Onboarding (Suggested Story)

Ben thought the arrangement was rather strange. He’d been hired to do remote work for companies before, and usually all of the training was done remote as well—usually some combination of videos he’d have to watch, and some training sessions with a manager over zoom. This was the first time a boss told him that the training would have to be done in person. Even more unconventional, his boss, who lived in the same city as he did, told him that the training would take place at his home, rather than at an office, mostly because the company didn’t have any regional facilities they could use. It all seemed like overkill for a job he figured would be little more than data entry. The pay was decent though, as were the benefits, so he agreed to head to his new manager’s house on Monday to begin training.

He arrived at the rather non-nondescript house in the suburbs outside of the city, pulled into the driveway, walked up and knocked on the door, adjusting his shirt, and wondering if he’d under-dressed. He hadn’t been to work with someone in so long, he wondered if his polo and slacks would be professional enough. At home, he usually did his remote work in casual attire, but now he was beginning to have some doubts. The door opened after a few moments, and he found himself face to face with a massive gut. The man in the doorway, Mr. Evans, he supposed, loomed over Ben by several inches, and was wearing a button down shirt, tie, and jacket—all while smoking a sizable cigar. He looked Ben up and down with a rather piercing gaze, and then gruffly brought him inside. The interior was fairly minimal, and Ben made a little small talk as they got set up his manager’s study. He asked him if he had any family, and the man said that he didn’t, and left it at that. Ben ended up in front of the computer, Mr. Evans opened up the training program, and that was really the last thing he remembered clearly from that first day. He knew he’d learned a lot—about the company, about his role, but the time just seemed to fly by, and before he knew it, it was evening, and Mr. Evans escorted him back out, telling him he’d need another day of training tomorrow.

For his entire commute home though, Ben found it difficult to think about anything other than Mr. Evans. The man’s smoking had initially disgusted him, as had the man’s substantial, chubby frame, but now that he thought about it, he actually thought it suited him quite well. As someone in charge of others, it gave him a certain air of authority, which Ben found that he lacked himself, with his shorter, thinner frame. The thoughts only seemed to intensify through the evening, and the more he tried to put his new boss out of his mind, the stronger the thoughts became, until Ben found himself in bed, masturbating to the thought of his boss standing over him, naked, smoking one of his big cigars, and Ben shot his load all over his chest. Feeling a bit better, he got ready for bed, but Mr. Evan’s invaded his dreams as well, and he woke up to sheets soaked with sweat and cum.

The next day of training, it was almost impossible to focus on the tasks at hand, with Mr. Evans so close to him, the smell of his smoke, the sensation of his boss’s body pushing against him as he leaned over to demonstrate something on the computer. Ben had dressed more professionally today, putting on an old tie and button down shirt, anything to try and impress, or even emulate, Mr. Evans, but his underwear was already soaked with cum, and he was so hard he could barely think.

“What’s wrong? You aren’t focusing today,” Mr. Evans said, “Stand up.”

Ben did, slowly, horrified to discover that the front of his pants were actually wet, the tent of his hard cock clearly visible. “I…I’m sorry sir, I…”

“Hush, I know how to take care of this. You need to be able to focus on work during work hours,” Mr. Evan’s said, smiling around his cigar. “Strip down.”

Was this a dream too? Ben found himself eagerly obeying his boss’s orders, stripping down, his hard cock jutting out. Mr. Evans gripped his cock drooled some spit onto Ben’s shaft, and in a very perfunctory fashion stroked him off. His motions were efficient and effective, almost business-like, but just feeling the massive man’s hand on his cock sent Ben’s mind into a spiral of horniness, and he came in a matter of minutes, shooting a huge load all over the wood floor of his boss’s study. His cock finally softening, he barely noticed as Mr. Evans picked the cage up from the desk, and secured it around Ben’s cock, locking it away. “There—now you’ll be able to concentrate better, won’t you?”

Ben sat back down in front of the screen, and again, time slipped away, and when he left, he apologized for his lack of focus. Ben drove home, and only then, did he realize he still had on the chastity cage. He didn’t mind it though, did he? No—if anything, he was embarrassed that he’d been so focused on his own pleasure, on his own desires. If anything, he should be the one taking care of his boss. Mr. Evans certainly had to be stressed out and in need of release. When he thought about how he’d just left, without so much as offering the fat older man reciprocation for helping him out earlier, he felt a deep sense of shame. 

The next day, it was the first thing he offered. “Sir, thank you for helping me out yesterday. The cage has been helping me a lot with my focus. Is…is there anything I can do to…help you out, before we get started today?”

Ben ended up on his knees under Mr. Evans’s desk, sucking on his boss’s cock while he answered a few morning emails. It was pure bliss. His cock was throbbing in its cage, but he didn’t mind it one bit—it was natural for him to be excited, serving this perfect man, but his pleasure was far less important. When he’d finished, and swallowed down the larger man’s load, Mr Evans looked down at him, leering. “You know, you’re showing a lot of aptitude for this position. Why don’t I offer you a job a little more suited to your capabilities? I’m in need of a personal assistant.”

“I…I’d love that sir,” Ben said, “I…assume we would be working together…closely?”

“You’d move in here next week. You’d be doing the job the company hired you for of course—I have a separate workstation for you in my home you can use. You would then also be responsible for assisting me around the house, and in whatever other capacities I might desire.”

Ben signed every contract that Mr. Evans set down in front of him, and then his boss bent him over the desk and fucked Ben’s hole while he smoked a cigar, to celebrate their new partnership. Within a week, Ben had sold all of his possessions, and moved into his new quarters in Mr. Evans’s home. He lived in the basement, and also had a small closet, barely enough room for a computer, which Mr. Evans would lock him inside during the workday, to ensure he stayed properly focused, allowing him out only for a few, state required rest periods, and to help relieve his stress on occasion. After work, Ben would strip off his suit, revealing the leather harness and collar he wore as Mr. Evans assistant, and begin his list of chores for the evening, all while smoking his own cigars. His boss was strict with his diet as well—loading him up with calories, assuring Ben that he preferred his assistants be reflections of him, both mentally and physically. Within a year, when he and his Master were out for evenings at the local leather bar, he could see it in the mirror—how he looked like a slightly shorter, younger clone of Mr. Evans, and that alone was enough to make his cock swell against the tight confines of his cage. It wasn’t quite the job he thought he’d signed up for, but it was a job he wouldn’t give up for anything in the world.