The Icy Hot had worn off long ago. Sir fucked me into the morning. My body felt rung out. The caning last night left my hole more sensitive than normal. It just kept cumming and felt swollen and wide open at the same time. My abs were sore from the anal contractions.
I usually cry when I go into headspace, which turns my sadistic Sir on even more. With the night's fucking, the caning, and the assgasms, I was a blubbering mess, which made Him fuck me harder. He relentlessly pistoned my abused hole so hard my vision jumped with each thrust. He'd cum in me 3 times and pissed in me twice. My hole was so sensitive that the cum squirts had felt like Him pissing in me and the piss felt like a fire hose of the hottest, most enjoyable lava let loose inside me.
When I finally gave my safe word, He returned that evil, beautiful, vicious smile I loved and pulled out. That made my hole cum again and He watched me curiously as my body was racked with a final wave of sensation. I fell asleep to the feel of the delicious warmth and heat in my hole, the smell of his shea butter lotion, and the morning sun beaming into my eye.
That Monday, as I readied for the gym, my bag felt a little heavy. I discovered Sir's favorite (and largest) plug and my chastity cage. I sighed. My hole was still sensitive from the weekend, and it took longer than usual to clean out and insert the plug, which made my dick hard, so it took even longer to get the cage on. Worst of all, this plug could be controlled remotely. What fresh hell had I gotten myself into?
It wasn't until I changed into my gym clothes in the locker room that I saw the evil genius of Sir's request. The tight gym shorts I normally wore already left nothing to the imagination and the cage stood out clearly in them. Also, the shorts helped to hold the plug in. I felt every eye on me as I headed to the floor and my cheeks warmed. The metal ribs of the chastity cage poked out in the front, making it look like I had a hard-on to the untrained eye. I caught the amused smile on more than one face as they understood what was really going on. To make matters worse, it was leg day and every movement forced that plug against my prostate. I was leaking uncontrollably. When I got up from one machine, there was a pool of pre-cum. Some gym bunnies nearby laughed out loud and I flushed as I cleaned it up.
I was squatted in the middle of my battle ropes routine when the first jolt from the plug came. My hole was already screaming from squatting, and part of me wanted to quit, but I was afraid if I didn't go through with my normal routine, Sir would find out somehow. A paranoid corner of my mind knew He was somewhere close, watching me. The vibrations increased in intensity and duration and eventually I had an assgasm. I just knew everyone could hear the plug vibrating away inside me. I gritted my teeth to keep from crying out as the sensations coursed through me, made more intense by the plug invading my guts. My hole tried to force the plug out with each contraction, but the gym shorts kept it in, making my contractions even harder. I rushed to the locker room bathroom and as I sat, I heard my phone. It was Sir.
"Everything ok?" He asked with infuriating innocence. Even as He spoke, I could feel the intensity of the plug ratchet up a couple of notches. My legs were shaking, and my stomach cramped up from the waves of anal contraction. I begged Him to stop. I was practically crying, a big mistake because wherever He was, He was likely stroking himself over my distress. Without thinking I removed the plug, and a loud buzzing filled the bathroom. I knew Sir could hear it and immediately, I knew I had fucked up. The buzzing ceased and there was an interminable silence as I looked at the phone, waiting for Sir's next words.
"I will see you this evening." His tone was flat, emotionless. I had fucked up bad. It was my hole, but it was His property. He had given me the plug to wear and only He could take it out or tell me to do so. I thought back to the last time I had done so without permission. He has paddled me 1000 times. Afterwards, you could see the bruises through my brown skin for a week. Even as I winced from the pain of that moment, my dick strained against its cage at the thought.
For days, I tried to make it up to Him, waking Him up every morning with a blow job and offering my mouth and hole as a urinal. He happily used my mouth but wouldn't touch my hole. I was frustrated and horny, and my hole ached to be filled with Him. When I tried to sit on His dick, He recoiled with mock horror, "I would never do that to YOUR hole," He said, clutching at fake pearls. I knew I was in for it at some point. I shuddered at the thought.
On Day 5 with no dick (Saturday) W/we headed to the bar. I wore the kilt Sir liked because it was easy for Him to casually play with my hole as W/we stood at the bar drinking beer and making small talk. I had even pre-lubed for the occasion. For the first 2 hours, He ignored my hole, so at some point, I had turned to say hello to a friend. When I turned back, I saw Sir disappearing into the Dark Room on the other side of the bar. I felt my phone buzz with a text from Sir.
"Take off all your clothes and join me in the Dark Room. You have 10 seconds." My heart leaped as I stripped out of all my gear, to the surprise of several patrons. As I rushed to the Dark Room, I heard several people following me.
I felt the heat of bodies in the Dark Room but saw nothing. The air smelled of sex and my dick strained against the cage (after Monday, I assumed nothing and had left it on). I called out for Sir but heard no reply. I moved deeper into the space, feeling hands on my body. Everywhere was the sound of slurping and the delicious wet slap of flesh on flesh. Suddenly, His voice was next to my ear.
"Whose hole is this?"
Before I could respond, He grabbed me in a choke hold and drove all 10 inches of His rock-hard dick into my hole. Stars overlaid the darkness and there was an infinitesimal moment of pain immediately suffused with pleasure. I felt His wiry pubes crush against my ass as He rammed in and out of me, the frustration of not being inside of me evident in the power of His assault. He threaded His arms underneath my armpits and interlaced His fingers against the back of my neck. With each thrust, He repeated His question until it became a mantra.
Whose hole is this? Whose hole is this? Whose hole is this?
I had gone from responding with moans to guttural grunts and at some point, shouts that were practically screams. My insides were a complete mush as W/we rutted like animals. I felt Him cum and from deep in me I screamed, "IT'S YOUR PUSSY, SIR!!!"
I felt a sudden coolness as His dick evacuated my bowels, only to be replaced by something larger: His fist. With little effort, He got His whole hand inside of me and was piston fucking me with His fist. I was screaming, "IT'S YOUR PUSSY" at the top of my lungs. I felt something wet on my legs and feet and realized that I had pissed myself in my excitement. I collapsed into the puddle of my piss and in the sudden silence, I heard the unmistakable sound of men jerking themselves off to orgasm. Everyone has stopped sucking and fucking to listen to Sir claim His property.
I clutched Sir's leg in contentment as I caught my breath but a part of me was leery. There was no way Sir had forgotten about The Game. Although W/we had fun, this hadn't been at all humiliating. I searched His face for clues as W/we got dressed, then said O/our goodbyes, but all He did was give me that evil, beautiful, vicious smile I loved.