Round 18

[b]Round Eighteen:[/b]

Marty appeared in a dungeon. Chains hung from the ceiling all around the room. Every wall was criss-crossed and covered in metal. Beside the chains were cages, wooden posts and strange devices. The walls beyond the chains were dark stone as was the floor.

https://laristopa.smugmug.com/Story/n-crrWG8/i-DHjkgHG/A

The room was strangely damp and cold. A feeling of dread and vulnerability pervaded every square inch. Marty couldn't shake the feeling that every chain, every strange wooden and metal object in the room was placed there intentionally - and for a purpose.

Marty shifted his focus down to his outfit. He had on a simple pair of jeans, a plain green t-shirt and his signature leather heels. He released a sigh of relief. Finally he was back in normal clothes. Marty quickly checked his heels - at least somewhat normal. No more questionably girly shirts and pants for this guy Marty thought to himself.

Despite the rather grim setting, Marty found himself smiling. The comfortable male clothing was really making him happy and his brain didn't really process the setting around him as well as it used to.

Sandra appeared with a soft *pop*. Marty felt a stirring in his jeans as his little member pressed against the chastity cage. Sandra looked beautiful. Encasing her ample bosom was a tight leather jacket which she pulled around a low cut black top. Her bottoms were an almost transparent sheer body stocking. Marty found himself staring at her curvy ass. Her long blonde hair cascaded down her back, her face was smartly made up, and she wore tall red heels. She shot Marty a smoky look over her shoulder with her small but shimmering hazel eyes before turning to face him. Marty gulped, he could see a noticeable cleft between her legs where the stocking was very tight.

https://laristopa.smugmug.com/Story/n-crrWG8/i-Z4p6XJQ/A

A few awkward seconds passed. Marty was trying to ignore the stinging in his crotch while simultaneously making it worse by staring at Sandra.

Sandra pursed her lips as she observed the room. She spoke softly in a rich alto, "Well...this place is horrifying."

Marty's smile faded and he nodded, "Y-yeah."

Determined not to allow another awkward silence, Sandra kept her voice upbeat and spoke again, "I like your hair. Not exactly the manliest cut, but we'll get it styled properly and you won't know the difference."

"Uh huh." Marty replied. He was staring at Sandra, she was so pretty.

She furrowed her brow, "Are you okay, Marty?"

Marty nodded absentmindedly and responded, "You're just so...pretty..."

Sandra walked to Marty until she was directly in front of him. He looked down at her and noticed a concerned expression.

She reached one of her hands up and gently rubbed Marty's cheek, her face was genuinely concerned, "What did they do to you?"

Marty closed his eyes and enjoyed her touch before putting his own hand onto hers. He mumbled, "I'm fine."

Sandra immediately whispered back, "You can tell me."

Marty exhaled deeply before noticing he could see directly down Sandra's shirt. His little cock surged again and he winced in pain while grabbing at his crotch.

Sandra frowned, "Your monster still caged, I take it?"

Marty pulled away from her and grunted, "Yeah - and it hurts."

She took a step back, "I'm sorry Marty, I forgot. I'll try to keep things PG."

Marty continued to struggle while Sandra walked to the chained wall. She put both hands up and grabbed onto two random links. She turned her head over her shoulder and stared back while pushing her nearly naked butt out at him.

She bit her lower lip and moaned out while wiggling her ass, "You want to tie me up with these chains, daddy?"

Marty grunted and turned his back on her. Between laughs, he winced in pain as the cage dug deeply into his cock, "You're an ass! A damn fine...big bouncing ass too."

Sandra's infectious giggle added to Marty's and they were soon filling the miserable dungeon with laughter.

Sandra walked back towards Marty, still giggling, "You know, I could get used to-"

Mistress Jennifer appeared and the laughter instantly stopped.

https://laristopa.smugmug.com/Story/n-crrWG8/i-5v2GBwK/A

The already cold temperature of the dungeon dropped another few degrees. Mistress Jennifer stared daggers into Marty and Sandra. Her expression was predatory and aggressive. Standing next to her was a tall, muscular man with a dark expression. He held a black whip in his hands but adopted a subservient posture.

https://laristopa.smugmug.com/Story/n-crrWG8/i-b3Vvdxb/A

Marty froze in place while Sandra backed up and pressed against the wall. An intense fear was plastered across her face with wide eyes and quick breaths.

Mistress Jennifer growled in Marty's direction, baring her teeth. "I told you never to have clothing on in my presence, worm. Take them off - NOW!"

Marty began to quiver but immediately began doing as he was told. He tore his shirt and pants off until he was standing in just his heels. The comfort, security and positive feeling the clothing had provided him was completely stripped away. His hairless, pathetic, little cock was open for everybody to see. He knew better than to try covering it up.

https://laristopa.smugmug.com/Story/n-crrWG8/i-zKwGg9Q/A

Marty could see out of the corner of his eye - Sandra was looking right at his withered manhood. A shameful shiver washed along his body like a frozen wave.

Mistress Jennifer surged forward aggresively, her chainmail swished and jingled. She was standing directly over Marty who shrank down and stared at her feet. The male holding the whip silently shuffled behind her as she moved.

Mistres Jennifer spoke directly into Marty's downcast face, "I know you're even more of a simpleton now so I'll use small words even you can understand. What does a sissy slave say when they fuck something up?"

Marty hesitated before croaking out in a weak whisper, "I'm s-sorry mistress."

Mistress Jennifer stood upright and smiled widely. A renewed chill washed over Marty, her smile may have been even more terrifying than her 'angry' face.

She practically chirped, her voice suddenly filling with glee, "Apology accepted. Of course, there will be a punishment for your gross misconduct, but at least you're able to properly admit fault."

She shifted her attention to Sandra who was still pressed firmly against the far wall. The chains next to her sprang to life with a terrible rattling and coiled around her arms. Sandra screamed. She tried running away, pulling away, twisting away - but nothing stopped the chains as they gained control. Once both her wrists were shackled, the chains shifted around the room until she was being held with arms outstretched to opposite walls. Sandra was red in the face and continuing to struggle in futility.

"W-what are you doing?" Sandra gasped while catching her breath.

Sandra's clothing melted away and she was left completely naked. No shoes, jacket, body stocking, nothing. With her arms outstretched, Sandra had no way of covering herself and every part of her femininity was out in the open. Her large, jiggling tits flopped around while she fought against her restraints.

The man holding the whip took a step towards Sandra. The whip uncoiled silently and rubbed along the floor.

Marty pleaded, "Please don't do this. I'm so sorry Mistress, it was my mistake - I should be punished."

Mistress Jennifer cackled, "But my dear slave, you are being punished! Here, I know what will make you feel better. I'm feeling extra FORGIVING today. If you administer twenty lashes all is forgiven and you win the round."

The muscular man presented the whip to Marty who carefully took it with a shaky hand. The dark leather was smooth and cool to the touch.

Sandra yelled at Marty, her voice was shaky, "Just give her what she wants. I don't blame you for anything."

Marty stared down at the whip. He could feel his heart racing. Could he really WHIP somebody. Especially somebody he liked?

"I can't do this." Marty sputtered. "She won't be hurt because of me."

He slowly opened his hand until the whip slid out and dropped to the floor with a soft thud. The man bent over and silently collected it.

Mistress Jennifer put her hands on her hips and shook her head. "Tsk Tsk Tsk little sissy. I guess you have more learning to do. Fortunately, I had a feeling you would continue being insubordinate."

She snapped her fingers and Marty heard a loud popping sound - like a gunshot. He froze and felt something was about to happen.

Sandra screamed, "Marty - watch out!"

Quick as lightning, a chain shot from the floor just in front of Sandra and hurtled towards Marty's head. Before he could even react, a metal collar at the end of the chain secured itself tightly around his neck. He immediately began pulling at the collar, but it was locked tight and Marty couldn't find a clasp. The collar was connected to the chain by a thick metal ring. The chain stretched back a hole in the ground just in front of Sandra. Marty tried to scream but only managed a muffled choke as his throat was constricted. An ominous clanking sound rang out from the ground and any slack in the line was tightened. As the clanking continued, Marty felt himself being pulled forward. He tried fighting the mechanism but it only served to dig the collar deeper into his neck. He shot a pained glance at Mistress Jennifer who seemed to be enjoying herself based on her horrifying grin.

Marty had no choice but to follow the chain with as little resistance as possible. Being dragged along the floor by his neck didn't sound enjoyable. When he got to the hole in the ground which the chain was being fed into, Marty was forced onto his knees. The clanking sound stopped with about a foot of chain left between the collar and the floor. Marty was left with his chubby ass sticking up. He looked up at Sandra who was just a few feet away. They shared a fearful stare.

The sound of equipment being moved behind him startled Marty. He didn't know what was going on and couldn't crane his neck far enough to see. But as he looked up to see Sandra, he knew whatever it was wasn't good. He heard a loud *thud* directly behind him.

"Be strong Marty- don't let them- Mhhhmhhmh!" Sandra's mouth was suddenly filled with a red ball gag.

"Don't do this! Don't do it! Please, I'll do anything!" Marty pleaded desperately, tears streaming down his face.

Mistress Jennifer knelt next to Marty and spoke into his ear, "Oh, I know, slave. I'm giving you the opportunity to do just that!"

She rubbed her hand onto marty's cheeks, coating her fingers with his tears. He tried pulling his head away but he had no choice. He wanted to reach out and grab the vile, evil woman. To wring her neck and break every bone she had. But...attacking her now would only make the situation worse. She had all the power here.

Marty saw Mistress Jennifer reaching her hand back towards his backside, "W-what are you doing?"

One of her tear soaked fingers probed his asshole. She coated it and slowly pressed her finger inside.

"Wait! W-wait!" Marty screamed, "No! N-n-ahhhh!!" She pressed her finger in and out. It was painful and dry. More tears, this time from pain, gushed out making Marty's face hot. Mistress scooped the tears up and transferred them to Marty's ass providing some modicum of lubrication. Marty kicked his feet and flailed his arms, despite his fear of retaliation, he found himself reacting as opposed to deciding.

"Mhmmhmm!" Sandra shouted while kicking her legs, her hair and tits flailing all about.

Mistress forced Marty's legs into the proper position with a grungt and metal bands were secured around them on hooks in the stone floor that Marty had previously overlooked. His ankles were in an extremely uncomfortable position and trying to move them aggressively made it even worse. With his neck and legs now secure, he really only had his hands free and they couldn't quite reach and interfere with what she was doing.

Mistress had nearly her whole finger inside of him, pumping it in and out, using his tears as lubrication. Marty had never experienced any type of anal play on himself - it was a very strange feeling to him. When her entire finger was inside, Marty felt something bizarre. His hips jerked forward and a blast of pleasure shot up to his cock. She pushed her finger all the way in again and there was another jolt. Mistress Jennifer pulled at Marty's little cage and removed it completely. He felt instant relief and looked between his legs. His hard cock was laughably tiny.

https://laristopa.smugmug.com/Story/n-crrWG8/i-TbB7SxM/A

She removed her finger and Marty's asshole felt rather open and empty. He shuddered at the realization that he - he wanted her finger back in...Wait, no! He didn't want that! He wasn't gay! He liked putting it in girl's asses! Not having anything in his...Right?

He heard a squirting sound, like ketchup out of a bottle. Only, he was pretty sure it wasn't ketchup. She rubbed the cold lube onto Marty's hole before pushing her finger back inside and coating his inner walls. He felt his cock jumping to life as she rubbed inside of him. He couldn't help it!

Mistress Jennifer stood up and spoke with excitement in her voice, "Now we're going to have so much fun! You're all warmed up for pleasure, Slave. Meanwhile...your little friend will be receiving the pain."

Marty reached his hand towards Sandra. Tears were streaming down her cheeks. He want to stand up and rescue her. He wanted to punish Mistress Jennifer and take Sandra far away from this place. Sandra pushed her foot towards him and they met in the middle. The second they touched, Marty felt his tears renewing in his own eyes. He wanted desperately to save her...but this isn't that kind of story.

*WHACK*

Sandra screamed around her ball gag and her entire body shook. Her foot recoiled from Marty's touch and she was sobbing.

As the first lash struck, Marty heard something behind him click and spring to life. A long, thick finger pressed into his lubed up, loosened asshole. He grunted and the finger pumped in and out. Each time the finger plunged inside Marty's cock surged with a zap of pleasure. He craned his neck as far as it could go to see - it was no finger!

https://laristopa.smugmug.com/Story/n-crrWG8/i-ZL6zKhj/A

The machine pumped at a methodical pace with a mechanical whirling sound. A long, veiny white dildo sloshed into his ruined hole again and again.

*WHACK*

Sandra screamed again. Her sobbing deepened. Marty, meanwhile let out a moan. The pleasure from his violated asshole was becoming more than his stiff little dick could bear.

*WHACK*

*Sob*

*whirlwhirlwhirlwhirl*

*Moan*

*WHACK* *Sob*

*whirlwhirlwhirlwhirl* *Moan*

*WHACK* *Sob* *whirlwhirlwhirlwhirl* *Moan*

All the while Mistress Jennifer's horrible, mocking laughter, filled the room.

Sandra's head hung down while she wept. Thin, long red lash marks were all across her body.

*WHACK*

https://laristopa.smugmug.com/Story/n-crrWG8/i-7tvx9qG/A

Marty was instinctively pushing back against the machine and was lost in pleasure. His entire lower body was tensed up and he was preparing himself for a messy orgasm. The feeling of being filled...he couldn't quite explain how right it felt!

*whirlwhirlwhirlwhirl*

*WHACK*

Marty released his loudest moan yet and his cock shuttered. A paltry dribbling of semen gushed out of his sad little penis and onto the stone floor. His orgasm was so strong that he felt ready to pass out. The machine clicked off and slipped out of Marty's asshole. He felt a breeze run across the loose orifice.

He picked his head up and looked at Sandra who sagged down, being held up by her arms. Marty reached his hand up toward Sandra again. Sandra raised her red, tear covered face up. Her makeup was all over the place. She weakly tried to lift her foot, but was unable. Her head sagged down again.

Mistress Jennifer mocked, "Such an embarrassing amount of semen. Nobody as pathetic as you could ever be called a 'man'. But, we can't let semen go to waste. You, girl, lick it up."

Sandra's chains released from her wrists and fell to the ground. She, too, fell to the floor in a broken heap. She was covered in welts and open wounds which oozed blood onto the stone.

Mistress Jennifer stepped over to Sandra and stood over her. She raised her heel and pressed it into one of Sandra's deeper wounds. Sandra screamed and pulled herself into a fetal position. Mistress Jennifer knelt down and pulled at Sandra's ball gag.

"Don't fucking touch her!" Marty screamed.

"Don't talk again, Slave." Mistress Jennifer ordered.

Marty felt himself unable to speak.

"W-w...why..." Sandra croaked. She screamed into the ceiling, "Why are you doing this!?"

Mistress Jennifer, still kneeling, delivered a harsh whisper into Sandra's ear, "I know you and your little friends think that just because this place isn't the real world that consequences don't matter. You tell me how real this feels." Mistress Jennifer pressed her finger into another of Sandra's wounds causing her to squirm from another wave of anguish, "You'd better start taking this seriously. You aren't here to be his friend. You aren't here to help him. This comes directly from the Doctor. Don't test him again or I'll show you just how real consequences can be."

Marty watched in horror. He tried to open his mouth, to leap out of his bounds...but he was completely trapped.

Mistress Jennifer whispered to Sandra once more, "Crawl, girl. Lick that tasty cum from your little boyfriend - and I mean little."

Sandra's body shook and she had visible struggle in her flushed face as she got up into a crawling position. Her legs and arms were slow to respond. She slowly and painfully began to crawl forward. Mistress Jennifer stood and had her signature evil grin.

Marty opened his eyes wide and tried to catch Sandra's gaze, but she was seemingly broken. She crawled underneath Marty, her long blond hair rubbed against his chest. He could hear her lapping up his semen. After a few seconds she retreated back and crawled to the wall where she lay in a ball, gently sobbing.

"Now, Slave," Mistress Jennifer said while turning her attention to Marty, "Seeing as how you failed the round, I'll be making a nice swap."

How could she still take something from him after all that?

"I think I'll send the majority of your leg strength to somebody I'm sure would want it. A little sissy slave like you shouldn't have all those muscles anyway."

Marty's legs tingled. He looked down past his shriveled, little, hairless cock and saw his thick, muscular legs beginning to recede. he could feel himself getting thinner and weaker as years of squats, lifts, kicks and all manner of training was wiped away. When they were finished, his legs were thin and had very little size. He had neither muscle nor fat, just two sticks between his straight hips and heeled feet. While still reeling from his transformation, Mistress Jennifer sauntered over and secured the chastity cage back onto Marty's cock.

As the scene collapsed, Marty tried one more time to get Sandra's attention. She was focused on the wall. He was soon floating in the dark.

[b]NAME: [/b]

Marty Lyonelle Dawes

[b]AGE: [/b]

21

[b]HEIGHT: [/b]

5"09

[b]WEIGHT: [/b]

159 LBS

[b]IQ[/b]

91

[b]POWERUPS:[/b]

0

[b]HAIR:[/b]

Straight, chin length black hair with long bangs. Silky and clean with a bit of sheen to it.

https://laristopa.smugmug.com/Story/n-crrWG8/i-VqVZ3dr/A

[b]VOICE:[/b]

A deep and gravelly, masculine growl.

[b]FACE:[/b]

Smooth, hairless face. Normal, if not slightly puffy lips. Low cheekbones and wide, somewhat prominent nose. Large, soft green eyes. Heavy brow and wide, square jaw. Normal sized ears. Wide neck with prominent Adams apple. Ability to grow facial hair is that of a normal woman.

https://laristopa.smugmug.com/Story/n-crrWG8/i-Sfrp3Fz/A

https://laristopa.smugmug.com/Story/n-crrWG8/i-dSHJ3Fq/A

[b]GENITALS: [/b]

Small, one or two inch micro penis with sad, shrivled balls. Smooth and void of any hair. Encased in a small, metal chastity cage.

https://laristopa.smugmug.com/Story/n-crrWG8/i-zKwGg9Q/A

[b]UPPER BODY:[/b]

Average to below average biceps and forearms. Smooth and hairless chest and slightly below average shoulders. Flat pecks with little muscle. Nipples are small hard and masculine. Stomach is hard, cut and muscled. Upper body is smooth and hairless. Hands are large and silky though masculine with rough nails.

https://laristopa.smugmug.com/Story/n-crrWG8/i-VpS6btN/A

[b]LOWER BODY:[/b]

Hairless, stick legs with little muscle or fat. Feet are large, smooth, masculine, without callous, reformed and requiring high heels at all times. Slightly chubby, protruding ass with narrow hips.

https://laristopa.smugmug.com/Story/n-crrWG8/i-tJqC9Qv/A

[b]OUTFIT:[/b]

Tall, leather heels.

[b]SEXUAL PREFERENCE:[/b]

Has dated exclusively women. Loves drilling a nice wet pussy. Loves making women scream in ecstasy. Likes large tits and big butts (and he cannot lie). Likes seeing women with cum on them (especially if it's his). Enjoys a bit of hair down there and has a preference for long blonde hair up top. Loves cunnilingus and anal - on both his partners and himself. Likes being the boss and having women call him 'Daddy'.

[b]PERSONALITY:[/b]

Somewhat driven and dim-witted. A bit of a hothead that's slow with his decision making. Somewhat provacative and foolhardy. Not overtly afraid of anybody or anything. Has very fast muscle memory and advanced general motor skills. A somewhat talkative introvert lacking a bit in confidence.

[b]KNOWLEGE/EXPERTISE:[/b]

Jiu Jitsu expert. Knows multiple fighting techniques other than Jiu Jitsu. Martial weapons expert. Very knowlegable about the human body inclduing fitness and diet (though he couldn't cook to save his life). Learned french exclusively for the ladies. Expert at walking in high heels. Has difficulty learning new things and working out complex problems.

Anthony Johnson: Round 1W, 10L, 12W

Annabelle Slut: Round 2W, 9L, 10L, 17L

Liam Gentry: Round 3L, 8L, 15L

Danielle Strauss: Round 4W, 10L, 16W

Cindi/Sandra Mode: Round 5L, 11L, 18L

Mrs. Polermo: Round 6L, 13L

S.A.M. / Samuel Kleiner: Round 7W, 14L

Mistress Jennifer: 14L, 18L