The Boy and the Skipper

by GayBlade90

2 Oct 2023 1108 readers Score 8.7 (17 votes) PDF Mobi ePub Txt


“I’m home” yelled out Max

”Well you certainly took your time didn’t you.” His father said in a low but stern voice

”I’m sorry the store was closed and I had to get fishes from one of the vendors.. the fisherman. I didn’t have to pay….” He said as Max rummaged in my shorts the soaked and wrinkled bill.

His dad stood there staring at his son explained and held out his hand for the cash.

”What happened to your clothes and your shoes?” His dad said

”I accidentally fell in the water and they pulled me out and uh I lost my flip flops.” Max said

His dad wasn’t pleased crossing his arm and tapping his narrow foot in his shoe. I curled my toes a bit and put one foot over the other.

”And you don’t have any other pairs of flip flops.” His dad said

”you’ll have to wait until school is about to start for a new pair of shoes, money is tight boy.” His dad said as he rested one foot on the stool. He drops a piece of metal he was using to tighten something.

“Don’t worry dad, my feet are tough and I like walking around barefoot anyway during summer.” Max said as he picked up the piece of metal from the floor with his monkey toes.

“See dad, strong and useful. “ Max says 

His dad grabs that metal from his sons feet and sighs.

”Well I guess, but don’t lose your clothes boy, maybe you can get summer job to pay for new shoes.” His dad said

Max agreed and said he would look for one every day. But secretly he would just try and hook up with skipper. He jerked off in his room again thinking of his encounter with skipper. He dreamed that he was a merman captured in a net and Skipper falls in love with him. Jumping in the water and the two fuck underwater, 1/2-fish 1/2 human fucking a human.

The following day Max’s dad was taking his boat out on the water. He was gonna go into the next town on the island nearby. He walked up to where he was with his boat and gave him a sandwich to take. Max felt great walking on the dirt in my bare feet. His Dad was there and watching him walk up.

”Don’t hurt your foot boy. His dad said

”Don’t worry dad they’re strong and it feels good walking barefoot.” Max said

Max’s dad had quite a few pairs of shoes, mostly casual slip ons, canvas deck shoes. Usually wears them while fishing or going out and about. He wears espadrilles in the house like slippers. He didn’t offer for his son to borrow his shoes because Max’s feet are too big to fit in them. And he doesn’t like to share them, he’s usually buys Max a pair of shoes and one pair of flip flops. 

“Bye dad” max said

Max quickly when to the dock walking barefoot, by now his feet were getting black. The skipper was there waving. They kissed and one of Max’s toes was lifted and rested on the skippers white shoes leaving a dirt mark.

”it’s nice that you’re barefoot but We need to clean you up boy.” Skipper said he used the hose to wash Max’s feet, and Max used a sponge to wipe the dirt off.

Skipper wanted nice clean feet on his boat. Skipper was dressed nice. A nice shirt, navy shorts and white canvas slip ons. Max got down on my knees to offer to clean them. The boy got shirtless to turn him and the older man on. He Grabbed a little cloth and wiped the dirt off his shoe.

”Good boy “ said skipper “

“yes sir.” Max said and he licked the tip of the skipper’s shoe with his tongue. Now he stood up hard. Skipper stared at the boy’s large feet. He wanted those feet.

The skipper grabbed the boys cock hard when he wasn’t looking. And pulled on it. He put the boy to work and clean everywhere. Setting up everything for Sail they would be out all day.

As they set off, Max loved the feeling at being at sea. Max stood next to Skipper as he was holding the wheel. Skipper was stroking Max’s cock.

“Take the wheel.” Skipper said

Max did so nervously. As he grabbed the wheel Skipper got behind him, digging his two shoes into the back of Max’s heel and then used his shoes to spread Max’s feet apart. Skipper was holding on to Max from behind putting his right hand into his shorts and grabbing his dick and balls. His other hand was touching the boy’s chest and periodically pinching his nipple.

”ufff ahhh.” Max moaned

”where are we headed boy?” Skipper asked as he gripped Max’s dick hard.

”Where headed northeast sir.” Max said

Skipper grabbed his dick harder pulling and pinching his nipple

”wrong answer, don’t use your head!” Skipper said

”owww, where headed south sir…” Max uttered

”Speak up Boy!” Yelled Skipper as he yanked on Max’s dick harder and grabbing balls.

”we’re headed south sir!!” Max yells

”Great” said Skipper

He brought the boy’s shorts down and exposed his bare ass. He spit in the boy’s butt crack and began to run his tongue there, Max was feeling so turned on, he was on his tippy toes as this happened.

Skipper was rimming this boy so good. He then washed his mouth a bit, spit into a bucket and told the boy to stop the boat and drop anchor.

Skipper got on his knees and began to suck the huge cock of his young first mate. Out in the open sea with the salty sea air everywhere. The sounds of waves crashing and the sucking and popping sound the skipper makes while sucking cock.

Now Skipper got Max to get on the floor, Skipper sat down, their legs in front of the other. skippers shoes landing on Max’s chest and puts his hands on them caressing the older man’s shoed feet. They sat like scissor sisters but Skipper was grabbing the boy’s left foot and put it to his mouth. He kissed the toes, licked them, sucked them.

”I love your feet boy, they’re so manly and big.” He said 

“That’s why I wanted them clean.” He continued 

“I love that you love them sir.” Max said

Skipper’s bender leg then lands his shoe near the boys dick,

”I love the shoes you’re wearing sir, I love all your shoes.” Max said

”oh yeah… “ said Skipper, he put his shoe on my balls and then stepped on my dick a bit stroking it. 

“You like that boy”said Skipper

”uff yeah” said Max

Max loved feeling the ribbed rubber soles of his thin shoes. And then the canvas of the upper instep. He could see Skippers toes flexing through the shoe fabric. The other shoe went into Max’s face as if to step on him playfully.

The boys cock was fully erect and needed to go in something.

“Fuck me boy.” Said Skipper

”Yes sir” Max said

He went in slowly using a lubricant from skippers pocket . He dropped his pants and stepped out of them. Max told him to keep his shoes on. He had this huge fetish for them. As Max entered Skipper moans and moans. Max’s feet step closer, Skipper lifts his heels and then steps down on Max’s toes. 

Max felt his toes being crushed by the older man’s shoes and it gave him even more ecstasy and he went all the way with Skipper. They fucked for a while standing up. Then doggy style for a little while.

While fucking doggy, Max put his left bare foot on Skippers head, Skipper loved it. They then tried missionary, Skipper had his shoes on my shoulders as he was fucking. Skipper ended up Cuming from his ass a few times. He would shake. The boy still had some left and skipper said to cum on his face and chest.

Skippers legs came down and the tips of his shoes were on top of Max’s feet a bit and he stepped down on them. 

“Fuuuuckkkk” max said

He shot five loads all over Skipper’s head and chest. He kissed him in the lips after wiping the cum off a bit.

”Woooo.” Said Skipper

”You fuck so good, you’re one of the best I’ve ever had.” He continued 

It was so late. They lost track of time, they started to sail back, the rest of the way back was great and they started fishing and cuddling the rest of the afternoon.

Max had to tell his dad later that he couldn’t get a job unless he asked slipper to be hired officially.

”can I work on this boat permanently, as your first mate, but for real like a real job.”

to be continued…

by GayBlade90

Email: [email protected]

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