After graduating high school, I decided to take a gap year to save up for college. So, while all my friends went away to school, I stayed home doing odd jobs around town. One of my favorite jobs was housesitting. Rich people would literally pay me to live in their house, eat their food, and raid their extravagant liquor cabinets (although they didn't know about that last part). What's not to love?
This particular weekend, I'd really lucked out. Jim, an older guy -- mid 50s, biker type -- had hired me to keep an eye on his estate outside the city. It was a cool place, real hunting lodge vibes, but the highlight was definitely the bar. Wood everywhere, bearskin rug, moose heads mounted on the walls, and shelf after shelf of top-tier liquor. I looked up some of the labels as soon as he left, and that room alone would've paid my full tuition.
Excited to start my illicit tasting, I rushed through the list of daily chores (locking doors, watering plants, feeding the dog) before cracking open a $5,000 bottle of Pappy Van Winkle and settling into the plushest leather lounge chair I'd ever seen. I was a couple glasses in and had started flipping through the XXX channels on his 75" TV when a flash of light lit the room from the doorway. Startled, I spun toward the door, accidentally knocking my glass onto the hardwood floor and spilling easily a hundred dollars of bourbon across the hardwood.
"Is this what I'm paying you for? To steal my whiskey and jerk off in my office?" Jim demanded, half laughing as he stepped into the room with his phone held high, clearly recording. "N-no, it's not what it looks like," was all I could stammer back.
Jim slipped his phone back into his pocket as he stepped over to the table where I'd left the bottle of Pappy. He picked it up with a whistle, "I'll give you one thing, boy, you've got good taste."
"So do you!" I said with a weak smile, hoping we could just laugh the whole thing off. "That I do," he responded, slowly looking me up and down in an oddly sinister way...almost like he was staring straight through me. "Now, the way I see it, we've got two options," he continued. "Number one is I call your parents...and the police...and tell them you've stolen over a thousand dollars worth of liquor from me. If I recall correctly, you've just turned 19, so that's an expensive ticket just for possession. But it's also grand theft, which is a whole lot more than a ticket."
"Um...and option 2?" I asked, nervously.
"Well, I'm an old-fashioned guy and I believe in second chances. And clearly your parents didn't raise you right, so I'm willing to give you the discipline they never did. I'll spank you, say, 23 times. Once for each year this whiskey was aged."
He said it so matter of factly that it didn't even seem weird. "Just 23?" I thought to myself.
"Let's do option 2 then!" I said, cheerily, confident that this was the far better option.
"I'm going to spank you hard, though, you understand? I'll need to restrain you so you don't hurt either of us trying to move away," he cautioned.
"Um, I guess?" I responded, a little more warily.
"Okay then," he said, removing his belt, "Get out of my chair and kneel with your hands above your head." I did as I was told, easing onto the floor with my hands above my head as he stood over me, crotch inches from my face, tightly binding my forearms together with his belt. I wasn't quite expecting that -- he'd tied them in a way that kept me from lowering my arms, so my hands were totally immobile.
He took a step back, surveying his work before turning to one of the saddles hanging on the wall. He pulled off some component -- I wasn't sure what it was for exactly -- made of two leather strips connected to a metal ring. "I'm going to put this in your mouth so you don't bite your tongue," he explained, his gentle tone sharply contrasting with the rough way he pried my mouth open, making my eyes water from the strain on my jaw. He quickly pushed the ring in and tightly laced the leather behind my head.
"Do you know what a zamboni is?" He asked. Confused, I shook my head. "It's a college thing," he explained, gesturing pointedly at the Pappy I'd dropped on the floor, "When you spill your drink you have to slurp it up like a zamboni."
Put off by this bizarre request, I shook my head again, but he just shrugged as he settled into the leather chair I'd just vacated. "It's either that or I double your spanking," he said, "Boys need to clean up their messes."
Utterly humiliated, I leaned over (clumsily, due to the situation with my arms), and sucked up as much of the bourbon as I could. "Good boy," he said, "Only 23, then. Get up and come lay down across my lap."
I struggled to my feet, stumbling over to the chair. I hesitated, only for a moment, and he impatiently grabbed a fistful of my shirt, yanking me down across his legs. He held me down with one firm hand on back of my neck while he hooked the other into my waistband and my gym shorts down to my knees, revealing my bare ass, which he appreciatively squeezed. "I wish women my age had asses like this," he chuckled, pinching me hard. I squirmed and yelped a little, causing him to tighten his grip on my neck.
"Now, there are some rules I should've mentioned," he said, "You're going to count out loud. If you make any other sound, flinch, lose count, or in any other way fail to take what I'm giving you, then we start over. Understand?"
