Please see the content warning on ch. 01 and 02. Multiple disturbing scenarios and situations are included in the story.
Three
Violet sat in the back of a towncar, a black dress clinging to her porn star curves and a faux fur scarf obscuring her neck and shoulders. Large black Christian Dior sunglasses sat high on her nose and obscured half her face. She'd dyed her hair black as well, but still left the purple streak. The car (she thought it was a Maserati sedan of some kind but she'd never bothered to ask) pulled up in front of a high rise. She got out and headed inside, where the security guard immediately recognized her and summoned an elevator that would drop her at the correct floor. She didn't pay any attention to the wood paneling on the floor she exited and didn't remember the names embossed on the wall, other than knowing they represented Darren for all things legal.
She walked into a corner office with tall windows and a wall full of books to sit down across from a lawyer. He was older but not as old as Darren had been, and looked like he kept himself in shape. His brown hair was neatly styled and he smiled a sympathetic smile at her.
"I'm sorry for your loss Mrs.-"
"Hardigan," Violet interrupted him, "I'm...I'm going to go back to my maiden name. It'll avoid confusion, I think."
"Let us know if you want our help with that," the lawyer told her.
"So what's the story with the will?" Violet asked, "Am I even getting anything? Should I have grabbed my jewelry on the way over so I still have something?"
The lawyer looked confused, and said, "No...Um, Miss Hardigan...Darren left everything to you. You're the sole inheritor."
Violet had to pause for a moment and she knew her mouth was hanging open. The lawyer seemed confused. "That's...usually the case with these matters. Was there something unusual we should know about? A child or other relative or something like that?" the lawyer asked.
"No, no, I just...well anyway, everything? All of it? The houses, the money, the stocks or bonds or whatever?" Violet asked.
"Yes, all yours. There are some issues with taxes we'll need to work out but other than that everything is pretty cut and dried," the lawyer said, "Mostly you just need to sign some forms."
He put a stack of paper on the desk but it wasn't nearly as large as Violet imagined. Violet paused as she took the pen the lawyer offered her. "Was there anything about a briefcase? In a deposit box or a foreign account?" she asked.
The lawyer shrugged. "We don't deal with itemized lists like that; the insurance company would have a record of that if Darren had a policy for it. But like I said the entire estate is yours, so any briefcase he had would be yours now."
Violet felt herself relax and began signing. The process seemed to fly by and by the time she signed the last sheet of paper she was smiling. She pushed the sheet of papers back to the lawyer.
"Great!" he said, "There's just one more proviso from the will."
"I thought you said everything was clear," Violet said, now guarded.
"Well, yes, this is just a formality really," he said.
He bent down below the desk briefly, then came back up and put a baseball bat on the desk. The end of it had nails poking through the top.
"So to finalize the inheritance, you have to take this up the ass for 5 minutes," he says.
"WHAT?!" Violet screamed as she jumped up.
"Like I said, it's a formality but it was specified in the will, so..." the lawyer said with a shrug.
"No, fuck that, I'll give it up, I don't want it!" Violet said as she started backpedaling.
"I'm sorry but you already signed the papers," the lawyer said.
Two men suddenly appeared behind her and grabbed her arms, pushing her forward and bending her over the lawyer's desk. She felt her dress get pulled up and then there was a tearing sound and cold air on her ass. Violet tried to scream but she suddenly seemed to have lost her voice.
"Brace yourself," the lawyer said and then her ass erupted in pain.
* * * * *
Violet woke and started to scream but a strong hand clamped over her mouth.
"Good morning honey," Darren hissed in her ear.
She felt him move on the bed and the pain in her ass increased as his cock pushed into her. In her haze of panic and disorientation she couldn't remember any of the tips or hints she'd been given about anal and Darren basically forced his way in by brute strength. He had lubed himself up somewhat, so each thrust made some progress. Violet cried out at each thrust, and after six he was fully buried inside her. By then Violet was almost in a complete fetal curl and sobbing.
Darren seemed to ignore it and started fucking her ass. Violet flailed with her arm but Darren trapped it effortlessly, twisting it up behind her back.
"If you keep thrashing your shoulder will dislocate," he said, "You know how hard it is to do things with one hand?"
With one arm trapped by him and the other stuck under her as she lay sideways on the bed, Violet simply surrendered, whimpering as Darren's cock slammed into her. It seemed to go on for ages, and she again started to feel the unwelcome tingle of pleasure in her ass as the pain lessened when the sweat, precum, and lube mixed enough in her ass to provide a smoother glide. Darren fucked her longer than any of his staff had the day before, so she began to get used to the pain/pleasure mix. Before it could lead to anything, though, his cock pulsed as his orgasm fired ropes of cum into her bowels.
They lay together in bed, unmoving, as Darren's cock softened and eventually slid out of her ass. Violet realized it was slightly less painful than the quick withdrawals of his subordinates the day before.
The covers were jerked away from her and she felt the bed shift. She was still nude so the colder air was a shock and she curled up more, but in what seemed like seconds Darren stood in front of her, also naked.
"Let's go," he said, pulling at her arm.
She resisted the pull and then there was a crack and sting against her butt cheek.
"Your ass is going to be covered in tic-tac-toe boards if you keep this up," Darren said, "Let's. Go."
Violet got up herself this time and Darren pushed her toward the master bath. He somehow turned on all the lights in the room; overheads, vanity lights, and the lights in the shower. Other than the shower floor and the sink countertop everything was white and the room seemed blinding as Violet blinked to get her eyes to adjust. Darren walked around and stood in front of her, placing a short whip on the counter.
"Look at my cock," he said.
Violet already had her head down, so she only moved her eyes to see it. It glistened a bit with the residue from her ass, and had some dollops of cum near the tip. It also, she realized with a slight gag, had some bits of brown on it.
"You nearly fell asleep in the shower last night. I had to dry you off and guide you to bed while you were in a stupor. That means you weren't able to clean yourself last night as I told you. It's Monday morning. Do you remember what I said about Tuesday?"
Violet felt her face pale and her gag reflex act up as she recalled his promise that she would be cleaning his cock with her mouth by Tuesday.
"Now, continuing your education on living here. The first rule was about Sunday afternoons. The second rule you need to be aware of: As you can see from the clock on the wall, it's 5:45am. I wake at 5:30 every day except Sunday, when I sleep in until 7:00. I'm not as virile as I once was, but I'm in decent shape, as you know. That means I have the same problem in the morning as most healthy men. I expect it to be taken care of, but I'm a busy man with a schedule to keep. My cock should be inside you by the time I'm up at 5:30. It's your responsibility to ensure that happens. If my cock isn't inside you, I'll put it inside you wherever I like."
"I...I didn't know that," Violet protested.
"You do now. I feel that throwing people into the deep end is the best way to train them. I know that up until recently any time in the morning before eleven was mostly a rumor to you. I suggest you start retraining yourself. I abhor alarms, so if you need to do it that way sleep in another room and set an alarm for 5:25 or however early you need to so you can see to my needs in time. Or you can sleep in the master and take the chance that your circadian rhythm will adjust quickly so you don't have too many mornings where the thing waking you up is my cock thrusting into one of your holes."
"The third rule you already know; starting tomorrow every time my cock is inside of you, you'll be cleaning it off with your mouth after I cum. You already eat pussy, so licking your own juices off my cock shouldn't bother you too much. I suggest you make very sure you're keeping up with your enemas. Also I was informed you had some issues with giving an effective blowjob yesterday. You were barely tolerable yesterday morning. You should work to improve that."
Violet stood naked in the bathroom with her head down. She wanted to lash out and yell at Darren but she remembered the stinging of the whip and the paper she'd signed the day before. She felt a tear escaping from her eye again.