The Long Road to Ruin Ch. 04

Story Info
Sexual Education
6.9k words
4.62
22.5k
6

Part 4 of the 45 part series

Updated 11/02/2022
Created 09/16/2009
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
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

Disclaimer: This fanfic is based off the Neverwinter Nights community module by the name of "A Dance with Rogues" created by Valine. I fell in love with this story and felt compelled to write something that compliments it. This story is rated Mature (NC-17) for explicit content and graphic violence. All characters except Shiloh, Bastian, Rhys, Nicca, Essex, and Narev are property of Valine.

Please vote and leave feedback!

Sexual Education


Shiloh passed the rest of the daylight hours doing the shopping she needed to do, visiting Talana's for the required lingerie, and wandering the marketplace in Northern Betancuria. As dark approached she made her way into the southern part of the city, walking this time instead of taking a ride on the ferryman's boat. She skirted the Isle of Men and walked along the long stone bridge. Walking slowly, she stopped on the bridge to stare down at the water. She liked the way the glow from the torch lamps played upon the water's surface, reflecting fissures of light. It was so pretty.

She continued on, passing a market stall and Herol's Imported Goods. She paid little attention to the beggar as she hurried past him and The Wildcat, making her way to the dockhouse.

She crept inside, making her perch on one of the numerous crates stored in the building. There she waited for Rhys to show up. She hoped he wouldn't be a no show. She really wanted to learn how to please a man. She needed to learn. She wanted to be able to give Caron a real reason not to look at Trissa. If Shiloh could be with him as the other girl had been, but make it better, perhaps she'd win him. How could he say no to that? Certainly he wouldn't.

A pair of hands gripping her breasts drew her out of her thoughts. Shiloh let out a loud gasp and struggled as the hands dipped into her shirt, plucking her nipples. "Unhand me, now!"

"I thought you wanted this, little girl?" A voice purred against her head as the fingers squeezed the full globe of each breast.

"Rhys?" She tilted her head back of the way and looked up at him.

"The one and only." He quipped as he went back to tweaking her nipples. Shiloh let out a raspy moan. The mixture of pleasure and pain zinged through her. "Like that, sweet thing? You ready to get fucked?"

"Is that what you want to teach me this night?"

"Uh-huh, but first I want you to strip for me...slowly." He removed his hands from her breasts and stepped back a few paces, watching her as she hopped off the crate. Her hands took the place of his, pulling on her nipples through her low cut top. She caressed them, her eyes fixed on his. Then she pulled it over her head and tossed it to the floor, baring her breasts to him.

She repeated the act before him, plucking the hardened buds as a soft moan escaped her lips. She could feel herself growing wet between her legs as the ache......for something inside her intensified.

Her hands dropped to her waist and she lowered her eyes as a blush colored her cheeks. Slowly she tugged her skirt down her legs and then stepped out of it. She looped it on her dainty foot and flicked it in his direction. Then she gracefully kicked off her shoes and rolled her stockings down her legs, turning away from him as she bent, showing him her bottom.

Rhys gave an approving whistle and grabbed her from behind. He hauled her back against his crotch, rubbing the thick bulge against the crack of her ass. He sniffed the air, taking note of the pungent musk coming from between her legs. "Fuck yeah, little bitch. There may be hope for you yet."

Shiloh grinned and wiggled her bottom against him, hoping he'd like that. A low groan was his only reply. He let her go and pushed her against the crate.

"Now, undress me."

Shiloh looked back at him as a nervous shiver coursed through her. She'd never seen a man's entire naked body. Turning to him, she gripped his tunic and began to pull it up over his head. She had to stand on the very tips of her toes to bring it up over his head since he towered over her by at least a foot or more. Once it was off, she let it drop to the floor and she ran her hands over his wide shoulders, and then down over the corded, sinewy muscles of both his arms.

From his arms, she moved them to his chest, threading her fingers through the sparse hair that covered most of his pectoral muscles. She smiled as her fingers brushed his flat male nipples, eliciting a tiny groan from him. "Lick them!" Rhys hissed at her, his hand flew to the back of her neck and pushed her mouth toward his chest.

Shiloh obediently complied as she fastened her mouth onto one of them. She ran the flat of her tongue over his large nipple before switching to the other one.

"No, stupid girl. Let me show you," he growled and knelt before her. His mouth fastened on her nipple, giving it a lick to wet it before twirling his tongue over the elongated point. Then he began to suck, drawing the nub between his lips. His teeth nipped and grazed at her while he fondled the other one, gingerly pulling on its tip.

Shiloh groaned as a frisson of heat coursed from her breasts to settle between her legs. She tossed her head back, allowing a cry of pleasure to escape her. Rhys pulled back from her.

"Do you like that?"

"Ohhhh yesss!!!"

"You try..." he hauled her back up against his chest.

She eagerly copied what she thought she had felt, sucking him into her mouth. She nipped the tiny point before using her tongue on it. She licked each one before continuing her trek down his body.

Her hands reached the waistband of his trousers, and she eyed the burgeoning bulge straining against the laces. Her hands trembled slightly as she smoothed one palm down over him. He moaned loudly. "That's it, honey..."

She deftly unlaced his pants and slowly drew them down his hips, being careful not to yank them over his hard cock. When she had them at his knees, she stopped to remove his boots. He kicked his pants off the rest of the way and proudly stood before her. She eyed him curiously, running her hands over the lower half of his body, familiarizing herself with all his hardened muscles. She could easily tell he was used to doing hard manual labor, his bulging muscles and work calloused hands were a solid testament to it.

"Enjoying yourself, sweet thing?" Rhys murmured, as he leisurely gazed down upon her.

She blushed profusely, embarrassed to be caught staring at him. She nodded her head at him. "You are beautiful..." she whispered.

A loud laugh sounded from him. "No, sweet thing, you are the beautiful one. Now since you are down there, you can learn to properly suck my dick."

Shiloh gasped and gulped, "I...thought...you...wanted to...fuck me."

"I will, all in good time, sweetness." He buried his hands in her silky hair and made a noise of contentment. "First, relax, sweet thing. This'll be a piece of cake once you've learned a few things."

Shiloh turned bright red, her eyes lowering to the ground.

"Look at me, honey," Rhys put his hand under her chin and tilted it up. Shiloh gazed up at him. "Listen to me..."

She nodded.

"Relax! I'm not going to jam my cock down your throat until you gag. Do as I say and you'll do fine."

She nodded again, feeling the urge to trust him. "I am ready," she spoke, licking her lips.

"That's it. Wet those gorgeous lips. Make sure your mouth is moist. I'll tell you this, sweetness, a lot of saliva in your mouth is a good thing." He palmed his cock and held it up to her. "Part your lips, honey, and take me inside."

Shiloh did as he directed, placing her hand on his and guided the head of his cock into her mouth. He gasped as it passed through her lips and moaned softly. "Yes, good, honey. Now lick the tip, swirl your tongue around it like you are licking an ice cream cone, but not too fast. Ahhh...yessss...honey."

Shiloh did as he directed, twirling her tongue around the head, getting a taste of him. It wasn't a bad taste, but part of her wished he had washed himself before he'd come to her.

"Now, run your tongue around the ridge of the head, and flick your tongue over the ridge that is V-shaped, sweetie. Ahhh....yessssssssss.....ahhh...that's it," his voice came out a tad bit strained as he fought the urge to buck his cock down her throat, "Good girl."

Shiloh pursed her lips around the head and began a gentle sucking rhythm on the head. She swirled and licked, sucked and flicked her tongue around the head and down the ridge to the sensitive underside. There she placed a gentle suction and Rhys moaned heartily.

"Slowly take an inch or two inside your mouth and gently grip the base. I want you to stroke the base up and down. Not too slow, but not too vigorous yet, either. About like this," He covered her hand with his and guided her strokes. "Good, honey. You are doing good."

"I want to you to run your tongue along the shaft. Suck it on the way down and lick the underside in a flicking figure eight motion on the way up. Ohhhh...yeah, that's good....good," Rhys moaned and fed her another inch.

Shiloh gazed up his body and their eyes met. She noticed his eyes were slightly glazed, a pleased smirk on his face. His head lolled back, his eyes closed as a moan escaped his throat. His hand came to rest on the top of her head in a reassuring way.

She licked the underside of his cock in a long slow stroke, working her tongue in the way he had told her to, making tiny crisscrossing figure eights.

"A little harder and faster now, honey!" A mighty groan escaped his lips and he eased another half inch in to her steamy oral cavity. He figured that would be all she could take for now. He placed his hand over hers and guided her strokes, making them a tad bit more intense.

Shiloh licked the vein thick underside of him in little flicks as she slid back up toward his head. She moved her hand back up in unison with her lips, making sure her hand matched the rhythm of her sucking mouth. Rhys groaned in appreciation and let his hips involuntary buck. She felt his cock twitch against her licking tongue.

Then he pulled out of her mouth and lifted her to her feet. "You are going to be one hell of a cocksucker, honey, but I'd rather spill my cum in your sweet cunt instead of your mouth."

Shiloh cracked a shy smile at him and let him lift her back onto a crate. He positioned her bottom on the very edge and spread her legs open, stepping between them. He dropped his fingers to her bush. "You have a pretty cunt. Though, I have to admit I'd much rather prefer a bald one. You should shave it for me."

A blush reddened her cheeks. She had never heard of such a thing. She didn't have time to dwell on it. She cried out as he touched her lower lips, his fingers parting them. He dipped into her wetness, smearing her juices onto the tip of his cock. "Holy fuck, you are soaked! Sucking cock must work for you."

"Touching you started it," she confessed and spread her thighs wider. "I'm surprised I want this as much as I do."

"I'll be easy on you, for now, but I swear one of these days, I will fuck you black and blue, honey!"

"I'll be looking forward to it," she whispered as her face turned red.

"You are very wet, now, but for future reference, if you are not wet and still dry, spit in your hand and lube the guy's cock up. It'll make the penetration easier on you and him."

Shiloh nodded at him as he wrapped her legs around his hips.

"You ready for my big dick? You ready to get fucked?"

She glanced down her body at the large cock poised at her nether lips. She shyly rocked her hips and reached out to him. "Would you kiss me before you enter me?"

A smile cracked on his handsome face. His hands delved back into her hair as he pressed his upper body against her. His lips met hers and he pushed his tongue into her mouth, kissing her deeply. His mouth devoured hers.

He placed his cock at the entrance of her slit and slowly pushed into her tightness. It was a good thing she was wet. His girth stretched her wider than she'd ever been stretched. She whimpered against his mouth. He sank into her as slowly as he could manage. He could feel her warm walls give to accommodate his size, feeling them grip and suck. He groaned, reveling in the feel of her hot pussy.

She let out a tiny moan as he buried himself to the hilt, the head of his cock hitting bottom deep inside her.

"My cock is eleven full inches when hard, and you have engulfed it, honey," he pressed his balls against the bottom of her crack, nestling them against her wet warmth. His fingers dipped into her cleft, exposing her swollen clit to the air. "This, my sweet, is your clit. It'll bring you the sweetest pleasures that you can imagine when played with."

He stroked a calloused finger over the hood and she shivered with delight as he found the mass of nerves. "Try to contract your inner muscles as I thrust in and out of you. It will heighten your pleasure...and mine."

Rhys began a sweet rhythm of thrusting and stroking her clit. Tiny moans of delight came from her mouth as she arched her back and let him do as he wished with her. He increased his tempo, alternating deep and shallow thrusts to maximize her pleasure. Shiloh was soon shaking and screaming while he pounded into her dripping pussy.

Soon she exploded around him, drenching him with her female juices. The contractions of her snatch sent shivers up his spine and he howled, finally giving into the pressure that threatened to erupt from his balls. He spewed his load into her, thrusting deeper and harder as his cock twitched and his balls emptied into her.

He leaned down against her, pushing his softening cock in all the way, and rested his sweaty brow between her breasts. Shiloh gasped at the feel of his cock head pressed so snugly against her inner core. "Rhys?" she gasped, "What happened to me? What did you do to me?"

A laugh erupted from his lips as he gathered his wits about him. "I'd say I gave you your first orgasm. And by the gods, your pussy is divine!"

Shiloh gasped and fell back against the crate. Her body hadn't stopped its trembling yet. Her limbs twitched, shuddering from the pleasure he had bestowed upon her.

"You've done well on your first lesson," Rhys gathered her into his arms, stroking his hands over her soft skin. "Shall we say, same time tomorrow night?"

It took a few moments for her brain to register his question, "Oh no, I can not meet you tomorrow night. I have a job to do. I must...acquire something from a bard." Shiloh replied, gathering her wits about her.

He nodded his head and sat her feet onto the ground. She staggered for a moment on wobbly legs. "Jelly legs," he teased as he picked up his discarded clothing. "Then you'll have to let me know when you want your next lesson."

"I will. I promise." Shiloh knelt down onto the floor, grabbing up the pieces to her outfit and made haste to put them back on. She noticed how Rhys watched her and she flashed a brilliant smile at him.

"Honey, can you tell me why you need the 50 gold?"

Her smile disappeared quickly. "That's a long story, Rhys. I'd rather not get into it."

He nodded his head. "Keep in touch, then, honey." He finished lacing his pants up and pulled his tunic over his head. He winked at her and walked towards the dockhouse double doors. With a wave, he was gone.

Shiloh slumped down against a crate, and pulled on her shoes. She couldn't bring herself to tell him about her past and the lessons yet. Despite the fact she'd allowed him access to her body, she couldn't trust him yet. Drawing in a deep breath, she pushed herself to her feet and headed to the door, making sure she didn't attract any attention from the Dhorn Patrol as she exited the dockhouse.

Once outside, she kept to the shadows as much as possible before stepping out into the torch light. The rain had slowed to a misty drizzle. She breathed in the fresh smell of it as she headed to the bridge. She crossed it and then headed down River Road, intending on crossing into North Betancuria at the entrance nearest to the Bear Pit. She knew she could have taken the ferry across, but decided to save her money. When she came to a dark alley, she slowed her place and attempted to fade into the shadows. She noticed a gang of five men standing in the alley and saw that four of them were armed with crossbows. She gulped and hugged the wall, hoping to sneak past them.

As she crept through, she noticed that the fifth one held a bladed weapon in each hand. He had an air of superiority about the way he carried himself. A cold chill danced down her spine and she knew she needed to keep an eye out for him. Her gut told her that him catching her could be bad. Scenes of Vico and the castle attack played through her head. She didn't want that to happen again, not after she'd just felt so much pleasure in Rhys's arms.

Her thoughts distracted her from her task. Before she knew it, two hands gripped her. One covered her mouth as the other brought a blade up to her throat.

"Don't do anything stupid, little slut," the harsh voice growled.

She stiffened up as the blade pierced her neck. She felt the trickle of blood and tried to stifle a sob. It came out muffled behind his hand.

"Don't scream out!" He removed his hand. "Give me all your gold, bitch, and I'll let you live."

"I don't have much!" Tears flowed down her cheeks. "Please don't kill me!"

"Give me your money and you'll live, bitch! Call it a protection fee!" He hissed in her ear.

Shiloh dug into the small money pouch at her waist and pulled out the remaining gold coins that she had left. "Here, this is all I have. Just don't hurt me!"

He grabbed the coins from her hand, counting them one by one. "Not much, eh? Fifteen gold pieces is nothing to sneeze at. Consider yourself protected now, but remember, little slut. You had best have more coins if you wish to walk through Rick Cars's alley," He shoved her away from him and watched as she scrambled out of the alley.

Shiloh ran as fast as her legs could carry her. She didn't stop until she reached the Bear Pit kitchens. She made haste to her room, throwing off her clothing. Then she ran herself a bath and sank into the heated water. She scrubbed her body furiously, even going as far as washing her hair twice. She gently washed between her thighs, feeling how sore and tender her nether region was. She winced and removed the soft cloth. Rhys had really given it to her good. That soothed her conscious decision to try to earn some money at the docks. And now she would have to earn more, now that the remains of the money that Joanna had given her was gone. It was a good thing she'd done the shopping she needed to do for the lingerie. She didn't relish the thought of having to steal it.

As the water started to chill around her, she pulled herself up out of the tub and reached for a towel. A yawn escaped her lips as she dried herself off. She had had a big day and was quite tired. Her bed looked incredibly inviting and she crawled into it, drifting off to a dreamless sleep almost immediately.

O.O

Shiloh woke as the clock in Chella's room chimed seven distinct times, signaling that it must be seven o'clock already. She yawned and stretched in the warm confines of her bed. She listened to the hustle and bustle of the kitchen, knowing that Chella had had everyone busy for the last hour while she slept. She knew that Wally would be kneading the bread dough and Denny would be starting on the daily specials. Trissa and the twins would be washing dishes or chopping vegetables. A sigh of pleasure escaped her lips. They were busy working while she was lazing away the morning in bed. Still, she knew she couldn't stay here all day. She had to visit Master Gaston and hopefully convince him to make for her the beggar's costume. There was no way she was going to concede to that damn beggar's demands of 50 gold and a set of sturdy clothes from Gaston's. The bastard could freeze to death for all she cared.

12