A.S.S (Anal Stretching Society)

Leon discovers his next mission on the island: work with college boys to teach them the rules of the Anal Stretching Society.

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Frat Boys & Anal Gooning 

I woke up with Nael sticking his tongue inside my anus. Instead of being unusual about it, I spread my cheeks for him to go deeper. This was a sacred ritual for the Anal Stretching Society, to let our men worship our asses, to let them lead us to perverted sodomy from the moment we wake up to the moment we sleep.

“It’s so broken…” I moaned when he spread my anal ring, a small rosebud emerged with little effort. It was hard to believe I prolapsed just from him hooking his thumbs inside me to force my anus to gape.

“Is it too sensitive?” Nael had no qualms about sucking my cum drenched prolapse, the inch long rosebud was still covered in emerging jizz from last night.

“It is, it’s even burning a bit much…” A cum fart bubbled up from my depths. He gently pushed my rosebud back inside to check on my open rectum.

“There are signs of heavy trauma. You were a good boy enduring all that ass ruination!” He let go of my hole to play with my cheeks from behind. “We will take it slow today, not a lot of ass sex for you.” Nael still fingered me. He laid against my back pressing me against the bed. “It’s going to be hard to resist you, my shortstack little anal whore… But you took the forearms and cocks of so many men!”

“You liked it? You liked watching me getting wrecked from behind?” I reached back to jerk him off.

“Every single second you cried wanting it to stop, but took it further… I adored it.” He kissed my neck while groping my pecs with his free hand. “I have more prepared for you, just not today.” Nael’s big hand spread my cheek to watch my flaming heavily swollen ruined donut hole. “I think we’re close to repurposing it.”

“Repurposing it?” I didn’t know what it meant.

“You were already in the process of turning your hole primary use to sex. We will complete it tomorrow. You have to remember that your hole’s primary function is to shit, but bottoms at the A.S.S. repurpose said function to a secondary role. Your primary use for your anus will be to drain cum and obtain sexual pleasure.” He smiled.

“I… I couldn’t agree more.”

We took our time to have some more conversations. Nael told me about one of his recent art installations and exhibitions where he selected a few gay artists who love to worship ass to show off their work. We had a date for lunch and some movie to watch at night. Even though a lot of anal sex still happened around us on the streets, we didn’t participate in it.

The next morning was the same usual routine, Nael checked up on my ass, I cleaned, we ate some and he told me I was about to go to the beach.

It was when we arrived there that I was told the truth. Six frat boys from the Reaming Frat, which was the college faction of the Anal Stretching Society, were at the beach. They were here to experience some loose holes. Taye, Gabe’s partner, was supposed to be the gangbang hole destroyed by those youngsters, but he was too tired from his activities so they decided to split the frat boys: three were supposed to gangbang me and three were going to fuck Shiro.

I wanted to meet my friends, talk to Hans and check out Shiro’s hole, but we were unfortunately directed to different areas of the beach to allow us to focus on those boys.

The tension overflowed inside me when I saw them. Most of them were either virgins or didn’t have any experience with a stretched out anus; all of them had never fisted another guy. Despite v ing quite sexy, they were still inexperienced boys.

“It’s a pleasure to meet you, boys!” Nael took the lead. “I’m Nael and this is my bottom, Leon. We’re proud anal addicts, sodomy lovers and prolapse practitioners!" There were three young teen boys and their heavy tightly packaged big dicks were way too excited in their speedos!

“I’m Bluey… I mean, my name is Mark but they call me Bluey. I'm the leader of this team.” He was an impressive looking very blond guy with light blue eyes and an almost hairless in his body. Nael grabbed Bluey’s hands guiding them towards my body, the young nineteen years old boy had his erection growing.

“I’m Kayron. I’m the second in command.” The tall black nineteen year old boy started groping my thighs. Before I realized it, the boys approached introducing themselves. The clear sky was above us as they brought my speedos down to have my cheeks slightly kissed by the sun.

“I’m… Herbert, but they call me Herby…” He was this sweet muscular eighteen years old brunette who was the first one to grab my bare ass. “So soft and round…” He was also the first one to get his majestic dick out of the speedos. The white anaconda was thicker than Nael already rubbing on the side of my cheeks.

Once they got the gist of it, the three boys had no qualms about rubbing their hard cocks against me from every corner. Even my legs, thighs and back… Every part of me was suddenly consumed by them. There were no lines or order, I was simply worshipped by them for being a bottom!

“Fucking Christ, that’s an artwork! Look at how wrinkly and swollen it is!” Bluey had spread my cheeks apart revealing my hole.

“You like it boys?” Bluey didn’t reply, I felt his tongue slipping in after he went on his knees. I had an innocent muscular nineteen year old light blue eyed boy staring at me with his perfect preppy blonde boy face while munching on my ass!

“Are you kidding? It’s gonna be an honor to taste the walls of a shithole that has been fisted Sir! I mean… I can only hope we can serve your shithole nicely sir, darn… Your shitbox is so cute!” Herby spread my cheeks for Bluey. “Holy shit bro, his cheeks are so fat and perfect! My hands just feel small around them!” He groped my ass harder.

I had a day of rest, yet my asshole was very sensitive from the dinner gangbang. It was so much so that I started pushing out against his tongue, a little bloom of an inch emerged from me.

“Bro, he’s prolapsing, man! We're gonna goon his dumpy so hard!” Bluey was sucking on my delicate anal flower to make my cock drip precum.

“Man, oh man! He’s precumming from pushing his guts inside out and you’re sucking it!” Kayron pushed Bluey away. “Save some for us!”

The three frat boys touched my exposed rectum, my walls folding out for them. They molested my ass and even sucked on my balls rubbing their noses on my prolapse.

“Ok boys, this is a learning experience. I know you’re all eager to play with a big anal slut as the fucking horny dumphole addicts you are, but you gotta watch his reactions… True anal destroyers always hear and watch their partners.” Nael took over the lessons when approaching to kiss me.

“Sir Leon, I… We’re sorry about it. It’s just that you’re so sexy and being with a guy that has trained…” The boys stopped. They stood up with their hard cocks when I turned their way to speak.

“No problem, I will love to slut out with you guys.” I eyed them being afraid of touching such youthful handsomeness. Their teen dicks were so huge, so full of energy. They pulsed for me, their eagerness to ruin my ass was shown off in their veins with bouncing poles anxious to penetrate my rear.

“It’s Leon’s first time in a lesson like this. He joined the A.S.S. recently so I’ll help you guys.” Nael grabbed my hands guiding me to their dicks. “Don’t be afraid, every guy who joins the Reaming Frat faction is a certified anal addict. It’s just that these youthful ones have their own lingo.” Nael let me explore those large teen cocks. Heck, Herby was so huge he was thicker than Nael! Both Bluey and Kayron were a bit smaller, but still, they were simply large with no less than nine inches of length and leaving me with difficulty to close my hand around their incredible girth.

“So, you… I mean Sir Leon. You like to stretch your back hole?” I felt them closing distance when Kayron asked said question.

“Yeah, feeling your tongues in there made me feel good. It’s just that I had been gangbanged by many guys not long ago and they really ruined me.” They pressed their huge poles against mine. My five incher looked incredibly small near the scale of their sizes.

“You’re very good looking, a perfect body for anal sex with those thighs and ass…” They fondled me, we all rubbed our cocks against one another, the boys were groping my body as Herby was the first one to address me in a sweeter way.

“And such a pair of man tits!” Kayron sucked on my left nipple as Bluey did it to my right one. Herby went on his knees licking my precum.

“You boys are being more gentle now. Make it sweet because being a bottom is extremely harsh and our bottoms will bravely face all the anal pain and destruction we have to offer then…” Nael grabbed me from my sweet delightful moment of being a faggot completely worshiped by three adorable teens. He made me sit on a chair to guide my ass towards the boys and position my cock in between my thighs. “An anal slut leakage means he enjoys you. Let’s not forget the reason why we love men, their cocks dripping for ass sex, eager to receive love in the holes they shit from, that’s a beautiful view. Now c’mon boys, let’s play again.” Nael let them free to pick what to do while he went away to grab some lube.

“Sir, can we….” Bluey grabbed my ass cheeks.

“Two fingers each.” Those words of mine were enough for them to slide inside me, three college boys with two fingers from each of their right hands made for six fingers up my ass. “Do you guys wanna take a look inside my dumper?” Turning back to watch their eyes, all eager for me, had my cock throbbing.

“I’m sorry sir, but we’re very addicted to man ass and yours is so big!” Herby was groping my cheek with his other hand.

“I love your excitement boys, it turns me into a hornier slut… You can spread my craphole now… I will show you my rectum!” The pressure started to rise from their six fingers opening my asshole, each one pushed in a different direction to really widen my gaping anus. These boys were a different type of breed, I saw joy in their pulsing cocks and a really strong effort to open me really roughly.

“Dude, bro… We can see so much of your rectum rings! Holy crap, we will see your colon if we work on it!” Kayron groaned.

“But… Isn’t it too much sir Leon?” Herby seemed to be worried.

“It is a lot…” My voice trembled. “Anal sex is very hard, very painful and very pressuring at times…”

“So, why do you let us wreck it so hard?” Bluey kissed my back trying to get me to relax.

“Because I’m addicted to anal stimulus… To feel like my craphole needs to shit itself out from so many bowel movements… To excite and turn on my sensitive insides, to generate so many anal pipes delights I piss myself from the burning ruination of my bowels…” The boys were all intensely throbbing with my confession.

“We’re so happy to be around a true anal bitch… Like man… Can we goon your shithole? Like truly goon your crapper?” Herby asked right when I was starting to prolapse, the boys let my hole free. They just spread my cheeks as I bloomed with some pee dripping from my cock.

“I’m a bit older, I don’t know this goon stuff you’re talking about…” They caressed my rosebud, it triggered shivers on me when it slowly went back inside my asshole.

“It’s like fucking you for hours Sir… Like masturbating your anus for a long period of time…” Kayron tried to explain.

“We will use our cocks and hands and anything available, Sir. We promise we will goon your hole really hard…” Bluey held my waste. “We will goon our cocks too… Like really hard Sir… Just for your wide dumptruck and your needy craphole until you truly feel those things… We will break your prostate and bladder too… We will make you feel like you have to shit yourself so hard…”

“But we will take care of you sir, we took care of all the boys that let us goon their bitch holes, but none was so keen… They didn’t even prolapse like you do… Please sir, we will care for you!” Herby was spreading my cheeks again. “Pretty please sir, we promise to drain our balls and make you shit so much cum… We will make you shit those guts inside out…”

“Ok, boys… I will let you fuck me up my turd chute…” It sank into my heart, their eager eyes turned to my body with Herby sliding his tongue into my asshole. The stretching of my ring was felt alongside his enthusiasm.

“You guys have been fooling around way too much. Now, it’s time for a serious job!” Nael was holding a few buckets, a native from the island had helped bring some others, leaving us alone after setting them nearby. There was a lot of coconut water in some of the vessels, but there were also some nicely sized spheres in there.

“What are these?”  It was Kayron who grabbed one holding it.

“Lube spheres. The thin surface tends to melt or burst away once inside.” Herby’s face was taken away from my ass by Nael.

“Oh man, I could spend a day tasting his shit tunnels.” The college boy complained.

“But we have to anally wreck our slut, it is the only way to make him feel good.” Nael pushed one of those spheres up my anus, I wanted nothing more than to push it out. “See, Leon was fucked in his bowels the night before last night. He’s getting used to getting wrecked when he feels all ruined and sensitive. You guys gotta help him.” Nael’s arm went around my hips, the familiar feeling took over my body. He was holding me once again, leaving me with no escape from the butt abuse.

“Don’t make these stupid faces, come on and help me push them in!” The boys positioned themselves following orders to put those spheres in. Nael’s fist was sliding up my already pained over sensitive anal cavity. The boys did the same when inserting more balls in me. Their fists explored my rectum smashing it. Those big spheres, which were a little smaller than their fists, were invading my depths. The fists became forearms, a burning soreness spread inside me once they alternated sliding more and more of their arms up my hole as. The deep discomfort of having one forearm going inside to push those spheres in only grew. Nael guided the boys to slot their hands deep up my colon, to disrespect my second hole in order to get the lube spheres to go deeper inside me. They gladly did it, I was soon clogged all the way up to my bowels with more than ten of those lube vessels stretching me out, driving my anal rings to want to shit it all out.

“I wanna crap out these balls…” I held onto Nael’s shoulder. “Please, it’s all driving me crazy… So many bowel movements!” He held my hole shut with his free hand, no spheres were coming out under his watch.

“No no baby, hold it in for the boys. Look at all these teen large dicks… They want craphole fucking to make them burst, and you’ll fart so much lube…” Nael held my hips with a tighter grip around his arm. “Herby, come around. Time to fuck your first true anal addict! Hold it in.” My hole shut close to obey my anal owner.

“Sir, are you ok with this?” Herby whispered in my ear. He was gently spreading my ass cheeks.

“I’m fine, I’m fine. Anal… You guys told me you were about to goon and turn me into a dumb anal gooner wanting to shit, right? Just polish my guts, it’s all right.” I spread my ass for him with a harsher grip.

“Oh fuck sir, it’s going to be an honor to make you feel like you wanna shit on my dick sir… I want nothing more than to drag my pole in your bowels…” The white German descent boy inserted himself in my anus slowly sliding into my colon, his cock went deep and expanded my rectum pushing those large spheres deeper into my bowels. I let out a loud wet fart with lube erupting from my craphole. “I think we burst one sir, no shame, the warm lube you’re shitting on my cock makes your guts feel so much better… Dude… He’s like silk and all loose but he grips in his contractions… Man oh man… What a cock sleeve you are… I wanna make you my shithole goon!”

Shivers run down my spine to intoxicate the rest of my body. My smaller cock went limp since I didn’t take viagra and I could only focus on my clogged bowels and his white large teen cock breaking them. I couldn’t lie, the anal desperation was much worse than the anal pain itself. Herby pounded away not letting any lube spheres escape me. He was rather brutal like the butt rapists on the dinner; there was an added energy though. The flow of his teenage years first experiencing a ruined man’s cunt made him put more effort on the thrusting, even more than those dedicated anal fuckers from the restaurant.

His cock, so violent I had to be held in place by Nael, made more spheres burst inside to fill me with lube. I had all that warm lube flowing out to make me feel like I was truly shitting, the sensations of a stomachache from the heavy bowel contractions added to the fantasy.

Everything was clean, but I was also peeing myself and shitting lube and farting it all over Herby’s energetic young large pole. It was confusing to me with all these butt ruination sensations running all over me. Everything felt incredibly good, but everything felt incredibly painful and uncomfortable.

“Good boy, don’t go cumming now…” Nael warned Herby. He switched places with the dark skinned black Kayron.

Kayron was much more dominant and decisive. He turned me around to lay on my back on a table with my legs spread open. The boy pushed five more lube spheres up my mancunt to make up for the ones Herby had burst.

“I will churn butter sir. Excuse me, but I really need to see the face of a faggot getting truly destroyed by a big black pole sir.” He thrust into me forcing his cock inside to the balls. That thing was the largest dick I had ever taken, the thickest one too. I pissed myself with the way he massacred my colon to really widen my second hole, to truly push the lube spheres up my bowels. My belly was even bulging from the cock stuffing and the lube sphere anally clogging me.

His truly handsome black face made me swoon. That young dark muscular teen gripped my waist to take me to pound town again. He was crueler, rougher and more intent on setting my ass on fire. I held onto him loving each second of what a dark cock could give me, falling addicted to his young spice setting my guts on fire and shitting lube on his brutal penis.

“Did you like black meat?” Kayron held me still, thrusting his pole up my hole with the intent of breaking it. He was a pure anal sadist by nature, a true bottom lover excitedly staring at my little cock. Despite the awful pain being almost unbearable, I held him too.

“You’re a perfect butthole rapist, I’d love to cry in your arms.” The boy was on a mission when I kissed him. He made me cry tears from his harsh wreckage. “I love huge black cock up my fuck pipes baby, Jesus… Fuck me in my colon!” He used that huge pole to go for it, to focus on my broken second hole making me scream from rough pain for his delicious teen black meat.

“My turn!” Bluey had to take Kayron away to slip the dark pole out only to insert his fist in. My anus had no rest. The boy caught more of those lube spheres and made sure that I felt his forearm going deep inside me. He put the lube balls deeper, reaching to savagely penetrate my colon. “You have to know a blue eyed white dick can wreck you too!” He took his forearm out to put his dick in.

“Of course, fuck me like you want to ruin my shithole with that big white cock of yours! I’m built to take it up my ass!” I felt him help me to be on my fours as he held one of my legs up to expose my limp cock.

“Oh man, your butthole seems like it’s hurting so bad… It’s so swollen and pretty!” He thrust his cock up my ass a couple times forcing some lube spheres to burst. I was once again shitting lube all over him and pissing from the insufferable pressure his cock exerted on my oversensitive insides.

“He’s suffering quite a lot now, especially considering how he was fucked up in our special dinner.” Nael approached from the front to kiss me while Bluey delightfully tortured my bowels with his penis.

“Dude, he’s loose, but at the same time he bites it… Fuck… Man… Feeling him shitting lube on my cock is so great…” The barely legal brutal ass fucker held me into his grip further pushing his cock deeper anally traumatizing me with each thrust. “And you look so cute pissing… Big ass, small cute cock bitch… That little dick is almost as perfect as your dumptruck!”

“Gather around boys…” Nael commanded when he glued his body to mine, Bluey kept fucking my butt with Kayron and Herby spread my cheeks to molest them. “This man is a gift from heaven. That’s why we worship anal bitches in the A.S.S… They all surrender a very important part of their bodies that’s not made to take so much, yet they let us destroy and break it for our enjoyment. Anal sex is rough, painful and complicated, but here he is… A prolapse bitch cumming from bowel pain and butt wrecking, a dirty ass slut loving the need to push out in his anal contractions, a pervert sodomite dripping jizz from his limp dick just before he squirts piss from colon pressure… He is a dream… Learn it boys, for when the time comes you will have one of these by your side. You just ought to know that you might have to be patient and help them become what my prize already is.”

Nael kissed me while the boys kept switching places to torture my anus. It went for a long while with them pausing only to let me drink coconut water to rehydrate and make me squirt more piss.

After getting pounded for this long, after hours of endless anal gooning as they say, I lost it. I had to admit that having sex at my shithole is nasty; I had to bear the blasting noises of wet drenched bowels wanting nothing more than to shit cum, lube and to prolapse non-stop. Each time their cocks or fists were withdrawn from my hole, I couldn’t keep my guts in. I blossomed letting them play with and slap my overly swollen rectum walls turning inside out to for a wide prolapse.

We all had to admit that rectal sex was simply wrong, heck… Even cunts and any orifices would be wrong for this nasty type of work. Yet, we couldn’t care. No one cared a bit that I was a loose bowel slut tortured on my digestive tracts, pissing myself from the heavy rectal stretching, pushing out and farting from the deep colon fucking, overwhelmed by my need to empty my bowels and wanting to shit myself in this heavy stomachache state. Even if I was all clean and all that was inside was tons off lube, natural anal mucus, hands and cocks; all I wanted was to shit.

I was an indecent sodomy slut shitting all that wetness in the form of foaming anal cream. These guys? They were sexy savages adoring and worshipping me, sweating in their efforts to make my dumphole sing a tortured tune. They loved it as much as I adored it. The brutal destruction of my wrong hole turned us all into anal addicts and no matter how harsh it got, in between pissing from the harsh anal pressure, I dripped cum!

It was a signal that nasty, wrong, perverted sodomy that made me prolapse like an animal in heat was a way to make me cry in deep gut pleasure. It all made us revel in the nicest and most destructive and incredibly painful shithole sex. The more I came from their teen forearms slipping inside my guts, stretching me wide open and treating my body like a punching bag, the more their delicious unrestable sweet teen large cocks assaulted me in my burning punished rear orifice, the more I came from anal pain and torture and pressure and contractions!

I truly became an anal bitch cumming so much with my handsfree limp cock leaking jizz from all in the ass destruction. It got to the point I couldn’t leak any more cum because the boys had drained all of it, my poor prostate couldn’t even refill my aching balls. Luckily, Nael was refilling me with coconut water so I could squirt piss non-stop during their brutal unresting violation of my guts.

At some point, Nael put me on my fours on a beach towel. It was already sunset time when the boys had already filled me with much of their jizz.

“We have to conquer one more limit…” Nael’s fist went up my hole. I felt him guiding Bluey’s hand towards it. “Hold him boys!” Kayron and Herby held me in place. Instead of trying to fight it, I arched my back. Bluey was slipping his fist inside my crapper.

“Aaahhh! This is so fucking painful!” I felt it in my soul. The beautiful sunset was happening right when my first double fisting broke into me. This was unbelievably rough after the whole afternoon of complete ass blasting I took from all these men. I peed myself from the worst anal pain I had ever experienced. Nael held hands with Bluey twisting their fists up my rectum. “Deeper!” I was already shaking when I reached behind to hold their arms and to offer my rectum for more abuse, they went in dipping both fists up my second hole, sliding down my colon. I cried in anal shock. Never had I felt such pressure making me want to shit myself.

“That’s it baby, you’re our bowel slut.” They took their fists out. I wasn’t seeing how Kayron and Herby were ready to plunge both their hands inside me. No relief, no time to prolapse, they just slid it up my colon with their deviant smiles shining upon my complete anal defeat. I was feeling a hose two deep double stuffing my hole.

“Fucking faggot filled up with our jizz!” Herby fondled my back.

“He’s our ass blasted whore!” Kayron moved, he was taking his and Herby’s fist out of me.

“Oh my god, I’m shitting my hole out!” I prolapsed big time, five fat inches of my rectum bloomed to our joy, it hanged in there with the boys worshipping it, licking, sucking, slapping and even pissing all over my bitch hole.

“That’s it for the lesson boys. I appreciate the help with blowing him up.”

Nael had ended my torture. He guided my prolapse back inside my anus to finally spread it. I felt the flaming inflamed walls of mine emptied, finally open and gaping. My tunnel, which nature was to produce long and fat prolapses, to bloom with a red pervert tail from being brutally anally destroyed, finally gaped wide open without closing itself. It took a minute for it to have my anal rim finally closing.

“Good boy!” That was the last thing I heard before dozing off to sleep. It was the first time I had fainted into deep sleep from full anal exhaustion.


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