Island fun
Max finally got the job that he wanted. He didn’t have to be home with his grouchy father all the time. It wasn’t so bad with his dad. He taught him to fish and they rowed on a boat a lot so it kept Max in decent shape. Max’s father was a muscular guy when he was younger.
Max didn’t wear any shoes that much growing up since he was out living by the sea anyway. His dad thought it was fine for his son to go barefoot 24/7 during the summers, he said the earth would give his son good energy.
His father however would often be the one to wear shoes, it signifies that he was the man and his son was the boy. This was especially apparent during punishments. He was a good father but stern, he raised his son singlehanded.
His father thought as Max grew older he should start wearing shoes but the boy still prefers going barefoot everywhere. It made him horny.
Max was gonna make the trek to his job barefoot.
“hey dad I’m going to work now.” He said
”alright, have a good day.” His dad said while he watched tv . His father still wore some espadrilles even while in the house. His father didn’t like showing his feet.
His dad looked at his barefoot son standing in front of him. Max’s colossal feet dwarfed his old man’s shoe.
The old man moved his foot closer and started tapping his shoe against his son’s bare ankle. He didn’t know where his son got such huge feet from. It made him mad to think his son may have a bigger shlong in his shorts.
“If you hurt your foot, don’t cry to me! I will put salt on any of your busted toes.” He shouted
Max’s dad looks at his son and sees him looking older now.
He walked towards the dock in bare feet and with a hard on in his shorts.
Skipper was waiting for me and he put Max straight to work. He had to work without a shirt While he worked with him. The old man loved to watch the sweat drip around the young man’s body. He especially loved his huge feet and often messed with them.
Over the next few weeks the boy’s body began to become more defined with all of the heavy lifting. It made Skipper extremely horny just from looking at him. They would travel sometimes on deserted islands and the old man would teach the boy about how to navigate jungles, start a fire, get coconuts by climbing the palm trees. The skipper climbed first and it was easy for him. When Max climbed up he slid too much and splintered his feet but he eventually made it. The boy fell once and the skipper helped him get up over and over. The boy’s hard dick pointed at him and the old man grabs it also and pulls him up by his dick to climb the trees again. Then he gives the kid head so he can feel like a man and have encouragement.
Sometimes they gave each other blowjobs in the jungle. They would play a game where they would pull on each other’s arm while standing on a fallen tree. Kinda like tug-o-war.
The first time they played the boy was losing, no mater how many times he tried , the Skipper was much stronger. One time the boy splintered his foot.
Another instance. The Skipper stepped forward and his shoe stepped down on top of the the young man’s foot. The boy lost and owed the skipper a blow job. But he ended hurting his foot bad. Skipper kindly wrapped it up for him. Skipper then gave Max the blowjob
The next few years passed by and Max was now older, working the summer job of being the Skipper’s first mate and his fuck buddy. Max was more muscular, and more handsome with each passing year.
One day the two of them decided to dock the boat and go in the little deserted island for a nice little stroll. As they made the trek Max felt his heart pounding and him walking in his bare feet next to the old man’s shoes drove him nuts and made him feel like a boy. Despite his height and muscle he liked to feel vulnerable sometimes.
“Perfect let’s climb up this rocky hill.” Skipper said
The boy holds Skipper over his head to practice resistance and get stronger. Then while walking in the tropical jungle barefoot he felt like a boy next to his daddy wearing shoes. He had many kinds of shoes and he usually liked white, especially if Max fucks Skipper, the white cum won’t leave as much of a visible stain.
***MAX’S POV ***
The hard rocks under my bare feet didn’t affect me as much as in the beginning. When I was starting out with Skipper, I would walk on rocks in bare feet and they would hurt. My feet would get cut up and once my dad had told me so. He would put salt on my cut feet if he saw blood. It was terrible.
Skipper walked in his shoes and had a backpack with more stuff like water, food but I also saw him pack an extra pair of shoes in case. I felt like a young man walking barefoot next to the Skipper’s shod feet. Anytime I got hurt he would help me out until my feet were tougher. He once tried to give me his espadrilles but they were too small and I decided I could handle being barefoot in the wild.
“ Look boy!! What a view!!” He said
I was literally crawling and plopped on the ground behind him. He stepped back and his shoe crushed my hand. Ouch! But Skipper kept on walking. My hand was hurting now, I got teary eyes, and got up to keep going. Skipper found a little spot by some trees.
“I want you boy, I want your ass. Have you ever had a finger in your ass.” He asked
“No” I said in a nervous voice
I shuffled my dirty feet in the dirt and felt blood going in my dick.
“Well boy I want to make love to you.” He said
He had started kissing me and we were making out full on. He was grabbing my dick and I was grabbing his. He then pulls my shorts down to start giving me head. He then forcefully pushes me down to give him a blowjob and I start sucking him. I am gagging, my reflux is too strong. Skipper pulls out a spray for oral sex. It numbs the back of the throat . It was a mint flavor, I spit it out after and started feeling better. I had his dick down my throat no problem. It was big enough where it touched the back of my throat.
Skipper pulls me out of my shorts and has me walking down towards the rocky park of the beach. It’s private. He pins me against a huge boulder and spreads my ass cheeks open and spits in there. He starts licking my asshole.
I felt a wave of excitement, I’ve never been rimmed before. I was moaning in pleasure as his dangerous tongue was working my anus. Then I feel something going in, something thing, oh shit it was his finger. It pushed in slowly. It felt like I was going to take a dump but backwards.
Skipper put two fingers in, and then three.
“Just relax boy.” He whispered
He then goes through the bad and gets out a small anal plug and spits on it. He inserts it in my ass and it feels great and he says to leaving it there. He started to jerk off my dick. We did a mutual jerk session. His right hand jerked my dick so good with fast and then slow patterns. I grabbed his dick with my left hand and started to jerk it. I use my right hand to pinch the Old man’s nipples.
He moans in Ecstasy as I’m doing this. We do this for a while, we make out and I feel the wet sand between my toes as the waves come in slowly. Skipper is still wearing shoes, his shoes are getting a bit wet.
“Just stand on my feet To keep them dry.” I tell him
He tippy toes on my feet, it doesn’t hurt as much since it just pushes my feet down in the sand a bit. I was insanely hard now.
“I wanna fuck you.” He said
Skipper was getting dominant, he turns me around and takes out the plug and lubricates his dick to put it in inside me. I felt so hard at first, I didn’t like the feeling, I was moaning and yelling but he Insisted it would feel good after. I waited for it to go all in and finally it did.
It was Amazing. He fucked me good, he had me step in the water while he stood behind me standing on a rock, this way he was elevated slightly because he was much shorter than me.
He then pulls out and pushes me in the sand and puts my ass up. He starts to fuck me while my face is in the sand. Ohh it felt good and humiliating. Then it gets more rough and he steps on my head. His shoe is on my cheek, I could smell the rubber from his sole and the sweat and salt from the canvas shoe that he always wears.
“Arghhh, uhhh , uffff,” I moan
The old man has years of experience doing this to young Boys, he thrusts in and out and makes me feel great. Despite my head getting stepped on I am in feeling pure pleasure.
“Ufff, daddy, you’ve opened my virgin hole.” I say
Skipper pulls out and has me relax a bit. I’m leaking out cum mixed with some blood. It looks like strawberry cream coming out. Skipper holds me tight and caresses my ass. We walk into the jungle a bit and explore. We reach a tree trunk and Skipper wants us to see who is stronger.
“Who ever gets pulled to the other side gets fucked.” He said
We pull on each other using the fallen tree, the old man is stronger. He uses only one hand and I’m using both. He grips his shoe on to the truck good. My bare foot however is sliding forward and I feel a splinter go into one of my toes.
I make a face of discomfort as more splinters go in the sole of my bare foot.
Skipper pulls me over with one hand and I’m stumbling into his arms. My splintered feet rest on his soft shoes. I feel my ass twitch, and my dick gets big. Skipper cups my dick and balls in his hand. And he whispered into my ear.
“I win boy.” He said
(As Usual he wins, after many times playing the game despite me getting bigger, he wins or maybe I let him win subconsciously. His shoes usually gripped the log better. My feet would grip but get splinters.)
I look down and my dick is popping out of the zipper of my shorts. Skipper lays me on my back onto the tree trunk we were just on. He gets ready for a second round.
His dick is lubed up with precum, he starts to make his way to my already opened up hole. He sticks it in and I feel my legs shake uncontrollably, he pounds my hole good and my legs and feet are in the air. I use my left hand to jerk my dick a bit.
I look up at the sweaty skipper, he is still wearing his button down shirt but he opened the buttons to get my fingers to pinch his nipple. He has his shorts slightly down and his shoes are on still. He puts one up close to my chest to balance as he lifts my ass a bit higher.
I’m moaning and sweating and ufff I’m cumming.
“I cumming sir!!!” I tell
I shot three huge loads far. They fly on my chest and some gets on my face and hair. It was one of my best cums that I’ve ever felt. My ass was tightening now ass I came. Skippers dick was nearly trapped in there.
The old man stared at my chest and face that was full of cum. He moans louder and shakes uncontrollably. The man starts to yell and thrust with each shot of cum coming out of him.
His dick shot four times up my ass. He bred my virgin hole so good.
Skipper pulls me up and we quickly walk. He gets my shorts on me and we get close to the shore where his boat was.
The boat was a bit away from shore. We had to wade in the water. I took off my shorts and allowed myself to empty the semen in my ass.
“Hey boy! Gimme a boost.” He said
I lifted him up and he stood on my shoulders and then got onto the boat, he stepped on top of my head while doing this. It got me horny again. Haha. But my ass has had enough I would be the one fucking next time.
Skipper pulls himself up and I try to grab his leg. I’m able to get my hands to the ledge of the ship. But the old man doesn’t help me up. He stands there looking down at me. He steps on my fingers and I can’t hold on.
“What are you doing?!” I yell
“Making you a man.” He says
I loose my grip and am able to use my other hand to grab on but he stomps on the one too.
He steps on my hand hard enough where I’m about to let go. The last thing I will remember is the sole of his shoe coming down hard on my head and kicking me backwards.
***End Max POV***
***Skipper POV***
The boy went falling into the water. My shoe ended up kicking his face and chin and it had his brain for sure rock a bit. It knocked him out and into the water.
The boy would drown now but I dove in to grab him and dragged him out. He was wearing nothing but shorts. I layed him in the sand.
“This is your ultimate test to be a man.” I said as he stood in front of the unconscious boy.
I left him some flint for fire, and a pocket knife and a hatchet.
If he can survive here, he would become a man. A man who can take on my legacy.
I swam back to my boat and was able to jump aboard without help. I would need to disappear from here and find a new island to set up shop because everyone will be looking for the both of us.
I can make up a story about a white squall striking us and sinking our boat.
End of this chapter
Will the boy survive on the island alone. How will he get off…
