Tina was half way through her overnight shift at the diner, but the night seemed longer than usual because she felt like an asshole. More accurately, she felt her asshole. Constantly.
While most people might not feel their asshole all day long, Castle had been using Tina's fuckhole so much lately that it seemed to throb all the time. It distracted her much of the day, as it felt loose and tender from Castle's rough use, and she was continually surprised how, even hours after they fucked, his cum would occasionally drool from her loose hole. She had recently started keeping an extra pair of underwear in her purse for days where a lot of cum leaked out, and lately she'd been thinking she might need to start wearing a panty liner to catch his cum.
She was daydreaming about their last buttfuck, how Castle had tenderly sucked her neck and ears while he pumped her ass from behind. She thought she might be able to cum with her asshole eventually if Castle took the time to work her up to it, and this afternoon before she went to work, she had gotten very close. Castle had played her masterfully, but right as she thought she might cum, he grabbed a handful of her chestnut hair and escalated until he was pounding her guts. His roughness threw her out of her zone, and he ended up spraying his jizz deep in her bowels while she twitched in pre-orgasmic pleasure on his cock. Hours later in the diner, her asshole clenched unconsciously as she relived the fuck and felt the emptiness in her swollen fuck hole.
Her phone dinged, and she sighed when she looked at it. Her younger sister had just left her husband and needed a place to stay. She wondered how Castle would react when she replied "Come to my place, I'll be there by 8 am."
***
Personality wise, Kim was the opposite of Tina. Kim was 6 years younger, and while their abusive father had driver Tina to dislike and distrust men, Kim had seemingly had a few boyfriends with no significant complications. She met Trevor working at a local Walmart and they married a couple of years back.
Physically, the sisters were similar. Both were lean and tallish with dark hair and tanned skin, and both had breasts that were slightly large for their frame. Kim had a slightly more feminine facial features, while Tina could be described as handsome. However, both were attractive. Each had gotten a lot of attention in high school and boys had fawned on them. Tina had realized in her teens that she preferred women, so the boys were an annoyance, but Kim loved the attention.
Tina was never sure she liked Kim. Kim was prettier, Kim was girlier, Kim never seemed to receive the abuse from their father that Tina did. When Kim got married, it was just another sign to Tina that Kim was better integrated into the world than Tina was, and Tina hated her a little for it.
When Tina got back to her apartment, she was exhausted from a busy night at work and was idly thinking she needed to change her underwear as she pretty sure Castle's cum was leaking again when she saw her sister and remembered.
She brought Kim in, got her set up in her son's old bedroom, which was unoccupied since he moved out, then quietly slipped out the door. She went next door to Castle's to provide his morning blow-job and possible buttfuck depending on his mood.
Tina silently crept in the room and climbed under the covers, then gently freed Castle's cock and started mouthing it. She felt her asshole clenching as he hardened, and she hoped that if he used her ass he'd try to get her off. She nursed his cock until it was hard, then he finally sat up and climbed behind her. He hiked up her waitress skirt and peeled down her panties.
"My little lesbian has cum in her underwear again."
She felt a blush of humiliation and thought she could hear the smirk as he took pride in his work.
She felt the cold lube drizzled in her asscrack, then he lined himself up and took her hole again. It barely even hurt since he used her ass so often. She sighed as he took hold of her hips and started to roughly pump his cock in her guts; she immediately knew she would not be cumming this morning.
Castle rode her hard and fast from behind, his rigid morning hardon like a metal spike in her guts. The sound of slapping hips and her grunts filled the room as he used her, and finally he grabbed both of her generous tits and rode her down until she was laying on her stomach as Castle roughly crushed her tits and drove his cock as far in her ass as he could reach. She could feel his cum, like a warm enema flowing into her and marking her once again as his.
Afterward, they cuddled. Time had gradually changed their relationship from her serving him in exchange for his detective work looking for her runaway daughter. They were much closer to a real couple these days. Though the sex was always the way he liked it, when they weren't fucking Castle treated her pretty well. As they cuddled, she told him about her sister, and Castle asked a few questions about her. She realized their situation was going to change as she felt Castle's cock start to harden against her leg as she described her sister.
***
After a day of researching a case in his office, Castle met Kim that evening. Tina slept all day, but when she woke up she texted Castle instead of going over to empty his balls before she went to work like usual. Since he lived next door, within a few minutes he was knocking on Tina's door. They had a nice chat and Tina made them dinner before she left. Kim looked much like her sister but was more feminine, wore more makeup, and had wavy brown hair slightly below shoulder length. Tina could see the predatory glint in Castle's eye, and she couldn't decide how she felt about Castle fucking her sister, who she had always hated a little.
She didn't even notice when Castle slipped the rohypnol in Kim's wine.
***
It wasn't a large dose. Castle wanted Kim to feel like she had decided to fuck him, but not know she was drugged. He just wanted her very open to suggestion. After a while, he suggested they walk over to his place, and she agreed.
About 30 minutes after Tina left, Kim was choking on Castle's cock. He found it a bit funny that both he and Tina knew Kim was getting fucked tonight without him saying a word about it; just the glances they shared were enough. He was a bit surprised Tina didn't mind if he fucked Kim, but he didn't care enough to dwell on it.
He figured Kim had never sucked a cock that had been in her ass or she would have recognized the flavor of her sister's asshole from their morning fuck, but, then again, she was drugged.
As she gave him a pretty competent blowjob, he considered how far to take her. He couldn't decide whether to break her in easy or to push her hard. She gagged quite a bit on his cock, so obviously her husband hadn't had much of a cock. Castle didn't want her to puke, but he kept and hand on her head and kept his long cock right at the edge of her throat. She'd gag a little, but not enough for it really register in her drugged mind.
Castle kept her at it for a long time. She was wonderfully compliant and kept working his cock until he was ready for more. Castle laid Kim on her back and lifted and spread her legs. He looked her in the eye as he fed his fat cock into her, and they both winced at how tight she was. The next few minutes were a bit awkward, with Castle tearing her pussy open and having a great time, and Kim flinching and making faces that showed the pain of having her pussy roughly stretched. Castle gradually fed her his whole cock which was obviously fatter and longer than she had previously taken, and her body adjusted as Castle reached virgin areas in her young cunt.
A few minutes later, the sounds of fucking filled the room. Kim was more vocal than her sister and made strange noises as Castle tore into her. He kept her laying on her back and gradually worked up a good rhythm. He leaned down and kissed her, roughly taking a handful of her brown hair and then taking ownership of her mouth as her pussy learned to accommodate him. Her tits were slightly larger than Tina's and he slurped and suckled on them like a baby as he emptied his first ball load of the night deep into Kim's pussy. He didn't hold back, there was no point. He had all night with her. Really, thanks to the rohypnol he had as long as he wanted until Tina started to get jealous or mad.
After he came, he lay there sweaty on top of Kim and gently pumped his slightly soft cock in her hole. He could feel his jizz squishing around in her around his cock, and almost immediately he felt it dripping down his balls. He realized he must have come quite a bit in her as he felt it getting pumped back out. The thought of filling her with a huge load of his cum helped him get hard again, and within a few minutes he was back to full gallup, riding Kim roughly and sucking on her face and neck as he pulled her hair with one hand roughly mauled her tit with the other. He thought about changing positions, but decided he was having too good of a time and there was all the time in the world for variation. So after a nice, long, rough fuck, Castle sucked another hickey onto Kim's tit as he groaned and came in her again.
***
After a short nap, Castle woke with a rock hard cock. It took him a second to get his bearings, but he realized that Kim smelled enough like Tina that the olfactory center in his brain linked her smell with the kind of rough sex he got from Tina every day.
She was dozing next to him just where he left her, legs splayed and a puddle of drying cum on the sheets underneath her where it had leaked from her slightly gaping pussy. He enjoyed surveying the damage he had done, though it wasn't bad at all. Her hair was a mess, her tits were covered in light bruises from his hands and hickeys from his mouth. She had a few hickeys on her neck, and she still had a bit of smeared lipstick on her face. He decided that overall a very tasty piece of meat had fallen onto his plate.
Deciding it was time for a change of pace, he grabbed the lube he kept on his nightstand and realized it was almost empty. He went through a lot of it with all the buttfucking he and Tina did, but he was pretty sure he had another bottle in the drawer.
He lubed his furiously hard cock as he stared at his sleeping prey, then gently rolled her to her stomach, spread her legs, and started pushing his cock into her pussy. He noted with satisfaction that it wasn't nearly as tight as their first fuck. She started to rouse a bit as he squeezed into her (he really hadn't given her very much rohypnol), and he slapped her ass gently to help the process. He could feel her fucking back a bit as he retook her pussy, and after a few seconds of just enjoying the moment, he hiked himself up a bit to free his hand and started working his thumb into her asshole. His thumb had lube on it from his cock, but her hole was just as tight as he expected. His cock twitched in her pussy as he thought how good it was going to feel to pop her asscherry.
After a while of fucking her with his cock in her pussy and first his thumb and then his fingers in her asshole, he knew she was ready to lose her last virginity. She awake enough to groan and fuck back against him a bit, and when he pulled it out she moaned gently in disappointment. He lined himself up and started to push into her most private hole, and she made a series of gradually intensifying grunts until the head popped in. Castle knew it hurt a bit, and she tried to scoot away, but he held her hips to keep her in place with his cock just inside the entry to her bowels. He just basked in the moment, trying to memorize the feeling of the pretty girl's asshole strangling his cock as she weakly fought to get it back out. He was very pleased that, before he started fucking her, he remembered to start the cameras he had setup in his room. This video was going to be a personal fav, no doubt about that. He fucked a lot of young girls, but this almost felt like taking Tina for the first time again, and the weird sense of deja vu made it a very memorable fuck.
After maybe 30 seconds, Kim started to get used to having a cock in her new fuckhole, and Castle started to gently push deeper and take a little bit more of her anal virginity. She renewed her struggling as he pushed deeper into her, but it was weaker this time and Castle could tell she wasn't really going anywhere. He held onto her hips and tried to stay at his current depth to prolong his enjoyment of opening her asshole. Finally she settled down, and Castle slowly took another inch from her. He let her wiggle around and basked in the enjoyment of how it felt when she pumped her hips to try and expel him but actually just stroked his cock.
This process went on for as long as Castle could prolong it. He would push just a bit more in, and she would wiggle around. Finally though, his inexorable progress into her guts culminated and his groin was pressed against her asschecks. He had already cum twice tonight, but prolonging the insertion so long had brought him to the edge of cumming again. Castle had never taken so much time to break in a women's hole, and he had to admit it had been incredible.
He knew the rohypnol had worn off some, and she was sweating and panting loudly as they basked in the sensation of her recently virgin asshole wrapped tightly around the base of his cock. She was still laying on her stomach, and he gently leaned forward and sweetly kissed her neck and tongued her ear a bit as he let her get used to having a man so deep in her new fuckhole.
Slowly and gently he started to pull out just a bit and then feed it back into her. He gradually lengthened his stroke until most of his him was outside her when he stroked out, then he slowly filled her guts back up with his rigid cock. She made funny little noises as he slowly worked up the pace, and again he tried to prolong his pleasure as long as possible. The sense of deja vu was overpowering; from behind she looked very much like Tina, and she certainly smelled like Tina, but Tina's asshole hadn't been this tight for years. They gradually worked up to a pretty good pace, with Kim gently grunting on every instroke and Castle occasionally groaning in pleasure as her taught her a new way to please a man.
Finally, he grabbed her hips and allowed himself to ride her and she grunted and wiggled around in discomfort. In Castle's opinion, one of the great pleasures in life was to push deep into a woman's guts and cum. Sure, jizzing on their face or in their pussy was great. Of course it was. Deep in their throat was even better but usually tricky to pull off unless the gal was a whore. But there was nothing like staking a claim to the deepest and most private place you could physically reach inside a woman's body. So he rode Kim to an explosive and shuddering cum deep inside her. Both of them panting and sweaty, he rolled her on her side and laid down behind her with his cock still in her. After catching his breath and letting his cum soak into her body for a few minutes, he slowly pulled his cock out of her new fuckhole and stood up.
He pecked her on the cheek and said "I'm gonna get us a drink, you are wearing me out!" The rohypnol guaranteed she'd have jumbled memories of the evening, but hopefully she'd remember his overall kind and gentle demeanor and think the encounter was consensual. He poured both of them a glass of iced tea, put a smaller dose of ground up rohypnol in hers, and grabbed a viagra from a pill bottle in the cabinet.
He walked back in the bedroom, handed her the drink, said, "here baby, my god you are incredible!" with a gentle kiss on her lips, and then watched her take big gulps of the drugged tea. He figured he'd wait about 15 minutes and then take the viagra, that way both of their medications would kick in around the same time.
***
Early the next morning, when Tina got home, she texted Castle. Normally she would have gone over to suck him off, but she saw that her sister was missing and suspected Kim was at Castle's place.
"Should I come over?"
His reply took a few seconds because he was still asleep. After he cleared his mind, he decided to push Tina's buttons a bit to see how she reacted.
"No, Kim drained me dry. I think my balls are flat."
After a short pause, "I figured since she wasn't here."
Twisting the knife, "I can't believe how tight she was. Her asshole was cherry."
Longer pause, "She always was a goody, goody."
Castle snapped a quick pic and sent it.
Tina opened the pic. It was taken from the foot of the bed and showed Kim sleeping naked and face down with one leg stretched toward the headboard, giving a excellent view of her crotch. Both her holes were swollen and gaping slightly. There were light bruises on her ass as well.
Tina replied, "I'm sure you are the biggest cock she's had, hopefully you weren't too rough with her."
Castle smiled. He knew that for whatever reason Tina sort of liked the fact that Castle was abusing her sister.
"I was a perfect gentleman, except maybe for when I pissed on her, but I don't think she'll remember that anyway. She even came once. Get some sleep, we'll see you for dinner." Tina felt a twinge of jealousy that Castle made Kim cum.
Immediately Castle decided to take the day off. Being self-employed really came in handy sometimes.
Castle surveyed the damage to his sheets early the next morning as dawn spread her gentle fingers thru his window blinds. The midsection of the bed seemed to covered in their fluids from one side to the other. Mostly his fluids he supposed. He had fucked her two more times, which surprised him. He hadn't fucked five times in one night for many years. Part of her appeal was her newness, and part of it was because she was Tina's sister. After he took his viagra and her rohypnol kicked in, he took her in the rougher manner he preferred, fucking her in any hole or position that appealed to him. She wouldn't remember, but she had some new experiences, such as having a cock move back and forth between her pussy and asshole and sucking on a cock that had just been deep in her bowels. She even spent some time rimming Castle, but she was pretty out of it so she didn't do a very good job. Finally, he bent her over and rotated between he holes until he spun her around and came on her face. After he came, he felt a familiar sensation and decided to have a bit more fun so he pissed a little on Kim's lovely fat tits. Not much, he didn't want to change his sheets in the middle of the night (thank god for rubber undersheets), but just enough to mark her. She didn't seem to really notice and just laid there panting from their fuck.
After a short break, he towelled the piss off her, lubed his still hard viagra-fueled cock, and pulled her on top of him. The rohypnol had worn off a bit, just enough that she was moving around a bit. So he put her to work riding his cock. He laid back and gave her occasional encouragement. She obviously hadn't been on top much, but Castle gave her plenty of time to practice and she found her rhythm and obviously started to get into the feel of his fat slippery cock in her stretched hole. For the most part, he just laid back and let her work, and she gradually got excited enough to start biting his neck and groaning in his ear. She got both of them worked up enough to cum, but Castle thought they both needed a push so he slid two fingers in her asshole. The last two fucks had given her butt quite a workout, and his fingers slid into her still lubed and gaping hole with almost no resistance. The sensation of Castle fingers pumping in her sensitive hole while she rode his fat cock pushed her over the edge, and as she came for the first time that night Castle emptied his balls deep in her clasping pussy. After that, they both slept.
After his morning piss, he stood in the morning sun remembering and noticed she still had flakes of cum on her pretty face.
Castle made a simple breakfast for them both, lacing her scrambled eggs with a slightly lower dose of rohypnol from last night. He wanted he relaxed and happy, not heavily drugged.
He woke her with a peck on the cheek and brought her breakfast in bed. She clearly remembered enough to be embarrassed, but accepted the breakfast as a kind gesture. She realized she was hungry and wolfed down the drug laced eggs.
Afterward, he talked her into a shower together where, after the drug started to kick in, he maneuvered her into a very pleasant standing fuck. He knew she'd be sore so he lubed up with the bottle he kept in the shower, but she still winced as he retook her pussy. However, fairly quickly she started moving her hips and fucking him back a bit. He chewed on her ear as he unloaded in her pussy, and after a few seconds to recover he pulled out and they resumed their shower. He made sure to soap up her tits and chest, not only because soapy tits feel great in your hand and it was another way to take possession of her body, but also because he might want to suck on her fat tits later and he wanted to make sure he washed his piss off her chest.
After they toweled off, Castle smirked as he gave her a short and sheer nighty and thong panties that belonged to Tina, and he enjoyed the show as the lovely young woman slid the panties up her long legs. She seemed uncomfortable with the thong string in her asscrack, but her addled mind couldn't process what was happening and Castle handed her the nighty to distract her, which worked perfectly. Being lightly drugged, Kim didn't even wonder why he had the women's clothes in his apartment and why they fit her perfectly, although the nighty was a bit tight across her chest. He set her on the couch in front of the tv and stripped the bed so he could take them down to the apartment building's wash room. He put the spare set of sheets on the bed.
After an hour of flipping channels on the couch with Kim, Castle found himself ready for another taste of Kim. He pulled his now hard cock out of his boxers and gently pushed her head down toward it. Her drugged mind accepted his guidance and within a couple of seconds she was again slurping on his cock. He sat back and started flipping channels again as she sucked.
***
Castle ended up taking off the rest of the week. He spent all day breaking Kim's holes to his cock and teaching her to please him, then he fucked her at night once or twice when he woke up with a hard cock. He kept her just drugged enough to be compliant, but he gradually lowered her dose until she was just getting valium in her meals to keep her relaxed.
Meanwhile, Tina was missing Castle far more than she expected. She had thought a break from being buttfucked two or three times a day would be wonderful, but after a couple of days her asshole started gently itching. Since she couldn't feel her pussy or clit, her ass has her main erogenous zone and daily use for a couple of years had acclimated her body to regular sexual stimulation in her asshole. On day three, she broke out her old dildo. It was from her lesbian days, so it smaller than Castle and didn't fully scratch the itch, but it did help. On day four, she brought home a girl from the local gay bar, but the girl tried to eat her numbed pussy and didn't understand how to get her off. Also, after years of being dominated by Castle, it was simply uncomfortable to have gentle feminine sex rather than being roughly used and pounded by a fat cock. She found herself starting to get very jealous of Kim.
***
On Friday evening, after five days of not getting fucked, Tina knocked on Castle's door. He looked through the peephole, then opened it. He was wearing a pair of boxers and t-shirt, and Kim was sitting on a barstool wearing one of the revealing night gowns Castle made Tina wear when she slept over. The slightly vacant look on her face showed that Kim was obviously a bit drugged, so Tina simply asked Castle to talk to him privately. They went in the bedroom and closed the door.
Tina asked, "Have you been having fun?"
He chuckled, "She started off so tight I can't believe it. She's a lot more... accommodating now. Have you been enjoying your break?"
"Actually, I... I miss you."
Castle looked a bit surprised and said, "Really? I thought you'd be happy to have some time to eat pussy again."
"It's just not the same anymore. I... need you."
After a couple of seconds, Castle simply smiled and pulled his now hard cock out of his boxers. Tina paused for a heartbeat, then with a tear rolling down her cheek she knelt and started sucking him off. Wanting to make him happy and semiconsciously competing with her sister, she put her all into it and was gagging on his cock almost immediately. As she forced his fat cock into her throat, Castle closed his eyes and let her work.
She skull-fucked herself onto Castle for several minutes, pushing herself as far as she could to please him. Finally, she had drool all over her diner waitress dress and had built up to a nice pace of fucking her throat on and off of Castle's fat cock in the hope that she could get him hot enough to fuck her.
Finally, she pulled back and stroked his cock and said, "Will you please shove this fat cock in my ass? I.. I miss it." She was trying to seduce him, but hated herself a bit for it.
Castle gently guided her up and kissed her lips, then turned her towards the door which she braced her hands on. Then he hiked her skirt up, and pulled her thong to the side.
She stood there, fully clothed and pushing her ass out and gently moving it back and forth as an invitation while Castle lubed his cock with the new bottle he'd starting using a couple of days back.
He moved in and stroked his cock in her crack a couple of times, then had a weird idea and pushed his cock into her pussy. As far as Castle knew, nothing had been in her pussy for a couple of years now, and he could tell because it was pretty tight. He groaned in pleasure as he slid in, and she groaned in disappointment because she could vaguely feel what he was doing but it brought her almost no pleasure at all. He set up a nice rhythm pumping her numb hole, and finally she said, "Please, please... I need to feel you in my ass."
Castle kept fucking her pussy. Not long, but just long enough to make her think maybe she'd get no relief despite her humiliating display.
"This feels so good baby. Your pussy tightened back up. I might need to fuck this tight pussy more." He said this knowing that it would be another way to take his pleasure from her while only giving her frustration.
Then he said, "But I know what you want" and he pulled out, rubbed it on her main fuck hole to lube it a bit, then gently started working his cock into her ass.
She groaned in a mixture of pleasure and pain as he slowly opened her, wanting to cause a bit of discomfort to remind her the cost of her limited pleasure. Finally he popped inside and a few seconds later started gently pumping.
"The funny thing about getting buttfucked as much as you have, is your ass never really tightens back up. I guess it might if you stop for months, but even after weeks, a well broken in asshole starts off tight but opens back up quickly." To punctuate his explanation, he started pumping his hips, and Tina found that the discomfort was gone and all she felt were equal parts pleasure and self disgust as she rutted her asshole against Castle's fat cock to draw more of him in.
They settled in for a nice, long, rough buttfuck. She was grunting loudly as Castle stroked himself in her asshole, and at some point the bedroom door started banging in the frame from the enthusiasm of their fuck. Castle rode her hard and rough, slapping her ass and yanking her hair when it suited him, and each abuse sent sparks pleasure through Tina. Castle had already fucked her sister twice that day, so it took him a long time to cum. She could feel him building to his climax as he got progressively rougher, and right when she thought he was about to come, she shocked herself and had a brutally powerful and humiliating anal orgasm, the first she ever had. As she twitched and lost bodily control from her explosive climax, Castle pulled out of her ass, pushed her to her knees and shot his cum on her face. As she fell against the door gasping from the first orgasm she had in almost two years, Castle felt deep satisfaction, and after a few seconds started pissing on her while she basked in the afterglow.
When he was done, he shook the last few urine drops off on her and put his cock away, then said, "I guess you really needed that!" and chuckled as she limply moved out of the way so he could open the door. As he walked through the door, he said, "clean that piss up before you leave", and after a few seconds, Tina got up to get a towel from the bathroom.
Kim had moved to the couch and was watching tv. She showed no sign that she realized what just happened in the bedroom, and whether she was too drugged to notice or too embarrassed to bring it up, Castle was felt no need to talk to her about it.
***
About five days later, Castle slightly increased Kim's dose of valium, and he made Tina take a similar dose. With Tina, it was fun because instead of sneaking it into her food or drink, he simply handed it to her and said, "take this". She looked at him for a long second, then obeyed. Her asshole was itching again, and if she had to drug herself to get it scratched, she was willing.
Not long later, Castle was sitting on Tina's couch as Kim knelt between his legs dazedly sucking him off. Tina watched from the nearby recliner. She was uncomfortable, but the drugs took the edge off and she was gently writhing her hips in the chair hoping the display would somehow end up with Castle fucking her itchy asshole. The girls had done their makeup together and put on matching pink thongs, so they almost looked like twins. After Kim had him nice and hard and Tina was obviously worked up to a fever pitch, he stood and motioned for Tina to join them. First, he pulled Tina to his face and they kissed while her sister nursed on his fat cock. After they made out a little, he gently pushed Tina down to her knees. For a second she looked up at him, finally understanding that he was going to use them terribly tonight. Then, her drugged mind gave up processing and she leaned in to help her sister suck his cock.
At first, he had one sister work his cock while the other sucked his balls. After a while, he pulled both sisters to work his cock at the same time, one on each side, or one at the tip and one on his shaft. The effect of having two Tinas, the woman who had brought him so much pleasure, working his cock at the same time was incredible.
He finally had Kim climb on his lap facing him, and then she fed his cock in her now much looser pussy. Kim immediately gasped in pleasure and started fucking herself on Castle as Tina sat back watching her sister. She was again struck with jealousy watching Kim groan and enjoy Castle's fat cock in her pussy, a hole that no longer gave Tina any pleasure. As she thought about it, Tina found herself becoming intensely jealous because, while she had cum once in two years, she was pretty sure Kim came shortly after Castle slid into her and who knows how many times she had come in the last week and a half.
Finally, as Castle laid back and let Kim stroke his cock with her pussy, Tina heard Castle growl, "Tina, I suggest you get your mouth to work if you want to get fucked."
With just a bit of hesitation, she leaned over and started mouthing his balls while Kim rode his cock. Having her sister's pussy pumping Castle's cock a few inches from her face made her uncomfortable, but the valium and her itchy asshole drove her past her concerns and she tried to please Castle. After a few minutes, when he said, "suck the base of my cock," it didn't seem like much of a move so she started gently sucking the part of his cock not currently sinking into her sister. She was so close she could smell her sister's pussy. When Castle simply said, "Lick higher", Tina had a moment of clarity and knew what Castle had planned. She paused there, still sucking the base of his cock and trying to process her revelation until he said, "LICK HIGHER" and Tina moved her mouth up to the part of Castle's cock currently pumping into her sister. She tasted her sister, and almost immediately her sister humped down and her pussy lips grazed Tina's lips.
Tina simply couldn't process what was happening. She was a lesbian who had pussy lips brushing against her face, but the pussy lips belonged to her sister and were currently wrapped around Tina's boyfriend's cock. The same cock that only fucked her asshole. The same cock she didn't even want to fuck her pussy. The same cock that almost never made her cum, but that filled her so often she craved it.
Castle groaned as Tina performed the obscene act, and laid back to enjoy the depravity of the situation. He let her lick up her sister's pussy juice off
his cock for several minutes until he could tell Kim was going to come. When Kim got to the brink, he pulled her asscheeks apart and said, "put your tongue in her ass while she comes." Kim looked him straight in the eye as her sister pushed her tongue in as far as she could, then Kim closed her eyes and had a violent orgasm on his cock and her sister's well trained tongue.
When Kim's orgasm was mostly over, Castle roughly pushed her to the side where she sat on the ground to catch her breath, then he fed his slimy cock into Tina's mouth. She almost mindlessly sucked her sister's cuntjuice off his cock, lost in the moment and just hoping to be satisfied.
After she had licked and sucked him clean, Castle sat back on the couch, spread his legs, and wordlessly handed her the lube he kept at the end of her couch. She knew what to do. She teased him a bit while lubing him up, spreading it around while she tongued his balls and occasionally his asshole. At some point, Kim recovered from her orgasm and Castle pulled her up to make out with him while Tina got him ready to scratch her itch. Finally, Tina couldn't wait any more. She turned to face away from him, climbed over his cock, and slowly worked it into her fuckhole. Her ass was so used to his cock that there was just a bit of initial discomfort, then it felt like a part of her body was back where it should be.
For a while, they kept at it, Tina scratching her deep itch with Castle's fat cock, and Kim romantically making out with her new boyfriend, the one who had introduced her to so many new pleasures. Tina got more and more into it until the sound of her ass slapping against Castle's lap filled the room with only her occasional grunt or groan to accompany it.
After a while, Tina was starting to get tired but didn't want to stop when she heard Castle whispering to Kim. Tina's innocent little sister got off the couch, and carefully avoided Tina's eyes and she kneeled down between the legs. She then leaned in and started lick Castle's balls as Tina pumped her loose asshole on his cock. After a few minutes of tonguing his balls, Kim moved up to suck the base of his cock. Tina realized that Castle must have told Kim exactly when he expected, and like the good little drugged fuck toy Castle had made her, Kim was obeying.
When Kim started sucking the base of his cock, Tina's empty pussy started occasionally touching her sister's face. Tina could feel the contact in a tingly and numb sort of way, and the incredible depravity of the situation ramped up her excitement. She leaned back to more easily fuck herself on Castle's cock and knew she was getting close to cumming for the second time in two years. Tina almost pissed herself when her sister pushed her face in Tina's pussy and started eating and slurping on her.
Kim didn't know that Tina could just barely feel it, but the insane filthiness of the act drove Tina over the edge and she came, trembling and spastic, on Castle's cock in her ass.
When she was done, Castle pushed her off him and she collapsed on ground immediately feeling the emptiness in her ass, and Tina was barely aware as Castle fed the cock that had just been deep in her bowels into her little sister's mouth. Kim slurped on it loudly until Castle jacked off on her face then used his cock to push the cum into her mouth so she could swallow it.
When he collapsed on the couch, Kim followed him and kept nursing on his cock while he recovered. After several minutes when he was hard again, Kim climbed on him again and slid her pussy down. After a few pumps, he said, "Other hole, baby" and his new girlfriend lifted herself off his cock, repositioned, then slid him into her other fuckhole. Tina realized her sister's asshole had gotten pretty loose from regular fucking, because without pause she went back to stroking Castle's cock, but this time with her guts rather than her pussy.
After a few minutes of Kim buttfucking herself onto Castle's cock, he slapped her ass and said "turn around and face the other way."
After Kim turned and slid him back into her butt, Castle pulled her back so she was laying on his chest, still wiggling her hips on his cock. Tina knew what was coming as she watched her sister's full tits gently roll around, so when Castle said, "suck my balls" she didn't have to be told twice.
Tina started at his balls and even tongued his asshole a bit, which drew a groan from Castle. Then she started working her way up his cock, as she knew he expected. After a few minutes, she was slurping on the lower half of his cock as her sister pulled her rectum on and off of it. She could smell and taste her sister's pussy and ass on him. Finally, knowing what was expected, Tina pushed her face in her sister's pussy. Unlike her sister, Tina was an experienced pussy eater. Of course, it wouldn't have mattered if Kim ate good pussy because Tina couldn't feel it, but Tina ate great pussy and Kim could definitely feel it.
Very quickly the fuck devolved into Kim writhing around on Castle's cock in her ass as her sister ate her to orgasm after orgasm. Tina started sliding fingers in Kim's pussy, which pushed Kim even higher, finally getting most of her hand into her sister's formerly tight pussy. Based on her sister's goody two shoes past, Tina was certain that two weeks ago she would have struggled to get three fingers in, but now she was pretty sure she could fist Kim if Castle's big cock wasn't in her asshole. Finally Kim just kind of shut down from too many orgasms, and Castle pushed her off him. She laid panting and limp on the couch next to him as Tina moved in to take her reward. She climbed on Castle's lap, looked him right in the eye, and gently bit her lip as she slid her asshole down around his cock.
They started that way, with Tina riding him, but they shortly moved to the floor and Castle got behind her and roughly fucked her like a dog until he came in her asshole. Tina didn't come this time, but it had been so long since Castle came in her ass that feeling his warmth inside her was almost as good.
As they lay there basking in the afterglow, Tina felt cum slowly leaking from her gaping asshole and she licked her lips and tasted her sister. She suddenly realized that Kim had to go or she might lose Castle.
***
Castle kept them drugged for the next couple of days. Tina was off work and Castle planned to have some serious fun.
In the middle of the night, Tina woke up to Castle buttfucking her sister again. She just laid there and listened as he jerked himself off using her grunting sister's asshole and then came in her. Then Tina watched as Castle took Kim into the bathroom and had her sit on the toilet and piss while Castle emptied his bladder on her tits and belly. Most of his piss ran down Kim's torso and mixed with her piss as it fell in the toilet. Castle must have pissed on her quite a bit during their time together, because Kim smiled up at him when they finished and sucked the last few drops straight from his cock. Tina felt tears of frustration as she realized how close she was to losing Castle.
***
The next morning, Tina took the initiative and woke Castle up with a blowjob. He then rolled between her legs and fucked her numb pussy a little while she gently begged him to fuck her other hole, and then he finally flipped her over and very roughly smashed in her asshole. Kim just laid there and watched as Castle brutalized Tina, and Tina again got frustratingly close to coming but didn't make it before Castle filled her asshole with cum. When he pulled out, Tina sucked him clean without hesitation, almost hoping he would get hard and fuck her again. He ultimately pushed her away and told her to make them breakfast while he showered with Kim.
Tina obeyed while listening to giggles form the bathroom. Finally, they came out and sat down to breakfast, and this time Castle handed them each a quarter of a rohypnol to take. They didn't know exactly what it was, but they knew he was drugging them. The sisters looked at each other and Castle, then dutifully took their pills. After breakfast, Castle gave them a few minutes for the pills to kick in, and then told them what to do.
***
Everyone was naked. Castle was on the couch stroking himself watching the sisters, who were currently sixty-nining on floor in front of Tina's couch. Of course, Tina could barely feel as Kim ate her pussy, but Kim didn't know that. Tina had gotten Kim off twice and Kim was trying futilely to even the score. Castle felt intoxicated as he watched the two very similar looking sisters performing the incestuous act, and he was thinking his cock might explode soon if he didn't get it into one them.
He waited as long as he could, finding himself drawn to watching Kim's now fucked out and slightly gaping asshole twitch as her sister made her come again. Finally, he lubed himself up and moved behind Kim. He slid his cock between Kim's cunt lips and Tina's face a few times, noticing the Tina's face was soaked with her sister's pussy juice, then he lined up with Kim's asshole and slid inside. She froze for just a second as she acclimated, then dove back into eating her sister's pussy. Castle smiled when he heard Tina groan in frustration as the cock she wanted slid back into her sister again. Castle settled in for nice rough buttfuck as Tina kept sucking her sister's pussy and clit. Pretty soon, the combination of Castle's pounding cock and Tina's sucking mouth had Kim gasping in pleasure, and Kim came in a clenching orgasm that sucked the load out of Castle's cock into her guts. When Castle pulled out, he let his slimy cock fall on Tina's face and she immediately sucked it in her mouth. Meanwhile Castle took hold of Kim's neck and lifted her back toward him so he could kiss her neck in post coital bliss. The cum he sprayed in Kim's guts immediately started leaking out and as he kissed on Kim's neck he felt Tina push his cock to the side, lock her lips on her sister's asshole to suck out the fresh load he had just shot there.
***
"I need to talk to you."
They had just finished a morning threesome where Tina finally got her whole hand in Kim's pussy. Castle laughed as she did it, remembering how tight Kim had been a month ago when he first fucked her. He jerked off and came on Kim while Tina fisted her and sucked her clit, then he told Tina to make her cum. He pissed on Kim's tits and belly as she came. Kim was in the shower washing his piss off.
"What about?"
"Kim can't stay here. It's too... complicated. I miss you." In the last month, Tina had only been fucked a handful of times, and she had grown to absolutely hate watching her sister's now slutty pussy come over and over on Castle while Tina was very lucky if she got close to an orgasm in her asshole. She'd only had two anal orgasms so far, and she desperately wanted to have another. The more Castle fucked her sister, the less likely she was to cum.
Castle had known this moment was coming. Tina was obviously struggling with the lack of attention from Castle, and in the last couple of days he had become concerned that she would give up on him. He liked fucking Kim but she enjoyed it just a bit too much. She didn't offer the same level of kink as his anal-only lesbian girlfriend. But he hadn't been sure what to do, and it never occurred to him that Tina might be his ally in this situation.
"Honestly, baby, I've been thinking the same thing. I'm just not sure what to do. I don't want to just kick her out, and you wouldn't like the way I normally solve situations like this." Tina didn't know much at all about Castle's actual work, but she had long ago figured out that it had something to do with human trafficking. She had tasted blood on Castle's cock too many times for it to a coincidence, and every time Castle and his friend Lamont had fucked her, she felt like Lamont was evaluating her. She was pretty sure he was a pimp.
"Could you find her a boyfriend or something?"
"Most of the guys I know don't have girlfriends, they have female employees if you know what I mean." He leaned over and gently kissed her and said, "don't give up on me, I'll figure something out." It made it easier for Castle knowing that Tina would be ok with anything short of her sister being whored out. He just had to come up with a creative solution.
***
Kim was gone three days later. The solution came to Castle as an epiphany, and after a few phone calls it was done. Tina was still sleeping after working all night when he handed Kim a full rohypnol pill and watched her dutifully swallow it. Then as they waited for the pill to kick in, he lubed himself, bent her over, and rode her through one last rough fuck. He switched between her holes when the urge struck him, and she pushed back and rode him no matter where he chose to fuck her. It was clear to Castle that Kim was a bit of a nympho now. Unlike Tina the lesbian, Kim liked cock even before he met her, she was just a prude. So, she broke like water when he turned her out. As he fed his cock in her loose asshole, she pushed back and wriggled around and then started pumping back and forth as he rode her. She squealed when he slapped her ass and grabbed her throat. He gently squeezed her throat just enough to make it hard for her to breathe as he stroked in her asshole. He remembered all the fucked up stuff he had her and Tina do, and those memories ultimately pushed him over the edge. He pulled out and emptied his balls in her mouth while re-living some highlights from their month together. She swallowed it down without a thought and sucked the last few drops from his cock, and when he gently held her head in place as his cock softened, she knew what was next and waited. She gulped his piss just like she drank his cum, and after his bladder was empty and she'd sucked down the last few drops, she licked his cock clean and put it away for him.
After she brushed her teeth, he dressed her up in one of Tina's nighties and g-string panties, which was almost all she had worn for over a month. Then he walked her down to the garage, loaded her in his car, and started driving. Her drugged mind couldn't form questions, so they rode in silence. The mansion in Beverly Hills was enormous. The gate opened as he pulled up, and he drove through and up the long driveway. When he pulled up to the house and shut the car off, a man and woman in their 50s came out. They reeked of money, which wasn't surprising since he was a real estate mogul and she was his very expensive wife. She was older than most rich men's wives, but she made up for it by being legendarily perverse. The couple was well known in some circles for the depraved parties they threw.
While Castle shook Clive's hand, Stephanie excitedly walked around and got Kim out of the car.
"My dear, you really are lovely!"
Kim woodenly climbed out of the car and stood there in full daylight in Tina's tight, sheer nightgown with her tits about to pop out and her thong easily visible beneath it.
Clive said, "Very nice. We've been looking for a house girl for a while. We considered buying a thai girl because they are so cheap and tiny and cute, but getting her in the country seemed like more trouble than it was worth."
Stephanie examined the girl like merchandise, moving around her pinching and squeezing. She finally reached her hand under the Kim's short gown, pushed the thong to the side and slid her fingers into Kim's pussy.
"She's definitely been fucked quite a bit!" she giggled. She dug another finger in and seemed to be trying to fist Kim in the middle of their driveway.
"Don't worry about them, come with me I'll get a drink and give you your cash."
As he turned to go inside, he saw Stephanie bend Kim over the hood of the car, then spit on her hand and slide it back into Kim. As he walked through the door he heard Kim grunt loudly and wondered which of Kim's holes Stephanie had pushed her hand into.
He used the bathroom and then had a drink with Clive while he counted the money. When he left, he didn't see the ladies but heard what sounded like Stephanie moaning from the closed bathroom door, which made him smile. Based on what he'd heard about Stephanie, he suspected that Kim had just swallowed another bladder-full of piss and was licking her new owner clean.
***
When Tina woke up that evening, Castle was in her living room waiting for her. He didn't say a word, just pulled her close to kiss him a bit, then pushed her on her knees to suck him off. When he was hard, he bent her over the couch and roughly sodomized her. The sex was rougher than usual, and she actually began to cry a bit from the slapping and hair pulling. When he finally came, he pushed deep in her hole and emptied his balls, then pulled out after he caught his breath so she could lick him clean. Tina nursed on his cock crying more freely now because she realized she had him back full time, but she also realized that she had allowed her horniness to make her forget how brutal he could be. After a few seconds Castle started to piss in her mouth, and Tina drank it down without hesitation just like she had seen her sister do. They hadn't done much piss play before Kim arrived, but Tina was happy to defile herself further if it meant she got Castle back.
That night at work, for the first time in over a month, Tina had to change her underwear because Castle was leaking out of her throbbing asshole again.
Tina and Castle never discussed what happened to Kim. Castle figured she was scared to ask, and he enjoyed Tina not knowing. Meanwhile, he did see Kim from time to time. He went to a few sex parties at the Jones', and every time Kim was there getting fucked by the guests. She seemed to be a project for Stephanie, who was gradually turning her into a living barbie doll. It was obvious she was on a hardcore exercise regimen, and they dyed her hair blonde and waxed her pubic hair. After a while, they got her large and very fake looking tits, and then they liposuctioned out her waist to give her a more hourglass shape. They transferred the fat from her waist into her ass, so by her second year there Kim was just a walking sex doll. During a later visit, Castle was a bit surprised to the see chastity piercings. They were small bars evenly spaced all the way down her pussy lips making her pussy look as close to Barbie's flat, sealed pussy as a human could easily get. She was still popular with the guests, who enjoyed humiliating her and using her for their pleasure. The rich women seemed to particularly enjoy abusing the beautiful young girl, and she spent most of her time under some rich woman's skirt. She recognized Castle whenever he saw her, but her training was strong enough that they never spoke to each other again.
The last time he saw her, Kim was very, very pregnant. She was in a white, skintight dress and her milk-swollen fake tits and huge belly looked about to burst as she sucked and licked her way around the party. Castle used her asshole later in the night while she was sucking off an elderly guest, and he noticed that her chastity piercings were still in place. When he was ready to cum, she'd finished the old man so Castle turned her around and fed himself into her mouth. She'd gotten very good at deepthroating, so he let her suck the load from his balls while wondering how much cum she had swallowed that night and how her cum diet would affect her baby. Later in the night when everyone was drunk and Kim was upstairs getting throat or buttfucked by anyone who had the urge, Stephanie told Castle that Kim's pregnancy was an accident from one of their parties and they decided to make her keep it. Stephanie was curious to see what the baby looked like, and then Stephanie laughed and said things had gotten a bit out of control one night, which was before Kim's chastity piercings were installed. Clive and Steph had passed out and found Kim the next morning still being fucked by some unsavory looking men who were not invited to the party. They suspected some drug dealers had been called in late in the night and decided to take a piece of free pussy while they were there. Clive and Stephanie thought it was funny, so they let the men fuck Kim until they had their fill, which turned out to be a couple of hours later. Between the drug dealers and guests, they had no idea who the father was. Nine months later, the Jones were excited to see what Kim had growing in her belly. Stephanie joked, "after some of the parties we've had, it's possible she might have a litter of puppies!"
Meanwhile, things with Tina had pretty much gone back to normal, with the only difference being that Tina knew it was possible to cum with her asshole. She had done it twice. But getting fucked multiple times a day lowered her sensitivity again, and she seemed to always find those orgasms just slightly out of her reach. Their sex often ended with Castle cumming in or on her while she trembled in frustration due to the orgasm she almost had. Castle, of course, recognized her frustration and thought it was pretty funny. He figured he would give it some time to let her stew, then maybe every six weeks or so he'd have her abstain from buttsex for a week or so and then fuck her to an orgasm. Of course, he'd make her beg for it and do whatever humiliating things he could come up with to earn it, and she would hate that but it would only make it hotter for both of them. He decided this was going to be a lot of fun.
