Disclaimer: All rights reserved. No part of the story can be reproduced in any form without the permission of the author.
Several Masters and Sirs on the web have asked for this story, so i thought i'd post it here. Respectfully to the Masters involved, i have embellished some. The names, dates, and places are changed to protect all involved. This is loosely based on a true story. Your constructive feedback has been great so far, more is very welcome at obedientboy4SIR@gmail.com. Please, enjoy.
Chapter four - pleasure and pain
After an hour or so, Master had enough basking in the sun and me squirming under His casual manipulation, i was hornier than ever. Every time i flipped onto my back, i learned to instinctively spread my legs for my Master. my boi dick throbbed and dripped constantly and my balls were red and swollen. But still, when i was rolled over, i obediently offered them to Master for His pleasure. Pain was not a consideration, pleasing my Master was my only goal. When Master, was finally ready to get up, He stood and stretched. Kicking me softly with His foot, He ordered me to go to the room and get Him a cold beer and water for myself.
i got up and hurried to the room, my hard boi dick pointing the way. The plug had somewhat settled in my ass and i had almost forgotten about it, focused much more on the easy ache in my balls and the throb in my dick. About my second step into my journey, my ass clenched hard on the plug.
"Very nice, boi" Master commented "that's how it works." i blushed, knowing that the other resort patrons lounging by the pool probably saw my glutes flex hard and i couldn't help but clench and unclench my ass as i gingerly walked to the room. i'm sure it was quite a show. In the room, i went into the bathroom and removed the plug and made sure i was appropriately 24/7 clean for Master. This was becoming a ritual, 24-hours into the trip. Anytime i had a free minute alone, i ran to the bathroom to make sure. The plug was not easy to pull out, but eventually i worked it free, went about my business, cleaned up thoroughly and replugged myself. i grabbed the beer and a bottle of water and went back to Master.
"Adjust my chair up, boi" He ordered as i handed Him His opened can of cold beer. Master Blake was also sitting upright next to him, drinking water, with a naked Simon straddling His leg and massaging His foot. Jared was in the pool playing a naked volleyball game with some other guests. Master allowed me join them, if i wished. The water looked inviting, so i thanked Master and jumped in. i swam up to Jared and joined the game. The water felt amazing on my skin, especially my sore balls and tender ass. Jared hugged me and introduced me to the other guys as Master Richard's boi, pointing to my Master and holdng up the lock on my collar. A chorus of 'welcome boi' greeted me. Several Men shouted compliments to my Master, He waved and smiled back.
"Come be on our team," called one of the bigger Men on the other side of the net "they've got more than enough boi talent over there." As i swam over to the other side, i recognized the Man as the one from the breakfast bar in the morning. i glanced at Master and He nodded to me.
"Good boi, fuckin' cockwhore," the Man said as He rubbed my head and casually grabbed my ass. He pushed me to the space in front of Him. His fingers toyed with the plug or my balls every chance He got for the rest of the game. His huge cock throbbed under the water, tantalizing me.
Volleyball in the pool is fun. When the ball was inadvertently knocked out of the pool, and it often did, one of the bois in the pool was always sent after it. That meant basically hoisting your sleek boi body up the pool edge and out of the water. It inevitably left your naked boi ass exposed to everyone watching. It was often smacked hard by which ever Man or Master was nearest you. Both Jared and i and two other bois got more than a few hard smacks. It was a lot of fun and there was a lot of groping and friendly playfulness under the water.
After a while, the game ended and Jared and i lounged in the pool together. Simon was now working my Master's feet like he had Master Blake's. i told Jared what a good boi i thought Simon was, he proceeded to tell me that Simon got a "thorough thrashing" last night and he was extra subservient today. i started to ask and he put his finger to my lips.
"It's not polite to ask about it, john" he informed me, "just know the situation, good?" i thanked him for the advice. we lounged a bit more and then got out of the pool. Master ordered another beer and one for Master Blake as well. i ran to get them. As i was entering the room, Master barked out to bring four. i glanced back to see Master Lonny and Master Todd with them. i came back with four cold beers and opened them each as i served them. Master first, of course. Master Todd was seated on the end of the lounge and He had a huge basket in a tight pair of black board shorts. How did i miss that earlier? He was a well muscled, biker kind of guy. Tattoos all over His arms and chest, minimal body hair, pure Man. Master Lonny reached for me, but Master Todd grabbed me first.
"Jesus, don't fight over him, guys" Master said, feigning exasperation. Master Todd just manhandled me into straddling His leg and then sitting on His knee, shoving the plug in hard. Holding my arms together behind my back He bounced me gently on His knee. The jiggling plug and the manhandling brought me to a full blown erection instantly.
"Randy little bastard, ain't he?" Master Blake commented. My Master smiled proudly, reached over and stroked my hard boi dick a couple of times, and then told them about our shopping spree including every last detail. By the end of the story, every exposed cock in the group was rock hard. Master Lonny grabbed His car keys and said He was off to get an early start. The group started to disperse. Master got up and was chatting idly with Master Todd. Together, They started for the room.
"Grab our shit and get in the room, NOW, boi" He barked. i hastily picked up the towels, sunscreen and beer cans; smiled good bye to the lads as Simon gently stroked Master Blake's hard cock. he looked like he was in a trance.
Once in the room Master Todd was naked and on the bed. Master shut the door, grabbed my arm and pushed me onto the bed. "Go get it, cockwhore" He ordered. i crawled up the bed and put my lips around Master Todd's big uncut nine inch cock. Master Todd tapped my right arm, then my left. i kept sucking His big cock. Then He realized i had no idea what the taps meant. He explained that when a Master taps a boi like that while the boi is sucking cock, it means that the boi should work the Master's nips with his hands. Something new. Obediently, i reached up and started tweaking Master Todd's nipples and His cock got rigid. He had one hand on my head and the other tweaking my nips as best He could reach them. i was tingling all over, this was so hot.
i heard a chain jingle, then noticed Master next to me. Master had a devious grin on His face. He rubbed my head and stroked my neck, then He reached under me and clamped one then the other of my nips. It hurt like crazy, but as i moaned Master Todd pushed and His massive cock slid past my gag reflex and into my throat.
"Ohhh... fuckin' good boi... nice," He hissed as i struggled with the snake down my gullet. Just as i thought i'd pass out, He eased His hold on my head and let His cock move enough for me to breathe through my nose, but never all the way out of my mouth. After half a breath, He shoved me back down, it was agony in my throat until Master pulled on the chain between my tits. Now my whole body started to shake and sweat was pouring off me. i was a mess between pain and pleasure. My very limited deep throating skills were clearly being put to the test. i sputtered a lot, gagged occasionally and felt a constant stream of tears and snot run down my face.
In the haze, i felt Master harshly yank out the plug and immediately shove home His fat cock. i was effectively skewered, spit roasted between two very hot tops. With little pretense, the Masters went at it. Their fuck toy was skull fucked on one end and hard fucked on the other. Besides hearing myself grunt and groan, all i could hear was the chain around my neck and the chain between my tits jingling. Every once in a while Master Todd leaned forward and kissed my Master over top of me. It was fucking hot as hell.
Eventually Master Todd lunged forward and impaled my throat with His amazing cock. i felt it pulse a couple of times and then He pulled back and flooded my mouth. i coughed and blew cum out of my nose and mouth. For which i immediately got a very hard slap in the face. Master dumped His load watching Master Todd slap me around as Master encouraged him to discipline me. i was a blithering mess, tears and cum and throat slime everywhere. The slaps were harsh and stung like hell.
Master pulled out and dragged me to the bathroom and threw me into the shower. They both stood there for a brief second and then piss all over me. Master looked unhappy. There would be punishment. i started to grovel and beg forgiveness. i got another hard slap. He walked out and told me clean myself up. i was fucked out and scared shitless. i feebly stood up and turned on the shower. i washed off the piss as quickly i could and then made sure everywhere else was clean. i dried off with one of the used beach towels and went out into the main room.
Master was sitting in the armchair, Master Todd had left. He pointed to the spot before Him and ordered me to present. i knew that meant to kneel obediently before him, knees as wide apart as possible, ankles together, hands behind my back, head bowed. In this position a slave's dick and balls are completely exposed and presented to his Master. Master leaned forward and reattached the nipple clamps. They'd come off at some point in all that fucking and roughness. My tits were on fire as soon as they were back on. i winced, groaned and shook nervously.
Next Master put the high leather training collar on me. My throat was sore from the skull fucking and now swallowing was even tighter. He stood up and had me kneel on the armchair with my ass out to him. Next the plug went back in. My ass lips were especially tender now, but Master just spit on my hole and shoved the metal invader in. i screamed as it stretched me open. Master cruelly held it there at the widest point. Moving it back and forth a millimeter or so. Laughing as i struggled, then finally allowing my ass to swallow it up.
Next Master grabbed His big black belt. "Ten, boi. Steady yourself and count 'em out like Master Blake taught you yesterday. Remember?" He asked.
"Yes Master, thank you Master" i replied nervously, my body shook with anticipation. Try as i might, i could not will myself to stillness.
As He administered ten cracks with the belt across my sore ass, back and thighs, He explained in a very calm, stern voice that He was disappointed. In the future, i was to do everything imaginable to not choke and spit up cum ever again. A Master's seed is a precious gift for every slave to savor. Whether it comes from His Master's cock or the cock of any Man the Master presents to the slave. Each sting of the belt was met with a count and a thank you and a request for the next. At ten, Master hesitated and then applied two additional strokes. He explained that a Master can add or subtract strokes as He wishes and a slave should always be grateful. My back, ass and legs were on fire at the end of it and i was shaking like a leaf, but incredibly grateful for the lesson.
Master eased me back into a standing position, removed the training collar and nipple clamps. He massaged my sore nipples and i screamed. He silenced me with His mouth and He kissed me tenderly. He led me into the shower and allowed me to wash His beautiful body. i scrubbed Him head to toe, everywhere. He rubbed the wet washcloth tenderly over me as well. We made out in that shower for a solid ten minutes. Sore and beaten as i was, it was incredibly erotic. When it finally ended, He had me dry Him off and then allowed me to dry myself off with the same wet towel, of course.
Dinner was just the two of us at a little place down the road. i was granted permission to speak freely over a very light meal (just salad for the boi) and He basically checked to make sure everything was going as well as He was interpreting it to go. As a novice, i was so grateful to have found a kind and caring Master to start this journey with. i thanked him profusely.
Back at the resort, we dressed for the welcome event and the first night out.