The Long Road to Ruin Ch. 37-39

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"I'm not Catalynne, but I am very naughty. Your little bitch is dead," Shiloh hissed, slamming down upon him. She rode him hard and fast despite his efforts to free himself. Harsh growling noises came from his throat intermixed with heavy pants then vulgar muffled curses. "And you're next."

He struggled harder, jerking his arms in attempt to free them from the bonds. Shiloh placed her hands on his shoulders, balancing her weight carefully, while rocking her hips seductively. Her breath came out in labored puffs and sweat poured down her face landing on her breasts. Her inner imp surged mischievously. She grinned wickedly then slapped his face, then a second, and third time. Simon grunted and growled, his upward thrusts meeting hers violently. A vein bulged on his forehead. His face turned beet red then he gave a muffled howl. Shiloh felt him explode inside her; she then squeezed her channel around him.

He collapsed limply, no longer fighting the bonds. She then she pulled away, settling down upon his torso. She could feel his deflated member against her backside, but ignored it as she dangled her heavy breasts in his face. "You surprise me, Simon," she purred. "I never pictured you a masochist, and a submissive one at that."

He struggled weakly, snarling incoherent words around the panties stuffed in his mouth.

"Don't deny that you liked it, I know you did, you can be honest with me. I won't think any less of you than I do already," she murmured softly in his ear. "Do you want to know the truth, dear Simon? I'm not Lady Alcott. Nor am I a whore. I've never accepted money for sex. I've killed men who've made the mistake of calling me that. Do you want to know who just fucked you? Nod your head, Simon. Do you want to know who I am and just how privileged you are to have had me? I said, nod your head."

She slapped him not once but twice, as hard as she could. Red stripes blossomed upon his face and he bellowed from the pain. His lips trembled, his eyes shining brightly with unshed tears, as she pulled her blood stained sword. He nodded at her frantically while resuming his struggles to free himself.

"That's a good boy, Simon. You learn quickly. I could be persuaded to keep you around as my fuck toy, but I'm afraid someone wants your head, badly. Unlike me, it's not the one that hangs so pathetically between your legs." Shiloh ground herself against his belly, smearing their combined release into the hair of his groin. "Perhaps it'll make you feel better to learn that a member of the Betancurian royal family had your dick inside her pussy. Yes, Simon... I said royalty. That's what I am. My name is Princess Shiloh Cheval Aurelius. My father was King Rolan III. He was murdered by your country's military; murdered by Commander Arto Benthur. My vengeance begins with you, dear Simon. Once I've killed you, I'll make it my mission to kill Commander Benthur. No one will be the wiser that the royal Betancurian princess is still alive. Your soldiers are as pathetic as you. Countless numbers have fallen to my sword and I have only just begun. Countless more will fall as I forge a path, stained with blood to reclaim what is mine." Rising up, she clutched Darkstar in both hands. Beneath her, Simon struggled fruitlessly. His muffled sobs were music to her ears, "An eye for an eye, blood for blood. Vengeance shall be mine."

It was then she leapt from the bed seeking Oathreaver. Brandishing the whip, she spoke the words, "Swift death to those who have wronged me." The crack of the whip sizzled within the air before she brought to bear against the tender flesh of his groin. He howled loudly. Again she struck him, raising a bloody red gash across his abdomen. Her next strike hit his chest, just over his heart, "Die, scum!"

Setting Oathreaver aside, Shiloh gripped then plunged Darkstar through his chest, into his heart. Yanking it out, she swiftly slashed his throat. Blood gushed from the grisly jagged wound. She plunged her hands into it, and then smeared it over her body. "Take this offering of blood as a pledge of my continued loyalty. I deliver his soul onto you to be kept for all time."

Hefting a halberd from the nearby weapon rack, she brought the blade down against his neck with all the strength and force she could muster, severing his head from his body.

Her inner imp cackled, she then spit upon the remains of his body, after she painstakingly carved the word 'WHOREMONGER' upon his chest. "I'll see you in hell," she quipped as she dropped Simon's severed head into a burlap sack. She then stowed it within the portable hole she now always carried on her.

She grinned then removed the pieces of Simon's armor from the stand it rested on. She bound her breasts as tight as she possibly could then slipped into her catsuit before layering Simon's armor over it. She then left the room, shutting and locking the door behind her.

Once again she encountered no guards as she slipped through Simon's office then into the corridor. Upon a quick search, she located Jero's bedroom then slipped inside. She drew Oathreaver, making another oath. She slashed the coiled whip against his throat, crushing his windpipe beneath the impact, then delivered his soul to her most revered Lord. Quickly she harvested his head from his body as well, intending it as a bonus to Jacia.

Smartly, she covered her face and head with Simon's helm then draped his rich red cloak about her shoulders before ducking out a back entrance. No one stopped her on her way back to the hideout. As she approached then entered Drago's Warehouse, she removed the armor then stowed it away. Only then did she knock and give the password that would gain her entry to the lower levels.

"Shiloh," Drago nodded curtly.

"Drago," she replied before turning her attention to the man who stood near him. "Tony."

"Shiloh, it's a pleasure to see you, doll. What brings you here tonight?" Tony asked, leering at her.

"I've just come off a job for Jacia and was headed to the hideout to give my report," she preened before him, clenching a hand on her outthrust hip.

"Care for some company?" Tony asked, arching an eyebrow at her.

"Would love it," she grinned then held out her hand to him. Together they crossed the sewers, making small talk as they walked along. As they neared the guild house, Tony stopped her.

"I'm having a big party at my house in celebration of the monumental job I pulled off for Nathan. I would like you to come. I know about you and Essex. We all do, but he's out on an important job right now, so I figured I could stand in for him. No strings attached, honey, what say you?"

Shiloh grinned. "I'd be delighted to come to your party. We can explore the no strings attached aspect," she leaned in, gazing into his deep blue eyes then planted a kiss on his generous mouth. "I'll see you later."

"Wear something sexy. I want you to look hot," he purred before he embraced and kissed her. Once he let her go, he walked away, disappearing among the shadows of the sewers.

Shiloh smirked, continuing into the hideout, then approached Jacia. "I have a couple something's for you."

"Do tell," Jacia grinned maniacally. "Though I'm not sure whether I should be surprised or pissed off that I lost money betting against you. Truthfully, little princess, how'd you do it? What deal did you make to harness the skills to put Vico down?"

"I defeated him with my own skill. I made him fight my kind of battle, and I used my wits to stay ahead of him. He was far too overconfident of victory and too slow for me, that's how he fell to my blade. From what I hear, the fucker is also too stubborn to let himself properly heal. I hope he dies from it."

Jacia's eyes flashed. "Pretty words you spew, but none that I'd believe. You know all you've done is angered the beast. He will have his vengeance against you, little princess, and I wouldn't want to be in your shoes when he does."

Shiloh rolled her eyes, "Forgive me if I refuse to tremble, but he doesn't scare me and neither do you. Now, would you like the severed heads I have for you or not?" Shiloh opened the portable hole then removed the burlap sacks which contained the heads of Simon and Jero. She pulled them forth. "This is one Lord Simon Lyonson and this one is his good friend, Jero, who from what I gather is an officer in the Dhorn army."

Jacia grinned malevolently then accepted both of the severed heads. "I so love it when you give me head." A cold chuckle slipped from her lips. "I'm amazed you succeeded so quickly. I have your reward." The black clad hooded assassin pulled forth a wicked looking dagger then a heavy sack of gold. "The dagger I bartered from the man who forged it. He named it Bloodlust. I think it suits you perfectly. He told me it has the power to cause horrific unstoppable bleeding from its wounds. Quite nasty if you think about it."

Shiloh's grin matched Jacia's as she held the dagger in her hand. Then she tilted her head toward the small storage room off the left of Jacia. "Come with me," she stated then gathered Jacia's hand in her own. Shiloh pulled the assassin along with her then closed the door.

"What's in your head, Shiloh? Thinking of using that against me?" Jacia sneered then twirled a small bejeweled knife within her fingers.

With a shake of her head, she pulled Jacia closer. "You might benefit from an association with my Lord Bastian. He would welcome one such as you into his service."

Jacia pursed her lips thoughtfully then reached for a nearby leather bound book. She opened it to the middle and skimmed the pages. "Bastian, Lord of Lust, Hedonism, and Vengeance," she spoke aloud. "Once a demon, that rose to the rank of Lesser Deity by defeating Shalazar, the original holder of that particular portfolio. I know who he is; his petty powers pale in comparison to those held by the one Vico and I worship. Nice try, little princess. Thank you for the heads. I'll let you know when I have another job for you."

Shiloh glared furiously then flipped an obscene gesture towards Jacia's retreating back as she watched the assassin walk from the room. "You tried, little one, I appreciate your efforts, but could have told you she wouldn't be so easily swayed. Her Lord is indeed powerful. I've long lusted for what he holds dear. It's one reason that killing the blackguard would have been so sweet." Shiloh calmed as she heard Bastian's voice in her head. "But you were right in your thinking. I would've enjoyed having her in my flock."

Shiloh left the small room, ignoring Jacia's blatant sneer. She crossed the main room then found an empty bunk bed she could sleep on. Shiloh sighed wistfully. I have my own apartment, yet I'd rather sleep anywhere but there. Too many memories haunt me. Sleep was a long time in coming.

O.O

With Tony's party set for that evening, she looked through her stash of dresses held within the portable hole. Nothing appealed to her though; she knew she'd have to buy a few dresses. Shiloh left the hideout behind after perusing Dalino's stock then made her way through the sewers to the northern ward of the city. A smile crossed her face as she dug out Simon's armor. This could come in handy. She could wander around and no one would think twice about it. She didn't know if her restriction to lay low was still in effect or not, but she sure as hell didn't want to find out either.

Quickly she bound her breasts once more then donned to armor and cloak. She then climbed the ladder to the street surface and began to casually stroll up Acorn Street. Gaston's soon became her destination. She entered the fine establishment then stopped just inside the door. The women shopping within scattered like squawking chickens running from a hungry fox. Shiloh raised an arm then barked in her deepest voice, "As you were!"

She then stalked over to a recently vacated rack of dresses. Scanning through them, she pulled a satin burgundy creation and a silky low cut black mini-dress from the display then moved over to a nearby mirror. Uncaring of what everyone else thought, she held each of the up before her. Then she picked up a few more every day dresses and headed over to Gaston.

The tailor gaped at the Dhorn soldier before him with a shocked expression on his rather effeminate face. "Will that be all?" He asked as he quickly recovered his voice.

"Ask me no questions and I shall tell you no lies," Shiloh quipped in the same deep voice she'd used previously. She drew forth the heavy bag of coins Jacia had given her then handed it the Gaston. The tailor sputtered and promptly stowed the soldier's purchases within a garment bag before handing it over. Shiloh gave an exaggerated bow then left the establishment behind. She made her way back to the southern end of the city then headed toward the house Essex had appropriated. She knew he wouldn't be there, but knew it was a good place for her to spend the day pampering herself before heading to Tony's place. It wasn't that she wanted to look good for Tony's benefit, she wanted to show him what he had no chance in hell of possessing.

Upon bathing then recoating her fingertips and toenails with a coat of pale pink polish, she coifed her hair into a sassy up-do with tiny little ringlets falling softly over her bare shoulders. She slipped the silky black stocking up over her legs then fastened them to garters attached to a lace corset which made her small waist look even smaller.

Over the corset, she pulled on the low-cut black silk mini-dress. Upon adjusting her cleavage, she completed her ensemble with pair of low heels. Then she artfully applied cosmetics to her face before dabbing a sensual jasmine scented perfume between her breasts. Shiloh was ready.

O.O

At the appropriate time she made her way to Tony's. She lifted the heavy brass door knocker, making her presence known. An older man opened the door then ushered her in. "You must be the young lady Master Tony is expecting. Follow me, my dear girl. Tony is in his bedchamber."

"Bedchamber," Shiloh repeated, "You're leading me to his room?"

"Master's orders, now come along, dear child. Tony will take good care of you. His girl's usually rave about his treatment."

Shiloh cocked an eyebrow at the stoop backed grey haired older man leading her up a grand staircase to the upper floor. He stopped before a pair of dark walnut doors then knocked loudly. A moment later, he opened them as if on cue. "Master Tony, I hereby announce..."

"Lady Shiloh," she hissed under her breath loud enough for the butler to hear.

"I hereby announce Lady Shiloh," he repeated then bowed deeply.

Tony's lips twitched as he stepped out of large copper tub then reached for a fluffy cotton towel. "Thank you, Sampson. That'll be all for now. Make sure the wait staff is prepared for our guests later this evening. You're dismissed."

Sampson bowed a second time before exiting the room then pulling the doors shut behind him. Shiloh smiled at Tony who stood drying his body. He grinned brightly at her. "I'm glad you could make it, my lovely."

"Delighted to be here," Shiloh replied then beamed a brilliant smile. She moved toward him, her walk a sexy prowl. She stopped beside the large four poster bed then leaned against it. Her eyes devoured him, taking in every inch of his bare damp flesh. "Drop the towel. I want to see all of you."

Tony smirked then tossed it aside, exposing his nude form to her probing gaze. "I gather you're the type to dispense with the formalities. I like that. I like a woman who knows what she wants and is bold enough to take it."

"I see no reason to beat around the bush," she purred before she moved to sit upon the edge of the bed. She leaned back, thrusting her breasts out while spreading her thighs, then allowed her short skirt ride up far enough to expose her bare pussy. Boldly she dipped her hand between her legs then spread her lower lips. Further inward she delved, sliding her two longest fingers inside her channel just enough to coat them with her juices. She then pulled them out and brought them to her mouth, making a show of licking them clean.

Tony groaned then wrapped his hand around his cock, feeling it stiffen and lengthen as it filled. He stroked himself, letting the foreskin hide then reveal the dark red plum shaped knob at the tip of his member, until it grew to full aching hardness. A groan slipped from his lips as he gently squeezed the head then felt his palm moisten from the pearl of precum that slipped from his slit. "Off the bed," he rasped deeply. "And strip..."

Shiloh obeyed him completely. She stripped down to her corset and stockings, baring the sight of her creamy breasts and her nether lips to his gaze. "Do you like what you see, handsome?"

Tony grinned then pulled her into his arms. His hands immediately sought out her lush mounds, fondling and squeezing roughly. Then he pushed her down to her knees before him. "Suck my dick, little bitch."

Shiloh's eyes flashed as she locked her gaze with his. He inclined his head, motioning to the cock bobbing before her. Tony hissed when he felt Shiloh take hold of his balls, cupping them in her hand, rolling them gently. She squeezed him just below the crown of his shaft and he groaned. She stroked him once then twice and he felt the first swipe of her tongue on the head of his cock. She lapped at the slit before swirling her tongue over the broad surface. She engulfed the head in her mouth, slowly sliding her lips over his cock. Almost immediately he felt lost in a haze of heat and arousal. He wanted to reach down, bury his hand in her hair and urge her to take more of him into her mouth, but couldn't move. "Suck it, bitch" he demanded then snapped his hips. He hit the back of her throat and moaned loudly when she swallowed him. Her throat clenched, then relaxed around him. Her head bobbed up and down, while her hand fondled his balls, tugging gently. "Yes, slut, just like that, faster, harder, gods...feels so good."

His hips moved up and down faster, his hands finally sinking into her hair, nearly destroying her up-do. He was so close, on a knife's edge.

"Fucking hell," he cried out when he felt the pinch of her hand on his nipple. Electricity shot through him, his stomach clenched. His balls, which she had released to grab his nipple, drew closer to his body as the fire danced along his spine. His cock twitched in her mouth, he was about to come. He opened his mouth to warn her but didn't get the words out in time. He spurted his seed into her mouth. His hips continued to pump until his balls were empty.

Panting hard, he slowed his movement. Her tongue licked up the last traces of his seed before gently letting his now flaccid cock slip from her lips. With great care she cleaned him up before drawing herself to her full height. Rage flashed in her eyes at his arrogant attitude toward her. She drew her hand back, slapping him across the face once then a second time on the backswing.

"Fucking cunt," he growled then grabbed hold of her upper arms. Tony shook her violently then shoved her towards a nearby low backed chair, forcing her to bend over it. The top rail bit into her stomach while he spread her legs wide then palmed her mound, thrusting his fingers inward and stroking her dripping pussy, seemingly from the inside out.

Shiloh's protest died in her throat, turning into a loud moan when he poised the tip of his cock against her pussy lips. His blunt cock-head grazed her slippery folds before it dove into her needy channel. He thrust into her in one swift movement. Shiloh screamed. Gods, was he big! Fuck, too big! She felt lightheaded when he forced her tight channel to take him whole. She gasped again, feeling the air around her thinning. It'd been a good while since she had been stretched so deliciously. Her pussy grew instantly wet. Fuck, how she craved every inch of him. So deep and nasty it hurt, but it felt so good after he ground himself to the root.

1...345678