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A Gentlemen’s Bet

“How about we make things interesting?” John suggested, his chapped lips pressed into a devious sneer. “I’ll give you once last chance. I’ll let you raise me to all in.” His deep voice commanded the room, drawing all eyes to him. He was a real man’s man, pushing 50 with crisp blue eyes, a thick head of gray hair, and a gut stretching the middle of his polo shirt.

I narrowed my eyes and pointed out, “But I don’t have anything else to bet.” Every dollar my wife had let me bring was already in the pot. But he had my attention, even Hank and Greg sidled back up the table to see if I could pull out the win and take home the cash John had already won off them.

John leaned back in his chair, savoring my poorly-concealed desperation, and finally said, “You know, you’ve always had a big mouth. Gossip like a girl and talk a bigger game than you ever bring.” The guys leaned in interestedly, but I was wary. He went on, “So put that mouth in the pot and we’ll settle this.”

“My mouth?” I repeated, baffled.

“If I win, I get to put your big mouth to work on my big dick,” he declared, raising his voice over Hank and Greg’s uproarious laughter.

Rolling my eyes, I said, “Don’t be an asshole. It’s seriously not funny.”

“Yeah. I’m not kidding,” John smugly declared. “Are you in or not?” The whole room went quiet until I could hear my heart pounding. I anxiously inspected my hand, a Jack high straight, and thought of the nearly $2,000 at stake. He was just fucking with me, I thought. He just wanted to rattle me and I wasn’t about to flinch first.

“You’ve got a deal,” I replied. “All-in it is.”

My eyes went wide as he pushed every dollar he’d won into the pot and said, “Let’s see ‘em then.”

I trembled as I lay my cards on the table. I tried to be confident, but my words came out in a whisper, “Jack high straight.” I almost jumped for joy when John frowned, but when our eyes met, the corners of his mouth rose into a grin as he lay down a Queen high straight.

Nobody said a word as John and I stared at each other. He drank in the sight of my crestfallen face and dominated my gaze until I lowered my eyes to the table. John broke out into a gleeful smile and said, “Looks like all’s left is for me to claim my winnings. You guys want to watch?”

Hank and Greg just looked over at me and slowly, horrifyingly smirked. I stood up on shaky legs and stammered, “Well, I should get going. Good game, guys. I had—”

Greg raised a silencing hand. He was the host, a king in his own castle, and he said, “A bet’s a bet, man. You’ve gotta settle up.”

John pushed his chair back and spread his legs, fondling the sizable bulge in his jeans. He suggested, “Why don’t you get the three of us another round of beers before you start, cocksucker?”

Hank nodded in agreement and said, “I’ll actually have a bourbon on the rocks.”

The three men stared at me expectantly until, in a daze, I glided to the bar. They grinned at each other as I poured and returned with a round of drinks. John shook his head when I raised my beer to my lips, and he said, “Now, now, you’ve got work to do so I’ll have that.” The man held out his hand until I reluctantly pressed my glass into it and was rewarded by his deep voice rumbling, “Good boy.”

“Fuck you guys,” I sighed as I sank to my knees at my best friends’ feet as they shuffled their chairs close around me. I scooted forward between John’s widespread legs and reached out toward his belt, but he grabbed my wrist in his powerful hand.

They all chuckled as he said, “Well, aren’t you eager. But I need a little more romancing than that. Why don’t you strip for us, slut?”

“Oh come on,” I protested, but quickly succumbed. I unbuttoned my shirt, slowly revealing a chest still smooth and slender as it was when I was in my twenties. Greg whistled appreciatively and rubbed his hand over his own crotch. I blushed and sighed, but discarded the shirt and went to work on my jeans. It would only get worse when they saw my briefs.

Hank snorted into his bourbon when he caught glimpse of my tight-fitting, bright red briefs, and he taunted, “Damn, I wish my wife wore panties half that nice.” The others murmured in agreement but I just kept my eyes down as I peeled off my jeans.

Stripped down to my briefs, I looked up at John’s mocking face as he slowly shook his head and commanded, “Lose the panties.” I wanted to run, to storm out, but the sternness of the man’s voice as he stared down at me broke my resistance. I pulled my briefs down my legs and threw them aside, finally kneeling naked between my three best friends with my diminutive manhood on display. John smiled with a strange sort of warmth and said, “Perfect.”

It wasn’t the first time any of us had seen each other naked, but it was far different. I was reduced. The three men seemed to swell and tower over me as I became less than. I should have felt humiliated, but mostly I just felt eager. When John nodded his approval and allowed me to unbuckle his belt, I felt a shameful flood of excitement.

His body was warm beneath my fingertips as I struggle to unbutton his jeans and unzip his fly. He lifted himself to let me slide them down around his ankles and reveal a pair of flannel boxers bulging with the John’s still soft and much renowned cock. The wives remarked about it on occasion, in their sideways fashion. We’d all seen it, but only soft. Even so it hung about half a foot down his thigh and I found myself wondering just how much the thing could grow.

I fished him through the fly of his boxers as he gulped down the last drops of my beer and grinned at our buddies. I could feel their hot breath on my shoulders as they leaned in to watch. John’s cock gushed the sweaty, pheromone-rich smell of a long day into my nostrils. I winced at the stench, but my mouth watered nonetheless. His icy eyes met mine as he grabbed his big floppy dick in one hand and the back of my head in the other.

The meaty mushroom at the tip of his shaft squished against my closed lips, smearing them with a sheen of the man’s precum. “Open up, princess,” John demanded.

“Fuck—” I started to say, but he shoved himself inside me and let me feel the immense heft of his manhood depressing my tongue. He pulled me close, burying my nose in his pungent boxers and letting his still-soft cock tickle my throat.

John let out a moan and he grunted, “Damn, his mouth was made for this.”

“It feels good?” Greg asked in a strained, eager voice.

“Like a pussy on his face,” John chuckled. “Those big, full lips are squeezing me and damn… that tongue.” I hadn’t realized what I was doing, but he was right. My lips were massaging the base of his shaft as my tongue teased along its massive underbelly, and with every moment I felt his flesh stiffen and swell. His floppy cock reached down into my throat just before it began to firm up. As he thickened, he stretched me open around him and held my head in his lap. “Fuck. I’m going to bust the biggest nut down his throat.”

“Fuck yeah,” Hank muttered close to my ear, “is it weird that I’m getting hard just watching this?”

“You’re not the only one,” Greg admitted with a laugh. “He looks like a little bitch on his knees like that, doesn’t he?” He put a hand on my back and pushed me harder into John’s crotch as I gagged, sputtering up spit that just lubed his cock. John started fucking my face, holding my head in both hands and using me like a fleshlight.

“He’s actually got a nice ass too,” Hank whispered, grabbing a fistful of my cheek and rubbing a thick finger against my virgin hole. “You ever fuck a girl in the ass?”

John let out a pleasurable sigh before he said, “Jess let me one time, but she barely lasted five minutes before she made me stop.”

Greg laughed and said, “Well, yeah, you’re hung like a fucking moose. I actually spent my whole freshman year fucking my roommate since it beat jerking off when I got horny.”

“Damn,” Hank exclaimed, “that’s a good point. I’ve always wondered what it felt like, but Beth would never go for it.”

John ruffled my hair and said, “I bet this bitch wouldn’t mind having her pussy popped open. What do you think, slut?”

For the first time in almost five minutes, he let me pull my lips up off his cock. Looking down, the enormity of the man finally sunk in as I watched almost nine inches of flesh slide out of me like a perverted magic trick, leaving my throat with a foreign feeling of longing emptiness. I sputtered and protested, “Guys, I’ve never done anything like that. I don’t know about—”

Hank had pulled over an ottoman and Greg grabbed me by the hips and lifted me up off the ground, burying my face against John’s thigh. Hank slid the ottoman under my chest so I was bent over it with my knees hanging just off the ground. He hurriedly came behind me, kicking my feet to the side as he kneeled and hugged his body over mine. He ran his fingers over my ass as he whispered, “Come on, baby. We all see the way you’re slobbering on John. We always wondered about you, and now the secret’s out. It’s gonna feel good. I promise.”

I let out a little moan when Hank rubbed his bulging jeans against my bare ass, and the guys all grinned. John declared, “Sounds like someone’s horny for more cock, Hank. Why don’t you indulge him?” John grabbed me and shoved his dripping wet manhood back down my throat, and I heard the telltale sound of unzipping jeans just before Hank rubbed his slick, hard cock against my clenched hole.

“It helps if you eat him out, especially if he’s a virgin,” Greg offered.

Hank scoffed, “Man, isn’t that a little gross?”

“Naw, man. It’s fucking fun. Here, let me get him ready for you,” Greg said as he pushed him out of the way and knelt behind me. His thick scruff scraped against my smooth cheeks just before he ran his tongue over my hole. Despite myself, I moaned around John’s cock and it just egged the men on. I clenched my fingers into John’s thighs as Greg bashed his tongue against me, battering at the door eager to slide into me. “His pussy tastes fucking great,” he mumbled into me.

In the same moment, John pushed back down my throat and Greg’s tongue breached my unyielding ass. I trembled with the flood of sensation as my friend stretched me open.

“Oh fuck,” John growled through clenched teeth, “he’s milking the shit out of me. I’m gonna cum.” His words didn’t fill me with anger, disgust, or even relief. Instead, my skin tingled with anticipation as I felt his shaft pulse against my lips. A rush of cum flooded into my throat, and when his hand went limp, I pulled back, not out of a desire to escape but an urge to soak my tongue and coat my mouth with the man’s hot, thick seed.

He fed me mouthfuls of the ropy white goop, leaning back in his chair with occasional spasms of pleasure as his potent cock pumped out a fresh burst. All three of the men bellowed taunts and jeers, but I was deaf to everything but the flood filling my stomach. I didn’t even notice when it ended, when I was uselessly suckling at a dry shaft, until John ran his fingers through my hair and pulled my lips close until they were tight around the base of his softening member.

“Is his ass ready?” Hank’s eager voice broke my trance. I suddenly noticed the fullness of Greg’s tongue inside me when he pulled it out and made way. Hank grabbed my hips and used that leverage to power a merciless thrust that sent his cock blowing past my loosened hole into the depths of my virgin tunnel.

I howled around John’s flesh, squirming against the men until Greg mounted me, sitting astride my back to pin me to the ground. My hands scrambled until John grabbed me by the wrists and pressed them to his thighs. I was utterly helpless to Hank’s primal rutting inside me.

“Definitely a virgin,” Greg chuckled as he lay his rigid cock across my back. Hank bottomed out inside me and bucked up against the heavy man atop me, but Greg just let his weight sink down as he smacked his manhood against my soft skin. He snorted, “He’s a good ride though. Nice and spirited.”

John laughed, “He’ll be broken by the time the night’s over.”

“I’ve never fucked a hole like this,” Hank said. “His ass keeps trying to push me out, but it just feels like fucking heaven on my dick.”

“Damn,” John muttered, “I’ll have to try that next time.”

“Right?” Greg agreed. “He’s definitely gonna be our poker pussyboy from now on. Aren’t you, girl?” He patted me on the head. “Kneeling under the table while the men play.”

“Oh man, that’s weirdly hot,” Hank rasped. “I think I’m gonna cum.” His heavy hips slammed into my butt hard enough to leave a bruise, never resting for long.

Greg whipped his cock against my back between strokes and his voice was strained when he said, “I’ll try to finish at the same time.” Hank’s guttural groan came quickly, and Greg echoed it a few seconds later. John humped his soft cock back into my throat and the constant smell of his crotch was blocked from my nose. Hank’s nuts slapped against my ass one last time before his manhood started filling my virgin hole with his breeding juice. A long rope of cum burst from Greg, trailing from the back of my head halfway down my back, and it was followed by many more until warm goo coated my shoulders and neck.

All the while, I could do nothing but wiggle underneath the three men as my rigid little dick spilled its bounty on the ottoman. I wanted to rage, to fight back, but the notion felt so far away at that point. A quiet, but growing, part of me wanted more. It liked this feeling, this humiliation and disempowerment. There’s a peace of mind in submission, and it was proving intoxicating.

It was many minutes before my best friends untangled from my cum-filled and drenched body, standing with flaccid cocks hanging out of their jeans and going on as if nothing just happened. When I slowly rose, Greg’s load traveled down my back in thick rivulets. Hank’s dripped from my stretched hole. John’s settled in my stomach and what was left outside me already dried on my face.

The three regarded me with lascivious grins, no longer seeing me as the fourth amigo, but instead as a dominated bitch to be used. It was a strange feeling, to be finally seen for the person I’ve always known myself to be.

John grunted, “You look like you could use that drink.”

“Yeah,” I said in a small voice with an exhausted smile. “That was pretty intense.”

“Sure thing. I’m just about done with it,” he boomed and lowered his bottle mouth to the tip of his cock. I watched, transfixed, as his stream began to flow, rapidly recycling the beer back into its bottle. Hank and Greg grabbed empties and began brewing their own drinks for me. John just grinned at my forlorn expression until his piss overflowed from the bottle and puddled on the floor in front of him.

John offered the bottle to me but I just shook my head. He laughed and said, “Your choice, but I sure got plenty of pictures of you with my big dick down your throat. Wouldn’t it be a shame if those got around?” I stared down at the offered bottle and hesitantly accepted it. John insisted, “Now let’s see you gulp this one down. We were nice enough to brew you up something and now we want to see you enjoy it.”

I pressed the bottle to my lips, tasting the man’s potent piss on the rim. I paused, and John pressed his fingertips to the bottle and slowly tipped it toward my mouth. The flavor filled my mouth, making me cough and sputter as I struggled to shotgun the warm, bitter drink. They all grinned and laugh, savoring the sight of my ultimate emasculation. I choked on the last gulp.

“Nice job, pussyboy,” Greg praised, patting me on the shoulder as he pressed his bottle into my other hand. “Now drink up. And don’t forget to lick up everything John spilled. Only polite to leave my house clean as you found it.”

Warm bottle against my palm. Perverse grins on my friends’ faces. Seed swishing around my insides. It was all so wrong, but it felt so right, and the only protest I managed to muster was a meekly whispered, “Yes, sir.”

I’d lost the bet, but in truth, I hadn’t put up anything I wasn’t willing to lose.

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