Guess What?

Author's Note: Trigger Warning: This story contains themes of group sex, bondage, and a little bit of non-consent.

The door to my room swung open quickly. I rolled over to see who was there. My Dom's silhouette filled the door frame. He was older than me by 12 years (I had just turned 35) but kept himself in good shape. Very handsome with a strong jawline.

"How is my muscle sub this morning?"

He asked, pulling back the covers, admiring my nude, muscular frame (6'3, 265 with a 50" chest and 38" waist).

"I am good, Sir." I replied, sitting up on my elbows. My morning wood stood proud and Sir rubbed it gently.

"Mmm, thank you Sir." I moaned.

"We are going to play a game today. I think you will enjoy it, but I know my friends and I will." Sir stated.

Whenever he mentioned friends I knew I was in for a long day of pleasure and torture.

"I want you showered, fed, and hydrated immediately. I expect you in the dungeon in one hour." Sir commanded simply.

"Of course, Sir." I replied, rising from the bed to shower.

The "dungeon" was in reality just the basement adult toy room, but it was done up with dim lights in a stone motif. Sir had all sorts of bondage devices and every toy imaginable down there. In the 6 months I had been with him, we still hadn't used everything.

I met Sir in the dungeon 5 minutes before my hour was up. No sense in pushing the boundaries that early in the day.

"Good morning my boy. Lay down on your back here." Sir said, pointing to the wide, flat bench inside a steel frame that looked like a modified weightlifting power rack.

I nodded and laid on my back. Sir grabbed my legs and pulled them up into the air, pushing my knees back slightly towards my chest, and exposing my tight asshole for use. He slid a bar under my knees and locked my legs to it with some thick leather before attaching it to the uprights of the rack.

I loved feeling exposed like this and my cock hardened quickly.

"Such a horny man whore you are!" Sir exclaimed seeing my hard member.

"Yes Sir, I am."

"Perfect for today's activity" Sir said as he fastened my arms down to the side of the bench with more leather straps. My breath quickened as my nerves grew. I rarely got restrained this much and I knew something different was on the menu today.

Sir put a strap across my chest, truly pinning in me place. I watched him grab the deep black hood that covered my eyes but left my mouth open. He made sure it was snug around my eyes and the world went dark.

"Can you see my boy?" He asked.

"No sir, I am blinded by the hood."

"Very good. Today we are going to play a guessing game. My friends and I will take turns fucking you with various items. Your job is to guess what that item is. It could be a toy or anything from the house. Get it right and I reward you with 30 seconds of stroking from the Venus milking machine." Sir paused.

"Ooh, that's my favorite Sir. Thank you." I said as I felt him place the tight sleeve of the aforementioned machine over my cock. He turned it on briefly.

"Mmmm, thank you Sir" I moaned. I let out a sigh as he turned it off and went on with the rules.

"Get it wrong my boy, and you will get a cock shoved down your throat.

I swallowed hard

"Are you ready to play?"

"Yes Sir..." I said nervously.

A few moments later I heard two sets of feet coming down the steps. It was the friends Sir had talked about.

"My Sub, Sirs Mike and Alex are joining me today. They will tell you who they are before putting their cock down your throat if you guess wrong." Sir said.

"Hello Sirs. I hope I can please you today." My nerves grew even more. Somehow that made my cock even harder inside the tight sleeve of the machine.

"We'll start with something that should be easy to guess to warm you up," my Sir said as I felt cold lube coat my hole.

Immediately I felt something being pushed hard against my ass. My body resisted at first but soon gave way to the intrusion. I tried to focus on what it could. I felt a number of bumps and it felt like it was getting wider. I moaned loud and tried to squirm as Sir began to pump the unknown object in and out of me. My cock twitched every time it was shoved inside.

"Mmm, that feels good Sir." I said.

"Yes but what is it?" He asked, shoving it in once more quickly.

"Aghh, I think it's anal beads Sir." I ventured.

"Correct, great job Boy."

I heard a click and the milling machine immediately started tugging on my cock. I moaned loud as it slowly stroked up and down. The machine shut off abruptly mid stroke.

"Time for the next one Sub. Sir Mike is going to be testing this item."

I nodded in response. More lube hit my hole.

I felt something a bit wider and stiffer than the beads start to force its way in. My breath quickened as it Spread me open. I tried to relax and take in the feeling. It felt fairly straight and not really tapered at all. It was smooth. That was all I could feel before Sir Mike rapidly thrust it in and out of me for almost two minutes.

As I caught my breath, he asked "Okay, slut, what is it?"

"Is it a kitchen spoon, Sir?" I asked nervously.

"It is not." He said, thrusting it deep into me one more time and pulling it out quickly. I writhed against my restraints.

I heard Sir Mike walk around to the top of my head. I felt his thighs on top of my head. I opened my mouth a bit as I felt the head of his cock on my lips. His hard shaft slipped over my tongue as I sealed my lips around the member. He was quite hard but not very girthy. I sucked hard, hoping to please him. He pushed deeper into me and I arched my head back as his cock approached my throat. What he didn't have in girth he more than made up for in length. He pushed hard and the head audibly popped past my throat barrier. I gagged a bit as he began using my throat like a fleshlight. It hurt a bit as my throat massaged his cock. He grunted loud as he backed out, releasing my throat back to me. I gagged and gasped for air. His dick slapped me across the cheek.

"What an excellent Sub you have here" Sir Mike said to my Sir.

"Indeed he is. He is for sure going to be quite sore after today." Sir replied, pinching my nipple.

"Ahhh, thank you Sir." I said, voice hoarse from the throat fucking.

Sir Alex was next. Even more lube dripped down onto my hole. I tried to relax and brace for the unknown intrusion.

"Ahh, mmm, that's big" I said as something wide started stretching my hole. It was much wider than the previous items and firm. It kept stretching me as it went in, I couldn't tell if it was tapering or not. Sir Alex moved it around in circles inside me.

"Oohh, thank you Sir." I said as the motion made my cock twitch. He fucked me slowly and stayed deep with the item.

"Okay Boy, what is it?" Sir Alex asked.

"Umm...I think it that thick glass dildo with the long handle." I venture nervously.

"That is incorrect, it was a cucumber" came the reply.

He came around above my head. I felt a thick cock head press against my lips. A strong hand supported the back of my head as his cock head pushed into my mouth. Sir Alex was huge. In an instant my mouth was full. I sucked hard on the cock and got a satisfied moan in return. A second hand grabbed my head and Sir Alex pushed the head of his cock toward my throat. I gagged hard and my eyes watered as he continued to push. My throat gave way with another gag and he quickly started using me as a fleshlight.

My mouth drooled around his cock. He held me head firm as he face fucked me. I was taking shallow breaths as he thrusted, my throat sore and taking a beating. Sir Alex moaned and pulled himself as deep into me as he could. I struggled against the restraints and for air.

"Fuck yes Boy!" He shouted as I felt his cock spasm and thick ropes of cum shoot directly down my throat. I gagged again, some of his cum getting forced out and running down my face. Finally Sir Alex pulled his cock back until just the tip was in my mouth.

"Get the last drops, Slut!" He commanded.

I greedily sucked the tip of his cock and tasted the last few drops on my tongue.

"Goddamn you have an incredible sub here!" Sir alex said to my Dom.

"Indeed...my turn"

More lube drenched my asshole. The cold feeling made my hard cock twitch. Sir pressed something with a narrow tip against my now warmed up and stretched hole It slid in easily. I felt the item get progressively wider as Sir pushed on it. My greedy ass swallowed it up and I felt the base rest home.

Sir had given me an easy one. "That's a butt plug, Sir." I said confidently.

"Yes." Sir said, leaving the plug in while her turned on the milking machine mounted on my cock.

"Mmmm, yesss, thank you Sir. Ooh." The plug and the stroking machine made a very pleasurable combination that overwhelmed my senses. I squirmed on the bench.

The machine stopped abruptly and I let out an exasperated sigh.

"You cant cum yet my Boy." Sir said, roughly pulling the plug out of me.

The next item was already lined up and Sir Mike was pushing it into my opening. This one was quite wide and didn't want to go in at first. Sir Mike put constant pressure on the item and slowly I felt my hole widening to except it. I moaned loud as the wide tip went in, then it seem to get a bit narrower for a bit and it felt sort of flexible.

"Ahh, that's so big Sir." I groaned as he continued to apply pressure. It went deep inside me and I could feel another wide part stretching me, begging for entrance.

"Ooh, it's to big Sir, please." I begged but he kept pushing and the wide part pushed open my ass.

"Oww, Fuck!" I yelled out.

"That's right, take it Boy. Now what is it?"

"Uhh...hose off a vacuum or something like that."

"Nope. Bad dragon knotted dildo."

Sir Mike came around to the back of my head and leaned over me, his long hard cock landing on my lips. I arched my head back instinctively. He didn't hesitate to shove that long member right down into my throat. I gagged as he used my mouth and throat. Watering eyes and drool coated my face. He fucked me in this position and my tongue and throat massaged his cock.

"Oh fuck yes. You know how to suck dick." He praised. He grunted and pulled out of my throat, but not removing his cock completely. I could sense him stroking the shaft.

"Oh yes, take my come Boy!" He yelled, groaning as he stroked the shaft to his climax. Lots of thick, hot cum hit my tongue. Spasm after spasm filled more of my mouth, leaking out past the tip of his cock. He pulled his dick out and roughly held my mouth shut so I had to swallow his load. I gulped it down hard. He let took and I sucked in a deep breath.

Sir Mike squeezed my chest gently "Great job Boy. Next time I am going to cum in your ass"

"Thank you Sir. Looking forward to it."

With no rest, more lube hit my ass. I felt something soft and fleshy pushing against me. It slid and Sir fucked me with just the first couple inches of the item. It felt almost like a real cock.

"Mmmm, that's nice Sir." I said

"You want more?" He asked.

"Always, Sir."

He pushed in deep and I felt Sir's balls and pelvis against me. I knew at that moment he had shoved his cock in me.

"Mmmm, thank you Sir"

Sir began to fuck me fast and deep. I moaned with him and squeezed his cock with my ass. My cock bounced in the milking machine as he fucked me and I let out a little moan everytime he buried his cock deep.

I heard Sir grunt and he grabbed my legs, pushing himself in as deep as he could go. I felt his cock spasm and warm cum shoot deep in my ass.

"How does it feel to be bred by a Dom?" He said while still releasing cum into me.

"It feels great Sir. Thank you for breeding me."

He pulled out with a huff quickly replaced his cock with the inflatable butt plug. He pumped it up as big as it would go in my ass. I groaned loudly.

"Can't have you spilling any. Do you think you earned your orgasm?" Sir asked.

"I think so sir; it is up to you." I replied.

"All three of us here agree you have." Sir said turning the milking machine on high.

"Oooh, thank you...S" my voice was cut off as Sir deftly placed a large ball gag in my mouth and pulled the strap tight.

I moaned through the gag as Sir also tightened a silicone rubber loop tight around my balls.

It didn't take long before the milking machine had me moaning and writhing against my restraints. I felt an orgasm building quickly.

"Sir..." I mumbled through the gag, "may I cum please?"

"Not yet!" He said, abruptly turning off the machine. He released the straps holding my arms.

Each of the other men there grabbed a hand and placed it on their once again hard cocks.

"Stroke these two who were willing to fuck you today."

Sir commanded.

I nodded and stroked each cock with my hand. Squeezing tightly and making sure I used the whole length of the shaft.

"Good muscle Sub, Sir praises, turning the milking machine on low. Stroking those two hard dicks took my mind off the machine a bit and I wasn't so close to the edge anymore.

I jacked off the men for a few minutes before they pulled their cocks out of my hand and Sir turned the milking machine back up. I heard the sounds of Sirs Mike and Alex stroking their cocks next to me.

I moaned loud and tried to wiggle away from the large intrusion in my ass, but that just put more pressure on prostate.

"Sir..." I forced out between shallow breaths "I am going to cum! May I please cum?" I begged him.

"When I get to one you can cum. 10, 9, " the machine turned up even faster, "8, 7, 6, 5, 4, 3, 2,...1"

"Ahh, mmmhmmm, yesss" I forced through the gag. My body convulsed into orgasm and I shot cum out of my cock more forcefully than ever before. As I came, my ass squeezed down on the large plug, heightening the sensations and forcing me to cum more. The machine continued to pump my cock as I lay there twitching in orgasmic bliss.

All of a sudden I hear two grunts from the men beside me and feel warm liquid coating my chest from both sides. Mike and Alex had glazed me in cum.

"Ooh, thank you Sirs. Thank you" I said.

"Good subs get rewarded" Sir reminded me. "I'll be back in an hour." He continued, locking my arms back down.

"Wait...what?" I asked as the milking machine started back up at a medium pace. I heard all the men leave the room as the machine worked my sensitive post-orgasm cock. I squirmed around and pulled on the restraints, moaning loud against the torture. It didn't matter the machine kept pumping away at my tired cock. I focused on controlling my breathing.

After what seemed like an eternity I felt my cock getting hard again. I relaxed a little. The milking machine sped up. Sir must have been watching and controlling it from another room. Quickly I felt another orgasm building.

"Ooh, yess, I am going to cum again." I yelled as best I could through the gag.

"Ahhh, fuck!" I climaxed again. My body convulsed hard and squeezed around the giant plug in my ass. This pushed on my prostate and I came forcefully. I was breathing hard and squirming around again, balls aching from cumming twice with a band wrapped tight around them.

The milking machine did not stop. I tried to break free of my restraints but couldn't. I heard someone enter the room.

"That must be tortuous my Muscle Sub." Sir said.

"Yes Sir..." I mumbled.

"What was that?" He said removing the gag.

"Yes Sir."

"Oh I know. Watching you though got me all hard again and I realized I was the only one that hasn't cum down your throat today. That needs to change."

Sir walked around to my head and removed the blindfold. I blinked in the light to see his hard cock and balls hovering over my face.

"Do a good job and I turn the machine off."

I nodded agreement and opened my mouth as an invitation to his cock.

Sirs familiar cock passed over my lips and I sucked passionately. He gave satisfied moans and pressed his member slowly down into my throat. The throat barrier gave way with an audible pop. Sir knew that was his cue and started fucking my throat. I gagged around his thick member, breathing hard but that only encouraged him to go faster.

I felt the speed increase on the milking machine and my hips started to move with it as my third orgasm was building. My abs clenched and hips rocked. I moaned against Sir's cock in my throat. He knew I was close. I heard him grunt and felt him tense. His orgasm was soon too.

As the third orgasm hit me, my already drained balls contracted hard, trying to force out any remaining semen. My ass squeezed around the plug and my throat tensed around the massive dick filling it. Sir grabbed my head and came hard into my throat as I struggled for air. My balls twitched, dry and aching.

"Good job Boy." Sir said, withdrawing himself.

"Thank you Sir." I said hoarsely.

Sir untied me and massaged some feeling back into my legs. He led me back to my room. Locked me in a chastity cage and locked the door.

"Until next time Muscle Boy"