Stiff Sentencing For A Young Man Ch. 02

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Characters appear or are referred to in this chapter which were only present in the prequel to “Stiff Sentencing For A Young Man,” “Land of the Giant Shemales,” but you don’t have to read the prequel to understand this chapter because this is Ellis’ first introduction to these characters as well. I would recommend it, though, because it’s got a ton of big-dicked giantess fucking and that’s neat.


Ellis struggled to stay on his feet. His entire body ached. Tess really meant it when she told him that they were going to savor the next ten hours. She’d savored him over and over again. Ellis had been used by this giant shemale in more ways than he’d thought one person could use another.

This abuse was far from the worst thing bothering him at this moment. His dirtied fingers dug into the dirt wall of Tess’ cell. He put every ounce of strength into keeping himself steady under the weight of his companion. Tess had balanced herself on top of him the moment they heard an approaching car.

He promised to explain to her later what a car was, but for now, she was pretty much breaking his back. Ellis didn’t know how long he could hold her weight. You try keeping your back straight with a seven-foot tall giantess balancing on it! Now try it after she spent the better part of a whole night with her giant cock planted so far up your ass that when she cums, you can almost taste it.

“Shhh!” She hissed down at him.

Ellis hadn’t realized he’d been making noise, but since he was already seeing stars, he didn’t really know what he might be saying or doing. Then there was a creak above them. Suddenly, the morning light cascaded down on both of them.


Tess leapt off of Ellis’ back; he fell to the dirt. Ellis heard scrambling up top; the scrambling turned into screaming. Ellis would have looked up, but he was too weak to lift his head.

“Grab on to this, my sweet!” Tess’ voice called down to him.

He mustered up the strength to look up. Tess was dangling a pair of pants down to him. After having his face in the dirt, she looked like an angel to him with the rays of sunlight behind her, and her hair blowing in the breeze.

He felt a small surge of strength fill him. Ellis grabbed the pants and held onto it for dear life, all the while watching his new lover. She pulled him up from the dark cell with one flexing arm.

“Put these on.” Tess dropped the pants in his lap once she’d pulled him up. “I gather from the men we had stashed on my home island that the man’s naked body is taboo here.”

Ellis had forgotten that he was still naked. Tess had taught him in one short night that clothes weren’t really for him. He slipped them on, surprised by their sudden foreignness and then caught sight of the two guards who’d thrown him down to Tess last night. They were out cold; one of them now missing their pants.

Tess saw him staring at the men, “We only need one.” She spoke. Tess lifted one by the collar of his shirt and looked at him. “This one’s prettier. We’ll leave that one.” She grabbed the other guard by the leg and dragged him over to the opening of her cell. Tess gave him a kick which caused him to fall in. She shut the door behind him.

“What, what do you want him for?” Ellis was almost afraid to ask but he thought he was entitled to know.

Tess walked over to Ellis and lifted him up roughly by the arm, “Think you can walk, sweet cheeks?”

“I can walk. What about what I asked?”

“You are a curious one, aren’t you, my darling Ellis. We’re taking him with us because I didn’t come here alone.” Tess threw the unconscious man in his underwear over her shoulder, “I want to find my friends.”

“There are more of you? More like you?” Ellis hadn’t considered that before. He formed images of other giantesses in his head.

Tess started walking toward the car, the flimsy loincloth had completely ridden up the crack of her ass. Every inch of her big beautiful ass was exposed to Ellis’ eyes. He tried not to blink.

“There should be. Only if your people haven’t gotten to them yet.” Tess gave the vehicle the two guards had driven up in a puzzled look. “Can you ride this?”

“Yeah, don’t worry. Get in.” He said. Tess hefted her long, muscled leg onto the hood of the car and climbed on top of it, then gave him an impatient look. He held back laughter.

Once they’d worked out that the idea was to get into the car, not onto it, Ellis got into the driver’s seat and then looked for the keys. Tess looked at him skeptically the entire time. Then he remembered about the pants and dug through them, finding the key. He blushed.

The giant shemale asked him if he knew of a safe, secluded place to question the guard, so he started driving toward his apartment. Ellis felt one of Tess’ great big hands on his thigh during the drive. He glanced over and saw pure desire in her eyes.

She didn’t seem at all fazed, nor satiated, by their long night of carnal passion; that realization was of the painfully Ümraniye Esmer Escort exciting variety to Ellis. Painful because his ass hadn’t recovered from her reaming. Exciting because he’d learned to love it over the course of one long, beautiful night.

They got stuck at a light and Ellis’ eyes inevitably shifted toward her. He had to do a double take when he caught a glimpse of her this time. Tess had the man flung over her shoulder, she’d pulled down the man’s boxer shorts and currently had one of her substantial fingers in between the globes of his hairless ass.

In her lap, her dick stood to attention. Tess’ loincloth puffed out around her shaft and looked ready to snap. Ellis pictured the wedgies these big erections of hers gave; cloth wasn’t capable of stretching to keep up with the way her cock grew.

“Jealous?” Tess spread the man’s legs apart and then repositioned him so that his ass was pointing toward Ellis. His asshole was inflamed from the forceful action of the giantess’ finger.

“No. Jealous of what?” The red light turned green. Ellis looked out his windows and then turned to Tess as he gave the car some gas, “If you don’t want us to get stopped, you should probably stop playing with that guy’s butt while we’re driving. These windows aren’t tinted – I think some people are looking.”

“Men were only made for one thing and that’s what I’m doing. Can’t you convince this thing to move its stubby legs faster? And why do we keep stopping?”

“You can’t convince a car of anything. Those stubby legs are wheels and we’re stopping because there’s such a thing as traffic laws here!”

Tess’ hand squeezed Ellis’ thigh tightly. He yelped, remembering his place again and promptly apologizing to the giantess with the monster cock.

“I’m sorry. We’re almost there anyway.”

The big shemale could see the hurt feelings on his face. Her grip on his thigh loosened, her hand slid over to his cock; Tess tenderly squeezed his modestly-sized organ between her giantess fingers.

The three of them made it back to his apartment. Ellis had to convince Tess to pull the guard’s underwear up so they could get him outside and into Ellis’ apartment without raising too much suspicion. A giantess carrying a underwear-clad unconscious man being led by a shirtless young man to his apartment. Nothing suspicious, right?

Ellis rifled through his pants and then remember that they weren’t his pants, and he didn’t have his keys, “Oh shit. I think they still have my keys.”


Tess threw her over-sized shoulder into the door and it nearly shot off the hinges.

“Where’s your bedroom?” She huffed.

Ellis pointed toward the right room. Tess shuffled over to there and pushed the door open. He heard his box-spring squeak as Tess threw her captive down the bed.

“What are you planning to do with him?” Ellis called out with a bated voice, following Tess into his bedroom.

“Tie him to bed.” She ordered.

Her stern face caused Ellis to look elsewhere. “Umm.. okay, I think I can do that.”

“Have you anything to eat around here?” Tess said in a gentler voice with her face softening.

“Errr – sure. Check the kitchen. Oh yeah, you can’t miss it. There’s a big white box in there. Though, not as big as you, but you get the picture.” Ellis bit his lip.

He opened his closet and pulled out a belt once she’d left. Ellis walked over to the man, whose body laid so still on the bed. The unconscious man must have no idea what he’s in for. Ellis had an idea, though, as he felt the dull ache from his anus.

Ellis grabbed the man’s arms and stuck them through the sturdy metal poles of his headboard. He coiled his belt around the man’s wrists next, then his headboard. The man started to stir below him. The movement startled Ellis.

“Wha – where am I?” The guard asked him slowly, as if memory of his final conscious moments were coming back to him.

“Shut up.” Ellis said scornfully, remembering himself how the two guards had laughed at him when they dropped him down to Tess. Then he thought of how they’d referred to her as “it” without a single ounce of the respect one human should treat another with. Ellis pondered for a moment whether Tess was human, but decided it didn’t matter either way.

Both of the men jumped when a crashing noise and a loud grunt came from the other room. They could hear the heavy footsteps of the giantess approaching Ellis’ bedroom.

“Please. . . help me out of this.”

Ellis shot him a sharp glare and then smiled at the imposing figure who showed up at the door. Tess lumbered into the bedroom, her eyes on the tied up guard and a half-hard cock under her loincloth.

“Where are my friends?” Tess dropped her knees down the bed and scooted up until she was kneeling over the man’s legs.

“Can I stay and watch?” Ellis asked hopefully.

“Yes, I may need you.” Tess pounded her hands down on the guard’s stomach while she waited for her answer.

“I don’t Ümraniye Eve Gelen Escort know anything about your friends!” He cried out, his legs flailing around wildly.

Tess leaned off of him, she sat back on his shins which stopped his legs from moving. She lifted her tattered half-shirt up and wiped her mouth. Tess’ big jiggling breasts popped out of the shirt when she did it. Ellis gave a gasp, his pants tenting. The guard groaned and tried to look away, but somehow his eyes ended up back on her chest.

She dropped her shirt back down. “Men.” Tess smirked, “Men and their titties. Love ’em almost as much as giantesses and tight assholes.”

“I’ve told you what I know – nothing. I promise I won’t tell anyone that you’re free.” The guard pleaded.

“If you don’t know anything else, that means you only have one use left.” Her smirk turned into a full-blown smile.

“Just get off me. Please, let me up!” The man tried to kick his legs again, but they were stuck underneath Tess’ big butt, in other words, they weren’t going anywhere.

“Ellis, baby.” Tess turned toward him with a calm in her voice, “Show him what his asshole is going to look like once I’m done with it.”

Ellis pulled his pants down and bent over the bed, spreading his legs and giving both of them a view of his asshole. Tess’ repeated intrusions were easily identifiable. The swollen back passage looked just like a rosebud.

Tess proudly surveyed her work and then looked back at the tied up guard. “You’re next no matter what. You don’t control your fate, now. The only thing you have the power to change is how bad you get it. I can be quite mean.” She said with a scowl on her face.

“Wait…!” The man cried out from under Tess. “There was some talk! Just something I heard -”

“What did you hear!” Tess snapped.

“I heard there was another one like you in Sparklewater.” Tess’ hands pressed into the guard’s chest and he wheezed. “We don’t have her. I heard she was at this lab. They said she was a real beast – stuck her in a cage or something when they caught her boning staff. That’s all I know! I swear.”

Tess gave the guard a lecherous smile. She reached for his boxers shorts and dragged them down the frightened man’s legs.

“Keep quiet or I’ll have my sweet muzzle you!” Tess turned toward Ellis, her tented loincloth pointed straight toward him, “Mind getting us set up?”

Ellis swallowed with his drying mouth and nodded his head. He undid the string on her loincloth and revealed Tess’ masculinity in all its glory; this caused the guard to renew his fight, but it was short-lived. Tess shot him a, “you better knock it off unless you want to really make me angry” look.

Ellis didn’t notice it because he was so fixated by the brutish hunk of meat between Tess’ thick thighs. His hand circled around the shaft; his dry mouth now watering, Ellis wrapped his lips over the precum slick tip and began to suck. His mouth adjusted to accept more of the mighty shaft.

He’d covered every inch of it in natural lubrication before Tess reluctantly asked him off. She’d pulled her top off while Ellis was cock-loving between her legs. Tess brought the man’s legs up until she was pinning his ankles to the bottom of her shoulders.

“Spread his butt cheeks so I have a clear path to that asshole of his I was fingering on the way over here, please, my darling.”

Ellis complied, leaning between them and looping one arm under the man’s legs so he could effectively spread the man’s ass without obstructing Tess, nor her cock, in any undesired way. Ellis gave the man one last glance and saw his eyes were closed; his face a deep crimson color.

Tess’ over-sized cock head made first contact with the guard’s asshole and Ellis could see the guard’s cock instantly harden. It shot straight up in the air and the guard groaned. He wiggled his ass, but Ellis couldn’t tell if that was his last attempt to get away or just an involuntary reaction to Tess’ cock, but regardless, he gave no more fight.

“Oooooooh,” Tess pressed her hardness into the man. “He’s tight, Ellis. Tight and clutching.”

The guard gritted his teeth but didn’t say anything as the inches of Tess’ cock steadily disappeared inside him. Ellis let go of the man’s ass and sat back to watch the action. He watched, fascinated and not even sure where to look.

Should he focus on the veiny piece of giantess meat slipping inside the guard; her titties as they bounce against her chest in time with the thrusting of her hips; her bounding ass; or the immense pleasure playing out on her face?

Tess pushed down on the bed in a push-up position but which her knees down on the bed too. The man’s ass had to pop off the bed a few inches so that his legs could stretch out between them. Tess was grinding her hips against him, sending her giant cock as deep as it would go into his insides.

“He hasn’t been too bad, Ellis. I decided I’m not going to hurt him. A little harmless fun like this, Ümraniye Evi Olan Escort that’ll be just fine.” Tess said in between thrusts.

Ellis watched Tess’ ass as it swung back and forth in the air and bounced all over in the air above the bed. He found himself drawn to the giant shemale’s voluminous cheeks and deep crack; the desire within him to worship that great big masterpiece of giantess flesh was too strong.

He moved closer until his face was inches from the two big cheeks, which swung together in a blur as she powerfully ravaged the guard underneath her. Ellis gingerly kissed the cheek closest to him. The room was filled with grunting and the squeaking of Ellis’ bed.

Tess laughed when she felt Ellis’ lips and then started ramming her cock inside the guard faster. He writhed underneath her – releasing a moan in the process. Ellis, with a little more courage, planted little kisses across her butt cheeks and the expanse between them of pink, warm flesh.

“Give my dot some kisses, my dear. That’d feel quite nice.” Tess pushed her knees out further on the bed, giving Ellis more access to the beautiful insides of her cheeks, and the wrinkly little (though it’s difficult to call anything about a giantess little!) hole.

Ellis’ face slipped between the globes, his lips pressed against the tight wrinkle for a kiss. Ellis’ arms wrapped around Tess’ waist and he followed each bounce of her ass with his face. His kissing soon turned into licking. Before long Ellis was stabbing his tongue at the hole.

He came up for air, starting over again from the top of Tess’ crack. Ellis’ lips trailed lower and he caught the loose skin of Tess’ balls in his mouth. He sucked deep and pulled half of an ostrich-sized giantess nut into his mouth. His tongue rolled over the sticky, sweaty skin.

“I’m gonna cum any minute! Ellis baby, fondle my titties!”

Ellis straightened up, his hands disappeared into her massive, pendulous breasts. His hard cock brushed up against her crack and in the passion of it all, as Tess cried out in the midst of orgasm, Ellis started thrusting too. His dick slid between the meat of her sweaty ass cheeks and he humped her backside.

She poured her monstrous load inside the guard, enjoying every moment. Ellis could feel he was about to cum just as Tess finished inside the guard. His seed spilled out onto her ass. When they were finished, Ellis unlocked his arms from around her and nearly fell of the bed. Tess caught him and he saw her stomach was absolutely covered in cum.

“His. . . he did that?”

Tess looked down at her stomach, back at the guard who looked to be fucked into oblivion, then scooped some of the semen up with her fingers and licked the load off her fingers. “Mmmhmm. He’s going to remember that forever. And trust me, he’s going to miss it. Just leave him and let’s go.”

The two of them stood up and tried to get some clothes on. Tess tore his closet apart but couldn’t find anything that fit. She settled on the biggest shirt Ellis owned, which fit so snugly around her breasts that her nipples poked out of it a full inch. Tess wanted to go without a bottom, and Ellis would have loved to watch her dick swing between her legs all day, but they couldn’t travel like that. He convinced her to wear a pair of stretchy pants, which could barely contain her ass and had a giant bulge in the front.

“Come on. We’ve got to find Donna. She might know where the others are.” Tess hooked her arm around Ellis’ as they walked.

“He didn’t mention a name. Who’s Donna?”

“He said she was a beast who forced herself on staff; I’d bet anything it’s Donna.” Tess looked at the silly grin on Ellis’ face and cautioned him, “You better behave, my darling. You don’t want Donna noticing you. She’ll never give up once she does until she has you, and she’s not gentle like I am.” Tess dragged him out the door.

“We’ve got to find this Sparklewater place that cock-servicer spoke of; perhaps a spring of some sort? Have you any ideas?” She asked.

“. . . This is Sparklewater. It’s the name of the town.” Ellis replied, unlocking the car and dropping into the driver’s seat. “It’s a small town, so I think I know where she is.”

Tess looked out the window at sights she couldn’t possibly understand. They hadn’t been on the road long before she piped up, “Would you believe it? I’m getting horny again. Seeing all these men out here in the open – I have this urge to stash a few away for later.”

Ellis’ eyes drifted to her crotch and sure enough, she was hard again. He started explaining to her about where he thought Donna must be. “Do you have a plan for once we get there?” He asked.

“We’ll be fine just as long as they don’t have those weapons that your people used when they captured us.”

They got to the facility Ellis thought the guard had mentioned. Both of them walked through the front door and as they approached, Ellis obsessed over what they would ask. He couldn’t just ask where they were hiding the horse-hung giantesses.

They didn’t need to say anything as it turned out. The man at the front desk’s expression said it all.

“Where are my friends!” Tess pounded her big paws down on the desk.

He didn’t answer, pressing a button on the intercom and screaming, “We have a visitor! Get down here quick!”

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