You Bet Your Ass!

Story by Duxton on SoFurry

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After V&V, I figured those of you who prefer M/F stories deserved a little treat :)

Based on a joke that I was told by a friend of mine. The joke involves two men and a banana, but I figured I would change it up a little bit.


"Come on, I'll give you three to one odds, three to one!"

Private Mack Stewart's pleas for another chance to swindle his fellow soldiers out of their hard-earned money fell on deaf ears. Groans and dismissing waves were all he got in response to his cheesy grins and empty odds. Grinning smugly to himself, he gathered up the money he'd won, licked his thumb, and began counting it out. Once done, he stuffed an easy eighty bucks into his trouser pocket.

Private Stewart's gambling did not go unnoticed by his commanding officers. A friendly, five-dollar bet of how long it would be before heavyset Corporal Chadwick collapsed during the road march, or whether Private Sneed would pop hot for dope on the next drug test was overlooked and sometimes even laughed about, but the sneaky fossa was as crooked as the weasel he was so often mistaken for.

Rarely were bets won against Mack Stewart, and rarely were they lost for less than twenty dollars. It started innocently enough - he'd won a collective pool of over five hundred dollars when Corporal Chadwick gave out before the second mile mark; a lottery everyone had willingly participated in, save of course for Corporal Cholesterol himself.

Nicknames were not uncommon in the military. Private Stewart had earned himself 'Slick', after a particular lucky streak of bets left him thousands of dollars richer at the expense of his comrades.

Guilt was not in his repertoire of emotions. The way he saw it, he'd been gifted with a knack for conning others. He reasoned it was on them not to be conned, natural selection at its finest. All he could do was hope to skirt the IRS' radar come tax season.

Naturally, Stewart's command decided not to address the issue until it was so dire that a lack of motivation was a major factor in the efficacy of their operations. Private Stewart was summoned to the Commander's office later that day like a child reporting to the principal at school.

"Have a seat, Stewart." Captain Brunson said, gesturing with one hand to a chair across from him, returning the hand to its clasped position with the other over his uniform top. Tentatively, the fossa took his seat and wondered if they had found out what he'd bought with his Government-issued travel card.

"You're being reassigned to a different duty station. You'll no longer be with this unit."

"What? But sir, all my friends-"

"Stewart, you have no friends here. You've swindled and cheated so much out of your fellow soldiers that they can't even trust you anymore! What does that tell you?"

"Well, where are they going to send me?"

"Kilo Company, Two-forty-four." Captain Brunson stated flatly. Private Stewart came out of his tree, only barely keeping his composure in his seat.

"Oh, sir! Please, sir, I can change, I promise!" He pleaded. The Captain silenced him with a hand and a stern look - all it took for a good Officer.

"You'll be going to your new unit tomorrow morning at 0800 hours, immediately following formation. I expect you to have your things packed and ready to go. You will also be required to attend a program to assist you in recovering from your...gambling addiction." Brunson said, tacking onto the last few words a break in eye contact and the kind of disgust that showed just how embarrassed he was to have a soldier in his company with such an ailment.

Private Stewart walked back to his barracks room with the kind of dejectedness that spoke louder than any words could. Anyone who saw the slump in his stride grinned gleefully, knowing that the news - for them at least - had been good.

A couple of hours later, poor Mack was left with little more to do that sit on his bunk, tossing playing cards into his patrol cap. The barracks room was spotless, and as empty as the day he'd moved into it. He spun a Joker between two finger claws and paused for a second, looking at the Jester in the picture, grinning back at him like an idiot. Frowning, he whipped it into his hat, lying inverted across the room.

Once out of cards, he stretched out, lying on the naked bunk and staring up at the ceiling tiles. He tried to look at the bright side, a new unit meant new comrades, and new comrades meant new victims. He sighed when he thought about the rehab program he'd be attending against his will - that's being Government property for you. He'd continue to supplement his income either way.

The bright side wasn't very bright, but at least it was there.

***

"Here are your orders. Report time is 1100 hours. Don't be late. Your POC is Captain Wells. Any questions?"

"No, sir." Mack said quietly, taking the orders from Captain Brunson and glancing over them before folding the paper up and stuffing it into his trouser pocket.

"I'm disappointed to see you go, Stewart. You have the potential to be a great soldier; you just have to get your gambling problem under control."

"Yes, sir."

In keeping with tradition, Private Stewart snapped to the position of attention, and brought a bladed hand up to his brow in a salute and a wink, which was returned in kind by the Captain. He executed an about-face, and marched to his car with nary a look in the direction of the barracks that had been his home for the last year.

Two-forty-four was across the base, but it wasn't far away. Mack found himself in front of the barracks less than ten minutes after his departure from his previous unit. Even though it was so close by, he felt as though he was in a strange and foreign land, unsure of what to expect.

Just inside the door, he was met by the Charge of Quarters, who directed him to the commander's office. Down the hall, first door on the right. A placard on the door just below the room number bore the Captain's name. Sighing, he raised a fist and held it aloft for several seconds before bringing it three times sharply to the plank.

"Private Mack Stewart reporting as ordered."

"Come in."

Stewart grabbed the handle and pushed the door open, then turned his back to the Commander as he shut it behind him. As soon as the fossa turned, he found himself face to face with a vixen, her uniform bearing the rank of Captain.

Mack's brain immediately short-circuited. Captain Wells was easily the most beautiful woman he'd ever laid eyes on, let alone the most beautiful Officer. Her blonde hair was tied back into a tight bun behind her head in keeping with Army regulations, and Mack found himself envisioning her with it down, long and flowing, cascading down her back to what he was certain was a dynamite ass.

Captain Wells' uniform left little to the imagination. Her thighs spited a uniform infamous for diminishing any discernible figure, and her ass filled out the seat of the camouflage trousers in a way that simply imagining how it looked in a pair of low-rise blue jeans would induce an erection hard enough to cut glass. Her impressive bust distended the top half of the uniform to such a degree that it almost seemed to push her rank out, imposing it upon the shrewd fossa. He couldn't wait until morning PT.

"I said, 'stand at ease', Private!"

Easier said than done. It was a little too quiet for comfort. Stewart slowly moved to the correct position and gulped, sneaking in a few seconds of callous staring while she opened his records jacket and skimmed over it.

"So, Private." She said, tapping her claws on the arm of the chair, "I hear from Captain Brunson that you've got a gambling problem, is that true?"

"No ma'am."

"No? Are you saying that Captain Brunson is lying to me? Do you think we're sending you to a recovery program for shits and giggles?"

"No ma'am, it's just..."

"What?"

"It's just that I wouldn't call it a problem."

"Really? And why do you say that, Private Stewart?"

He shrugged.

"Because I win every bet that I make." He stated plain as day. Plaintive in demeanor, aloof in attitude, he could tell already that his new Commander did not like him. Her gaze was cold, calculating, and borderline malevolent.

"That a fact?"

"Indeed it is, yes ma'am."

"Okay, Private. I'll call your bluff." The vixen sat back in her chair, folding her arms over her expansive chest and staring him down from across the room, "Make me a bet you can't lose."

Private Stewart's mouth opened, but no sound came out. Green eyes flicked southward, then back up to her. She raised her eyebrows, waiting patiently. Mack closed his mouth, then opened it as he spoke, wagering the most ridiculous bet he'd ever made in the history of his career.

"I'll bet you've got hemorrhoids."

Captain Wells' jaw dropped, and she stared in shock as the corners of the fossa's mouth turned ever so slightly upward in the cheesy grin he'd become infamous for back in Bravo Company. It was all he could do. He couldn't believe he'd said it. So much was riding on that bet. He began to contemplate the potential repercussions of his quip - at the worst his career would be over. At best, she'd have him doing push-ups until the sun went down.

Finally, after several long, tense seconds, the vixen began to laugh in disbelief. She tossed her head back and laughed up at the ceiling, then bent forward and laughed some more into her lap, shaking her head back and forth, slapping the armrest of the chair with her palm.

"Private, are you serious?" She managed.

"I'm serious."

"Private Stewart, I've been called a tight-ass around here, but that's a take on it I've yet to hear. Congratulations!"

"Do you accept?" He asked. It was Mack's turn to wait now. A few seconds later, the vixen collected herself and cleared her throat, smoothing out her uniform and pulling it taut over her ample bosom, further absentmindedly teasing the fossa. She wiped an errant tear from her eye and chuckled.

"Okay Private. What do you wager?"

"Twenty-five hundred dollars." He said plainly. Wells hadn't expected such an amount, but her confidence carried her decision forward in the form of a handshake.

"You're on, Stewart."

"Good."

"So how exactly do you plan to verify that?" Wells asked, ever the skeptic, "I could just as easily forge a report from the medics and you'd never be any the wiser."

"We drop trou, I stick my dick up your ass, and if it comes out without any blood on it, you win."

Captain Wells' face darkened.

"You're way out of line, soldier."

"No one has to know about it, do they?" Stewart asked softly, reaching into his pocket and pulling out a roll of cash, twenty-five one hundred dollar bills in all. He could see the avarice in her eyes as she stared at the money. He fanned it out so she could see how much it was, then tossed it onto the desk - quite literally a pile of free money, two-thousand five-hundred dollars in all. Free, with the exception of anal sex with a subordinate, something that was strictly forbidden. Looking none too pleased, Wells glanced down at the money, then up at Private Stewart.

"If you tell anyone about this, you will not only lose your career, I will make sure you never have another one, anywhere, for as long as you live, you got that?"

"Yes ma'am."

"I will not only do that. I will spend the rest of my life making sure that yours is absolutely miserable. I will be like a poltergeist to you, like a bad itch that you can't scratch, understood?"

"Yes ma'am."

"No, forget all that." She said, walking around the desk and getting right up in Private Stewart's face, "If words of this gets out, if you tell anyone, and I mean anyone at all...I will kill you. Are we clear?"

Mack just grinned smugly in the face of impending doom, the clinking of his belt buckle the only sound in the room just before the _shuff_of his pants and underwear being pulled down. Still scowling at him, the voluptuous vixen strode past him, locking the door to her office. Crossing the office in a few long strides, she drew the shades, sealing them off from the rest of the world.

"All right, let's get this over with." Captain Wells stood there for a moment, secretly admiring the fossa's erection, though outwardly, she seemed unimpressed. Somewhere in between, she was frightened; she'd never been with a man with a penis as big as Mack's, and his was well above average. She fiddled with her belt for a moment, the two ends hanging while she unbuttoned her trousers and pushed them down to her knees, revealing a pair of purple and white, lace-trimmed panties stretched drum-tight across her hips and butt.

"Are those panties authorized for wearing with the uniform, ma'am?"

"Shut up."

She turned around and grabbed her panties at the hips, shimmying out of them, bending one knee, then the other as she tugged them down to about mid-thigh. Once there, she placed her hands on the desk and bent over, moving her bushy tail and displaying her perfect, pornstar quality ass to him. In the middle, a flawless, pink slit glistened, beckoning him with the warm tightness that was her vagina, but even he dared not try. Just above that was his target, that tight, pink pucker that would probably lose him a good sum of money, but he had plenty to blow - in more than one way.

"Got any lube?"

"Private, why would I have lube in this office?"

"Oh, I don't know, maybe for situations like this?"

"Don't get smart with me, Stewart, just figure something out. And don't think for a second that I'm putting your dick in my mouth!" She hissed over her shoulder at him, trying to be quiet. Mack simply shrugged and dropped to his knees behind her, immediately grinding his muzzle into her ass, his tongue lashing violently out at her tailhole, circling it, pushing into it, and feeding as much of his saliva onto and into it as he could; it wasn't his preferred method, but he would be damned if he wasn't going to make it work.

"I think you're enjoying that a little too much back there, Private. And stay away from my pussy!"

"Yes ma'am." He said, somewhat disappointed, but he had to pick his battles. He stood back up and grimaced as he spit into his own hand, using that to slicken his throbbing dick in preparation for his entry into one of the tightest asses in the military. One hand on her hip, the other around his dick, Mack pressed his tip up against her pucker, slowly applying pressure and listening to the breaths that if she'd let them, would have been moans.

"Don't cum inside me..."

"Hey, give me some credit! I can last _much_longer than this!" He stated defensively, disappearing into her bit by bit until half of his pulsating, nine inch-long erection was sheathed inside her. Now with both hands on those curvy, velveteen hips, Mack grunted and shoved the last four inches of his dick into her with one solid push, eliciting a stifled cry from the Captain as his balls slapped her in the pussy.

"Hah, I knew you were enjoying this!"

"Shut up, Private! Pull it out and let me see."

Mack slowly pulled his penis out of her and she turned around to see that that throbbing, rock-hard boner was as clean as it had been prior to their short-lived encounter. Not a speck of blood was on it.

"You win, fair and square." Mack said, grinning smugly and watching her scoop up the pile of money and count it out, twenty-five one-hundred dollar bills.

"You're dismissed, Stewart. Remember what I said." She ordered, stuffing the wad of cash into the pocket on her sleeve, since the ones on her pants were down around her shins. Mack shrugged and looked down forlornly at his erection, sticking straight up in the air and looking right back at him.

"We've come this far, you want to finish it?" He suggested. She shot him a look that suggested she most certainly did not.

"I mean, you're just going to go masturbate anyway. Wouldn't you rather have the real thing?" Mack was a pretty good salesman, aside from being a master con artist - he could see the resolve in her eyes fleeing, and the decision behind them when she finally made one.

"Fine." She said with finality in her voice, "Same rules apply."

"Including the one about staying away from your pussy?" He asked. She chewed on the inside of her cheek in thought.

"Just don't finish inside me."

"Got it. You know, I've only got so much spit...you mind pitching in?" He said with a wink, and gestured with his head towards his cock, standing proudly away from his body, just begging to be sucked - something Wells finally agreed to do after a moment's hesitation.

Down on her knees in front of him, she wrapped those thin, vulpine lips just behind the bulging head of his penis, using her thin, coarse tongue to stimulate it to the point of leaking his precum into her warm, wet muzzle. Every time that tiny little slit gushed forth with a drop, it was licked up before it could even bead.

One black-furred paw worked its middle and ring fingers between her legs, and the other one was unzipping the top that covered her voluptuous chest. She had to remove Mack's erection from her mouth to take off the T-shirt she wore underneath it, but the moment that the garments were in a heap on the floor beside her, that massive member was back in her muzzle, and she wasn't holding back. Wells began to suck the cock in her muzzle such fervor that one might have thought his cum would be the first thing she'd had to eat in days.

Mack began to remove his uniform top and T-shirt, staring down at the Captain's cleavage all the while in her plain, black bra. With two-thirds of his penis in her mouth, keeping it hard was a non-issue, but with the picture he had to look at, he felt as though he could stay hard for a month. Nevertheless, the position was growing tiring, and he needed something to do. So he lay down on the carpet, holding his cock upright and stroking it while Wells pulled off her boots, socks, and pants. He had to stop masturbating when she took off her bra - seeing her breasts was almost too much for him to continue holding his climax back. Wells swung her leg over him, inverting herself on top of him in the sixty-nine position, where she resumed her performance on him, and he began thrusting his tongue into her tight, pink slit. It was a good thing that the Captain's mouth was so full, lest they be heard - or worse, discovered - by the charge of quarters outside. Instead, her moans were muffled by meat, her sultry sounds rippling down the length of Mack's pulsating dong while he dug as deep as he could into her folds with his short tongue. In the battle of the tongues, the Captain came out on top. Her long, rough, vulpine tongue snaked around his cock, dragging along it with every bob of her head.

Mack was within seconds of ejaculating when she pulled her muzzle off of his dick. He pulled his face out of Wells' undercarriage, his tongue and jaw sore, his breathing erratic. Wells got up, turned around, and squatted down over his spurting cock, holding it upright and lining it up with her entrance. The fossa clenched every muscle in his body, his teeth gritted, and his gaze cast to the ceiling once he felt that tight, hot pussy begin to swallow his dick. Knees on the floor now, she started to bounce those curvaceous hips up and down, drawing his cock out and slamming her heavy form back down onto it. He could feel her growing wetter and wetter with every bounce, and he matched her rhythm, bucking his hips and digging his claws into the short-pile carpet.

His hip flexor and abdominal muscles were on fire. Wells looked as though her thighs and calves were getting sore as well, so they decided to change positions. Mack was to take her from behind, or so he assumed when she got on all fours, presenting her ass to him again just like before. Teasing her, he rubbed his tip up and down in her slit, which caused her to bite down on her fist to keep from alerting the CQ with an animalistic cry. Finally, he pushed it inside her, mounting her from behind and bucking his hips fast, hard, and with reckless abandon. Their breathing was bated. Their bodies clapped together softly as his hips slammed into her curvy butt every time he slammed his dick into her tight snatch. Blue-hued balls slapped against her wet clit on every pump, and only a few more later, Wells came with the kind of force that Mack could only take as a compliment.

Mack could feel his cock pulsating inside her, and he knew he wasn't going to be able to hold on much longer. He slid his hands along her sides and underneath her to cup her breasts, squeezing and bouncing them to his heart's content while he fought back his climax for as long as he could. Finally, he had to pull out. Captain Wells took the hint and spun around on her haunches, grabbing her tits and squeezing them together, pushing her cleavage up towards him as he stood up. Panting hard, he grabbed his cock by the base and began stroking it as fast and as hard as he could manage, eventually grunting softly as he came; no less than seven thick, sticky ropes of cum spurting out of his tip and splashing across her breasts, covering them in his hot, creamy seed.

Short of breath, he collapsed into a nearby chair, slumped ungraciously in it while the Captain reached for the box of tissues on her desk, pulling several out and using them to wipe herself off. Mack took the box from her and cleaned up as well, grabbing his shirt and uniform top.

"They should...make that part of...the PFT..." He said, once he'd caught his breath.

"Shut up, Stewart."

***

Captain Brunson checked his watch while he stood in line at the PX. All the checkers there and he had to pick the slowest one. Finally, he bought his protein shake and candy bar and headed outside to return to the Company. He wasn't looking forward to it - some soldier had filed a sexual harassment complaint against another soldier, and now it meant a whole lot of paperwork for him, and briefings on the subject for everyone.

The jackal was almost to his car when he passed none other than Captain Wells herself. He thanked the sunglasses that shielded his wandering eyes, and greeted her with an affable handshake.

"Captain Wells. How's that new soldier working out for you?"

"Brunson, I think I've finally broken him of his gambling addiction. I believe the program might be a moot point at this time."

"Oh yeah? How'd you do that?"

Wells went quiet. She took a few steps closer in order to be heard quietly, even though there was no one else in the parking lot within earshot.

"I made a bet with him. I got him for twenty-five hundred dollars. I don't think Private Stewart will be doing any more gambling from here on out."

"Jesus, Wells! What did you bet him?"

"It wasn't my bet! It was his. Get this - he bet me that I had hemorrhoids. Can you believe that? Hemorrhoids! Wagered twenty-five hundred on it."

"Shit. Wait..." Brunson's brow crumpled, "How did that go?"

"What do you mean?"

"I mean how were the two of you able to verify that? Did you go to a medic?"

Wells bit her lip, looking like the cat that ate the canary.

"Can you keep a secret, Jordan?"

"I-I guess?"

"Well, I let him...I let him basically...poke me in the ass." She said, almost in disbelief herself.

"Wha...what? You mean like...like with his..." Brunson, in shock, could only point in the general direction of his crotch to suggest what he could not get his mouth to say. Sheepishly, she shrugged and nodded, a stupid grin plastered across her muzzle. She was still a little giddy from getting laid for the first time in a few months.

"Yeah."

"Son of a bitch!" Brunson shrieked, throwing his drink down to the pavement where it burst open in a spray of banana cream-flavored protein shake. Cursing, shouting, screaming, and kicking, the jackal grabbed his cover and threw it down, kicked it across the parking lot and tore at his hair in frustration.

"What, what's the matter?"

"Before we shipped him out, that little son of a bitch bet me five thousand dollars he could fuck you in the ass within a day of being there!"

~FIN~