The Gray Man Ch. 41 - Madison 02

Gray started to whisper in a low growl "Remember what I told you," he hissed softly. " I told you I would break you. And I keep my word. And I told you I'd make you beg for this cock."

He looked at Madison and smiled, "This is your fault. Look what you've done to a woman that has shown you nothing but respect. This is all due to your pampered incompetence. Trust me Madison, there will be a day when you spread your own legs wide. And you're going to ask for it. You're going to beg for it. And if I think you really mean it, I'll give you what you're asking for. I know it's big. It's going to hurt, maybe a lot. You can scream all you want when I ram it into you, into that tight little pussy. I want you to scream, it just turns me on even more."

"You're crazy," Madison found enough of her voice to whisper." TJ just kept rubbing his cock up and down Ana's slit as Madison continued. "I never want this," I insisted. He kept stroking. "I want you to go to prison, you evil bastard, you son of a bitch."

Gray laughed and tossed her his phone, "Then call Madison, call right now. The Journal, The Post, Pick up the fucking phone and call." Madison froze as Gray continued to taunt her, "You know you want it, you are just not woman enough to handle it." he whispered.

TJ turned his attention back to Ana, "Say it my little cock sleeve, I feel your cunt twitching already so close to orgasm. Look at Madison and tell me how your tight little Punjabi cunt wants to obey it's majestic white cock Master. Tell her how your cunt knows the truth. It wants me. It wants to be fucked, fucked hard, filled and pounded."

Madison watched in horror as TJ started to take small thrusts, never fully penetrating, just driving up the sexual torment for Ana. Madi was terrified Ana would cum again without permission and again be punished.

Finally, Gray bit Ana's shoulder again as he moaned, "Cum for me, bitch," The head of his cock struck her desperate, humming clit again and again. Ana found incredible release as her body finally found the permission it desperately craved. Gray's hand clamped over her mouth and her world exploded. The orgasm ripped through her like a ball of cold electric fire. A harsh yell erupted from deep in her throat, ringing against his palm. Her battered body vibrated, a struck bell.

Gray held still, feeling her cunt gush and throb against him. "Say it," he whispered, "tell me. Beg me." The words leapt out of my throat, shocking me as they poured into his ears.

"Oh. I--I---I need this. Fuck me. God, destroy me. Ram it into me, I want to feel you so deep your cock comes out of my throat. I want you to destroy me with it. Fuck me hard, hard as you can. Oh, God, don't make me wait." Ana was lost someplace between this world and another, she was babbling, out of control. Gray winked at Madison as he gave a low chuckle of triumph.

He bared his teeth, and a growl rolled out of his throat. Madison's eyes grew large as she saw the large man draw away from Ana before he pulled her onto his huge prick in one motion. Ana screamed as his huge cock plunged into her depths. Madison could only watch as Ana was impaled, being thrust back and forth on Gray's cock like a rag doll.

He rutted into her, slammed into her cunt with such force that Ana's tits bounced uncontrollably. Gray's huge hands gripped her hips as he moved her back and forth with such force that Madison was afraid Ana would get whiplash.

All Madison could hear was the thunderous slapping of Gray's hips against Ana's ass. Madi had never seen such power or force. Ana could only grab the edge of the desk to find some sort of balance. Madi wasn't sure how, but without missing a thrust Gray stepped forward, pushed Ana's chest to the desk and grabbed her arms and pulled them behind her.

Ana was in a state of continual orgasmic bliss as her tits were dragged back and forth across the desk, her cunt was filled, and her clit bounced off the edge of her Master's desk.

When TJ felt that Ana had endured enough and Madison had been taught a lesson he tore his cock from Ana's cunt as brutally as he thrust it in. "On your knees, whore," he commanded. Ana was lost someplace and took a moment to respond. "I'm done waiting Ana, on your fucking knees, NOW." Ana turned and slid to her knees, locked her eyes on her Master and opened her mouth.

THis was not a blow job, Gray thrust between her lips, deep into her ragged throat. Ana was happy as she didn't know if she had the energy to suck his huge prick. She swallowed him deeply, willingly. His heavy balls slapped gently against her chin as he sped up fucking her face.

For the first time Madison heard Gray moan. It was a deep vibration, desperate, ecstatic. Madison felt it as much as she heard it.

Ana felt her Master push deeply into her throat, against her soft cheeks. Suddenly, she started to work her tongue to help him finish. She bobbed her head in time as she tried to earn her reward. At that moment, Ana's entire world was in her mouth. She wasn't human, she was his property to be used. She was nothing but a useful hole.

He looked at Madison, "This is your fault,"

Ana moaned as Gray pulled out of her mouth and released all of his cum. Great hot spurts of his come rained down on her chest, her hair, he covered her face in his cum.. She parted her lips to it, writhing beneath the warm liquid as it oozed over her. Ana swallowed what she could. When she felt he was finished, she used her mouth to clean his cock, slid to the ground at his feet and slipped into a submissive nirvana. She would soon be asleep, her purpose fulfilled, her hunger satiated.

TJ scooped her into his arms, carried her to the sofa, tenderly placed her on it and covered her in a warm blanket. The dichotomy of brutality to tenderness made Madison's head throb with confusion. As Gray moved back to his desk to retrieve his pants he looked at Madison, "Get out of my sight or you'll be next." Madison felt frozen. "What kind of beast had she awakened?"

Finally she stood and slowly left Gray's office, her mind a tormented mess and her pussy a dripping, quivering mass of confusion. When the door closed behind her Madison leaned against the door before she slid to the floor and started to sob. If anyone would have seen her they would have described it as a soul wrenching, heart tearing cry.

On Friday evening, TJ accompanied Davey Thompson and two of TJ's old buddies from his time in Special Operations Command enjoyed a baseball game at Nationals Park. The tickets to see The Dodgers and Shohei Ohtani were impossible to find - unless 'you knew a guy.' Following the game the four headed to The Eastern - a wine and cocktail bar near Capitol Hill. Davey was trying to recruit the two Special Operations guys to the SSG team - and hopefully the eventual The Sentinel Group.

The atmosphere at The Eastern was electric as TJ and Davey Thompson, accompanied by two Tier 1 operators, Marcus Harris a Navy SEAL that was now an instructor and Lucas Ramirez from the Army's Delta Force, settled into a corner booth. Laughter and clinking glasses filled the air, a perfect backdrop to the vibrant energy that Washington, D.C. exuded on a Friday evening.

Unbeknownst to them, Madison Sterling had seen the events on the corporate calendar that many on TJ's staff had access to. Her curiosity, fueled by a few too many cocktails. Intoxicated and perched at the bar, she observed the quartet from a distance, her eyes fixated on TJ.

As the night wore on, the boisterous atmosphere continued to envelop the group until a commotion erupted at the bar. Madison, lost in her own world, hadn't realized the source of the disturbance until a young man who turned out to be a congressional aide, fueled by his own liquid courage, began pestering her relentlessly, including a not so subtle grope of her ass.

TJ, heard the commotion, looked up and saw Madison and her suitor. TJ looked at the three men, excused himself from the table and started to approach the scene unfolding at the bar. The congressional aide, unwilling to take no for an answer, continued his unwarranted advances.

"Miss, I think you're not appreciating the opportunity here," he slurred, his entitlement on full display. "Do you have any idea who I am?" His hand moved around to grip her thigh as he tried to spin her on the bar stool to face him.

TJ approached from the side, "Hey bub, I think that the lady has made it clear she's not interested. TJ asserted, his tone leaving no room for negotiation.

The aide, momentarily taken aback by TJ's authoritative demeanor, scoffed, "Who do you think you are?"

TJ's eyes hardened, a flicker of danger dancing in their depths. "I'm someone who doesn't tolerate disrespect. Now, step away."

The intervention left the aide with no choice but to retreat, muttering under his breath. TJ turned to Madison, concern etched across his features.

"Are you alright?" he asked, his voice a soothing balm.

Madison's eyes were angry, "I am perfectly capable of taking care of myself, thank you very much."

TJ smiled, "Okay, you do you boo."

Gray returned to his comrades, but his eyes stayed attuned to Madison, the aide and the aide's buddies who had busted his balls for not standing up to the guy. More rounds were ordered and more shots were downed. Alcohol does not usually make wise choices.

Eventually, Madison excused herself from the bar and headed down a hallway to the restroom, the aide seized the opportunity and followed her down the hallway. In the narrow corridor, he grasped Madison's shoulder and pushed her against the wall, his unwarranted advances escalating.

"You should've appreciated the opportunity, bitch," the aide hissed as one hand went to her throat and the other to the silk blouse encased breast. "I was going to do this the nice way, but you sit at the bar in an expensive silk blouse with no bra and tease me like that, I can do it the hard way. One way or another you are going to get fucked tonight."

Before Madison could respond, TJ rounded the corner enraged. Every ounce of his protective nature was on full display. "Hey asshole, you had your one warning. We are done here." The air crackled with tension as the two men locked eyes, each emanating an energy that was impossible to ignore.

In a heartbeat, TJ's instincts took over. Gray stepped forward, grabbing the aide by the collar, and pinned him against the opposite wall. One hand on his throat. The predatory intentions that had fueled the aide's actions were now met with a powerful counterforce.

"You've crossed a line you can't uncross," TJ growled, his voice a low rumble that echoed through the hallway.

The aide, now on the receiving end of undeniable force, stammered incoherently, his bravado evaporating in the face of this unexpected opposition. TJ's grip tightened, a silent warning that reverberated through every fiber of the man's being. "You have two choices as to how this ends. It may be best if you make the decision instead of that cheap whiskey you've been drinking."

As quickly as it had begun, the confrontation ended. TJ released the aide, who stumbled backward, a mix of fear and humiliation etched across his face. Madison, her eyes wide with a combination of gratitude and awe, watched as TJ stood between her and the aggressor.

"Leave, not just the hallway, but the bar. You and your friends have 3 minutes to pay your tab and get the fuck out of here before you get hospitalized." TJ commanded, his voice cutting through the tension.

The aide, without a second glance, retreated down the hallway. TJ, his gaze still fixed on the retreating figure, turned to Madison with a reassuring presence, a silent promise that she was safe under his watchful eye. "Come on, I'm taking you home."

TJ pulled Madi down the hallway, apologized to the group as he told them about the aide and his group of buddies. As TJ opened the car door for Madison she turned to him, wrapped her arms around him and kissed him. TJ broke the kiss as soon as he could create distance between them.

He looked down at Madison, "You're drunk."

Madi giggled, "I know, but I'm cute when I'm drunk."

As they started on the journey home, the silence of the Lexus was punctuated only by the soft hum of the engine. Madison, however, seemed determined to break the stillness. In the dimly lit interior, her attempts to capture TJ's attention manifested through slurred words laden with innuendo and suggestive flirtation.

"TJ, you're so strong," she murmured, her words dripping with a veiled meaning. "I bet you could handle anything."

TJ, his eyes fixed on the road, remained stoic. "Just trying to get you home safely, Madison."

Undeterred, she leaned closer, her fingers tracing an imaginary path along his arm. "You know, you're not like other guys. I can tell you're different."

TJ, steadfast in his resolve, kept his hands firmly on the wheel. "I am that."

Madison's laughter rang out, an unsteady melody that danced through the car. "I've never known anyone like you. You are mysterious. You've got that whole strong, silent thing going on."

Her attempts at seduction continued, each remark and touch more persistent than the last. TJ, however, maintained his focus on the road, navigating the twists and turns with precision. Madison's intoxication had clouded her judgment, and TJ, who was not amused, remained resolute in his duty to get her home safely.

TJ finally looked at her, "What's your address?"

Madison giggled, "Guess."

TJ shook his head as he looked at the young woman, "Don't you dare throw up in my car."

Madison leaned in, "Or what, you'll spank me? Maybe I liked that."

TJ shook his head, "You are not Ana, just stop."

Madison purred as her hands slid down to her pants, "Watching you with her was terrifying, yet I've never been more turned on. She was helpless, and you just took what you wanted. I should think that is wrong, but it's so fucking hot." Madison slipped her hands down her slacks and slipped a finger deep into her dripping wet pussy. When she pulled her finger out she put it near TJ's mouth, "Taste what you do to me."

"Madison, stop. You're drunk," he replied as he took her wrist in his hand and moved her finger away.

Madison smiled as she licked her own juices from her fingers. "Young, fresh, just waiting to be fucked by a real man." When she looked up again she saw Gray pulling into his own driveway.

As Madison stumbled out of the car, she gushed, "You must really like me, TJ, taking me to your place and all. Rescuing me and everything."

TJ, guiding her towards the door, responded with a measured tone, "This is for your safety, Madison. We'll talk when you're sober."

TJ guided Madison into the house. Ana, ever dutiful, stood ready to assist. Madison, in her intoxicated state, seemed both disoriented and strangely fixated on the dynamic between TJ and Ana.

As TJ settled Madison onto a couch, he instructed Ana, "Take care of her, Ana. I need to make sure everything's secure outside."

Ana nodded, "Yes, Sir," her gaze meeting TJ's with an unspoken understanding. As TJ left the room, Madison's hazed eyes followed him, a mix of confusion and arousal dancing within their depths.

Ana, with a gentle touch, tried to ease Madison's discomfort. "Let's get you comfortable, Madison."

Madison, however, couldn't seem to tear her gaze away from TJ's retreating figure. "You know, Ana, he's everything isn't he? Strong, forceful, demanding. He can go from gentle to feral in an instant. The things I have watched between the two of you..." she let her words drift off.

Ana, maintaining her composure, helped Madison settle on the couch. "Madison, you've had a bit too much to drink. Let's focus on getting you cleaned up and ready to sleep."

But Madison, fueled by liquid courage, continued her commentary. "I've seen the way he looks at you, Ana. The way you serve him, they way he fucks you. God, it's so fucking hot. You do know he's fucked others in the office too, don't you."

Ana, smiled, "Of course I do, dear. Sometimes in front of me. TJ is a rare man that I feel proud watching him with other women, watching their eyes roll back in their head, their toes curl because he is everything to many people. Men want him to fuck their wives, even your uncle has asked him to fuck your Aunt after he dies."

Madison, undeterred, smirked. "Uncle Tight Ass? There is no way he would allow that."

Ana smiled, "Yes, he does."

Madison's laughter echoed through the room, a mix of intoxication and boldness. "Holy shit, so that means I'm the only one he hasn't fucked or isn't going to fuck at some point? That's not fair."

Ana, maintaining her professionalism, sighed inwardly. "Madison, this is not a conversation for now. Let's focus on getting you some water and helping you rest."

Ana had lingerie and sensual sleepwear but Madison was a little broader in the shoulder and hips so she had to find one of TJ's t-shirts for her. As Ana helped her undress Madison moaned, "Do you think he would fuck me, Ana?"

Ana smiled, "It's not for me to answer for TJ - but in my opinion you need to prove to him you deserve that." Ana sat back, "I know from your background this may sound foreign to you but a man like TJ with a cock like his is a gift that a woman needs to earn." Ana smiled, "Most women think that agreeing to sex is a gift to the man, and with many men that may be true. However, with TJ it's quite the opposite. As you have seen, TJ cums once while every partner he has ever been with cums over and over and over again. He is a demanding lover, but he gives pleasure, even when he's taking his own pleasure from his partner."

Madison stood and lifted the shirt over her head and dropped it to the floor, "I'm not pretty enough am I?"

Ana shook her head, "You are pretty enough, it's your attitude that isn't pretty. You think you are special, that you deserve things you haven't earned. Then when you don't get your way you pout and threaten. Please understand this, IF he ever fucks you for the rest of your life you will compare every partner to him - while IF he fucks you, you will be just another well fucked partner - he will be your everything, the measuring stick and you will be just a warm wet hole."

Madison shivered, "That sounds disgusting, but look at how hard my nipples are and how wet my pussy is. I want to be that, just once. Would you help me?"

Ana smiled, "That's why you set tonight up isn't it?"

Madison's eyes flashed mischievously, "No, no it isn't"

Ana reached up to the young woman and took her nipples between her thumb and pointer finger, "Don't you dare lie to me."

Madison panted, "Okay, it is. I'm not nearly as drunk as I pretended to be, I just have to know what it feels like to be taken like a lioness on the plains. Will you help me?"

Ana sighed as she looked down at the full mane of hair that surrounded Madison's pussy, "First, this must go."

Madison's eyes got large, "I'm not going to shave the essence of my femininity for anyone."

Ana shrugged, "Suit yourself, then no, I will not help you. To deserve my Master's cock, then there must be sacrifice on your part. Good night Madison."

Madison watched as Ana opened the door, walked out of the room and closed the door behind her. Madi ran to the door, "Ana, wait! Please, come back."

Ana stopped and turned, she pointed to the bathroom, "Go in there, turn on the shower, and wait for me."

Ana helped Madison take a long shower, washing her hair, her body, and the hair around her mound. She created all of the steam and moisture she could before she allowed Madison to leave the shower and return to the guest room.

Ana followed her with a bowl of hot water, a washcloth, towel, scissors, a bowl with shaving soap and a badger hair brush along with a razor with more than one blade. Ana carefully trimmed all of the hair that had hidden Madison's pussy from the world. Following that she retrieved the washcloth from the basin and wrung it. Ana shook out the washcloth and covered Madions's fresh stubble. The moist heat brought her arousal to a new level; one she had not expected.