tagAnalThe Prize

The Prize


I held my breath and closed one eye as I slowly drew my arm back, feeling the smooth wood gliding easily over my hand. Keeping my vision intently locked, the pool cue shot forward, striking the white ball sending it rolling across the table.

"Come on!" I muttered to myself as the cue ball just nicked the 8-ball sending it rolling towards the corner pocket.

The room went silent as the black ball butted against both sides of the pocket before coming to rest precariously on the edge of the green felt.

"Damn," I stated plainly, letting the pool cue slide through my hands, bouncing off the hardwood floor.

"Oooh, tough break buddy!" Will said with a laugh before taking a long swig from his beer.

"Oh yeah, laugh it up!" I responded, taking a seat on one the tall wooden stools lining the wall of the room. "Your the one with two balls still on the table."

"Ha! Not for long." he said in a cocky tone as he eyed up his next shot.

As Will inspected the placement of the balls on the pool table, I looked over at my girlfriend April, who was sitting quietly on one of the stools sipping her beer. I was sure she was bored out of her mind and all I wanted to do was hurry up and finish off Will so I could get my money and take her home.

"Are you okay?" I asked, placing a concerned hand on her knee.

April nodded before taking another drink of her beer.

"I'm sorry this is taking so long," I continued. "We'll be done in a minute and then we can go."

"It's okay," she assured me, in a soft, shy voice. "I don't mind."

I smiled and leaned over to give her a quick peck on the lips before turning my attention back to the game.

"Seven in the side, three in the opposite side, and then a bank off the end with the eight in the corner pocket."

"Are you kidding me?" I scoffed, laughing at Will's ridiculous call. "That's impossible!"

"Oh it's possible", he said confidently, finishing off his beer.

"Whatever man," I countered, waving my hand in dismissal. "Go for it."

"In fact.." he continued. "I'm even willing to throw down another hundred on it."

"I think you've had one too many," I said, shaking my head and motioning to the side where a fair number of empty beer bottles had collected.

"What's the matter? Will asked, poking me with the butt end of his cue. "Scared?"

"I just don't want you to lose any more money than you already have. And besides...All the money I brought is already sitting on the table."

I motioned to the large stack of bills sitting on the edge of the pool table.

Will looked at the money, biting his lip in contemplation.

"I'll tell you what," he said after a moment of thought. "I'll put in another hundred and you can throw something else into the pot."

"Like what?" I asked skeptically.

Will didn't say a word, but instead glanced over to the side of the room where April was sitting. It took me a moment to realize what he was insinuating, but I was shocked at his unspoken request.

"No fucking way!" I blurted out. "I am not wagering my girlfriend on a game of pool!"

"Why not?" Will said raising his arms into the air. "You said I have no chance of winning anyways!"

I glanced over at April, who appeared to be just as shocked as I was.

"Come on!" Will pressed, turning his attention to my girlfriend. "You don't mind do you sweetheart? Damon can take you out for a nice fancy dinner with all the money he'll win."

"Umm, I don't think so," she replied, continuing to sip nervously on her beer.

I then watched as Will took out a hundred dollar bill and laid it down on the table. I eyed the stack of bills and began to ponder the implications if such a bet was to be made.

"Are you guys sure?" He asked. "Last chance."

I turned to my girlfriend.

"You know," I began. "The chances of him winning are pretty slim."

April's eyes widened with amazement.

"You want to do it?" she spat. "You want to bet me?"

"There's no danger of losing," I reasoned. "We're already going to win two hundred and fifty bucks. We might as well collect another hundred."

"And what if you lose!?"

"I won't lose! I promise!"

I was surprised at myself. I never thought in a million years I would be trying to convince my girlfriend to let me bet her on a pool game.

"Fine!" she snapped, crossing her arms in an angry pout. "Just get it over with."

"So do we have a deal?" Will asked, beaming with optimism.

I looked at April one more time, giving her a reassuring glance before I answered.

"Yes," I said solemnly. "It's a deal."

"Good." he exclaimed, sauntering back over to the table to prepare for his final shot. "Although there is one more thing."

"What?" I asked, getting more than a little annoyed at Will's antics.

"I want her ass."

"What?" April and I both shouted in unison.

"You heard me," Will reiterated. "I wont touch her pussy but I want that sweet little ass of hers."

"But April doesn't even take it in the ass!"

"That's the point," he said with a smile. "I'll get to be her first."

"I don't think so man," I stated bluntly. "That's taking it a bit too far."

I could tell by the horrified expression on April's face that she thought so as well.

"Oh what's the big deal? he continued. "It's a moot point since the chances of me winning are so small anyways!"

"Okay fine, whatever!" I finally blurted out, exasperated. "Just do it!"

"Damon!" April scolded, hissing through angrily clenched teeth.

"We can bet whatever he wants babe! He wont win!"

"So it's settled then?" Will asked, hopefully.

I looked to my girlfriend for a final confirmation. She was sitting arms crossed, eyes narrowed glaring at the two of us.

"Yes," she said softly, keeping her glare fixed on me. "It's settled."

Will smiled and leaned over the table to eye up his shot. Suddenly there was so much more at stake and I could feel my heart beat faster. April also appeared to be nervous as she quickly downed the rest of her beer. Will, on the other hand, seemed perfectly calm as he began to slide the cue back and forth over his hand. I held my breath as he pulled back one final time before striking the cue ball, sending it rolling across the table.

The shimmering white ball struck dead center between two balls that were resting together in the middle of the table sending each one rolling to the side. To my surprise they both dropped into the pockets on opposite sides of the table, while the cue ball continued on its way, bouncing off the far end.

"Come on, come one!" Will muttered as the ball rolled slowly across the smooth green felt.

"Oh Fuck," I groaned quietly as the ball made its way straight towards the pocket.

It was then that the world seemed to stop and the room fell deathly quiet as the ball teetered on the edge for a split second...before falling down into the leather pouch.

I was stunned and dumbfounded, staring at the table and trying to process what had just happened. Will let out a victorious howl and jumped ecstatically into the air. I swallowed hard and dropped my head into my hands. Not only had I lost a fair amount of money, but I had also lost my girlfriend to Will's perverted pleasures.

"Damon!" April screeched, glaring at me with daggers in her eyes. "You said you couldn't lose!"

"Fuck!" I cursed, throwing my pool cue to the ground. "It was impossible! I can't fucking believe it!"

"Oh, I can," Will said beaming with enthusiasm. "And I can't wait to collect my prize!"

"Fuck that!" I countered. "I'll just pay you the money when I get it."

"Oh no, no, no," he scolded, shaking his head. "We made a deal. Everyone agreed, including your sweet little April. I put a lot of money on the line and now I want what's owed."

My girlfriend's face was contorted in a look of absolute horror as Will strolled towards her.

"Come on man," I pleaded. "I'll pay you double what you bet. She's not ready for that."

"She's not ready? he asked, shooting me a devious glare. "Or you're not ready?"

My fist clenched in anger as he threw an arm around April, pulling her tightly to him. Her arms were crossed firmly across her chest like they often are in uncomfortable situations. And this was definitely an uncomfortable situation.

"Don't worry," Will said, assuringly. "I'll be gentle."

I knew then that there would be no way of getting out. When Will set his mind to something, he always followed through, and I knew he had been eyeing April for a while. I cast my girlfriend an apologetic look as my heart sank with resignment.

"Damon," she said, her voice softening. "You're not going to actually let this happen are you?"

I just shrugged my shoulders and tried to keep my eyes away from Will's pretentious grin.

"Sorry babe," I said with genuine concern. "I don't know what else to do. He won fair and square."

It looked as though April was about to cry although I could tell she was trying very hard not to. Her lip was quivering and she was fidgeting nervously as Will hugged her with mock concern.

"So are you two love bird's done yet?" Will asked unsympathetically. "Because the sooner you get finished with this little scene, the sooner I can get into this sweet little ass."

With that, he reached down and gave her ass a sensual squeeze causing my blood to boil with resentment. April shifted uncomfortably and took a step away.

"Now?" I asked with surprise. "You want to do it now?"

"Why not?" Will asked, with a shrug of his shoulders. "Now's as good a time as any."

I looked to April, who was also more than a little put off by Will's eagerness.

"What do you say sweet cheeks?" he asked with smile. "Should we get this show on the road?"

My girlfriend cast me one last look before answering.

"Fine," she replied quietly. "Let's just get it over with."

"Alright!" Will exclaimed, clapping his hands. "I'll be right back. I just need to run upstairs and grab something. Don't go anywhere."

With that, he took off up the stairs, leaving me and April alone in the large room. As soon as he left I could feel the tension.

"April..I'm..." I began to say, reaching out to touch her arm.

"Don't!" she snapped, cutting me off and slapping away my hand. "I can't believe you did this!"

"I'm sorry!" I pleaded. "What do you want me to do?"

A few seconds passed and April's look of scorn soon turned softened into one of sadness.

"Damon?" she asked. "Are you still going to want to be with me after this?"

"Of course," I answered quickly. "Why would you ask that?"

"I'm just afraid that you'll see me as a slut or something."

"Don't worry," I assured, leaning in to giver a soft kiss. "Nothing will change. I promise."

April then threw her arms around me and kissed me back, holding me tightly for a long while as a thousand thoughts swam threw my head. How would I feel after it happens? Would I be able to look at her the same way? I quickly dismissed all thoughts and turned my attention back to the girl in my arms.

She was quite beautiful and I felt extremely lucky to be with her. In fact, she was everything I looked for in a girl. She had shimmering dirty blonde hair which contrasted perfectly with her well tanned skin. Her face was gorgeous, possessing a quiet confidence that went well with her shy demeanor. Her five foot three frame was, at then moment, perfectly fitted into a white low cut top and a tight pair of black capri pants which she always preferred to wear. Nobody else seemed to mind either, as they always exemplified her cute little round ass.

After a minute long embrace April released her grip on me and walked over to the fridge.

"What are you doing?" I asked.

"I think if this is going to happen..." she replied. "I'm going to need another drink."

April drank fast and was already sucking the last drops from her beer bottle when Will returned.

"Found it!" he said cheerfully, holding up a bottle of lubricant. "Haven't used this stuff in a while."

I just nodded, not feeling up for any kind of conversation at that point.

"So I think we should set some ground rules," April suggested as Will checked the expiry date on the lube. "Just to avoid any...unwanted incidents."

"Don't worry," Will said, with a nonchalant wave of his arm. "I'n not going to try anything weird. Just step up the table and we'll get started."

I couldn't imagine what April was thinking about just then as Will took her hand and led her over to the pool table. That last beer had calmed her nerves a bit but I could tell she was still more than a little uncomfortable with the prospect of losing her anal virginity. Trembling like a leaf, she rested her hands gingerly on the green felt as Will came up behind her, towering over her small frame.

"Let's get those pants off," he coaxed, reaching down to run his hands over her ass.

April swallowed hard, and turned to give me one final sorrowful glance before reaching down and unbuttoning her fly. Will was standing extremely close to her gazing downwards with a look of pure lust. As her zipper descended, he smiled and extended his hands to help her wrestle her tight pants down over her hips.

"Mmmm," he moaned approvingly as April's pants slid down her smooth legs to come to rest on the floor around her ankles, leaving her standing in only a pair of little white cotton panties.

I took a seat, feeling a strange tingling sensation in my stomach. My heart was racing, and to my surprise, my dick was hard as a rock. I took a deep breath and continued to watch the scene unfold before me.

Will placed a hand on April's back, gently prompting her to bend over. Fully compliant, she slid her hands across the felt table coming to rest, completely bent over and waiting nervously. At that moment I could not explain the feelings I was experiencing. I was stuck somewhere between arousal and jealousy and It was driving me crazy!

"Damn girl," Will exclaimed, groping my girlfriend's ass though her panties. "I can't wait to sample a piece of this!"

"Well then hurry up then!" April scolded, clenching her teeth with impatience.

Will just laughed and continued to take his time, savoring every moment. I shifted in my seat, reaching down to adjust me dick which was straining uncomfortably against my pants. Silently, I scolded myself for getting turned on by seeing my girlfriend in a such a state of vulnerability while another guy prepared to have his way with her.

Slowly and deliberately, Will began to slide April's little white panties down her smooth, supple ass. Her body was rigid with tension as she was finally fully exposed as she stood, bent over the pool table. I could hear her groan with apprehensiveness and bury her face in her arms as she tried to hide from the embarrassing situation. Her uncomfortableness only made Will happier and he grinned from ear to ear as he pulled her underwear down around her knees.

"Oh yeah," he muttered quietly, placing both hands on her naked flesh and feeling the firmness of her ass.

April stiffened at his touch, cringing as she felt his hands on her bare, naked flesh. I was on edge as well, my foot tapping nervously as Will peered down at my exposed girlfriend with eyes full of lust.

"Come on honey," he urged, reaching down to unzip his pants. "Spread that ass for me."

April lifted her head from her arms and glanced back at him over her shoulder with a look of pure distaste.

"I'm not doing that," she scowled.

"Just do it," Will ordered, a little more sternly.

At first it looked at though April was going to continue to protest, but her scowling visage soon softened into a blank submissive stare as she shamefully reached back with both hands, gripping the smooth skin of her ass cheeks. I found myself leaning over in my chair to get a better look as she gently peeled back her fleshy cheeks, fully exposing herself to Will's hungry eyes.

"Mmmm," he moaned in satisfaction as he fumbled with his belt, his eyes now glued to April's perfect pink asshole. "That's it baby. A little wider."

April closed her eyes as if trying to block out the whole situation as she obeyed submissively and pried her ass open even wider. The whole scene looked so dirty, I could feel my cock straining against the fabric of my pants. Indiscreetly, I reached down and adjusted myself, pulling my swollen erection to one side of my pants, allowing some relief as I continued to watch. Will's belt made a loud 'clink' sound as it hit the floor along with his pants, which he promptly kicked to the side. He then pulled off his underwear, all the while keeping his eyes fixed on my girlfriend's lewdly spread ass.

"Damn, Damon," he exclaimed as he squirted some of the lubricant into the palm of his hand. "Your girl has the most perfect little asshole I've ever seen. I can't believe you've never fucked this thing. If she was mine I'd have my cock up her ass every night!"

The truth was that I had tried numerous times but April had always refused. Now I was sitting idly by as my girlfriend was about to be anally deflowered by another guy. A wave of envy slowly crept over my body as I watched Will slather lube up and down the shaft of his hard, outstretched dick. He then reached down and spread some of the slippery fluid over April's tight little star. At first she winced at the touch of the cold substance, but soon relaxed enough to allow him to even push his thumb inside her. After a few seconds of thumb fucking her ass he pulled his digit out and took a hold of his thick, wet cock.

Staring intently, Will stepped forward and rubbed the head of his dick down April's ass crack, coming to rest at the entrance to her tiny, private hole. I noticed my girlfriend holding her breath as she braced herself for what was about to come. Will's brow furrowed with concentration as he pressed his swollen cock head against her virgin rosebud. April gripped the cheeks of her ass tightly and bit her bottom lip as her tiny pink buttthole began to stretch to accommodate Will's invading dick. His look of concentration soon turned to one of extreme pleasure as her tiny hole proceeded to slowly swallow his thick cock.

"Ugghhh," April cringed, biting her lip as she felt her virgin hole being violated for the first time.

Will smiled and placed a hand on her lower back, leaning in to feed more of his meat into my girlfriend's ass. In my position I could see perfectly as he slid further into her hole, eliciting more whimpering from April's tightly pursed mouth. Her body trembled as she let go of her ass cheeks and buried her face into her arms, muffling her painful groans.

"Fuck, you're tight!" Will exclaimed, reaching down to spread her ass cheeks, savoring the view of half of his cock firmly embedded in April's asshole.

As he continued to work his way into my girlfriend's butt, I found myself leaning in to get a better view of the vulgar scene. As I watched, Will grasped her hips and forced the rest of his dick inside her, causing her to bite her own arm to keep from crying out. His hips were now pressed firmly against her luscious ass with his cock firmly embedded inside her anus.

"Where's my dick April?" Will asked, giving her firm ass cheek a light slap. "Tell me where my dick is."

April raised her head as if confused before receiving another slap. This one was a bit harder and caused her to wince, although she offered no objection.

"Where's my dick?" he repeated.


"Tell me you like it!"

"I..I..like it," she stammered, apparently getting used to the feeling.

"Tell me you want me to fuck your ass."

The room was filled with silence as April shifted uncomfortably. Suddenly the silence was broken by another loud 'slap' as Will brought his hand down on her reddened ass once again. Slowly she turned to me, staring into my eyes as she whimpered the words.

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bydamonX© 19 comments/ 384222 views/ 187 favorites

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