Sailor Boy

Hi all, this one is a little different, a gay male story in which Tim's girlfriend makes a deal on his behalf to give sexual favours to a tall, older man in exchange for sailing them to a private party. Unfortunately, things get out of hand when his girlfriend isn't watching....

Hope you all enjoy! -- TSG123 x

-

"Let me lick your asshole."

"WHOA... no WAY!"

The fresh sea-air was cool on Tim's forehead, and up until that moment the golden Mallorca coast had seemed almost heavenly. Thin, gentle lips stared up at the older man in disgust.

The man sighed, resting a large hand on the side of a sleek, but faded white sailboat.

"It'll only be for a few minutes, and it won't matter because obviously you're not gay."

He had handsome, craggy features, a clean-shaven face, and the slightest hint of a gut, although any fat he did have was more than matched by his muscle. All of these plus humorous green eyes placed him around forty-five, although he had the vigour of a man decades younger. One could have described him as dashing.

"Urm, how long will it take to get there? " chimed Lexy.

Typical. Tim's girlfriend remained hyper-focused on what she wanted, shaking her ponytail as long nails tap-tap-tapped on the solid steel railing of the ship.

"About fifteen minutes depending on how far down the coast they go."

"Urm, Lex.... did you not hear what he asked for?"

"Yeah?" she said, like it was obvious.

"So, you're cool with that??."

A fierce gaze surfaced from her perfectly made-up features.

"... YES Tim, this is the only way we're gonna sneak on that boat party, and I don't wanna miss it, DJ X8 only hosts these parties like, once a year. It's the whole reason we booked this holiday, now stop interrupting!!"

He watched, shifting back and forth on his heels as she continued talking with the stranger, discussing the details of how Tim was going to put out for him.

"So how long do you need?"

"Ten minutes should do it, but I want him clean and shiny for me."

"L-lexy!?"

"SHUT UP TIM! Sorry... B... bud was it?"

"Jud," he replied with a leisurely smile.

"Yeah, right... He'll be cleaned up."

"Then I'll see you both tonight."

Lexy flashed him a fake smile and strode away, not waiting for Tim to catch up.

He bustled after her, waiting til they were out if earshot as they wandered down the pier, through gorgeous yachts and luxury vessels, before attempting to remonstrate.

"Lexy.... you can't be seri-."

When she set her eyes on him, they were snake-like.

"I don't want to hear a single word out of you... hell I'll suck him off and go to the party myself if I have to... You know I'm actually doing you a favour by not allowing another man to touch me??"

Her face morphed into a teary pout.

"You're gonna do this for me, right??"

Tim's head bowed, crossing his arms tight against his chest.

"... I guess..."

***

" You look stunning."

"Thanks," said Lexy, bringing her hand up the slim white dress she had painstakingly chosen over the course of two hours.

"I wasn't talking to you."

Her face became a grouse, then she shrugged as Jud positively drank in the sight of Tim's lithe frame stepping after her onto his boat, snug in a black suit and white tie. His hair was placed into a fringe which came down across one of his grey eyes, which seemed to be trying its best to remain hidden behind the dark brown curtain.

It was the polar opposite of the seaman's easy attire, shorts and a loose white vest, and they both took a moment, Jud of pleasure and Tim of reluctance, to examine each other, before Lexy clicked her fingers.

"Can we get this bit over already?"

Jud chortled.

"All in good time!"

He sidled to the wheel and started up the motor.

"Uh, you said we wouldn't need that."

"I can cut it off when we get close," he replied, and Tim watched as the man's muscles flared, hoisting one of the ropes to keep the sail extra tight, locked away.

Under normal circumstances he might have been nervous about Jud attempting to steal his girlfriend away if he hadn't already been hitting on him.

Soon they were moving, and Lexy gripped the handrail as they began to set off towards the darkness, not looking back once at the coastal sunset as Tim stared wistfully.

"Beautiful isn't it," said Jud, casually adjusting the wheel.

"Yeah."

"You like nature?"

Tim had no plans to converse with a guy who was preparing to lick his asshole, regardless of the man's appreciation of nature.

"Yep."

"You can call me captain if you like."

Tim kept watching the sunset, decidedly less appreciative of it with Jud forcing a conversation on him.

"No thanks," he replied tetchily.

"I'll let you wear a sailor's hat... I keep it in my quarters for naughty boys like you."

Tim trembled, clenching his fists, and moved to the prow of the boat.

Soon they had moved to a wild section of shoreline, far enough from humanity that the beach began to fade beneath the pink and orange hues of the overhead sky, a subtle wind bringing tangs of fresh salt with a hint of seaweed.

Tim managed to lose himself for a moment in it, before Lexy's shrill voice snapped him back to reality.

"Why are we here??"

Jud weighed the anchor, before moving towards the prow of the boat and coming close to Tim.

"To set the scene... Honestly, where's your sense of romance."

"Ew," said Lexy, who was watching them now with disgust, but also a vague sense of intrigue.

"Uh, can we... Can we go somewhere below deck," Tim muttered nervously.

"Nonsense," said Jud, resting a firm hand on his shoulder, which made Tim shiver.

"I think your lovely girlfriend should go below though; it might get a little raunchy."

Lexy rolled her eyes.

"Fine, whateveerrrr, but I'll be listening, the moment I go down there you have exactly ten minutes, understand?"

"Absolutely," he replied.

She took one last suspicious look, as if showing them she was suspicious would somehow keep Jud on an even keel, before disappearing below the deck.

Jud's hands instantly found Tim's waist, roughly undoing his belt.

"Hey, wait a sec... HEY!"

"You heard your girlfriend, we have ten minutes, which sadly means no time for foreplay."

He brushed Tim's crotch as he pulled down the young man's trousers, and the fleeting touch sent shivers down his spine.

"Bend over."

"Look, just... Just NO!!!"

Jud sighed, pausing.

"Well, I guess we better tell Lexy she's not getting to the party..."

Tim whimpered. Displeasing Lexy wasn't an option.

"Okay, okay... wait...! "

He closed his eyes, grimaced, and grabbed the railing, prostrating himself.

"Boxers down... And spread your cheeks."

Tim sniffled as he felt tears coming to his eyes.

"Relax Baby... You're not gay right? So this won't feel like anything... Just like shaking someone's hand."

Tim let out a high pitched chuckle which belied his nervousness.

"HAha uh, yeah.. right... right.. "

With that his boxers came down, and Tim felt the coolness of the coastal breeze caressing his ass.

Jud took a long look at the bubbly globes, and the flaccid 3-inch package on the other side, with an appropriately modest set of balls underneath it.

"Cute," he chuckled.

Tim's cheeks went red.

"Spread 'em."

Tim closed his eyes, praying for a miracle, a tidal wave, or some sort of mer-people to rescue him from his fate... But none appeared, and he cringingly wedged his fingers into his crack and pulled the cheeks taut at the speed of a snail.

The wind flicked his anus, and he shivered whilst exposing his flower to its maximum for Jud.

For a long time no-one spoke, Tim's anus flexing as he got used to this new, incredibly open position, Jud transfixed on his quivering, pink hole.

"Look, can... can we get on with it plEEAAAASSE!"

A long, rough tongue entered his crack and wiped from bottom to top in a millisecond.

Invasive didn't even cover it.

Tim let go of his ass.

"EHHHN, Okay n-no, no thanks I can't, this isn't..."

"It's this or we talk to Lexy!"

"But please, there must be some other wa-"

"Lexy!" Jud cooed, just quiet enough that she wouldn't actually hear it.

"FINE, G.. GODAMNIT FINE!!!"

He yanked his pillows again, wider this time, to the point where Jud could see the beginnings of his tender chute.

"Fuck," he sobbed.

"There it is..." whispered Jud, closing in to the point where Tim could feel his warm breath on his butt.

Jud was unable to resist any longer, and grabbed Tim by the legs, shoving his face into the open crevasse.

"HOOHHHHH!" moaned Tim as Jud began a nasty exploration of every inch of his exposed butthole, the roughness of his tongue alien to such a sensitive spot, making things he had never been aware of come alive. He was discovering that the lip of his butthole was quite pleasurable when pressured, and when Jud's tongue dug into him Tim let out a shuddered groan as something clicked, and all of a sudden he was struggling to remember how wrong this was as Jud plunged back and forth inside him, eating his ass like a champion.

"Mmmhhh, MMMMHHH,"

The suckling, humming sounds from Jud's mouth emanated through Tim's body, and Tim found himself swallowing unusual amounts of spittle as Jud plundered him, strong hands feeling up his legs and grabbing wodges of skin, bone and muscle, leaving Tim woozy as all of him became part of the carnal act, a canvas that Jud was less dancing across, more submerging within his grasp.

Tim gripped the rail so tight he thought his hands might end up fused to it, no longer sure if he wanted the sensations to stop as Jud began to fuck him with his tongue.

"Ahhh yeah..."

Tim's heart fell out of his chest as he registered what he had just said.

"Excuse me?" uttered Jud, coming up for air.

"Nothing, I said nothing!" shrieked Tim.

Jud dived back in, and a swashbuckling tongue-fuck put paid to his lies as Tim felt his whole body shake under the redoubled ministrations of Jud's muscular organ, penetrating fully now into his body.

"GUUUUHHH!" cried Tim as Jud flicked the tongue setting to full intensity, French kissing his asshole like it was their wedding day.

"Oh... HUHHH,"

His cock was rock hard, all 4 inches pulsing in anticipation. It was going to explode, and he needed it, he needed it more than he'd ever needed an orgasm in his life.

"Time's up guys!... EW, that is so gross...!! "

Lexy's piercing tones had never been less welcome as they were right at that moment, and Tim whined as Jud slipped his tongue from the rim immediately, right on the edge of the precipice.

"No!" he moaned, a moment of sheer incomprehension taking over as he grabbed his cock and attempted to masturbate himself to completion all over the railings, until he felt the cool evening air kiss his wet butthole again.

"Ohhh.... Shit," he moaned, hand snatched from his cock to tug his boxers and trousers up, still aching to feel Jud's tongue back inside him.

"Tim are... Are you hard?!?!"

"Huh?! N-No!" he stammered, zipping up his trousers, but his face told the true story.

"Wow... That is fucking... disgusting. I never would have let you do this if I knew you liked men.... Fuck, honestly, you're pathetic, you know that?"

Tim sagged, his shirt crumpled where Jud had been pulling it.

"I... I don't like men..."

"Just... Put your jacket on and don't talk," Lexy muttered as Jud let out a whistle and began busying himself with raising the anchor and preparing the sails.

Their host broke the awkward silence that ensued.

"Now this is going to be dangerous you two, as we'll be sailing in the dark, so it might be best to go below decks again until we reach the ship."

Lexy peeled her eyes suspiciously, before making her way back to the stairs, Tim sidling up behind her.

"Ah not you gorgeous, I'll need someone to steer whilst I adjust the sails," he said gesturing to Tim

"M... Me?" he whispered.

He had come so far out of his comfort zone today that he didn't know what to think, still a little woozy after their earlier actions.

"Yes, here... Take hold of the wheel..."

"Ugh, just let me know when we're there," snapped Lexy, "And DON'T do any of your gay bullshit," she hissed, Tim shrinking into nothing as she disappeared out of sight.

"Sure thing princess..." chuckled Jud after her, "here we go then Tim you'll be my little sailor boy for now, okay?... There's a cute little hat in it for you, if you do well."

His cheeky grin was not rescinded by Tim, the tall man jogging across to the sails and unfurling them as Tim clutched the wheel, more for support than anything else. Jud's saliva was still leaking between his ass cheeks, wetness soaking into his boxers and making him immensely uncomfortable.

Added to that was the fact that his erection was still quite hard, and only just beginning to go down. The sail came loose, and Tim watched as Jud hoisted the sail up, powerful arms and chest flexing underneath his t-shirt.

Tim's erection reversed its deflation, like a dog sensing a postman at the letterbox, excitement overflowing once more as it began to harden painfully again.

As the sail was catching the breeze, Jud sauntered over to Tim, flicking a switch which turned the boat lights on as he did so.

"We'll have to get used to being up here together whilst we still have light... So, here's how we're going to do this..."

Tim groused as Jud's hands closed around his, guiding them in slow movements left and right.

"That's it... You've got the touch. I should fetch that sailor's hat right now for you!"

A sparkle of pride bloomed within Tim' s breast.

"Thanks," he muttered.

Jud busied himself adjusting the sails, as the last hints of dusk disappeared, darkness swathing the world around them, the single lamp and stars their only companions as they sailed into the void.

"So... You like nature huh?"

"What?" said Tim.

"Nature. I see you looking out to sea, you watched the sunset... You were staring up at the sky..."

"Uh... Yeah, I like it. It's peaceful...... Lexy doesn't really care about it though, so..."

Jud gave a chuckle.

"Women... Honestly, more hassle than they're worth."

Tim was about to offer a retort, but Jud waved it away.

"I know, I know, you love each other, that's fine... But isn't it fun just being two guys, having fun together?"

"Depends on what they're doing," said Tim, his face immediately going red.

"Well, how about when we were enjoying ourselves earlier?"

Tim froze in an upright position, paralleling the full mast in his pants.

"I-I wasn't enjoying it!"

"Oh really?.... The way you squirmed between my fingers... Goodness boy I know for sure you'd be more than satisfied if you let me go further."

Tim salivated, even as he shot an odious look at his admirer.

"That's... That's enough."

Jud simply shrugged and busied himself with small adjustments of the boat as Tim tried not to glance in his direction, observing the man's physique. He was quite a specimen, and it only served to make Tim feel smaller in his presence.

"Ah... There it is!"

Tim peeled his eyes as Jud came to the wheel.

He could just about make out a tiny light blooming in the darkness.

"Let me."

Tim obediently backed away.

"No, stay close, put your hands on me."

"Huh, why?!"

"It's for safety, we'll be travelling without light."

Tim obediently placed his hands to the man's waist as he switched the lamp off, surrounding them in a muted black, relieved only by the stars and the blink of orange in the distance.

"Hold me tight."

He huffed and pushed himself so he was around Jud's waist like Rose and Jack from the titanic.

"Come on, don't be shy, push yourself against me."

"I'm fine."

"Well sure, but if you don't hold me tight, you might get thrown overboard by a swell, and you'd have to be lucky to get saved in the sea at midnight."

Tim grimaced... And pressed his crotch flush into Jud's strong tush, the older man breathing heavily as he felt the hard erection of his ward digging into his cheeks.

"Ohhhhh, good boy," he muttered, and Tim whined as he clung to the sailor, trying not to let himself be stimulated further by the feeling of the man's powerful body in his arms.

"You should hold further down... For more stability."

Tim obediently shifted his arms to the man's belly, feeling the possibility of hard abs underneath the puppy fat.

"A little lower than that."

Tim's hands slid, less willingly, inches lower to his belt line.

Tim prepared himself to say no as Jud inevitably asked to go lower, but Jud didn't, which was oddly annoying.

The glowing light in the distance grew, but slowly. It almost felt like Jud was taking his time, although obviously he didn't have control over the wind.

"You're.. Not going to ask me to go lower?" Tim said after a minute of silence.

Jud didn't respond.

The lights grew.

"Hey... Don't you want me to go lower?"

Nothing.

"Just... say something."

Jud didn't say a word, and anger burned in Tim's chest.

"Are you serious? Now you don't want to talk to me???"

He chuntered as the man remained stoic, adjusting the wheel here and there, but nothing more.

"Well, maybe I want to go lower!!" he shrieked, and Tim reached down and clutched the man's shorts, front and centre.

A huge cock and balls came into his hands, and Tim choked as he felt the sheer length and girth of the man steering the ship, covered only by the frayed material of his trunks.

"Holy fuck..."

Tim shivered as he held the monster catch in his hands, realising also that Jud would have felt his comparatively miniscule dick pulse against his ass.

It then turned out that Jud's beast was only semi-hard, Tim letting out a barely-audible whine as it began to grow, leaving him clutching a raging ten-inch monster in his hands.

Jud made sure to give no response to what was taking place below his waist, even though he was in heaven, loving the feeling of small hands carefully exploring his member as Tim adjusted his baby carrot, pressing it deeper against Jud's backside. The smaller figure probably didn't even realise he was doing it, but a slow rocking motion began, perhaps convincing himself it was because of the nonchalant waves lapping at the side of the boat.

They approached their target, Tim trying to understand Jud's pipe whilst burying his erection repeatedly in the safety of his captain's cheeks, and Jud couldn't help a murmur as Tim squeezed tighter, just a little.

"OHhhhh...."

Jud gripped the wheel for support as Tim kept his hands firmly on the front of his shorts, clinging to his package.

They approached like this, an embrace in the darkness, as if the absence of light somehow made what they were doing unreal, less distinct.

Tim's fingers began to apply themselves up and down, stroking the thick meat, wondering what the skin of Jud's penis felt like underneath the shorts, gripping it tight which brought another light wheeze from Jud, pulsing between his fingers.

Then the sounds of techno music broke the tension, echoing across the water, and Tim whipped his hands away, glad that the semi-darkness would conceal his rosy cheeks as they approached the lights of a mega-yacht upon which seemed to be a world-ending party, at least if the salvo of noise was anything to go by.

The ship's sides were ginormous, tall enough that they couldn't see anyone when they crept up to it. To Tim it felt more like they were sneaking onto a cruise liner than a private ship.

"Wow," he muttered, looking up at the behemoth above them, as his hands jittered, still yearning to be filled by the heaviness of that package once more.