He found them about 8 hours after he started looking. It was a pretty common case - wealthy girl in her late teens or early 20s falls for lower class guy, they run away together, and rich family pays him to retrieve her. These case came up about once a month, and two or three times a year he recovered one and he bribed a local reported so there was a news story about Private Investigator Steve Castle recovering another girl. The other 9-10 girls met a different fate.
In this case, the young man was Mexican and they ran for the border. The couple had driven from LA to Tijuana and was overnighting in a decent hotel. They'd gone out for dinner and had returned to the room about 30 mins ago. As he crept up to the room, he heard the creaking of springs and a few little moans. He quietly picked the lock, and then just as the spring-creaking sped up he burst in, ran across the room with a taser in each hand and zapped them both. As the mexican teen laid there twitching with cum dripping from his dick, Castle quickly gave each a shot of sedative. The last thing they saw as their world faded was Castle turning to close the door and then starting to take his pants off.
***
The young Mexican, Luis, woke to the sound of a creaking bed. He shook off the fog from the sedative and tilted his head to see the bed. On it, his girlfriend, Susan, was blindfolded and gagged and was on all fours while a large white man pistoned a fat penis in and out of her asshole. She was grunting in pain and the sound of the man's groin slapping on his girlfriend's ass filled the room. He tried to move and realized he was handcuffed both hands and feet and he was gagged. He was also stripped naked. He rolled around a bit, but ultimately all he could do was lay there and listen to his beaultiful girlfriend's grunts and the maddending sound of slapping flesh. Ultimately, the stress and lingering effects of the sedative got to him and he fell asleep to the sound of her painful grunts.
He woke up a few hours later. After he remembered where he was, he looked around to see his girlfriend laying on the bed with her head hanging over the side as her rapist slowly pushed his long cock all the way down her throat and then just as slowly retraccted it. Luis didn't know, but the man had come in her ass three times already and was now just entertaining himself by stretching her throat out. He'd been at it for maybe 20 mins when Luis woke up, and he would continue until he was bored or, more likely, ready to buttfuck her again. Luis couldn't sleep anymore, so he just laid there and watched the man destroy his girlfriend's beautiful throat.
Just before dawn, right after the man emptied his balls in Susan's asshole after pounding her while slapping her ass and pulling her hair for over an hour, there was a knock at the door. The man pulled his dick out of her ass and opened the door. Luis looked back as Susan who was silently weeping while waiting on all fours, and he noticed that her asshole just hung open and seemed to be permanently stretched by the rapist's huge dick. Three Mexicans came in, and the first one shook hands with their naked rapist. He inspected Susan then Luis, and Luis was shocked when the Mexican asked the rapist if he had fucked Luis yet and then told his men in Spanish to get started. The rapist said he had not fucked Luis, which made the Mexican smile and look at Luis while adjusting his pants. The men pulled out large duffel bags and startged loading Luis and Susan into them. As they were loaded, Luis saw the Mexican give the rapist a stack of cash and heard him say they were going to be placed at a new brothel he was setting up in the nicer part of town. As they were carried out, he was horrified to hear the Mexican say that transsexual whores were getting more and more popular, and that Luis was headed to a special facility in rural Mexico that would feminize him and teach him to please cocks.
***
As Castle drove back to LA, he did the math. Diego (the Mexican pimp) gave him $20k for the couple. The deal with Diego is he gets unlimited use of them for 6 months, and then Castle has the option to buy the girl back. usually it's about $5k to buy the girl unless for some reason she a is a big money maker. He would feed the girl's family scraps of info while stringing them along for the 6 months, then tell them he found her at a whorehouse and needs $10k to buy her back. The boy was never coming home and would be a tranny hooker for the rest of his life. Between the initial $20k and the time he billed the family for over the next 6 months, this would be a lucrative deal. It always was, which is why he sent around 10 couples per year to Diego. Almost all the girls came home 6-12 months later, but Castle didn't advertise these because he though it might be suspicious that he rescused so many girls from whorehouses. A handful of the girls never came home. Most were bought by drug lords to entertain their men or maybe if she was lucky be his mistress, but three of the girls had ended up becoming big stars in the beastiality circuit and were making too much money for Diego fucking dogs and donkeys, so he'd pay Castle to keep them. The last time he'd been to Diego's he'd been blown by a pretty competent Mexican teen while 20 year old Megan Hollister fucked a Great Dane onstage. Former pageant queen Megan had been fucking dogs for two years, but the visible pain on her beautiful face as the dog's softball-sized knot expanded her asshole drove him to push the teen's head down and empty his balls straight down her throat.
***
A week later while sitting in his office, he called Susan's mother and fed her bunch of BS about how he had spent the last week looking. He explained that Susan had definitely made it over the border, and had a hotel reciept to prove it, but that after that the trail went cold. He explained how the rampant corruption and crime made Mexico challenging for PI work, but that he would activate his network and keep looking. Toward the end of the call he got an email from Diego, and started stoking his cock thru his pants as he scanned around 20 pictures of Susan getting fucked. There were mexicans, white college boys, business men, and what were evidently basketball players. As he hung up, he decided he probably should visit Diego soon so he could fuck Susan a few more times before she got too loose. And his dick twitched when he realized it might be fun to get Susan and Megan together so Susan can suck the dog cum out of Megan's ass.
***
Tina was Castle's next door neighbor, and Tina was Castle's "girlfriend". Actually, she was a lesbian and had been since she left her abusive husband 10 years ago. She wasn't butch; she was slender and feminine with a respectible set of tits, but she found that she just couldn't be attracted to men after her husband. Before the divorce they had two kids, a girl and a boy. The boy, Michael, was now 15, and the girl, Melissa, was now 17. Wherever she was.
Tina was not rich. Uneducated, she worked long nights at a diner to pay her bills. After her daughter disappeared two years ago, she had gone to Castle for help. He quickly realized she had no money to pay him, and after some very careful negotiating, she agreed that a blowjob twice a week was a fair payment for his time. That may not seem like much, but to Castle having a lesbian suck him off was a perverse thrill. Watching her struggle to deep throat him never failed to push him over the edge. Castle played her like a violin. After a few weeks of blowjobs, he gave her a few fake clues and told her he thought two blowjobs per week was not worth his time. They renegotiated the deal while she sobbed, and after that he had full access to all her holes three times a week. He went easy on her that first night, and after she sucked him hard, he only fucked her pussy. Her tight lessie pussy and intermittant crying drove him crazy, and he came in a suddering orgasm while chewing her ear, pulling her hair, and squeezing one of her fat tits. He couldn't remember the last time he came so hard. Two days later he popped her anal cherry. That orgasm was even better.
That was about a year ago. Since then, he had gradually changed the boundaries of their relationship. Since they were neighbors, he had her start coming to his place to fuck. After a few weeks of that, her son caught her leaving his place and he was formally introduced as her boyfriend. That was when the gloves came off. The three fucks a week deal was forgotten as he started spending more time at her place, often spending the night. A few months after their re-negotiation, she would gently cry as he was fucking her lesbian ass almost every night. In fact, he would often go days without fucking her pussy, but her ass and mouth were used constantly. He kept feeding occasional fake clues about her daughter, but the truth was that he devoted almost no time to her case. He started buying her clothes that were a bit slutty, and he insisted she wear tiny underwear or none.
Lately they had gotten into a groove where they truly felt like a couple most of the time, but Tina was always ready to use her mouth or ass to please Castle. He always used her before she went to work in the evening, and then often again when she got home. Initially, it was embarassing when Castle, in front of her 15 year old son, pulled her back to their bedroom to fuck her before she left for work. She resisted only a tiny bit, then sucked him hard. When he was ready, she pulled up her diner waitress outfit and bent over so he could roughly sodomize her. After that day, she almost always went to work with cum dripping from her ruined asshole. Then before he went to work in the morning, he usually woke her up for a facefuck. Three years ago the idea of sucking a cock every morning would have revolted her, but now it was simply part of life.
Castle got back to LA from Tijuana at about 10 am. It was hard work being a PI - he was bone tired from being up for almost 24 hours and also pounding Susan's guts for several hours. Michael was at school, so he got a glass of water and then walked into the bedroom. Tina was laying there still sleeping from her night shift. Her back was to the door, and her thong clad ass was hanging out of the blanket. He could clearly see her asshole that he had destroyed over the last year. It was slightly distended and seemed like it wanted to wrap around the thong string that failed to cover it. He stood there and thought about their past as his cock lengthened and he decided he had enough energy for one more butt fuck before he slept.
Tina was groggy as he rolled her on her stomach, pulled her ass up and her thong string to the side, and fed his cock into her asshole. If she wasn't warmed up, there was always initial pain, but constant use had made her asshole very receptive and within a few seconds the pain was gone. While Tina grunted in mild discomfort, Castle settled into a rhythm of deep fucking where he pulled almost all the way out and then went balls deep. The sound of slapping flesh filled the room and Castle user her casually with no regard for her pleasure. He looked down at the pink triangle tattoo on her hip, and felt his dick get even harder as he roughly sodomized her. Over the past few months, the rough sex had started to get to her. Her pussy started to juice up as he used her ass, and when he grabbed her hair and started to really pound her asshole, she felt her pussy start to leak down her leg. She had a weird moment of clarity feeling the tickle of juice from her unused pussy as Castle's big cock smashed in her asshole. She hated that she felt pleasure while being used so casually by a man she didn't even like. She thought back to her last girlfriend and how delicate their lovemaking had been, like two butterflies. It was nothing like the gutteral and brutal anal sex that was her current sex life. With a one hand pulling her hair and the other beating her ass, Castle grunted as he again emptied his balls in her intestines. He collapsed in a sweaty mess as Tina moved her mouth down to clean Castle's cock. She had no idea that she was cleaning both her and Susan's ass slime off his dick, but it wouldn't have mattered anyway. They had fallen into a rhythm where he fucked her and she hated it, but it was comfortable because they had been at it for so long. It was even starting to feel a little bit good even though it repulsed her. She slobbered on his cock, then his balls, then even tongued his asshole like he liked. He started to get hard again, but then started snoring and she curled up next to her boyfriend and slept.
She dreamed about the cute waitress, Charlie, she worked with at the Diner. In her dream, Charlie came onto her and they started making out in the bathroom, but after a few minutes Castle burst in and took over. They were his fucktoys, and he alternated between the Charlie's asshole and Tina's mouth until he pushed it into the Charlie's pussy, popped her cherry, and shot his load. In the surreal reality of the dream, the teen was instantly pregnant, and Tina had a dream-state montage of perverted sexual acts over the course of 9 months while the Charlie's belly ballooned. Castle didn't fuck her pussy again, so when she gave birth, it was thru her almost virgin pussy. The dream version of herself sucked a load of sperm from Castle as they watched Charlie push his baby thru her torn open pussy.
She woke up at 5pm as Castle was pushing into her ass for her evening buttfuck before she went to the diner. After the initial pain, she settled in and let her boyfriend use her ass again while thinking about Charlie and her dream. She started playing with her pussy, but after a few seconds Castle noticed and told her to play with his balls while he buttfucked her, so she stopped. After 30 minutes or so, he pulled out and told her to suck it. She knew what he expected and sucked and jerked him until he emptied his balls in her mouth. She licked him clean, then as he dozed back off she got up to get ready for work.