The belt thrashed me viciously until there was nothing else left in the world except for my bare ass and that punishing strap of leather. It spanked me over and over again and the weight of my utter helplessness finally fell on me.
This wasn’t going to end until he decided it should.
Nothing I could say would stop this. He was going to punish me as hard as he saw fit. I bit my lip, struggling to accept such a complete lack of control. A particularly hard stroke dug into the tops of my thighs, and I gave up my vow to take this as stoically as possible.
A strangled cry escaped me. Another cruel smack caught just beneath my right bottom cheek, and I gasped, my eyes opening wide in shock.
This hurt so much.
He belted my legs and ass so hard that my eyes started to water. I blinked several times, trying to fight back tears when he finally threw the belt down beside me on the desk.
“The harder I belt you, the wetter this pussy gets. You’re enjoying this, aren’t you?” he said boldly, and I wailed openly in shame at his observation. He grasped my bottom cheeks with his hands and spread me open, displaying me completely to the men watching.
I whimpered, my face heating with embarrassment. Jon slid his fingertip along my thigh, almost as if he was making a point to me that all of them could see how soaking wet I was right now. With a quiet gasp, I tried to hide how much this entire ordeal was getting to me. Like he could read my thoughts, Jon slid a finger on top of my clit, making me moan before I had the forethought to slam my lips back together.
In silence, he walked around the desk and pulled out a drawer. I watched warily as he reached inside and took out a wooden box. He flipped it open right next to me and I cried out once I saw the contents.
There was a set of round steel butt plugs, each of them with a sparkling red jewel on the base. I gulped as he passed his fingers over the three toys. He started with the smallest one, picking it up and putting it back down with a shake of his head. He moved onto the middle-sized plug, wrapping his fingers around it and lifting it up to study it.
He put it back in the box. I panicked because there was only one more left.
I trembled when he picked up the largest one. I clenched my already sore bottom hole at the sight of it.
It was massive.
He took his time studying it and when his gaze finally leveled with mine, my mouth went completely dry.
“You can’t mean… please… not that… please, sir,” I pleaded.
He twirled the steel plug as if displaying it for me. I squirmed, unable to take my eyes off of it.
“Please, not that one,” I tried again.
He strode purposefully around the desk without putting the large plug back. Fearfully, I lay against the desk, hoping that my obedience would grant me some semblance of his mercy. I even tried to keep my legs wide for him hoping that might help me.
“I didn’t know. I didn’t…” I whimpered. The cold steel of the plug slid along my wet folds. He twirled it in my arousal, thoroughly coating the surface before he pushed it inside my soaked pussy. I gasped at the size of it as it stretched me open. It burned as my body tried to get used to its size. I whimpered as he pumped it in and out of me.
I hated that he was right, that I was so wet that it slid into me with embarrassing ease. Even worse, I actually started to like how it felt as he fucked me with it. I even found my body tightening around it as though I wanted to keep it in.
He pulled it out of my pussy quickly enough for a mortifying popping sound to echo throughout the room. I squeaked nervously as he gripped my bottom cheeks and spread me open, but I didn’t truly begin to panic until the pointed tip of the plug pressed against my asshole.
I tensed immediately.
My panic only grew greater. I pushed up away from the desk. I needed to get away.
He made sure I didn’t.
Exceedingly slowly, he began to press the large plug inside me. In less than a second, I realized that this was going to be much worse than his fingers. It was much thicker and impossibly wide. Tiny yelps escaped me as the burning pain radiated around my asshole, escalating with every moment that terrible thing was inside me. My back arched and my shoulders hunched forward, trying to do anything to lessen the stinging agony surging up and down my spine.
“Please!” I begged desperately.
The plug kept getting wider and wider and the tears that had almost fallen during the belting returned. This pain went so much deeper than the spanking had, and it was so much more shameful and terrible and it didn’t seem to have an end. It just kept going, the plug stretching me open more and more.
I didn’t know if it was mercy or cruelty, but when he roughly shoved the rest of it inside me, I screamed as the agony billowed outward.
One wave after another drowned me and I started to sob.
“I’m sorry,” I whispered hoarsely. My tears dripped down my cheeks and onto the surface of the desk. My entire body shook with one racking sob after the next. My muscles wouldn’t stop clenching around the plug and my punished asshole radiated with a soreness that refused to quell.