The Gray Man Ch. 21 - Isabella

Shooter had slipped his cock out of his cover alls as he steadied her hips and pushed forward with his erect cock. Shooter wasn't small, but Isabella almost sighed in relief as the cock was average, matching the size of every cock that had ever been inside of her. Shooter moved his erect cock up and down the crack of her a times before lining up with her pussy and pushed forwards gently even as she issued her muffled protests around his partner. Shooter kept pressing until he was completely sheathed inside of her.

"Boss, I think she likes it, she's soaked," Shooter taunted as Isabella felt her hot ass against his cooler skin which was another purposeful mind fuck in the spies arsenal. Shooter stayed still before he started to thrust in time with Gray so that they matched each other stroke for stroke.

For Isabella, the humiliation of being bent over and then taken from both ends overwhelmed her. She closed her eyes with shame as she was rocked between the two men. Behind her, the shorter captor used his grip on her hips to drive her back onto him every time, a stinging reminder of the riding crop.

Isabella found her own rhythm. Gray smirked behind his balaclava as the judge had moved from being face fucked and was moving as well as she could on her own. Shooter drove himself forwards once more before his hands left the woman's hips to reach underneath her and cup her small swinging breasts in both hands, using these as leverage to ensure she maintained the pace he'd established for the three of them. Pinching her nipples between his thumb and forefinger, he squeezed tightly, relishing the feel of her flesh and having her under his complete control.

Isabella's tits had always been very sensitive. She moaned in pleasure around as much of Gray's cock as she could fit in her mouth.Gray pushed himself in more deeply, feeling himself touch the back of her throat as she was forced against him from behind.

Gray waited until the next thrust, before he pushed in slightly deeper again as he felt her gag reflex trigger around him. As she was impaled once more on his partner Gray again started to gently fuck her face until Isabella was thrashing around as her first orgasm crashed through her body.

The fear, the stings of the crop, the power of the two strangers, being spitroasted between a nice cock and a huge cock, and the hands on her tits were too much and Isabella had as powerful of an orgasm as she had ever had in her life, moaning around the head of TJ's huge prick.

Mark pulled out of the judge as Isabella felt his hot cum paint her back. The cock in her mouth didn't seem anywhere close to an orgasm.

Shooter walked to the wall and undid the rope as Gray pulled his monster out of Isabella's mouth with a plop, leaving the judge gasping for air.

Shooter patted Gray on the back, "Your turn champ."

Gray lifted her as Isabella flexed the cramping and pain out of arms. The tall man took her gently by the elbow and led her to a mattress that was braced on blocks and plywood in the corner of the warehouse.

Gray gently pushed her back onto the bed as Isabella's eyes widened when she saw his enormity. Gray's cock. She had no idea how it fit in her mouth. She had never seen a cock so large. There was no way he could possibly fit inside any woman. "No,keep away from me. I won't tell anyone about this, but you need to stop now. I promise it."

Isabella babbled as Gray used his fingers to open her labia, stretching them wide apart, and he aimed his gigantic cock at her moist entrance. Isabella reached down to block him before she recalled the punishment. Her manicured fingers merely grazed his hand and stopped short of their intended goal.

The large head of Gray's cocks pushed at Isabella's wet opening and she became frantic. She didn't know what to say or do to stop him, her fingers uselessly his shoulders as he opened his thighs causing her legs to splay even wider.

Her mind was overwhelmed, racing. She tried to force herself to wake up, hoping this was just a horrible nightmare. She didn't wake up, this wasn't a nightmareThis monster was fondling her pussy, trying to put himself inside her. She felt like a paralyzed spectator watching this horrible crime being perpetrated on someone else. "I'm sorry I'm I'll do anything you want. Please don't. Oh... no... you're too big..." she begged

"Listen bitch, this is what you wanted and now it's what you are going to get," Mark said from somewhere off to the side of her.

The pressure from his attempted invasion built. She couldn't watch his huge cock and what he was trying to do to her anymore. Isabella fell back, clenching the sheets in her fists. "Oh, god! No... Please. You're hurting me. Don't..."

Mark watched amazed, his cock slipped into her so easily and Gray's cock stretched her. He had to admit he was jealous of not only Gray's size, but his stamina. Gray slowly applied more force to overcome her pussy's resistance. Her moist labia finally surrendered, engulfing the head of his penis. "Good girl," Gray whispered, "Look at that tight Italian pussy taking my big cock. Damn, you are a tight one.

"Ow, god, no," Isabella cried, as Gray pushed into her. Her pussy stretching for him and subversively providing lubrication for its own assault."

Gray gradually advanced more of his cock into her. "Is this your first time with a big cock, Isabella? You've got a convict's huge cock in your pussy now. Shoving into you, just like you shoved me into prison. How does it feel?"

"Oh god, stop it! Please, you're hurting me. Don't..." she whimpered

"Ironic isn't it, the prosecutor, the victim, my family said the same thing to you, and you didn't listen. Why should I listen to you now, bitch? Try and relax some and it'll be easier. I am going to fuck you, if you relax it will be much better for you."

Isabella couldn't relax. She felt him advance slightly deeper with each thrust. "No, no. Why are you doing this?"

Shooter spoke up again, "This is what you wanted, and because we can."

Isabella could not understand why the short man kept telling her this is what she wanted. Then a flash went off on a phone. The little prick took a picture of her, her arms on the tall man's shoulders as his cock pushed into her.

Gray placed his index finger to her lips. "Shh, be quiet. We told you before why this is happening. It's what you wanted. You're going to belong to me now, a common size queen."

Suddenly Isabella remembered the contract, "No, this is not what I thought I was getting," Isabella whimpered. "I don't want this," she whispered. But her pussy acted contrary to her words and as nature insisted, welcoming his hardness and coated more of Gray's cock with a moist, affectionate-like sheen, traitorously helping him to penetrate deeper.

The shorter man was now beside her, "You even said in your request to not stop, no matter how bad you fought. You said it would be more real that way."

Isabella's mind raced as the mind games from the evening did exactly what they were intended to do. Why had she done this to herself? Why was she so wet for this disgusting man and why couldn't she control her own body? These and similar thoughts circulated in her mind, her face displaying both her physical and psychological anguish as furrows in her normally smooth skin.

Isabella's pussy contained more cock in it than ever before. Gray's cock was triple the girth of Ryan's and visited Isabella's uncharted depths. With most of his length inside her, Gray mercifully refrained from going further. There was no need rushing things their first time together and causing her excessive discomfort.

"Ah, ah, ah, ah, ah," Isabella moaned as she felt his cock touch her cervix. Her entire body convulsed as the pain turned to pleasure and an orgasm rocked her small body, her nipples hard, her head tossed back, her arms now gripping the stranger's biceps.

Gray attempted to look directly into her brown eyes while fucking her, but Isabella kept averting his stare and moving her head away from him. "No!" she snarled.

Gray's eyes narrowed into an angry glare as he grabbed Isabella's chin, and forced her to look at him. "Bitch, you will look at me when I'm fucking you. I'm not like those limp dicked guys you've had before. Look at me or we will get the rope and tie you back up."

From beneath pools of tears, Isabella's eyes met his as he claimed her. She felt his immense cock making its long journey in and out of her defeated pussy, now his conquered territory. "Please stop it!"

"No chance of that, your honor. Maybe if you cum I'll think about it." Gray smirked from behind the balaclava" Gray occupied conquered territory deeper into her stretched pussy than any other man had ever been. That wasn't enough, not today. He wanted her to completely surrender to his cock.

Isabella replied with silence, determined not to give him the satisfaction of her orgasm and total victory.

Gray smirked, "Oh, you are going to cum all over my huge cock, whether you want to or not," Gray warned, as he quickened his pace as if reading her thoughts and determined to defy them.

"No," Isabella hissed through clenched teeth. But the physical discomfort of having Gray so deep inside her had already dissipated, her vagina accepting his large cock, bathing it with juices as she fought her natural desire to move her hips.

Gray shifted position and felt her pussy begin contracting around his dick in response. Mark smirked behind his mask, he had seen his friend fuck many women and his big cock was just too difficult for any woman to deny. No matter the size, no matter the race. Despite their resolve and hatred for him, nobody lasted long with stretched around Gray's cock. He finally spoke, "Go on bitch, cum on his cock. Listen, you can hear your slutty pussy splashing around his huge dick. You are fucking loving being impaled on his cock. Admit it."

Isabella grimaced, as her hands pushed against Gray's muscular chest. How could he make her body do that? But his thick shaft kept stretching her cunt and giving her sensations she had never felt, sensations that she didn't want from him but couldn't stop receiving. "Oh... oh... don't... oh -- no Please God, no..."Isabella's voice grew louder as her unwanted arousal increased. "No, no, no-- stop doing this to me! I don't want to cum for you. You're disgusting and I hate you. Oh, god. Oh, ooh, ooh, don't..."

Gray felt Isabella's vaginal muscles spasm from a second, stronger orgasm as he continued to fuck her.Now her pelvis replied with slight movements of its own, her body revealing an increasing desire to engage in the sex act. It was an autonomous response she tried to prevent. Not quite the enthusiastic reaction from her that he sought, but for now, at least, she had tired of resisting. He mercifully withstood the urge to bury his remaining length inside her.

Isabella had cum more in the last 5 minutes due to his monster cock than she had in a year of sex with Ryan. "Please, you've got to pull out now," she begged. "Don't cum in me!"

Mark laughed, "Baby girl, he's nowhere close to cumming yet. The night is young."

Isabella was a pampered Italian American woman. Raised privileged, never having to work hard for anything, breezing through law school, youngest partner in the history of her former firm and one of the youngest judges to be installed on the bench in the district. Gray enjoyed every step of taking her: initially molesting her and causing her body to respond in a way that was incredibly embarrassing for her; introducing her pussy to his huge cock; making her orgasm from it and causing her additional shame.

"Please, I admit it, you made me cum, please stop now, you said you would," she whimpered as he stopped thrusting, just the head of his huge cock inside of her engorged lips.

Returning to the role of convict he snarled, "Just like you said you'd take the recommendations into consideration, and then threw my ass in prison. We aren't done until I say we are fucking done."

She couldn't let him continue. She knew he was about to break her, like the short one said he had done to many others. She was a fucking judge, not a common slut addicted to cock, no matter how good or big it was. Isabella's dainty hands renewed their efforts as she pushed harder against Gray's muscular chest. She arched her back and repositioned her pelvis, like they had taught her in jiu jitsu. She tried squeezing her vaginal muscles to dislodge him as she shifted her weight. Her efforts may have against Ryan's cock, but they were no match for Gray's gigantic cock embedded too far in her pussy to oust.

Gray's cocks securely occupied Isabella's cunt after her failed attempt to expel it, but he felt what she had tried to do. With a quick jab, he penetrated a little further for her insubordination. "We are not fucking done, your honor. You want more of me? I got a big, convict cock for you to enjoy. I was holding back, I was being gentle, but if you try that again, you will get all of my cock, ready or not.

To Isabella's chagrin, the thought that he had additional length to slide into her caused her to orgasm again.

Gray chuckled, "Such a slut, feel your pussy pussy milking my cock."

As another orgasm rocked through her she tossed her head to the side and opened her mouth as Shooter stuck his cock that had gotten hard again into her mouth and started to thrust.

He pushed past her gag reflex, thrust into her mouth for maybe a minute as Gray just flexed his cock in the judge's pussy. With a growl Sharpshooter shot his second load of cum, this time into her mouth.

Gray shook his head as he felt sorry for Gretchen. Mark's cock wasn't a bad size, but he'd come twice already and very quickly. Gray knew now why Gretchen had said, "He's done already" when his call interrupted their sex.

Gray pulled his cock out of her slowly before pushing back in. Her beautiful nails dug into his hips from sudden pressure and pain as he pushed deeper. "No more, god, please, no more, I can't"

Gray smirked, "What do you mean you can't? Look at my cock. It's buried in your tight cunt, you took it all."

Isabella looked down in horror and watched his entire penis, its long, thick shaft triumphantly wearing her milky secretions, repeatedly and completely invading her pussy. She felt his immense scrotum slapping against her asshole, further attesting to his victory. She looked up at him, their eyes meeting, the pain abating as her body adjusted to his entirety. "Oh god, holy shit," she moaned as she came again. When she opened her eyes they showed panic, "Please pull out! Don't cum in me."

Gray smirked, "I'm not even close to cumming, we have all night."

"Please, please, no. Don't do this to me," Isabella murmured while accepting defeat. Her hands remained on Gray's hips, but no longer grasped him in pain or attempted to hold him at bay. For now, at least, he had conquered and dominated her.

Gray's eyes softened, "Do what Isabella?"

Her body shuddered, "Please don't make me cum on your cock again."

She closed her eyes and could only see images of his thick, long cock tunneling through her quivering tissues, parting them all the way up her birth canal, expanding her pussy, causing it to stretch around him. The head of his penis practically reached her cervix. Gray embraced her in his arms as he leaned back onto his knees and changed the angle of his thrusts causing an entire new feeling to spread over her body.

"Oh, oh, oh, don't make me cum again, Please. I don't want to. I can't do this. I'm not a slut," Isabella moaned, "Oh god, no please, not again."

Gray felt her pussy throbbing around his cock. He kept making her orgasm and this one was more powerful than all the rest.

"No... please. Not again," she moaned. The confident judge, on her way home to enjoy a well deserved weekend had been sexually broken and currently replaced by a sniveling schoolgirl. "You can't do this to me again. I won't let you."

"Yes, your honor, I can and I will." Gray said as he pushed deeply into her again, with an agonizing slow push. Gray finally pulled his cock out of her, agonizingly slowly.

Isabella was surprised that she was holding her breath as Gray pulled out of her, until she exhaled. 'Thank God' she thought it's finally over. That was until Gray scooped her up and carried her to that large oak table and bent her over it. His cock again positioned itself in direct line at its target..

Isabella wearily raised herself up on her elbows and tried to turn around, but he held her hips firmly. "No, please wait..."

Gray thrust forward. Ashamed, Isabella felt her eager pussy separating for the head of his cock and granting it entry. "Don't, please not again", she whispered as she collapsed on the table, air evacuating her lungs as his enormous prick slowly advanced all the way into her, until its head practically reached her cervix and his heavy balls touched her engorged clit. The walls of her pussy began convulsing uncontrollably. She reached forward, her fingers clutching the edge of the table in front of her and her knuckles turning white as she came again in a powerful orgasm.

Gray's strong hands continued to hold her hips as he reversed course, unhurriedly pulling almost completely out, until just the bulbous head of his cock remained, her pink labia tightly stretched around it like the lips of a mouth sucking on a large lollipop. Gray paused for a moment, letting the reality of what was happening to her sink in and the anticipation built, before embarking on his return journey to the furthest possible depth inside her, and repeating this process with a steady, predictable rhythm.

After another orgasm Isabella moaned, "Stop, I hate what you are doing to me, and I fucking hate you. I'll have you in prison for life if you don't stop."

Gray chuckled as his hands moved from her hips to her butt cheeks and spread them wide apart. Her pink asshole winked at him as he gently ran his thumb up and down across it. "Awe, I see you also like me touching your asshole. Did Kyle ever fuck that gorgeous ass, how about Francesco?"

Through gritted teeth Isabella growled."No, they were not fucking animals like you. You are a sick, disgusting pervert. Pull out and stop rubbing me there. Oh... please"

Gray just chuckled and continued massaging her sensitive anus with his thumb while fucking her, causing it and the muscles in her vagina to contract in response and making her pussy squeeze his cock.

Off to the side, Shooter had his phone out taking pictures for Gretchen, positioning the camera perfectly to make it look like the good judge was thrilled with what was happening.

Regardless of how sick and wrong it was, Isabella began appreciating his generous circumference and depth. Fully inside her, he reached under her chest and lifted her off the table and into a standing position in front of him, his one hand cupping her breast, the other sliding down her firm stomach and beginning to play with her clit as he held her against his muscular body.

Isabella leaned back against Gray's strong chest, "No, don't touch me there. Oh, god, please stop."

Gray didn't stop. His fingers finessed her engorged clit. He kissed her neck and whispered into her ear: "You need to cum on my big cock and show me again how much you love it, your honor."

Isabella fought as she shook her head, trying to refuse him. That worked until his finger expertly retracted the protective hood on her clitoris and gently played with her exposed glans. "Oh, fuck, what, oh fuck, oh god, nooooo." she wailed as she tried to fight her own body as much as she was the tall one." She couldn't fight it, as her hands reached down and warmly held his wrist as he worked her sensitive nub. Her eyes grew dreamy, her head tilted back on his shoulder, she bit her lower lip, and her pussy began to throb on his cock.