Disclaimer: This story contains bondage, humiliation, torture and male on male intercourse. Turn back now if you don't want to read about these themes.
Here follows the story of Sean who wants nothing more than to lose his virginity. But the night takes an unexpected turn for the weird – and weirder still.
MASTER RED SHOES
Sean's mind was set on getting fucked. There was only one problem: He had no one to fuck him.
Recently turned 16, the boy lived in a tiny town, where nobody was openly gay. Without a car, he had no chance of getting to where he needed to go to meet a man.
This didn't stop him from surfing various apps. Just in that moment he sat at the dinner table with his mum and little brother, scrolling through profiles of guys who lived miles away.
"Sean," said his mum, in her overly worried tone. "Sean, are you listening? Your brother has a doctor's appointment, and I... Sean, put that phone down."
The teen sighed, but complied. He laid the phone on the table and looked expectantly at his mother.
"Tomorrow," she continued, "I'll drive your brother to the doctor in the city. I'll stay with your brother overnight at granny's place."
Sean's mood lit up. That meant only his father would be home. Getting some time away from his overbearing mother would allow him to bring out the porn magazines from under his bed for once. His dad locked himself into the basement all the time anyway, to work on his projects.
But his mum wasn't done. "Dad is working late again the whole week. I don't know what he does at the office night after night."
This was amazing news. Sean never had the house to himself. Even though he only saw his dad for what felt like five minutes a week, he was never truly home alone.
If he ever got a sex date, this was a rare opportunity to schedule it. Unfortunately, there was no such thing on the horizon.
The boy finished his plate and went upstairs to his room, pondering his options.
As the night progressed, Sean got ready to shower. He stripped in front of his body length mirror, practicing to undress sensually.
His tight shirt came off first. The boy was a slender teen twink, with smooth, tanned skin that he took great care of. He swung his hips to imaginary music and looked his reflection in the eyes.
A youthful face with soft features and not a hint of stubble. His eyes were half covered by strawberry blond hair falling evenly over his forehead.
His nose and ears were tiny, compared to his lush lips – a result of his mixed heritage, leaving him with a hint of exotic aspects. He wished he could get a face piercing or two, but his mother was strictly opposed.
Giving his hardening nipples a quick pinch, he moved his little fingers down his fatless body, lightly touching the modest definition of abs – just barely visible in good lighting.
He grabbed his jeans and underwear and yanked them down at once.
Sean didn't exercise much, but he never forgot to do his squats, leading to a bouncy bubble butt on his otherwise skinny body. His legs had gained definition as a side effect. He kept them hairless.
Just as he stepped out of his jeans, his phone bleeped.
One hand on his shaved crotch, he looked at the notification.
His online profile had a picture of himself in front of his mirror, and a few other position of his bed that he considered the most revealing. He was naked in all his pics, but took care to crop out his face. He wasn't stupid after all.
He also had aged himself up to 18 to use the app, but that was nothing he thought much off. His profile read like this:
Slut_Hole (18): bottom, new to this, looking for action.
The notification came from a new user. His only pic was of a pair or brand new red running shoes. The profile said:
Red_Shoes (40): Dom, top, looking for boys to serve me.
Sean read the message. His dick twitched in his cupped hand.
Red_Shoes [Hey bitch. Great ass. Ready to serve an aggressive Master?]
The teen didn't think much off the whole thing. Without a picture he didn't know if the man wasn't 200 pounds of fat covered in smelly grease.
He was about to leave for his shower, when he saw the little side bar: "Red_Shoes is less than 1 mile away from your location."
This was his first ever truly viable option. Finally he had found a user he could actually meet up with. Sean wrote back.
Slut_Hole [Thank you, Sir. I'm glad my ass looks inviting to you. Can I see you too?]
Seconds later Sean received a picture of the thickest, juiciest dick he had ever seen. Trimmed black pubes grew around the massive base, branching out onto pronounced abs.
Slut_Hole [Sir, I'm ready to serve such a beautiful cock any day.]
Sean was about to add that he was a virgin, but the man was faster, sending a link to a map. It indicated a warehouse next to the local park.
Red_Shoes [Be there at 5pm tomorrow, slut.]
The teen rejoiced at the coincidence. His only parent-free day was the perfect date. He vaguely took note that his dick was fully hard and leaking a shiny drop pf precum.
Slut_Hole [Sir, I promise I'll be there.]
He didn't get a response. After waiting for a minute to hear back from Red_Shoes, slowly massaging his dick, he gave up. Sean left for the shower, jerking off under the hot water, to the thought of servicing his first dick.
The night came and went. The morning passed. His father left for work, before Sean got to see him. His mother was annoyingly worried about everything. His brother was a bundle of cries and demands, but fell asleep in front of his favorite cartoons. As usual.
Eventually, the time had come. Sean was alone.
He cleaned his ass, took a shower, fixed his hair and applied all sorts of lotions and crèmes to be extra smooth.
As the hour approached Sean grew incredible apprehensive. He talked to himself, trying to calm down, but his heart didn't stop beating like a drum. And his boner didn't stop twitching in his skinny jeans.
He texted a simple [I'm on my way, Sir] and left the house before he could chicken out. Passing by the grocery store, the cinema and the library, Sean was quickly at the park.
The warehouse looked abandoned. He didn't quite know where to enter.
His phone bleeped.
Red_Shoes [If you're here, go to the back. The door is open. I'm not going to come out for your little ass, just find your way in. leave your clothes on the table. If I see you wearing anything on your body other than what's on the table, I'll send you home.]
Sean swallowed hard. He ran around the building and entered through the only door. It was very dark inside, the only light falling in through high ceiling windows covered with shades and ancient dust. He could barely make out shapes at first.
There was a table. Saddened that his strip-exercises were going to waste, he undressed as quickly as possible, putting all clothing on the table one by one. Stepping out of his shoes, the teen took off shirt and belt in quick succession. Getting rid of his skinny jeans was a bit more time consuming. His underwear came right off with it.
As he put the socks up on the table, his eyes were slowly adjusting to the dark. One last phone notification explained the things he had to wear. The instructions included turning the phone off afterwards.
The cloth item was a blindfold, which Sean had to wrap around his head, but that would come last, of course.
First he was to put on four leather bands, one for each wrist and ankle. They had D-rings attached to them. Whoever Red Shoes was, he must have arranged things like this many times before.
Once the teen had fixed all bands in place, he read the text one last time. He was not allowed to speak at any time. By putting on the blindfold he agreed to do whatever his Master was going to decide.
After deactivating the phone, he put the blindfold on with trembling hands and stood there in the mildly warm, dry air of the dark warehouse, shivering.
Someone tall walked up behind him and spanked his butt once, holding onto the slapped cheek with a firm grip. Sean involuntarily jumped. His dick stood at maximal hardness. His breath was heavy and deep.
The man behind him grabbed a handful of hair and pushed Sean forward. The boy stumbled further into the dark.
Red Shoes didn't make any voluntary sounds, but Sean could hear the patter of running shoes and the regular deep breaths behind him. The man's hands holding the boy's neck had to be huge.
Sean's crotch hit a block of wood and leather. With a brutal push, the blind boy was shoved onto a sawhorse. He flinched as his slim stomach and chest hit the cold leather.
Seconds later Sean was pulled by his hair until his chin lined up with the end of the sawhorse – his ass on the other end sticking out. His dick was pressed against the wood, letting the boy feel his own pulse.
The D-rings on his wrists and ankles were quickly fixed to the construction's legs, immobilizing him. He lightly humped the sawhorse, stimulating the base of his dick.
Master Red Shoes went around him, evaluating his body in the near darkness, Sean could hear his steps, through the blood rushing in his ears.
As the man arrived in front, he let his fingers slide over the teen's mouth and pushed in until he could pry the unresisting jaw open. Metal scratched the inside of Sean's mouth.
As the Master fixed the gear, Sean recognized the item as a spider gag. His mouth was held wide open, he was unable to speak. The gag's ring-shaped body kept him ready to take anything into his little mouth, while its metallic legs scratched his cheeks, as a warning not to resist with any futile movements.
Master Red Shoes leaned down and spit into Sean's mouth. Since the position made it hard to swallow, Sean let the saliva stay in his mouth from where it dripped down his lips.
The dick was massive. If the teen's lips had not been parted by a metal ring, the Master's member would have done so. Red Shoes shoved his dick right into the waiting mouth without stopping at the triggering of violent gagging.
Sean felt like he was about to puke. He didn't even get to enjoy his first blow job, the dick in his mouth was already past the tongue, the Master's pubes hitting his nose.
The boy didn't have enough in his stomach to vomit, but coughed up massive amounts of bitter slime. As if Red Shoes appreciated this self-lubrication, he grabbed a fistful of hair and fucked in and out all the way, giving Sean just enough room to breathe in between strokes.
The blindfold was quickly wet with streams of tears from Sean's reddened eyes as he received hit after hit of the Master's dick. No relaxation was enough to stop him from gagging with every thrust.
Through his own misery he heard the low grunt of his violator. It took half a minute before the dick plopped out and smeared precum, saliva and puke all over Sean's face.
The boy heard a tearing sound and was slapped in the face with a cloth. Red Shoes wiped the slime off his face before going back in.
This time Sean's throat was already burning but well lubricated and the gags came out as blubbering as if he was drowning. His whole body trembled on the sawhorse, trying to tear itself lose from the oral torment.
As the Master stopped once more, he caused a clicking sound a few feet away. Sean could feel the warmth of massive lights on his skin. For the first time the Master was seeing him properly.
Sean heard the man stagger as if stumbling away. The dom's heavy breath became more hissing. Had he done something that shocked him? Was Sean bleeding?
Seconds past in silence, while the boy became more and more terrified. Eventually, Red Shoes stepped closer again. Opening his eyes wide behind the blindfold Sean could see the actual bright red, brand new running shoes stepping up to him, thick hairs legs sticking out of them. Then the dick went back into his mouth and Sean closed his eyes as there was nothing more to see.
Very slowly the teen's throat got used to the painful hits and he found a good breathing rhythm. The violent nature of his gagging subsided.
The moment the boy didn't gag for three consecutive thrusts, Master Red Shoes pulled out and left. Again Sean was afraid. Would he be left alone like this? His heart raced, his dick pumped. These lights were getting hot on his back.
A whip hit his slim shoulders. Sean screamed through the ring that held his mouth open. The hit was followed by more, making their way down to his ass. The small of his back was especially sensitive. He squirmed and rattled the D-rings but could not get away.
Spanking both bouncy butt cheeks alternately, Master Red Shoes used his spare hand to reach forward and rest it on Sean's neck, stroking it gently – lovingly, almost. The boy meanwhile was sobbing from the rising burning on his ass.
Red Shoes kicked the teen's knees apart and spread his cheeks to whip the hole. Sean quivered and tried to beg him to stop but the gag kept his words from becoming anything more than grotesquely intonated moans.
Once Sean's dance of pain had taken on a rhythm and the boy jumped in anticipation, knowing the exact moment the whip hit, Red Shoes finally stopped.
The boy heard his Master kneel down and felt a tongue pressed on his sore hole. Sean was getting rimmed. Up and down flicked the Master's tongue, from the beginning of Sean's crack to the point where his scrotum began. Then the flaps became faster until the tongue rested on his hole and applied pressure. The tip popped in. Sean whimpered. At last, this felt amazing.
It ended too soon, with Master Red Shoes standing back up. Instead of more tongue a finger entered Sean's asshole, prompting him to yell in surprise.
The finger was lube-covered and distributed its content inside the boy. It went out and back in once more to apply yet more jelly to his intestines.
Sean wasn't sure if he wanted what was about to happen, but it was inevitable either way.
At first he thought the dick was knocking at his backdoor already, but the object was smaller and plastic. He was being filled with a plug.
It was easy for the thin little plug to pop in and stay in place. The discomfort was minimal, but that also meant that Sean was barely being spread. The device served as reminder more than preparation. Once again, the boy was left alone for a moment.
The sawhorse was fairly thin, allowing even the slender Sean to have his nipples accessible. Red Shoes use that freedom to fix clothespins on the boy's tiny, hard nipples, making him tremble again.
Twisting the pins slightly, the Master caused intense spikes of pain in regions that Sean had never considered particularly sensitive. The boy sobbed and kicked out to no avail.
Catching his breath again, Sean whimpered through the metal ring, the blindfold thoroughly wet with tears. As his ass got spanked again, he felt reminded that the worst part was still ahead.
As if the Master had read his victim's mind, the butt plug was pulled out with a quick motion, sending Sean's sphincter screaming for mercy, hot anal pain consuming his attention.
Both rough hands wrapped around the teen's slim neck from behind and held on. He could clearly perceive the dick lined up with his ass, but was unable to relax to allow it entry.
The hands squeezed. Sean's vision filled with white dancing dots while the blood rushing in his ears swelled to deafening volumes. Just when he thought he was going to fall unconscious, just as his waking self left his mind – the hands released him.
He was shocked back into his body as the dick drove into his now loosened hole. The little lube the plug had left barely kept his insides from being torn to bleeding bits.
Sean yelled on top of his lungs as the massive dry dick slid in as far as it would go. And then further, pushing past the complexities and intricacies of his guts with force as if steamrolling an unruly pathway.
The boy's anal virginity was ripped from him as every fiber of his being focused on the agony inside his rear end.
Master Red Shoes pulled out, prompting mumbled gratitude from the sobbing mess on the sawhorse. The man walked around, pinching his way up the victim's spine and tugging on the nipple clamps.
Once positioned back at Sean's face a tight grip forced the boy's head up until the thin back was strained in the strongest arch the bound limbs allowed.
The boy was getting orally assaulted once more, the man's dick rubbing every spot in the small, stretched mouth, from the cheeks to the tongue to the palate. At least he wasn't gagging Sean this time as the boy gratefully noticed. It seemed he was picking up saliva.
He let go of Sean's jaw and dropped the boy's head back on the leather, slapping his face left and right. He walked around back to the rear and pushed in.
This time he reached forward and pulled both clothespins off at once. The pain overdose from back and front made Sean cry out again but this time Master pressed his hand over the opened mouth.
Pushing in and pulling out came to a quick rhythm. One hand rested in the small of Sean's back. The other hand was grabbing his hair to keep him pressed down.
After a minute of getting used to the intense feeling of a dick in his ass, the fucking made little Sean see swirling, psychedelic images with his blind eyes. He had trouble controlling his breath. This was not the gentle, loving way he had intended to lose his virginity. He should have asked more questions before agreeing.
Ten hard thrusts later the fuck slowed down as Red Shoes focused more on delivering pain into Sean's nipples, pulling his hair and slapping his aching, open-mouthed face from behind.
Master grabbed the boy's balls with his fist and squeezed, pressing the boy's dick into the sawhorse's wood. Sean shivered from the burning that crawled up his stomach as his balls were tormented. But the pressure was too much. Denied of an orgasm, he felt his cum shoot from his hurting penis, making the dick pulse against the wood.
With a muffled swear, Red Shoes jumped back, letting go of his victim's sack and pulling out simultaneously. Sean heard the rustling of paper on the floor – no, on shoes. He had soiled the Master's footwear with his cum.
But the cleaning didn't take more than a few seconds before the boy's ass was used again. Cuming had given Sean very little relieve. Now his dick was more sensitive as it rubbed on the wood with every thrust.
The humping grew faster, shoving the entire sawhorse with its mounted victim farther into the room, closer to the hotly burning lights. Master's groans took on a more pressed and uncontrolled quality, as he slammed his hands down on the helpless boy's back, ass and head.
One last time, Red Shoe's hips slammed into the glowing red bubble butt he was using. Then he trembled on the spot, holding the boy's hips with a tight grip, balls deep inside the snug hole.
Sean could clearly feel several shots going off inside him, hot juice filling him up.
With a few slaps on the back, the man pulled out slowly. Sean clenched his sphincter, keeping the cum inside, not wanting to soil his violator's shoes again.
Now alone again, the teen wasn't moaning anymore, listening closely to the man's steps and fast breath, interrupted only by his post-orgasm moans, seemingly enjoying the bound boy's presence still.
Eventually, the Master calmed his breathing. He detached the spider gag from Sean's jaw and stepped back, possibly admiring the view. The boy closed his mouth, experiencing incredible relive in his cheeks and jaw. He sighed loudly, hoping his violator would understand. He figured the man didn't like his boys to talk.
After a time long enough to make the teen worry he was going to stay there for yet more of the same, Red Shoes squatted down next to the boy and undid the shackles that tied him to the sawhorse. In doing so he caressed the ass and legs of his victim gently, carefully. Sean held perfectly still, afraid that it was all a trap and he was in for more.
Sean heard the D-rings click and was pulled up by his hair. He detached from the leather with a slurping noise, the material sticking to his sweaty skin. His back hurt from having been rested on the surface for so long.
The Master dragged him away from his torture device, still blindfolded. Walking was difficult with an ass this sore, but the Master didn't ease him into it. Sean stumbled along.
Something got pressed in his hand – his phone. Then a door opened and the boy felt the cool air from outside on his dry sweat covered skin.
Master's rough hands tore the leather bands from Sean's wrists and ankles. Then the door closed. Nothing happened.
The boy stood on the spot for a few seconds, trying to calm down and figuring out his next steps.
Eventually he took the blindfold off. It was twilight now, but he was still a bit overwhelmed from the first light he saw in a while. It wasn't cold, but he trembled – still a bit in shock from the entire event.
He was completely naked, outside the warehouse.
Looking at his phone he saw that Master Red Shoes had deleted his own contact. Sean had no choice but to make his way home in the nude. His dick rose at the idea.
With shaky legs the boy walked down the side alley and peaked around the corner into the main road. The park was empty, but cars drove along the streets in irregular intervals. Going through the park was his best bet.
As the night fell over the city, the naked little boy dashed across the street the second there was no car in sight. Just when he had reached the other side, headlights fell on his back. He rushed forward into the park without looking back. They would never know whose backside they had just seen.
Sean didn't dare to stay on the path. Instead he dashed into the bushes that grew along it. In the coming dark of night, even the potential stray jogger would probably look right past him.
The grass was dry and hard, not softening the dusty ground much. One hand covering his crotch, the other holding the phone, the slim, sexed up teen was getting quite excited. He couldn't help but imagine being seen like this. He wondered how obvious it was that he had just been completely sexually destroyed.
His dick was hardening just a bit while he fantasized, now finally knowing about the pain and fear the real thing had made him experience.
At the end of the park, things got tricky. There were no more bushes to hide in and the streetlamps were on. He tried to think of the best path home, but the way he had come was simply the quickest one back as well.
The lights reflected off his tan skin, giving every lean muscle fiber a defining shadow. He stepped timidly onto the empty road, illuminated by closed shops and very few apartments farther up.
There was no other option. Sean ran. His naked feet hit the asphalt, echoing in the quiet part of town. He rushed past the library.
Suddenly doors opened to his left – a bar. Three men stumbled out, saws him and froze. So did Sean, like a deer in the headlights. Then he ran. The men hurled slurs after him, but he could only hear his heart shooting blood in his head. They didn't follow him.
He only had to make it around a corner and would be at the cinema. The chances of a movie ending right when he walked by were minuscule.
A movie ended as he walked by. Twenty people flooded the street, and spotted him immediately. He held both hands and his phone in front of his crotch and ran right through the crowd, eyes on the street.
Sean was met with cries of disgust, insults and whistling. He heard phone cameras go off. Hoping nobody who knew him was there, he kept running without looking back.
The people were almost behind him, with every eye now focused on his slender frame that would normally melt into the crowd. The boy stumbled over a traffic cone. His phone slid from his grip and landed in a patch of grass – mercifully still intact – forcing the boy to stop. He caught himself by reaching out, frozen in place.
His legs were spread and his ass out. Sean touched the asphalt with his flat hands, arms straight out. He was presenting his hole. As the clicking of cameras intensified – and the insults became more specific – Sean felt a thick drop of cum run out of his ass.
He jumped up, grabbed the phone and ran off. Again nobody followed him.
Sean's ears rang from the shouts. He had been called a pervert, a faggot, an assfucked cumwhore and things he didn't even fully comprehend. On a certain level, he supposed they were right. In any case, it didn't help get the boner down.
Two empty streets farther, he allowed himself to slow to a less exhausting pace. Sean looked around and found himself solitary at last. There were only four more streets to go. He could basically smell his room already. The shower was calling his name.
Seeing the headlights of a car from the side of the street the teen hopped behind an advertising pillar, waiting for it to pass. He was pressed against the cool metal, feeling his own heartbeat.
His pulse pumped through his semi hard dick. The gentlest touch by a brush of his hand brought it to life. With no car in sight, Sean rushed across the street and out of the illumination radius, vanishing in the dark between the family homes.
He was getting fully hard and absentmindedly jerked off, his hand already at his crotch, trying to cover the throbbing erection.
Night had fallen and the houses around had the lights on inside. As long as Sean stayed out of the direct light-cones that fell on the street, he assumed himself basically invisible.
Making it two streets farther with no incident, the boy was now furiously masturbating while he walked. He hadn't had a proper orgasm during his abuse by a stranger minutes ago and desperately needed relief.
The town hall came in sight. There was some kind of party going on inside and out in front. Sean spotted mostly teens, many of whom he knew from school. He ducked into the bushes at a safe distance. Going a different way was not quite easily possible, but he could sneak around the back with no problem.
Bushes and half assembled scaffolding hid him from the party-goers while allowing him to use the light from inside to find his way along the trail.
One hand still stroking his solid dick, Sean looked at the time on his phone. It took just a glance for the naked teen to become distracted by a notification and soon he was scrolling through his social media. Apparently many popular kids form his school were at this party going on mere feet beside him.
His foot hit an empty beer can. There was a whole pile of them on the ground, amidst cigarette ends. A flight of concrete stairs led to an emergency exit.
With his orgasm approaching, Sean sat down on the stairs, expecting to get the hardest, most mind-numbing, most leg-jellifying orgasm he had ever had. Carefully, he dropped the phone beside him.
His thoughts wandered back to the sawhorse, the spider gag and the intense feeling of helplessness. But what he thought about most was the enormous dick. The feeling of getting ravaged was still vivid in his head.
As he got closer and closer, his limbs began to shake, out of rhythm with his rapid breath.
The emergency exit burst open. Bright light spilled out onto the stairs, blinding the little boy who whipped around wildly, facing the emerging party guests.
He let go of his dick, covering up with both hands. But it was too late – he had another ruined orgasm. His right leg spasmed uncontrollably as he shot a streak of cum up his stomach. It stuck to his chest and ran back down. The next few streaks were less intense, only squirting out of his dick an inch far before splashing onto him.
"Ew what are you perverted fag doing?"
Sean wanted to run, but his phone was still laying on the stairs. He had to bend down to grab it. As he bent over sideways the last of Red Shoes cum dripped from his ass.
The party kids were all shouting over each other. "Holy fuck, this cocksucker just shot jizz from his ass." "Disgusting pervert." "Did you just get fucked, whore boy?" "That's it, I'm calling the police."
The fearfully shivering teen didn't recognize any of the boys and girls by voice. If he ran they might not get an accurate description of him and he could deny everything.
"Wait," said a vaguely familiar, deep voice. It was one of the football players from Sean's class. "I know that kid. Fuck, you are getting wrecked tomorrow at school. Your life is fucking over, pervert."
Sean ran. He didn't look back, ignoring the shouts that followed him. His semi-hard dick was slapping painfully against his sticky abs. The burning in his throat increased as he ran out of breath and developed stiches in the side.
It only took a mere minute before he arrived at his house. Finally, the night didn't have any more surprises for him in store.
At last, at home. Sean took the keys from under the flowerpot by the door and let himself in. He was safe now.
It seemed that no one was home. His dad's work clothes were on the floor in a pile, so he was probably locked into the home office again.
Sean was about to rush upstairs to take a shower, but figured he should grab some fresh clothes from the washroom. Mum always left the washed clothes there for every family member to fold their own.
The boy hopped into the washroom. His eyes caught a glance of something in the corner. He turned his head, fell to his knees and retched as a realization overcame his tormented mind.
In the corner, next to his dad's work boots was another pair of shoes.
Brand new, shining red running shoes. His dad's size. The residue of a hastily wiped away streak of cum across them.
This concludes the story of Sean. Bet you didn't expect that twist, huh?
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