Sam's Suffering

I am an experienced guy when it comes to sex. I’m aware that I’m fit and reasonably attractive. I put my asshole to work through my twenties as a submissive bottom. Lots of men fucked me hard and long and I loved it. Even if I didn’t cum, being a conduit for another man’s pleasure is hot and it’s a role I love to serve. This…this is not that.

Here I lie, bound, gagged, and alone having sex with a machine for hours. A machine that won’t get tired. If he never came back, this would be my fate.  I agreed to this. Pleasure has been too easy, I asked for pain and now I’m getting it. Being teased in challenging bondage is hot and fun. Being whipped for his enjoyment was expected and made sense. But now I’m not even being enjoyed. This is just about me and processing my pain alone. I breathe as best I can with this huge bit gag in my mouth and try to tell myself to relax and enjoy my ass. It almost works. I start to get hard, but then the machine fucks me harder and deeper like Sir said it would every twenty minutes and my dick shrivels back down. 

I was told this punishment would last two hours, meaning it should increase in speed five times. I count the fourth increase. It skewers me. Tears. I’ve seen porn of guys doing this kind of thing. I can imagine what my hole looks like. Sir Tom called it my cunt and for some reason, this humiliation stuck in my brain. Not only am I a pain slave, I am a fuckhole.

The door swings open. I turn to find Sir Tom with a friend. He appears to be a similar age, also dressed in head to toe leather, though a different design.

“Good Morning, Slave. Hope you are as uncomfortable as you look.” Sir Tom walks up to me, brushes my hair aside. The other dom views me from the foot end.

“Hello Slave Sam. Your Dom told me all about you over coffee. You can call me…well you won’t say much as I’ve been told of your wish to be remain gagged, but I am Sir Brad. I trained this handsome man torturing you right now.” Sir Brad was a stud. Clean shaven, and almost looked younger than Sir Tom.  And even taller! 6’7” I would guess. 

“I showed him the live feed of your current predicament and he agreed to help me with your torment.”

“Brave boy,” said Sir Brad. “First time doing this kind of play and you go for a weekend session. My kind of pig boy. Though he is clearly treating you harder than how I started him.”

“He can handle it. Or at the very least, he has no choice. Anyway, if you’ve been counting, you may have noticed we’re a little early.”

The machine switched to its final mode. I bite on my gag and squeal as my ass swallows the dildo. It pierces me so deep I can feel the cold metal rod in my sphincter. My toes curl, and I struggle to catch my breath as the machine jackhammers my man cunt.

“Take it, boy,” Sir Tom tells me. He licks my gagged mouth.

Sir Brad holds my balls through my jock. “Jesus, Tom. Look how his tits bounce as he suffers for us.”

“His arms struggle in their bonds. His abs go in and out as he tries to catch his breath. I told you this boy makes suffering look like art.”

“Thanks for inviting me to witness this. Is this the most you’ve ever suffered boy?”

I nod and whimper, hyperventilating.

“ Almost wanna keep him like this til session one is over.”

I look frantically at both my doms and shake my head. “NO SHIRS. PLEASH! MMM FUCK!”

Sir Tom and Sir Brad surround me, taking a nipple onto themselves to suck on. The stimulation is too much, I can’t even think straight anymore. I don’t know how long it took, but I couldn’t handle it. I soak my jockstrap from the hardest orgasm I’ve ever had. With it comes a moment of peace. I barely notice the fucking anymore.

“Should have asked for it, boy.” Sir Brad remarks.

“He’ll pay for it later.” Sir Tom adds. “But first, let him realize what it means.”

I enjoy my twenty seconds of bliss before the post-orgasm torment begins. My ass begins to hurt more and they play with my cock to make it even worse. It only lasts a minute until the machine shuts down. I breathe a sigh of relief.

“Sir Brad removes the toy from my ass and I breathe a sigh of relief. My stomach aches. I am alerted back to my sensitive bits to the feeling of Sir Brad eating my ass.

“You can do that during your time, Sir Brad.” Sir Tom adjusts the table, pushing my legs back to center. My hips are numb but they sting from the movement.

“My time starts now, doesn’t it? Two hours to acquaint myself with the slave before breakfast?”

“I suppose that’s true. How do you want him?”

“Face him towards me on the cross. I want to bond a bit and he could use some circulation after the gymnastic shit you put him through.”

I’m strapped in as ordered. My bit gag is removed and swapped back into my red ball gag.

Sir Tom takes a seat to watch as Sir Brad approaches me.

“I know you’re gotten this a lot today, and probably in life, but you are a handsome young man.”

He slaps my cock through the jock. 

“You could be out there having sex with hundreds of men.”

“He does.” Sir Tom interjects.

“Of course you do! You just look like the kind of guy who gets fucked and passed around.” 

He clocked me. 

“ But that wasn’t enough for you. Pleasure is too common for a beautiful person. Pain is exciting.” He slaps again, pulling my cock and balls out of the jock pouch. He leans in close to my face. “It’s my pleasure to hurt you, Sam.”
ZAP.

I jolt. He pokes me again with a handheld zapper on the abs.

“I love to meet a young masochist and give him what he needs.” ZAP. My ass cheek gets it. ZAP ZAP on the nipples.

“Give you a weekend that maybe you hate at the moment.” ZAP on the left nut. I squeal. “But you will go home, think about constantly,” ZAP on the right nut, “And jerk off furiously. Maybe e-mail Sir Tom asking for the video to relive it.” ZAP on the cockshaft. I retch. Sir Brad pulls my hair to lift my head up. “You’ll ask for another session.” Sir Brad sticks the zapper up my loose asshole. I freak out. He rotates the device so I feel it touching every side of my guts. I whimper, but there is no shock, and he pulls it out. “And in that session, you’ll know what that feels like for real. My arms shake in their bonds. 

“I really destroyed your cunt, Sam.” Sir Tom leans back as he speaks to me.” Understand how lucky you are.”

“It’ll snap back. He’s only thirty.”

“I’ll get a bigger cock for next time, then.”

“How many times do you get fucked in a week, Sam?” Sir Brad leans in close.

I have to stop to think. I’m zapped in the abs. It’s true what they say. Any time I get horny, which is often, I seek sex and I get it.

“Fifeen.” I get out through my gag.

“Fifteen?” Sir Brad is shocked. “More than twice a day. Fucking whore!” He fucks me again with the Zapper and I fear he will punish me for being a whore. Still no zap inside.

The next hour and a half were somewhat of a cool down. I am whipped, teased, humiliated, fingered and more. A hurricane of leather and saliva. I was exhausted when eight am came around. They release my bonds, pull my ball gag down, and give me my pants since my shirt was destroyed.

“Congrats, Sam. And thank you for being a good sport.” Sir Tom kisses me and massages my shoulders. “Come upstairs, you will have a one hour break for breakfast, coffee, and whatever else you want to do.”

“Then you’re back in my hands for eight full hours.” Sir Brad slaps my ass and leads me out for breakfast.

They treat me kindly at breakfast. I am unsure how to respond. I’m shirtless in a stranger’s home, my ball gag hanging from my neck until later, sipping coffee silently.

“Have some water, Sam.” Sir Brad passes me a glass while Sir Tom serves me a generous portion of eggs, toast, and sausage. 

“You can speak during this hour, Sam. You’re not allowed to leave, but we are taking a break due to the unplanned nature of this much extended session.”

“Okay, Sir.” I speak freely for the first time in hours, not a slave, but Sam Foster. 

“We spoke early in the morning about you Sam and decided this was fair and appropriate this one time.” Sir Brad rubs my knee kindly. “You will not be given food tomorrow, only water so please, enjoy.”

“So, tell us about your experience so far, Sam.” Sir Tom digs into his meal. I follow his lead.

“It’s been tough. Hot. I think you could tell I was turned on from most of what was done to me.”

“ How is your hole?” Sir Brad slides a finger down the back of my pants and into my crack.

“Numb, Sir. But I’ll survive.”

Sir Brad digs his finger deeper into my pants and strokes my hole. “Considering you’re such a whore, I’m a little surprised that ass torment was what did you in.”

“Yeah.  To be honest, I do have a lot of sex, but it never gets to crazy big sizes. I can take a pounding for hours, but stretching my hole was a huge challenge. I find it hot though now that it’s over.”

“With thirty-six hours to go, do you really think we’re gonna pass on the opportunity to fuck your ass again? It ain’t over, Sam.” Sir Brad sips his coffee.

“I have a new machine, speaking of. Hasn’t been used yet. Feel free to try it out on Sam.” Sir Tom turns to me with a smile. “Sir Brad loves to torture guys’ assholes, Sam. I know this first hand.”

“We all have our little obsessions. Sir Tom has a bit of an oral fixation. And you make it easy, Sam my boy. “ He grabs hold of my gag. “May I for just a moment?” I nod. Sir Brad gags me, holding my head firmly. Those full lips just want to be filled and kissed. Stand up a moment”

I do as directed.

“Your shape is impressive. Look how your belt sits on your ass. Do you work out hard?”

“Mmmhmm.” I mumble. 

Sir Tom pulls my gag down. “We’ll let you rest for a moment. I recommend you use the restroom and stretch. And by the way, this does not count as part of your forty-eight hours. You will stay until nine pm tomorrow. Understood?”

“I’m glad to hear it, sir.”

“Ho ho. This boy is committed!” Sir Tom finishes his coffee.

“I agreed to suffer for two full days, Sirs. While I appreciate the moment to recover, I would feel like I cheated at just forty-seven hours.

I did everything I needed to do in my remaining thirty minute break. Bathroom, water, and as comprehensive a stretching routine as I could fit. At the end, I was taken back to the dungeon, furniture somewhat rearranged. In the center now was what looked like a leather padded  saddle with an eight inch, thick textured dildo attached to the top.

“A sybian! Hot!” Sir Brad admired the machine that I expect will be inflicted on me in just a moment. 

 Without a word, Sir Tom dresses me in a leather harness. I like these, to be honest and thought it hugged my chest nicely. I was stripped of my pants and dressed in leather combat boots before being led to the sybian. The saddle was raised off the ground significantly and I was lifted so that I could straddle it.
“Ah fuck!” I whine as my asshole is filled. “Sir, you forgot to lube it.”

Sir Brad pulls my gag into my mouth and buckles it tightly. “I didn’t forget shit.” My wrists are pulled behind me and slapped into restraints, buckled parallel to one another up my back. I realize my harness is for bondage. “Your messy cunt does not need lube anymore. Sir Tom made damn sure of that.”

“You’re welcome, boy.” Sir Tom saluted me. I whimper in my gag as I’m forced down  on the odd dildo. With mild effort, it fits. Sir Tom really did stretch out my hole. Considering how much sex I have, I have always been rather tight. 

My booted feet dangle a couple of inches off the ground. I try to reach down with my toes to no relief. The stress of my body weight is all on my thighs and ass. My cock stiffens. Its a challenging position for sure. I have to use my core to stabilize myself, while the cock inside me is made of hard plastic, making it uncomfortable to lean too far forward or back. 

Sir Brad attaches nipple clamps to me. I wince and curse. These are the real deal. I begin to drip sweat. Sir Tom rests, watching me suffer at his master’s hands. He unzips his leathers and plays with his cock.

“ Slave. This is your punishment for cumming without asking. You will remain on this sybian for four hours. You may NOT cum. Do not even begin to beg for it. If you beg, your balls will be hurt. If you cum, your time will extend for another four hours where you will be punished further for breaking our rules a second time.

This is an odd one. It’s  kind of hot to be in a stress position, as I always find it to be. But I don’t feel the need to cum necess–

WHIRRR.

The Sybian roars to life. The toy in my ass begins to vibrate. A pad in front also rumbles and makes sure my balls feel it too.  

An hour into this treatment, my Masters get bored.

“Alright. Let’s have some more fun here.” Sir Brad pulls my back and sticks a squirt bottle up my hole. My insides are lubricated generously and it starts to feel…amazing. My cock hardens to full mast. I whimper into my gag. Sir Brad presses a button and the toy begins to spin inside my hole. The new sensation sends me into a frenzy.

“Shir I”m Unna Com!”

“If you cum, you’ll be here a long time, Sammy boy.”

I breathe deeply, trying to ignore the pleasures inside me. I adjust and the need to cum subsides. I ride the wave of pleasure, enjoying it knowing that soon enough, more whipping and shocking and who knows what else will use up my weekend.

“Good fucking boy. You’re almost there. Five more minutes to go.” Sir Brad rubs my sweaty chest.
   

 Sir Tom rises from his seat and approaches me. My doms look at each other with a scary grin.

Sir Brad grabs my shoulders and leans my back, pressing a button on the remote with his other hand. The dildo switches to a pulsing motion. He rocks me forward and back, stopping when I begin to whimper and resist. He adjusted my position so that its directly touching my prostate.

“No Gah Shir, Pls.” I scream into my gag. Sir Tom fingers my cunt to pilfer some lube and strokes my cock. “Fuhk! Not Fehr!” I groan and give in to the inevitable, blowing my load right into Sir Tom’s mouth. 

Sir Brad let’s go of my shoulders, heads to the wall behind me and returns to Sir Tom’s side. They don’t speak, but he hands his partner a bullwhip to match the one he will use to torture me for four hours. They played dirty, but I failed nonetheless. Thankfully being whipped is exactly what I crave right now.