Bobby and The Boss

by TallyMans

18 Aug 2020 5458 readers Score 8.7 (69 votes) PDF Mobi ePub Txt


The Hotel Room

“Uuhhhh, Uuhhh,” he moans and grunts as he lifts box after box from the backseat of the king-cab pick-up. Placing them on the dark asphalt of the Suburban hotel parking lot.

“Having some trouble there, Bobby-boy?” his boss says as he looks toward the young man who is unloading the hard-orange-plastic crates from the pick-up, “When they hire more men for the survey crew, you are going to be the ‘Little Shit’ who has to do what we tell you. And all what they say. You must pay your dues. Boy. You understand?”

“I get it, boss. I get it. I do.”

He grumbles in a low undecipherable voice to not be heard by his boss.

The older man smiles at the young man-kid lifts and strains under the weight of the survey equipment in the awkwardly shaped plastic containers.

“Carry that crap up to our room,” he says, “You know the drill. Do it.”

“Yes, sir. Yes, sir,” the kid moans under the weight of the task before him.

They make their way across the parking lot. Boss has parked as far away as he could to further complicate things for his young Survey Tech.

The surveyor trudges up the steps, with only an overnight bag slung over his broad shoulder and nothing in his hands except the work order for the job; while the kid lugs a box under each arm and carries two more in each of his hands. His knuckles turning red under the weight of the survey equipment and his own bag of clothes.

All Bobby sees is the man’s round ass, outlined like perfectly shaped globes beneath the fabric, which are in his face as he follows him. Each buttock tightly compacted into a pair of dirt-encrusted Levi jeans.

“I gotta take a piss. I gotta piss,” the surveyor says as he walks, said as loud as he can to garner attention from anyone who maybe within earshot. He is cupping his balls and cock in his hand, on the gangway-balcony to their shared hotel room.

Behind him, he can hear the kid huffing and puffing as he lugs the misshapen boxes. He grins and smirks to himself. It is one of the things he likes about the job. Being an asshole. He giggles his ass in the kids face. But in a subtle way. Letting him know that he is free from any of the burdens.

“You got the key, Bobby?” The boss demands.

The boy fumbles as he places each crate on the concrete walkway in front of their second story balcony-walkway room.

“Hurry up! Hurry up! I gotta take a piss!” He says even louder. “I am going to go right here if you do not hurry the fuck up, Boy.”

“Yes, sir, I’ve got it in my billfold. I got it.”

“Get it out, Boy!” he says, “I must have left mine in the damn truck.”

But the key is in billfold. Too. He just wants to make it more difficult for the kid. And he laughs to himself at the pressure he is adding to the addled boy.

But the kid is doing well. But he will not tell him. This is part of the hazing that was done to him so many years ago and what he has repeated on other men when they were in the same work position.

Bobby fishes into his wallet and gets out the electronic key. He flashes it in front of the keypad to the room. It unlocks, a low clicking sound, barely heard by the two men, is the sign the room is ready to enter.

“Hurry, Bobby, I’m ‘bout to fucking burst, that beer I had at the restaurant is aching to get out. And it wants out!”

His boss storms into the room, as Bobby steps aside, allowing the demanding man, into their room.

Barely into the room, he is hastily unzipping his dirt and grime-encrusted Levi dungarees while he slings the bag from his shoulder onto one of the double-sized beds. The one nearest the bathroom. As he walks into the bathroom, his cock dangles from his unzipped-zipper and unbuttoned jeans. He waves it so the kid can see it. He wants the kid to see it.

“Fuck. Fuck. Fuck,” the man shouts as he makes his way into the bathroom. Leaving the door open as his worms his hand into his jeans.

Bobby with the drudgery of the orange plastic containers, places them by his bed on the carpeted floor, and closes to the curtain-drawn windows, where he knew he would be sleeping. He plops down on the ugly-patterned comforter atop the double bed. And lets out a loud sigh of relief. “Will this madness ever end?” He quietly whispers to himself. And shakes his head in astonishment. And disbelief. The man is an ass. He ponders.

Bobby can hear his boss pissing into the toilet bowl, the piss bouncing off the slick enamel of the porcelain, as the sound breaks through the silence of the otherwise quiet room.

“Turn up that fucking A/C, will ya, Bobby!” he yells from the bathroom, “Its fucking hot, today! Ain’t it?”

The kid does not reply but gets up and cranks up the A/C. Down to 65 degrees. And then finds his way back to his propped-up position on the bed.

Bobby has become accustomed to the frequent demands of the man, he calls, “Boss.”

Boss stumbles from the bathroom. His jeans unbuttoned and unzipped, wisps of his golden furred pubes peak through the open zipper. His button-down shirt, open and falling off him, like a loose ragdoll. It lands on the floor near the front of the sink.

“Whew! Damn! Fuck! I am feeling fucking better now!”

The man kicks the boots from his feet and tumbles onto the bed.

He whisks the dirty socks from feet, slinging them like a boomerang across the floor. They land on the stand next to the high-def television in front of them.

“Fuck! Fuck!”

He falls back on the bed, flailing his feet to the air, as his jeans are shimmied down his beefy hairy legs.

The Boss is naked. Unencumbered.

It did not take the man too long once he got back to the room before he shucked all his clothes. The Boss had bragged that he likes to be comfortable when they left the restaurant and made their way to the Suburban.

This is the first overnight trip that they have made since he was hired as a Survey Tech. A few weeks back.

Boss scoots across the bed, propping himself against the headboard. His masculinity exposed in all its rigid splendor. His hands resting on either side of his thigh.

He splays his legs open, letting his cock, flop from side-to-side as it adjusts to the chill of the room. He fondles his rapidly growing masculinity as he looks at Bobby.

“You aren’t naked, yet Bobby?” Boss says. “What’s matter with you, kid?”

“Naw, sir.” Booby replies, “I am not.”

“Once I get home, every day from work, I strip off all my clothes and relax. It is what I do.” The Boss says, “Why don’t you? Relax, kid. Relax. Relax.”

“Never have really done it, before, sir,” the kid shirks at the man’s suggestion. The kid bows his head, almost as if he is overwhelmed with shame.

“You have nothing to be afraid of, boy.” The Boss says, “we are both men here. I am just older, is all, ya know.”

Bobby is still in his dirty shorts, an even dirtier tee, boots, and camo ball-cap, both men are scooted up the headboard to the front of the bed.

“Why you actin’ like what I am doin’ is something shameful, Boy? What is the matter with you?” Boss asks.

The kid scoots to the end of the bed. On his left of the bed is the equipment in the orange plastic containers, a chair, and a flimsy looking table, supposedly something to eat on, if necessary.

“Take yer shirt off, at least, boy, get comfortable,” Boss whines.

He relents.

As Bobby stands, he locks his ten lithe fingers under either side of his tee and lifts it over his head. As the shirt rises over his muscled chest, the cool air perks up his red-spiked nipples; they grow hard, in an instant. Wisps of fine delicate blonde hairs cover the 19-year-olds heavily muscled chest. And with each move his muscles respond to the movement.  While the hairs are like tiny ghosts sweeping over the boys fiercely hard-earned muscles. Even not working, Boss can see the definition of the kids’ body. Boss’ cock pulses from the sight.

He can feel the eyes of his Boss rake over him. Almost drilling a hole threw him.

“Better,” Boss asks, “Is that better?”

He looks to his Boss.

“Yes, sir,” he answers in hesitation.

When he looks toward his Boss, he sees that the man’s hands, both, are cupped firmly around his hairy blonde-haired balls. The man does not let go of his packaged balls, even though he knows his young helper is staring at him.

“You boys nowadays are too afraid to be naked ‘round other guys. We all have cocks. No big deal in my eyes. If you got it. Show it off is what I say. And you, Boy, have nothing to be afraid of.” His Boss explains. “Not at all.”

Bobby walks to the bathroom and closes the door. It is within a few minutes that the sound of a flush is heard, though the muffled closed door. The Boss hears. Bobby once again opens the door and strolls back to his bed, by the door and the window.

On his bed, Boss strokes his cock as he rests atop the ugly comforter.

Bobby turns his head away, trying to not catch sight of his Boss fondling his inflated tool.

“You not horny, boy?” Boss barks at him. “I am. See. See.” While Bobby’s head is turned towards the curtained window.

“Naw, sir. I ain’t horny.”

Bobby scoots over to the side, in the direction of the window. He can hear his boss’ hands gliding up and down, travelling the length of his cock. He is being as loud as he can as he repeats these actions.

“You ever jack-off with your buds, back in high school, Bobby?” the older man asks.

Bobby does not answer. His back away from the man.

The silence is his answer. He hopes.

“You hear me, boy? You jack-off with your buds?”

Bobby still does not answer. He attempts to feign sleep.

The bed squeaks as his bossman gets out of the bed.

The older man reaches and cups the short-covered ass of the kid.

“Uhhhhh!” Bobby moans, as his boss clamps down tight on his ass, “What the fuck? What the fuck?” Bobby is startled by the man’s hands on him.

As his bossman squeezes the boy’s ass, the kid bucks on the bed causing him to turn face-up in the bed.

“Whoa! Whoa!” his bossman says once he realizes what he sees, “Calm down, boy, just goosing ya is all!”

Once the boy is once again on his back, Boss’ eyes are drawn to the obvious bulge in the kid’s shorts.

“You gotta yourself a hard-on there, I see.”

Not waiting for the kid, Boss yanks down the kids shorts. Bobby grabs at them but cannot stop the man from pulling them down.

“Fuck! Fuck!” Boss yells at the sight of the kid’s cock. The kid is not wearing any underwear but is ‘going commando.’ The same as the boss had been before he stripped.

The kid does not struggle, once he is exposed. He relaxes, spreading his legs, as best he can with the shorts gathered at his knees.

Droplets of cum leak from the kids thick Eiffel Towel-like cock which is jutting from between his legs.

“Fuck! Bobby that is some cock, you got there,” Boss says, as he looms over the kid, like a giant as his hand once again resumes the stroking of his cock.

Boss lets a solitary finger roam over the engorged blood-red helmet of the boy’s cock. The tender but rough touch of the boss man’s calloused fingers causes the boy to eject more of his cum from the steel-hardness. A clear film of juice shines in the bedside light which brightens the room.

“Mmm, you surprise me, boy,” his boss says, “Never expected to see such a piece of meat between your legs.”

Not waiting for the kid’s response, Boss ducks his head down between the kid’s legs and devours the young man’s cock, down to his pubes. His nose buried in the fine curly hairs around the kids cock and balls. The older man’s speckled grayish-colored beard mixes with the light hairs of the kid’s blonde pubes.

The kid bucks as his boss gulps down the juice from the boy’s ball-sacs.

“You don’t mind, do you?” Boss asks after coming up for air.

“Uhh. No. No. It feels good, Sir.” He mumbles. “It feels really good.”

Bobby does not feel the shorts being removed. Over his still booted feet. All he feels is the hot wet mouth of his Boss, each, and every time, his cock hits on the back of the man’s throat. He sighs loudly as the man increases the suction. Paying special attention to the young man’s engorged cockhead. Now swollen so magnificently that it feels the man’s mouth. All of it.

Boss peeks down between the kid’s legs, to the pulsing hole, and is greeted with a golden ring of fine hairs encircling the virgin ass of the boy. He blows on this little field of yellow deliciousness, fanning the hairs like a welcoming wheat field. The wave back with the gentle breeze created from his breathe. It is a welcoming site. The kid’s asshole.

Boss manages to dip a finger into his mouth. Moistening it with his flowing saliva. And then gently massages the entrance of Bobby’s ass. Wetting down the fine hairs that had whispered to him earlier. Bobby squirms as he feels the pressure being applied by his boss’ able finger. He does not stop him.

“Relax.” Boss says as he takes a rest from one of his many plunges of his mouth onto the boy’s cock. “Relax. Relax.” He says in a calm voice.

An agile finger slides into Bobby’s hole.

“Oh! Oh! Oh!” Bobby moans as his hairy hole accommodates the slickened finger.

“That’s right. Yeah. Yeah.” Boss says as he works his finger about in the boys now moistened hole. Lube being created as the friction increases by the boy sweating in anticipation.

The boy’s cock stiffens in his mouth. Once he resumes his devouring of it. He thinks to himself as he feasts on the young man’s hungry cock. Of the salty taste of the young stud as it fills his mouth. Each poke of his finger stirs more of the leaking juice from the boy’s balls. Which he drinks like the nectar a young Adonis.

He pumps harder. Ramming his digit more forceful into the young man’s cavity. Each time brings more bountiful offerings from the boy’s fountain. He does not let up.

The boy lifts himself off the bed as the pressure grows on his prostate. Boss coos him. Gently.

“Breath. Boy. Breath.” Boss says repeatedly. The room grows quiet.  Quieter. The sound of the A/C is all that is heard along with the gentle whimpering of the excited young man and the Boss.

Boss stops for a moment. But keeps the finger buried deep in the kid’s ass.

The boy’s breath eases. Relaxes.

Boss lets the boy gather himself. His breathing normalizing. But there is a light sheen of sweat covering the kid’s body. They room is quiet except for the slow breathing of each of the men. Boss’ cock is throbbing hard and steadily leaking its own precious liquid onto the comforter. And the heat from the encounter has each man’s flesh flushed red. On Bobby’s lightly heaving stomach, a puddle grows of his virile seed. A clear trail meanders from his towering erection, following the path of his erect cock. Boss has lifted his head from the self-imposed face-fucking he was engaged in on the boy’s tool. A string of the young man’s juice; mixed with Boss saliva makes a spider-like web in its combination.

Boss admires his handiwork. How easy it was to engage this young man in this endeavor. He had his suspicions when he hired him. Many. It helped that the young man was a carbon-copy of him at that same age. Nineteen. Muscular. His chest clearly outlined in the tee as he sat across from him in the restaurant where the meeting took place. And blonde hair. And outwardly timid as he sat in the chair. He figured it was nerves. Being a job interview. But that was something he once had, blonde straight hair, but now had turned gray with age.

Boss injects his finger back into the boy’s hole.

“Ah! Ah! Ah!” The kid sighs at the slight poke. But Boss speeds up as the kids groans, grow louder.

“You like my finger in your ass? Doncha boy?”

Bobby moans in indecipherable words. But he means, ‘yes.’

“Yeah. You do. Boy. Your cock just spurted, itself, a load of pre-cum.”

Boss licks his lips but does not devour the stream of juice that the boy is expelling from his hard fleshy-tool. Boss adds a second finger to the one that he has been plunging into the boy’s ass.

“Fuck! Fuck! Fuck!” Bobby lets out a yelp when the two digits are inserted into him.

“Oh, Yeah. The boy likes that. Doesn’t he? Doesn’t he?”

Bobby gives up more of his juice which the Boss smears over the glowing red bulbous head of the boy’s cock.

“STOP! STOP! STOP!” Bobby pleads as his sensitive cockhead is smeared down with his potent juice.

“Relax, Kid. It is all good. You can take it. You can take it.”

Bobby squirms on the bed. Jumping as best he can but Boss manages to wrangle the young buck in place.

Boss leans in, to lick some of the spent juice that has coalesced atop the crown of the kids’ cock. Sweet. And somewhat salty. More so than it was earlier. Fresh juice from the balls of this young stud. Tasty. The kid steadies himself when he feels the hot mouth of his Boss, once again wrapped around his cock.

The boy’s cock grows bigger under the pressure. Boss knows what that means. And so, does Bobby. And he begins to suck harder. And ram the two fingers harder into the boy’s ass.

“Fuck! Fuck! Fuck! Fuck!” Bobby yells as he empties all of himself into the mouth of the man, he calls Boss. None is wasted. Nary a drop as Boss savors all of Bobby’s offering. Bobby bounces on the bed like an out-of-control bull but Boss does not let go but stays clamped on him like it is his last ride. He takes all of it. Not wasting none of the young man’s gracious blessing.

It is a few minutes before the young buck calms down. Drenched in his sweat. He chest heaving from the sexual exhaustion. It is then Boss lifts his head from the boy’s cock and wipes his lips with his tongue.

“That was good.” Boss says. “I drank it all.”

Bobby does not say anything. His eyes are closed. As they have been throughout all of this. In his own world.

“You rest now. I am going to take a shower. You did good, Boy. Real good.”

Boss walks to the bathroom and turns on the hot water. The sound of the shower running fills the hotel room. He leans out of the bathroom. Nestled against the doorframe like the conquering hero.

“You remind me of me at your age, Boy. And an air of innocence around you. It was why I hired you. This innocence.” Boss says. “I wanted to be reminded of what I once was. And would never be again. Did not want to be again. You rest now.”

And then he ducks back into the bathroom. And dips under the showerhead. The hot water covering him.

“We are far from finished, Boy.” Boss says as he pulls the shower curtain. “I have much in store for you. For us.”

Bobby rolls over on the comforter. Spent. And begins to snore lightly.