James Bondage Quickies (F*ta Femdom One Shots)

Three pairs of heels clicked down the sidewalk as Claire Thompson trailed behind two of her students. It was the last day of October and the usual scents permeated the crisp evening air. Dried foliage, autumn vegetables, holiday candy and semen. The occasion had been renamed Futaween many years ago, which was only too appropriate in this brave new world of ceaseless debauchery.

Once upon a time, young men went to college, vocational school or joined the military. Now, when they came of age, males were enrolled in Slave Training schools or the nearest Femboy Academy. Which one they were deployed to depended on a number of factors, from their body type and disposition to their mother's wishes.

Mistress Claire was a professor at one of these institutions, a career she embraced with great relish. Like virtually all women in the modern age, she'd opted to become a Futanari and enjoyed the many privileges inherent with her enhanced anatomy. No doubt remained that the world now belonged to her kind.

Jesse and Charlie marched just ahead of her, their pace guided by the twin leashes that led back to Claire's hands. Charlie was one of her many charges, but Jesse was more than just a student to her. He was also Claire's collared submissive and live-in slave. Each student was assigned a dominant Futa guardian so they could learn their proper role in the world as they completed their secondary schooling.

Their education never ended, regardless of whether they were in class or at home. Each young man served as housekeeper, companion and sexual servant to the Futa Mistress who took him under her wing. On the surface, it may have seemed like a conflict of interests to let a student be bound to a professor in this way, but in a world where any university professor could bend her student over a desk and take him at will, it was no longer seen as particularly troubling. Besides, many of the courses were sexual in nature, for masculine subs and femboys alike.

Charlie belonged to another woman, Claire's friend and colleague Elena. Elena decided to stay home this year to demand tricks from the neighborhood sluts and dole out treats to those who pleased her. Futaween was always a frenzied affair that kept her busy all night, so she'd handed over her obedient slave to Claire for the evening.

Elena was probably in a position to have more fun, but Claire didn't mind escorting a couple bubble-butt sluts around town instead. There was almost as much pleasure in watching them get ravaged and slathered in cum as there was doing the ravaging.

Jesse was dressed as a femboy incubus. Purple rubber horns sprouted from the base of his up-thrust blonde pigtails. They matched the color of his lipstick, while the pink hair-ties matched his dyed bangs. A pink collar with yellow spikes led down to a layer of black latex covering his upper chest and back. From there, a purple set of demonic wings extended, leaving nothing but a bare midsection and some drooping metal bondage rings.

Clingy nylons covered his forearms and legs, but left his ass exposed and his cock and balls dangling in the cool breeze. A short purple tail was glued to the skin of his lower back. Jesse's legs were consumed by rubber starting at mid-thigh, leading down into shiny heeled boots of midnight black.

Charlie was garbed in a demonic costume as well, though it hid much less of his body. The straps of a red leather bondage harness criss-crossed his form, leaving most of his skin exposed to the elements. Ironically, it was his face that was covered the most. All but his nose and mouth were veiled in red latex. The tight bondage hood featured twin black devil horns sprouting from his temples.

The red rubber covered his eyes, so he was relying on Jesse's instructions and the tug of Claire's leash to guide him where they were going. His arms and legs were decorated with torn nylons, leading to red leather gloves and a set of knee pads below. Charlie's circumcised sissy clit hung out boldly as they sauntered down the block.

For her part, Claire had added some angelic adornments to one of her university uniforms. It was only fitting that a Futadom angel would lead the two demonic slut boys around on Futaween. She wore a white suit jacket with black leather lining the cuffs and open front. Draped below it was a tight, white skirt. The sleek suit hugged her thick curves gracefully, showing off her impressive cleavage and creasing around her strong thighs. The dual leashes, one purple and one red, were held firmly in the grasp of her black leather gloves.

A small circlet sat atop Claire's head, holding a halo above her silvery hair. Sparkling blue eyes pierced through her thin, gold-rimmed glasses. It matched the large golden cross hanging above her bust, just as her white choker necklace complimented the rest of her outfit. Claire's gleaming white leather thigh-highs might've been the most eye catching element of her ensemble, if not for her massive mounds and the thick length of cockmeat jutting out from the bottom of her short skirt.

It was a chilly evening to have one's naughty bits hanging out, but that was part of the fun. It made things even more thrilling as you marched from house to house, looking for a door that didn't say 'Occupied', 'Busy', 'Tricked Out' or something more lewd like 'Fuckfest In Progress.' It was commonplace to have such signs on the door for Futaween to indicate whether visitors should stop and ring the bell or move on to the next house. They were fun indicators, but in truth, not really needed. You could often hear the moans and wails of bitchmade males through the thickest of front doors.

As they made their way down the street, Charlie stumbled for the third time and lurched to the side, grabbing onto Jesse for support. The blinded bottom almost dropped the trio's half-filled pumpkin bucket. The hefty orange container jostled and sloshed about with the treats they'd gathered thus far.

“Hey! Cut it out you clumsy bitch! You almost knocked me down again!”

“Sorry! I can't see anything with this mask on...” Charlie answered meekly.

“No shit! It was a stupid idea. Why don't you cut some eye holes in it?”

“Ummm, because I like sensory deprivation!”

“Pffft. Do that shit on your own time! This is Futaween and you're slowing us down!”

“Boys! BOYS!” Claire shouted. She reigned in both their leashes, tugging on their necks firmly. “Whoever starts the next argument is getting a spanking!”

They continued down the walkway, looking for the next house with abundant Futaween decorations and a well-lit porch. Jesse glanced to the side and noticed Charlie's upper chest jiggling ever so slightly as they walked. The beginnings of round, fatty tissue had started to form where a flat chest had previously been.

“So, you started hormones, did you?”

“Yeah. If you want to work at Femboy Hooters, it helps to have hooters.”

“Pfffft, I'd just strap on some falsies. Or maybe not. I bet they'd let me work there regardless.”

“You're dreaming.”

Jesse's brow furrowed in annoyance. He side-eyed the red demon slut to his left. “Fuck you! They totally would! And it's gonna be a long time before those little bitties of yours can be called hooters!”

“That's enough!” Claire announced, dropping Charlie's leash. She yanked Jesse closer to the side of the road, pulling him towards the nearest parked car. She tugged his leash until he was in range, then bent him over the hood of the red sedan.

“I think twenty strokes should do” she informed him, pressing his back down with one gloved hand and preparing to strike with the other.

“Yes, Mistress” Jesse replied with a knowing smile.

*SMACK SMACK SMACK SMACK SMACK*

As Claire's leather-clad hand lambasted his plump white tush, Jesse groaned and grunted pleasurably. Costumed onlookers, male slaves and Futa Dommes alike, looked their way as they continued down the street. The strangers laughed and enjoyed their little show, getting an eyeful before moving on.

This was a game Claire and Jesse played. They both knew that's what it was. He was always breaking the rules and giving Mistress any excuse to discipline him. Jesse was the ultimate brat and they both loved it. As the twenty strikes came to a close, he only wished Mistress Claire had mandated more. Jesse had an exhibitionist streak and found public punishment thrilling.

*SMACK SMACK SMACK SMACK SMACK*

“No more lollygagging or arguing” Claire insisted as she pulled Jesse back onto the sidewalk and took up Charlie's leash again. She strutted down the suburban walkway, pulling her naughty demonic whores behind her.

A few minutes later, the trio finally spotted a house that was open for business. They stalked up the driveway and hurried to the front door, three pairs of heels clicking away. When they reached the entrance, Jesse rang the bell and they waited a few moments in anticipation. The door opened and two large women were revealed. One was dressed as Snow White and the other was a witch in jet black leather. Both women sported eager smiles and sizable bulges in the front of their costumes.

“Ooooh, a couple sexy demons and a beautiful angel! How nice!”

“Hello my pretties!” the second woman added in her best Wicked Witch impression.

“Trick or treat!” Jesse and Charlie shouted in unison.

“Oh my! I don't know if we're ready for another trick so soon. We just sent some young men limping home” Snow White informed them.

“True, but a treat should be no problem” the witch assured them with a nod.

Snow White reached to an end-table in the foyer, grabbing two extra large condoms from their Futaween bucket of prophylactics. Within seconds, both hostesses hiked up their skirts and applied the long, thick lengths of clingy latex to their massive cocks.

The two Futa Dommes stood in the doorway, caressing their impressive endowments with long, deliberate strokes. They started slow at first, but their pace increased as the sissy sluts on the porch offered enthusiastic encouragement.

Jesse turned around and bent over the porch's railing. He thrust his ass back, showing off his demonic tail, his recently spanked ass and his rapidly hardening five-incher. Charlie set down their Futaween bucket before getting on his knees and entering a sexy pose. He opened his mouth and placed one finger on his tongue, just above its shiny metal stud. His four inch penis was rock hard below, sticking up and pointing at the pumpkin shell full of liquid goodies.

Claire watched the smutty spectacle with a hand on her hip and an amused grin. In the background, just beyond the two masturbating women, she could see a man in a black gimp suit being railed by another Futa matron. She was dressed as Princess Jasmine and it was apparent she'd chosen her Aladdin for the evening. His shiny bondage suit was already soiled with many thick blasts of sticky semen.

With their enhanced physiology and overclocked sex drives, it didn't take long for the door greeters to reach their fourth explosive orgasm of the night. Snow White and the fetish witch moaned as their climaxes arrived in quick succession. Fat streams of thick white paste erupted into their condoms, both lengthening into weighty pockets of rubber-wrapped cum. Just as their joyful groaning began to wind down, the blissful shriek of Jasmine could be heard in the background as she buried her pulsating staff in her rubber slave.

Still panting and sighing pleasurably, both women pulled the latex sleeves from their spent cocks and tied them off with a wet snap. They held the bountiful sacks of nougat filth up for the eager sluts to see before dropping them into the pumpkin bowl of butter-filled balloons. Each one landed with a wet thud as Jesse watched with hungry eyes and Charlie inhaled deeply the smell of latex and hot jizzum.

“Wait! Wait just a minute!” a voice yelled from the background.

Princess Jasmine made her way to the front door. Another fat, sludge-filled condom was pulled from her obscenely large cock. She knotted it at the end before tossing it into the bucket with a moist glug.

“What do you say, sluts?” Claire prompted.

“Thank you!!!” the demonic twinks answered in unison.

“You're very welcome” Jasmine answered with a grin.

“Looks like your bucket is almost full!” Snow White noted proudly.

 

* * * * *

 

After trudging around for another hour and filling a second grinning pumpkin with hot liquid treats, the tiring trio found a household that was eager to demand fresh tricks. They were welcomed in by a hulking, black-haired beauty dressed as Wonder Woman and a surly blonde dressed in the blue and black of a leather police uniform.

Claire handed over their leashes with no hesitation. The tall amazon took Jesse's while the truncheon wielding fetish cop scooped up Charlie's. The increasingly frustrated professor followed them into the living room. Her fully erect cum cannon was evidence she wouldn't be content to remain an observer for much longer.

Officer Misbehave led Charlie to a black leather couch and bent him over the side. She pressed his face into the soiled cushions with sadistic glee. Despite his total lack of sight, Charlie identified the sticky mess immediately by feel and taste. His face was being dragged through webs of residual spunk.

“Lick it up you filthy faggot! Every drop! Nothing gets me harder than watching a little fuck-boy lap up my leftovers!”

She pressed his back into the sofa with her billy club. Her other hand was busy unzipping her leather pants and summoning forth her sticky length of stiffening fuck-meat.

The armor-clad Diana led Jesse to a simple folding chair, likewise dripping in gooey semen.

“On your knees!” she commanded. “Stick your head through the hole and put your tummy on the seat.”

Jesse did as he was bade, scowling as his costume was gunked up by vestigial Futanari nut.

“Ugh! You could've at least cleaned this thing... OW!!!”

His wrists were seized by the strong woman and Jesse's arms were quickly wrapped around the sides of the chair. A pair of leather wrist cuffs and a short chain were applied, locking his hands and arms behind him. It wasn't the most comfortable position to get plowed in, especially with his knees raw against the hardwood floor, but that added a certain excitement to it. His peachy backdoor twitched, waiting to be filled with amazon cock.

The metallic ratcheting sound of constricting handcuffs sounded off in the background and Charlie's hands were trapped behind his back as well. Three hung Futa Dommes stroked their cocks, looking down at the two bound femboys as they writhed in delicious bondage and demeaning filth.

The bottom bitches eager moaning turned to exasperated yelps of brutal tightness and sudden pain as both hostesses went in raw. Charlie gurgled in cum-slathered leather as his face was forced into the cushion and a massive schlong sank into his dilating pucker. Likewise, Jesse grunted and groaned as over a foot of thick amazon cock entered his backdoor. The normally pleasant feeling stretched him far harder and faster than he was used to and his eyes went wide in shock.

“J-Jesus lady! You're big! Please be gentle!!!”

*SMACK*

Claire's hand streaked out and plastered the side of Jesse's face. She leaned down and grabbed one of his pigtails, yanking his gaze up toward her curvy form. Her rock hard length dripped pre-cum as it took aim at his quivering lips.

“Since when have you liked it gentle, you little skank?!?”

Jesse bellowed in pain as Wonder Woman seized his hips and tunneled in deeper. His body convulsed in the folding chair, but it was no use. With his head stuck out the back and his arms locked behind him, it was a simple, but brutally effective method of keeping a submissive bound and open to invading cocks. Jesse was positive Mistress Claire was taking notes.

“Do you mind if I join in?” Claire asked casually. “I've been a chaperone all night and I'm dying to get my dick wet.”

“By all means” the dark-haired diva answered as she pulled out and slid back into Jesse's luscious rosebud. “He could use a cock in his mouth to shut him up!”

“Agreed” Claire replied with a nod. The professor hiked up her skirt and lowered down on her haunches. She brought the weeping tip of her hot club of flesh to Jesse's squealing lips. Claire took hold of his pigtails in two firm grasps and silenced the bleating bottom. She shoved half her bloated length into his muttering mouth and stretched his dick pillows wide. Her glans glided all the way down his tongue to the back of the slut-boy's silken mouth and probed the entrance to his throat.

Jesse's eyes bulged as he gagged on her thick, pungent staff. He was used to deep-throating Mistress' weighty cock, but she usually gave him more time to adjust. There would be no gentle touch tonight. It was common for Futas to become more ferocious when they spit-roasted a slave. For Claire, it was even more exciting watching the amazon opposite her pound her collared slut with no lube.

The nylon clad incubus' outfit deteriorated as the two hung Futazons railed him at both ends. The chair rattled as he choked and sputtered around Claire's monster. His pucker slurped with the entry and exit of gargantuan Goddess cock and his wrists pulled on their bindings in vain. The dual Futa fucking was brutal and raw, and that only made his clitty harder. It expanded to its full, turgid five inches in record time as Jesse was reamed powerfully at both ends.

Charlie had almost cleaned the sofa cushions of cum by the time his arresting officer went balls deep in his boy pussy. He moaned long and low, his grumbles of pleasure coming steadily as she fucked him hard. Her hips slapped his exposed ass and her fat scrotum smacked his much smaller balls with forceful regularity. It was just the right amount of pain and humiliation to turn their energetic rutting into the ultimate pleasure for sub and Domme alike.

“More! Holy shit!!! Harder!”

His prostate glowed with budding pleasure as she pistoned more than a foot of bulbous cock into his yielding ass. Charlie's tongue lapped at the leather seating, searching for more spunk to feed his growing addiction. He shuddered in darkness, his eyes sealed under the latex mask as the mystery woman throttled, spanked and pounded him doggy style.

“Gladly, you horny little fuck!”

She dropped her truncheon and took up his leash. The leather wrapped Futa cop pulled on it with just enough force to choke Charlie lightly. He sputtered and moaned in bliss, the pressure on his neck enhancing the rapture of being bound and railed exquisitely.

Soon, all that could be heard throughout the quaint suburban home was the slurp of thick cocks in and out of wet femboy holes and guttural moans of pleasure . The three well hung women railed the two immobilized bitch boys into the night. Countless guests walked to the front door only to see the 'Cum back later!' sign and walk away disappointed.

After some twenty minutes of powerful fucking, Jesse's holes were flooded with a river of thick, hot paste. Claire and Diana went balls deep, keeping him air tight as thick ropes of seed clogged his luscious tunnels. Officer Deep-Dick covered Charlie's mouth and nose as she injected him with a torrent of warm, liquid justice. He snorted and mumbled around her gripping leather fingers as his intestines surged with clingy hot glue.

After pulling themselves free of the soiled slut boys, the haughty hostesses and Miss Thompson decided they wanted a second round. Wonder Woman and Claire moved to the sticky sofa to initiate a second spitroast. Charlie got a thorough taste of Jesse's ass when Diana pulled his mouth over her still-hard fuck stick. Claire entered him from behind and the little devil was being double-teamed in the cum-strewn darkness of his hood before he knew what hit him.

Jesse was a ripped, torn and battered mess, his makeup running down his face and semen dribbling from his splayed sphincter as he languished on the chair. At least he was lubed for a second entry as the eager officer lowered herself behind him and guided her steel-hard erection into his cum greased boy-hole. She grabbed a pigtail with one hand and the bondage rings of his latex top with the other, pulling his locked body into her hips forcefully. Jesse gasped and gurgled on Mistress' semen, still trying to clear his throat as his second ordeal began.

It seemed this was the final house they'd visit for this year's Futaween, but the festivities were far from over. It would be hours before the women were satisfied and even then, the holiday fun would continue. When Jesse and Charlie got home, they each had a bucket of condoms to chug.