Stiff Sentencing For A Young Man

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Sentenced to a night with an imprisoned giantess.
4.6k words
4.56
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Part 1 of the 2 part series

Updated 10/15/2022
Created 07/29/2011
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SugarandSalt
SugarandSalt
4,440 Followers

Ellis stood warily before the judge. His crime was small but this was a small town. Crime was an insignificant concern in Sparklewater. Ellis knew the reason for that was because Sparklewater had the reputation of swift and particularly harsh punishment. So swift in fact that Ellis had been tried and convicted in a matter of days. All that was left was sentencing. That matter was up to the judge. Ellis' case was heard before a judge known to be intolerant and heavy-handed with his sentencing.

That had Ellis scared. He was a young man of 19 years and his only crime was petty theft. He understood that it was the wrong thing to do but Ellis appealed to the judge for leniency.

In a crude underground facility only miles away...

Her full lips wrapped around the hardened mass. It swelled bigger and freely leaked precum. She swallowed the musky liquid and sucked hard on the thick pipe. Her lips and tongue worked until the large shaft and equally large balls exploded with copious amounts of potent ejaculate. She let the purple head slip from her lips, it shrunk back down to her thighs. The giantess threw her head back against the stone wall with frustration. This was empty satisfaction for the sex-crazed, mountainous shemale.

The giantess' name was Tess. She was seven feet tall with impeccable posture and ample curves all the way around. Her long red hair and rosy cheeks hadn't lost their luster after all these years in the crude imprisonment.

Tess was a giant shemale who lived with her people on a peaceful island somewhere in the Atlantic ocean. The shemales had one great love. They loved to fuck. They loved to make men and make them their property. This worked well for generations on the island. They got their fuck dolls one of three ways. Either through a shipwreck or a boat that saw their fires and went to explore. The last way took some initiative. Nearby passing ships were targeted by the shemales' boats. They forced entry and took all the men they fancied back to the island. Then they really got to know them.

Tess smiled to herself about the way things used to be. That's before their population of men dwindled. Fresh butts became harder and harder to come by. This split the peaceful community. Eventually, shemales preyed on one another. It was akin to cannibalization. They had no other choice. It was friend against friend in a fight for dominance which left the other submissive. Their aching cocks wouldn't let them stop. They needed the carnal satisfaction that only another could provide.

The shemales finally devised a plan which would make everyone happy. They set sail for another land where the men were plentiful. That brought them to America. The giant shemales eagerly surveyed the land and found many men of all different colors and sizes. Their cocks grew and leaked precum at the sight of such a beautiful land

Tess pulled a man off the street and dragged the screaming snot into an alley where they could be alone. That great feeling didn't last long as the giant shemales were ill-equipped to defend themselves against the police. They were captured or killed in the process of capture. Tess had gathered three men for herself by the time she was captured. She found herself underground in her present situation very soon after that. They starved her. Starved her of the only thing that mattered to a giantess like her. Booty.

Back at the courthouse where Ellis waits to hear his fate...

The judge peered out over his half rim glasses at Ellis. The judge had a sour look on his face which seemed to soften as he looked at Ellis, or so Ellis thought. This gave him some confidence that maybe the judge would indeed be lenient.

The judge explained the charges against Ellis and then spoke, "I sentence you, Ellis Johnson, to one night in the Sparklewater facility," he added, "for extreme punishment."

The words reverberated through Ellis' head. One night? Ellis thanked the judge and practically skipped back to his holding cell. Just one more night. He could do that standing on his head. Ellis elected to skip dinner as he decided he'd wait until he could eat at home. Ellis sat alone in cell as the sun began to set.

Two guards unlocked his door and informed him of his transport to the the Sparklewater facility, for extreme punishment. The transport took less than a half an hour before Ellis found himself outside what looked like the entrance to a basement. He looked around for any identifying marks. One of the guards kicked some dirt off a sign which reach "Sparklewater Facility, For EXTREME Punishment," Ellis instinctively gulped. The other guard unlocked his handcuffs.

They hefted a backpack out of the car and threw it into his arms. Ellis almost fell backwards from the heavy bag. "Take that in case it's hungry."

"I think food will be the last things on its mind," the other guard remarked and they both laughed. Ellis tried to ask a question but the heavy doors were unlocked and he, along with the backpack, were unceremoniously pushed inside. Ellis fell from there about ten feet and landed on the backpack. He looked back up just as the guards were shutting the doors. "Say hi to the ol' gal for us," the other added, "We'll be back for you in twelve hours." They closed the doors and the light from outside was extinguished.

Ellis adjusted his eyes to the low light that was available inside here, whatever here was. He blinked repeatedly before pushing himself up. The ground was just dirt and sand. He wiped it off his hands and heard a sound from deeper within the cave-like place.

Tess had heard commotion from ground level. She thought it was nothing until the doors opened. She might have tried escape again but the doors were just above her amazingly tall reach. Then she heard a drop. Tess prayed it wasn't food as she quietly hurried over. Her heart began to pound as she saw the man they had thrown down. He was still adjusting his eyes to the light. She got a good look at him from the darkness. He was more a boy than a man. Tess didn't mind that one bit. Her giant penis began to expand within her loincloth.

"Who's there?" Ellis asked with more than just a hint of fear in his voice.

There was no answer.

Tess continued to size up the new arrival. Most of his body was hidden by a prison uniform but that would be gone soon, she told herself.

Ellis saw a spark and squinted his eyes to see a fire being lit. Shadows still cast over the lighter of that fire though and Ellis' legs felt too much like jelly for him to walk.

"Who are you? Can you tell me more about this place?" He asked.

Tess remained quiet. She finally lit the little fire which filled the cave-like underground facility with a new light. She stepped out of the shadows and stood before the boy.

His eyes traveled up the impossibly large, sculpted legs of a woman and immediately bulged out at the sight of her tented loincloth. The flimsy piece of cloth did little to conceal her obscenely large bulge. Ellis opened his mouth but no words came out. His eyes followed her stomach up to the swell of her huge breasts, encased tightly in another piece of cloth. His eyes fixed on them for a moment but he was still speechless. Finally, he nearly had to look all the way up to the ceiling to see her face. Her feminine, stern face and long reddish hair, which draped over her ears.

Ellis thought that she didn't look old. Her body was nubile and her face was wrinkle-free but she didn't look young either. Ellis really didn't know what to make of the giantess looming over him. Her face was stern but her eyes seemed very pleased. Tess took a step forward and noticed the backpack.

Food. It's laced with something that makes me sleep so they can fish him out in the morning, Tess thought.

Tess bent her knees and leaned down, she still towered over the much smaller Ellis. Her piercing eyes cut through him, "You've been a bad boy? Haven't you?" Her nose crinkled.

"Wha... what?" Ellis' mouth was dry and it was a struggle to sputter out the word.

"That's who they throw down here. Bad boys. I don't know why. They throw down tough guys and just plain assholes." Tess looked him over more carefully from her closer vantage point.

"I'm not as selective as I once was. It doesn't look like that would be a problem with you. I like what I see." She smiled her first smile at him.

It did little to put Ellis at ease. Her gaze made him uncomfortable. "I stole... stole something. The judge sentenced me to a night here. I mean, this is the right place?" He wondered aloud.

"Oh yes. It's the right place. So you stole something? I knew you were a bad boy. These tough guys find themselves here and they aren't very nice to me. They scream and curse. It only gets worse when they realize what I want." Tess told Ellis calmly.

"What is that? What you want." He asked.

Tess lewdly grabbed her swollen, giant-sized organ and gave it a squeeze as she spoke, "Just you. More than want. It's what I need."

Ellis inched backward until he found himself against the stone wall directly below the two doors he had fallen through. His face went red and he shook his head but couldn't speak.

Tess made up the room by scooting closer to him, "What's your name?"

Ellis peered around the room but didn't see any way to escape. He could try to run, but where? She was massive, he couldn't defend himself. It looked like she could wrestle a bear. He couldn't go through with what she wanted though. That was preposterous. He was straight, after all. She had to be mad.

Tess smiled more warmly this time, "I'm Tess. Now go on and tell me your name."

He thought for a second and answered, "It's Ellis."

Tess smiled again and reached out to him. Ellis pulled back until his back was flush with the cold stone.

Tess seemed exasperated, "I'm trying to work with you here. It's not something I have to do. There are things that I need. I've explained that to you. I don't want to hurt you to get them. Okay, Ellis?"

He didn't answer, looking away.

She spoke again, "All those bad boys. Those those tough guys. The big mouths I was talking about before. They have something in common. Each and every one of them. No matter if they refused me, or fought me, or screamed for help, I got what I needed from them in the end. All of them. I'll get what I need from you too. Which way is it going to be? Are you going to fight me?" She ran her big paw down his arm.

Ellis shook his head no and was met with another smile. "Maybe you aren't such a bad boy after all, or just a smart one. Now I want you out of these clothes." Her last sentence wasn't said as sweetly and felt more like an order.

Ellis reluctantly complied and stripped the prison uniform off his body. Tess licked her lips slowly, "That's more like it." Her hungry eyes wandered over his body. "Oh my, what a sweet little body. You don't grow much hair do you?" The giantess chuckled.

Ellis felt very exposed, being naked in front of this giant woman he had only met ten minutes ago. Was she even a woman? She had the body of a woman, a gargantuan body, and then she had that equally massive bulge. Ellis didn't know what to make of it.

"I want you to turn around and show me that ass of yours." Tess told him.

Ellis barely heard her as he began to wonder who this she-man really was and where she came from.

Tess suddenly grabbed his narrow shoulders and shook him violently with a force that he thought might break his neck. She let him go as quickly as she had done it. He had never been manhandled like that and dropped on his hands, his head dizzy.

"You follow my orders. Do you understand? Make me do something like that again and it will be worse. You HAVE to listen to me or this night is going to feel like an eternity." I wish, she thought to herself.

His dizzied head weighed the options and he realized that he had to listen for his own sake. Whatever she wanted, he had to comply. It was the only way he'd survive the night. He knew it was true. He couldn't fight this mountain of a woman or the humongous cock between her thick legs.

Ellis shook his head yes. She made a pointing gesture to the wall. Ellis turned around and bent over for the giant shemale.

Tess' eyes locked in on Ellis' supple butt cheeks. They were spread just about an inch from Ellis' being bent over. She could just get a shadowy glimpse between the two globes. "Use your hands and pull your butt cheeks apart. Do it now." She told him.

Ellis' embarrassment and shame were evident on his face as well as his body. His entire body seemed to redden at the intrusion but he did as she instructed him and gently spread himself open for her.

Precum leaked through the loincloth. Her stiff erection begged for attention. What Tess saw was worth more to her than all the gold in the world. Food, money, even her old shemale friends meant nothing to her. This was all she needed. Ellis' treasure was exposed to her. Everyone had this treasure, but they were rarely if ever as beautiful as this boy's, Tess thought to herself.

She eyed between his boyish butt cheeks. It was just too pretty. His wonderful little crack. The texture and deep pink coloring of his anus. Tess let out an excited whoop which startled Ellis.

"Turn around before I get ahead of myself." She ordered.

Ellis obediently did as he was commanded and turned to face her, his eyes lingered on the bulge under her loincloth which seemed to have grown, if that was possible.

Tess undid the tie on her loincloth and the flimsy cloth fell down her thighs. A huge, hard cock sprung up and pointed right toward Ellis. It was easily a foot long and so thick that he didn't think he could even get a hand around it if he tried. Spiderweb veins lead up her shaft to the purple, wet tip. Two giant balls nestled up to her thick, sculpted thighs. Ellis swallowed hard.

"First things first. Show me how honored you are to be here with me."

He pulled his eyes from her cock and looked up at the giantess kneeling next to him, "Please. I'm not trying to disobey. What do you want me to do?"

"Kiss it." She said promptly. Tess lifted herself up to her feet. The giant cock was only inches from his mouth when he sat up on his knees.

Ellis inched forward and gave the incredibly hot, wet tip a little kiss, pulling back quickly. A string of precum followed his lips back. Tess chuckled, thrusting her hips out toward him and pressing her big cock head against his soft lips again. She maneuvered her cock and painted his lips with the precum like she was applying lipstick. Ellis closed his eyes but didn't pull away.

"Open up." She told him.

Ellis looked up the giant form of the shemale and looked into her eyes with a pleading glance. She looked back at him with fire in her eyes. He knew better than to disobey and slowly opened his lips.

She pushed the tip of her cock, stretching Ellis' lips open wider, and managed to fit half of the tip inside. Ellis swallowed the precum. Her cock tasted like it hadn't been washed in a while but it wasn't pungent to his taste buds. The spongy consistency was unique. It was hard as a rock and soft and warm in his mouth at the same time. He struggled as she pushed the rest of her tip inside him, with a moan.

The tip filled up nearly all of his oral cavity. Her hips rocked back and forth rhythmically. The slit continued to produce more precum which he quickly swallowed.

"Now suck," she added, "Use your tongue."

Ellis' tongue crept over the hard mass and he started a swirling motion around the big head.

"Oh... boy. I haven't had my cock sucked by someone other than myself in... oooh suck it. That's a good little cocksucker. I know exactly what to do with you..." She cooed.

Tess' rhythmic rocking became faster and harder as Ellis struggled to stop gagging on her huge meat. She grabbed his head in a frenzy, sending her cock deeper inside his mouth.

"I'm going to make you a deepthroater! Yeah... you'll like that..." She trailed off.

Ellis' hands pushed against her thighs but she was too strong. Tess didn't even seem to notice his reluctance and wouldn't have cared anyway. She pushed the meat deeper into his sucking mouth. His mouth caved in as he tried to expel the intruder but that just made it more pleasurable for Tess, whose eyes were closed tightly at the time.

"Now you know. You're all mine. Tess' property. You won't be stealing anything anytime soon. Just suck this cock. Yeah." She told him.

He choked on the massive shaft as it forced its way into his throat. Tess roared in pleasure, which was the only warning that she was about to cum. She thrust her hips against his face while using her hands to pull him closer as the explosion hit. More than half of her cock was in his mouth and at least a couple inches down his throat.

Volley after volley of the hottest, stickiest cum shot from her cock down his throat. Ellis felt like he might pass out but couldn't get free of the massive cock. He was forced to swallow every drop. Tears ran down his cheeks from the sheer pressure of her cock as she spent the rest of her load, crying out in intense pleasure herself.

Tess pulled her massive shaft from his mouth. Ellis fell to the floor, gasping for breath. She grabbed her discarded loincloth and used it wipe up the cum and spit mess that was left on her half-hard cock. "Thanks for that, sweetheart." She laughed.

Tess was the happiest she'd been in as long as she could remember. She skipped around the underground room as Ellis struggled to catch his breath. Cum was leaking down his face and onto the dirt floor. He felt like cum was even leaking from his ears. What he hadn't swallowed was everywhere. He was a sticky mess. This wasn't the kind of cum he produced either. His few dribbles were nothing in comparison to Tess, who could paint his entire body white with the stuff.

Tess threw a rag at him and told him to clean up. He did as she ordered and cleaned his face off. They didn't speak. She'd glance over at him with a big smile and blow a kiss if she saw him looking. A couple minutes passed and Ellis finally recovered from giving his blowjob.

"Alright... you've gotten what you want. Let's just sit here and wait for the sun to rise so I can get out of here." He told her.

She looked puzzled. "You've got a lot of nerve, haven't you?" Tess snarled at him, "I figured I had worked that out of you. I guess there's still more to be done. I'm up for it. Come over here. Now." She commanded him.

Ellis crawled closer to her on the other side of the room. Her body was lit up by the fire, her massive cock lying against her thigh, still impressive. Tess patted the ground next to her and he moved there.

Tess pulled the cloth of her top off without a word. Her full breasts spilled out. They floundered against each other until finally settling on the ground. The sight gave Ellis an erection. Tess noticed and smiled, "Does my bad boy like what he sees?"

Ellis slowly shook his head yes.

"Kiss me." Tess told him.

He tentatively moved closer and planted his lips on her cheek. Tess laughed loudly, the way her voice could fill the room startled Ellis.

"That of all places is where you choose to kiss? You just gave my cock a sucking and now you're acting wholesome. Don't be so coy, my darling Ellis."

Ellis kissed the giantess' full lips. Tess quickly wrapped her arms around him and pushed her oversized tongue into his mouth. Their tongues wrestled for a minute (hers won) before she let him go. Ellis kissed her shoulder and then the side of her big breasts without prompting. He was shocked to look down and see Tess' cock rock hard again.

"Now comes the most fun for me, Ellis. This is going to hurt you, my sweet. I can't say it won't. Just listen to me and we'll limit the pain together. You have to listen to me. Do as I say or I won't be responsible for my actions." She warned him.

SugarandSalt
SugarandSalt
4,440 Followers
12