Sir was a close friend of mine; he was my Sadistic Dominant and I was his willing slave, his servant, and his masochistic toy when he wanted to play hard! He loved making me cry out in pain, whether it was through hard spankings, paddlings and canings that always left my butt burning hot and colored a deep shade of red with many crisscrossing dark purple welts! My desires to serve my Master and to surrender myself completely to him coupled with my deep dark need for spanking and passion for anal play were a perfect match to Sir's interests as well! Sir never tired of making me moan or hearing my muffled cries through my penis gag as he toyed with my puckered asshole. When he positions me with my ass raised and my punished red striped cheeks spread open, that puckered little hole becomes his chosen target as he fucks it hard with his own cock. Coating it generously with his own cum before lining up his arsenal of dildos which he will now use to rape my hole mercilessly! Sir just loves to stretch, ream and torment my asshole using his passion for anal play as additional punishments for me! He always strives to push past any previous limits and has lately been applying an oral numbing gel all around my asshole before he starts to ravish my hole, forcing two 10-inch dildos inside me at the same time! Sir has amassed a large collection of dildos, butt plugs, and vibrators that just keeps growing as he is in a relentless hunt for acquiring new and larger toys to torment my willing hole with! I am forced to endure more intensity with each session, and Sir has found a way to increase my humiliation even more as well. Sir will send me to specific websites that he has chosen that sell anal insertion toys, and without telling me which toy he is interested in other than knowing that it has to be large one, I am to order the item I think he is interested in using on me. Once the toy arrives, I am bound to the punishment horse and the new toy is tested out on my hole repeatedly for the evening! If I made the wrong selection, I have to reorder another item, and then accept a severe punishment from Sir before he works over my hole with the new toy! Sir loves using my bound body for lengthy forced anal play scenes. He is persistent and won't stop or release me until my hole has been raped and ravished to the point it is gaping open. Sir uses various methods but usually it involves a wide butt plug that he will use to tease and torment my tight puckered brown eye with. He works over my hole until he can tease it open just a bit where it doesn't clamp all the way closed, but shows a small pouting open hole in the middle of the puckered opening. That is when he lubes up one of the bigger toys like a 12 or 13-inch dildo and then he rams that giant toy as deep as possible and continues his assault of my hole until he has savagely raped and punished it! Sir loves fucking my mouth and asshole and giving me these anal torments that stretch my hole open for him!

As a servant to Sir, my first duties are to pleasure him and make myself presentable to him for his use of my body how ever he chooses. I have to admit I do love forced oral and Sir loves this as much as I do I think! When we first tried this, Sir had bound my hands behind my back and told me he wanted a nice oral orgasm from me. What started out as me on my knees before him soon turned to Sir holding my head and forcing his cock deeper into my mouth. He told me to relax and see how far I could go down on him. Sir said he would like me to get it all the way in till my nose touched his groin. Well, sucking I can do, deep throat will require more practice I guess. I was easily gagged and Sir stopped me after I made that chocking sound. But Sir then told me to turn around and he quickly removed the large butt plug he has me wear when I am in his home, and he said since I did not like his cock since I made a choking sound, then I could suck on my plug instead! He forced it into my mouth, and that was the first ass-to-mouth scene which Sir has repeated many times over on me! With my mouth gagged with my soiled butt plug, Sir led me to the punishment horse and secured face down, butt raised and then told me my ass would now pay dearly for my rude behavior of chocking on his cock! Sir proceeded to give me a very intense ass blistering with a wide leather slapper and then he used a wooden spanking paddle. When he had finally stopped, I was in tears, sobbing and still sucking my butt plug. Sir pulled the plug out of my mouth and asked me if I could suck his cock correctly this time. I sobbingly told him "Yes" and apologized for my poor performance earlier. I told him I would try harder next time as I wasn't too experienced with deep throating. With that said Sir held my head and again began face fucking me with his cock. I sucked his cock and licked it as best I could and then Sir just pulled himself and my head closer as he started to deep throat me again. I quickly just opened wide and let hic cock in, but as soon as I felt it hit the back of my throat I gagged again. Sir just released my head and reinserted the butt plug gag, and I saw Sir pick up the cane. Sir announced that since I had just lied to him twice, I would now be given ten of his best with the cane for each lie when I said I would try harder and when he asked me directly if I would gag again on his cock! The punishment was very severe and my muffled moans soon turned to wails as I tried to bear the harsh swats of the cane on my already hot reddened butt cheeks!

My cock and balls are kept locked into a CB3000 at all times by him. He has kept me under lock and key since the start of our relationship. Sir controls my orgasms and uses them as a reward for my exceptional performance and obedience. But Sir loves to tease my cock and balls almost daily through extended tease and denial play! I am secured face up and spread-eagle on the bed, my collar D-rings are tied off tightly to the headboard, wrist and ankles cuffed tightly to the tethers at each corner of the bed. Sir will repeatedly work me up just to the edge and then abruptly stop, only to squeeze my balls ever so hard increasing his grip as my excitement level grows! Sir likes to tease me like this through hour long or more tease and denial sessions, and then it is back into my cock cage, leaving me with a very severe case of blue balls, like last night!

Sir released me from my chastity cage and began to jerk me off. After not being allowed to cum for the last three months, I desperately wanted to orgasm tonight and to finally shoot my load! I was almost there, just moments away from my orgasm, but that is what Sir was so good at, keeping me in bondage while he unmercifully teased and denied me to cum, over and over again for hours at a time! After Sir has teased my cock right up to the brink of orgasm, just like this time, he will squeeze my balls or tap then with the wooden spoon he keeps handy! The deep dull ache he inflicts on my poor defenseless balls leaves me moaning into my penis gag, and jerking and straining against the tight bondage he has put me in! I cried out through my gag and fought against my bindings, all utterly useless attempts at freedom, but just what Sir wanted as I could see him smiling and his Sadistic gleam on his face which meant my torments were far from over tonight!

I had served Sir well tonight, greeting him at the door when he came home from work, my open mouth ring gagged and awaiting his hard cock! My hairless naked body in my submissive prone position, ass raised obscenely for his pleasures with my puckered hole, which succumbed to Sir's hard cock during a intense ass pounding which took the edge off his stressful workday! Sir then pulled his still glistening cum covered cock from my well raped hole and he held my head as his force fed me his dirty cock to clean off! I had dutifully prepared dinner and after a nice quiet meal together, Sir used my mouth once more for a longer more sensual orgasm that dumped a load of cum down my throat. But Sir's Sadistic desires were stirring again, because as he pulled out of my mouth, he purposely let a drop of his cum escape my mouth when he stroked his cock and that final drip of cum landed on my face! Sir knew I could not control any of this but that was the beauty of it all. Sir would often set me up in similar ways to fail him at some insignificant little task or infraction, only then to order me to receive a very severe punishment for my disobedience! A severe punishment was exactly what Sir extracted from my poor helpless ass this night as well! I paid dearly for my seemingly disobedient act of letting his cum escape my lips tonight. I followed Sir meekly as he led me to the punishment horse and secured me face down, ass raised up as if begging for a spanking which is just what Sir gave it, he did not disappoint! Sir told me that I would now receive a very severe punishment for my infraction of spilling his cum when I let it escape from my mouth, but with my hands bound behind me and his tight grip on my head as he face fucked my mouth, we both knew there was little that I could control during that earlier scene, none the less, my stomach churned as I awaited my inevitable fate, not knowing how bad my ass would pay for this broken rule!

Bound to the horse as I am always for all my punishments, Sir gathered a few items and laid them out before me which heightens my feelings as I know I cannot stop this and will have to endure it all as Sir punishes my butt real good with each one! So that was how it went and I received a lengthy spanking punishment from Sir with first a wooden Ping-Pong paddle, followed by a thick leather slapper, and then the most harsh of them all were the 25-swats of the cane! I really had trouble with those as each hard swat caused me to jerk my butt up in the air, even though there was little movement as I was bound tightly to the horse Sir said it appeared I was trying to move my butt away from receiving its due punishment from the cane! Plus my loud moans and cries which emanated through my penis gag were just too much and after my spanking punishment was over, Sir told me my performance was very poor and that I would have to accept an additional spanking punishment for these infractions he pointed out! Sir said that I would be receiving another punishment spanking later tonight for this and all I could think of was how my hot my reddened welted butt felt right now, and I wondered how I could endure even more!

Sir's repeated torments of my cock and balls did take my mind off my well punished backside as his tease and denials were being repeated over and over on me! Sadly for me though, Sir would just stop rubbing and teasing my cock every time I started to near the edge of ecstasy, and then he would squeeze my balls good! Each time Sir repeated this, my intensity increased along with Sir's manipulations of my cock. He would stroke it harder or faster, but his grip on my balls was also increasing as he was now squeezing them harder and for longer periods of time! The intensity of the deep dull ache flooded my senses as my involuntary actions were making me jerk hard against the thick leather cuffs securing me spread-eagled to the bed! My hips and pelvis were the only part of me that could move, even though only an inch or two at the most due to the wide leather belt securing my mid-section and my collar tightly bound to the headboard of the bed! Sir loved when I jerked hard like that, he would taunt me saying that my cock and balls were just begging him for more, harder torments like that! And, the wide butt plug Sir usually stuffs into my hole during these Tease and Denial sessions gets worked deeper into my musty hole every time Sir causes my hips to jerk violently up in the air! Sir was getting especially brutal on my balls now and my loud moans filled the room as he just tightened his hand and his squeeze not showing me any mercy but feeding off my body's agony and fueling his desires for more intense play! Then when I thought I could endure no more, his grip suddenly released my punished balls and my body dropped in a moment of recoil, my breathing heavy and panting through my penis gag! Sir would just leave me unfulfilled and tormented following each drawn out tease, the deep dull ball ache in the pit of my stomach was my punishment he would tell me for getting so close to cumming when he hadn't allowed me to have an orgasm just yet! My orgasms with Sir were only allowed as a reward for exceptional performance and obedience to him, and he said that I was hardly obedient tonight because I had to be punished earlier for my infraction! So, once again I was left frustrated and writhing in a moment of punishment after glow as Sir let me cool down a bit from the countless tease and denial torments tonight! I lay there, bound, unfulfilled, my swollen balls aching as a reminder of Sir's Sadistic touch, and wondering if Sir was finished with my teasing or was there to be yet another round of denial and torment in store for me. I looked at Sir's face and he was looking at mine with that playful but Sadistic gleam in his eyes and I knew then he would extract yet another round from my already wracked body before he would release me! This last round was excruciating to me as he gave both of my balls the hardest and longest squeeze yet as I screamed into my gag from the agony! When Sir finally released his grip on me, I didn't even hear when he announced it was now time for me to accept my additional punishment spanking from earlier today! My body was still reeling from the torments that only Sir's experienced hands could cause as he helped me up and changed my body position for access to my exposed and soon to be re-punished ass.

And now, Sir tells me he wants to progress deeper with our chastity play.

"I want to take 'your' chastity interest up to a higher level paul." Sir tells me.

"What do you mean, Sir?" I asked him.

We'd talked about seeing just how long I could go with being locked in my chastity device, all the while it is removed and then my cock and balls are teased and tormented almost daily before he locks them back up!

Sir tells me, "I think it would be fun to try a little game here paul. We could roll some dice to see how long you would be kept in chastity. That way we could possibly get into long term chastity, but with the added benefit of uncertainty"

I was frustrated at not knowing how long I would be kept locked up for, and I found it highly erotic knowing my fate rested in an arbitrary number on the dice. That neither of us controlled, and the thoughts raced through my mind as I eagerly replied to Sir with an emphatic "Yes", that I wanted to try out using the dice to determine my chastity!

"Alright paul, but just so you know, I wasn't asking for your approval, I was telling you about what I planned on doing to you next, slave!" Sir informed me as his Sadistic look came over his face again. "So I think it is time we finished up with a proper punishment for your arrogant behavior just now, in thinking you can dictate these scenes for your pleasure paul! And, don't forget, you still owe me the additional punishments when you were being too loud with your moaning earlier, and trying to jerk your butt away from me while tied to the punishment horse during your canning either!" Sir taunted as he repositioned me, on my knees spread wide apart, my face and chest resting flat on the bed, my arms pulled back between my spread knees with my wrist cuffs attached by a short chain to my ankle cuffs. In this form of hog-tie, my butt is raised high and vulnerable to whatever torments or in this case, punishments Sir has planned for me! I am effectively immobilized and forced to take all that he wants to do to me! When Sir returned to the room, I saw the cane in one hand and a huge 13"-inch black dong in his other hand. Sir proceeded to tell me that since I was moaning too loudly earlier during my punishments and jerking my butt while I was to be accepting 25-swts of the cane, he said he would just start those over from the beginning and re-apply 25 of his best to my up turned butt cheeks! But first, Sir said that I needed an attitude adjustment to remind me of my place with him as his slave and servant. So to help humble me, he said I would first receive a nice hard ass reaming with this big toy! "I am going to use this 13"-inch dildo to fuck that arrogance right out of your butt paul!" "I am going to give you a very hard anal rape to help remind you that you are my slave paul, I control your pain and your pleasures, they are for my satisfaction and enjoyment not your own!"

Sir was now twisting and pulling the fat butt plug from my hole where it had been stuffed a couple of hours earlier for my tease and denial session. Sir brought the butt plug up to my mouth and told me to open as this would be my gag to further humble me while my ass receives these added punishments!

I shamefully told Sir I was sorry for what I said before, and I didn't mean to offend him in any way. Sir accepted my apology and then he went to my backside and I could feel the lubed toy as he rubbed it around my puckered hole. "That is good paul then you will control your cries as I punish your asshole good then!" A nice hard anal rape is just what you need to humble yourself for me!" "Your moans of pain better be appreciative paul, you can show me that you are grateful for this punishment by relaxing your hole and not making your anus tight for me!" Sir said as he forcefully shoved the monstrous dildo deep into my asshole! My audible gasp told Sir that I wasn't quite ready for the sudden penetration just yet, but it was the reaction that he was hoping for! Sir controlled the scene, as always, and my feelings of fear and apprehension were now suddenly replaced with anal pain as my anus felt as if it was being stretched and ripped open back there! There was also the unmistakable feeling of humiliation as my asshole was being opened up and savagely used by Sir. I could not hide this intimate part of me as Sir was just inches away from it and giving me such a brutal fucking! I could not help but wonder in embarrassment if the dildo would show any signs of fecal matter, and if so, how severe would Sir punish me then! Or how could I face him after such an occurrence? I could only moan into my gag to console myself as Sir continued my anal punishments! After pulling the monster dildo all the way out, he would just toy with my asshole then. Slowly pushing the huge fat object into my hole, forcing my asshole to stretch wide around the shaft! Then he would just twist it and rotate it back and forth before pulling it free and starting over again! Sir would then recoat the toy with more lube and go back to deep full length penetration, all the in and all the way out! After several minutes of this, Sir then just started to rapidly fuck my hole with deep thrusts building speed as he went! Then he switched to just short jabs of the dildo, rapidly fucking my hole, forcing my anus wide while he repeatedly fucked just the massive head of the toy in and out of my sore hole! Sir was relentless as he varied his techniques, each one tormenting my asshole more and more through his different methods! Sir did not stop until he was sure he had stretched my anus wide and left my poor punished hole gaping open!

It was then that Sir asked me, "Well paul, have you had enough yet? Do you want me to stop your punishment now?" he asked.

I could only moan into my gag as I shook my head emphatically making the Yes gesture!

Sir then picked up two fat 10-inch dildos and then leaned over me as he informed me that I had NOT yet learned my position! He said it is NOT what I want, so he said there was still more arrogance left in me that he was now going to fuck out of my butt using these two dildos as he forced them into me at the same time!