Castle woke up in a bad mood. Tina had come home from her overnight shift at the diner and was sucking him off so she could go to bed. He was getting hard, but Tina could tell he was in a bad mood and was a bit scared that he might hurt her. He let her work him up until his cock was hard enough, then took handfuls of her brown hair and proceeded to facefuck her. She'd cut her hair somewhat short recently and looked more like a dyke than she usually did, but as long as she left enough hair for him to hold onto he didn't really care.
He started by slowly pushing the full length of his cock down her tight, slightly resistant throat. He didn't mind the resistance. After all, the human throat did not evolve specifically to be a sleeve for a man's cock, but the last couple of years had trained Tina well. She'd started off as a lesbian with a hot body but limited experience with men, and her throat had been as tight as her asshole back then. Getting roughly fucked two to three times a day for the past two years had turned her ass to a gaping mess, but her throat still gripped his fat cock nicely.
So he started with a few full length strokes, then settled into a nice rough facefuck. Her nose started bleeding a few minutes in, and he could tell she wasn't getting enough air and was going a bit limp. She was drooling all over the place and her mouth just hung open slack as he pumped her throat.
The sound was what got him off in the end. He wasn't even looking at her, he just stared at the ceiling as he jerked her head back and forth and masturbated in her throat. The 'glurk' noises she made as he used her throat always turned him on, and hearing his little lesbian make little choking noises while he abused her finally pushed him over the edge. He held her face pressed hard against his groin while he shot a big load directly into her stomach. He felt better. For a few minutes. But then he remembered. Tina was still coughing and gasping on the floor with cum and drool dripping out of her oral fuckhole with blood streaming from her nose when he remembered.
It was November 17.
---
Once upon a time, Castle had been married. He was a dutiful husband who doted on his wife and she repaid him with betrayal. He came out of it a changed man forged in the crucible of hatred. He sometimes fooled himself into thinking he had left that anger behind him and moved on with his life, but on November 17th, the anniversary of their wedding, it all came flooding back. It always came flooding back, and all he could feel was rage.
---
He got Tina an ice pack for her nose and tucked her in. Even when your girlfriend is a lesbian that you have manipulated into being fuck toy, you still can't be quite that rough and just leave. He cuddled her a bit, lightly stroking the pink triangle tattoo on her hip while she fell asleep. They'd been together long enough that her smell almost always made his cock hard. His body had long since equated that smell with exactly the kind of rough sex Castle liked. As she dozed off, he reflected on how she had really become the ideal girlfriend. She had minimal expectations of him, but he used her like a cheap whore almost every single day. The fact that she was a lesbian just made it hotter, and the fact that about a year back he had numbed her clit with botox made it hotter still (see Story #3). Of course, she didn't know about the botox and thought her numbness was from a clit piercing gone wrong, but over the last year she'd been forced to face the fact that her asshole was now her main erogenous zone. She now pushed back eagerly to find what limited pleasure she could as Castle used her asshole, and as far as he could tell neither of them had fingered her clit or pussy for at least six months. Castle loved to bend her over and fuck her in front of the mirror so he could watch her clit piercing flash in the light while they both took pleasure from her now loose asshole.
As she dozed, he briefly considered using her again since he was hard again, but he knew his dark mood would result in more damage and he didn't want to push Tina too far.
---
So, Castle took his small backpack and went for a walk. The pack carried the usual - water, sunscreen, a small snack, a pad of paper and a pen, and a few supplies useful for kidnapping. It was a sunny autumn morning in The City of Angels, and Castle simply walked with no course or agenda until he saw them, and he knew what he would do next. Two lovely brunette girls were in a park sunning themselves when he saw them. They had their cell phones out and were chatting with each other as they played with them. They looked awfully similar, and Castle assumed they had to be sisters. They looked like two college girls having a quick sunbathe before class.
Castle's mouth started watering as the rage surged.
---
The sisters fit neatly in the hatchback of their cute little Honda. It was a simple thing to taze and then inject them with a sedative as they packed up to leave. He took them to a condemned factory he sometimes used. As they slept, he handcuffed them, removed the cash from their wallets, then burned all of their belongings and clothes.
The younger sister was the first to wake. She was gagged and cuffed, and she weakly struggled as her positioned her on her hands and knees and pulled her bathing suit down. She felt the lube as her squirted it between her cheeks and spread it around her fuckholes. He even slid a slippery finger and then two into her pussy before she heard his belt and zipper. She was no virgin, but she was very tight and squealed through her gag as Castle opened her pussy further than it had yet been stretched. She made curious little noises as Castle explored untouched areas of her pussy, and he thought of his past as he fucked her.
---
It had been a perfect setup. Stanley and his wife Linda lived in a low rent area of Oakland. Linda was a pretty little gal with nice curves and light brown hair cut into a short but stylishly cute cut. They'd been married for almost 5 years and he adored her. Stanley and his best friend Paul had a pretty good racket robbing local drug dealers. They'd find a low level guy with limited resources, kick down his door and take the drugs and money he had. Stanley had a nice stash of cash hidden in a secret compartment in their kitchen, and he had almost enough to settle down and start a family with Linda. Paul's wife Emilia was pretty red-headed gal with a big ass and big tits who doted on Paul but didn't seem especially smart.
One Sunday morning, they kicked down a dealer's door. Stanley pistol whipped the dealer until he gave them his cash, and then with no warning Paul shot the dealer. Then, seemingly in slow motion, he turned the gun on Stanley and shot him in the head.
When Stanley woke up, he had a blinding headache and blood pouring from his head. As he laid there trying to understand what happened, he heard sirens.
Stanley willed himself to his feet, cleaned himself up as well as he could, and fled. He walked back to his house, trying to stop the flow of blood from the deep cut on his head where the bullet grazed his skull. He was almost home when he saw his wife Linda and Paul throwing bags in Paul's car. They climbed in and drove off, and Stanley knew he had been betrayed by the two people he loved the most.
---
The college girl was now weeping as Castle pounded her pussy. There was a bit of blood oozing where his fat cock had torn her tight pussy open, and he had both thumbs pulling her asshole apart as he bottomed out into her cervix.
Her older sister woke up as they fucked, and as the drugs wore off she slowly started to understand what she was looking at as Castle smashed into her sister. Tears rolled as she watched. The sound of Castle's hips slamming into her sister and her sister's weeping echoed around the large factory as Castle took pleasure from her holes. He pulled his thumbs from her bleeding asshole and grabbed one handful of lovely brown hair and another of small, firm titmeat as he pounded her. He yanked her dark curly hair back and roughly chewed at her throat as he ravaged her, and the feel of her lovely body against him as she wept through her gag pushed him over the edge. After he filled her tight cunt with cum and collapsed on top of her while catching his breath, he noticed her sister wide eyed and crying, and he could feel his cock hardening again. He smiled grimly when the younger sister, who was currenly wrapped around his cock and had quieted down as they basked in the afterglow, started sobbing as she felt him lengthening again in her young cunt.
---
Paul and Linda had tossed the house looking for Stanley's money, but they couldn't find his hiding spot in the kitchen and had ultimately given up. He retrieved the money, grabbed some clothes and key belongings, and left. He checked himself into a seedy hotel and nursed his wound while he planned his next moves.
Paul's sister, Janice, was a senior in college, about to graduate with a degree in english literature. Despite his criminal leanings, Paul doted on her and made sure she had everything she needed while she was at school. Stanley had always thought that Paul treated her more like a daughter than a sister. She was a lovely blond with long curly hair and a slender but womanly figure. She was one of those girls that was simultaineously a prude, but very flirty, and Stanley had always wanted to fuck her.
Stanley took her as she climbed in her car.
It was relatively easy to break her. First, he fucked her. She was a tight piece of ass and Stanley figured he might as well take a bit of revenge out of Paul's sister's tight cunt. She cried and weakly fought him as he lay on top of her and pounded her almost painfully tight cunt. He actually had to get up and lube his cock at one point so he could fuck her without rubbing his cock raw. The cheap hotel he was staying in was immune to the sound of rough sex, so he was free to use her as he wanted. Before he asked he a single question, he had pounded through a very rough rape-fuck, slapping her face and spitting on her as he spent the rage he felt at his unfaithful wife on this lovely young woman.
After he spat his cum into her young pussy, he lay on her feeling her gently weep as her pussy twitched around his fat cock, and he decided the interrogation could wait. He positioned the now compliant Janice on her hands and knees, lubed his cock again, grabbed a handful of her long blond hair, and pushed back into her pussy. He idly thought about how her pussy was definitely looser than their first fuck as he raped her again.
By the third rape, she was again on her back; her cries had died down and she barely responded as he roughly slapped her face and pounded into her now loose pussy. He chewed her lips like an animal as he emptied another load of rage and sperm into the lovely Janice.
He left her laying on the bed as he took a piss and a drink of water. As they both caught their breath, he watched her slender, young, sweaty body as she recovered from the brutal fuck session. She looked over at him, and as he looked into her eyes he set down his glass, walked back to her, lined his cock up with her fucked out cunt, and pushed back inside.
Stanley paused there as they looked at each other. He gave her a hard slap, wrapped one hand around her throat and grabbed one of her sweet young tits with the other as he decided to see how many times her suffering and her now sloppy cunt could make him cum.
---
Castle decided the older sister must have been pretty slutty. Her pussy was nowhere as tight as her younger sister's, so he switched to her asshole. Now it was the younger sister's turn to watch and cry as Castle roughly used her sibling. Once again the sounds of hips slapping echoed around the factory, this time accompanied with loud guttural grunts from the older sister as she was brutally sodomized. Her asshole her obviously been used, but it was much tighter than her pussy and Castle got into a very nice rhythm as he pounded her hole. He used her hips as handles as he pumped, and occasionally slapped her ass cheek as he used her. The older sister was decidedly more plump then her younger sibling, and she had a lovely round ass which made for a very, very nice buttfuck. Castle wondered how many others had used her most private hole as he took her, then decided it couldn't have been very many because she was still pretty tight. As he took pleasure from her clenching asshole, and her gentle weeping ultimately pushed him over the edge, and he grabbed the younger sister's hair and forced his cock into her mouth as he came. He had a moment of clarity as he saw the tracks of tears down the younger sister's face, and the brown smears on his cock that were being transferred to the younger sister's lips.
---
Stanley ended up fucking Janice for the better part of six weeks. He would tie her up when he went out for supplies, then nap intermittently and then roll over and use her whenever the desire took him. She spent many hours kneeling between his legs trying to suck one more load out of him as he watched shitty tv. A few days after he took her, he raped her virgin asshole for the first time and discovered the intense pleasure of taking a woman's most private hole. Her formerly tight asshole now gaped slightly all the time from daily use.
She was a wonderful therapy tool to help Stanley come to grips with his cheating whore wife. He simply did whatever he wanted to Janice, and she had no say. He usually beat her when he fucked her. Mostly he slapped her face, ass, tits, or pussy when he used her, but the abuse had escalated to occasionally punching her in the belly or kidneys as he used her. She took the abuse in relative silence, knowing that no one cared about her situation. He had one memorable session where he fucked her missionary and as he started to come he choked her while brutally slapping her face over and over. He came like a firehose, but she was choking and her lips and nose were bleeding afterward.
He started burning her with cigarettes. He would make her rub her clit until she was about to cum, then he could glide a lit cigarette across his pussy lips and asshole. She would sob the entire time because she knew what he planned, and she would squeal in pain when the cigarette kissed her skin, but he made her keep rubbing. When she was about to cum, he'd burn her again. Stanley found it incredible to drive her again and again to the brink of orgasm, and then to bring her back down with intense pain. Usually the session culminated with Stanley jamming his hard cock between her burned pussy lips or asshole and roughly pounding her while he put out the cigarette somewhere on her skin. The pain would drive her to clench her hole and help drain his balls as he enjoyed her pain. It was after one of these sessions that Stanley realized he was a sadist. Janice was weakly sobbing and sucking him clean after a particularly nasty fuck session. He had burned her while she played with ther clit for over a hour, and then bent her over and emptied his balls into her pussy while shoving most of his hand in her asshole. After he came in her, he collapsed and, without direction from him, she used her mouth to clean his dirty cock. At that moment, he realized that inflicting pain on a woman was simply the greatest turn on he had found. He had never met anyone like her.
---
The brown shit streaks were still on the younger sister's face as she ate her sister's pussy. It was only after he had fucked both of them and coerced them into giving him a lezzie show that he realized he had burned their purses before he learned their names.
He idly wondered what their names could be as he watched the sisters sixty-nine. The older sister on top, and her ass was facing Castle. He could clearly see the younger sister licking and sucking her sibling's long twat lips while the older sis' asshole clenched and gaped slightly from their recent fuck session. Castle watched absentmindedly as a red-tinged trickle of his cum leaked from her open sphincter and slowly ran down her taint and into her sister's active mouth.
After ten minutes or so, their incestuous show had him hard again. The younger sister had bit her lip and groaned in pleasure a couple of times as her more experienced sibling ate her pussy, and the filthiness of what he had wrought made Castle hard as a rock. He slid over, and while the sisters learned to please each other, Castle slid his fat cock back into the older sister's well-fucked shithole. After a few pumps, he slowly pulled out and pushed his newly brown stained cock into the younger sister's mouth. She made a little noise of disgust but didn't even gag as she cleaned her sister's shit from him.
Then he pushed back into the older sister and settled in for nice long buttfuck she grunted into her younger sister's formerly tight pussy. After a very long and satisfying fuck, Castle emptied his balls in the older sister's guts again when his rage came back. It seemed like it snuck up on him until he was neck deep in a flash flood of anger. He pulled out of the coed's now gaping hole and fed his brown streaked cock back into her sister's mouth. Then he reached over and grabbed his belt, and he proceeded to beat the older sister's thick ass as hard as he could. She screamed and tried to writhe away and he used one hand to skullfuck the younger sister with his shitty cock and the other to slash at the older sister with his thick leather belt.
Castle ultimately lost track of time and collapsed in an exhausted heap. He pulled the younger sister down with him and she kept sucking to avoid her sister's fate. Meanwhile the older sister had seemingly passed out sprawled on her belly and a thin bead of blood swelled from many spots on her fat ass cheeks where Castle had brutally beaten her. As the younger sister nursed his cock, he stared at her sister's fucked out and swollen asshole.
---
After the first few weeks, Janice actually started cumming as he burned her. Small circular burn scars pockmarked her tits and ass, and there were many on other parts of her body as well. It was initially an interesting novelty to make her cum from pain, and Stanley quite enjoyed making her squirm in pleasure and pain as he scarred her by putting out a cigarette on her tit. These days when her fucked her asshole, it was often red and burned from having a couple of cigarettes stubbed out on it, but she usually rubbed her pussy and came from the pain as he pumped into her loose and damaged hole.
The thrill of having a true pain slut helped Stanley forget about Paul and Linda for a while, and they both explored how far she could go. In what was likely Stanley's favorite session with her, Janice edged her clit while Stanley burned her nipples and pussy lips with a cigarette. She almost came as he pushed safety pins thru her burned nipples, but he slapped her back to reality. She kept edging as he stubbed a few cigarettes out on her pussy lips and the finally mounted her in missionary position and started fucking her. She groaned loudly as her red and damaged cunt lips wrapped around his fat cock, and when he pushed her legs back further and pushed his cock into her asshole, she groaned in pain but kept rubbing her clit.
He used her brutally, roughly switching between her loose pussy and her well-used asshole and finally draining his balls in her guts as he slapped her face and roughly squeezed her damaged and freshly pierced tit. She squealed and came as the pain from Stanley crushing her safety pinned nipple in his palm and pushed her over the edge. When Stanley pulled his cock from her ass and rolled off her, he watched the blood trickle from her burned and pierced nipples and asked her about where her brother was hiding.
---
Unsurprisingly, the older sister was better at sucking Castle's cock. He had nicknamed the younger sister "Little", and she was currently mouthing his balls while "Big" was trying to coax one more load out of Castle's cock. Looking down to see two very pretty and very similar looking curly haired brunettes trying to hard to please him made Castle's cock swell. He took handfuls of Big's dark hair and pushed her face down on his cock. There was a moment when he felt his cockhead make contact with her throat and she instinctively pulled back, but he tightened his grip on her hair and pulled a bit harder and slid down her throat toward her stomach. He closed he eyes and relished the sensation of the pretty young co-ed's nose pressed again his groin as he enjoyed her throat and her younger sister gently sucked on his balls.
He pulled her head off his cock, let her take a breath, then took her throat again. After a few throat insertions, Castle had her lube his cock while her sister kept sucking his balls, then he slid it back into Big's new fuckhole. He started off slow but built up to a nice rhythm as he pumped his fat cock in and out of her throat. Big tried to take it well so he wouldn't hurt her, but ultimately she couldn't help it and started gagging and drooling. When couldn't take anymore and pulled back to take a break, Castle would grab a handful of hair and slap her a few times until she was ready to swallow his cock again. After about 10 minutes of abusing her, Big collapsed in a heap, her lovely young and bruised tits heaving as she tried to catch her breath. Castle simply took a handful of Little's hair and lifted her face from his balls to cock. He smiled and said "I guess it's your turn now" as he slid over Little's tongue and felt his cockhead press against her virgin throat.
---
Stanley ultimately lost interest in Janice. She simply liked it too much. No matter how he hurt her, she didn't mind. She sometimes looked at him like she would do anything for him, and she had proven that devotion early that morning when he pissed down her throat rather than get out of bed and use the toilet. She swallowed it without complaint, and then tried to suck him hard before he slapped her away and went back to sleep.
When he finally got up, he told her to dress because they were going out. That a was a big deal because she hadn't been out of the dingy hotel room for six weeks. He had her wear a tight tube dress he had gotten for her, with only tiny thong underwear beneath. Her generous tits bounced in the thin fabric as she walked, and the lobby lizards certainly noticed the pretty young blond in the tight short dress as they left.
Stanley took her to a drive thru where they got burgers, then he drove her to a part of Oakland she had never been where prostitutes stood all around their car, and he told her to get out. Understanding his intent, she wept and begged him not to leave her. Stanley realized that he couldn't enjoy physically hurting her anymore, because she had grown to like it. All he could do now was hurt her emotionally, and so he left her, weeping and begging him to take her back. She promised to do anything he wanted, anything he could think of, which he considered as he drove away and left her there.
But he didn't abandon her completely. He went back a couple of weeks later and there she was, in the same dress, turning tricks on a street corner with a black eye. Stanley took grim satisfaction knowing that the former English major about to graduate from college was now a full time pain whore who would fuck anyone who had a bit of cash to spare. He wondered how long she would last and what would happen to her afterward. She was in her early 20s, so she had to have at least 10, if not 20 years of whoring ahead of her. He decided that he would stop by from time to time to see if she was still here, and maybe he'd pay for a blowjob for old time's sake.
About a month into their time together, Janice had told Stanley exactly where to find Paul. Stanley was a bit surprised how much she knew, but apparently the Paul and his sister shared everything. Paul had used the heist money to set himself up as a drug dealer in San Francisco. Emilia was still his wife and seemed to know nothing about Linda, who lived a few blocks away and who Paul fucked as often as he could. After he introduced Janice to her new career, Stanley watched Paul for a couple of weeks as he planned his revenge, then when everything fell into place, he acted.
---
Big had ended up taking his fist in her pussy. She obviously didn't think it would fit, and frankly Castle wasn't sure, but as Little nursed on his cock he kept pushing and twisting until with a squeal of pain from Big and a groan of satisfaction from Castle, her young cunt swallowed his hand. She tried to wiggle away but was handcuffed to a pipe so couldn't get far as Castle formed a fist and proceeded to destroy her young pussy. Little managed to suck two more loads out of his balls during the long fisting session as he ruined her older sister's pussy. By the end, Big was a blown out drooling mess and his clenched fist slid easily in and out of her loose hole. She was bleeding a little, but it certainly wasn't life threatening.
Big was alternating between grunting and gentle sobbing as Castle absentmindedly pulled his clenched fist out and pushed it back in to her loose pussy, and Little was making quiet weeping noises as she gently sucked his cock, but Castle was lost in thought as he remembered.
---
Stanley broke into Paul's house and planted the drugs and guns he had brought. A previous break in had taught Stanley that Paul kept most of the drugs he sold somewhere else, so Stanley planted enough that, combined with the illegal guns, Paul would be facing decades in prison. He also brought in a fire-proof lock box and left it empty with the key in the lock.
After the plant was complete, Stanley waited in the house until Emilia came home. He tazed her and gave her a shot to knock her out. He put her fingerprints on the key to the lockbox, then loaded her in the truck of her car in the garage.
As he drove away in Emilia's car while she dozed in the trunk, he used a burner phone to call the police and anonymously report Paul.
Later that afternoon, Emilia was naked and crying with her hands cuffed and a ball gag in her mouth. She was on all fours and Stanley was pumping her milfy pussy while the TV news told the story of the dangerous drug dealer who had been arrested and was facing serious weapons and drug changes. Stanley slapped her ass a few times, grabbed a handful of her chestnut hair, and made her watch it while fucked her from behind and, after the news story ended, he explained what had happened since the moment Paul had shot him. She cried even harder as he detailed what he did to Janice and her eventual fate as a cheap whore. But then he told her what he planned to do with her, and her violent sobbing drove him to empty his balls much faster than he had planned. As he caught his breath, she collapsed on the ground sobbing. Stanley felt his cock twitch at the sight.
---
Castle woke up with a bit of a start. Little was laying between his legs, asleep with her face laying on his leg. It looked like she had fallen asleep while sucking him. He then realized his hand was still in Big's pussy. Big was also sleeping, although Castle was surprised she could sleep laying on the hard ground with her hands cuffed to the pipe. It was dark outside, so it had been a few hours since Castle had fallen asleep.
He tentatively moved the hand still in Big's pussy and realized that the lube had long ago dried out and that he would almost certainly damage her if he pulled his hand out. He decided he wanted to sleep more, so he used his free hand to reach in his bag and grab a couple of syringes of sedative. He shot up Little first, then gave a larger prepared dose to Big. Both twitched as the tiny needle pierced their skin, but being brutally raped is exhausting, and neither seemed to actually wake up. Castle laid back and let himself slowly drift back to sleep while stretching out the fingers of his trapped hand and feeling around Big's cervix, enjoying the obscenity of the act.
---
The day after Stanley took Emilia, he waited until very late at night, then quietly broke into Linda's apartment. He tazed her in her sleep, then gave her a shot to knock her out.
He carried her out to her car, dumped her in the trunk, and drove away, locking her apartment door behind him.
The next morning two guys from a local car breaker picked up the women's cars. Stanley and Paul had used them to dispose of vehicles in the past. The cars would vanish.
Stanley tied Emilia in a corner, turned the tv up loud, and spent most of the day demonstrating his displeasure to his cheating piece of shit ex-wife. By lunchtime, her face was swollen and her nose was a different shape than it had been, and she had small burn marks all over her body from his cigarettes. He hadn't bothered to fuck her pussy, a hole he had been in many times. When her pain first got him hard, he used a dental speculum to keep her mouth open and used her throat. She'd gagged and choked and vomited, but eventually he pressed her broken nose against his pubic hair and had a very satisfying cum in her throat. Then he started hurting her again.
Later that day, Stanley stood in the middle of his shitty hotel room as Emilia tried to deepthroat him and his wife pressed her damaged nose deep in his crack and tongued his asshole. As they tried to please him, the local tv news told the story of the drug dealer's missing wife. Due to the open and empty lock box, police suspected she had stolen some of her husband's money and then had a male friend report him so she could get away. An APB had been issued and her picture and car were described. Stanley used her brown hair to force his way into her tight throat as he pushed his asshole back against his ex-wife's tongue. Emilia made gentle glurk noises as he pushed her throat on and off of his cock, and the tv news show had just ended as he emptied his balls in to Paul's wife's throat while his asshole clenched around the cheating whore's tongue that was deep in his ass.
---
Castle woke up before the girls, with his hand was still in Big's pussy. He lay on the dirty mattress for a few moments as dawn spread her long golden fingers thru the windows of the abandoned factory. Eventually he decided it was time to get up, so woke up Little and told her start sucking. A few seconds after she wrapped her lips around him, he said, "drink it, do not spill any if you want to live" and started pissing in her mouth. He knew she'd be shocked so he started with just a spurt before he clamped down, waiting for her to swallow before he gave her another squirt. He gradually fed her the contents of his bladder, and she drank his piss without a single complaint. When he was finished, they had a moment where she looked him in the eyes, and he just smiled and said, "good girl, now you can suck out your breakfast". She started working his cock again as he reached for the lube.
Big was still out cold, and his hand was effectively stuck in her cunt after being there for many hours. With his free hand he squirted lube on her mound and then rubbed it along his wrist. With his trapped hand, he gradually worked it around to spread the lube. He ended up sliding the lubed up fingers from his free hand into her pussy along side his trapped hand to spread the lube, and his trapped hand started to move a tiny bit. Meanwhile, Little had used her new deepthroat skills to work him up to a nice cum, and he paused from the effort to free his hand for a few seconds while he used his free hand to guide Little's head as she swallowed the breakfast she'd earned.
As Little nursed the last few drops of cum from his cock, Big finally started to wake up as Castle worked his hand loose from her cunt. He finally got enough lube in her that he could pull his hand out, but it was still pretty dry and was surprisingly difficult. Big lurched in pain as he yanked it out, but then she fell back into a drugged sleep. As she laid there with her legs splayed out, her ruined pussy hung open to exactly the size of Castle's thick wrist. With her younger sister still gently sucking on his spent cock, Castle thought he might be able to see her cervix thru the gaping hole he had made.
---
Stanley took his time with Emilia and Linda. He was in no hurry.
His memories of his time with them were like snapshots of depravity. Those memories were laced with sadness due to his wife and best friend's betrayal, but later he realized that his time with those women tempered him into the man he later became.
Emilia was bent over, Stanley was deep in her asshole. Linda laid on her back with legs spread, and Emilia had her hand in Linda's pussy and was pumping it roughly in and out, as she knew Stanley expected. Both women grunted gently in pain as Stanley took his pleasure.
---
Another time, Emilia was on the couch of the hotel room, on her back with her legs spread as she was pumping a huge dildo in and out of her pussy. Both women had lost weight, and the mostly sexual but physically difficult daily activities they performed had toned them into slender, slightly muscular MILFs.
As she pumped the fist sized dildo in and out of her cunt, Emilia made all the right sounds, not like a over-acting pornstar but like a woman in heat trying to get herself off. Stanley knew better; her act wasn't quite convincing. But that only made it hotter as she tried to please him while he sat and Linda pumped her throat on and off of his fat cock. Her broken nose had healed, Stanley liked the way Linda's flattened and crooked nose changed her face. He enjoyed the fact that he had permanently changed something as fundamental as the appearance of her face. No matter what happened in the future, she could never go back to who she was. Linda gagged occasionally, but she knew there would be pain if she didn't please him, so she fought for control over her body and fucked her throat onto Stanley as Emilia performed. Stanley didn't move a muscle and let the women work until he sprayed the contents of his balls into his ex-wife's throat.
---
Emilia and Linda were bent over, pushing their asses back at Stanley. They knew what was expected and wiggled their asses invitingly as Stanley used them. He was currently fucking Emilia's pussy with his thumb deep in her loosened asshole, but he was watching his ex as she tried to entice him to fuck her. It had been a several weeks and the women were well trained; they knew that enthusiastically emptying Stanley's balls was the only way to avoid pain, and that no matter what degrading act he desired it was preferable to Stanley's punishment. He pulled out of Emilia and moved over to Linda, and then pushed his wet cock into her asshole. It was her first buttfuck of the day, so she grunted in pain as he opened her. He grabbed a handful of her hair and started railing her as Emilia wiggled her ass and begged for him to come back to her.
---
Castle took Big for one more buttfuck. Her pussy seemed ruined. Any time she opened her legs, it just hung open, and out of curiosity Castle slid his cock in. There was almost no friction if she opened her legs at all. Castle idly wondered if it would ever tighten back up without surgical intervention, but ultimately he didn't care.
Still cuffed to the pipe, he put Big on her hands and knees, lubed up, and slid into her asshole. He grabbed a handful of her long brown curly hair and settled in for a nice long fuck. Her asshole gripped him loosely, and as he rode her, he felt Little crawl behind him and start sucking on his balls.
It took a while. He was pretty fucked out from the night before, and while Big's asshole was much tighter than her ruined and gaping pussy, it was still pretty damaged. Little helped, but Castle couldn't decide if she was trying to end her sister's torment or just trying to get him off like she knew he expected. After he came and pulled out, without a word from Castle, Little sucked out the last drops of his cum, then when he pointed at Big's gaping asshole, Little put her mouth to her sister's hole and sucked Castle's cum out.
---
It took months, but Stanley finally got bored with the women. Paul had been sentenced to 45 years for his drug and weapons charges after one of the guns turned out to have been used in a Oakland killing (dumb luck for Stanley because he bought them from a fence). Emilia was wanted by the police, but Linda's disappearance had barely raised an eyebrow since the only person who cared about her was in prison for a long time.
He had tortured and fucked Paul's women until they did what ever he wanted, often without him even vocalizing it. They knew what he expected, and they acted without hesitation. Both were enthusiastic piss drinkers. Both drank his cum like it was the nectar of the gods. Each was happy to fist themselves or the other to keep Stanley interested.
He had them torture each other. He remembered fucking Emilia while Linda gently stroked a burning cigarette across her nipples. Later, he remembered the feeling of Linda's asshole clenching around his cock as Emilia pushed a needle thru her nipple, and then clench even harder a long needle passed thru Linda's titmeat and pushed into the other tit. Linda groaned in pain with that second penetration, and her asshole milked Castle even harder.
They put on lesbian shows for him. They pissed on each other and drank it. They even fought for the privilege of fucking him. On one memorable occasion, he watched Emilia suck his hard cock as her eye swelled shut and turned black after Linda got in a lucky hit but still lost the fight. Bruised and hurt, Linda watched while shoving a huge dildo in her snatch as her opponent worked to empty Stanley's balls.
He remembered the time they tied and gagged Linda, and Emilia whipped her until she passed out. Linda was a bleeding, ruined mess, and Stanley rewarded Emilia by fucking her pussy until she came. Emilia had not had an orgasm for weeks, and Stanley could tell the experience bonded them against their common foe - Linda.
Stanley loved playing Emilia against Linda, and he took that tension as far as he could. He let Emilia direct Linda's actions during their sex, and even let Emilia use Linda for her own pleasure. Linda became their sex toy, they abused her according to their whims. The situation evolved to where Emilia and Stanley would fuck, but Emilia would direct Linda to perform acts that brought them pleasure. Linda's saliva was very often the lube the helped Stanley fuck one of Emilia's holes, and when either of them needed a break, a brutal whipping for Linda was often the catalyst for another round of Linda-lubricated fucking. Stanley never got tired of resting from beating Linda while she slobbered on his cock so he could fuck Emilia.
It gradually evolved into a understanding that Stanley wouldn't hurt Emilia nearly as much if she regularly hurt Linda. Emilia knew that Linda was her husband's mistress, so she has happy hurt Linda, especially if it made her life easier.
After two months, Linda was a patchwork of scars from cigarette burns and piercings. It was a beautiful relationship. He loved watching the fear in his ex-wife's eyes when Emilia hurt her, and he loved knowing that Paul's not-very-bright wife was a tool he used to damage his wife and empty his balls.
By the end, Emilia was effectively Stanley's girlfriend. She doted on him and tried her best to please him while they both treated Linda as their pain slave. Linda was less than human, and each of them used her for their pleasure. It seemed to her that she spent the entire day performing one degrading act after another and being passed back and forth between Stanley and Emilia like the sex toy she had become.
One of Emilia's favorite recent activities was using Linda as her toilet paper, and after she told him about it, Stanley had quickly realized how much more pleasant it was to have Linda tongue his ass clean than to use toilet paper. Emilia taught Linda to clean them with a series of gentle kisses and licks on their dirty holes, which usually got them hot enough that after she had cleaned them up Linda then had to get them off. At first, Linda would have to kneel and watch as they emptied them selves in the toilet, but Stanley quickly realized that having Linda suck him off while he took a shit was one of the most intense pleasures he had ever felt. Linda spent a lot of her time in the bathroom.
However, all things end, and Stanley eventually decided he was ready to move on.
---
Castle could have kept Big and Little longer, but the anniversary was past, and, while the anger still smoldered, Castle was sated. He drugged then tied the girls and loaded them in the trunk of their Honda.
The drive to Tijuana was uneventful, and his connection at the border crossing got him across with no drama. He called a few minutes out, and when he pulled up behind Diego's whore house the man himself was waiting.
Diego and Castle chatted while Diego's men unloaded the women. "Is this the standard deal? Are they going home eventually?" Castle simply replied, "Nope, these girls are yours."
Diego stopped his men and inspected the women, then clapped Castle on the arm and said, "My friend, let me buy you a tequila, and we'll count out your money. Today will be a nice payday for you as the women are young and lovely, and will entertain many, many guests before they must be sold to a cheaper burdel. And since they are sisters, there are even more opportunities for them to please a man as he has likely never seen."
---
Through his criminal friends, Stanley made some contacts down in Mexico. He was done fucking Linda and Emilia with his own cock, but he wanted them to pay for the rest of their lives. He knew that Emilia had done nothing wrong and would feel terribly betrayed as she had done everything she could to keep Stanley happy. He had told her his plan when he first took her, and he was certain much of the reason she'd tried so hard to please him to avoid that fate. But the thought of betraying her and selling her into prostitution anyway made his cock twitch. Then, of course, Linda the cheating whore who conspired to murder him deserved all the punishment Stanley could arrange and more.
Stanley's new friend at the border crossing earned his large payment by making the crossing easy, and Stanley arrived at the back door to the whore house. Almost immediately, the door opened and a slender but nasty looking Mexican came out. He introduced himself in perfect English and said, "I'm Diego." They shook hands.
---
After Diego paid him, he asked Castle, "I noticed the date, do you want your special girl?"
Castle sipped his tequila and said "Please." Diego nodded and left.
About ten minutes later, the woman arrived. She'd been at Diego's for a little under 13 years, and she looked like it. She was wrinked far beyond her years. Her long light brown hair had gray streaks that made her seem older than her 41 years of age. Her broken nose made Castle smile as he remembered facefucking her so hard that he hard that he barely heard the crunch of her nose. That was a good memory. The tattoos marked her as Diego's property and also depicted lewd but memorable acts she had performed on Diego's stage. The thigh tattoo of her fucking a great dane brought back fond recollections for Castle, and the multitude of scars peppering her body told of a million little agonies that he could only enjoy imagining. Castle smiled as he said, "Hello, Linda, it's been another year."
He knew time had little meaning to her. For over a decade, every waking moment of her life had been belonging to a random man for one 30 minute sequence after another. Diego kept his prices low to ensure business, and Linda had long been the cheapest whore he sold. She was far past her prime and Diego only kept her as a favor to Castle, so he kept her price low enough that any man could fuck her if he just needed a set of holes to abuse. Diego sometimes told men of her story and how she was a whore only because she cheated on the wrong man. Diego said those sessions always made more money, but she tended to be more damaged afterward as the men punished her for her crimes. The result was that, according to Diego, she had fucked an average of 25 men per day for close to 13 years. That meant she had been fucked close to 120,000 times since Castle delivered her to Diego. And as she got older and more used up, these men were consistently the dirtiest, most poor men in Tijuana.
Without a word, she pulled Castle's hard cock out and expertly sucked him hard. Castle talked while she sucked.
"Happy anniversary, baby. It's been 17 years since we tied the knot. We're still legally married, by the way. I have to wonder if there's another man on earth whose wife has fucked so many strangers."
She slid his slobbery cock into her throat as he spoke. Castle groaned in pleasure and thought back to her weak blowjob skills when they lived together. So many years in a brothel had taught her how to swallow cock incredibly well.
"That makes almost 13 years since you began your new life. Lately, I sometimes wonder..." He paused as Linda gently squeezed his balls and fucked her throat on and off his cock. The soft glurk sound her throat made as she skullfucked herself on Castle's cock filled the room for a few seconds.
"I sometimes wonder if I should bring you home."
She paused throating him for just a split second and looked him in the eye, then drove her head back down onto his cock. A tear rolled down her face.
"You're right, it's better this way. Absence does make the heart grow fonder, after all."
She made a little choking noise as she fucked Castle's fat cock with her throat. He picked up his glass and took another sip of Diego's best tequila. Then he closed his eyes and gave himself to the pleasure, muttering, "yeah, it's better this way."
When she thought he was close, Linda wetted a finger with the drool running off Castle's cock and slid it in his asshole. She teased him a bit, then as he was close to cumming, she started gently fingering his prostate while she massaged his balls and stroked his cock with her throat. This was a technique she learned from a Panamanian whore named Teresa who had been at the brothel several years back. Teresa claimed that even though they were uncomfortable with it, most men would come in seconds when a whore started rubbing their prostate. Teresa proved it many times to Linda, and years ago Linda had started using it regularly.
Linda still teased him, she just used his balls and prostate to make the teasing more intense. Several years back, she had made Castle cum too fast and he beat her with a belt until he was hard again, and she learned her lesson. She wanted it to be as good for her ex-husband as she could manage.
She would pause with his cock in her throat and try to swallow to massage him while she gently worked his balls and prostate. After, while she caught her breath, she looked Castle in his eyes while she seductively sucked on the finger that had been in his ass and finally Castle said, "I'm ready, drain my balls, baby." She forced a smile and added her middle finger to her mouth to get it wet, then looked him the eye as she slowly slid both fingers into his ass, wrapped her remaining fingers around his balls, and resumed skullfucking herself with Castle's fat cock.
He fought as long as he could, but just a few minutes later he had handfuls of hair and was pressing her lips around the base of his cock, and as she choked and began to feel light headed from lack of air, she kept enough self-awareness to dig her fingers into his prostate to heighten his pleasure.
He couldn't believe how hard he came. When he finally let go of her hair, she pulled her head back and began gasping for air. Laying there panting and looking at each other, with her fingers still in his ass and her hand gently around his balls, Castle said, "You still drive me crazy, baby. Let's catch our breath and you can do that again. I'd fuck you baby, just like the old times, but with all the dirty guys you fuck I'm worried I might catch something."
She said nothing, but nodded her agreement as she tried to catch her breath. Castle noticed a tear rolling down her cheek and smiled. When he saw a second tear, he felt his cock starting to harden.
***
Stanley stayed at Diego's for three days that first time. They took turns fucking Emilia and Linda until they needed a break, and then Diego's men took turns on the women. Stanley got hard again later watching Linda grunt in pain while sandwiched between two rough looking Mexicans. The guy in her ass had a large cock was using it very aggressively while the guy underneath her roughly chewed and bit at her ears, neck, and lips while she writhed on his cock. During his next turn, Stanley had her ride the big Mexican's cock while he raped her ass with his slightly larger cock. Despite her exhaustion and how fucked out she already was, being roughly hammered by the two biggest cocks in the room had her squealing and crying and making other inhuman sounds. Finally one of the other Mexicans shoved his cock down her throat to shut her up, so only the occasional screech or weird glucking noise escaped her. Instead, the room was filled with the sound of the slapping of hips and occasionally hands hitting her skin, and finally the groans of two men as they emptied their balls in her painfully stretched holes.
Emilia took her gangbang much more easily. She seemed to just zone out and lay there as the men used her. The men weren't quite as rough with Emilia, though Stanley did realize that her holes seemed to get much looser than Linda's as the night went on. She was loose enough that, when Castle and Diego fucked her together, they ended up pushing both of their cocks in the pussy to tighten her up a bit. She squealed a bit during her double-pussy fuck, but she quickly adjusted and went back to being boring. The most rewarding part for Stanley was the hurt look in her eyes as she stared at him while he and Diego double-fucked her pussy. He enjoyed her feeling of betrayal, but he quickly decided it was much more fun to abuse Linda.
Stanley and Diego bonded over their abuse of Linda, and Diego offered Stanley a job at one point. Stanley seriously considered it, but he knew the party couldn't last forever and felt like there had to be something out there that suited him better.
When Stanley left, he agreed to come back, and Diego promised him Linda would still be there. Stanley drove back to San Francisco contemplating his future. Robbing criminals had not worked out so well. There had to be a better way to make money. Meanwhile, his time with Paul's women and ultimately his time with Diego had shown him how much he enjoyed hurting women. As he was driving thru Los Angeles, it occurred to him that being a Private Investigator seemed like it might be a good way to proper off other's peoples misfortune and meet a lot of vulnerable women along the way. The gears turned in Stanley's head as he thought, "well, Stanley Yankovic is not a great detective name, so I guess I need to think of something else..."
***
Late the next morning, Castle drove back to LA. He was basking in the afterglow of abusing his ex-wife, pleased that she was still attractive even though so she had been used so roughly and for so long. Even better, Diego planned to have her sent to a plastic surgeon that specialized in bimbos to reshape her tits and ass and tighten her belly to try to make more money off of her. Castle offered to pay for the surgery because he knew his friend only kept her to please Castle, but Diego simply said, "No, my friend, I will make my money back from her improvements and I choose to keep her here as a gift to you." Castle was touched.
As Castle drove, he realized that he again forgot to ask what happened to Emilia. She simply disappeared a few years back, and Castle kept forgetting to ask Diego about her. He knew the range of possibilities - sold to a wealthy man, sold to a cartel to entertain their men, or sold to a cheaper brothel because she'd gotten to old and worn out for Diego's place. Castle had long ago decided the latter was the most likely, as her reddish brown hair and lovely body had been a novelty, so she'd been used more than most of the women at Diego's for the decade that she was there. Castle knew that usually Diego sold his used up product to a brothel deep in the south that catered to a small mining community. He imagined Emilia's delicate hands wrapped around yet another smelly, sweat-soaked miner's cock, and he smiled. He idly wondered where women went after they were too fucked out for the mining camp brothel. He supposed she'd be sold off to a miner to warm his bed, or more likely to a local bar or restaurant as slave labor and to be rented out for an occasional cheap fuck. He enjoyed thinking about pretty little Emilia working her soft hands to the bone waiting tables, scrubbing floors, and, cleaning dishes while occasionally bending over so the owner could hike up her dress and empty his balls into her when the urge hit him.