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milo miles | Chapter 1

job interview

Coach Stone and Milo Miles
August 17, 2023 | Full Length Video : 41min 53sec
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Nearly a month ago Milo Miles had sent in a job application to the renowned Stone and Associates Corporation. He got no response initially and, after a few weeks passed, had glumly given up on the possibility of a reply.

However, in the fourth week, Milo received a call from Mr. Dillon Stone himself, CEO of the company. He apologized for the lateness of the response, but there had been so many applicants that they were just now getting to reviewing Milo’s resume. Mr. Stone was hoping Milo was still interested in the position and willing to come into the office for an interview.

On the morning ...[Read more]

On the morning of the set date, Milo came to Mr. Stone’s office pumped up and ready to impress. He met the successful businessman and gave the interview of his life. Milo was well-spoken, prepared and organized. He answered each of Mr. Stone’s questions with adept knowledge of the business and he thoughtfully presented the ways in which he would be a valued contributor.

After the interview concluded, Milo sat nervously in his seat. Mr. Stone had seemed genuinely impressed, oftentimes intrigued even. However, the CEO peered into his laptop occasionally, his gaze lingering at some unknown subject of interest that worried Milo. Was his resume not good enough?

After a brief silence, Mr. Stone cleared his throat and closed the laptop. He emphasized that the company was seeking applicants with self-motivated constitutions. They also prized people who could adapt to any situation when called upon. They were especially interested in flexible, versatile types.

Mr. Stone believed that from what he could ascertain about Milo during the interview, the young man seemed quite likely to have these qualities and more. But there was something else that the cunning veteran had gathered, as well.

Before calling Milo into the office for the interview, Mr. Stone disclosed that he had spent time on the internet doing some casual research on Milo. Mr. Stone let that revelation sink in for a moment. Though Milo stayed still and did his best not to react, Mr. Stone couldn’t help but notice a bead of sweat pop out on the handsome candidate’s smooth brow.

Mr. Stone noted that he had discovered an alternate Twitter account that belonged to Milo that displayed images of the boy that were most definitely for ‘mature audiences.’ The bead of sweat on Milo’s brow trickled down the side of his face.

Mr. Stone looked his applicant directly in the eye. Milo’s internet photos also showcased himself as a notably very versatile individual with a propensity for pounding on and being pounded by tall, muscular, and of course, very hung DILFs.

Milo inwardly kicked himself. How could he have forgotten about that Twitter account? He silently bemoaned not setting the explicit photos to ‘private.’ Surely, he was fucked. Milo really wanted this job. He’d prepared for the interview for nearly a month! Now this amazing opportunity was squashed because of some nude photos? That didn’t seem fair at all.

In the next moment, Mr. Stone changed his tone. The fact of the matter was that he absolutely loved the photos. Mr. Stone admitted that he found Milo’s solo pics to be top notch. The CEO arched an eyebrow as he spoke. His voice remained calm, cool and collected as he casually indicated that the cute twink applicant was just what the company was looking for.

However, there was a catch.

Mr. Stone explained coyly that if Milo gave him a live action demonstration of what was showcased in all of his photos, then he could expect to receive a generous offer from the company.

Mr. Stone, shrewd negotiator that he was, couldn’t help but notice Milo’s pants were getting awfully tight and bulging. Another bead of sweat trickled down the applicant’s face as he processed the situation. The plain truth was that the moment that Milo walked into the interview room and laid eyes on Mr. Stone, he had immediately found the older man to be wildly attractive. The way his form filled out a button-up shirt and slacks was mesmerizing to him.

Mr. Stone saw a look of momentary trepidation in the boy’s eyes. He quickly moved to smooth over any notion that what he had presented to the twink was a ploy or trick. A small smile dared to cross Milo’s lips. Mr. Stone slid closer to where the sweet-faced youth was seated and he encouraged the applicant to rise and remove his belt.

By this point, the throbbing erection straining against the boy’s dress pants was threatening to burst clean through the thin fabric. Mr. Stone gazed up at Milo and made hard eye contact. He then lifted his hand and delicately, gently squeezed the outline of the aroused twink’s massive hard-on.

Milo sucked in a soft breath and steadied himself. His mind raced; what an unexpected turn of events! He wondered how far Mr. Stone intended to go. Before he could complete the thought, Mr. Stone began unzipping the young man’s pants. Milo shivered as who he hoped was his future boss slid Milo’s slacks down and then began caressing his manhood through his underwear.

A thick coating of precum had soaked right through Milo’s thin jockeys. Mr. Stone wiped a generous amount of the silky, sticky boy substance and hungrily licked his fingers clean. It was sweet and decadent, and he smacked his lips.

Soon, Milo’s long, thick member was released from his straining underwear. Mr. Stone made a very audible hum of sheer astonishment and delight. Milo’s monster was very impressive, and disproportionate with his otherwise petite stature.

Mr. Stone licked the underside of Milo’s sensitive cockhead, extracting even more exquisite boy nectar. Mr. Stone gave such skilled and generous oral pleasure that one might come to the conclusion that he was the one angling for a job! Young Milo nearly lost his balance, the pleasure rocked him so.

Mr. Stone sensuously tapped and tweaked his own nipples each time that he came up for air. And Milo, being the observant, hopeful upstart that he was, took over the sensual nipple play. With each swallow of the panting twink’s cock, Milo pleasured his soon-to-be new boss’s nipples.

Mr. Stone realized that he. too, was starting to break a sweat. He pulled Milo’s face to his and fervently kissed him. The applicant massaged Mr. Stone’s thick daddy dick as they made out and continued to twist and tease each other’s nipples.

Then out of seemingly nowhere, Mr. Stone completely stripped, spun around, hopped onto the seat, and stuck his big, buff bottom out. Milo dropped to his knees and pushed Mr. Stone’s ass cheeks apart—the boy definitely had the skills for this job.

The boy’s tongue immediately found the Silver Daddy’s crack. Mr. Stone crooned and howled as he lost all control, his head rolling around and his hands gripping the seat cushions as Milo absolutely went to town. He moaned his approval and encouraged the eager applicant to tongue his hole even more. Milo’s compliance was immediate, and no on-the-job training was needed.

The more that Milo licked the horny CEO’s ass crack, the more he wanted to. Truth be told, the rim job was causing Milo’s hard-on to drool even more. He wanted to fuck the CEO so badly—he was just waiting for the word.

Suddenly, as if reading the boy’s mind, Mr. Stone implored Milo to penetrate him. This was the moment Milo had been waiting for. He quickly greased up his bobbing pole and slicked up the DILF’s puckering hole. Mr. Stone prompted Milo to go slow at first as the boy’s penis was seriously huge.

Milo pushed his head up against Mr. Stone’s smooth, tight man-crevice. The boy emitted a small gasp as he attempted to push in but could only get part of the tip inside. He nearly came right there. This was easily the tightest ass that the young man had ever tried to penetrate.

After several steady, patient minutes Milo was finally able to get most of his cock all the way inside of Mr. Stone’s vise-tight hole. The twink slid in and out—Mr. Stone found this long-dicking technique incredible. And as much as Milo wanted to make hot, steamy love to this beefy body all day, he knew that time was money. Mr. Stone suggested that they change positions and that Milo demonstrate that he could deliver the precious, coveted load that the canny business man longed for.

Milo knew he must capitalize on the moment and prove himself. He drove his cock deep into Mr. Stone’s thick, muscular bottom like a thoroughbred in heat. Milo rode the moaning DILF like his life depended on it, passionately fucking the older man until he felt all control slipping from this grasp.

In the next amazing moment, Milo reared his head back and slammed one last time, as deep into his new boss as he possibly could go. Mr. Stone roared his astonished approval as literally no one had penetrated him as capably as Milo had. His quivering hole tightened around the boy’s sperm-cannon as both reached their pinnacles.

When Milo finally came inside of Mr. Stone, the potency of his orgasm shook the both of them to the core. The twink’s blasts were massive and so forceful that he just about passed out from the intensity. The boy’s body involuntarily convulsed as the pleasure steamrolled through them both.

Mr. Stone gently cupped Milo’s head and kissed him all over his face. He was sure the boy had a bright future at his company. With all of Milo’s skills and obvious talents, Mr. Stone was convinced that he needed to have a close and intimate on-boarding session with his new hire. He wondered if the boy could start…now?

Photos
Series: Milo Miles
Milo Miles series cover
Chapters
1. Job Interview 42mn
Nearly a month ago Milo Miles had sent in a job application to the renowned Stone and Associates Corporation. He got no response initially and, after a few weeks passed, had glumly given up on the possibility of a reply. However, in the fourth week, Milo received a call from Mr. Dillon Stone himself, CEO of the company. He apologized for the lateness of the response, but there had been so many applicants that they were just now getting to reviewing Milo’s resume. Mr. Stone was hoping Milo was still interested in the position and willing to come into the office for an interview. On the morning of the set date, Milo came to Mr. Stone’s office pumped up and ready to impress. He met the successful businessman and gave the interview of his life. Milo was well-spoken, prepared and organized. He answered each of Mr. Stone’s questions with adept knowledge of the business and he thoughtfully presented the ways in which he would be a valued contributor. After the interview concluded, Milo sat nervously in his seat. Mr. Stone had seemed genuinely impressed, oftentimes intrigued even. However, the CEO peered into his laptop occasionally, his gaze lingering at some unknown subject of interest that worried Milo. Was his resume not good enough? After a brief silence, Mr. Stone cleared his throat and closed the laptop. He emphasized that the company was seeking applicants with self-motivated constitutions. They also prized people who could adapt to any situation when called upon. They were especially interested in flexible, versatile types. Mr. Stone believed that from what he could ascertain about Milo during the interview, the young man seemed quite likely to have these qualities and more. But there was something else that the cunning veteran had gathered, as well. Before calling Milo into the office for the interview, Mr. Stone disclosed that he had spent time on the internet doing some casual research on Milo. Mr. Stone let that revelation sink in for a moment. Though Milo stayed still and did his best not to react, Mr. Stone couldn’t help but notice a bead of sweat pop out on the handsome candidate’s smooth brow. Mr. Stone noted that he had discovered an alternate Twitter account that belonged to Milo that displayed images of the boy that were most definitely for ‘mature audiences.’ The bead of sweat on Milo’s brow trickled down the side of his face. Mr. Stone looked his applicant directly in the eye. Milo’s internet photos also showcased himself as a notably very versatile individual with a propensity for pounding on and being pounded by tall, muscular, and of course, very hung DILFs. Milo inwardly kicked himself. How could he have forgotten about that Twitter account? He silently bemoaned not setting the explicit photos to ‘private.’ Surely, he was fucked. Milo really wanted this job. He’d prepared for the interview for nearly a month! Now this amazing opportunity was squashed because of some nude photos? That didn’t seem fair at all. In the next moment, Mr. Stone changed his tone. The fact of the matter was that he absolutely loved the photos. Mr. Stone admitted that he found Milo’s solo pics to be top notch. The CEO arched an eyebrow as he spoke. His voice remained calm, cool and collected as he casually indicated that the cute twink applicant was just what the company was looking for. However, there was a catch. Mr. Stone explained coyly that if Milo gave him a live action demonstration of what was showcased in all of his photos, then he could expect to receive a generous offer from the company. Mr. Stone, shrewd negotiator that he was, couldn’t help but notice Milo’s pants were getting awfully tight and bulging. Another bead of sweat trickled down the applicant’s face as he processed the situation. The plain truth was that the moment that Milo walked into the interview room and laid eyes on Mr. Stone, he had immediately found the older man to be wildly attractive. The way his form filled out a button-up shirt and slacks was mesmerizing to him. Mr. Stone saw a look of momentary trepidation in the boy’s eyes. He quickly moved to smooth over any notion that what he had presented to the twink was a ploy or trick. A small smile dared to cross Milo’s lips. Mr. Stone slid closer to where the sweet-faced youth was seated and he encouraged the applicant to rise and remove his belt. By this point, the throbbing erection straining against the boy’s dress pants was threatening to burst clean through the thin fabric. Mr. Stone gazed up at Milo and made hard eye contact. He then lifted his hand and delicately, gently squeezed the outline of the aroused twink’s massive hard-on. Milo sucked in a soft breath and steadied himself. His mind raced; what an unexpected turn of events! He wondered how far Mr. Stone intended to go. Before he could complete the thought, Mr. Stone began unzipping the young man’s pants. Milo shivered as who he hoped was his future boss slid Milo’s slacks down and then began caressing his manhood through his underwear. A thick coating of precum had soaked right through Milo’s thin jockeys. Mr. Stone wiped a generous amount of the silky, sticky boy substance and hungrily licked his fingers clean. It was sweet and decadent, and he smacked his lips. Soon, Milo’s long, thick member was released from his straining underwear. Mr. Stone made a very audible hum of sheer astonishment and delight. Milo’s monster was very impressive, and disproportionate with his otherwise petite stature. Mr. Stone licked the underside of Milo’s sensitive cockhead, extracting even more exquisite boy nectar. Mr. Stone gave such skilled and generous oral pleasure that one might come to the conclusion that he was the one angling for a job! Young Milo nearly lost his balance, the pleasure rocked him so. Mr. Stone sensuously tapped and tweaked his own nipples each time that he came up for air. And Milo, being the observant, hopeful upstart that he was, took over the sensual nipple play. With each swallow of the panting twink’s cock, Milo pleasured his soon-to-be new boss’s nipples. Mr. Stone realized that he. too, was starting to break a sweat. He pulled Milo’s face to his and fervently kissed him. The applicant massaged Mr. Stone’s thick daddy dick as they made out and continued to twist and tease each other’s nipples. Then out of seemingly nowhere, Mr. Stone completely stripped, spun around, hopped onto the seat, and stuck his big, buff bottom out. Milo dropped to his knees and pushed Mr. Stone’s ass cheeks apart—the boy definitely had the skills for this job. The boy’s tongue immediately found the Silver Daddy’s crack. Mr. Stone crooned and howled as he lost all control, his head rolling around and his hands gripping the seat cushions as Milo absolutely went to town. He moaned his approval and encouraged the eager applicant to tongue his hole even more. Milo’s compliance was immediate, and no on-the-job training was needed. The more that Milo licked the horny CEO’s ass crack, the more he wanted to. Truth be told, the rim job was causing Milo’s hard-on to drool even more. He wanted to fuck the CEO so badly—he was just waiting for the word. Suddenly, as if reading the boy’s mind, Mr. Stone implored Milo to penetrate him. This was the moment Milo had been waiting for. He quickly greased up his bobbing pole and slicked up the DILF’s puckering hole. Mr. Stone prompted Milo to go slow at first as the boy’s penis was seriously huge. Milo pushed his head up against Mr. Stone’s smooth, tight man-crevice. The boy emitted a small gasp as he attempted to push in but could only get part of the tip inside. He nearly came right there. This was easily the tightest ass that the young man had ever tried to penetrate. After several steady, patient minutes Milo was finally able to get most of his cock all the way inside of Mr. Stone’s vise-tight hole. The twink slid in and out—Mr. Stone found this long-dicking technique incredible. And as much as Milo wanted to make hot, steamy love to this beefy body all day, he knew that time was money. Mr. Stone suggested that they change positions and that Milo demonstrate that he could deliver the precious, coveted load that the canny business man longed for. Milo knew he must capitalize on the moment and prove himself. He drove his cock deep into Mr. Stone’s thick, muscular bottom like a thoroughbred in heat. Milo rode the moaning DILF like his life depended on it, passionately fucking the older man until he felt all control slipping from this grasp. In the next amazing moment, Milo reared his head back and slammed one last time, as deep into his new boss as he possibly could go. Mr. Stone roared his astonished approval as literally no one had penetrated him as capably as Milo had. His quivering hole tightened around the boy’s sperm-cannon as both reached their pinnacles. When Milo finally came inside of Mr. Stone, the potency of his orgasm shook the both of them to the core. The twink’s blasts were massive and so forceful that he just about passed out from the intensity. The boy’s body involuntarily convulsed as the pleasure steamrolled through them both. Mr. Stone gently cupped Milo’s head and kissed him all over his face. He was sure the boy had a bright future at his company. With all of Milo’s skills and obvious talents, Mr. Stone was convinced that he needed to have a close and intimate on-boarding session with his new hire. He wondered if the boy could start…now?
2. Mondays 31mn
I arrived bright and early Monday morning at my family business, Stone and Associates, LLC, to get a jump-start on the work week. As I entered the main building, I realized that I wasn’t the first one in. Our new hire, Milo Miles, was already at his desk, typing furiously on his laptop. He had his typical giant mug of coffee, all the while never taking his unblinking eyes off the computer screen. The young man was so lost in the project on his screen that, at first, he didn’t even notice me enter the room. As I approached Milo’s workspace, the handsome Latin twink looked up and smiled. I asked him about his weekend. Milo shrugged and related how he had enjoyed spending time with friends, but not everything that weekend went the way he had planned. Apparently, a fellow that Milo was supposed to meet up with for a date ended up flaking out. I was sympathetic, but I couldn’t help but shake my head in disbelief. Who in their right mind would back out of getting naked with this fine young man? I communicated this sentiment and threw in an extra bit about how the dude who flaked on the boy missed out—big time. Milo blushed. Then, the cheeky twink shrugged and related an interesting detail: he was of the belief that on a previous date the dude had a rather difficult time taking the twink’s very large cock. Milo’s gut told him that the dude chose not to give it another go. Indeed, I knew just how well endowed he was—he’d exposed me to a great many of his gifts and talents (professional and otherwise) during our initial interview together. However, an experienced gent like myself could not only take Milo’s massive length and girth, I absolutely loved it. Craved it, if I’m being perfectly honest here. I glanced at the clock. There was still almost an hour remaining before the rest of my employees would begin to trickle in for the day. I knew the diligent, hard-working boy was neck deep in projects, but I took the plunge anyway and casually suggested that we enjoy a quick romp and fuck those Monday blues away. Milo beamed, nodded, and licked his lips. Next thing I knew, the boy bounced off his chair, we kissed, and his tongue darted passed my lips. We smoldered in one another’s embrace, made out, and groped. As I leaned down and cupped Milo’s ass in my hands, I couldn’t help but feel the steel-hard twink dick in his pants press into me. With little time to spare, I began to unbutton Milo’s dress shirt. I quickly noticed how hard his nipples were, so I leaned down and suckled on one. He took in a sharp, delighted breath. I got a fairly good taste of that delectable nip and it was obvious to me that Milo was getting very hot, indeed. He pulled my face back towards his and laid a juicy wet one on my lips and then pistoned his tongue back inside my mouth again. The young cutie was a terrific kisser. Then the little dude with the big boner tenting and throbbing in his khakis pulled my shirt off. My own nipples were rock-solid by then, and as we continued to make out, he tweaked them just like he did for me during his interview. Suddenly, all I wanted at that moment was Milo’s mouthwatering boy meat. I dropped to my knees and took a second to admire and fondle the twink’s flat abs. His cock throbbed again and again at every touch. I absolutely could not wait to free his erection—nor mine! I fondled Milo’s sizable package and allowed my mouth to roam freely all over the boy’s pubic region. I loved the honey aroma of his private parts and the shuddering moans that emitted as I groped him. When I finally sprung his large lump from his jockeys, I wasted no time engulfing his massive length and girth into my mouth. Before I knew it, the horny twink was fucking my face like there was no tomorrow. Even when Milo shoved that huge cockhead past my throat and triggered my gag reflex, he was undeniably getting off plowing into me. Eventually, I really did need to come up for air. As I quickly caught my breath, the boy’s boner bobbed up and down as though giving my oral skills a happy nod of approval. With a heated, sexy murmur and big, brown, lust-filled eyes, Milo pulled me to my feet. He dropped down to his own knees and with both of his petite, delicate hands and fingers began to massage and lick my dick. God, it felt great! And just as Milo impressed me with his tireless work ethic, he really impressed me with how he could always swallow my entire, pulsating length in one go! But deep down, I knew full well what Milo needed: my thick, tight, DILF bottom. Now I’d be lying if I tried to tell you that I’m too proud to beg. During Milo’s tenure here at my company, everyone knows that I’m the boss. But there’s just something about the gorgeous, insatiable boy that makes me want to immediately hand over the reins. I gave him the nod. He promptly turned me around and bent me over, exposing my ready-and-waiting daddy hole. Cock-sucking isn’t the only amazing talent that Milo has: the manner and techniques in which he laps and licks my puckering crack is always beyond amazing. Milo gobbled up my ass like he hadn’t had anything to eat for days. His ravenous, nearly insatiable lips and tongue enthusiastically ate me out. All I could do was grasp the nearest desktop and hold on for dear life. I found myself wheezing for air and frantically beating my daddy meat. Magically, like Milo could read my mind, he hopped to his feet and slammed that cock all the way inside my ass to the hilt. He knew as well as I did that we needed to move things along because the rest of the workers would begin filing in very soon. Milo and I had just enough sexual experience together at this point where I knew the happy young hunk was close to blowing his wad. His gasps and groans indicated that his throbbing dick needed to explode, and really it should go without saying that I wanted that twink load. Bad. I thought that Milo might’ve begun to jackrabbit my tight, needy hole. Instead, the boy astonished me with yet another talented skill: he could seriously longdick with the best of them. He’d masterfully pull his long length just to the point where his huge cockhead kept contact with my meaty entry. Then we’d both simultaneously holler as he’d slam that sucker right back in, pushing through my tight tunnel and nailing the sweet spot in the deepest part of me. I teased and erotically twisted my daddy nips with each of Milo’s luscious thrusts. The young go-getter was gulping air at this point, as I could tell he was hastening to the finish. All the while, I was beating my meat in time with the boy’s final approach. Then it happened. Milo grabbed me by the waist with both hands and propelled several massive cumshots into my ass. I white-knuckled the edge of the desk and was sure to squeeze my well-fucked love canal like a fist around the twink’s spurting slammer as he continued his cum. Milo held tightly to me as he froze and kept filling me. God, this dude could cum a lot! Maybe I’m just the greedy, slightly overzealous type, but I honestly wished Milo wouldn’t stop shooting. But alas, after eight or nine powerful blasts, the boy’s cock was utterly drained. Then, I had a brilliant thought: maybe we might continue fucking the Mondays away later for morning break…!
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