The Prize_(1) by damonx

Rating: 91%, Read 49558 times, Posted Jan 24, 2010

Fiction | Anal, Reluctance

The Prize

By: DamonX ([email protected])

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


"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.


"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


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


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


"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


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


"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


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


"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


"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


"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


"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


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


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


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


"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


"Where's my dick?" he repeated.


"Tell me you like it!"

" 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.

"I..want you to..fuck my ass."

April's words cut me like an knife as she stared apologetically into my

eyes. My dick, however, was harder than ever and i knew that if I so

much as touched it I would cream in my pants. Will seemingly enjoyed

her forced response as well, since a ecstatic grin spread across his

face upon hearing those words. As he began to withdraw his cock, April

tossed her head back, sending her dirty blonde hair splashing across

her smooth tanned back. I could hear her labored breathing as Will

wriggled his dick back and forth inside her ass before pushing back in

with one smooth stroke.

"Fuck!" she gasped as she felt his balls slap up against her pussy lips.

Will smiled before pulling his dick out again, only to slam it back into

April's tight little hole. With every thrust, her small body lurched

forward and a quiet groan escaped her lips. Will was picking up the

pace, driving his cock in and out of my girlfriend's ass as her hands

clawed at the green felt in futility. Her body was trembling as he

moved in and out of her, reaching down to spread her cheeks wider,

giving himself a perfect view of his cock planted deep in her ass.

"Mmmm," he moaned, withdrawing his dick until only the head remained

tightly trapped within the confines of April's tight little ring.

"Your asshole looks so good with my cock inside it."

Will then began to push his dick back inside my girlfriend's ass, as she

squealed in response. I couldn't tell if she was starting to enjoy

herself or if the sounds coming from her mouth were the result of the

pain of having a cock shoved into her ass for the first time.

"That's it baby," he groaned, giving her ass another light slap. "Moan

for me. Show me how much you like it."

April let out a long, drawn out moan as Will began to pick the pace once

again. His breathing was becoming more and more erratic and I could see

beads of sweat forming on his forehead. I could tell he was close to

cumming and I began to wonder where he was going to do it.

"Ugh. Ugh. Ugh," April's voice resonated as her ass repeatedly swallowed

up Will's cock.

"Oh fuck yeah!" he shouted out as every muscle in his body tensed. "I'm


He then let out a strange, unnatural sound as he dug his fingers into

April's ass, apparently coating the inside of my girlfriend's asshole

with his cum. April closed her eyes and opened her mouth as if to cry

out, but no sound was produced. She just shuddered and gasped as Will's

orgasm subsided and he gave her a couple more soft thrusts before

slowly pulling his cock from her tightly clenched anus.

As his dick slipped free with a wet slurping sound, I noticed a small

rivulet of cum trickle out of her ravaged hole. His face was glowing

with intense pride and satisfaction as he stepped back to pull up his

pants. April remained in her exposed position for a few moments before

she finally realized that the ordeal had ended. With a look of

embarrassment and shame she quickly pulled up her pants and headed for

the bathroom. I was about to say something to her, but just couldn't

get it together as she slammed the door behind her. I was astounded.

Another guy had just cum in my girlfriend's ass!

"Thanks man," Will said with a relieved sigh as he slapped me on the

back. "I needed that."

I didn't know whether to be mad or not as I remained sitting in my seat,

my dick still engorged from the "show" I had just witnessed.

Tensions were high as April returned from the bathroom and we prepared

to leave. She didn't say a word as she quickly gathered up her

belongings and headed up the stairs. I followed close behind her as we

made our way to the car.

The ride home was no less tense with April sitting silently and staring

vacantly as I drove her to her apartment. I tried to make conversation

but she was having none of it. I therefore resigned myself to being in

her bad books for the foreseeable future, and didn't even bother to

attempt any more verbal exchange. As I pulled up to her building,

April quickly got out, slamming the door behind her. I sat there for a

moment as she walked up to the front doors and entered without so much

as a glance back. I exhaled an exasperated sigh and sank further down

into my seat, wondering how I was going to make it up to her.

* * * *

The next day was torture. All I could think about was April getting

fucked and I couldn't get the picture out of my head. I thought about

the expression on her face and the way her ravaged asshole looked with

Will's cum dribbling out of it. I felt extremely guilty that I had

put my girlfriend through such an ordeal and even more guilty at the

fact that it turned me on so much. When I got off work I decided that I

would surprise her with flowers and take her out to dinner.

I hurried home and showered before setting out, stopping off to pick up

the flowers. As I pulled up to April's place I decided to climb up the

fire escape and surprise her. She always appreciated surprises

although I could only hope my small effort was enough to make her

forget about the events of the previous day.

I parked my car and made my way around the back of the building silently

hoping April's mood had improved. Luckily someone had left the ladder

down so I quickly bolted up and soon found myself outside my

girlfriend's bedroom window. The curtains were drawn, although there

was a small space between the curtain and the edge of the window that

allowed me to see inside. Cautiously I peered through the window,

dropping the flowers and my jaw in utter surprise.

There was my girlfriend on her bed, positioned on her hands and knees

completely naked! Her head was buried in her pillow and her fingers

were hard at work between her legs. I peered closer and noticed that

while one hand worked feverishly at her clit she also had a couple

fingers buried deep in her pussy. I was utterly shocked. I knew most

girls masturbated but I certainly wasn't expecting to find April in

this way. At first I considered knocking, but soon dismissed the idea,

becoming increasingly aroused by the site before me.

As I reached down to adjust my growing dick in my pants, April did

something that really surprised me. Removing the two wet fingers from

her pussy, she reached around and began to massage her own asshole,

rubbing it with slow deliberate movements. If my jaw was not already

agape with surprise it would certainly have dropped open at that site.

My cock was pulsing as I continued to play the voyeur, watching

intently as my girlfriend pleasured herself with her nimble fingers.

Absent-mindedly, my hand dropped and grabbed at my straining dick just

as April began to slip her slender finger into her tight little ass. I

pressed my face to the glass in order to get a better view and licked

my lips at the site of her finger fucking her tiny butthole. Then

suddenly, I stumbled forward and slammed my face into the glass,

dropping the flowers in an attempt to break my fall. April gave a

startled shriek and jumped up from her bed in surprise, grasping for

her bath robe as her face contorted with a mixture of shock and fear.

"Uh oh," I muttered, rubbing my head as April's expression morphed from

fear to anger.

"Damon!?" she yelled, wrapping the robe around her naked body. "Is that


As she stormed towards the window I tried in vain to think up a story

that would fit the situation but none came to mind. Instead I just

froze and waited as April threw the window open.

"What the hell are you doing?" she yelled. "Are you spying on me?"

"No, no, no" I stammered. "I was just...bringing you flowers. I was

trying to surprise you."

"Well you certainly did that! You scared me to death!"

"Sorry," I replied sheepishly, hoping that my cute expression would

soften her anger.

"Just get in," she said plainly, turning and walking back across the


Awkwardly, I crawled through the window and fell onto the floor in a


"So," I began, standing up and brushing myself off. "Sorry to


April cast me an angry glare that silenced me and prevented me from


"I don't want to talk about that," she stated coldly. "In fact, I never

want you to mention that again."

"Oh come on," I said, walking up and wrapping my arm around her. "It was

hot. I had no idea you ..."

"Damon!" she snapped, cutting me off. "I said I didn't want to talk

about it."

I resisted the urge to speak again and stepped back to give April a

little space. I then watched as her expression softened and her eyes

traveled from the floor up to meet mine.

"So..." she said finally. "You liked what you saw?"

"Fuck yes!" I blurted out, my mouth curling into a broad smile. "That

was the sexiest thing I've ever seen."

My girlfriend returned my smile, but still seemed a bit reserved and

apprehensive. Slowly, she stepped towards me.

"And it turned you on?"

I nodded.

April sheepishly ran her hand along my stomach, biting her lip with mild


"Are you still turned on?" she asked.

I just smiled and moved her hand down to the bulge in my pants.

"What do you think?"

A brief moment passed before we stepped closer and kissed. It wasn't

the slow sensual kissing that April usually enjoyed, but rather a more

excited, lustful kissing as we plunged our tongues into each others'

mouths. I pulled her close, reaching around to grope her ass as she

moaned into my mouth and ground her pelvis into mine.

"I want you. Now!" I stated firmly, tearing open her bath robe and

sending it falling from her shoulders to the floor.

April stumbled backwards to the bed, scurrying onto the soft mattress as

I followed in pursuit, crawling towards her naked body. After removing

my shirt, I began to work at my pants while she sat back smiling and

spreading her legs. I licked my lips hungrily at the site and had my

face buried between her thighs before my pants were even off. As I

licked and sucked at her velvety folds, I kicked my pants off

awkwardly, freeing my cock from its former confines.

Kissing my way up April's tanned body, I soon reached her face which

brought my turgid dick in line with her soft, wet pussy. With one

forceful plunge, I sunk the entire length of my cock inside her,

eliciting a startled gasp as she tossed her head back in a mixture of

pain and pleasure.

"Oh yesssss," she purred, closing her eyes and wrapping her legs tightly

around my back.

April's hot little hole gripped my dick as I began to slide it in and

out, my hips rising and falling in a controlled, rhythmical movement. I

could actually feel her pussy getting wetter with every thrust.

"So," I said between breaths. "Do you always finger your ass when you

play with yourself?"

Her expression froze for an instant but soon resumed its former look of

sensuality as she answered.

"Only since yesterday."

"Oh really?" I stated, driving my dick hard into her writhing body.

"Does it have anything to do with what happened with Will?"

April bit her lip and nodded.

"I thought you didn't like that whole ordeal?" I asked, a little

confused at my girl's apparent change of attitude about the previous

day's activities. "You seemed pretty upset."

"I was at first, but...."

April was cut off as I plunged my cock into her a little harder.

"Go on," I urged, slowing my thrusting and allowing her to continue.

"Well, at first it felt so degrading and dirty, but after I got home I

began to think about it kind of turned me on."

"Really? What turned you on about it?"

"I'm...I'm not sure. I think I just liked the idea of being used. Of

being treated like a sex object. And it turned me on even more because

you had been there watching me."

"Oh yeah?" I moaned. "You like me watching you get fucked?"


"You like me watching you get used?"


"You like me watching you with a dick in your ass?"

"Fuck yes!!"

I had to stop to keep from emptying my balls into April's hungry pussy,

and nestled down with my cock buried inside her. She took a deep breath

and ran her fingernails down my shoulders as she pushed her hips back

up into me as if to prompt me to continue.

"Can you fuck me from behind?" she asked, gazing up into my eyes with a

glassy expression. "I want you to do me like Will did."

I just smiled and pulled my dick out, kneeling back to let her change

positions. Quickly she rolled over onto her hands and knees, pushing

her hips back towards me in a sexy and enticing manor. Her face was

resting in her arms as her back arched, exaggerating the roundness of

her irresistible ass. Taking my dick in my hand, I began to run it

along her glistening pussy lips, licking my lips in anticipation before

pushing it back inside the warm confines of her tight, wet hole.

"Oh yeah," she cooed as she felt herself being filled from behind. "Fuck

me Damon. Fuck me hard!"

I took a deep breath and resumed plunging my tingling cock into her

insatiable pussy as my hips slapped violently against the back of her


"Fuck yes!" exclaimed. "Just like that! Fuck me hard and make me cum!

Make me cum and then I want you fuck my ass!"

I stopped suddenly. Those were the words I had been waiting to hear for

over a year and now that April said them, I almost lost control.

"Play with your ass," I suggested. "I want to watch while I fuck you."

My girlfriend let out a subtle giggle before reaching back and sliding

her fingers down that enticingly taboo crevasse. I quickly intercepted

her hand on route and brought her hand to my mouth, sucking two of her

fingers as she moaned with approval. I then guided her hand back to its

final destination and April began to run her wet finger around her tiny

rosebud in small, deliberate circles. I resumed fucking her, although

more slowly than before, as she slipped the finger up to the knuckle in

her tight asshole.

"Oh my god!" I gasped at the site. "That looks so fucking hot."

April tossed my a smiling glance over her shoulder as she pushed the

delicate digit in farther. I grabbed a hold of her tight ass cheeks and

splayed them wide in a lewd manor in order to give my self a better

view. In and out, her finger plunged as I matched rhythm with my

pulsing cock. As the pace quickened, I reached under her body to rub

her clit, sending her closer to climax. Suddenly she shoved her face

into the mattress to muffle a sensual scream as an intense orgasm

wracked her small body, causing her pussy and ass to twitch and pulse

in unison. April then removed her finger from her winking asshole and

took a few deep breaths as I slowly withdrew.

"Now," she began, looking back at me with a mischievous smile. "Fuck my


She arched her back even more, causing her ass to splay open as I

collected some of her cum with shaking hands to coat the shaft of my

dick. I then pointed my head at the tiny orifice and pushed forward.

April let out a restrained squeal as I pierced her anal opening with my

swollen tip, watching carefully as her tight rim began to stretch

around my invading shaft.

"Oh fuck, oh fuck, of fuck!" she blurted out absently as her asshole

swallowed more of my dick, gripping in opposition to every inch gained.

"Are you okay?" I asked with concern, stopping my intrusion.

"Yes," she answered with a gasp. "Keep going. I want to feel your whole

cock in my ass!"

She even reached back with both hands, spreading her cheeks wide to

allow my hips to press fully against her soft skin as my cock came to

pause, buried deep inside her. At that point I began to rotate my hips,

grinding my dick into her ass elicited appreciated moans from behind

April's tightly clenched teeth. I then pulled out slightly and started

to push in and out, fucking her with short, slow motions.

"Fuck yes!" she exclaimed, pushing her asshole back around my cock.

"Fuck me Damon! Fuck my ass. Use me! Use my asshole just like Will


Urged on by my girlfriend's filthy words, I began to increase the depth

of my thrusting, plunging deep into her forbidden hole and tightly

against the contracting of her muscular ring.

"Oh yeah?" I asked in confirmation. "Maybe I should offer you up as a

prize in all my bets."

"Yes!" she returned enthusiastically as my balls slapped against her

pussy lips. "I would love that!"

I spoken somewhat in jest and mainly to hear my girlfriend's response,

but hearing her now agree sent a tingle through my body.

"I want to be a prize," she continued. "I want to be treated like an

object. Just a hole to fuck!"

I was now astonished at April's newfound sluttiness, but was

increasingly curious to hear more.

"What if there is more than one guy?" I asked.

"I don't fucking care!" she blurted out, pushing her ass back against my

hips and burying my cock deep in her ass. "They can all fuck me. They

can bend me over and take turns fucking my ass!"

That was too much for me to handle. Her dirty words sent me over the

edge and I felt my balls tense with impending orgasm.

"I'm going to cum!" I managed to say before the last final thrusts.

"In my ass!" April howled out as she tossed her head. "Cum in my ass!"

No sooner had those words escaped her mouth, than my cock was filling

the inside of her tight butt hole with hot creamy fluid. She let out a

long drawn out sigh my dick pulsed inside her, painting the inside of

her anus with cum. I pulled out and dribbled the last of the slippery

semen down over her reddened asshole as it clenched and unclenched

repeatedly. April slumped down flat on her stomach and let out a

contented sigh as she reached back to tenderly touch her abused ass.

"So?" she asked glancing back at me with an adorable smile. "When's the

next game of pool?"

The End

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Rating: 91%, Read 49558 times, Posted Jan 24, 2010

Fiction | Anal, Reluctance


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