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Milo miles Chapter 3: staying late

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October 12, 2023 | Full Length Video : 31min 17sec

The hour was growing late—it was almost midnight. Tireless twink Milo Miles and his bustling boss Dillon Stone were the only ones remaining at the office. Major project deadlines were rapidly approaching. Mr. Stone wished that he could split himself into two people because there was still so much to do.

The businessman finally ripped himself away from his laptop, sighed, and rubbed his tired eyes. He looked across the work table that he and Milo shared—the boy was still intensely engaged. Mr. Stone chuckled. Oh, to be young and full of energy like that again!

Milo’s furious ...More

Milo’s furious typing finally tapered off. He looked up at Mr. Stone, who was silently admiring the hardworking lad. Milo blushed—he truly worshiped Mr. Stone. The boy wanted nothing more than to emulate his professionalism and work habits.

Mr. Stone thanked Milo again for staying late with him to help catch up on the workload. Milo humbly shrugged; he loved any opportunity to be close to Mr. Stone, and if that meant working 14-hour shifts, then so be it. It was truly his honor to be depended upon such as he was.

Mr. Stone yawned and sat back in his chair. Milo suggested that they take a break. Not that Mr. Stone needed permission, but he was extra glad that his compassionate colleague spoke up. Sometimes, the boss couldn’t figure out how to force himself to slow down and take a moment.

Milo cleared his throat and shot his sexy superior a knowing look. Mr. Stone cocked an eyebrow and waited for the boy to speak up. Milo casually suggested that the two of them have some "fun," maybe even blow off a little steam.

Mr. Stone immediately snapped his laptop shut and emitted a long, low murmur. Milo rose to his feet and slowly sauntered around the worktable, never taking his radiant, randy eyes off the man he called his superior.

In only a second, Milo was on top of the seated DILF and kissed him hard on the lips. Mr. Stone moaned as Milo felt him up. Soon, their shirts were unbuttoned and these aroused coworkers passionately locked lips.

As the lust-driven duo groped and made out, Mr. Stone couldn’t help but notice that Milo was rock-hard. He wondered if the boy’s long, disproportionate member might tear through the soft fabric of his work slacks. He helped Milo remove his pants and jockeys to pull that pulsating boy-rod out of captivity.

And for his part, Mr. Stone was just as hard—almost painfully so. The bulging boss dropped to his knees and grasped Milo’s bobbing boner. Mr. Stone licked all of the dribbling precum clean off of Milo’s cock and then swallowed the shaft down to the pubes in one go.

Then Milo showed off some of his own unique and talented oral propensity by dropping to his knees and delivering the sloppiest, deepest blowjob that the goal-oriented go-getter could give.

Mr. Stone howled his approval as mere pleasure morphed into near-animal lust. The DILF had finally found his second-wind. He grabbed Milo by the head and eagerly face-fucked the fine Latin boy.

All too soon, it seemed, Milo came up for air and asked his sexy superior if he would care to have his tight, DILF-hole licked. Didn’t have to ask daddy twice! As far as Mr. Stone was concerned, he secretly wished Milo had a clone so he could have the boy simultaneously lick his cock and his hole!

Either way, Mr. Stone couldn’t wait a moment longer to have Milo make out with his ass. The dude really got into it, and each time that the boy rimmed the old vet it felt like the first time.

Truth be told, Milo knew full well by now that the ecstatic elder would need to cum soon. Once the twink’s tongue was buried inside that savory bottom, Mr. Stone wasn’t one to last all that long.

The moment that Mr. Stone’s tight anus clenched around Milo’s wet, groping tongue, they both knew that it wouldn’t be much longer. Milo begrudgingly pulled his hungry mouth off of Mr. Stone’s meaty backside. Next, he stood up, slicked up his bobbing boner, and aimed it towards the panting daddy’s hole.

Milo fucked Mr. Stone so good and so hard, and right in the tender sweet spot, deep inside. Mr. Stone needed to cum and he needed to cum badly. He begged his coworker to flip him over so Milo could fuck his boss on his back. Mr. Stone had, indeed, reached his limit. The twink really put his back into it and rammed over and over again.

Mr. Stone’s orgasm blasted out of his cock like a rocket shot. Hot daddy semen spewed everywhere. The sight of that hot action caused Milo to convulse, quickly pull out and shoot his own massive, juicy load all over Mr. Stone’s shaft and testes.

Sweat and cum glistened all over Mr. Stone’s furry chest and abs. His mind raced with the passionate intensity of both his own climax as well as that of the skilled upstart’s. The two kissed and held each other close.

Milo and Mr. Stone locked eyes. Did they really have to go back to work…?

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COACH STONE

Coach is a gray-haired, hugely handsome DILF with a muscular, tanned body and a dick to die for. He’s new to the league and on the lookout for recruits. No experience necessary. He knows when a boy has potential and is a master in the art of releasing a young man’s inner top.

Played by Dillon Stone
MILO MILES

Milo, a young, petite, charming Latin man, is excited for his job interview. But when his private social media account—full of adult pictures of himself—is found by the CEO, he’s devastated and certain he’s about to lose out on the chance of a lifetime. However, the CEO’s interest in Milo’s private identity isn’t the disqualification the young applicant may think it is…

Played by Milo Miles
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Milo Miles

Milo Miles: 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…!
3. Staying Late 32mn
The hour was growing late—it was almost midnight. Tireless twink Milo Miles and his bustling boss Dillon Stone were the only ones remaining at the office. Major project deadlines were rapidly approaching. Mr. Stone wished that he could split himself into two people because there was still so much to do. The businessman finally ripped himself away from his laptop, sighed, and rubbed his tired eyes. He looked across the work table that he and Milo shared—the boy was still intensely engaged. Mr. Stone chuckled. Oh, to be young and full of energy like that again! Milo’s furious typing finally tapered off. He looked up at Mr. Stone, who was silently admiring the hardworking lad. Milo blushed—he truly worshiped Mr. Stone. The boy wanted nothing more than to emulate his professionalism and work habits. Mr. Stone thanked Milo again for staying late with him to help catch up on the workload. Milo humbly shrugged; he loved any opportunity to be close to Mr. Stone, and if that meant working 14-hour shifts, then so be it. It was truly his honor to be depended upon such as he was. Mr. Stone yawned and sat back in his chair. Milo suggested that they take a break. Not that Mr. Stone needed permission, but he was extra glad that his compassionate colleague spoke up. Sometimes, the boss couldn’t figure out how to force himself to slow down and take a moment. Milo cleared his throat and shot his sexy superior a knowing look. Mr. Stone cocked an eyebrow and waited for the boy to speak up. Milo casually suggested that the two of them have some "fun," maybe even blow off a little steam. Mr. Stone immediately snapped his laptop shut and emitted a long, low murmur. Milo rose to his feet and slowly sauntered around the worktable, never taking his radiant, randy eyes off the man he called his superior. In only a second, Milo was on top of the seated DILF and kissed him hard on the lips. Mr. Stone moaned as Milo felt him up. Soon, their shirts were unbuttoned and these aroused coworkers passionately locked lips. As the lust-driven duo groped and made out, Mr. Stone couldn’t help but notice that Milo was rock-hard. He wondered if the boy’s long, disproportionate member might tear through the soft fabric of his work slacks. He helped Milo remove his pants and jockeys to pull that pulsating boy-rod out of captivity. And for his part, Mr. Stone was just as hard—almost painfully so. The bulging boss dropped to his knees and grasped Milo’s bobbing boner. Mr. Stone licked all of the dribbling precum clean off of Milo’s cock and then swallowed the shaft down to the pubes in one go. Then Milo showed off some of his own unique and talented oral propensity by dropping to his knees and delivering the sloppiest, deepest blowjob that the goal-oriented go-getter could give. Mr. Stone howled his approval as mere pleasure morphed into near-animal lust. The DILF had finally found his second-wind. He grabbed Milo by the head and eagerly face-fucked the fine Latin boy. All too soon, it seemed, Milo came up for air and asked his sexy superior if he would care to have his tight, DILF-hole licked. Didn’t have to ask daddy twice! As far as Mr. Stone was concerned, he secretly wished Milo had a clone so he could have the boy simultaneously lick his cock and his hole! Either way, Mr. Stone couldn’t wait a moment longer to have Milo make out with his ass. The dude really got into it, and each time that the boy rimmed the old vet it felt like the first time. Truth be told, Milo knew full well by now that the ecstatic elder would need to cum soon. Once the twink’s tongue was buried inside that savory bottom, Mr. Stone wasn’t one to last all that long. The moment that Mr. Stone’s tight anus clenched around Milo’s wet, groping tongue, they both knew that it wouldn’t be much longer. Milo begrudgingly pulled his hungry mouth off of Mr. Stone’s meaty backside. Next, he stood up, slicked up his bobbing boner, and aimed it towards the panting daddy’s hole. Milo fucked Mr. Stone so good and so hard, and right in the tender sweet spot, deep inside. Mr. Stone needed to cum and he needed to cum badly. He begged his coworker to flip him over so Milo could fuck his boss on his back. Mr. Stone had, indeed, reached his limit. The twink really put his back into it and rammed over and over again. Mr. Stone’s orgasm blasted out of his cock like a rocket shot. Hot daddy semen spewed everywhere. The sight of that hot action caused Milo to convulse, quickly pull out and shoot his own massive, juicy load all over Mr. Stone’s shaft and testes. Sweat and cum glistened all over Mr. Stone’s furry chest and abs. His mind raced with the passionate intensity of both his own climax as well as that of the skilled upstart’s. The two kissed and held each other close. Milo and Mr. Stone locked eyes. Did they really have to go back to work…?
4. Back from the Gym 20mn
Milo has grown very comfortable with his new schedule while working at Stone and Associates, LLC. Having a good handle on his workload and being the boss’s new personal favorite, he tries to squeeze in a workout over his lunch hour. Due to his break only being an hour long, Milo is struggling to figure out a routine that fully utilizes his time as well as giving himself a full body workout. So, he seeks out the help of his new trainer Cole. Cole is around the same age as Milo and the two hit it off. They continue to meet up over Milo’s lunch hours for their workout in the following days. The boys struck up a conversation one day about what each of their types were after Milo had made some comments at the gym about some of the older guys. It was then that Cole admits he is very much attracted to older guys, but found that they sometimes want nothing to do with guys his age. Milo has decided that since Cole has been nice enough to take him up on his offer regarding the lunch hour workouts, that he will return the favor and help his new friend get laid. Afterall, he did have the boss in his back pocket! The two boys finish at the gym and that’s when Milo makes Cole the offer to drop by his place of work. He shares with him that he has been sleeping with his boss, and not only that, but that Mr. Stone couldn’t think straight without getting fucked first! Milo has been enjoying being the dominant one in the office so much that he recently thought about sharing the boss. He’s sure Mr. Stone wouldn’t be able to say no to another young stud like Cole! Both Milo and Cole make their way to Stone and Associates, LLC. Their young cocks bulge behind their jockstraps as they anticipate initiating the plan. Mr. Stone sits on a couch and after introducing Cole to him, Milo receives a compliment on how he looks in his gym clothes. The latino top makes a remark about wanting to remove his clothes and slowly strips off his shorts to reveal his hard cock, desperate to break free from its jockstrap. Mr. Stone calls Cole over as both boys take either side of the older man. He pulls down their jockstraps at the same time, immediately overwhelmed by having two hot twink cocks before him. He isn’t sure whether or not to dive onto the new boy’s hardon first, so he sucks Milo’s cock into his mouth. The older man’s curiosity takes over, however, and he quickly throws his mouth onto the other twink’s big dick. He switches between both boys, savoring the uniquely different taste of each of them. Both twinks remain hard as Mr. Stone strips off his clothing to reveal his own boner poking out from his underwear. He uses his big strong arms to pull each of the boys closer to him so they can exchange kisses. His own underwear makes its way off of him during the exchange, releasing his thick cock from the fabric prison. The moment Mr. Stone is free, he is swiftly bent over by Milo to have his hole eaten. Cole strokes his big cock watching his gym friend rimming the boss’s hole. The taller boy is so excited that he swaps positions with Milo to get a taste of the older man’s ass. Milo is ravenous and uses this opportunity to plant his face in between Cole’s smooth cheeks so he can continue rimming. They are together now, a line of masculine taste. All the excitement has Cole’s big dick throbbing to get inside. Being told by Milo that Mr. Stone is a fan of his long dicking, Cole wastes no time in sinking his cock deep into the horny bottom. The DILF spread his ass open in warm welcome of the big dick. The sensation forces moans from him, the kind that are wholly inappropriate for a work environment. The latino top is horny as all hell watching his buddy making every inch of that big cock disappear inside of his boss. Mr. Stone’s moans are sending Milo’s cock into rock hard territory. Cole seems to enjoy it when he has his tongue up there, was it possible he might enjoy Milo’s cock, too? Sure enough, after a little lubrication, Milo felt his cock slip into Cole’s ass. At first Cole is overpowered by Milo’s intense rhythm, allowing himself to be pushed forward into Mr Stone’s hole by the thrusts. Yet soon enough both boys begin thrusting together, to allow their cocks to sink deeper as they pump their throbbing members. The couch becomes a mess of limbs as all three men groan in pleasure, holes being filled to the brim with young boy dick. Having enjoyed being on the floor with both boys on either side of him, Mr Stone urges the two twinks to blow their loads all over his chest. Wanting to take full advantage of the opportunity of having two cocks rather than just one, he wants a chest full of younger boy spunk to remember this encounter. Both Milo and Cole assume the position and begin to stroke their twink cocks over the horny older man. Mr Stone looks up at Milo still with his face a little covered in Cole’s cum, and Milo realizes that they were perhaps overdue for a little more help around the office.
5. New Recruit 16mn
The winter tryouts for the upcoming baseball season were underway. This is one of my favorite times of the year, as our team sees a lot of young, athletic hopefuls trying to earn a spot on the roster. As I had just been promoted to assistant coach, it was my responsibility to evaluate each tryout and analyze their performance on the practice field. Our newest prospect, Milo, was scheduled for a special counseling session that would help determine not only his physical condition and prowess, but also if he had that ‘it’ factor. I have an inherent knack for picking up on an athlete’s special qualities that even some of the most experienced coaches might not catch. Upon first meeting Milo, right away I liked his eagerness and his enthusiasm. It’s plain as day that he loves the sport, craves competition, and will do almost anything to ready himself for gameday. I also observed that he and a few of the other older coaches spent a lot of extra one-on-one time together. Turns out their frequent sessions involved more than just a review of the playbook! So on the afternoon of Milo’s interview, he was ready to impress. Afterwards, I couldn’t help but offer an invite back to my place. I had some additional questions and feedback I wanted to go over with him. My dick jumped in my jockeys when Milo shot me a happy grin. He did not hide his excitement whatsoever. Once we arrived back at my place, we got comfortable and chit-chatted for a bit. I noticed that Milo couldn’t resist looking me up and down after I’d casually plopped down on my bed. Without me even needing to give him an invitation, Milo hopped up onto the mattress and sat right next to me. Before he could make a move, I put my hand up and asked if what I’d heard about him was true. Coach Stone had relayed to me that the previous evening he’d enjoyed a rather pleasant time with the youngster—and had been worked over several times all night long. Milo simply batted his pretty eyelids. The boy thought to himself for a moment and then, with a curious tone, inquired if I had ever been with Coach Stone. I casually admitted that I had. I could only chuckle when relaying to Milo that he wasn’t the only tryout that Stone had seduced. Milo seemed a bit surprised by this revelation, but quickly moved on from it and inched a little closer to me. I had a funny feeling that the mattress was likely going to get a good workout of its own! So I took the plunge and asked Milo if he wanted to have a little rough-and-tumble together. The eager boy’s eyes lit up and he licked his lips. He said that he wanted to get me naked and possibly dick me down, if I was into it. I thought that boy’s hard-on was going to rip right through the front! The little Latin hottie has the build of a boy, but the cock of a prize bull. I tenderly kissed up and down his tight, rock-hard abs. Milo hissed with every swipe of my tongue anywhere that I cared to lick. Every time that I glanced at his dick, it just kept getting harder and longer! I just had to suck on it. Milo felt like he had to ask first before he licked my hole. Fuck yeah it’s okay! Once he got started, you’da thought he was devouring ambrosia after a week with no food in the desert! The boy kept saying how good I tasted. I just gripped the bedsheets, threw my head back, and rallied him on. Once Milo had my hole all lathered up and slick with his saliva, he meekly asked permission to put his poundstick deep inside. Of course I said yes. I have to admit, when I say Milo has a disproportionately large penis compared to his body-size and build, I’m not lying. I honestly could barely get two hands around his sizable shaft while I was sucking him off. Either way, by the time the titillated twink had finally squeezed his cock all the way inside me I felt as full up to capacity as I had experienced in recent memory. Plenty of other top tryout hopefuls had put their sluggers inside, but Milo’s was something else entirely—and it felt fucking awesome! Must have felt pretty top-notch for the boy as well. Milo kept saying, moaning about how good it felt. I praised the boy for his talent at nailing my sweet spot, and to continue doing so for as long as he could hold out. His subsequent fuck thrusts sent us both into primal overdrive. The young top slammed my boy-hungry hole and kept me rock hard and ready to blow. Suddenly, a powerful urge overcame me and I begged Milo to flip me over so that I could watch him blast his honey everywhere. No sooner had the words been uttered did he lay me out and shoot his load. I knew from what Coach Stone had told me about the night before that Milo had cum many, many times. But the cumshot that coated my chest and abs seemed to me like two weeks worth. That sight was all it took for my own cock; I erupted with volley-after-volley of hot semen. Spent and exhausted, Milo collapsed on top of me. I held the young superstar-in-the-making close. The delicious aroma of our sex, sweat, and cum was all I needed to confirm that not only was the boy’s future bright, but all of our teammates and coaches would feel the same way in time…!
6. New Recruit 22mn
The annual baseball tournament was just underway and the team was scheduled to play in the deep-south of Florida for the first round. The flight took us as far as Jacksonville, then we had to bus it to the outskirts of this humid swamp-town where the tourney would be held. Needless to say, by the time we got to the hotel, all us players and coaches were heat-sapped, our sweaty bodies sticking to our uniforms. Each player had been assigned a coach roommate to bunk with during our stay. I was more than a little surprised to find out that I would be sharing a room with the strict and demanding Coach Barrett. To be perfectly honest, I always had the impression that he didn’t like me much and found my upbeat spirit a tad annoying. After checking in at reception, Coach Barrett led me down the hallway to our room. I stayed quiet, not knowing what to expect. As we entered the tiny quarters, I couldn’t help but notice that there was only one bed–and a small one at that. Sheesh, I thought, I’ll be sleeping on the floor, I guess… And that’s when things took a turn that was entirely unexpected. Coach Barrett placed a warm, gentle hand on my shoulder and winked. With a surprisingly soft-spoken, musical voice, he asked if I minded that I had to share a room with him. I swallowed hard, then offered a bright smile. Who would have thought that this stern, unabashedly disciplinarian figure could be...disarming? And that smile. I was certain I’d never seen that before. I was suddenly overcome with a surge of giddiness. I hopped up onto the bed and with breathless anticipation waited for Coach Barrett to say something else. My jaw fell into my lap as he began to peel off his clothing and casually informed me that he was going to take a quick shower. With pure awe and a quickly rising lump in my shorts, I marveled as Coach Barrett stripped completely naked and tossed his jockeys just a few feet away from me. His thick shaft—flaccid and beautiful—hung and swung like a horsecock. I wanted so badly to touch it, but instead, I casually began to touch my own. I wondered if Coach could tell, or even cared, how aroused I was getting. Then he was out of sight and into the shower stall. I closed my eyes and listened to the water streaming. It must certainly have felt refreshing and invigorating after that hours-and-hours long bus ride with no air conditioning. I imagined Coach Barrett washing his supremely fit, lean, hairy body from handsome head to fantastic foot. Suddenly, I heard a small cough and I snapped my eyes back open. I realized that I’d drifted off, vividly engrossed in my fantasy. I really had no idea how much time had passed, but Coach Barrett was finished with his shower and toweled dry. Coach Barrett laid down on the bed right next to me and looked me up and down. That sexy, furry body was driving me absolutely wild! I quietly breathed in the freshly scrubbed DILF’s intoxicating aroma. I managed to squeak out the fact that I adored his body hair…and wondered if I could touch it? Coach Barrett inched closer to me and simply nodded. I thought I’d reached maximum body temperature out in the Florida humidity, but damn, I was really hot now. I peeled my shirt off and tossed it to the floor. Half a second later, we were feeling each other up, admiring one another’s bodies. Coach Barrett gently stroked my inner thigh as I ran my trembling fingers through his incredibly soft chest hair. I started rubbing my aching cock over my shorts with my free hand. Lord Almighty, I was horny! Next, his towel came off. We started making out and I stroked his cock fully erect. I could hardly stand it anymore. I desperately needed to cum. I confessed this to Coach Barrett and he offered a knowing smile. He assured me that he’d be happy to help with getting me off—however I liked. Well, since he was sincerely asking, I batted my eyes and asked him to let me fuck him…please? Coach Barrett arched an eyebrow. My face immediately flushed crimson, thinking that I’d overstepped, but to my delight, he merely got into the doggy position. He exposed his luscious daddy hole and instructed me to get it ready. Didn’t need to ask me twice! I dove right in, moaning loudly as the taste of a hot dude's hole is truly second to none. I got right to lapping, licking, and juicing up that savory entrance just as slick and wet as I could. Apparently, the lust-driven rim job I administered got the happy DILF’s desires hot, as well. Soon, Coach Barrett and I were like two beasts in heat, sucking and fucking with carnivore-crazed hunger. At one point, Coach Barrett made me pull out and he pushed me onto my back. Like a panther, he leapt onto my cock—purring, yowling, and hissing as his tight hole sunk all the way down on my boy rod. Then he started really riding me! All too soon, however, I lost control and sent a huge load up inside of him. Coach Barrett squeezed his well-fucked love tunnel and milked every last drop of semen out of me. I was involuntarily shuddering, spasming, my dick non-stop convulsing with ecstasy. I ran my hands and fingers up the sighing DILF’s hairy abs and torso, savoring every second of our shared climax together. Fuck, dude. I sincerely hoped we would share a room from here on out during every road trip…!
7. Casual Fridays 37mn
What a busy week! My company, Stone and Associates, had taken on a few new clients and the workload was insane. I’d been getting as much done as possible on this particular Friday so I could truly enjoy my weekend. Thankfully, I had my loyal associate Milo at my side and we worked together on projects right up until quitting time. I shut my laptop off, pushed my chair back, took a deep breath and stretched. I chuckled to myself as Milo glanced up at me, took another big swig of his seemingly never ending cup of coffee and kept hammering on his laptop. I clicked my tongue and then sighed. I offered a bright “TGIF” to no one in particular. Milo looked up again and cocked his head. He asked if I had special plans for the evening. I noted it was Happy Hour, but I didn’t really have anything specific laid out. I inquired about Milo’s own plans: he shrugged and confessed that he didn’t really have much going on, either. Good boy. I truly appreciate how casual and flexible the cute twink can be with his time. Honestly, all I really wanted was another hot serving of Milo’s huge, gorgeous cock deep inside me. And truth be told, I was kind of amazed we hadn’t already been naughty together this week. Well, I hoped that was going to change. I casually suggested that we kick the weekend off with a “bang.” Suddenly, Milo snapped off his own laptop, rose to his feet, and beamed while licking his lips. Wasn’t but half a second later and the sexy twink had his arms around my neck and his tongue immediately slipped inside my mouth. As we fondled, groped, and made out, the boy and I made pretty quick work of freeing one another’s cocks. Milo and I were both hard and getting harder—especially during some really hot mutual frottage. I should note that while Milo is around five foot nothing, his genitalia is nearly as long as he is tall. And that boy’s girth, fuck. Let’s just say the gorgeous Latin twink is one of the more well-endowed fellas I’ve had the pleasure of knowing. And I’ll be honest, the pleasures that the boy and I engaged upon that evening in the office went well beyond enjoying his enormous cock! You see, we’d barely slipped our pants off and Milo immediately got down on his knees and started lapping at my own sizable stiffy. I murmured and blew hot steam as I stroked the boy’s pretty face. He’s really into cocksucking, too. I love it when Milo gets into a heart pounding deep-throat rhythm. I might have succumbed to releasing my pent-up seed down into the Latin hottie’s belly, but the sexy, unpredictable upstart rose to his feet and nodded up at me while swinging his thick boy rod around. I could only venture a guess that he wanted some head, too! Finally, Milo’s shirt came flying off as the temperature in the room really started to rise. I sucked the humming, hollering twink’s huge dick and got to moaning uncontrollably myself. I adore how Milo’s cock throbs in response to the way my tongue swirls around his glans. I can taste the sweet precum, too. It really didn’t feel like my coworker and I had been trading head for very long, and the next thing I know is the boy has got me spun around and holding on for dear life. To hold steady, my hands were summarily pressed up against the wall. Then Milo spread my ass cheeks and plunged his tongue immediately into my hole. I pressed my ass back and gave the horny stud all the access he could want. I threw my head back and hollered as a result of the intense sensations of Milo’s hungry tongue licking the tender, meaty entry of my fuck tunnel. He was getting me all wet down there real quick. I knew exactly what the boy was prepping me for. Eventually, Milo slicked up his swollen erection and squeezed that massive girth right in. As usual, the sweat started trickling down my face as the boy’s huge dick filled my insides up to capacity. Once my fuck hole got nice and loosened up, Milo really started to go to town on my ass. The young top has a penchant for long-dicking and, by God, the talented professional knows how to make a daddy gasp, squeal, and beg for more. After that, we got down onto the floor where Milo put me into the doggy position. I loved the sight of our clothes flung all over everywhere and I fought a primal urge to stroke my own rigid DILF meat off with the boy’s sexy underwear. My hole must have been really tight, because every time I looked back at Milo’s face, he was wide-eyed and crooning—his tongue nearly hanging out of his pretty mouth with every thrust into my ass. Soon, it got to a point where the wailing twink was barely hanging into it. His previously well-timed fuck rhythm was starting to get a little herky-jerky. As he slammed his cockhead into my ass, driving as deep as he could—hitting my sweet spot as he frantically plunged—I could feel the end nearing quickly for both of us. Milo grabbed a hold of my waist and jackhammered my hole like a wild man. He was damn near frothing at the mouth, his lust-crazed desire overtaking any notion of control. Then he came. I could feel thick ropes of semen blasts enter my well-fucked hole. In the meantime, I was honestly barely conscious as the mindblowing sensations rocked my entire being. The boy hung on the best he could during his powerful, shuddering orgasm, but he inevitably let go and collapsed on top of me. In the meantime, I could feel Milo’s hot, gulping breaths against my sweaty skin. No words were spoken—none necessary…
8. Performance Review 24mn
With the fiscal quarter coming to a close Mr. Stone and I have been hard-at-work to ensure that all our paperwork gets properly submitted to finish off another successful year. Having uploaded my final document, I was feeling good about what I had accomplished. That was when my boss gave me the heads-up that since we were coming to the end of the year, that it meant it was time for my first performance review. There was an air of ‘wink-wink nudge-nudge’ with that reminder. Something told me I wouldn’t be preparing for it the same way most other employees would. It was hard to believe it had already been one year since being hired at Stone & Associates and I ended up learning a lot more than I bargained for while in this role. The connection established between me and Mr. Stone had gotten stronger and stronger the more we worked together. But if there was one thing I could always count on, it was if we worked hard enough we would soon end up playing together even harder. One thing I enjoyed about Mr. Stone was that he tried his best to make things as casual in the workplace as possible. It made it a much more enjoyable experience for both of us. We went through the standard protocol, thanking me for my loyalty to the company and letting me know there was little to critique. When it came time for him to ask me the question about if there was anything else I was looking for, however, I could see the naughty glimmer appear behind those blue eyes of his. Mr. Stone fills the gap on the couch and his big hands slide between my office slacks. I pull my boss in for a kiss and our tongues plunge into each other’s mouth. He pulls my pants down just enough to gain access to my thick, hardened cock. Next thing I know, Mr. Stone is on his knees, hungrily shoving every inch of my large Latin lovestick into his mouth. I’ve never been able to hide the pleasure I get from having my cock worshiped by him; he sends me to cloud-nine every single time. We peel off our clothes without even thinking. I watch as my muscular DILF of a boss bends his big ass over the couch, presenting his pink entrance to me. My tongue enthusiastically laps at the opening, savoring the taste. It wiggling between Mr. Stone’s smooth ass cheeks forced deep moans from him. I assume the position we’ve found ourselves in so many times before. I line my still throbbing hard cock against that beautiful bottom. My thick mushroom head pushes forward, penetrating my boss’ hole as our bodies start to move without thought. Mr. Stone takes it effortlessly, stroking his own cock feverishly as I feed him more of mine. When I get him on his back is when my hips really start to pick up the pace. My boss’ ass is milking my cock so well I’m able to find his spot and really pound it into submission. Mr. Stone gets that wrinkle above his brow that tells me he’s about to shoot, but I can’t seem to stop myself, I just keep pushing my cock forward like he’s trained me to. He blows his load with my cock still gliding in and out of his hole, and that’s when my preparation for this review was on full display. I made sure I would deposit a larger load than usual into him; I had forced myself not to jerk off for days. When it came time for me to cum, I left his beefy DILF hole leaking with my DNA. How’s that for going above and beyond at work?
9. New Muscles 23mn
Baseball season is coming up soon. I don’t think I have to worry about my place on the team since I’m fucking most of the coaches. That’s not enough for me, though; I want to pull my weight. Besides, if I’m not good on the field, the guys will speculate on why I’m there, and I gotta keep my special relationship with the Coaches needs to stay secret. Cole, the assistant Coach as well as my friend, suggested that I go talk to Lawson James. Coach James is a personal trainer. Cole says that he likes helping young athletes and offers them an affordable deal. I set up an appointment and, oh god, he’s hot! Not just good looking; Coach James is a walking wet dream. First he had me fill out a questionnaire. It was pages long and took forever, but I was impressed with his thoroughness. Some of the questions were things I had to think hard about because nobody had asked them before. When I was done, we sat down on his sofa and he read over my answers. He seemed pleased enough. Even though I’m not where I would like to be, physically, I take care of myself and exercise regularly, and I know the game. He said it all looked good, and then he asked what I wanted to work on. That was another question I didn’t expect. I mean, I want to get bigger all over, I guess. Playing baseball doesn’t just use one set of muscles. After not enough thought, I added that I wanted to work on my backside, too. I almost regretted it when I heard myself say it. Like, where did that come from? I have kind of been thinking about it, though. I like fucking older guys… a lot! But, I really am versatile. I think, at this point, my dick is more impressive than my ass and everybody just thinks of me as a top. Maybe, if I pump it up some, guys might be more interested. Coach James wasn’t phased. He said, “That’s easy.” He told me to do some squats, and gave me directions on my form. Then he started showing me how to do them correctly. My knees went so weak that I almost fell off of the couch. The Coach’s ass is incredible! It might be the sexiest one I’ve ever seen. It’s like he has two rock-hard melons in his gym shorts. He stood back up and said, “Maybe you’ll have an ass like this one day.” All I could think was, “I want yours now!” Forget being versatile, I wanted to fuck this hot DILF’s perfect ass into next week. I just stood there, not knowing what to say. Cole said Coach James likes cute young athletes. Was he flirting with me? If he was, what did he want? I was up for pretty much anything. He just stood there with a half-smile on his face. It was clear that he expected me to make the first move, so I did. I stepped up to him and kissed him. He met me halfway and, after a minute, started undressing me. I still wasn’t entirely sure where things were going, but he was on his knees giving me one of the best blow jobs I’ve ever had. It was all I could do not to blow my load down his throat, but I really wanted to see where this was going. When he stood up and bent over the couch, I knew what he wanted, and I was more than happy to give it to him. Everybody expects alpha men like Coach James to be tops, but sometimes they like to get fucked, too. I pulled his tight gym shorts down and revealed one of the most gorgeous furry asses that I’ve ever seen. Even when I pulled his cheeks apart, I could barely see his hole in the nest of black fur in his crack. My tongue found it, though. I’m not sure which of us was moaning louder while I got him ready for my fat twink dick. When I pushed my cock into him, he squeezed it so hard that it almost hurt. I took my time fucking him. I wanted both of us to enjoy this just as long as possible. Coach James was snorting like a bull while I rode him and I was moaning and panting as his hole drove me crazy. Finally, it was all just too much. My balls were going to explode whether I was ready or not.
10. Introductions 24mn
Part of the reason Coach James hired Coach Tomas is because he knew this new assistant was one of those hardcore bottoms that, too often, get mistaken for tops just because of their build. He figured his horny players would love another hunky fuck-toy. Coach Tomas would certainly be in heaven with all of those horny young jocks fighting to get into his beefy ass. Of course, Coach Tomas is a good coach, too: he really cares about his players, whether they are on the field or in the sack. Milo Miles loves baseball, and he’s pretty good at it. What he lacks in stature, he makes up for with enthusiasm. Fortunately for Milo, on this team height and batting average are not the only ways to make the line up. Milo’s baseball skills might be average, but he handles the huge bat between his legs like a real slugger. The team’s new assistant coach has already heard about little Milo’s many talents and he can’t wait to open up for the hot young jock. Coach James had already filled Coach Tomas in on his own relationship with the insatiable shortstop. Milo unexpectedly wandered in while Coach Tomas was looking over the team roster. You can tell Coach Tomas was very happy to finally meet Milo. He’s just as sexy as the other Coaches described him. Milo was a bit caught off guard when the handsome stranger not only turned out to be the new assistant Coach, but also knew about his relationship with the head Coach. Milo thought that was supposed to be a secret. It’s fine with Milo if that means he gets to take this hot, beefy bear-ass for a lap around the bases. Milo dropped his shorts and jockstrap, allowing his new Coach to slobber all over his throbbing twink cock. As soon as Milo was ready to more, Coach Tomas went ass-up, begging for dick. Being the team player that he is, Milo was more than happy to pitch in. The cute twink climbed on top of his beefy Coach and shoved his hard cock into the man’s hungry hole. Milo fucks with the carnal enthusiasm that healthy young athletes have for a hungry hole. Coach Tomas’ eager hole is in paradise. This cute Latin twink really gave the Coach a pounding. Milo would have liked to fuck his hot coach all afternoon, but his heavy nuts couldn’t hold it in any longer. He pulled out and shot his load all over his Coach’s beefy buns. Then, like the team player he is, Milo scooped his cum up on the end of his still hard cock and shoved it deep into his Coach’s hole, putting both a groan in Coach Tomas’ throat and a smile on his face. Coach Tomas is now thinking Milo shows a lot of promise but the boy is going to need some regular “practice sessions” to build up his stamina for long distance performance.
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