I don’t know who I thought I was fooling. Jeremy got to his knees and I lay my head back as far as I could. He placed the head of his monster against my lips and I opened my mouth as wide as possible; I was able to get the head of his huge tool in my mouth but little more and my jaw hurt like hell but I was not going to displease Mistress Annette. I could feel the drugs kicking in and I could feel myself moving into a euphoria and my body began to relax; at the same time I could feel my cock grow firmer. After a few tries he managed to work a couple more inches into my mouth, now I couldn’t breathe but I didn’t really care. My body didn’t feel like it belonged to me, it seemed to be acting completely without my control. Mistress Annette stepped to me and began trying to push something into my asshole but it didn’t seem to fit, then she pushed harder and it popped into my ass. The ointment the girls had used had caused my asshole to shrink back to it’s near virginal size so this device, apparently a dildo, caused pain to shoot through my battered asshole. “Come on Jim, relax or this is going to be a very long day for you,” she said as she pushed the fake cock deeper. Jeremy was now fucking my face faster, forcing his cock so deep I thought my throat would rupture, “If your ass is as tight as your mouth, I am going to have a ball.
Annette was now moving the dildo in and out of my asshole but the itch was so intense that it didn’t even cause it to decrease. My cock seemed to grow harder with each thrust, I thought it was going to explode and pleasure washed through my body. When Jeremy pulled his cock from my mouth I looked at his erect monster and mumbled, “Fuck my ass, please, I need it so bad.” I was going a little crazy now, pushing my ass up to meet the painful invader in my ass. Mistress Annette pulled the dildo from my asshole causing an audible pop, “Have fun you two, but, Jeremy, not too rough, I want to see this one reach the end, look at his cock, it is as big as yours.” I reached down and spread the cheeks of my ass apart and spread my legs in an invitation as Jeremy got on his knees between my legs. He pressed first one, then two fingers into my hole, scratching that itch that had been driving me crazy but it didn’t lessen the itch a bit. His lubed fingers began to fuck in and out of my ass at a rapid pace, “Oh, yeah, that ass feels good, I think I’m in love. You know, we’re going to be here a while, I am going to fuck you until I blow my wad and lift your head from your shoulders.” From my position I could see his fingers moving in and out of my asshole; at the same time I could see my own cock standing up like spring steel.
Jeremy pushed my legs back further and pressed the head of his cock against my shit hole, then pressed further. Stars flew across my eyes as the head of his cock entered my ass, it felt like he had shoved the whole thing in my ass, but it was only the head, I could see the rest of it threatening. Bobby got into position and began trying to force his cock into my mouth, it felt like my jaw was going to break and I was really having trouble breathing. The pain and pressure in my asshole was building, I could feel Jeremy pushing deeper and deeper; I had no idea what was keeping my guts together. The pain in my jaw and my ass were excruciating; at the same time my cock was so hard it would bend steel and that itch, that terrible itch was driving me crazy, I needed to scratch that itch no matter what the cost. Bobby began fucking my mouth with what little cock he could manage to push in and was careful to allow me to breathe; hoping I could cause him to cum so I could stop that pain I worked to suck that monster cock.
Jeremy was pushing deeper still and the pain was rising as he went deeper but something was changing; riding on that pain was a wave of pleasure, a wave that began so small it almost went unnoticed then began to grow as if trying to engulf my entire body. Jeremy was doing something, or the drugs, that was heating up my body, I wanted his cock deeper and pounding in my asshole. I didn’t have to tell him that, as he rammed into my colon he began pulling out about half way then pushed back in again. Oh God, I could not understand how something could be so painful and yet feel so good that I didn’t want it to stop. He pulled his cock completely from my asshole and I could feel cool air rush in, my asshole must have been gaping wide open. Something cool and liquid was squeezed into my asshole and I smelled something that could have been mint. Jeremy placed the head of his cock at my destroyed opening and began to push again. Suddenly my asshole began to burn, not a painful, irritating burn but a strange warmth then Jeremy pushed his cock back into my waiting asshole. His cock slid into me like a hot knife through butter; the pain was still there, though lessened somewhat but the itch and the burn worked to drive me crazy.
Jeremy and Bobby set up a rhythm, both pushing into me at the same time, I must have had ten pounds of cock in my body. Bobby’s cock was something of a distraction but Jeremy’s cock was driving me to a place of pleasure I had never been before. Each time he pushed his cock in my ass he pushed a little deeper until I could feel him tearing at my guts, making my stomach cramp, but I didn’t want him to stop, that itch was still there and had to be scratched and the burning in my ass grew and the only thing that would put out the fire was his cock. Bobby started shaking and my mouth was filled with a load of his cum that almost drowned me, then fell away, “Don’t worry, little man, I will be ready to rip into your asshole in a minute.” Annette came into view, “You have another choice to make. It is evident that Jeremy is the one who will only cum once; do you want to stop and blow him until he cums and let Bobby at your ass or do you want him to keep going…choose quickly.” I didn’t have to think about it; Jeremy’s cock had been so deep in my asshole that his cock must be covered with shit and I had no desire to taste what I had already eaten, plus the fact that I didn’t want him to stop. “Fuck me,” I gasped. With that Jeremy doubled his efforts.
With Bobby out of the way I could see Jeremy going at my ass; as deep as he had driven it appeared he still had three or four inches left. Every time he pushed his cock in I could see my stomach rise and when he backed off it would fall. Aided by the lubricant he was able to move pretty freely and was fucking my ass at a pretty rapid pace. “Pull it all the way out then I want to see you buried all the way to your balls,” Mistress Annette directed Jeremy. He backed his cock all the way out, squirted more lubricant into my asshole, there was that mint smell, then began to steadily sink his cock into my stretched ass. Air being forced from my ass sounded like a long, wet fart as his cock took up space. He was still pushing my guts around and had almost all of his cock in my asshole now. I heard the whip whistle through the air again landing on Jeremy’s ass…he drove the last two inches into my gut, “Now fuck him or you will get more,” Annette instructed.
Jeremy allowed a few seconds for me to adjust then began fucking me with slow steady strokes. The pain in my ass was still far from being small and I couldn’t get away from the feeling I needed to take a monster dump but that itch was being scratched and the pain was ridden by a wave of pleasure that had me feeling more than a little aroused. My cock was throbbing and dripping cum and he began to pick up the pace, “Fuck my ass, don’t stop, please,” and I meant it this time. The pain was no where near as bad as the pleasure was good. He began pumping me like he would an old whore, fucking me hard and fast. I could never figure out why a man would want to be fucked up the ass but I was riding on the edge of an orgasm that threatened to rip me apart. He began grunting then slipped his hands under my ass and pulled me tightly to him as he slammed his cock in and out of my asshole. I could feel his cock grow then he pulled me harder against him and filled my ass with his scum. I needed to cum so bad I thought my nuts would explode and I began jacking my cock, “Get your hand away from there or I will bust your ass good,” Annette said loudly.
Jeremy pulled his cock from my ass and walked away. Bobby came over, flipped me onto my stomach with my ass high, spit on my asshole, smeared it around a little then forced half his cock into my asshole. Yes, I had just been fucked by a pretty good sized tube of meat but that didn’t seem to make any difference, I screamed in pain and shoved my face into the mat. As if to make sure he was causing me as much pain as possible he pulled his cock back all the way out and slammed it completely into my battered hole, “Now, lets fuck,” he said and began using my asshole for a punching back for his cock. It felt like he was ripping my asshole wide open and he was enjoying every minute of it. He laughed as he slammed into me without regard for the fact that he was tearing and bruising my asshole. He grabbed my hair and wrenched my head back so far that breathing was near impossible and I started blacking out, he let go, allowed be to breathe then grabbed and pulled harder as he slammed my ass. His cock felt like a three inch wide steel bar slamming into my ass. He went on and on, after about five minutes my ass was getting used to his abuse and I felt pleasure rushing in and making my cock hard again and just kept on fucking me. He slammed into my ass so hard I was certain I was bruised, then picked me up like I weighed no more than a bag of potatoes and held me while he fucked me longer and harder, bouncing me around like a puppet. He began to grunt as he slipped his hands to my nipples and dug his nails into the tender flesh. Pain and pleasure were mixed so well together that I could no longer tell them apart. When his cum finally filled my asshole I screamed with each stroke, begging him to make me cum. He threw me on the mat like so much discarded trash and walked away, my cock hard and throbbing, begging for relief.
I lay on the mat panting, trying to catch my breath. My cock was hard, my asshole destroyed and I needed to cum so bad I thought my balls would explode. Mistress Annette squatted next to me, “My, you seem to be enjoying yourself.” I looked at her, holding onto my cock, “I need to cum. Please allow me to cum, I will do anything but I need some relief,” I gasped. “So, tell me the truth, do you enjoy getting your ass fucked?” I had already been degraded as much as any man could be, admitting this was really no big deal, “Yes…it hurt like hell, but it feels so damn good at the same time.” “So, is it the pain you enjoy or the feeling of having your asshole stuffed with a big, hard cock?” she asked. I thought for a minute, it wasn’t really the pain I enjoyed so much as what the pain finally lead to, “I liked having a hard cock in my ass, fucking me like a bitch,” I admitted. She wrapped her hand around my hard cock causing it to jump, “Ok, I guess we can take care of this little problem,” she said as she squeezed my cock tightly.
She walked away and talked to the three girls who had been watching me turn into a bitch for two men with huge cocks; all four of them approached me. “Jim, you have yet another decision to make. These three girls are here for you to choose from for your next little task…which one will you choose?” asked Annette. All three of the girls were beautiful, all were young…I would happily fucked any one of them, but I had to choose, “I choose Shelly,” I said, remembering she had been so nice to me. Mistress Annette laughed, “I thought so. Well, Jim, you may have made a slight mistake, but we will see.” Once again I was taken to the wedge shaped mat and placed on my back with my ass at the edge, only this time the wedge was higher and my ass was sticking higher and my still hard cock was right over my face.
“Do you remember what I said the next task would be?” she asked. I thought but, for a moment, could not remember…then it hit me, “Yes, I remember.” “So, what is it?” I looked at Shelly, “I am going to get fucked in the ass with a fist,” these words were almost choked off with fear. Shelly stepped between my legs and began squeezing gel into my asshole and onto her hand. “Most people who do this start with a few fingers and push the hand into the orifice before closing their hand into a fist; this causes less pain and allows your asshole to stretch slowly. That is not the way we are going to do it. Shelly will work her fist into your asshole then punch your gust from the inside. She will do this until you cum, which may not be easy either. I said you may have made a mistake…if you look at her hands you will notice she has hands almost as large as a man’s. Second, Shelly can seem like an angel, but she is far from it, unlike the other girls who do my bidding she actually assists me willingly and enjoys inflicting pain as much as I do. If you think about it, she was the one who got you to touch her the first day, she is also the one who struck you the most and hardest with the cane and whip. I have a feeling you will wish you had made another choice. On the other hand, she may well be the best to relieve your pressure issue,” she smiled as she walked away.
Shelly began pressing against my opened asshole with her fist, it felt like she was trying to force a grapefruit up my ass. She began twisting her fist back and fort while applying pressure, “I was hoping you would choose me, the other girls just don’t get into this the way I do. I am going to ram my fist so deep in your ass you will never forget me and while I am fucking your ass with my fist I will allow you to jack your cock. Your job is to cum…in your mouth, every drop I see miss your mouth will mean another two minutes of fisting your ass…catch it all and I will stop when you cum.” The whole time she was talking she was applying more and more pressure, twisting and pressing until I could feel her fist almost pushing through the muscular ring, then she pushed hard and fast. Her fist popped into my battered asshole and I screamed in pain and tried to breathe. The pain was worse that I had expected…I had been fucked, fucked and fucked again by some very large cocks, I was certain this would not be so painful…wrong again. She pressed slowly but forcefully deeper into my far from virgin hole causing my bowels to cramp badly…this was but the beginning.
Once she reached the end of my dark tunnel she began pulling back out, it felt like she was dragging my guts out of my asshole, but the pressure was less. She pulled her fist all the way out, greased it up again and slammed it back into my asshole. Pain shot through my body as she drove deep into my gut, then began punching. My cock was still stone hard and I began jacking it as she started punching deep in my asshole and backing out, almost in rhythm with my strokes. As my cock began dripping precum I made sure my mouth was under it to catch every drop. Once again she pulled her hand from my ass then shoved it in again, then again and again. Pain was becoming almost as desirable as pleasure and both were building fast. With her fist deep in my asshole she began sliding her fingers along her arm and into my asshole…fire like pain burned in my asshole as raging pleasure began to take over my body. She was stretching my asshole still more but she couldn’t get her other hand in. My balls began to rumble and I knew I was seconds from cuming. My whole body was shaking and my asshole spasmed around her arm as she continued fisting me. Cum shot from my cock like it was coming from a fire hose; I kept my mouth open and captured most of it. That was the first time I had eaten my own cum…but it surely would not be the last. My body went limp as she continued fucking my ass, I really didn’t care. The last thing I remember was her removing her fist from my asshole with a pop, then the lights went out.