Milo's Cherry

Warning: incest, age difference, humiliation.

Once upon a time, in a leafy sunny suburb, there was a big cozy house with a cute and caring young man named Milo. When the day of his eighteenth birthday came, he was thrilled and excited, because his mom had left early in the morning to buy his favorite chocolate cake.

Milo was a rather lovely-looking fellow. His body was short and slim like a deer, and his skin was pale pink and soft like a peach. His hair was a light caramel, exactly the color of his sparkling caramel eyes. Not only that, but his nose was red and freckled, and his mouth was round and plump... and he had the most perky round rump.

Milo had a big and bold dad called Truck, a prosperous contractor and car enthusiast. Truck was the best father in the whole world. He was fifty years old, and his body was tall and burly like the frame of a fierce bear. He had a bald and shiny head, a big and bulbous nose, and a thick and trimmed beard... and the fattest bulge Milo had ever seen!

It was true that Milo had not much in common with his dad, not like his big brother Brock anyway. Brock was a big jock, and a huge success with the ladies in the university. He was all muscular and cocky, just like his father, and he liked giving Milo some wedgies once in a while - it was rather embarrassing.

Brock's wedgies would always make Milo turn red like a tomato, but he laughed along with his brother and father, because he loved them so much, and they protected him at all cost. Sometimes Milo felt sad that he was not manly and masculine like his big bro, but at least he had someone to play with. And Brock would come home for his birthday soon!

Anyway, that day the house was silent in the morning. There was a rather warm and golden sun outside, and Milo got out of bed as his mom's car drove away in the distance. He would be alone with his dad for the entire day - big dad and twiggy son all alone in a cozy warm house... what could happen?

He tiptoed to the bathroom and took a nice shower for his special day - his dainty hands rubbing soap all over his dainty body. It all felt rather smooth and... completely hairless. He did not have much hair at all, but the little he had was almost unnoticeable, and he enjoyed shaving to pass the time... and to feel good and girly, to be quite frank.

When he came out of the shower - his perfect pink skin smoother and fresher than ever - he decided to wear his light blue shorts and his extra tight white tank top, and some white sandals. He adored that look because it made him look extra soft and feminine and a bit sassy. The shorts made his bubbly but look juicier, especially when worn without underwear - his plump cheeks swallowed a bit of the fabric in the back, and his pink penis made a cute little tent in the front.

Truck very much enjoyed seeing his runt son in that type of outfit. The dad's rather fat hog became instantly excited every time the cheeky buddy walked in front of him in the living room, as he watched the sports channel and sipped on his cold beer. He chuckled as Milo pretended to trip and fall on the fluffy rug in front of him, just to tease him with his virgin butt - and what a cock tease! The dad chuckled and asked for another bottle of beer.

The father's cock would not stop throbbing during the entire game, and a horny idea started to develop in his mind. Now that his son was eighteen years old, he was free to experiment with him as much as he wanted, even teach the cute runt a lesson for always being such a sassy sissy. It was true that having a gay son was not necessarily ideal, but since he had another son, Brock, who was a total alpha like him, it was not the end of the world.

Brock would pass Dad's manly genes to the next generation, while Milo... well, the boy was clearly a faggy fairy - not in a bad way, more like in a horny, cock-triggering kind of way. The more Milo grew and evolved, the more obvious it became: the sassy buddy was clearly destined to get dicked down. The father constantly thought of the man who would eventually pop his son's cherry. Would he be kind? Would he treat his son right? Was he deserving of such a special treat?

Now that Truck deeply reflected on it, he came to a sudden sexy conclusion: if there was a man more fit to pop his son's cherry, that was him. After all, he knew his sissy son inside out, and Milo loved him and trusted him... and teased him more and more. It was time to inaugurate Milo's virgin butthole, Truck decided firmly.

When the cute runt came back with another beer, Truck told him to sit down on his hairy thigh, and the little fag did not hesitate. Truck grabbed Milo's cutesy waist with his bear hand and smirked at Milo's blushed face. Before he could even say anything to his son, he noticed the horny buddy was twitching in his tight shorts, a cute little tent forming right in front of him. The girly guy tried hiding it by placing his twiggy arm on top, but it was too late.

At that moment, Truck decided to be completely honest with Milo. "Look, buddy, you are my favorite son, you know that?" Milo seemed quite surprised by the declaration, and his freckled face blushed a tone darker. Dad let out a masculine chuckle and started singing sweet nothings in his ear. How he preferred Milo, how he thought Milo was such a cute buddy, how he always wanted to hug and protect Milo, how he would always be there for Milo.

As he sang more and more praises in the sissy son's ears, Truck felt his big boner throb more and more, until it became fully erect, pressing right against Milo's soft thigh. The son's eyes bulged in shock and admiration - he had clearly never seen something so big and bulky - and his mouth was almost drooling. It was time to put the bubbly buddy in a big-cock trance, the trance his mom was very used to. In a moment of sexual aggression, the dad pulled down his shorts and revealed his large throbbing member.

Milo saw stars inside his little brain. He had never seen something so large and masculine-looking, yet so enticing, so appetizing, a cocky cock display. He almost felt proud of his father. The powerful penis was like a big fat snake, rubbery foreskin intact, a big red head with an upward shape, big juicy veins all over the sexy shaft, lots of hair on the base, and huge fat nuts hanging low in a saggy sack between the thick thighs.

It was the most brutish sight Milo had ever seen. So manly and cheesy, yet so yummy-looking. Milo could not help himself. His pink brain was almost melting with such a strong and large sight in front of him. It throbbed against his own leg, getting closer and closer to his own little tent, as if teasing him, laughing at his face and tempting him with sexual aggression. His father's sexy sausage was three times bigger than his perky penis! BOOM! His sissy mind was in shambles.

Truck grinned and chuckled in his son's face, and asked if he wanted a taste of his big bulky rod. Milo nodded in silence, mouth gaping and eyes glistening, in a clear girly trance. Truck grinned wider and grabbed his son by the waist, easily lifting him off the couch, placing him over his right shoulder and taking him upstairs, to the parent's big bedroom.

It was rather hard making the way to the bedroom. Every step felt like a missed opportunity to simply strip Milo and pound him right there on the living room floor, or on top of the stairs, or in the middle of the corridor, but the hung and horny dad was able to make it. He threw Milo onto the big bed, the same bed he had used to take Milo's mom's virginity on their honeymoon. Now it was Milo's time to be ruthlessly stretched out - in the butthole!

Truck's wife never let him use her butthole, and he had been hungry for some bum fucking the entire time. Years and years of marriage, and a lot of pent-up aggression and horny build-up. He was ready to turn Milo into his perfect butt toy! It was a win-win situation for the burly father: one alpha son to pass his genes, and one cute sissy son to stretch - perfect patriarchal victory.

Milo felt his whole body shake and tingle, and he fell flat on his belly, right onto his dad's big bed! It was his favorite bed: a rather large and expensive mattress that felt like heaven on his sugary pink skin. It was as if he had laid on a cloud, ready to be taken and used by his favorite man in the entire world! A sweet sissy dream-come-true!

Truck lay on the bed right behind his son's cute rump, and undressed him slowly. First the cute little tank top, exposing the perfectly silky back and a small hint of pink nipples. Then he pulled down those slutty shorts, and his mouth watered staring right into the peachy butt crack: it was the most perfect and immaculate sight, an almost unreal-looking fuck-pudding. Perfectly pale and pink, smooth like silk and yogurt, with the tightest little pink star right in the middle!

Truck's hot hog throbbed angrily between his legs, ready to stretch and destroy, but first, he had to taste that delicious-looking cherry. Milo felt his father's hot beard pressed against his sweet cheeks, causing goosebumps all over his twiggy body, and then a big fat tongue, a burning-hot snake, rubbing and twisting right against his most intimate spot. He had never felt anything against his butthole before, not even his own finger! It was so strange yet so magnetic. He felt as if being devoured by a big bear, and that made him a bit afraid of his dad for the first time!

Milo felt his tremendously virgin butthole get lick-fucked by his dad's manly tongue, slowly pressing against his untouched pink pucker and trying to go inside! The pressure was so interesting, and he could not help but let out a small sugar fart right on his father's tongue. His dad chuckled and kept tongue-pounding him shamelessly, as his entire bubbly body reddened and burned in shame.

Truck enjoyed the sweet taste of virgin pucker in his manly tongue. Realizing his son had a perfectly hairless butthole only made his schlong throb harder - the sassy sissy was clearly shaving it regularly... the little fag! He was begging for it. Truck was about to give his rosy rump the pounding of his life. Between deep licks, he asked Milo if he was truly a virgin, and the son innocently answered yes, and also said he had never played with his butt before.

Truck grinned and took off his shirt and his shorts, becoming fully naked and manly-comfortable right behind his son. The easily-impressed sissy turned his head and admired his dad's rather masculine, muscular, fat and juicy, extra-hairy, real-man body. Milo was clearly into it, like any real sissy would be. His tongue almost came out of his mouth, and he let out a little... bark? The dad chuckled.

"Do you like that, little sissy? Do you like how manly your dad is?" Truck asked Milo casually, and the runt son nodded eagerly. "I also like how soft and skinny you are, my dear son," he said right in Milo's ear, and lay on top of him, locking the cute body in place, and spreading his fat hairy legs in order to position his lewd schlong right between Milo's well-lubricated butt cheeks.

"Ready to lose your virginity forever, son?" He asked in Milo's ear. Milo felt cute shivers run through his body. He could not believe how intense it all felt, his dad's body right on top of him, pressing down on him, every bone and every muscle, the big hairy belly, every hair on his dad's body tickling his soft skin and causing sissy goosebumps he would never forget. "I'm ready, Dad," he answered eagerly.

"Are you sure, son? Once I'm in, I'm not stopping, and you will be my sissy forever..." Truck warned in his son's honey-tasting ear. Milo felt rather afraid when he heard that... "Forever? There's no turning back?" He asked innocently. "No, buddy, when my fat fucker is inside your sugar pipe, you can never be a man again. Are you okay with that?"

Milo felt a small tear leave his left eye. He knew this day would eventually come. The day he would have to face his deepest desire. He dreamed of this moment, of being taken by a real man, of feeling like a complete bitch for a manly, god-like figure. He had never imagined that man would be his own dad, the man he had always secretly desired... and now, it was time for Milo to lose the last little trace of "man" in him, the "man" he could never be anyway, not with such a cute and bubbly body.

"I'm ready, Dad," he answered in a rather girly tone. Truck let out a manly, rather evil laugh in his son's ear, and pushed his cockhead right into the runt's poor pucker. The pressure was incredible. They both felt it: Milo felt his innocent pink pucker try to resist the invasion. Truck felt his rock-hard cockhead throb aggressively against the extra-tight, soon-to-be-used sphincter. "Haha, you stand no chance," Truck thought comically. "Open up, sissy fag son."

POP! The funny sound echoed in the room. Pucker invaded. Cockhead inside. Truck let out a victorious grunt. "Are you okay, buddy?" he asked as he throbbed inside his son. "Yes, Dad, I think so... but it hurts..." Milo answered meekly. "It's natural, son, don't worry... you'll enjoy it once you get used to the girth," Truck grinned. Although it hurt some, Milo was very excited by his dad's words and felt his own perky penis twitch happily against the mattress.

"Ready for the big plunge, son?" Truck asked. "W-what?" Milo stuttered. The rather horny and sexually aggressive dad laughed warmly and decided to show his son what a big plunge meant for a sissy: feeling a meaty manly sausage slide right into the depths of one's butt. He released his fat weight onto the skinny runt and let his long schlong dive deep with gusto. POW! "Take it, sissy," he said in his head.

Milo let out the most feminine and embarrassing sound, and his head started to spin with stars and waves of deep sexual defeat. He would never forget that sensation: his dad's entire fat hog sliding all the way inside his devirginized butthole! It was both painful and deliriously sexy, and he could not help but cry more tears of masochistic pleasure.

Truck asked if everything was alright, and Milo took a minute to confirm. The son was clearly struggling to adjust his virgin "pussy" to his dad's meaty schwanz, but it was worth it, Truck concluded: being buried inside that sweet bum was the most delicious feeling he had ever experienced! A true moment of patriarchal enlightenment - he realized right at that moment that his journey as a man was complete. He had created the perfect fuck-pie with his own fat balls, and now it was time to eat it.

"Alright, son, get ready for our dad-son fuckfest," he warned in Milo's buttery ear. Milo only moaned in response - he was physically powerless, clearly past the point of instinctual resistance, his pucker stretched to its limit, his mind melting with the hairy heavy weight on top of him. And so the hardcore fucking began, loud and rough, starting at an intense heavy pace, and then locking in a steady medium-speed pounding.

Milo saw colorful stars everywhere. His dad was driving that fat sausage all the way into him over and over again. Truck chuckled and kept the deliberate longdicking at a constant pace, making the faggy fairy feel every inch with every heavy stroke. To make things worse, the large bed started squeaking with the weight of such intense butt fuckery. Milo felt his face blush again - it was so cheesy, yet so mind-blowing to be anally debased by his big strong dad!

The anal use and abuse continued for a long while - after all, father and son had the whole house for themselves. Milo felt the musky sweat dripping from his dad's big bear body and soak him up in a puddle of manly sex. Their bodies clapped loudly, and the bed squeaked lewdly. Milo finally looked back at the mirror in the back of the room, and he could see his dad's big hairy butt shaking and twerking as the hard pounding continued! It was a rather hypnotic sight.

It was even more hypnotic and mind-blowing when he saw another sexy scene: his dad's big balls were bouncing up and down and hitting his soft taint, and his cute bubbly balls! Big dad nuts bouncing and slapping up and down against girly son bubbles! That was too much for Milo's poor little sissy mind. He felt something warm build up inside him, and suddenly, his pucker twitched all over his dad's cock, and his cute penis was squirting... a soft sugary juice.

Truck noticed the reaction and approached his son's ear again and told him the truth. "You've just had your first sissygasm, son. How's it feel?" Milo drooled and his eyes rolled back in a rather intense sensation. It was true... he was having a... sissygasm... and it felt very sexy and taboo! "It's true, Dad! Thank you, thank you!" Milo chanted. "Thank you for giving me a sissygasm!"

"Oh, fuck!" Truck roared. "Then get ready for my thick spunk! It's coming, son!" Milo squeezed his dad's cock with his butthole and begged him real good. "Yes, Dad, please! I'm ready for your thick spunk!"

The rather strong, superior and manly father grunted and roared and intensified the delicious butt buggery. It was as if every inch of his rock-hard schlong was being massaged by a very soft and tight cloud, a buttery and warm cloud - the best feeling in the whole world! He would have the best orgasm of his life, all thanks to his faggy sissy son!

More buttfucking, more body clapping, more ball slapping. PLAP, PLAP, PLAP. The bed squeaked and the air was filled with dad musk and dad assfunk. Truck's primal brain took control of his burly body, and it was time to breed. It was time to dump semen... discard jizz... deposit spunk. Breed, breed, breed. "Here it comes, son!" the dad shouted proudly, and erupted in a perfectly long, strong and thick orgasm, filling his own runt with the same juice that had created it - the perfect cycle of life!

After some intense semen dumping, and ear-kissing, Truck stood up and reached for a cute pink package in his drawer. "Look, I was hesitant to give you this for your birthday, but now I'm sure you will want it." Milo grabbed the small package - his butthole gaping and twitching - and moaned meekly. "What is it, Dad?"

"Open it," said his dad. Milo was flabbergasted! It was the cutest panties he had ever seen: pink soft cotton, simple yet sassy, and it felt great against his smooth skin. It even made his butt look extra round and juicy! It was the most exciting gift he had ever received. "I love it, Dad, I love it!" Truck grinned, his cock throbbing again. "I knew you would love it, sissy buddy."

Seeing Milo in those pink panties was too much for the very hung dad. He pulled those panties to the side, exposing the well-used hole for his growing godly dong. He pinned Milo against the bed again, this time holding the twiggy wrists with firm hands, and spreading the twiggy legs with his big hairy tree-trunk thighs - and holding Milo's Achille's tendons in the gap between his big toes and index toes - and proceeded to pound away for the entire afternoon.

First, the proud father kept power-pumping his sissy son in the same prone-bone position - it was a rather caring and comfy position for some lewd dad-son sex. Nothing wrong with that. But after a good hour of sleazy fucking, Truck wanted to explore new angles with his favorite son. Milo felt quite weak in the knees during the entire experience, but he trusted his father and wanted to learn more with him.

Truck grinned mischievously and knew exactly the first new position he wanted to teach the faggy fairy. He would show Milo just how light he really was! He turned the buddy around, grabbed him by the waist and pulled him in, the flat soft torso clashing against the forest of muscle and hair that was his dad's body. The flimsy arms instinctively hugged the dad's large shoulders and thick neck, as the strong man held him by the twiggy thighs. His girthy dong easily found its way inside again, and so the fucking continued.

Milo was positively shocked and surprised! He felt like the lightest leaf in his dad's arms, as the strong bear-like body kneeled on the mattress and powerfucked him with manly ease. Now he could feel his dad's juicy chest and big hairy belly pressed against his soft skin, and the big bear hands holding him firmly, as his butt-pie was ravaged in a fast and furious rhythm. But not only that: now he was face to face with his dad! That big masculine face with its sexy manly beard. Truck grinned and grunted right in front of him, and it felt much more intimidating than before.

Truck chuckled when he noticed his son become shy and the buddy's cute face blush in front of him, the sparkling puppy eyes staring at him innocently - it sent a new wave of fuck fuel down his spine. "What's the matter, puppy? Feeling shy, yeah?" he said clearly and confidently, just to make the sissy blush even more. Milo answered with soft moans and cute whimpers, and kept turning red like a tomato.

Truck kissed his son's cute forehead - and that made Milo feel all warm and soft and loved - and then he intensified the fucking to a stronger velocity, pounding so hard that his big nuts jumped up and down and clapped Milo's butt cheeks. It was so intense that the sound of ball-slapping could be heard in the room - a perfect cherry on top to make Milo blush ever harder - the freckles on his nose sparkling like stars in a sunset sky.

As he proudly pumped his son's poor pucker for the next hour, Truck carefully thought of the next position he would use for the butt abuse. "Hmm, what can I do to make this sissy melt?" he wondered, in his horny manly trance. When the idea finally came to mind, his dad heart beat faster and he let out the biggest dad smile.

"Now it's time for a Full Nelson, son!" Truck announced. "A Full-what?" Milo inquired innocently. The father let out a mischievous chuckle and prepared the yummy position. He lay on his back, and grabbed his son by the waist again, turning him around and making him lay on top of him, also on his back. Then he pulled Milo's legs by placing his thick arms under the sissy's knees and folding the buddy's body in half, all the way until his big bear hands were able to grab the back of his son's head!

"What?!" Milo let out in sissy shock. He had never considered such a funny and shameful position before. His legs were spread wide and his body was folded in half, right above his dad, and the big dong was finding its way inside him again. He felt completely powerless - because he was powerless! - and the worst part was that he could see himself in the mirror at the back of the room. He was nothing but a fuck puppet in his dad's big hairy arms! Truck could not help but chuckle at his sissy son's moans of surprise.

To make things extra horny, Milo's perky pink penis jumped out of his pink panties, twitching like crazy, and since his head was being held down by his dad's hands, he had no other option but to look at it! His penis was twitching with the new idea, and looking at the mirror, it was even more shocking: his dad's dong, three times bigger, contrasted greatly against his dainty dick! The size difference was funny and sexy at the same time. Both dad and son stared at the mirror and watched the lewd comparison, as the Full Nelson fucking started.

Truck kept a fast pace of dominant longdicking. Being the man in the room, his power was only highlighted by his position in the Full Nelson: lying comfortably on the soft mattress, hairy tree-trunk legs spread wide, big strong arms holding the bitch in place, and hips at full steam, stretching that pucker mercilessly with his girthy god-cock.

Milo kept moaning and whimpering and melting in his dad's arms. Being the bitch in the room, his lack of power was exposed by his position in the Full Nelson: lying uncomfortably on top of his dad's muscular torso, thin and weak legs spread wide by his dad's solid arms, his own shaking arms trying to gain some balance and failing to do so, and his poor pucker stretched out to its limit, being punished with every long stroke, as the force made his own perky penis jump up and down in the air.

The interesting thing was that at that point, the heat in the room was rather intense, and Milo's sweet scents had evaporated in the air and were replaced by his dad's manly musk. He could feel it in the air: the scent coming from his dad's muscles, the hairy armpits, the manly balls and the asscrack between his big hairy glutes. It was not an unpleasant combination of smells, Milo concluded. It was like a symphony of manliness, accentuated by the heat coming from such a big hairy body.

Milo was surrounded by his dad's sex smells. "Wow! This is what Dad's sex smells like!" he thought to himself. And the more Dad pumped and pounded, the more intense it all became. When the afternoon began to end, Milo was a in puddle of Dad's sex funk - Dad's burning-hot body slippery with macho sweat as they moved in a fuck cloud. He had never imagined sex with a real man could be so intense.

The intimate dad-son intercourse continued for another hour, until it was time for another comfy ejaculation. Truck reached the second cock climax as soon as he noticed Milo's legs started to shake and tremble - after so much hard fucking, the runt was clearly weak in the knees like a well-used fuckmeat. It was rather hot knowing he had caused it, Truck concluded. Breed, breed, breed. It was time to breed again. Dump, dump, dump. The father accelerated the longdicking motion until he was ready to shoot.

"Fuck, fuck, fuck, I'm cumming, sissy boy," Truck announced and roared into a powerful ejaculation - his legs spreading wider and his hips jumping higher for extra impact. "T-thank you, Dad, thank you for cumming," Milo said awkwardly, as his hole was being filled with another great load of thick dad sperm. "Ahhh... fuck... you're welcome, ya little runt!" Truck said and pumped more semen.

The afternoon was almost ending but they still had time for a horny hot shower together. Truck turned Milo around and inspected his well-used butthole for a few minutes: the pink pucker had been completely stretched out and would not close for a while. "Sweet," Truck thought. Proud of the anal wreck, he chuckled and gave his son a playful slap in the butt.

Then he grabbed Milo by the waist, and easily carried him to the private bathroom. He helped Milo take out his pink panties, and rubbed his soft body with soft soap, and kissed his naughty neck, his cute ears and hugged him with love. Milo felt as if his body was floating in a cloud of muscle and warm water, and he did not want that feeling to ever end. They both enjoyed a long and sexy and steamy shower, rubbing each other's bodies until the sunset came.