Sissy Sex Dungeon Pt. 02

Once again I found myself alone, in this dungeon that lay deep within the house. The only comfort being the fabric of my clothing that I was currently wearing. My legs covered in only the long pink socks that stopped partway up my thigh, the back and front of which were connected to matching pink, leather garters firmly strapped around each leg. Though thin, the onsie type article covering my upper half was soft to the touch, and in any other scenario I would have felt extremely sexy in it. Almost identical to the shape of a women's one piece swimsuit, it accentuated my ass in a way that was undeniably pleasing to the eye. Tight against my torso, every curve of my body's shape visually popped. The hole on top where I had slid through to put it on, had just enough material on each side to cover my shoulder while leaving my neck and collar bone bare. That is except for the fabric that came up from my chest area to wrap around my neck and button from behind, giving me a pink collar to top everything off.

That is where the comfort ended however. Though a soft and not rough material at all, I was bound with so much black rope that I was unable to move. Both of my arms were tied behind my back, wrists together just over my lower back, so that my elbows stuck out to each side. In contrast to the bright pink thigh highs, the black rope wrapped around my ankle and the top of my bare thigh of each leg, pressing me against my calf and heels. Frogtied, I had no option but so sit on the ground with my toes and knees as support. While the lower part of my neck was wrapped in the fabric of the pink onsie's collar, the rest was covered in more of the soft black rope that was made into a leash. It down the middle of my back to the thinnest part of the clothing covering my balls and ass, before coming back up to once again wrap around my neck. What made this position uncomfortable was the thing keeping the leash tight, as it was not just a loop of rope hanging slack. At the lowest point of my neck tie, was a metal ring that the rope ran through, and the ring was the end of the anal hook currently inside me.

The onsie had been pulled to one side at the bottom, making room to attach me to the hook. I could feel the ball end, dripping with lube, inside me. Because of how tight the master of the house had made it, I was forced to tilt my head back, chest pushed outwards as I arched my back in as much as it would go. He had barely left the room, and already I could feel the discomfort of my position. Feeling both pulled forward into my arched back and chest, and down against my feet and ass. Though uncomfortable, I could still focus, and began testing the ropes in an attempt to find a way out. I had to get out of here before he returned to force me to endure more of his slave training. My throat was sore from what I just took, and I knew that was only the beginning.

With how much had already happened, it wasn't long into my squirming about that I felt the ball of the hook dig a little deeper inside me, but instead of just the steel rod, there was more pressure against my hole as the two other consecutive steel balls pressed against me. Instinctively I tilted my head down to look behind me, but only managed to put tension on the leash, immediately pulling the second, larger ball into me. I let out a moan as I immediately looked back up again, arching my back in an attempt to slacken the rope, but it was already to late.

All I could do was whimper as I tried holding this almost impossible position. My feet began to ache from sitting on them, and even though I kept my head back and chest forward, lifting my body up to relieve pressure was a mistake. A loud pitiful moan escaped my mouth as the third, and largest, lube soaked ball squeezed its way into me. My ass felt full as the cold steel dig deeper into me. It was both stimulating and uncomfortable at the same time, causing me to let out a noise that was a mix between moaning and whimpering. Arching my body even deeper was the only thing that relieved the pressure, but it was an impossible position to hold. I straightened back out, which only tightened the rope again and cause the hook to dig deeper into me again. This was a torturous back and forth as I squirmed within the ropes binding me, unable to stifle the pitiful noises escaping me.

My stamina was quickly draining, I relaxed my body more than I intended, and the hook dug itself the deepest it had yet been. I let out a cry of pain, then lost my balance and fell on my side. The brief moments of relief I was managing to get before were now completely gone. No matter how I moved, it only caused the hook to grind away inside me, but I couldn't help myself. The discomfort caused me to constantly squirm in hopes that I'd find a position to make things better. I was moaning, whimpering, and crying out as the bulbous end of this cruel contraption had its way with me.

I completely lost track of time as I struggled, trapped on my side on the cold ground. Finally I heard the door of the basement open, and the footsteps of who I could only guess was my captor approach me. I could sense him standing over me, just behind me so I couldn't see, but still I could only manage to wiggle in every direction trying to ease the discomfort.

I could hear the satisfaction in his voice as he looked upon my helpless form. "Have you learned your lesson while I've been gone? Would my little pet like to be let out of this current predicament?"

Even though I hated this man more than anything, I'd give anything to be let out of this current situation. "P-please sir...y-yes s-sir...I'll do anything...I c-can't take a-anymore..." I could barely get the words out in between the noises I was making.

I felt his hands as he began loosening the knots followed by a wave of relief over my body as the tension on my neck and back was released. I immediately relaxed against the ground and I laid there heavily breathing, grateful for it to be over. A final loud, pathetic moan escaped my lips as he grabbed the hook and slid it out of me.

He began undoing the rope around my legs and arms. "The faster you learn to be a perfect sissy fuck doll, the faster these kind of punishments stop for you. It saddened me to know that, while I was enjoying lunch up in the house, you had to be down here like this because you weren't happy to serve your master. This afternoon is your chance to try again to show me how good of a slave you are. But let's get you fed first."

I hated him more with every word he spoke, acting as if it was an honor to be used by him like this. But I was exhausted, finally able to stretch my limbs back out, and most of all incredibly hungry.

"Here, come take a rest while you eat what I brought you."

I turned to look, but only saw him sitting there on a couch nearby. Glancing around I wasn't sure where the food he had mentioned bringing was, until he undid his belt and opened his pants. I wanted nothing more than to escape, but knew that I had no more energy at the moment, and feared the consequences of not playing along. On all fours I crawled towards him, and when just a few feet away, he gently patted the cushion next to him as if beckoning a dog over. I climbed up on the couch and knelt on my legs, head over his crotch, as he pulled out his cock.

The arm closest to me reached passed me, and I could feel his hand begin to caress my ass, "That's a good girl, now eat up."

Once again I was face to face with this undeniably beautiful piece of meat, and before he had a chance to get angry, began to pleasure him. I needed this to be over as soon as possible so that I could rest and let my body recover from the past few hours. I skipped straight to the part I knew he wanted, and I'd inevitably have to endure anyways, and wrapped my lips around the head of his cock.

It was no easier than it had been earlier this morning. My tongue felt small against his girth, as I slid it down along his shaft, and my lips stretched completely as his cock filled my mouth. I could could feel the head curving against the back of my throat as it slid deeper into me, until I was facedown against his crotch as I swallowed all seven inches of this monster. Knowing what was expected of me, and ready to move on, I eagerly moved up and down, sucking on the thick warm thing filling my throat over and over. His hand continued groping my ass, eventually sliding underneath the fabric so that all he touched was my smooth bare skin. As his moans of pleasure grew more and more frequent, I could feel his fingers stop occasionally to press against my still tender hole. Finally I felt his other hand grab a handful of my hair.

"Here you go, you little slut. Eat up," and he pushed my head down against his cock so that it was as deep as it could go. Then the hand caressing my ass slid a finger inside me. I let out a muffled whimper from my stuffed mouth, as I had not yet recovered from the pain the hook had inflicted. My cry was cut short however as a rush of his cum pumped into me. I wanted to pull away from the finger now probing my insides, but he held my head in place. Once again I found myself sucking away at his cock, while it continuously pumped out his seed, as if it was the only nourishment I'd had for days. Just like before, he did not let go of my head until he went completely soft and there was no more cum to feed me.

"You've had a rough morning, haven't you? I think you deserve some rest." I laid there on the couch as he walked off, though I could hear that he hadn't left the dungeon that I was being kept in. Eventually he returned dragging a heavy stool over to where I was laying. "Come sit here while you finish recuperating."

I obliged, and stumbled my way over to the stool, not sure what to expect. Without warning I found myself pushed against the chair backing, where two built in manacles clasped around my wrists. I pulled back in vain, and as I tried twisting to see what he was doing, I was once again aggressively pushed against the back of the stool. I could feel him grab my legs, one at a time, and clasp them in larger manacles on each side of the seat of this stool. With both my thighs locked in place, I could do nothing as he then locked both my ankles in place to mechanisms lower down on the legs of the stool. I found myself awkwardly straddling the seat, facing the back, my ass hanging just off the edge.

"I was nice enough to let you rest, and it just so happens that the rest was all I needed as well. Now that you've both eaten and rested, it's time you fulfill your main purpose and have your tight little slave pussy broken in."

I immediately began to struggle against the metal clasps holding me in place. I knew this was coming at some point, but after the hook, even his finger had been to much. There was no way I could endure his massive cock that managed to fill my entire throat.

"You can struggle, and plead, and beg all you want but there's no escaping your new life purpose. I'm going to fuck your sissy ass into submission." Without hesitation I heard a snap as he began unbuttoning the buttons that held the pink onesie together beneath the crotch. Once all three were done I could feel the air against my now exposed ass, and the pressure from his head already pushing against me.

A loud moan of distress escaped my lips as my body tensed and pulled against the straps holding me in place. His lube soaked cock had no trouble sliding it's way in, and continued to steadily push its way up and deeper inside. I knew from the start of this whole situation that it would be rough when this part inevitably happened, but I had no idea it would be like this. My ass's tight hole was squeezed firmly around his cock as it forced its way further into me. If I could have made myself open up to accommodate him more I would have, but he filled me more than any other cock or toy had in the past.

I continued moaning louder and louder until I could feel his body press against my skin, meaning he was all the way inside me. He was tightly gripping my waist, making sure his cock stayed as deep as it possibly could. I struggled and squirmed harder than I ever had, trying to escape or at least give me some relief, but of course he had made sure I wasn't going anywhere. "PLEASE, I PROMISE ILL BE A GOOD SLAVE, ANYTHING YOU WANT. PLEASE HAVE MERCY, I TAKE IT ALL AT ONCE..." I begged and pleaded, the distress in my voice obvious, but his thick cock made no move. My ass was stuffed as full as possible, my hole tight around the base of his shaft, I could even feel him throbbing inside me.

I could feel him lean forward till he was almost breathing into me ear. "You're finally learning your place it seems. From now on you're going to be the best slave you can be, and give me exactly what I want like you just promised you would." I was still whimpering and shaking as he still hadn't moved his cock, but I listened in close and would do whatever he demanded to make this stop. "First lesson on being a good slave is, this is the part you were made for. All the other stuff pleasing me is just to show your appreciation for being able to serve my cock, but this is your main purpose. You can beg all you want, but no mercy will come." Immediately I began to squirm and attempt to break free, but of course could do nothing but remain shackled facing the stool.

I could finally feel his cock sliding back down and out of me, my ass immediately closing back into place as empty space was made. As I felt the tip leave my body I let out a gasp of relief, followed by heaving breathing as I tried to recoup. Almost immediately though I let out another moaning cry of pain as he wasted no time pushing back into me. It was no easier this time, his thick cock still stretching my ass to what felt like it's limit. Even though I knew it wouldn't matter I once again begged and pleaded for mercy, but there was no response this time. As soon as he was balls deep inside me, he pulled back out again, but this time he did not take it all the way out. As soon as just his head was left, he thrust back in again.

I felt totally powerless. I couldn't move at all, my cries for help were ignored, and all the while his massive cock continued thrusting into my ass at a constant steady pace. I lost complete track of time as my thoughts were consumed with trying to endure this brutal fucking, but eventually I felt him stop and pull out of me. I could feel my gaping hole twitching, and my cries for mercy turned to catching my breath.

"I put up with it for a bit, but until you learn to beg for more instead of for mercy, you're going to wear this. We'll see in a little while if you've learned you place or not." With the I saw his arms appear on either side of my face, holding a black object in front of me. As he pulled the side of it back behind me, it turned over and I tried turning my head away but there was no escaping. The black leather strap began wrapping around my face, and in the middle of it was a dildo that had to be at least 6 inches. As he pulled it back and clasped it behind my head, the dildo was forced into my mouth and partway down my throat. I tried to say I would behave, but my voice was completely muffled by the toy cock now filling my throat.

Without hesitation, the man that currently was holding me captive as his slave, slid his cock straight back into me. Even though I could barely endure it, I would have given anything for the slow pace from before. Now that I had been silenced and couldn't complain, his cock began pounding away at my ass, still plunging as deep as possible with every thrust. The dungeon of a room was almost quiet, save for a few noises. The sound of skin against my bare ass as it was fucked, the jingle of the restraints as I continued to struggle and squirm, and of course my now muffled whimpering from underneath the dildo gag around my face.

Not only was this pounding more intense than anything I'd ever experienced, the silicone cock down my throat made it hard to breathe. Because I now had to focus on keeping my throat open so I wouldn't choke, I could no long put any effort into attempting to push my ass open to ease the fucking I was taking. I was caught in a whirlwind of punishment that seemed to have no end, where no matter what I did things never improved. I started trying my best to focus my muscles on pushing my ass as open as I could, but would immediately start choking on the dildo strapped to my mouth. As soon as I managed to relax my throat enough to breathe without choking, I'd lose focus on my other end and my ass would once again be gripping tight. Back and forth I struggled, the only thing staying consistent was His thick cock pounding away.

Finally I once again felt him pull out of my body, followed by hands undoing the straps on the back of my head. "Now before I remove this from your face, you better listen, or you'll continue wearing this for the foreseeable future. Understand?" I nodded and muttered a muffled "yes sir," as I was ready to do anything to make this hell end. "I'm going to finish breaking your sissy ass in, and until I'm done you're going to act like the grateful and obedient slave you are. Not a single complaint or attempt to resist, and I want to hear from your cum swallowing mouth how much you like it and want it." With that he finally removed the strap from my face, pulling the dildo out of my mouth.

After quickly catching my breath, I immediately began to follow his orders. Anything to not have to endure that hell again. "Yes sir, I'm sorry I wasn't grateful before. Nothing would make me happier than having my pussy tight around daddy's cock." With that I gritted my teeth in preparation.

"That's a good girl." Then once again his rock hard, thick cock slid inside me, still completely stuffing me full. The closest thing to luck I'd had so far, was he was back to slow steady thrusts rather than brutal pounding. Even still, my hands tightly gripped the back of the stool I was facing, as I was determined to not squirm and seem as if I was resisting or fighting back. It took everything in me to keep my struggling focused at my hands as they dug into the chair. I wanted to cry out so bad, but made sure the only thing escaping my lips were moans of pleasure, even if forced.

I could hear him letting out grunts and little moans as he enjoyed my body at his mercy. His hands rarely left my ass, besides the occasional glide over my thighs. Now that I wasn't fighting back in fear of punishment, there was no need for him to hold my waist in place and keep me in line. He was free to caress my smooth white skin, as I obediently kept my ass in place, hanging off the front of the stool seat. I was making so much of an attempt to not be punished again, that from behind you'd guess I was having an easy time. My currently stuffed ass didn't move an inch, as the man standing behind me shoved his thick cock into a hole that obviously still to tight for the size. From the front however, my hands continued to squeeze harder and harder against the chair back in an attempt to let out the pain and frustration. My face may have been sounding like pleasurable moans, but the expression was pure hopelessness.

Of course I couldn't see behind me, but I'd bet on it that his face was one of cruel enjoyment. Even though I was playing along and following his orders, he knew I was still barely able to endure this and trying more than anything not to break. "Once you calm down and think about how lucky you are to be able to be of service like this, it isn't so bad is it? Though, I'm not hearing more than moaning. Tell me how much you love being my fuck toy, and how you can't wait for my cock to breed your pussy over and over." He continued his nonstop pumping in and out of me.

I hated this man more than anything, and wanted nothing more than to tell him to fuck off. But, being in the helpless position I was, I followed orders. "Mmm, your cock feels so good inside me daddy. It's so beautifully thick and long, you deserve to have a tight pussy to fuck with it." His thrusts started slowing which made the pain slightly easier to endure, so I kept talking hoping it'd help keep it going this way. "Thank you sir, that feels so amazing. My body was made for your pleasure, and I want nothing more than to feel your cock pump it's load inside me."