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?"
Really starting to get a bit scared now, I nodded. I'd barely moved my head before I felt the first stinging blow hard on my right cheek. I instantly recoiled in pain, completely forgetting what he'd just said. "Doesn't count, boy, that's a flinch," he growled, before smacking me again. I managed to stay still and silent, but completely forgot to count.
"Don't forget to count, boy!" he ordered, striking my right cheek for a third time
"One!" I squeaked out through the metal ring in my mouth, almost breathless from the pain.
"Mmm, there's a good boy," he said, squeezing my ass right between the cheeks. I felt his fingertips linger on my hole for a second before the hand lifted off and came down again.
"Oo," was all I could manage through the gag, but the pain wasn't quite as intense this time. I'd made it up to twelve when I felt something pushing against my stomach. It only took a moment for me to realize he was getting off on this! The sick fuck. Disgusted, I tried to squirm away, but he shifted his hand from my neck to my hair, grabbing my ass so hard with the other hand that a finger actually slipped inside as he yanked me back onto his lap.
"Back to zero," he snarled, "But I've decided to alter our deal, because you've turned out to be more of a bitch than I thought. I don't want to risk leaving any evidence on you, so we're going to try something new." With that, he pushed me off his lap and onto the floor, making sure to keep a tight grip on my hair as he shoved my face against the bulge in his pants.
Looking down at me with a sick smile, he continued, "The new deal is, you're going to stay here for the whole weekend and I'll pay you your $50, and you'll also get to be my personal cum dumpster. How does that sound?" Terrified, I vigorously shook my head and tried to object but only gibberish made it through the gag. "I didn't quite catch that, but since my cock is already practically in your mouth I'll just take it as a yes," he said.
Holding me tight against his thigh with one hand, he slowly unzipped his jeans with the other, pushing them aside to reveal his rock hard cock throbbing against a tight pair of boxer briefs. Clearly enjoying my discomfort, he slowly pulled them down until his cock sprang free, narrowly missing my face.
"Have you ever been this close to a cock before?" he asked, not waiting for an answer before pressing my mouth against his hairy balls. I tried helplessly to pull away as he ground against my face, pubes brushing across my lips and into my mouth. "Look at me," he ordered, and I felt my eyes turn toward him almost against my will. He slapped his cock up against my face, licking his lips, "Those helpless little bitch eyes look so good next to my cock. I want you to keep your eyes on me, even when I'm fucking your throat, do you understand? Or else it will be a whole lot worse."
