ask the attractive woman for some help, in order to get her off the sidewalk and into the warehouse at the end of the block.

The boy timed his approach to when the blonde was at the corner, then put on a sad face and spoke to her. Karen angrily glared at the youth, as he interrupted her phone conversation, until she noticed his age. The woman was normally very dominant and bitch, especially to her coworkers, but she actually ended the call to see what the boy wanted.

The teen explained that he could not find his little sister and asked Karen if she would help him. He asked her to come into the warehouse with him, to see if she was there, and to use her cell phone to call for help, if she was not. The woman considered for a moment, then said she would help him.

The other five boys had retrieved a bag from their house and had entered the warehouse, using a back door, while their friend was talking to the blonde. When the group heard the clicking of high heels coming around the corner and into the dark building, then got ready. The woman followed their friend through the open doorway, turned the corner, and was immediately attacked by the boys.

The teens had planned the capture many times and quickly had the blonde gagged with a strip of duct tape and her wrists tied together in front of her, using the same material. They then dragged her further into the warehouse, to the place where they had prepared an old mattress. Working as a group, then forced the struggling woman onto her back, then pulled her bound wrists above her head and used the duct tape to tie them to a metal pole, at the top of the mattress. 

They repeated this process with each of her ankles, to similar poles at the bottom

Karen thrashed and struggled helplessly, as the boys wasted no time pulling up the front hem of her dress and then cutting a hole in the crotch of her pantyhose and panties. The boys had already decided the order, so the first one just unzipped his pant, pulled out his erection, then laid down on top of their attractive captive. Karen's muffled scream filled the empty warehouse, as the boy atop her thrust his cock into her pussy.

The other five boys stood watching their friend start to rape the helpless blonde and they each pulled out their erections, eager to take their turn. Karen struggled against her bonds, as the teen's penis vigorously thrust in and out of her vagina. 

The boy humped away madly on top of the blonde, until he cried out and came violently in her buttery sheath. He was quickly replaced by the next boy in line, who took his place between the woman's long, widespread legs. The teen that had just finished went to the end of the line and waited for his next turn.

The second boy moaned and panted with lust, experiencing sex for the first time. He could not believe how good it felt to pump his cock in and out of the helpless woman's pussy. Karen continued to struggle beneath him, but was tied too securely to make him stop, and all she could do was scream into the tape gag, hoping someone would hear her. The boy cried out and came, then rolled off the woman. The third boy eagerly got on top of the blonde and was soon raping her forcefully.

Boy after boy got on top of the struggling, sobbing, screaming woman, until all six had taken a turn. When the last finished, the first boy was ready again, and was soon pumping away in the blonde's hairy pussy. He lasted much longer the second time, taking his time to enjoy the pleasure of the sex. When he had his orgasm, the teen was quickly replaced by one of his friends. This continued over and over again, as they gang raped their pretty captive.

Karen lay there sobbing quietly, as the last boy in line finally finished his second turn and then rolled off of her abused body. When she felt her wrists being untied from the metal pole, the woman hoped her ordeal was at an end. The teens untied her ankles, but then quickly rolled her onto her stomach, and retied her to the poles. 

When the blonde felt her full buttocks being spread and something slippery being spread over her exposed rectum, she realized what they intended to do to her next and she really began to thrash madly. Karen's muffled, high pitched shriek echoed in the open room, as the first boy forced his penis into her virgin asshole.

Catching Karen Ch. 02



Karen lay there helpless, trying to figure out how her normal afternoon turned into a nightmare. Working hard to become a successful real estate agent took up a lot of her time and she was driven to succeed. 

Karen often climbed the corporate ladder on the backs of other people's achievements, but she didn't care, as long as she got what she wanted. The blonde completely dominated her husband of ten years and was very strict and stern with her two sons. She was very abrupt, bitchy, and often downright mean to any coworkers who could not do anything the help her career. 

At the same time, she was very fawning and icky sweet to any boss that could help her move ahead. The woman had few friends who legitimately liked her, because of her 'better than everyone else' attitude, but she was not concerned in the least. All she wanted to do was to make money and gain prestige.

Karen would take absolutely any property listing, no matter the part of town, and prided herself that she could sell any listing, no matter how difficult. Consequently, that is why she happened to be on this particular block, this particular day. A male coworker had called her, concerned about her safety, and she had been ridiculing him on her cell phone, when she first walked by the group of boys. She now wished desperately that she had listened to him and not come alone.

Terry Smith was the leader of the boys, and they always deferred to his opinions. He dressed like a rocker, but actually came from a good home, in a better part of town, but had convinced his parents that since he was eighteen he could do what he wanted. His mother and father thought it was a phase and tried to give him the freedom he wanted. 

They would have been horrified if they realized he had planned and was taking the lead in the rape of the blonde woman tied up beneath their son. Being the leader had it's benefits and he not only was first in line to use Karen's pussy, but he was getting to be the first to get her asshole too.

It took some effort, but the Terry finally pushed his whole cock into the madly thrashing woman's ass. Having already enjoyed the blonde's pussy several times, which had felt so good to him, the boy was shocked how hot and tight it was to be inside her butthole. He immediately began madly pounding away between Karen's big, shapely, buttocks, making them quiver, as he vigorously sodomized her. "Guys, this is great!" he panted and the boys all eagerly began lining up for their turn.

Karen's nightmare continued, since anal sex was one of her biggest fears. But now it was happening to her and she was helpless to resist the hard, painful thrusts into her rectum. The blonde's eyes bulged and she screamed herself hoarse into the gag, as the teen made her cry like a little girl. The other boys enjoyed seeing the previously dominant woman's reaction, and all looked forward to doing the same thing to her themselves. 

Having come previously, Terry had staying power that did not match up with his lack of experience. His your shaft was rock hard and he was nowhere near coming, as her pumped away between the short haired blondes sexy cheeks. He could not believe how hot and tight her butt was and realized that this was the most pleasure he had ever experienced before. The teen wanted to enjoy the experience to the maximum, so he started experimenting. He slowed his strokes and vowed to make it last as long as he could, much to Karen's extreme displeasure. 

Terry found that he liked it a lot when he slowly pulled his cock out, until the head was the only part inside their captive's rubbery ring, then rammed the full length back into the woman's tight ass. Listening to her almost inhuman, muffled, shrieks of agony, the boy repeated this process over and over and over again. Gripping the blonde's shoulder for leverage, he drove as much of his dick up her big butt as hard as he could. 

Dominating, controlling, and violating the bound, helpless woman gave the teen a sense of ultimate power and shattering pleasure. Terry vowed to himself that he would buttfuck their attractive captive as many times he could and that he would personally move her car off their block, so they could keep her in the warehouse for a long, long time. The knowledge that they could keep her there, maybe for days, to use as they wanted really excited him. 

He knew from looking through her wallet and purse, while his friends were taking their turn raping her, that the leggy woman was a mother of two, was married, had a good job, and also where she lived. Knowing that he was forcefully sodomizing some man's wife and some kid's mom really, really turned Terry on.

The veins in Karen's neck stood out, as she continued to scream into her gag. The anal sex was worse than she had ever imagined it could be. What the boy was doing to her hurt so badly that she could not stand it. The deep, hard thrusts deep into her tender bottom were unbearable. 

Never in a million years did the blonde think that any man would ever do this to her, that alone a strange teenager and his friends. Being raped repeatedly by all the eighteen year olds was traumatic, but being sodomized was the worst thing that she had ever experienced. But the boy using her ignored her muffled screams, begging, and hoarse cries. At that point, Karen would have paid or done anything, if he would just stop. Her mind could not even consider that there were five more teens waiting to do the exact same thing to her.

As Terry continued to pump away between the crying woman's buttocks, he realized that she kind of reminded him of a slightly younger version of his own mother Linda. The two women shared some characteristics, especially in their bottoms. He had started noticing that his mom had a good looking butt the year before and had started fantasizing about her sexually. All the boys started comparing their mothers, and telling each other how much they had seen of them. 

Picturing his own mom in his mind's eye, and realizing that it could just as easily be her tied beneath him, really excited the boy and he began to take out his deep seated desires for her on their helpless captive.

"Yeah, take it mom...take it." Terry grunted into the blonde's ear as he hammered her tender asshole deep and hard. At first it didn't register through the fog of pain, but Karen became aware that the strange boy raping her was actually calling her his mother. A wave of nausea swept through the woman, sickened by the filthy fantasy the teen was using her to fulfill. 

Never in her life had she even considered someone could think of something so vile. His lusty pants of "Mom, take it...take my whole cock up you...unhhh...pretty ass! Take it all!" made the woman want to vomit. "Oh, yeah mom, here it comes! Take it all!" the teen cried, as his cock jerked inside the blonde's clasping hole and he started to shoot his hot sperm deep into her asshole. Karen nearly threw up in her own mouth as she felt the sickening spurts shooting into her abused rectum.