Auditioning to Become His Boy

Auditioning to Become His Boy (3)

This is a work of fantasy and fiction. This work is copyrighted to me and can only be reprinted with my permission. Please remember to donate to Nifty to help keep this site running. If it is illegal in your area to read this or you are offended my M/m sex, then please leave this page. Otherwise, I hope you enjoy the story! I took a different turn this chapter, let me know if you like it or if you have other ideas. If you like the story, I have put my contact information at the bottom. Thanks again, Sirs!

With my eyes cast down, I saw a plug bigger than any I had taken yet drop to the floor. "Put it in, boy." My eyes got wide as I had never taken one with such a wide flare. As I grabbed it, my fingers couldn't touch as they wrapped around the widest flare and I estimated it to be about 5 inches long. I whimpered at the thought of the pain but knew not to speak out of turn. Luckily, Sir, in his generosity, held out his hand with a brown bottle of poppers and a bottle of lube. I eagerly took the two and squirted a covering onto the plug. Though it had a wide flare, the base was small, assuring it would not fall out for some time. I lined the tip of the toy with my hole and started pushing it in. I felt it start to stretch my hole, but my fingers felt at least another, much wider, inch left to go. I held the plug where it was with my left hand while my right hand awkwardly open the poppers and held them to my nose. The bottle didn't have a label, but after one hit in each nostril I knew it was not the cheap stuff. As the heat started to spread throughout my body, I leaned forward and forced the last inch in. I moaned as my hole wrapped around the small base and locked inside. I stayed with my face against the floor as I felt a warm stream spray on my back.

When I woke up the morning after my theater test, I saw the once loaded jock on my pillow, it must have fallen out through the night. My dick was hard but my sensitive ass hole, errr, pussy is what caught my attention when I moved my legs to kick off the covers. A small moan involuntarily slipped out and I reached down to feel my hole, still a little puffy and very sensitive. I stuck one finger in, noticing how easy it went, but heard a knock at my door before I could explore further. I swung my legs out of bed, but then felt how sore my muscles were still. I hobbled to the door and got to the kitchen before realizing I was still naked. The knocking at my door repeated, louder this time. "Be right there," I called out, working my way back to my bedroom. I frantically looked around for something to wear and grabbed an old pair of basketball shorts. I held them up with one hand while returning to the front door as fast as I could. When I opened the door, there was a very frustrated FedEx delivery guy holding a large brown box.

The man looked at my half naked body before pushing the box into my hand. His frustration turned into a smirk as he also handed me the electronic clipboard to sign. I spread my knees to try to keep the shorts up as I grabbed the pen with my free hand. As I signed my name and went to hand the clipboard back, the man stood there and continued to look at my falling shorts. I lost balance of the box in my hand, and as I shifted my body to catch it, I felt the cool air as my bottoms fell to my ankles. I quickly bent over, setting the box on the ground but felt his hand on my shoulder. "Don't worry, slut. I've already seen it, I was at the bookstore last night." I looked up at him, feeling my face flush red and unsure what to do. He was a pretty average looking guy, a small beer belly, thick thighs under his FedEx shorts, a broad chest with hair poking out the top, and a growing bulge in front of my face. Thankfully my front door was blocked from my neighbor's view as the FedEx man leaned his bearded face down next to mine and reached behind me to trace my pussy with his fingers. I moaned again as this stranger, who's cock I had apparently already had, played with me in the doorway of my own home. "You put on a good show last night. If you ever want to go further, I have a couple guys that get together every weekend and we haven't found our entertainment for tonight yet. Steve told me about your Master, let him know we want to rent you for the night. Have him call me." I watched as he pulled a pen from his pocket and wrote his name, Logan, followed by his phone number on the box he had just delivered. He picked up the clipboard from where I had lain it on the ground, smacked my ass, then turned and walked back to his truck.

I watched him walk away, before realizing what predicament I was in. I picked the box up, stepped out of my fallen shorts and shut the door. Before I could open it, I heard an email notification from my phone and realized I had left it on the counter, plugged in, all night. I grabbed it from where I was sitting and saw another email from Sir. "Just heard my package got delivered, boy. I overnighted a couple things you will need before our meeting. Take a look and let me know if you have any questions. - Sir"

I sent back an email telling Sir of what had just transpired with the FedEx man and gave him the contact information, then saying that I was about to open the box and will let him know shortly if I have any questions. I grabbed a knife and returned to the box on my kitchen table. After cutting open the tape and removing the packaging material, I started to lay out what was inside. After emptying the box, I took inventory. There were butt plugs of increasing size, two dildos- one 5 inches but very wide and one 9 inches long but slender, a shower enema kit, nipple clamps, a pair of knee pads, and a colon snake. I had seen colon snakes before but had never used one, and the thought of all 18 inches going in me was more intimidating than I wanted to admit. I took my phone and sent an email to Sir, saying that I didn't have any questions but did worry about taking 18 inches inside me. I also told Sir, that I didn't have any classes today, but was still sore from the prior night so I was going to take a hot bath with Epsom salt to relax my muscles. I set my phone back down and went to the bathroom, turned on some music, eased myself into a steamy bath, and drifted back to sleep.

When I awoke, the water was lukewarm and the salts had cleared. I started the drain and stood up to towel off. The ache on my pussy lips had subsided and my muscles felt new again. I wrapped the towel around my waist and headed to the kitchen to make something to fill my empty stomach. As I whipped up some lunch, I checked my phone to see another message from Sir. "The colon snake will go in you in time, boy, but not today. Today you get a bonus test. I contacted Logan and have arranged for you to be his entertainment for the night. I didn't know you were free all day, so I told him you would be there right at 6:00. Make sure you are clean, inside and out, and report to the address below. He has requested you wear the shorts you had on today and the tightest shirt you have. I also suggest wearing your new knee pads. We have discussed your limits and he has promised to honor them. You are not to refuse anything he or his friends desire tonight. Leave your phone in your car, you will be there late so don't make any plans for tomorrow morning, boy. He will also be recording the activities so I will see your performance. Rest up and check in when you leave. Be a good boy. -Sir"

I plugged the address into my phone and saw it was only a few blocks from me. Nervous again, my cock betrayed me and was tenting the towel around my waist. I haven't had an orgasm in days and desperately wanted one, but instead I ate the lunch I had prepared then returned to my bed to get some much needed rest. If tonight is anything like last night, I will need all that I can get. Though I was worried about what Logan had said about going "further" I trusted that he would respect the limits Sir told him and fell asleep, only to dream of what was to come.

I slept until the late afternoon. Once I awoke, I looked at the time and saw I had an hour to get ready. I went to the bathroom and used the new shower enema kit Sir had sent me to get extra clean. I made sure I was flushing clean, put on the shorts from earlier, and dug through my drawers until I found a shirt from my high school days. It pulled tight against my chest and stomach and I couldn't comfortable move my arms, but it was the tightest I had, as Logan had requested. I checked for another message from Sir, but had no new notifications, so I grabbed my phone and keys and started the short drive to Logan's. When I arrived, I saw it was a large, two story house and there were quite a few pickup trucks in the driveway. I parked on the street, left my phone and walked up to the scene of my next test for Sir. On the front door was a note: "Slut, go to the back." As I approached the back of the house, I could hear the raucous of several men. When I turned the corner, I saw a group of almost a dozen men sitting on a deck, each holding a beer. They all looked like the average blue-collar type. Hair poking out of every hole in their shirt, big bellies, several were balding. Behind them I could see a hot tub on the deck and as I looked around before they saw me, I saw a tall privacy fence surrounding a decent size yard.

I slowly approached them unnoticed until Logan announced my arrival, "Looks like the slut arrived, and ten minutes early, guess he can't wait to be our bitch." A loud cheer went up as they all turned to look at me, the young college boy, former football player, wearing a too-tight t-shirt and holding up my too baggy fabric shorts with one hand. All of these men were old enough to be my dad, or grandpa, except one, and they all were staring at me with lustful hunger. The youngest one looked about my age, but was more toned than I or anyone else, not having gained the beer gut the others had. Logan met me at the bottom of the stair to the deck, "So tonight slut, you are going to be the life of the party. But that doesn't start until the sun goes down. Until then you will be our server. Come inside and we will get you ready." I followed him inside through the crowd, getting fondled and groped as we went. Once in the door, I realized we were in the kitchen. Logan led me to the counter next to the fridge and grabbed a bottle of water from the fridge then a pill bottle from inside the closest cabinet. "This here is a Cialis. I don't want those shorts coming off before the sun goes down, but since you will have your hands full, I figured this will help keep them up. I took the pill handed to me and downed the whole bottle of water. Then Logan guided me to a bathroom. He handed me a butt plug, smaller than the one put in me last night. "This is a remote controlled vibrating plug. Each time a man finishes a beer, he gets the remote for as long as it takes for you to get his next beer. You will wait inside until you feel this then bring a beer out. I also know you aren't allowed to cum so if you do, your Master gave me permission to provide the punishment as long as none of us were touching your useless dick or balls. Once the sun goes down, the real party starts. Understood, slut?" I nodded my head while pulling my shorts down. "You have 2 minutes to get the plug in place, lube is in the cabinet, then I need the first beer."

I found the lube in the cabinet, applied it liberally, then squatted with my short still on and worked it in through my leg hole. Logan had said he didn't want my shorts to come off until sun down and didn't know if that meant now too. The plug was short and wide, but I managed to work it in right as I felt it start to vibrate. The vibrations made my dick rise and did the intended job of holding up my shorts under the waistband. I grabbed a bottle of beer out of the fridge and ran out to the deck looking for Logan. I saw him on the other side of the group of men grinning at me. I maneuvered my way through the crowd, my hole buzzing and throbbing, and presented the beer to him. He took the beer, set it on the deck railing, then pulled me over the railing as well. He slapped my ass hard twice, once on each cheek. I yelped with each slap as I only had a worn layer of fabric between his hand and my skin. The plug continued to vibrate as he held in firm in the hand that was holding my back down against the wooden beam. "That's for the two mistakes you made boy. Number one is the beer should be open before you come out of the door. The second is that you should be on all fours. You have knee pads on for a reason." He let me up and I dropped to my knees, then all fours. Finally the vibrating stopped. I looked down and saw a wet spot was forming on the shorts where my pent up dick hanged down. I looked around and saw a camera, as Sir had said there would be, in the corner of the deck, catching everything I was doing.

I crawled back inside, this time having to crawl over stretched legs and around standing guests. I was only inside a minute before the vibration started again. This time, I open the beer bottle and, not knowing what else to do, held the open end in my mouth as I crawled back through the door, looking for the controller of the remote. I was lucky that it was the man closest to the door. As he took the beer and put it to his lips, the vibration stopped again. This continued for half an hour, sometimes the man would be on the other side of the group, sometimes by the door. One thought it would be funny to go to the other end of the yard, but that only irritated his friends as it took me longer to get there and back for the next thirsty patron. Each time, I also had to take the empty bottle back inside and dispose of it in the trash can on the other side of the kitchen. After half an hour, the guests had a new idea that I had not expected, though all of this was a first for me.

I was inside, resting for a few minutes without a vibration when my hole started to buzz again. I grabbed another beer from the seemingly endless stock and repeated the process I had perfected, carrying the bottle out with my mouth to hand it over in exchange for the empty bottle and the vibrations to stop. The wet spot on my crotch had spread to both thighs as my dick continued to leak, making them heavy and sagging. This time, though, when I handed over the beer, the bottle put in my mouth was not empty. It took only a moment of confusion before it splashed on my tongue and I realized the owner had emptied his bladder into it. He held it still, knowing I would react. "Why get up to go to the bathroom when we have a servant slut to take our piss away?" Logan's voice spoke over the laughing from his guests. "Do what you want with it, boy, but it doesn't go in the trash and you aren't getting any more water or beer tonight." I had never done piss play but had told Sir I wanted to try it, I guess this is his way of letting me experiment. However, the acidic taste assaulted my tongue and I barely made it back to the kitchen before dumping the bottle down the sink and throwing the bottle in the trash.

After fifteen more minutes, my thirst was increasing while the piss splashing on my tongue from every bottle I returned was dulling my taste buds to its acridness. When the next buzz in my pussy signaled for a new drink, this time it was for the host of the party. When Logan handed me his recycled bottle, he scratched my head and told me how great of a job I was doing. "I would never guess you were a first timer to all this, boy. Your Master is a lucky man. I'm sure he would be proud of how well you are doing so far." He smiled while crouching down and looking in my eyes. Being reminded I was doing this for Sir, I looked over to the camera and tilted the bottle up as best I could, swallowing Logan's watery beer piss as fast as I could. I could only get about half the bottle down, it was difficult to breathe in between gulps while on all fours and my head back, but it was enough for Logan to smile and pat my head. "The sun will be down in about fifteen more minutes, piss slut. Keep it up and we will let you get in the hot tub." The thought of getting in the hot tub and relaxing my very sore arms and thighs was enough to keep me going until sundown.

There were ten more beers to get in that time, and I looked at the camera and drank all of the recycled beer I was handed in return for that time. By the time the deck lights came on, some tiki torches along the railing really, I had learned to love the taste of beer piss while filling my bladder in the process. My dick was leaking more than ever, however, after a full hour of almost constant vibrations against my prostate and the work of the little blue pill I had been given. When I returned the last time with a beer in my mouth, it was again for Logan. "Good boy, we are about to start the party, but first, I am sure you have to take a piss yourself." I nodded to the affirmative and bounced between both knees, trying to relieve the pressure building. "Lay on your back boy, legs spread." I rolled over, grateful to be off my knees and hands. I spread my knees while keeping my legs bent, my loose shorts clinging to me with my own juices. Logan knelt down next to me and started to rub my stomach. Go ahead, boy. Piss and show us how much you love it.

I started to let loose my bladder, completely soaking my shorts as it pooled out around me and dripped through the crack of the deck. I sighed at the sudden relief, closing my eyes to enjoy the warmth spreading over my lower half. As I finished, I felt warmth on my top half as well. I open my eyes and saw Logan straddling me while pissing his own shorts. The excess dripped down onto my tight shirt and soaked into the cloth and my skin. I moaned as the warm piss started to steam a little when it met the cooling night air. In the light from the torches, I could see other guests coming closer while the rest began to strip out of their clothes. One guest, an older man in his 50's with a belly that hung over his crotch, straddled my chest in mesh shorts and aimed his covered cock at my mouth. I felt the warmth start on my chest before he leaned forward onto his hands and hung his streaming shorts over my mouth. I leaned up and opened wide, taking as much of the stream as I could into my mouth while swallowing as fast as I could. My forehead pressed against the hanging stomach as my mouth filled three times with his grandpa piss. Once his bladder was empty, he stood up and stripped out of his clothes while standing over me.

His was the first cock I saw that night as he dropped his shorts. It was short and buried in a mound of flesh and hair. Once free of his clothes, he straddled me again, this time with his cock and balls over my mouth. I dutifully sucked them in and cleaned them of the piss that had soaked into his skin. As I felt him harden in my mouth, he pulled out and was replaced by the guest my age. The young man straddled my head facing my feet and put his semi hard cock in my mouth to clean. As I cleaned the head and shaft, he replaced it with his balls. They were hairless like the rest of him, but I could not detect any stubble, apparently he was naturally smooth. His balls hung like a bull though and I could not fit both in my mouth at the same time despite my attempts. Thinking he would pull off like the rest of them, I was surprised when he moved farther forward and settled his ass hole on my mouth. Using what I learned with Roger, the grandpa, last night I stuck my tongue in deep and licked all around the smooth hole.

A deep voice resonated, "That's right, clean my hole fucking faggot. Taste all that piss that dripped down there." The young man held still then and started sighing as I tasted a fresh stream of piss coming down his crack. I looked up and saw another older guest pissing on him. He kept his stream slow and steady so that it flowed down the younger man's back and into his crack, ending up on my tongue. The fresh piss mixed with the young ass hole sent my lust into overdrive as I buried my tongue back in the ass once the stream stopped. I felt a tug on my shorts and lifted my hips so whoever it was could expose my bottom half. As the piss drenched shorts were pulled off my feet, I once again felt the plug vibrate, stronger than before. It pulsed and buzzed so loud I could hear the vibration on the wood underneath me. I humped into the air, moving my hips so the plug would braze against my prostate.

The young guest on my face stood up as the plug was pulled out of my pussy without warning. I gasped then groaned as I felt empty and void. I looked to see Logan removing my knee pads before reaching out his hand. I reached out and let him pull me up, then clung to his naked body as I got used to being upright again. When my head cleared, I looked over to see all the young guest joining the others in the bubbling hot tub. "I told you if you did good you could get in the hot tub, so time for your reward." He led me over to the steps of the hot tub and let me get in while he climbed in after me. He sat in front of the steps while I stood in the middle, mere inches away from all the other naked men while I still had my shirt on. I reached to pull it off but Logan grabbed my wrists. "Leave it on, it gives us something to grab onto." I put my hands down and looked around, noticing there were no empty seats left. The oldest man smiled at me and pulled my shirt to him so I was facing him. He kept pulling me closer, forcing me to put my knees on the seat on either side of him. "Have a seat," he said as he pushed my thighs down. My thighs lowered into the bubbling water as I felt his cock at my boy pussy. The frothy water made it so I couldn't see below the waist of anyone in the hot tub, but his cock seemed to know where it was going as it sunk into my previously plugged pussy. I moaned as my ass rested on his spread thighs.

He thrust into me only a minute before I felt his cock spasm in my hole and he let out a loud groan. He raised my waist up to let his cock flop out. I went to move off him, but he held me in place as I felt another cock take the place his had just been. This one was longer and I felt his head stretching deep into me, past where the plug had been. I leaned forward and placed my hands on the side of the tub, when I did, the first man to fuck me started biting and sucking on my nipples through my piss soaked shirt. I rested my head on my arm as I continued to get pound from behind like a dog. It was only a few minutes before this man, too, bred my bitch hole. After this I was passed around to each guest. Some had me ride them, some bent me over the side of the hot tub, and one had me lay on my back with just my head above water so he could lick my face while he fucked me. My pussy was filled with cum, the excess adding to the frothy water. I kept my hole clamped as much as I could, though, hoping to keep a good share. There were only three men that hadn't fucked me: Logan, the youngest guest, and the old man that fed me his piss.

Logan gestured that the young guest was next, so I waded through the water to him and he leaned back, signaling for me to ride him. He smirked up at me, "Now to see how far that pussy stretches." I still couldn't see under the water, but when I straddled him I felt his cock head poking at my hole. It didn't slip in like the rest, though, his cock had grown to the girth of one of the beer bottles I had served him. Logan reached over the side of the tub and pulled up a brown bottle I was beginning to recognize all too well. He opened it and held it under my nostrils, having me take two deep hits in each nostril, holding them in for a few seconds before breathing out. When he pulled it away, my body felt like it was overheating from the combination of the hot tub and the poppers, as well as the intense lust within me. The young man grabbed my shoulders, adjusted his hips, then pulled me down full force on the thick, hairless cock. My cock started erupting right above the water line, squirting onto the young chest and face in front of me. I started riding the cock inside me, milking out a spurt with every bounce until my body collapsed from the orgasm. Logan started chuckling as the young buck inside me thrust up into me faster. My spasming hole milked his cock as he deposited a ninth load inside my already overflowing pussy. The old man leaned over between our bodies and started lapping up my college cum. While he was bent over, out of the corner of my eye, I saw the other men line up behind him. One by one, they pushed their soft cock head inside his ass, left it there a minute, then pulled out, only to be replaced by the next one.

"Since he broke the rules can I break them?" The old man asked. With a nod from Logan, he took my dick in his mouth and suck the dribbling cum out of it. While he did, I felt another warmth filling my bowels as the young man sighed in relief. I looked to Logan who was only wearing a grin as he made a hand gesture to the other guests. They picked me up and carried me to one of the lounge chairs and laid me on my back while pulling my legs above my head. The old man straddled my head and lowered his body. "I'm so happy he broke," he said as his ass met my mouth.

"Since you broke the rules, slut, your punishment is two-fold. First, you were going to get your choice of who to feed you your final piss loads, instead Gary here gets the honors. Second, you get your balls beat until he is clean as a whistle. Gary, the old man, grabbed my hands and held them to his chest while the other men held my knees far apart. As the first paddle hit my balls, I screamed and a flood of piss from Gary's hole entered my mouth before closing off. "Hold on, guys, let's up the ante." I couldn't see around Gary's body, but felt something enter my hole and then the vibrations from earlier returned at their strongest setting. "Let me know when you're empty, Gary," Logan said as I felt another swat at my balls. Gary let only a trickle out as my balls continued to be battered. I tried to suck it out in between screams but that would only get him to clench completely closed. Finally after nothing more came out, Gary stood still for another three paddles, totaling twenty, before standing up.

I looked down at my swollen balls before Logan flipped my body over, pulled out the plug, and rammed his cock into my piss filled pussy. He lasted longer than the others, and while I felt piss dripping down my thighs, a couple guests started emptying their bladders onto my back and hair again. When I was soaked once more, Logan announced he was breeding the bitch and sank full hilt into me. He kept it there a few minutes, emptying his bladder once more to replace what he had fucked out of me. After that, he stood up and threw my shorts at me. "Get home, bitch. I'll send a copy of the tape to your Master, as well as each of the guests tonight." They all gathered their clothes and walked inside, leaving me alone on the deck with the tiki torches burning down. "Oh before you go, don't forget this," Logan popped his head back out of the door. He threw a wad of bills at me and it landed on the floor at my feet. "$10 per guest was your Master's charge. There's an extra 10 in there from Gary for losing. Make sure your Master gets it." In shock, I grabbed my dried shorts and pulled them over my hips. I reeked of sex and piss and knew I would smell it in my car for days to come. And now I was a $10 whore on top of it.

Once I got home, I stripped down, made a pot of coffee and sent an email to Sir. It was a long, detailed account of the night's events. I knew he would see the tape, but I wanted to admit my transgression before somebody else told him. I apologized profusely, admitted I was a worthless slut that disobeyed orders and would understand if he was done with me. As I drank the coffee, I felt the piss leak out of my pussy onto the chair and floor. Before going to bed, I licked it all up, this time able to savor the flavor of the piss more, then went to bed. I put the money in an envelope and left it on top of the fridge. I didn't know if Sir would respond after what I had just done, but all I could do was get some rest and hope for the best. Before I drifted off to sleep, I got a text from Logan. He must have gotten it from Sir. "Good times tonight, boy. We could use you on a weekly basis. I'll check with your Master and let you know."

I am honestly not sure what will be coming next. I have some ideas but not sure what you guys want to see. I love to hear from my readers for anything. If you are a fellow sub and want to share your stories, a Dom that wants to tell me what to do, or just a fan that has some ideas, feel free to contact me. Thank you for taking the time, Sirs! son4dad1987@yahoo.com