Mistress Cruel Love Ch. 04

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

"Kneel!"

Darius was caught off guard and hesitated briefly.

"DO WHAT SHE SAYS, DANA!" Heather shouted from the front row.

"DO WHAT THEY ALL SAY!" Beatrice followed up and the crowd laughed.

He lowered himself to his knees as Mistress Styx closed the distance. Her boots halted inches from his face and she placed her left one directly in front of his mouth.

"Lick."

He didn't hesitate this time. Darius extended his tongue and applied his wet flesh to her boots in wide swaths. One look at her was instructive on how much she wanted to use her crop. He didn't wish to give her any extra incentive.

*SWAT*

Despite his eagerness, her leather weapon whistled into his exposed behind.

"Faster, slut. I don't have all day! EVERY INCH OF MY BOOTS!"

Darius glided his tongue up and down the soft leather of her shiny knee-highs. He cleaned the pungent footwear as quickly and thoroughly as possible, the thick taste of leather building up on his tongue. As he performed his boot-licking duties, he could hear objects being setup on the stage around him. Mistress Styx was giving her crew time to prepare the rest of Darius' ordeal. She pulled her left boot away and planted the right one in front of his face so the work could continue.

*SWAT SWAT SWAT*

Three more lashes whipped into Darius' ass to provide encouragement.

Much of the crowd had moved to the food tables and begun choosing their courses from the extravagant catered smorgasbord. Some were at the bar getting fresh drinks. Others were still in their seats, enjoying the sight of a sissy maid polishing a woman's footwear with his tongue. Chatter and the occasional hoot of laughter echoed around the hall as Darius slobbered away.

"ENOUGH!" Styx announced and withdrew her leg from his mouth.

The leather-clad enforcer stomped away and left him on his knees. Within moments another Domina carrying a large wooden paddle and a leash strode into view. She clipped the leash on Darius' collar and began petting his face softly with her latex fingers.

"Alright doggy! Time for you to get some exercise. Try to keep up now!"

The woman strode away and yanked his collar, imploring Darius to follow. He crawled as quickly as he could on hands and knees, but the heels made it difficult and he was never fast enough. She pulled on the leash harshly and forced him to shamble behind her even faster. The front of his maid costume dragged across the stage as she led him around, getting dirtier by the second.

Within moments they were in front of an obstacle course. His new Dominatrix pointed to the elaborate layout of cones and upturned hoops and beckoned him to action across the stage.

"Around the cones and through the hoops! Don't screw up or you have to start over!"

*SMACK*

The wooden paddle blistered his ass and Darius took off on hands and knees. He began worming his way around the silly display, weaving through the cones and climbing through the hoops as fast as he could.

*SMACK SMACK SMACK*

"FASTER!" The woman called out, following alongside him and delivering a blow of encouragement whenever she felt like it.

With each hoop he lumbered through, the demanding Domme would beat his ass hard. His dress offered some cushioning, but she wasn't being gentle. His ass was growing increasingly red and painful the further he proceeded.

By the time the course was done, Darius' heart was beating like a jack rabbit's. Domina number two left him on hands and knees to catch his breath as Domina number three approached. Another pair of black boots strode into view and Darius was too tired to even look up. He soon realized he wouldn't need to as the woman knelt down and slid a large bowl in front of his face.

The metal bowl contained a messy mixture of many foods. Mashed potatoes, vegetables, gravy, pieces of bread. There were likely more components, but those were the ones that stuck out to Darius immediately.

"You must be hungry by now" the Femdom announced as she placed her hands on her hips. "Start eating, bitch! No hands allowed."

Darius ducked his face into the bowl and started lapping away. He wasn't even surprised when she placed the tip of her boot on the back of his head and pressed his face into the bowl of muck. The audience roared and cackled with glee as Darius got his first dose of wet and messy play.

When she finally let his glop-smeared face up for air and the discolored potato slurry fell from his eyes, he looked across the stage and saw three more Dominas waiting to have their fun.

* * * * *

"GLRRRRRMMMMMMMPPPHHHH!!! UURRRMMMPPPGGGHHHHHHH!!!!"

A fat, purple strapon slid between Darius' sucking lips as a giant white rubber cock was fed into his stretched-wide asshole simultaneously. Mistress Styx was at his rear, pounding his sissy pucker through ripped pantyhose as the other Domina held his ears firmly and sawed saliva-strewn strapon deep into his throat. Darius sputtered and gagged as the women thrust their hips forcefully, mocking him and laughing as they spit-roasted him before a captivated audience.

He was secured to a bondage horse with his wrists and ankles chained to the sides. His maid costume was completely defiled, covered in sweat, spit, food and the dust and dirt of the stage. The horse rocked slightly as the aggressive women poured all their energies into assaulting his waiting holes. That was all he was good for since they secured him to the horse. He'd already endured the other four Mistresses fucking him at both ends with their giant rubber cocks.

His asshole ached and burned as Mistress Styx railed him with the biggest one yet. It had to be at least as big as Heather's Moby Dick. Maybe bigger. The veteran Domina had been pleasantly surprised Darius could handle the massive schlong. Many sissies before Dana had failed to.

"Did you think just because you did a nice little dance we wouldn't treat you like the COCK WHORE you are?!?" she yelled as she hilted the thick strapon in his ass. The toy's massive rubber scrotum smacked into his own and his penis bulged in its stinging, metal prison. He'd already cum twice from being assfucked before a live audience and he was on the verge of another stinging orgasm.

Styx gathered a good amount of spit in her mouth and lobbed a fat, globular loogie onto Darius' back. The Dominatrix at his front pulled her cock from his sucking lips and lit his face up with her open palm.

*SMACK*

"DEEPER WHORE! THROAT ME TO THE BALLS!"

"RRMMMMMMHHHHMMMGLLLPPHHHHHH!"

The dripping rubber missile plowed into his mouth once again. Her manic thrusts drove the spongy cock-head past his uvula and deep into his phlegm-clogged throat. Darius sucked away greedily, moaning around the strapon as his chained limbs rattled below.

"Cmon you sissy bitch! One more time!" Styx cried out as she dug her hands into his sides and smacked her hips into his ass with pounding thrusts. "SHOOT YOUR SAD LITTLE LOAD OUT OF YOUR CAGED DICKLET YOU FAIRY FUCK!!!"

"SUCK HARDER, SLUT! The crowd wants to hear those pretty noises!" the woman at his front yelled. She took a firm grip of his hair and plowed her strapon in and out of his stretched mouth. He slurped on her silicone dong with fervor, doing his best to produce the loudest glomming and gagging sounds he could for the depraved audience. Caked food and the runny remnants of makeup oozed from Darius' face just as the thick combination of saliva and lube dripped from his pursed, dick sucking lips.

Their verbal abuse and Styx's assault on his prostate forced Darius into his third public orgasm. He convulsed on the bondage horse as his half-hard penis strained painfully against its metal housing. His constrained, black clitty ejaculated for the third time that evening. The two Dominas continued to assault his ass and mouth, making sure every ounce of his sissy filth was spat into his already-soiled panties. A cheer and round of applause went up from the crowd as Darius' third spit-roasting drew to a close.

When he was done moaning and yanking on his bonds like a bitch in heat, the delighted Femdoms pulled their cocks free. Two loud slurps announced their exit as webs of sticky saliva slid from Darius' mouth and frothy anal juices dripped from his blown-out pucker. He lay there with his head resting on the surface of the bondage horse as he wondered if his public defilement was finally over. He learned within seconds that it was not.

"Alright maids, gather around our star sissy!" Mistress Styx called out. She hadn't bothered to unstrap the massive white dong from her waist. It bobbed in front of her as she whipped the group of sissies into order with her crop. The contingent of club maids encircled Darius, stepping ever closer to his bound and disheveled form. He noticed that Riley and Lexi were among them.

"Time for the big finish! Get to it you filthy sluts!!!"

At Styx's command, the sissy maids lifted up their skirts and began pulling their panties down one by one. Their cocks were freed and soon six silky gloved hands were working back and forth on six soft sissy cocks. The maids began moaning and sighing in pleasure as each slowly worked themselves to full mast.

*WHAP*

*SMACK*

*WHIP*

*THWAP*

The Dominas each took up position behind one of the maids and rained their encouragement on each sissy ass.

"Get hard faggot!"

"Hurry up you fucking cunt!"

"Do you want to cum today or not?!? This is your only chance!!!"

The faces of the sissy maids grew red and euphoric as their cocks strained and they took perverse pleasure in their ass beatings. They stepped even closer to the bound sissy star, their cocks on the verge of exploding. Slick fapping sounds came wet and fast as blows continued to flail away at their sissy asses. Lexi was the first to scream in climax.

"AAAAAAAAHHHHHHHHHHH!!!!"

Her thick, viscous seed shot all over Darius' face as she masturbated furiously. The sissy's face was a mask of ahegao contortions as she held her dress up with one hand and her silken fingers were a blur, stroking up and down her exploding phallus. Every time he thought the last wad of sticky filth had plastered him, another followed. She continued yelling in climax as every bit of stringy butter was milked onto his hair, forehead and cheeks.

The other maids erupted in climax sequentially, ropes of thick batter blasting Darius from every angle. His already ruined costume was treated to a sissy maid bukkake. The pungent spurts of sticky nut kept coming and coating him like a pastry. Riley fired his sissy load all over Darius' recovering ass-crack, his glue-like semen trickling down the star sissy's ass and thighs.

All six sissy maids groaned in climax and emptied their balls on the newest member of their clique. The crowd roared with approval and before long, the last shot of sissy yogurt had been fired onto Darius' back. He lay in a heap of filth until they'd all finished and Mistress Styx nodded to Lexi and Riley. His backup dancers mercifully unchained him and Darius was able to slide off the sticky bondage furniture. He steadied his weary form carefully and turned to the crowd, displaying the tattered remnants of his uniform and his thoroughly defiled body.

Below, Darius could see a cake had been wheeled out to just in front of the stage. It was lit with a large ring of candles and the top had a frosting inscription that read: "HAPPY SISSIFICATION, DANA!"

Heather walked up the short staircase and onto the stage as fast as her thick thighs could bring her. She looked overjoyed as she strode to Darius, her bulbous curves bulging through the tight, purple evening wear. She stopped in front him with a beaming smile, but said nothing, at first. His Goddess reached into her pocket and then leaned down and took a knee.

The crowd grew quiet at the unexpected development. Heather, so used to towering over her man, looked up at her filth slathered sissy with hopeful, shimmering eyes. She opened the small jewelry box in her hands and displayed a modest diamond ring to Darius.

"I've never been more happy, more aroused or more in love than I am right now. Marry me, Dana!"

It was more a command than a question, and that was fitting. Posed as a question, it would've been rhetorical. Heather knew the answer and so did Darius. The crowd knew the answer. The whole damn world knew the answer. The word no didn't exist in his vocabulary any longer.

Despite his ruined state, a broad smile spread across Darius' lips. His heart soared as he realized with sudden clarity that he'd never been happier than he was at this moment. He would never again be burdened by decisions. The woman he loved had unveiled his true desires and given him all he ever could've wanted. His future was no longer in his control and that was a beautiful thing.

"I love you so much, Mistress. Of course I'll marry you! I'm yours forever."

Club members, Dominas and sissies alike shouted in approval and applauded wildly. Heather rose and embraced her soiled submissive, bending him over as they kissed long and deep. All apprehension, doubt and reservation that remained in Darius sailed into the sunset, never to be seen again.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
Share this Story

READ MORE OF THIS SERIES

Similar Stories

In Time for Summer A boy gets seduced by his "lesbian", packing roommate.in Transgender & Crossdressers
Futa House A boy unwittingly discovers a gold mine of girlcock.in Transgender & Crossdressers
Life on the Ranch Ch. 01 Our new ranch hand is a woman with a little something extra!in Transgender & Crossdressers
"What Does She See in Him?" A high school boy finds the girl of his dreams is a bit more.in Transgender & Crossdressers
My New Trainer Workouts will never be quite the same.in Transgender & Crossdressers
More Stories