The Pilot

Teddy works for a billionaire on a charter flight, but when it turns out to be just him and the pilot sharing a hotel room and a bed, Teddy is in for the alpha-male pilot service experience of his dreams!

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Teddy was glad to buckle up when the plane glided to the ground at the airstrip in Bucket Hole. He was ready to move on with the plan. This part was easy. The flight took a long time, since this little old charter plane couldn’t go real fast. Teddy’s ass was sore, his legs were tired and his mind was going crazy for lack of stimulation. He was glad to have arrived in the town of Bucket Hole, which was aptly named, as looked like the kind of run-down-company-town without-a-company where you probably couldn’t find anything worth buying, the kind of town that produces nothing but buckets with holes in them.
Bucket Hole wasn’t much of a town, but it had a small dusty airstrip. It was about thirty miles from an oil field, which was the only reason anyone used the airstrip. That airstrip was the only reason Bucket Hole was still a town. When that oil field dried up eventually, the airstrip would be abandoned, and the town of Bucket Hole would fade away like a forgotten film.
The CEO of Blinkendale Energy was Charlie Walthenham, and it was he who had chartered the flight. Mr. Walthenham had arranged for Teddy to bring gourmet food from his country club — the Rockhard Country Club. Serving that food was essentially the only reason to have a flight attendant on the flight, since Mr. Walthenham could serve his own drinks (he merely drank his scotch neat). So he had hired Teddy from the country club to serve as his flight attendant.
Not a big stretch for Teddy, who used to work as an an actual flight attendant and knew well how to serve that food, because that was what he did at the country club every day. This was the same thing, but it came with a free trip to Wyoming.
It hadn’t become apparent until too late that there was literally no reason to go to Bucket Hole except to strike it rich in oil, and there was no chance of Teddy becoming a roughneck. It wasn’t worth what Mr. Walthenham was paying him.
The plane landed amid a cloud of dust on that airstrip. It was going well, Teddy thought, he looked like a real flight attendant. He even managed to look like he dreaded spending the night in this one-horse town. He emphasized his discomfort with the situation in hopes of inspiring Mr. Walthenham to give him a big tip at the end of the weekend. That might make make this whole thing worth the time.
Usually on these kind of small-plane short charter flights, the pilot didn’t wear the typical pilot’s uniform. Usually the flight attendant didn’t either, but Teddy wanted to look as professional as possible. The pilot seemed to have the same idea. He was tall and a bit of redneck, but only in a tasteful way, a slight twang in his voice, no holler, no trace of a trailer park. He was the kind of redneck people can trust, with broad-shoulders that filled out his uniform nicely. His name was Wyatt Kettenhauer, and he had a gorgeous head of raven hair that made Teddy’s heart skip a beat. He looked young, which Teddy thought might turn Mr. Walthenham off, but he did look solid. He exuded competence, and he was as handsome as a politician.
Wyatt even came out once the plane landed and stood there in the cabin next to Teddy. They both held in their breath, standing at attention as Mr. Walthenham waddled fatly off, yelling at some poor soul on his cell phone. Wyatt made eye contact with Teddy, but both stayed at attention like soldiers.
“You had better get it done, asshole, I’m not waiting another day! I want motherfucking results, or I will come down there to St. Louis and ram my foot so far up your ass you could snort coke off my pinkie toe!” Mr. Walthenham strode out, seemingly not noticing Wyatt or Teddy at all.
They waited until he was good and gone. Since the airstrip was so small, that meant waiting until he left the tarmac entirely.
“Phew! I tell you one thing,” Wyatt said, taking off his cap when they were truly away from Mr. Walthenham. “That man is frightening with a capital F and a capital U. E’ry time I land the plane with him on it, I breathe a sigh of relief, cuz I just know he could have me pistol-whipped for makin’ it a bumpy ride.” His Western twang was peal-y like a mockingbird, his voice a slow rumble like a cowboy, which Teddy soon realized he was, underneath that pilot’s uniform. Or at least he had grown up on a ranch and fancied himself a cowboy, right down to the well-worn cowboy hat when he was back at home. “If you don’t mind me, Teddy, my good man, I’m gonna get find some fine slice of womanhood and see if I can’t plow her furrows.”
“Yes, sir.” Teddy was disappointed in both his desire and his metaphor. Teddy wanted to spend time with Wyatt, whose handsome face and alluring stature got Teddy excited. Teddy was a keen appreciator of a well-formed male physiqye, and Wyatt Kettenhauer was an exemplar of the masculine shape.
Teddy left the plane after tidying up and getting it ready for the return trip. Wyatt the pilot headed into the rinky-dink airport, but Teddy hung behind. He didn’t want it to be obvious he was following Wyatt.
In a tiny airstrip like this one and in a tiny town like Bucket Hole, it should be easy, Teddy thought, to not look like a stalker. There was probably only one motel, only one bar (if that), not that many places a ranch-hand floozy might hang out — that was the kind of woman Teddy thought Wyatt was likely to be after. There was no way to hide in a town like this, and there were hardly going to be multiple women available.
Or maybe the place would be crawling with loose women, given the roughnecks that came through on a regular basis en route to that oil field. They no doubt came out on leave with full balls and cooped-up stiffies. Teddy knew the type. As Teddy moseyed to the hotel though, it looked like there was literally nobody in this podunk little burg.
“How many vacancies have you got?” Teddy asked when he came in the front lobby and approached the desk.
“One,” said the waify, bored-looking clerk. He didn’t look at the computer screen.
“I’ll rent it. Is it a single?”
“Yes, sir,” said the clerk.
Teddy nodded. That was good. He was confident Wyatt hadn’t rented a room first, he most likely went straight out to get laid. Men like Wyatt were like that. He wouldn’t even think about a place to stay tonight until he actually needed it. The clerk handed over the key. He didn’t bother to tell Teddy in which direction the room was. Teddy used to be a hotel clerk, so he mentally deducted one star from his rating for this place.
Not that this was the kind of hotel that cared abouts it rating. There was literally no competition. It was either sleep in the hotel or get eaten by a bear, so the clerk’s hospitality only had to be greater than that of a hungry bear.
The room was drab and dreary. It wasn’t dirty, or at least not actively so, but it was hardly clean either. It was coated in a layer of dinge. But at least it didn’t smell like urine or blood, Teddy thought, which sometimes happened in these tiny motels. Once they get a bad stain, it never goes away, because management won’t spend what it takes. The bed was surprisingly comfortable, and the bathroom was clean, which was what was most important for Teddy. He could deal with the rest.
He settled back to relax and wait for Wyatt to be visible from his vantage point in front of his room, where he could see much of the main street in this town. The clerk inside the lobby kept watching Teddy, trying to figure out his game.
But Teddy just watched the dullness develop as day turned to night, and the moon’s long darkness spread over the landscape. There was the town’s bar too. Teddy couldn’t make out the name on the sign. After a long time trying to decipher it from this far away, Teddy just googled it.
The Clean Pipe. Sounds like a biker bar, he thought. It didn’t even have a proper website though. Just a Facebook page last updated seven months ago.
He soon saw Wyatt coming out of the bar. He staggered out shouting at someone inside, like he had just gotten in a fight and been kicked out — he hadn’t been in there long enough to get drunk though, or at least not real drunk. He sighed and came towards the motel.
Teddy left the hotel room and waited outside as casually as he could muster. He nodded to Wyatt, who had a visible erection in his tight pilot’s uniform slacks. It bulged against the fabric, and Wyatt gave it a squeeze through his clothes as he walked. He must have gotten in trouble with a woman, Teddy thought. Wyatt went to the clerk in the window, ignoring Teddy.
Soon, Wyatt’s deep voice filtered out into the night-time air. “No vacancies! What are you talking about? No one ever comes to this shit-heel of a town! How could you be full?”
Finally, Wyatt came out with an angry snarl. He glared at Teddy, then his snarl brightened into a smile. He walked over to him. “Hey, did you get a room?”
Teddy nodded.
“Can we share? I couldn’t get one. This one-horse town is down to a half-a-horse, and it’s sickly,” Wyatt said. “There was one girl in that bar and she was a prude. She wouldn’t even talk to me!” He threw his hands in the air, then winced because the motion caused pain in his sensitive cock. His erection appeared to have diminished a bit, but there was still a noticeable bulge in his tight pants.
“There’s only one bed, but we can share,” Teddy said with a casual shrug. He sniffed Wyatt’s breath. No alcohol. “Are you drunk?”
He shook his head. “I’m not drinking tonight. Mr. Walthenham seems like the kinda man who might wake me up in the middle of the night cuz he wants to leave early. I gotta be sober as a Monday morning,” he said. He took a deep breath and looked up and down the main drag of Bucket Hole. “Well, I’m gonna go try to get laid. Nothing personal, but if I can, I’m not sleeping with you tonight. Don’t wait up.” Wyatt paused. “You wanna come with me?”
“No thanks, I’ve got a girlfriend,” Teddy said. He scribbled down his room number and passed it to Wyatt. “Come on in. I’ll leave the door unlocked.”
Wyatt scoffed like he didn’t get why a girlfriend should stop Teddy, but he accepted it. He headed down the street to see where else there might be some females. Teddy suspected he would have poor luck — in a tiny town like Bucket Hole, there were not likely to be many options as far as nightlife went. That bar he got kicked out of has gotta be the entirey of Bucket Hole’s nightlife. Probably there were more prostitutes when the roughnecks had leave.
But Wyatt was a charter pilot, and he saw the perks of that job as including all the fine women he met throughout the world. Ladies loved pilots. He could talk a woman out of her panties in virtually any city. He’d bedded (women who claimed to be) Saudi princesses, billionaires, Bruce Willis’s daughter, porn stars and supermodels.
But Bucket Hole, Montana, was proving to be difficult. There was no one here.
It was barely an hour after they separated when Wyatt knocked on the motel room door. He pushed right in when Teddy opened the door. He still had his cowboy hat on, and he removed it as he entered, then put it right back on. His cheeks were ruddy, and he chewed on his lips as he fumed.
“Goddamn this town sucks! You know it’s a dry town? Apparently liquor stores are illegal, there’s only one liquor license in town and it’s the bar that just kicked me out.”
“That sucks,” Teddy said. “I thought you weren’t drinking?”
“I’m not! It’s just an observation. No wonder there’s no nightlife here! There’s no minibar in this room either, is there?”
“No sir.”
“Well shit… I guess this is officially the most boring town in North America, huh, Teddy?” he said. He sighed. Then he glanced up at Teddy with a guilty grin. “Or maybe we’ll fool around when the lights go out, you know what they say — cowboys can do it in the dark, it don’t count, yee-haw!” He paused to gauge Teddy’s reaction. “And they say that about pilots too when they ain’t in they home time-zone, shit yeah!”
Teddy laughed along with him. He wasn’t sure how joking Wyatt was. Hopefully not at all.
Both of them settled into Teddy’s room, and Teddy was glad to have a chance to see Wyatt like this: casual, shirtless, brushing his teeth, taking a shower, putting on deodorant even just to go to bed, clipping his toenails. Wyatt talked, mostly about women, the whole time, and he badmouthed Mr. Walthenham, who hired him often but never learned his name. He kept calling him “Ryan Kettleman”.
Eventually, the night dragged on, and they put on a movie, some superhero thriller that seemed poorly edited for tv and didn’t entirely make sense to Teddy. He could barely follow it though, because Wyatt kept talking the whole way. Mainly he commented on the women onscreen and compared them to the women he had slept with. His conclusion was that he got hotter women than this movie starred. It annoyed the piss out of Teddy, who hated people who talked during movies. Wyatt was too handsome to be mad at though.
Finally, the movie was over, and Teddy was already half-asleep as he turned the light out. He could tell Wyatt was restless and didn’t want to go to bed just yet.
Wyatt paced for a moment quietly. He hadn’t gone to bed with neither sex nor alcohol, nor even weed, in a long time. He wasn’t an addict, he thought, but it was difficult to convince himself that he could go to bed horny and sober. It just didn’t feel right. Every time a woman appeared in his mind’s eye, his dick rocketed back to full erection, and Wyatt resumed pacing in the dark hotel room.
Eventually, he did lay down next to Teddy. Wyatt was used to a more comfortable bed than this. He rarely slept at home, as he usually was in hotels all around the world — wherever Mr. Walthenham needed to go — or sometimes in the bed of his latest female conquest.
Once he got under the covers just a few inches from Teddy, however, Wyatt realized he could satisfy his sexual urges as well. He genuinely thought of it as “not counting” in a situation like this, in a tiny town and a cramped motel. In pilot school, everybody had said it doesn’t count if you’re at least two time zones away from home. That meant cheating. It was okay to cheat on a wife if she was at least two time zones away.
But, Wyatt thought, it could apply to messing around “on the downlow”, as the black guys say. It would not be Wyatt’s first time. It would be his first time since becoming a pilot, however. Women threw themselves at pilots. So did men like Teddy.
“Hey, man…” Wyatt whispered, finally breaking the silence in the silentious motel room, the only sound being the whirr of the air conditioner. “You wanna jack off with me?” he asked with confidence, like he already knew the answer.
Which was true. He did know the answer. Wyatt had noticed Teddy checking him out all day, and he knew perfectly well Teddy wanted to swing on his dick. Most male flight attendants were that way.
“Hell yeah. I didn’t know you were into that,” Teddy said, hoping to sound coy instead of naive. His hands flitted over underneath the covers to Wyatt’s muscular chest, and Teddy scooted closer, so he could feel the solid warmth emanating from Wyatt’s body.
“I grew up on a ranch.” Wyatt chuckled dryly. “You know, out there you stick your dick wherever you can find a nice tight hole, ya feel me? Sheep run scared ’round my parts. Not that I ever partook, cuz I had females hanging off e’ry inch I got, ya feel me?” He patted Teddy on the head, and he gently pushed his head closer to Wyatt’s crotch.
“Uh-huh.” Teddy sighed and allowed Wyatt to move his head closer, putting up just a little resistance, like a nice woman would, just enough resistance to let Wyatt know this wasn’t an automatic gimme. Teddy kissed Wyatt on the treasure trail of body hair leading from his flat belly to his dick, and as Teddy moved lower and lower. He resisted Wyatt hurrying him down to his groin. Finally Wyatt’s half-hard dick collided with Teddy’s face. Wyatt let out a twanging moan as his dick touched Teddy’s hand. Teddy gripped that thick shaft and gave it a few strokes, then opened his mouth and kissed it, right on the tip.
Wyatt’s whole body buckled. He whispered “Yee-haw” again and laughed, very quietly, even though there was no way anyone could hear but Teddy. He pushed Teddy’s head lower on his dick.
“Yeah, man, put your mouth on it…”
Finally, Teddy did so, allowing his mouth the envelop Wyatt’s rapidly firming up cock. It pulsated like an alien beast, and his muscular chest rippled beneath Teddy’s fingertips. The taste of his dickshaft was clean and sweet, with a musky after-scent. He liked feeling Wyatt’s rock-hard meat exploring his throat, pushing all the way in until Teddy’s nose nuzzled Wyatt’s pubic hair.
Soon he was rock-hard, his cock throbbing on Teddy’s tongue. Wyatt moaned as he guided Teddy up and down, firmly but gently. Teddy’s tongue slathered spit up and down Wyatt’s rock-hard shaft, and the first few drops of salty, sun-bright precum hit Teddy’s tongue.
Much to Teddy’s surprise, Wyatt intended to return the favor — he assumed a macho pilot and boss like Wyatt would never reciprocate. He leaned down and stroked Teddy’s dick with one hand. It was a slow, lazy stroke, but it got Teddy hard, and soon both men leaked precum onto each other. It was almost, but not quite, a sixty-nine because Wyatt didn’t taste Teddy’s dick —where Wyatt came from, men could jack each other off in exchange for whatever or because they lost a bet, but swallowing a nut was too much. Wyatt wouldn’t do that. He could do almost anything else though. Teddy was not gonna complain.
“Hey, man, can I stick ya?” Wyatt asked, his voice soft and low, aimed directly into Teddy’s ear.
“You gotta gimme a reacharound,” Teddy said, gasping for more. He chased Wyatt’s cock with his mouth, but Wyatt kept moving it out of his way, already getting in position to go up Teddy’s ass, even though Teddy hadn’t agreed yet. Wyatt wasn’t used to anyone telling him no.
“Hell yeah, you oughta be a full-time flight attendant, yessuh. Pilots could use someone with a mouth like you. Women stewardesses are teases these days, I tells yah!” Wyatt said with a loud whoop, which he then muffled. “Sorry, that was loud.”
“No one can hear.” Teddy’s voice was huffy and plaintive, as he was desperate to get Wyatt’s manhood inside him.
“I know… This kinda thing is best done on the hush and in the dark, ya feel me?”
“Yeah…”
Wyatt slid behind Teddy and hefted his dick between his cheeks. Teddy’s asshole tingled, then the tip slid in. Teddy bit his lip as pleasure and pain both enveloped him in equal measure. This was happening faster than he thought it would. Despite the lack of any potential audience, Teddy still swallowed back a moan of pleasure, as sensations sparked up and down his body. Wyatt’s cock slammed into his prostate, both men moving as one as pleasure filled both men’s bodies.
The hum of the air conditioner outside the motel room seemed impossibly loud. Teddy couldn’t hear anything but that and Wyatt’s heavy breathing condensing on the back of his head, as Wyatt’s hands explored Teddy’s smooth chest. The intense pressure overwhelmed him, but gradually loosened with every passing second.
“Sssh… it’s okay,” Wyatt said, his low twang echoing in Teddy’s ear like a banjo. His hands roamed over Teddy’s body and then gripped his dick. A jolt of pleasure shout through Teddy. “I’m inside ya now, son…”
Teddy’s whole body tensed as more of Wyatt’s cock slid in, each centimeter sending a new wave of bliss to wrack his tiny frame. He clenched and bit down. Wyatt began slowly stroking him in sync with the gyrations of his hips. His balls slapped against Teddy’s thighs.
He kissed Teddy on the lips, and their tongues interlocked in Teddy’s mouth. Teddy let out a long, slow moan of pleasure. He couldn’t believe how good this felt. It continued for what felt like forever, and Teddy didn’t want it to end. He cried out and gasped. Wyatt moaned over and over, smiling, glad that he had gotten his rocks off after all, even without a girl. Teddy was probably tighter than any of the women in this town anyway.
Wyatt grunted and his body spasmed. Cum sprayed into Teddy’s ass, great gobs of it that filled him and coated his insides. Some of it dripped out and onto the mattress beneath him. A burst of it seeped into Teddy’s flesh, the creamy heat flowing into him like a river.
“Shit, boy… Hell yeah,” Wyatt said. Spasms of pleasure overwhelmed his body. His free hand tightened into claws that dug into Teddy’s body, while his other hand kept stroking Teddy into an impassioned orgasm. Bliss erupted in Teddy’s body, while Wyatt’s climax turned to a low moan that resonated in Teddy’s ear.
Teddy let out a sigh as he shot his own load into Wyatt’s hand. He felt a slow-burning orgasm that only grew as he came and Wyatt’s dick limpened inside him. Then he took it out. He kissed Teddy on the cheek, where his lips lingered as his hands ran up and down Teddy’s body.
The smell of cum filled the air. Wyatt smiled and pounded on his chest. He flexed his biceps too, as though there was a woman here to impress — of course there was only Teddy, and he didn’t even face the right way to see. Teddy sensed the flexing of his powerful muscles behind his back though, and he rubbed his smoothness on Wyatt’s powerful body.
“Shit…” Wyatt said again with a chuckle. “That was right nice, yessuh. I am sure glad I hooked up with you. You’re a good flight attendant.”
“I’m not even really a flight attendant,” Teddy said with a laugh.
Wyatt shrugged and settled back onto the motel bed. Teddy curled up next to him. He liked the solidity of Wyatt’s muscles and the warmth of his body heat as it suffused over him.
“You’re a good pilot,” Teddy said with a giggle. He snuggled up to Wyatt’s body. “Tomorrow, I might be available in the cargo area during the flight home. Maybe you could sneak back there when the plane’s on autopilot.?”
“That ain’t allowed,” Wyatt said with a shrug. “But if you treat me like that again, son, I’ll do whatevuh you want!”