A Pain Session with Sir

"Lay back."

I do as I'm told, laying back against the metal table. It's inclined slightly, so that my head is at a comfortable angle. I can't see my naked body past the slight swell of my breasts.

"Try to relax," Sir gives me a smirk as he prepares, strapping my arms to the table, followed by my wrists. I let out a shaky breath and close my eyes, willing panic not to take hold. The next strap comes across my upper chest, then another at my waist, and yet another at my hips.

"Doing ok?"

I manage a slight nod.

"Answer me, pet."

His voice is stern and I don't want to earn a reprimand, "Yes, Sir. I'm ok."

"Good girl."

He reaches the end of the table; my tail bone just at the table's edge as my legs hang limply. Carefully, he places one leg into the stirrup, and then the other. My legs are bent back towards me in the terrible contraption, and then he spreads them impossibly wide. I can't help the whimper that escapes me.

"Be good pet, or I'll make this harder than it has to be," Sir's voice is firm and I close my mouth immediately. I press my lips together as Sir pulls the Velcro tight around each ankle and thigh. My terror ratchets up considerably as I realize I'm completely at his mercy. I can do this, I can do this, is the mantra I repeat in my head over and over.

I hear Sir placing instruments on the metal table at the opposite end of the room. Not being able to see what he's up to is torture, until I realize the torture is yet to come. After several long moments, he rolls the table over between my legs. His fingers slowly skim my thighs making goosebumps pop on my arms.

Knowing I have no other choice, I relax my head and try to slow my breathing. The next thing I hear is the snap of latex gloves. Fuck.

I can't see what he's doing, and I can't hear him over the pounding of my pulse in my ears. I just have touch. The latex clad finger presses into my pussy and I'm grateful for the lube he's used. I'm so nervous, my body isn't giving me any breaks.

"Fuck, you're tight, pet," Sir works that one finger in and out of my cunt as I try to relax. "That's it darling, don't tense up. Let me in."

His thumb finds my clit and I can't help the moan that escapes. After a moment, a second finger joins the first. Too soon, his attention is off of my clit, but I'm much more relaxed now. He tries to press a third finger inside me, and I grit my teeth.

"Relax," Sir slaps my thigh and I try to unclench all of my muscles, internal and external. He twists his fingers and presses inward. I try not to cry out, but I can't help the, "Ungh!" that escapes my tight jaw.

He stops after a moment and I hear the gloves come off. Two fingers re-enter me and I savor the feeling of his skin inside of me. For several moments I'm in heaven. Those two fingers saw in and out, slow and deep. Too soon, they're gone and I feel something cold and metal that makes me gasp.

"This is going to feel strange pet, you can make noise if you need to." I'm instantly terrified, knowing it's going to be bad if Sir is giving me permission.

The smooth cold instrument moves inside me, it's not wide, and at first I don't understand what Sir is doing. Then, I feel it so deep, pressing against my cervix and I shudder.

"Sir, what are you doing?"

He holds the instrument still and I wonder if he will punish me for asking questions.

"This instrument is going to measure the maximum length of your cunt, pet." I think about what Sir has said for a moment before the pain snaps me back to the moment. Sir presses the metal further against my cervix and I cry out, "Agh, stop stop, too deep!" I press against my bonds, trying to escape him.

"Just a little bit further pet, deep breath," Sir's voice is completely flat and calm, always so unaffected by my pain.

"Agh, I can't, stop!" I'm fully crying now, begging him to please stop.

"Ok, you did well pet, I have the measurement."

I pant for breath, my head spinning. The depth he has just measured is impossible, I never want anything forced that deep inside me ever again. He let's me relax for several moments, waiting for my breath to steady and my hands to stop shaking in their bonds.

"Alright pet, I'm going to measure width now," the words are barely out of his mouth and I'm already crying.

He places another instrument against my cunt. It feels like a very hard dildo as he presses it inwards, "You're lucky pet, this hasn't been adjusted to the new measurement we just took." I understand the threat of toys to come as I let myself cry.

"Please, don't," I'm begging as the dildo is pressed all the way in, not up against my cervix again, but still at what I would have considered maximum depth. It's like a popsicle, with a small handle extending through my opening.

Sir ignores my pleas, gripping the handle, "Ok pet, I'm going to start widening the instrument to get the proper measurement. I suggest you calm down or else I'm not going to know when you've really had enough and I'll have to make my own estimate."

His words strike fear into me and I press my lips together.

"Good girl, take a deep breath," Sir instructs and I do as I'm told. I hear a slight metallic clicking sound and the dildo presses against the walls of my pussy. After two clicks, it's uncomfortable thick and I can hear whining sounds that I realize are coming from me. Sir clicks a third time, "Ok, ok, stop, please!" I held out as long as I could.

"No baby, you can take a little more I think, we need to open you up."

I start sobbing at his dismissal, "Please, agghhh!" I let out a cry as Sir clicks a fourth time. I lay sobbing, begging him to please stop. Another click and I scream, sure that he will tear me and split me in two.

"Very good pet, no more, you did well."

Sir strokes my thigh, shushing me.

"Take it out, please," I'm begging and crying, the impossible width feeling like it's breaking me on the inside.

"I'm going to slowly pull it out pet," the words are barely out of Sir's mouth when I realize what he's saying.

"Nooo! Please, please, no," I'm sobbing and begging. If Sir pulls on the handle, the dildo will split my opening, I'm sure of it.

"Pet, calm down and breathe. Now." Sir slaps my thigh hard, twice. I try to breathe but it feels like my vagina is breaking in two. I quiet my sobs, "Please Sir don't, I'll tear, please."

"Pet, you aren't going to tear, but you need to calm down. You're going to let me open you with this device." I start begging again but he cuts me off, "Calm down now, or I'm going to rip this out of your pussy and it's going straight into your virgin ass." His words shock me into silence. Sir has never made an idle threat and I'm terrified he'll follow through. I can't stop the tears pouring from my eyes, but I don't say another word.

Sir grips the handle and starts turning the device inside of me. It feels like my insides are being torn and twisted but I try to stay as quiet as possible. Other than my small sobs and screams, I do as I'm told, and Sir tries to work the dildo out of my tight pussy. In a corkscrew motion, he starts pulling it back towards him and I feel like what I imagine giving birth feels like. My opening is pried apart impossible wide and then the pain just continues. I'm sobbing freely again and begging Sir to stop by the time the dildo exists my abused pussy. Sir ignores my cries until the end, clearly disappointed in me. I feel cold cream against my aching cunt and wish it was an ice pack.

"I was going to let you cum pet, but after that display I think you need a punishment."

I can't help the tears that continue to fall, if that wasn't a punishment, what is? I can't take anymore.

"Rest for a moment while I decide what your punishment should be. I'm very disappointed in you, pet." Sir leaves the room as I lay back and try to stop crying.

My imagination runs wild with possibilities. Several moments later when Sir comes back into the room, my heart is hammering furiously. Sir runs his hand slowly across my body, "I know this has been very difficult for you pet."

The softest in his voice doesn't put me at ease.

"Your poor little pussy was stretched horribly, and I know that hurt you."

The softness is a lie, he's taunting me.

"But, when I give you the pain that I know you need and crave, I expect you to take it more gladly. Carrying on and screaming and begging isn't how a proper sub should behave."

He's opening cabinets and placing unseen items on the metal tray.

"You need to remember that I control the amount of pain you receive, not your screams and begs." He slides the table across the floor and back between my legs, approaching my head with the gag in his hand.

"I'm going to gag you, and blind fold you," his voice is calm and low.

"No, no, please, wait!"

He ignores me, fitting the large ball gag into my mouth, pulling the straps tightly around my hand.

"Nnngg!" Tears are streaming down my face as I keep trying to beg him not to do this. The blindfold comes next, sending my world into darkness. I can't see and I have to struggle to control my sobs so that I can breathe.

I jump against the bonds when I feel his hand on my thigh. Next, I feel a lubed, gloved finger against my asshole. I loathe anal play. Sir has been very disappointed with my training so far. He has forced small plugs inside of me, but I'm so tight and it hurts so much. Anal training has turned into his favourite punishment.

"You will accept the amount of pain I decide to give you pet, your begs and pleas do not limit our activities."

The finger presses into me feeling like it won't stop. One smooth push and it's all the way inside. Soon, a second finger joins and they press inside together. My ass already burns with the stretching of my tight ring. He removes his fingers and I wait for the next instrument.

"This is going to really open you up, Pet."

Instinctively, I pull my legs away from him, but I'm immobile, no where to go.

"I have a series of four anal dilators. Each slightly wider and longer than the last. The final is very large and you will have to stretch very wide so that it fits."

He's tormenting me on purpose.

"Now, normally after the first you would beg and scream for me to stop, but I think you're just being a bit of a wimp," he chuckles to himself. "I think you will cooperate much better like this, Pet." He continues to rub his hands along my thighs, torturing me with the anticipation.

"The largest plug is almost the size of my cock, so it will be good practice for you."

His comment sets me off crying again. Sir's cock is massive, as thick around as a coke can and 9" long. Even when he fucks me gently in my pussy there's an element of pain. But, that's why he likes me. He loves inflicting pain with his giant member. Using it to force my body to stretch and expand. He will surely tear my ass with the toys he plans to use. But, that's why he's gagged me, so that he doesn't need to hear my screams.

"Try to relax Pet, here comes the first one."

He's laughing lightly, knowing that I can't possibly relax, and he doesn't care if I do. Either way, he will rape me with these toys.

It's made of very hard material and feels heavy as he pushes it into me. It feels about the size of his two fingers. I can hear the sound of the lube squelching between the toy and my tight ass. I let myself breathe, it's only going to get harder from here. Once the toy is fully embedded, Sir fucks me with it slowly a few times before pulling it out with a pop.

"See Pet? So easy." I hear the lube bottle again and then firmness against my ass. "Here comes number two."

"Nnngg!" I whine through the gag as he pushes the toy inside of me quickly. It goes deeper and the thickness spreads me more completely.

"Yes, take it Pet. Your ass is spread so lovely."

I have no choice as he fucks me slowly and deeply with the hard toy. And then, it's gone.

He gives me a moment to breathe. Two left.

"Ok Pet, bigger now."

He presses the next toy against my ass as my hole struggles to open around it.

"Ghaaa!" I try to scream despite the gag, shaking my head back and forth. It's too big. For a moment he removes it and I hope he's realized it won't fit. It's back quickly though, more lube added. This time he presses harder with a twisting motion and my body stretches around it. The burning pain doesn't stop as he pushes the toy deep inside without pausing.

"Mmm, yes darling, such a good Pet," he murmurs as he fucks me steadily with the large toy, ignoring my muffled screams and shaking head. He pulls it all the way out, and then quickly back in, forcing my tight ring to open so quickly. I'm sure my ass has torn from Sir's ministrations.

"Ahh," Sir sighs as he pulls the toy from my stretched sore hole. "Just one left, darling."

"Ok Pet," I feel lube pouring over my abused hole, "You will need to be very brave now, I know it hurts."

"Nnnn! Nnnn!"

"I know, my poor Pet."

He let's me feel the size of the toy against my thigh, rolling it so I feel the girth and length.

"It'll be all over soon Pet. Just a little more pain today and we'll be done."

He places the head of the toy at my hole, "Here it comes darling."

He presses hard on the toy, forcing my ring to spread wide and continue spreading. My whole lower body is burning pain as he presses it forward. My insides stretch wide trying to accommodate the invasion.

"Nggghhh! Nnnnnn!" Tears and snot mare my face as I shake my head and try to escape him. Ignoring me, he presses forward, forcing more of the toy into me.

Exhaustion and pain over take me and I can only lay limply and cry, wishing I could pass out and escape what's happening to my body.

"Five more inches baby," Sir whispers and I let out a sob around the gag.

The toy invades my rectum, spreading me impossibly wide as it delves into my depths. The pain and stretching feels like it will never end.

Finally, I feel Sir's hand against my body, "All the way in baby, see? So easy."

He mocks me with his tone as I lay limp and crying on the table.

He twists the toy inside me, pulling it out slightly and then back in. He takes several moments to fuck me with the toy murmuring words of encouragement.

Finally he finishes and pulls the toy from my spent body. I'm completely out of it as he undoes the bonds and lifts me off the table.

He kicks open the swinging door and lays me on the large bed in the other room, wrapping a large blanket around me.

"You did very well darling, I know that was a hard session." He produces a glass of water and a couple of aspirin.

"Once you've healed though, I'm going to fuck your ass so hard." With his words, I know the pain was real and he has torn me. Used me thoroughly. I shutter at the feelings coursing through me. It was horrible and torturous... but I want to do it again.