Jail Bird Pt. 04

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Life for Max on the outside isn't how he remembers.
27.8k words
4.69
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Part 4 of the 4 part series

Updated 06/09/2023
Created 03/19/2020
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soul71
soul71
6,756 Followers

Thanks to WAA01 and Killerarmyguy for the edits.

******

Maximillian Daysome, or Max as he likes to be called now, rolled out of bed. A bed that wasn't his own. He hasn't had his own bed for six long years. He thought last night couldn't get more insane than it did when he had fucked his own sister, along with Jessica, the DA who'd put him in Lampac for a crime he never committed. He had to admit, as strange as it was, his sister's pussy did feel nice wrapped around his cock after so long being stuck in that six-by-nine cell. However, the greatest, and truthfully, the only, part of it that mattered was cumming in Kate's mouth. That was the highlight of the night. He could still feel Kate's lips on his manhood. The way those lips just molded to his rod; it was divine! Although the weirdness didn't stop there, no, his sister, Carol, was adamant that he take her bed, and as his slave, she would sleep on the couch. Looking down at his morning wood, then to the open doorway, hearing Carol in the kitchen.

"Max!" Carol yelped in startlement as his left hand took hold of the back of her neck and bent her forward over the sink. "Fuck, yes! Yes, Master, fuck my slutty, sisterly pussy!" she urged him on when Max roughly shoved her panties to the side. Hearing Max groan as he slid his cock into her welcoming pussy.

"You like that, don't you slut?!" Max grunted as he pounded his sister's cunt.

"Yes, Master, my pussy is just for you," Carol stated, fighting back her moan as she felt his rod surging through her folds. "Master, please, may I cum for you?" she pleaded after her long dry spell, she so needed to cum on his cock again.

"Fine, slut, cum all over your brother's cock," Max stated in a firm tone after shrugging in his mind. The weirdness had already taken place the night before; Max saw no reason not to keep getting her pussy when Carol was all the more willing to give it to him. Max didn't give her time to enjoy her orgasm as he kept pounding that wet hole of hers.

"Yes, yes, yes! That's it, Master, fuck me hard! Pound that pussy like you own it, because... it's yours!" Carol howled in bliss as her brother didn't once stop slamming his cock into her. Her legs violently shook as her brother dumped his hot load into her cunt.

"On your knees and suck me clean," Max ordered. He couldn't keep his eyebrow from lifting when his sister spun around without hesitation and dropped to her knees. Her brown eyes were always on him as her lips glided along his soiled cock.

"All clean, Master," Carol said with a smile on her face. "I have time before I have to start my shift. You can have my ass if you like, Master. I'm here to please you, Max," she cooed lightly up at him as she rested her hands on his thighs.

"Then work that mouth to get me hard again," Max spoke in an authoritative tone. Something he's never done, yet, it seemed to him, his sister got off on it, as did Jessica. Max kept his face placid as his sister attacked his cock. Working to arouse it once again. Noting how she stopped and twirled two of her fingers in her mouth before returning his cock back to it. Watching how she reached behind her and started to finger her ass.

"Master, come fuck this shitty hole of mine!" Carol begged as she held her ass cheeks open while her left cheek pressed against the floor. Wincing as his head eased into her ass, her grip tightened on her ass cheeks as her brother's cock inched deeper into her brown eye. "That's it, fuck my ass, Max! Fuck it hard!" she growled, bracing herself as he hammered that tight little hole of hers.

"You like that cock deep in your ass, don't you, slut?" Max hissed as her ass gripped his cock like a vise.

"Yes, Master, I love feeling your cock in my ass," Carol answered like the good obedient bitch she was. "Fill my ass with your cum, brother. I want to feel my Master's seed soiling my ass!" she begged, feeling Max's balls slapping against her pussy with every thrust of his hips. Her eyes rolled into the back of her head as she felt him burying his cock deep into her starfish. His hot spunk shot deep into her ass as her pussy came, coating her brother's balls in her hot juice. It always happened when she was fucked in the ass. While Max wasn't the biggest she's had back there, yet his was the only one that mattered to her. After all, he was her Master, and a slave like she is would do anything for her Master.

Max just stared down at his sister's gaping asshole watching his cum oozing out of both of her spent holes. Walking off towards the bathroom, leaving his sister still on the floor with his cum dripping onto it.

"Max?"

"Hmm?" Max hummed from the depths of the shower after ten minutes had passed.

"I'm heading to the station; do you want me to bring anything home for you?" Carol asked, standing in the bathroom doorway in her patrol uniform.

"Yeah, my birth certificate," Max called out over the sound of the water pounding on his chest. His hands ran over the scars he had earned from being stabbed with shivs and sliced open by them as well.

"Why?"

"So I can get me a new driver's license."

"You just got your full driver's license when you went in, right?"

"Yeah, why?"

"You do realize it's a seven-year license, so it's still legal, so you don't have to get a new one. You just need to brush up on your driving skills," Carol stated truthfully. "But if you want to get a new one, I'm off tomorrow; I can take you down to the DMV to get it renewed."

"Might as well," Max muttered before ducking his head into the hot streaming curtain of water.

Pulling her phone out of her left pocket when she felt it vibrating, taking a swallow when she noted her mother's caller ID on the screen of her phone. "I have to take this, Max, have fun at work today; tell my Mistress I said hello," Carol said before ducking out of the doorway and the apartment altogether.

"So fucking weird," Max spoke aloud as he shook his head at the life that greeted him after his release from six years of Hell.

******

"Hello, Mom," Carol answered the moment she was outside her apartment. Feeling her ass trying to return to its original size as she walked down the breezeway to her car.

"Hello, honey, how are you?"

"I'm fine, a little tired, but fine, these twelve-hour shifts take their toll," Carol said; in truth, she would have said anything to keep the fact that Max had not only fucked her pussy, but her ass as well, away from her mother. She fucking loved every minute of it!

"You're being safe out there, aren't you?"

"Of course, Mom," Carol nodded against her phone.

"How's your brother doing?" Carol knew this question was coming.

"Pissed. Pissed at you, me, Dad, everyone in the world. Wouldn't you be if you went through what he did while inside?" Carol spoke in a soft tone.

"And what happened to Max while he was in there?"

"Mom, I really don't think you want to know the answer to that question," Carol said truthfully as the sound of her car unlocking beeped in the early morning air.

"No. I think I need to know."

"Okay, but I warned you; he was stabbed twelve times, slashed eleven times, and almost gang-raped twice," Carol said, listing off the injuries Max had sustained on the inside. Withholding what Max had done to those who had attacked him. Hearing her mother gasp over the line.

"But we were told..." Carol heard her mother breaking down over the line as she started her car.

"I know, Mom, I know. I was there too, remember? Right now, Max just needs some space to get his head around the world he's reentered. You have to remember Max has been in there long enough to become institutionalized, so it's going to take him a while to adjust to the world around him," Carol said, backing out of her parking space. "Six years can't be undone in three days, Mom." Remembering what Kate had told her the other day. Feeling her mound reawakening just thinking of Max taking her on her -- now his -- bed, at least until he moved out. Which she knew would be coming any day now.

"You're right, you're right," Danica -- their mother -- admitted after calming herself down. "But you promise me you'll make Max read my letter?"

"I promise, even if I have to go over to his new place to deliver it," Carol nodded, looking both ways before pulling out of her apartment's parking lot.

"He's moving?!"

"He'll still be in the city from what I've heard, for now anyway, he doesn't talk to me about such things."

"Oh." Carol heard the sadness in her mother's voice as the left-hand blinker sounded off in that steady beat. "You be safe driving into work, okay, honey?"

"Yes, Mom, I will," Carol said, hearing her mother sniffle over the line. She knew the only time she would be getting fucked once Max moved out was to go to his new place and beg to be let in so he could pound her slutty, little pussy.

"Love you, baby."

"I love you, too, Mom," Carol replied, shifting in her seat as she felt moisture forming between her legs.

******

"Kate?" Max spoke into his smartphone that he had no idea how to operate. It was a miracle that he could open up his contact list if it wasn't for the white outline of a phone imposed on a green background. Also, it helped that Kate's number popped up when he hit the number one on the keypad, if you could call a digital display of it a keypad. He began to ponder if this was how his grandparents felt when VCRs came out. He recounted the times he heard his grandmother calling his father, wondering how to get the DVD player they had got them for Christmas one year, when he was ten, to work.

"What is it, Max?" Max cursed to himself; he should have known she would still be asleep at ten in the morning. However, he was bored, and Kate was the only one he knew on the outside that he didn't want to cave their face in for the words they said about him.

"I'm sorry, Kate, I shouldn't have called; go back to sleep," Max said; the image of her sucking his cock just wouldn't leave his mind.

"Max. You know you can call me anytime you want. You know I won't mind. So what are you calling about?"

"I was... wondering if you wanted to do something, you know, not work-related. I know it's still early..."

"And you're bored sitting in that apartment alone, aren't you?" Max felt his cheeks heating at her soft chuckle.

"Kind of," Max admitted.

"Well, Max, I'm waiting?"

"Kate, would you like to, I don't know, hang out, just the two of us?" Max asked, his hand running down his face at how stupid that sounded.

"As in a date?" Max didn't know why but he could have sworn he heard the smile in her voice.

"Yes, if you would like to label it as a date," Max nodded.

"I'd love to, Max," Max felt his heart flutter at how soft that voice of hers sounded at that moment. "Dilan!" Kate called out.

"Yes, Kate." Came an obedient male voice that Max could hear over the line. Knowing it was Jessica's husband whom Kate had sissified. He wondered if the man was always so weak that he could be so easily broken. The ones who tried that on him would be singing at a higher octave, if they survived. Maximillian Daysome was no one's bitch!

"Get my best dress out and help me to the shower. Max, give me an hour, and I'll take you to the best place to hang out."

"I'll see you then," Max answered, unsure why he was getting nervous for.

"And Max?"

"Yeah?"

"Wear the suit; where we're going, it's a must."

"Okay, Kate, for you, I'll put it on," Max said; while he wasn't fond of wearing it, nonetheless, he didn't want Kate to be disappointed. "Will we be going to the club afterward?"

"No. Think I need a day off, so I'm all yours... if you want me?"

"Hmm... how can I say no to spending the day with a beautiful woman? I'd be insane to pass that up!" Max said, laying on the charm.

"Max, you shouldn't say such things. What will the world think?"

"They can kiss that lovely ass of yours for all the good their thoughts on the matter are," Max stated firmly. Hearing Kate sucking on her lower lip as he waited for her response.

"You really think it's lovely?"

"Told you, Kate, I always say what I mean," Max said, feeling the corners of his lips lifting as his smile grew.

"You did tell me that. Okay, let me jump in the shower; I'll see you soon, Max."

"Don't keep me waiting, or I just might have to find you myself," Max joked.

"I promise no more than an hour."

******

Max was standing on the middle landing of the stairwell that led to the second floor level of his sister's apartment complex waiting for Kate to arrive. Wondering who she had gotten to drive her to it. Mentally smacking himself, knowing it was most likely Dilan she had wrangled into being their driver for the day. Knowing he was going to have to get himself his own car, so he didn't have to have other people listening to his and Kate's private discussions. His dress shoes resounded on the concrete steps as he bounded down them as a car pulled into the parking lot. Seeing the back door opening, telling him where he was supposed to be; at Kate's side.

Whistling low as he peered into the car. His eyes ran down the strapless, green, form-fitting dress she wore. Wondering just where she was taking him.

"Is something wrong, Max?" Kate asked, turning her head towards the open door.

"No, but, wow," Max stated as he slid into the rear seat.

"I take it 'wow' is good, yes?" Kate flirted.

"Very good, you sure you want to be seen with me looking that..." His voice trailed off as their car made a slow loop around the parking lot.

"Looking like what?" Kate asked, trying not to blush at his words.

"Hot."

Kate couldn't help it, not even if she wanted to. Pressing her lips together trying to keep herself from smiling as that word left Max's lips. Nevertheless, she was very happy that Max thought she was 'hot', as he put it.

"Thank you, Max; I'm sure you look very handsome yourself," Kate replied, running her hand down the front of Max's suit jacket. Yet, in reality, she just wanted to feel his muscles beneath her touch. After last night, dreams of Max taking her on his new bed played within her mind. To the images of her on her knees, peering up at him, her tongue out, waiting for his seed to coat it. In her dreams, she could see once again, and in them, Max was the most handsome man she's ever laid eyes on. "Dilan, does Max look handsome?" Kate asked, having to rely on her little sissy's eyes.

"Yes, Kate, he looks very handsome," Dilan spoke, peering at Max in the rearview mirror. "Mistress?"

"Yes, Dilan."

"Am I to service him as well?" Kate laid a hand on Max's chest, stilling his tongue when she knew what he was about to say.

"No, Dilan, Max is not someone you do that for, understand?" Kate spoke in a commanding tone. "That pleasure is all mine, and mine alone, minus his sluts," she quickly added to herself.

"Yes, Mistress, forgive me for assuming."

"You broken him quite well, haven't you?" Max whispered into Kate's right ear. Seeing that same smile she wore whenever they were at her club appearing on her face. Wondering if Kate's always been like this and her disability just brought it out more to make up for the loss of her sight.

"Of course I have, I am, after all, Mistress Lin of the club Diablo, where all your twisted fantasies come to life," Kate replied with a devilish grin.

"You sure? Mine haven't... wait, strike that, half of them have come true," Max mused, tapping his chin. Also, looking out for a gym on the way to wherever they were going. He could already feel his body going soft after three days of not pumping iron out in the prison yard.

"Oh? And what was the first one?" Kate asked, resting her hand on Max's thigh.

"Seeing you in that red spandex getup, very, very hot if you ask me," Max stated truthfully.

"And the last one?" Kate inquired, feeling the tips of her ears burning.

"So not telling," Max teased, his mirth finding its way into his voice. Chuckling when Kate just stuck her tongue out at him. "I wonder how much they charge?" Max pondered aloud as he turned his head as Dilan drove past a Gold's gym.

"What are you talking about, Max?" Kate asked, loving listening to him talk.

"Oh, just a gym we passed, need a place to work out, and doing push-ups isn't going to keep these muscles I have," Max said, turning his attention to her.

"Dilan?"

"Yes, Mistress?"

"Is there a gym near the brownstone?" Kate asked in an authoritative voice.

"Yes, there's a Planet Fitness, not a block from it," Dilan said truthfully.

"And how do I get there from it?" Max uttered, looking at the back of the man's head. Knowing he could wait two more days to go to it once he had formally moved into the new, to him, place. Also, he remembered what was going to happen that day as well.

"When you walk to the front of the building, take a right, then go to the intersection and take another right; you can't miss it."

"Thank you," Max said, seeing the man nod.

"Max, how often did you work out in prison?"

"Every day. There were bigger and stronger men in there, so I had to get big myself. Then well... word got around and the fish, that's what we called the new inmates," seeing her nodding along, "they tried to make a name for themselves."

"I take it, it didn't end well for them?"

"I don't have these scars for nothing, Kate," Max said truthfully.

"Were you ever put into solitary confinement?"

"A few times," Max admitted.

"What was the longest you were in there for?" Kate asked, eager to know all about him.

"A month, but so worth it."

"And what did you do to be put in there for so long?" Kate asked, leaning against his shoulder.

"You know what happened in the shower that one time? That was my punishment; wasn't like they could tack on to my already death sentence at the time," Max said bitterly.

"I have to say it was indeed worth it," Kate sighed, resting her head on his shoulder. Wondering when was the last time she actually took a day off just to have fun. Never, actually. To her mind, no one had been worthy enough for her to skip out on work, until now.

"So, Kate, where, actually, are we going?" Max queried, trying not to let his body react to how soft her body felt as she leaned against him.

"Oh, to the Mallard Head Club," Kate mused. "Did I make you speechless?" she cooed when she felt his body tensing at the name.

"Yeah, even I know where that is; you sure you want to be seen there with an innocent ex-con like me?" Max asked, knowing he so wasn't going to fit into that place, and he had no wish to embarrass her at what he knew was a very high-class establishment.

"I'm very sure, Max," Kate nodded, her grip on his left bicep tightened, feeling the knotted muscle beneath the fine fabric that made up his suit.

Kate felt her body heating as the car slowed down then came to a stop altogether. Hearing the right rear passenger side door opening and feeling Max sliding out of the car. Her dark brown strands of hair fell forward as her cheeks heated as she felt the pads of Max's fingers lightly dancing down her arm before his strong hand took hold of hers.

"Dilan, you may eat inside, but not with us, once you park the car," Kate directed once she had scooted to the edge of the rear seat.

"Yes, Mistress, I won't let my lowly presence interfere with your lunch," Dilan spoke in a submissive tone.

"Thank you, Max, that was very gentlemanly of you," Kate cooed once he had helped her to the curb. Wishing that he had left his hand on her left hip when he helped her up onto the sidewalk. Reaching into her purse, pulling out her folded cane, listening to it snap together as it fell from her hand.

soul71
soul71
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