Jail Bird Pt. 01

"Yes Mistress," Jessica said, her eyes running down Max's back before settling on his ass as his jeans contoured tightly to them. She remembered how small he looked, all panicky in the courtroom, six years ago. Now how she couldn't wait to feel those hands on her, his hips slamming into her, his cock surging through her wet cunt. She would do anything her sister wanted to be able to be fucked by a real man again. Not that she didn't love it when Kate had her moaning like the slut she was on her bed almost every night. Yet there was nothing like a real cock when it was fucking her.

"Take a right here," Kate said, as her cane tapped along the corner of the building. "Do you see a dark blue car at the end of the building?"

"Yeah, why?" Max asked, looking over at her.

"That's where your treat awaits, I think six years without a good fuck is long enough. Don't you think?" Kate asked, with a devilish grin. She didn't care if they were out in public the world needed to know whose cock it belonged to or will belong to and who she was willing to give a ride on it. Max might not know it now, but he will soon, that he was her man now. The way he made her feel in the restaurant told her such, and she doubted that she would ever find another man like Max.

"Kate?! What are you doing?" Max asked perplexed, as he watched how her hand rubbed his cock.

"Me? Oh nothing, just getting this hard thing ready for you," Kate purred as she looked up at him. Her left index finger directing her sister to go get ready. "After all, I would think you would like to fuck my sister at the first opportunity you could get; and what better way to humiliate her than to do it in public and near the dumpsters?" she asked, with a wicked smile as her sister walked past her. All the while she was mentally measuring his cock in her mind. Knowing what she was going to dream about that night and fantasize about when she got her sister home so she could eat his cum from Jessica's cunt. She had to know what he tasted like. She couldn't submit too soon, then if he turned out to be as weak as the other men in the city... she couldn't think like that. It was better to wait and hear what he does from then on.

"Okay, so you're a fluffer, neat," Max teased.

"Only for you," Kate said to herself pressing her body against his as they started to walk again.

"Hello Max," Carol said, as she leaned against her car. Her shoulder length brown hair swayed in the breezed. Her brown eyes ran down her brother's body noting how tense he was. The way his jaw muscles clenched as he looked at her. She knew this was going to be a challenge when Kate informed her of her task. It was in her rookie year seven years ago when she joined the force that she had met Kate by accident or that's what she believed anyway. Being under the pressure of all the men's eyes on her for her first year on the force and also the sister to Maximillian Daysome who at the time was under investigation for Kelly Watts's murder. It was a very tough year for her. She met Kate in a bar one night. Being a cop she looked out for Kate given how she noted the men's eyes on her. One thing lead to another and she found herself on her bed, Kate between her legs, and her tongue doing things to her that she thought were impossible. As the months grew and their encounters grew more adventurous, Kate finally took her to her club where she made her into her own slut as she allowed three men to do with her body as they willed. Did she feel dirty about it, hardly. She did it for Kate, because she could see the joy in her eyes as those men fucked her. Now after seven years, their encounters weren't as frequent as she would have liked, given her hours. Still, if she showed up at the club and knelt before Kate and asked her Mistress to use her. She knew Kate would, and her focus would only be on her; and she loved her Mistress for that when she knew she had others.

"Go on, enjoy that little slut of mine. I'll entertain your sister while you take care of your manly needs," Kate whispered into Max's ear as her hand rubbed his back.

"You really okay with this?" Max asked, looking at Kate and ignoring his sister.

"Very," Kate nodded. "I just want you and this," her fingers ran down his stomach along the denim fabric of his jeans before cupping his cock, "to be as pleased as you can be."

"Okay, I'm not about to look a gift horse in the mouth," Max said, shrugging his shoulders. Only to stop as Kate held onto his shirt sleeve. "Need something?"

"A kiss?" Kate muttered to herself. "Cum inside of her as much as you want, make sure its inside of her," she said, forcefully.

"R-right," Max said, drawing out the word. "Must have some twisted thing going on, but hey, free pussy. Not like I'm going to pass that up," he said to himself.

"Now you enjoy yourself," Kate winked, before holding out her hand to Carol. "Come let's take a walk, you and I," she said, in a light hum as she wrapped her arm around Carol's.

Max shook his head as Kate walked across the parking lot with his sister. Walking along his sister's car, he noted how Jessica was leaning against the brick wall, her head bowed, and her panties in her hand. Already knowing what was to come, he smirked at that.

"How do you want me?" Jessica asked, in a small voice. Her eyes barely flicking up to recognize his presence.

"First: I want to see your tits, so take that off," Max said, gesturing to her suit jacket.

Unaware of how Kate and his sister hid behind the box truck on the other side of the parking lot with a video camera aimed directly at them. Kate wanted to capture her sister's humiliation on tape. This was only the beginning for her sister. This was her punishment for making such a huge mistake that could cost her a lot of money.

"Who knew you had nice tits," Max said, as he stared at Jessica's bare 36D breasts once she had undone her shirt. "You wouldn't know with that stick up your ass in court." Again, her head was bowed. Was it shame, or was it her submissive nature? Max couldn't tell, nor did he care. Personally, he didn't care, he wasn't about to have some new found romantic relationship with her. Max was going to fuck her hard and fast, as simple as that.

"Would you like me against the wall?" Jessica asked, lifting up the hem of her skirt as did her chin. "I'm your slut now, use me as you want. Fuck me as long as you want. Where you want. How you want. Just please fuck me. I need your cock in me," she pleaded showing off her naked mons Venus. She knew the moment her sister told her that he could fuck her that's when she knew she would be shared with Max when her sister didn't have a need for her.

"Hands on the hood," Max said, nodding towards his sister's car. He didn't want her hidden, he wanted the whole world to see what a slut she was. Oddly, Max was a little taken aback as Jessica walked over and slammed her hands on the hood of his sister's car and presented her nice round ass to him without saying a word. "Well, look at you all fucking wet already," Max said, slapping her ass. Listening to the moan that escaped her lips. "Oh, methinks someone likes that?!"

"Yes... Master, I love having my ass slapped," Jessica said, her body trembling as she felt the sting on her other cheek.

"Did you enjoy sucking the cock of the man you sent to prison?" Max asked, as he unzipped his fly.

"Yes Master," Jessica stuttered at the sound of those metal teeth. "I can't wait to do it again, and again, and again," she said truthfully, not knowing what punishment she would get if she lied to him. Yelping in surprise as Max snatched her head back by her hair. Her eye quivered as she peered out of the corner of her right eye as he leaned along her body.

"This won't be quick, this won't be gentle, and it won't mean anything," Max hissed in her ear.

"I understand Master," Jessica said, her voice trembling as he felt his cock brushing along her clit. A loud gasp filled the air as Max thrust hard into her without warning. "Oh shit! Yes Master, fuck me!" she begged as Max pounded her cunt.

******

"What's happening?" Kate asked, as she stood beside Carol as she slyly taped it all.

"Well, your sister's tits are flying everywhere, there's that, then her hands pounding on the hood of my car... she better not leave any dents. Wow! That's got to be her third orgasm so far," Carol said, giving Kate a play-by-play. Making sure she captured everything. Watching how Jessica's face held a lustful glee to it. "Looks like she feels him cumming inside of her."

"Good."

"Mistress what are you playing at?" Carol asked, looking over at Kate.

"Right now? Nothing. Just giving my new friend the release he needs after six long years and who better to get it from than fucking the woman that put him away. As his sister, I thought you would understand that; or did you forget that when you tossed him away," Kate said, coldly.

Carol couldn't say anything to that. What could she say? Hey bro, sorry for not writing you or visiting or simply talking to you for six years. How was prison?!

"So are they done?" Kate asked, eager to taste Max's seed from her sister's cunt.

"It appears not Mistress," Carol said, zooming in, wishing the camera had better audio on it as her brother hammered into Jessica.

"Well, he does have six years of stored cum to get out," Kate said, with a coy smirk.

******

"Yes! Yes! Fuck me like a bitch!" Jessica growled as her sex ran down her thighs with every thrust of his cock.

"You're loving this aren't you?" Max huffed as Jessica's cunt gripped him tightly.

"Yes Master! I love your cock!" Jessica loudly moaned as she came once again. Grinding her ass against his hips as she painted that hard cock in her cream. "Please Master, fill my womb up again, it felt so good feeling your cum painting my slutty cunt," she pleaded.

Max tried not to be weirded out by her tone, yet this wasn't what he was used to before he went in. Not that he was going to stop her from degrading herself, it was just too much fun to watch. He didn't know if he could do that with other women, yet for Jessica he'll call her a bitch, a slut, a whore all she wanted, she had it coming in his mind. He gave her no warning as he came for the second time in her cunt. He knew that since his time in prison and only having sex twice, once with Kelly Watts, a week before her death, before he went in. That he wouldn't be able to prolong the experience. Listening to Jessica whimpering as he took hold of her hair once he pulled his rather satisfied, spent cock out of her. Forcing her to her knees and holding out his soiled rod.

"Clean it," Max growled in-between breaths. Jessica wasted no time in latching her mouth onto his rod, her tongue swirling around it cleaning it of every trace of her sex.

"All clean Master, any hole of mine you want to use is yours," Jessica said submissively, as she stared up at Max. Gently putting away his cock and ever so carefully zipping up his fly. That was the first time in ten years she's been fucked by a real man and she had no inclination of stopping now. Dilan would shower her, pamper her, and then give her a half-baked ten minute sex that led to her masturbating to get herself off in the last year before he became Kate's sissy. Max on the other hand, took what he wanted, fucked her how he wanted, used her like she wanted to be used and gave her orgasm after orgasm before finishing. She couldn't wait to spread her legs for him and feel that hard body of his above her.

"Put your panties back on, I want you to feel my cum soiling your body all the way home," Max said, darkly.

Jessica released a rumbling groan at his forceful tone. She'd do anything to be with him again all so he could treat her like the slut and bitch that she was. "Yes Master, anything you want, I, your slut will do," Jessica said, biting her lip as the cool fabric pressed against her hot, wet, sloppy cunt.

"Seems you're finished," Kate said, as Carol whispered in her ear. "Well Max, did you enjoy my sister's slutty pussy?" she asked, with a knowing smile.

"She's..." His eyes ran down Jessica's body as she quickly buttoned her shirt. "Well, let's just say it's a start."

"I hope that means you'll take advantage of her whenever you need," Kate said, with a twinkle in her eyes.

"Who am I to say no if she wants to drop down and suck me off, or beg to be fucked? Not like I'm going to eat her pussy or anything," Max said, shrugging his shoulders, not caring if his sister was standing there.

"Master," Jessica whispered as she closed the gap between them. "If I'm a good little slut would you, then please taste me?" she asked, in that subdued tone.

"I don't know, I've got six years to make up for, you have to be awfully good for me to do that," Max said, scratching his chin, noting how Kate was smiling. Like she got off on the fact that he was going to use her sister as nothing more than a fuck toy.

"We'll see," Max stated doubting that would ever happen. Hoping his lawsuits would have run their course long before then.

"Come Jessica, I'm sure Max would like to spend his first night free resting or drunk," Kate said, waving her sister over. "He has a big day tomorrow, so we shouldn't take any more of his time."

"Of course Mistress, I'll see you later Master." Max was a tad surprised when Jessica kissed his cheek. If he had known that was coming it wouldn't have happened.

"A car will pick you up at one in the afternoon tomorrow, then you're new life begins," Kate said, waving goodbye to Max once Jessica joined her side.

"Well... can I buy you a beer or do you want to go straight to my apartment?"

"Seeing how I have no legal ID now, apartment." He couldn't wait for the four days to pass; he wasn't about to reconnect with his sister. He was just going to use her for a place to sleep then disappear from her life like she did with his.

To Be Continued...