The polished shoes of Daniel Whitaker clicked softly against the jet bridge floor as he boarded his first-class flight from Chicago to Nashville. At thirty-five, Daniel had grown used to the rituals of business travel: the brisk pace through security, the practiced smile for airline staff, the way first-class boarding felt less like luxury and more like armor before a trial.
He was a thirty-something Chicago attorney, lean at six feet, the kind of build that came from disciplined early-morning workouts, with shoulders cut sharp and muscles that pressed lightly against his tailored suits. He adored his wife, and the two children they were raising together, bringing him more joy than he ever thought possible.
His complexion was clear and fair, his jawline clean and firm, with a calm intensity in his gray-blue eyes. Their home in the suburbs had become a sanctuary, a place where routines felt safe and grounding. He had an easy grace about him and thrived in the steady rhythm of the life they had built. Yet, beneath the layers of contentment, there was a secret that rarely surfaced, that he’d never acted upon, that lived quietly in the back of his mind.
He knew this trip was different. Could change his life and the life of his family if he were successful. He wasn’t just flying in for any case—he was lead counsel on the kind of high-profile corporate trial that could shift his career overnight. His mind was focused on the importance of this trip, when he caught the eye of the man sitting in the cockpit.
He turned as Daniel passed. Danniel thought the pilot had a cocky grin on his face and eyes that lingered a heartbeat longer than they needed to but dismissed it as his imagination. Men had hit on him before. It comes with the territory when you’re a fit, good-looking guy, but this felt different.
Broad-shouldered, silver at the temples, uniform pressed to perfection. He looked to be in his fifties but carried himself with the grounded ease of someone utterly at home in the sky. His nameplate read Captain R. Maddox. When Daniel met his eyes—steady, blue, disarmingly direct—it felt less like an airline courtesy and more like being seen. This encounter was special. Daniel could tell. He could just feel it.
“Welcome aboard,” Maddox said, voice warm with a Nashville drawl that hinted at hospitality and authority in equal measure. “Heading down with us today?”
“Yes, sir,” Daniel nodded, the pilot smiled at being called sir.
“Daniel Whitaker,” he said, clearly embarrassed, reaching out to shake the pilot’s hand. Maddox squeezed his hand with strength and confidence, holding it a second or two too long, Daniel thought.
“Flying in for a trial,” Daniel added. Unsure why, but needing, for some reason, to try and impress the older man.
Maddox’s mouth curved, and he seemed to scrutinize the young lawyer, unnerving him. It’s almost as if the pilot could read his thoughts. “A lawyer,” he repeated, letting the word roll across his tongue with a sexy smile. “Figures. You’ve got that…sharp look about you.” The compliment made Daniel smile with pride, because it didn’t feel like a snipe against lawyers or a polite comment from a stranger. It felt more like a something someone who knew him intimately might say, maybe adding “son” at the end.
“Come on. Few minutes before pushback. Let me give you a peek at where the magic happens,” said the friendly pilot.
Before Daniel could respond, Maddox gestured him forward, into the cockpit. The space smelled of steel, leather, and faint jet fuel, alive with the quiet hum of electronics. The fronts of their bodies pressed against each other as Daniel passed into the tight space. The pilot seemed to push into Daniel more than make room, pressing their chests and crotches together. The captain’s hand brushed his arm as he guided him to the copilot’s seat. He explained dials and controls with the practiced pride of someone sharing his second home. The pilot’s hand, tightly around the yoke, as Daniel stared, moved his hand with a subtle movement, up and down, demonstrating the control. “Or was he?” thought Daniel, confused.
Keeping his eyes intensely on Daniel’s, the pilot rose from his seat, helping Daniel from his, closing the small distance between them in the narrow space. “Well, Counselor, you’ll be taken care of on this flight. I’ll see to it personally,” assured Maddox with his hand brushing the small of his back.
Daniel settled into his wide leather seat, as he heard Maddox tell the lead flight attendant, “Mr. Whitaker’s in our care tonight,” he drawled, making the phrase sound almost intimate, but Daniel thought he must be imagining that as well. People just doing their job, he thought.
The seatbelt sign hadn’t yet gone dark when Daniel felt the weight of the captain’s presence again. Not directly - Maddox was at the front, speaking with the attendants in low tones—but the ripple of his authority was obvious. One of the flight attendants approached Daniel’s row with a practiced smile, offering a glass of champagne before the tray tables were even stowed.
“Compliments of the captain,” she said softly.
Daniel raised the glass, catching Maddox’s glance from the galley. The captain didn’t smile this time, not fully. Just the faintest acknowledgment - a narrowing of eyes, the corner of his mouth tightening - as if they shared a secret.
Cruising altitude came with the usual hush of first class: quiet conversations, the muted clink of glassware, the steady thrum of engines beneath their feet. Maddox emerged once, making his way slowly through the cabin under the pretense of checking on the crew. His gaze lingered when he reached Daniel.
“Everything comfortable, Counselor?” he asked, stopping just long enough for the drawl to stretch around the title.
Daniel inclined his head, fingers brushing the stem of his glass. “Very. You run a tight ship.”
“Always do,” Maddox replied. His hand touched the top of Daniel’s seat, knuckles grazing the leather. “Can’t afford otherwise. Lives at stake. Trust at stake.” His eyes held Daniel’s, steady, until the silence between them thickened. “I think my stepsons might accuse me of the same thing – running a tight ship,” he added. Then, with the faintest lift of his brow, a slight brush to the back of Daniel’s neck, he moved on.
Daniel sighed and leaned back into the soft leather. The cabin noise swelled – doors closing, safety announcements – but beneath it, Daniel felt like a small amount of turbulence had already begun.
The plane took off flawlessly and reached a cruising altitude, turning off the fasten seat belt sign.
A chime sounded and then Maddox’s voice came over the intercom—low, smooth, threaded with a Nashville drawl that seemed to wrap itself around every passenger’s attention.
“Good evening, ladies and gentlemen. This is your captain speaking, Robert Maddox, and I’d like to welcome you aboard flight 237 with service from Chicago to Nashville. We’re looking at a smooth ride tonight—clear skies most of the way, cruising altitude of thirty-six thousand feet. Should be about an hour and forty minutes in the air, just long enough to settle in, have a drink, and let us do the work.”
A pause. Then, his tone shifted just slightly—less scripted, more personal, like a private aside.
“Now, I know you’ve all had your share of long days. Maybe your trip to Nashville is for pleasure or for challenging tasks in your work but consider this your chance to let go a little. My crew and I will take good care of you - you won’t have to lift a finger, except maybe to raise a glass.”
A soft chuckle carried through the speaker, warm and confident.
“From the flight deck, I can already see a fine night waiting for us in Nashville. We’ll get you there safely, and if I do my job right, you might even wish the flight lasted a little longer.”
Daniel drained the last of the champagne in two neat swallows, softening the edge of his thoughts, yet making every detail sharper, especially the awareness that Captain Maddox was just beyond that locked cockpit door. He couldn’t help but believe that Maddox’s comment about his sons was some sort of message for him.
A whiskey arrived, unasked for. “The captain suggested you might prefer something stronger,” the attendant murmured, almost conspiratorial. Daniel let himself smile, though his pulse ticked faster than the easy expression suggested.
90 minutes passed in an odd suspension—reading briefs without absorbing them, sipping slowly, eyes drifting toward the front of the plane every time he heard movement. He was apprehensive, nervous – which were not things he usually experienced. He got up and traveled the short distance to the bathroom in front. Locking the door, he splashed cold water on his face. Staring at himself in the mirror, as he dried his face, he decided these unusual emotions were about the tasks ahead and the importance of the next day’s trial.
Daniel returned to his seat, to the sound of Maddox’s voice over the intercom, wishing the passengers a pleasant evening in Nashville and instructing them to fasten their seatbelts and prepare for landing.
By the time wheels touched down in Nashville, Daniel’s head carried the glow of champagne and a stiff drink, steady but softened. He moved with the other first-class passengers down the jet bridge, the warm, damp air of a Tennessee night rushing in. He had wanted to find a way to thank Captain Maddox before deplaning, and though the cockpit door was open, it was clear that Maddox was busy with postflight routines.
Daniel collected his bag at baggage claim and stepped into the heavy, humid night. Travelers spilled into taxi lines, ride-shares flickered their headlights at the curb, and the whine of rolling suitcases tangled with voices in the air.
Daniel spotted him immediately.
The captain, cap tucked under his arm now, uniform jacket unbuttoned, leaning against a column as though waiting for someone. When their eyes met, it was obvious – the captain was waiting for him.
“Counselor,” Maddox inquired, pushing off the column. His smile wasn’t for the crowd. It was pointed, deliberate. “You got a ride to the city?”
Daniel hesitated. He could have lied, said yes, brushed it off. Instead, something reckless flickered to life, fed by whiskey and that look. “Not yet.”
‘Over here, then.” Maddox urged, his voice steady and low, moving to the curb where a black town car was idling. He opened the door with an easy gesture, as if it were the most natural thing in the world.
Daniel hesitated for only a moment before sliding inside. The leather was cool, the space dim and hushed after the chaos outside. Maddox gave their bags to the driver and climbed in beside him, close enough that Daniel could feel the faint brush of his shoulder as the door thudded shut. The driver’s partition was drawn, leaving them alone. Maddox leaned back in the seat and appraised the young lawyer.
“Didn’t take you for the town car type,” Daniel teased, breaking what he felt was an uncomfortable silence, his voice a little rough from the whiskey.
“Perk of seniority. Airline wants its captains rested and punctual. I just make sure the ride doesn’t go to waste.” His eyes shifted, catching Daniel’s profile in the passing glow of streetlights. “Besides—makes it easier to see someone gets where he needs to go.” He leaned closer, his voice smooth, measured, brushing the edge of Daniel’s composure. “What kind of business keeps a lawyer flying first class?”
“A trial,” Daniel managed, his throat dry, eyes locked on the smear of headlights and neon racing by. “High stakes. Corporate fraud.”
Maddox’s mouth curved, the faintest suggestion of a smile. “That must cause turbulence too. Different from mine but I guess everyone gets used to it—whether in the air, or in life. Either you learn to ride it out… or it eats you alive.” He stretches his arm and lays it on the back of Daniel’s seat.
“So, Daniel, my boy, let me ask you a question?” Maddox asked
“Sure thing, sir,” Daniel swallowed, pulse stuttering.
“Have you been flirting with me tonight?” Maddox teased with a big smile on his face.
“What, sir? Uhhhhhhh…” blurted out Daniel, clearly panicked. “Not really sure what you mean?” he added, too quickly, the words tumbling out like a defense.
Maddox’s tone softened, quiet but firm. “You don’t have to apologize for wanting something. There’s nothing wrong with it.” He let the silence hang for a moment, then added, “Least of all with me.”
Daniel’s chest tightened, the words seemed like a threat but also an invitation. He risked a glance sideways—and found Maddox watching him, steady, unflinching.
“The minute I saw you, Daniel, boarding the plane tonight, I saw something in you that I recognized,” the pilot explained. “It’s something that I’ve recognized in my own stepsons.”
Daniel just listened, without saying a word, staring intently at Maddox.
“It’s a sensibility that you seem to share with one of them,” explained the pilot further. “Our flirting tonight made me certain I was correct, and I think I can help.”
“Now I’m totally confused,” confessed Daniel.
“I’m very close to my two stepsons. Their mother died at a very young age, and it has always just been them and me. I know them both equally as well as I know anyone. We share everything with each other, but they couldn’t be more different. My older stepson, Kaine, was the typical athletic boy’s boy – liked anything outside, competitive, and masculine. His taste for and need to have women sexually developed very early. He’s obsessed with pussy. He can’t get enough of it. He seeks it out every moment he can and rarely is he satisfied. But that, my boy, doesn’t seem to ring true for you.”
“OK?” Daniel stammered.
“My younger stepson, Kyle, seems more like you. Unlike his brother, he was much more sensitive and kinder, feminine even – not so much in his mannerisms but in his sensibilities. He was still very competitive and driven but his focus was much more on close and intense relationships. And though he has and had relationships, both friendly and sexual with women, these special relationships were always with men.”
Daniel doesn’t say a word, but Maddox noticed a kind of sigh from him and knows his intuition was correct.
“I became aware of Kyle’s obsession from a very young age. He used to love to watch me shave. I would be naked, he’d sit on the toilet, and we’d talk every morning. I quickly noticed his intense interest in my penis. He was fascinated by it. Watched it move as I shaved. He constantly asked me questions about it. My scrotum was equally fascinating to him.”
Daniel is still silent but Maddox notices a slight movement in the crotch of the young lawyer’s pants and smiles.
“He loved to sit on Daddy’s lap,” Maddox continues. “Far past the time that others thought appropriate. He’d snuggle up to my chest and make sure my penis settled between his two butt cheeks.”
No one could have missed that Daniel’s thick cock was growing and tenting the front of his suit pants. Maddox couldn’t help but notice how much Daniel needed and wanted to adjust it.
“Go ahead, my boy,” Maddox said, rubbing the front of Daniel’s pants. “Don’t be uncomfortable.” Daniel sheepishly lifted his ass from the seat and moved his erect cock to a better position in his slacks and settled back in his seat.
“Thank you, sir,” Daniel said appreciatively. Maddox smiled and tousled his hair.
“Eventually, as he grew older,” Maddox continued, “During our shaving sessions, Jason asked to touch both my penis and scrotum. I allowed it simply because I didn’t want him to attach shame to his exploration. He wanted to lift and play with my testicles and hold and rub my penis.”
“The same thing happened with sitting in my lap, it became more erotic, he began to rock and move so I’d get an erection so he could feel my hard rod inside the crevice of his butt. We’d always have to change his pajamas before bed because they’d be so wet and sticky with precum. He’d always insist on licking the wet spot as he put on his clean pair.”
Smiling at the recollection, Maddox urges, “And you, my boy, I think are just like him. Is that true, Daniel?”
Daniel just stares at Maddox, as if weighing his answer.
“Is that true, Daniel?” asked Maddox
Daniel says nothing but nods his head in affirmation.
“I became concerned because it was clear my son had an obsession that he couldn’t control but asking these questions and attempting to try these things with any other men would be very dangerous. So, Jason’s brother and I decided there is something we could do for him and, that was to let him have our cocks, whenever and however he wanted them. It made it safer for him. It made it easier for him.”
Maddox unzipped his pants and revealed the front of his underwear, wet with precum, where the outline of his stupendous member was uncovered so Daniel could see and appreciate it.
“So have my cock, Daniel. Enjoy it. It’s our secret. No one will ever know. Be the cock hound that I know you are. Daddy gives you permission to use his cock however you need.”
Daniel just stared at the outline of the large, veiny rod, straining to stick straight up in Maddox’s lap. Relief. Arousal. Freedom. All in equal measure, washed over him. He was amazed at its size, at the girth, the thickness. “It’s beautiful,” he thinks. “It’s mine.”
He quickly starts undressing, getting out of his clothes as fast as he can, until he’s completely naked. He then crawls across the seat, his cock thick, hard and rigid. Maddox motions a welcome above his cock, with both hands, silently give Daniel permission to do whatever he desires.
Daniel laid his face in Maddox’s lap and breathed in, tonguing his underwear and sucking on the head of his cock, getting it soaking wet and sucking the precum through the cloth at the head of the erection. He slowly pulls the waist band down, letting the massive member pop up and slap his face. He pressed his face against it, slapping his jaw, rubbing the shaft so precum spread all over his face.
He grips the shaft, tonguing the head, spreading jizz all over to lubricate it. He uses both hands to pump it up and down, pressing his nose into the pubes, breathing in deeply, nibbling into the hair and licking and sucking – inhaling the scent, devouring it. Maddox sits with his hands behind his head, just allowing Daniel full access and the freedom to do anything he wants with the ample phallus. He pulls out the large, hefty balls, hanging loosely in their sack. He touches each one and hefts them together, rolling them in his fingers.
“That’s it, baby. Daddy’s balls are yours to play with too.”
Daniel puts his nose into the middle of the scrotum and begins biting the skin softly, licking each testicle and putting it in his mouth, sucking on each one like a lollipop. He licks them and suckles the skin of the scrotum, pulling on the sack and watching them move around. He lays his head in the pilot’s lap, licking the base of his cock.
“Don’t be afraid to suck it, baby. Daddy wants you to take it in your mouth.”
Daniel moves into a full-scale assault on the impressive rod. Sucking the head again, moving it around to each side of his mouth with his tongue, and then licking down every inch of the shaft, sucking the sides. Taking as much length and girth as he can, gurgling and guzzling, sucking and devouring. Maddox’s manhood intoxicates him.
“Good boy. Put it all in your mouth, baby. Take Daddy deep.”
Daniel breathes through his nose to take every inch possible and after gagging and popping up for air, opens his throat to take more. He’s wild. Worshipping. Both hands grasp the base, nestled in his pubic hair, squeezing and gripping it tightly, pumping slowly while the flawless dick goes down his throat.
Daniel pulls his face out of Maddox’s lap and says, “Daddy, I need you naked. Please get naked. I want to touch everything.”
Daniel lays down beside him on the seat as Maddox pulls his pants and underwear down first, revealing his strong and muscled legs. Dragging off his pilot’s jacket and his shirt at the same time, two broad shoulders appear, showing his hairy, sweaty chest that Daniel wants to lose himself in. He crawls on top, tasting the salt on his skin around the two pink nipples, gently biting one, making Maddox flinch and suck in air. He shifts to the other nipple and licks it too, biting down harder. Maddox begins to groan, as he licks and slurps across his chest, sticking his nose in hairy underarms as if memorizing the scent.
Daniel throws apart his legs over Maddox’s lap, nestling the pilot’s hard cock between his butt cheeks and pulls Maddox into a passionate embrace, kneading back muscles and squeezing biceps and simply holding onto that firm, masculine frame. He plunges his tongue into Maddox’s mouth, and the pilot kisses him back just as passionately. Tongues fight each other and Daniel devours his mouth.
Launching himself to the floor, Daniel pulls Maddox’s legs apart exposing his sweaty, hairy hole and he pushes his face into the crack and begins to wildly tongue, lick and suck on the pilot’s hole, biting the cheeks, kissing them, assaulting them with abandon. He shakes his face between the cheeks, losing himself in all the tastes, smells and sensations. Madly devouring the man’s hole.
Daniel crawls back up into Maddox’s lap, with his back to his chest and the pilot’s strong arms pull him in. The pilot reaches into a pocket on the side door of the limo, pulling out a bottle of lube, squeezing a generous amount on Daniel’s hand.
“Get yourself ready, baby, for Daddy’s massive cock!”
With all sense of modesty gone, Daniel throws his legs up, spreading the lube all over his hole and crack, sinking one, then two and then three fingers. Fucking himself hard. Maddox, with lube on his fingers, takes three fingers, sinks them all the way into Daniel’s ass, spreads them in and out repeatedly to open up the lips of the man’s pussy.
“Turn around and squat on my cock, baby,” Maddox instructs, “That way you can take it as slowly as you want.”
Maddox’s strong hands hold onto Daniel’s knees to keep him from dropping too fast onto his meaty pecker. The big mushroom head eases into him, his tight sphincter clamping down just behind the hard rim of his dick head. The first half of the pilot’s shaft pops inside his lubed hole, hitting that magic spot inside of him. He squealed from the intense burst of pleasure. He jerked forward and then felt that intense pleasure again as he leaned backward. Daniel’s hard cock was dripping on his stomach.
“Fuck yourself on my cock, baby! Milk me with your ass!”
Maddox let Daniel do just that, the lawyer bouncing madly up and down, using his ass muscles to squeeze and stroke his cock. The look on Daniel’s face was somewhere between ecstasy and joy.
Now Maddox used his solid body to thrust up against him, starting to meet each one of Daniel’s bounces, grinding himself up into Daniel’s ass. With each push-and-pull motion of his hips, Daniel could feel every vein on the pilot’s thick meat throb inside his asshole. Maddox’s hands slipped down to his ass, kneading his cheeks. Daniel’s cock was oozing like a faucet, slapping against his thighs and stomach, spreading precum all over himself.
He groaned, pushing back against the pistoning cock below him, and the pilot sped up. Maddox’s hands slid from his ass to his hips, pulling Daniel’s knees up into his chest, focusing that hole to take his cock as deeply as possible.
Daniel grabbed his cock suddenly, opening his mouth to yell out that he was cumming but all he could produce was a high-pitched cry. At that instant, he felt like someone had plugged his erection into an electrical socket. Uncontrollable spasms ran through his whole body and thick spasms of seed splattered his chest, his neck, his face and his hair. Spurt after spurt covered him.
Maddox bottomed out in his ass, his hairy body sliding hard against Daniel’s, balls slapping pubes to ass. His ass squeezed Maddox’s cock so hard when he orgasmed, he thought it might squeeze his dick off. He held on to him, keeping him still while he emptied his hot load in his guts. The force of it jolted him. Daniel could feel every squirt of Maddox’s load as it filled the depths of his ass.
Maddox, keeping his dick in Daniel’s ass, turned him around to face him, legs on either side of his lap, covering his lips with his and holding him. Daniel’s face pressed into his chest, tears streaming down his face.
“Thank you, sir, “ Daniel gushed. “Thank you.”
“It was my gift to give.”
They stayed like that until Maddox softened and his cock fell out of Daniel’s ass. Semen flowed onto his lap, cock and balls.
“I’m going to need you to clean me up, baby,” whispered Maddox.
Daniel fell to the floor of the limo again, cleaning up the pilot and himself, using his tongue to leave no trace of their blasts.
Putting back on their clothes, Maddox comforted Daniel and listened as he explained how desperate he had been to have such an experience and how deeply it had changed him, something he could tell no one else in the world.
Maddox held Daniel in his arms until he was ready to leave, having shared as much as he needed.
Good luck with your trial tomorrow, Daniel,” said Maddox. “Maybe Daddy can come see you in action some time.”
Daniel smiled, not really believing Maddox, thanking him again, giving him a passionate kiss and exiting the town car at the front door of his hotel, forever changed.
To be continued..
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