The Boy and the Skipper

 After graduating high school, young Max was now free to enjoy his summer before going to college. He thought about getting a part time but thought to himself he would rather enjoy and relax. Max was hiding the fact that he was gay, he was pretty lean, six pack, with dark blonde hair and blue eyes. He stood around 6 feet tall, with a nice voice. Max had a fetish for men in shoes, and another thing that made him hard is whenever he would be in public in sandals or barefoot. He felt free and horny showing off his size 13 feet. 
 

Max was asked by his father to run an errand to grab some fish from the market. It was so hot that day that Max threw on his dark green swim trunks going freeballing. He put on a grey tank top and some flip flops. They lived near the bay of the city and connected to that is the freeway to the beach. In the Bay Area there were boaters who came in to sell their fish and bring it to the market. As Max went to the market some fisherman just finished dropping off their catches. Max rest a bare foot in his cart now. Some of them notice his feet.

 Max seemed turned on by some of these salty men, ‘must be nice to be on the boat all day’ just fishing and making money like that. While day dreaming Max bumps into someone, the head of one of the fishermen hits his collarbone and Max loses his balance and slips on a fish that fell to the floor and now his other sandal flies off and he falls face forward.

“Arrghhh” Max groans

“Woah, are you alright boy?!.” A low gruff voice said

Max turn over in his stomach and looks up, in front of him are a beat up pair of White canvas boat shoes. The kind fisherman wore back in the 50’s or 60’s or so. They were white but faded to an off white, those shoes had seen better days. Spots of oil on them too, but for some reason Max got a hard on while he was down there. The man then walked around grabbed his flip flops which had slid off his feet.

“Are you alright boy? Can’t you get up?” The voice said, his shoe went to nudge Max’s now bare foot. 

“I’m alright, I’m up.” Max uttered

Max stood up and the man who bumped him was looking up at him. He was an older man, looking like his dad’s age, he was in shape for an older dude. He was around 5’7 so a bit shorter but had broad shoulders and muscles. His legs look like the were strong, big calf muscles. He wore a tank top, worn khakis and his old white shoes. He also wore sunglasses. His hair was slicked back with some grey and he had a mustache.

“Well glad to hear it boy, here you go.” He said as he handed Max his sandals. He noticed the man looked at the boy’s worn flip flops and it’s footprint and toe marks. The man looked like he got erect. 

Max realized that he had a hard on too, and everyone saw it, since he was freeballing it showed more through his thin swim shorts. He was a good 8.5 inches erect. Everyone was staring and one lady giggled. But the man did not he didn’t smile. As the man inched closer his shoes nearly kissing Max’s toes.

 Max felt the cool floor under his bare feet and wished he could turn into water and melt down, he was embarrassed, too embarrassed to grab the fish.

He put on his flip flops and got outta there. He looks back and sees the man he bumped into walking outside and it seems like he stopped to look at Max.

Max went home empty handed and he caught hell. He tried explaining what happened but now there was no dinner, Max was told to find a way to get those fish or else his dad would give him a reason to be embarrassed.

Max was trying to make his way to the fish market and saw it was closed. It closed at 5pm and it was 5:04pm. The employees inside kept giving him the ‘we are closed’ hand signals. As Max walked towards the boat areas the captains are cleaning their boats. 

He realized each captain had a younger guy helping. The young ones were in swim trunks, some shirtless but all of them barefoot . He got hard seeing the older captains however, they all had shoes.

Max got harder thinking how young guys should go around barefoot in summer, and how older men should only be the ones to wear shoes. Max was tempted to take his own sandals off to feel the earth beneath his feet. He takes them off to feel the ground, when he hears a familiar voice.

“Hey kid, how’s  it going” said the man from the market earlier. He was cleaning the fish that he had brought before.

“Hey..” Max said shyly “ not much just looking for fish for dinner”

“Well too bad the market closed, it didn’t give me time to clean up the fish I spilled” he said

“That was my fault.. I should of watched where I was going” Max said as he twiddled his thumbs. 

“No worries son, accidents happen.” He said as he began to grab a hose to clean the outside of the boat. His boat was pretty old, made of wood, unlike the others around.

“Now I gotta put these bad boys in the freezer, since I couldn’t sell em in time” the man said

Max lit up and pleaded if he could have some fish and pay him.

“I don’t know boy, you messed me up today, and you want me to help you out.” The man said 

The man started walking to the back of the boat, the sounds of his light footsteps stepping on the wood indicating the man was in the same shoes probably as stepped down off the boat and walked up to Max, he sees the same white shoes, getting him horny. Max felt horny and a bit naked being barefoot in front of this man. He felt a bit shy though. The man kept looking at his feet a few times.

“I tell you what, help me out cleaning up here and I’ll give you them no charge.” He said

Max agreed to work a bit and get the fish, asking if it would take long. The man said if he hurried it would be quick.

“I’m James, but just call me Skipper while you’re aboard.” He said sternly 

“I’m Max, I guess you can call me first mate …?” Max said

“ Haaa!” Said Skipper 

“ you’re too inexperienced to be first mate, you gotta get your sea legs first.” He said as he gently tapped Max’s calves with his shoe.

“Alright boy, cmon aboard.” Skipper said he then stops a sec...

“ But before that you take those off.” He said pointing to Max’s feet

“My sandals, alright” Max said

Max left them on the dock, and he was pulled into the boat by Skipper. It felt good being on the boat but he had a balance issue at first. Max doesn’t get sea sick so he can handle being on the water.

Skipper told Max he can take his shirt off if he doesn’t want it to get dirty. He said the shorts have to stay on though as he laughed. Unless “ we were out at sea alone hahaha.” 

Max gets horny again after hearing that joke. He took his shirt off and his lean muscles body was glistening with sweat as he cleaned. Skipper said he was getting older and needed help, so Max was on his knees scrubbing nearly naked. He felt a bit free, he loved being barefoot in summer even as a young boy. It made him horny being nearly naked with his dick nearly peaking from his swim trunks. And hornier that the older guy is there watching. 

Skipper was still in his clothes while cleaning up, his shirt, shorts and shoes. Max felt that young boys are normally not supposed to wear much clothing in the summer, especially shoes. Older men usually wore shoes all the time, just like his dad while Max was growing up. 

They also climbed up the mast to tie up the sails. Max was afraid but Skipper helped him go up as they moved up together face to face. Skipper would use his shoe to tap on the sole of the boy’s foot to move up him up. Max felt uneasy on the rope, the rope was too thin for his big bare feet. If he felt like losing balance, Skipper would let Max rest his feet on top of his. Max felt hard now, feeling the soft canvas uber his feet. He could feel Skippers own feet through the shoes. The small shoes disappeared under Max’s huge size 13s. He feels Skipper lift his toes when it’s time to move.

After finishing cleaning up the boat, Skipper and Max walked together around the boat inspecting. The boy felt his dick harder as Skipper got closer on his left side to put his arm around his shoulders. Max felt so tall next to Skipper but still felt like a boy with his dad, especially as he was looking down seeing his big beautiful bare feet walking side by side with Skipper wearing his white shoes. Max couldn’t help but notice how at times Skipper’s shoes would accidentally brush his toes and even stepped on them.

As they stood there Max’s hard on was too hard for Skipper not to notice. But he didn’t say anything. Max looks down and sees his huge size 13 foot and to his left Skipper in his old white shoes. They were smaller, looked like size 7.5 or 8. My left foot crept close to his right shoe as we talked and the difference in size was hot. Skipper faced me saying he owed me a beer. They say across from each other as Skipper and Max rest a leg on across their knee. 

He gave Max a beer, and they both started drinking. Skipper had his shoe moving on his lap as he sat and talked giving Max a hard on. Max, also moving his foot and holding it while taking. He wiggles the toes of his foot on the floor. Skipper is also tapping his other foot on the floor lightly and Max feels the vibrations, wishing his feet were getting stepped on by the older man. He moves closer, the foot on his lap inches closer. 

Max’s toes nearly touched Skipper’s shoe, but he moved it to the floor and sitting across you can see the sole of skipper’s shoe and how Max wished he could be under it and be trampled or clean it.

They both crossed legs as Skipper’s shoes  touch the boy’s feet and then felt a tingle. He wished he could use his toes to play with the laces of Skipper’s shoe, and feel the soft canvas, but he had to contain himself. Skipper rose up to get beer accidentally brushing Max’s feet in both trips. Max was harder in his shorts.

He stretched his legs up into the seat near Skipper and he can see the boy’s feet are dirty but he doesn’t mind as he stretches his own legs up. Skipper felt as though young boys should go around barefoot more often. A sign of youth, playing around while the mature men wore the shoes. It aroused him a bit. 

They finally finished drinking and Skipper offered a summer job to Max so he can help him on his boat. 

“ i need young strong legs” he said as hits the side of Max’s ankle with his shoe, Max nearly squirts out precum upon feeling the soft canvas and rubber sole of Skipper’s shoe on his bare ankle. 

Max tried to step forward but nearly tripped, he realized that Skipper had stepped on the back of his sandal. It’s almost as if Skipper was  in control, it felt hot to the boy and he agreed, and as they shook hands they both had hard ons. 

“See you tomorrow then?” Skipper said as he was still shaking his hand and then squeezed it hard, they both tried to squeeze to see who would win. 

Skipper kept squeezing hard and so did Max, but he began to squirm, his feet moving up and down. And that’s when Skipper right shoe steps forward and end up stepping on Max’s bare foot. 

Max moans from all of it, the hand pain, feeling almost naked, the handsome Skipper causing pain, his bare feet getting stepped on. Max’s reaches an orgasm just from all of that, he really had no control, he tried to hold the cum but the ecstasy was too much for the boy to handle. The white milk was concentrated in the cusp of his erect uncut penis, soaking the side of his shorts. His penis was erect upwards holding the cum.

Max pulled away as Skipper lets go and loses his balance, he trips on his sandals. He falls off the side of the dock, he had no time to react and was confused, he swallowed salt water. The next the he barely remembers is Skipper giving him mouth to mouth and compressions. Skipper was on his knees right above Max, and he sits back when Max regained consciousness. Skipper’s ass was on top of Max’s dick, and his dick got hard again, touching Skipper through soaked clothes. Skipper then turns around as they sit there ,and they fall back, Skipper on top of Max, they’re legs go in the air briefly. 

Max’s dick hard and pressing on the older man’s ass. Max realized he was naked. His shorts came off. Skipper had been drenched but he was glad Max was ok. Skipper ended up giving Max a hug saying goodbye for good, Max felt their cocks touching through the soaked fabric, both hard. Max was embarrassed to be naked but nobody around cared. The other boaters were happy he was ok. Despite his exposure Max felt great and a little frost and horny.

“I’ll understand if you wanna part ways here.” Said Skipper in a serious tone

“No worries, I still wanna be your apprentice.” Max said as he stood there with his 8.5 cock dangling and with open arms. Skipper was happy 

“Alrighty, boy!!!” He said as he smacked my ass to get moving, he was still in wet clothes, and his shoes made a swishing sound.

“I guess I gotta teach you balance and how to swim too.” Skipper said. Skipper then leans back and one of his shoes stand on Max’s foot and he pivots and does a roundhouse on the back of Max’s legs. Max nearly fell again.

“Uuffff…Yeah I’m just a young man who doesn’t have too much experience. Maybe you can teach me some stuff.” Max said in a whimpering tone

“ you’re not a young man here, you’re just a boy, inexperienced but I can teach you a lot, control, discipline, work ethic, how to stand firm and keep firm.” Skipper said 

On board again Skipper dries the boy off. And he quickly goes down below to get something. Now he comes back shirtless but with different shorts. He also brings out the fish and another pair of dry shorts that fit Max. Before Max gets dressed he goes to Skipper and hugs him. He is still naked, the boy’s erect cock now brushing the older man’s shorts.

“Wow boy! You sure are well endowed.” Skipper said and he turned Max to stand next to him and saw the erect penis. Max could see Skipper getting hard in his shorts. Skipper easily could have grabbed his dick, maybe he didn’t know that Max was already 18.

“Sorry about your swim trunks, but they are soiled anyway.” He said  

Max asks “ did I shit myself “

“No, you jizzed yourself, you got boy milk on your shorts and leg before you fell.” Skipper said

“Also some of the drops of semen landed on my shoes.” He said. Max looks down and sees Skipper in different shoes, some blue slip ons.

 His old white shoes to the side drying. There were a few stains on his shoes and Max offered to clean them, but Skipper said no because they’re old and he would wear a newer pair. Also it’ll be a little reminder of this day.

The sun sets down and Max grabs the fish, puts his sandals and shirt on. Skipper wants to walk Max home, he can’t wait for the next day. All the captain and crew wave. He then decides to take his sandals off for a minute and stretches his toes and feet on the ground. And the two walk by some nearby rocks by the shore. The boy felt free and frisky walking barefoot next to the espadrille wearing man.

Max’s feet was not used to the rocks yet and asked for his sandals and Skipper handed them to him.

They make their way back near the dock and Max feels like taking off his sandals for the walk home. As he does this some of the old captains put up an ok hand signal. Skipper also seems to be getting hard. Max and Skipper walk off, and the barefoot boy is feeling horny again. His feet next to the shoes of the older daddy, gets them both hard ons. Max noticed how Skipper is looking down at the his big feet. He was walking while kicking his feet out in front and every now and then his shoe would brush and kick against his foot or ankle, maybe on purpose. 

Max was filling up with cum again but he was making sure he didn’t explode with cum until he gets home.