"Well, now," Mr. Sharpe smirked. "This is certainly a nice surprise. I was looking to recharge with a nice piece of ass after grading midterms and shit. Never dreamed I'd run into you of all people. Though then again, it's not entirely a surprise to find you working here. I did warn you about the importance of applying yourself, didn't I? Should have listened to me, Jimmy."
He did warn me; why the fuck didn't I listen! Jimmy asked himself. Jimmy never wanted to be working here, in the most notorious brothel in town. He figured he'd end up going to college on a sports scholarship, major in English or some shit, and just play shit by ear. He didn't count on blowing out his knee in his last semester of high school, which killed his chances of playing at college and any hope of a sports scholarship along with it. He'd never taken his studies seriously, so no other scholarships would be coming his way (everyone jokes about there being money for being left-handed, but it's only like fifty bucks, and in any event Jimmy was a righty anyway). And his parents had made clear that he was on his own the day he turned 18. His relationship with them was always strained. Forget about paying for college or cosigning his student loans, they wouldn't even keep letting him live with them once he was legally an adult.
So that left Jimmy with no college prospects, no money, no credit, and no place to stay. His only option was to try and find a job and somehow keep himself fed and housed while he figured out what to do with his life. But no one really wants to hire a high school graduate with lackluster grades, and the ones who did wouldn't pay enough for him to make rent.
No one except Bert, the proprietor of the Silk Strap, the only brothel in town that catered to clients (no matter how they identified) seeking to fuck guys. Bert liked what he saw from the moment Jimmy showed up, nervously asking if he had any need for someone to clean or serve drinks or something. With that face and that bubble butt, Bert thought, it'd be a waste to let this kid scrub toilets and mix cocktails. He told Jimmy as much, and told him that if he came to work as one of Bert's boys, he could easily make twice as much as any of the other shitty prospects that Jimmy had looked into, and to sweeten the deal, Bert offered to throw in room and board, too.
Jimmy didn't want to be a whore. He didn't. But Bert's offer was way too good to pass up, and he didn't have any better options. For once in his life he seized the opportunity presented to him. Which is how he now found himself naked in front of his old math teacher.
"So, like, should we just talk then?" Jimmy suggested. "This is all awkward enough, I don't want to make it any weirder than it already is."
"Fuck no, I don't want to 'just talk,'" Mr. Sharpe scoffed. "I want what I paid for: a night with the finest piece of ass ever to grace my classroom."
"But ... that's fucked up!" Jimmy protested. "You're my teacher! I'm your student!"
"Were my student," Mr. Sharpe corrected. "You were my student. But you're not anymore. Now, you're just a fucking boy-whore. And tonight, you're all mine, because I paid for you. So stop whining and do your fucking job, before I tell Bert and demand my money back."
Seeing no other choice, Jimmy resignedly began removing Mr. Sharpe's clothes. His eyes widened when the man's cock came into view. Based on how he filled out those khaki pants he tended to favor for work, Jimmy always suspected that Mr. Sharpe was well hung. But he just had no idea. His cock was at already least 8.5 inches long, heavily veined, and as thick as a cucumber. And still growing.
"Like what you see, slut?" Mr. Sharpe taunted. "Just wait till you feel what it's gonna do to that pussy. Now get on the bed on your knees, bitch, I want you from behind. No need for foreplay shit, I've been nearly rock hard since I walked through that door." Jimmy did as he was told, arching his back as he knew his clients liked, while Mr. Sharpe lubed up his dick and Jimmy's hole using the dispenser sitting on the dresser. He joined Jimmy on the bed and, with basically no preliminaries and without ever stopping, slowly inserted his massive member to the hilt in Jimmy's still tight pussy.
"OH FUUUUUUCK!" Jimmy cried as Mr. Sharpe began the fuck in earnest. Jimmy had pretty much succeeded in learning to enjoy (or at least not mind) taking cock since he began working at the Strap. Even though he had always thought of himself as straight, it was basically an occupational necessity. But this was different. Mr. Sharpe not only had the tool, he had technique, seeking out Jimmy's joy buzzer with laser focus and striking it every time he rammed his big dick home.
"Fuck yeah, boy," Mr. Sharpe cooed, "this pussy's even better than I dreamed it would be. And you'd better believe that I've been dreaming of it--of doing exactly this to it--ever since you arrived in my class. Every time you dragged your jock ass up to the whiteboard, every time you turned your back to me as you left for your next class, I thought of how good it would feel to plow this pussy. And now I can: anytime I want, for the right price. Pretty sure I'll be a regular client of yours from here on out, whore."
"Y'know," he mused, "I really should bring along Coach Watkins next time." Jimmy immediately tensed around Mr. Sharpe's cock and turned back to meet Mr. Sharpe's cruel smirk with a horrified look. "I'm sure your old coach would be eager to see you again and catch up about what you've been up to since."
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