Olive the Clown: Pudding on the Ritz (patron reward) (Patreon)

The return of Olive, the clown femboy working at a sexy carnival. We meet Olive's boss and learn just how little she'll put up with his shit!

Carnal’s Traveling Carnival was a place of old-fashioned horny fun for the entire (over 18) family. Olive was only one of the carnival’s many attractions, even if the mouthy femboy of a clown had his own strange way of luring people in.

Another start of the carnival was Pudding, who happened to be the assistant manager of the entire circus. She oversaw a lot of the behind the scenes matters while filling in as needed around the park, knowing her way around nearly everything they had to offer. With Olive out of the way for the day, she was managing the ticket exchange at the miniature arcade. It was a fairly comfy spot to be in when it came to Carnal’s, since she mainly just had to oversee the Jack-a-Mole game, the Lustin’ Roulette machine, and ski ball (just regular ski ball, thanks to the high demand) and let people cash in their tickets for vouchers, sex toys and souvenirs.

She was a short woman with dark skin, at least up to her neck. Around the middle of her throat she wore chalky white clown makeup complete with a black nose and black upper lip. Her hair was curly with a peachy pink color and a mockingly lopsided little bowler pinned off to one side. She wore fishnets around her thick legs and black shorts with a low-cut top done up in the traditional black and white stripes expected of a mime clown. She certainly wasn’t as silent as a mime, given her talent as a carnival barker when she was just starting out in the carnival.

She was enjoying her easy day when she saw a familiar face. She pursed her mismatched lips as Olive approached. Her mouthy coworker still sported his bright pink hair contrasting his white and black facepaint and bright red nose. He was dressed in some snug shorts and a croptop that cut off above his belly.

“Olly,” Pudding said in a nonplussed tone. “What are you doing here? It’s supposed to be your day off.”

“I know that! But why can’t I enjoy da show from the other side of tha booth for once?”

“In clown makeup,” Pudding pointed out.

“Not my fault I make it look cute as fuck.”

The carnival encouraged customers to enjoy themselves, and that included dressing up for the sexy games the carnival had to offer. It was why you found some women attending in full leather bodysuits.

Pudding studied him for a moment, looking for any ulterior motive. She finally shrugged.

“Suit yourself. You paid for it.”

She went back to watching over the arcade while Olive went off to peruse the carnival. She let him slip her mind while she checked some business emails on her phone, but he inevitably returned. He brought with him a heaping fistful of prize tickets.

“Boom! One blowjob please, baybee!” he demanded proudly.

Pudding looked up from her phone and stared blankly at the pile of tickets. She raised an eyebrow at Olive.

“Well that was fast.”

“I’ve been running half of those games for months. It’s all about knowing the tricks to milk ‘em for all they’re worth. Speakin’ of which, how about that prize?”

Pudding sighed and wheeled her chair back into a corner of her prize table.

“Alright. Get back here.”

“Nice! Nobody knows how to freakin’ blow a balloon animal like the boss clown!”

Olive strode behind her desk as Pudding rolled her eyes.

“Are you going to be like this the entire time?” she asked wryly.

“No promises.”

Pudding groaned and made enough space to get on her knees. Olive gladly pulled his cock out, already stiff for his pink-haired boss. The black and white lips wrapped around his shaft and squeezed their softness together around him.

“Damn, that’s good,” Olive moaned loudly as he gripped Pudding’s desk with one hand.

“You really aren’t clownin’ around when it comes to BJs.”

Pudding’s hair hung over her eyes, but she rolled them anyway. Her low grumbling was almost unnoticeable beyond the vibrations going up his shaft. Olive clearly didn’t mind the extra sensations.

“See, this’ why I love puddin’ my stuff in your face, Puddin’,” Olive went on with his punning praise.

“Nothin’ like putting some cream on top of your pudding, am I right?”

Pudding groaned and furrowed her veiled brow. She bobbed her head and curled her tongue, wrapping it warmly around Olive’s cock. She lathered it up with her saliva, letting him feel the slowly trailing spittle running down his balls. Anything to make him finish quicker and get him to shut up with the gags.

“There ya go, boss. Squirt the clown and make ‘em pop just like in the game. Nothin’ like havin’ a nice tent pole in your big top, is there?”

Olive started pumping his curvy hips, thrusting harder into Pudding’s mouth. Her Oreo-colored lips tightened in annoyed surprise, even if she could take his cock with little trouble thanks to all her experience. She couldn’t help thinking he was doing it on purpose at this point.

“Of course a clown’s gotta love a cream pie, right? Maybe I’ll even bust your balloons after… AH~!”

Olive gave a short, high-pitched gasp. Pudding’s fed up growl vibrated tightly enough around him that he nutted inside her, squirting her tongue and throat with his seed. She didn’t even finish gulping it down before she pulled back, letting his jizz sputter out onto her chin and chest.

“There’s your prize,” Pudding said, wiping off her painted lips.

There was a tension to her voice that Olive picked up on, but she had a smile curling across her face. What was more, her voice was raised like she had when she was calling for the attention of an audience.

“But it’s your lucky day! Time for your BONUS PRIZE!”

Before she bothered rising up, Pudding grabbed Olive by the hips and pushed him into her prize desk. He connected waist-first, making him double over it with his leaking cock dribbling on the floor. A small crowd of nearby patrons were starting to stare and gather to see what Pudding was barking about.

“Hey, uh, that’s not necessary. I can just take one of those gag condoms instead...” Olive started but Pudding was already dipping into the prize cabinet.

She came back out with a purple strapon, slinging it over her curvy hips and coating its shaft in a colorful lube. She grabbed Olive by his plump ass and parted his cheeks, kneading and slapping them around. Olive’s eyes widened as his painted face looked panicked.

“Seriously, boss. I wouldn’t have pegged you as the punishing type…”

“Okay, that’s it!”

Pudding plowed the slick sex toy up his ass. Olive gave a girly squeal as he gripped the desk, bracing himself as his manager fucked him hard enough to make his cheeks pancake out against her lap.

“You have any idea how much I have to do around here?!” Pudding scolded him sternly.

Olive’s eyes rolled up towards the ceiling as he panted. His prostate was being pounded so roughly that he couldn’t think straight, and his tongue rolled out past his painted lips.

“Last thing I need is you coming in here slinging cum and puns around just to annoy me on purpose. You! Little! Bitch!”

Olive let out a shrill wail as Pudding spanked his ass, thrusting in deep with each of her last insults.

“Sorry, boss! I was just havin’ fun! I wasn’t trying to Pudding you down!” Olive pleaded.

“And you NEVER shut up!”

The high pitch and quiver to his voice showed he wasn’t totally hating the rough treatment. His legs quivered as he squirted another orgasm under the desk as his body reacted to the bittersweet punishment. The customers certainly enjoyed the show as he was fucked silly, but that was a sidenote at this point. Olive was used to it after working in the horny circus for so long.

It gave Pudding an idea, though. She pulled back out of the panting femboy and turned to the newly gathered crowd. She smiled and gave a theatrical gesture, waving towards the air while shaking her hips suggestively.

“STEP RIGHT UP, FOLKS! WE GOT OURSELVES A CARNAL CARNIVAL SPECIAL GOING ON TODAY! FOR THE NEXT TWO HOURS, IT’S A MERE 100 TICKETS FOR 1 MINUTE OF DOING ANYTHING, AND I MEAN ANYTHING, TO THIS PRETTY LITTLE PIECE OF CLOWN CUTIE!”

“What?! H-hey, you know this is my day off, right!?” Olive tried to point out in his moaning voice.

There was already a line forming as Pudding stepped out of her strapon. She sat on Olive’s back, her shapely ass pinning him to her desk as she started gathering tickets. She ignored his weary objections as she started gathering tickets from the waiting customers and went on with pimping the femboy clown.

A large jock of a man moved in behind Olive. He dropped his pants and buried his large shaft into the clown boi’s butt, proving himself even bigger than Pudding’s strapon. His already lubed up anus made for a smooth ride all the same as his legs tensed up from the fresh pounding.

“Ohhhh! F-fuck… anybody tell you that for a clown, you sure can’t take a joke?” Olive groaned back at Pudding.

“His mouth is still open for use, folks,” Pudding reminded the crowd.

“Anyone looking to get a little makeup on their goods?”

A tall woman with short brown hair stepped out in front of Olive and grabbed him by the hair. She adjusted his face to go up her skirt and into her pussy. The clown was startled but instinctively started working his tongue and lips against her slit. They dug in deeper as the man behind him plowed him hard, making him rock back and forth between the customers.

“Dibs on his dick,” another cute-looking girl chimed in.

She happily passed off the tickets to Pudding as she squatted under the desk, catching Olive’s hard and leaking dick between her lips. She moaned as it wagged inside her mouth, rocking from the fucking going on above the table. She started to play with his balls as she pleased, squeezing or spanking them to her heart’s content.

Much like Pudding before him, any protests from Olive were quickly drowned out. He could barely be heard through his mouthful of pussy and his brain quickly slipped into a bimbo-like state as he was fucked silly on all sides.

The fuckboi of a clown shot his load even more than the customers as they used his holes and toyed with his dick while Pudding gathered the pay. She just smiled contentedly as she stayed on Olive’s back. He clearly wasn’t going anywhere, so at this point she was just doing it for the spectacle and to enjoy the ride of his swaying body.

It took quite a while, but eventually the line dwindled. People had finished in or on him and gone to get some refreshments or take a break. While they’d had their fill, Olive was a drained and sloppy mess on Pudding’s desk. She finished folding up the tickets and sorting the cash before stashing them away.

“There. If that’s not enough of a prize for all those hard-earned tickets…”

Pudding went back to the cum-caked clown and tucked a couple tickets into his shirt pocket.

“Go have a soda or something. You earned it, Olly.”

Olive was barely aware of anything at the moment. The sexually punished clown’s eyes rolled as he was limply draped across her prize desk. He just moaned sleepily as he gulped down some leftover cum from his mouth.

“This... better count as overtime…” Olive groaned before flopping listlessly over the desk.