My ass was still on fire but there was this strange feeling that something was missing, I actually wanted that plug back in my ass. Before I could even get comfortable with the idea that a huge human rod was going to be stuffed into my gut the big man grabbed my hair, “Every whore I have ever been to had to suck my cock before I fucked her, come on little cunt, swallow it.” Having no desire to feel the rod blaze across my ass again I opened my mouth to take in the monster. He pushed the head between my lips and into my mouth toward the back of my throat. He began moving back and forth, using my mouth as a cunt, pushing deeper and deeper. His cock hit the back of my throat and my gag reflex kicked in, I had to fight it to keep from throwing up. He grabbed my hair and pulled hard, popping his cock into my throat. It felt like he was trying to reach my stomach before he pulled back allowing me to breathe then pushed it deeper still. I relaxed my throat and the pain lessened as he fucked my face. He pulled his cock from my mouth, slimy strings of spit clung to his shaft.
I was pushed back over the wedge, my ass high in the air, “I ain’t never fucked a skinny white boy before, this will be new for both of us.” Mistress Janette grabbed my hair and jerked my head up, “I haven’t heard you ask for it, bitch. When a whore wants to please her customer she begs for that cock, she makes the customer feel that he is the only person who ever fucked her, the only person who can please her. That is what I expect from you.” Before the cane could come into play I responded, “Please fuck my ass, I have never had a cock that big before I want to feel it deep inside me.” My voice was shaky and weak and, for the first time, I felt weak and very tired. I also felt fear and even a scary desire to have my ass filled again.
The head of his cock pressed firmly against my pucker and I assumed that the butt plug had opened me enough that I would not feel much pain. As the head of his cock popped into my asshole the words of my high school coach came to me, “Never assume.” I bit down hard to keep from screaming but the pain in my ass was absolutely blazing a path to my brain, only an inch or two was wedged in my ass and I was certain someone had stuffed a burning log in my asshole. My whole body tightened up trying to repel the intruder, “Relax, little bitch, I am just going to fuck you. The only question is whether we both enjoy it, or just me, I really don’t care which,” Randy explained. Mistress Annette pulled my head up so far I could hardly breathe, “You had your chance to go, that chance has passed, your body is mine for the next two hours and I will do what I want with it. Randy is only the beginning; in the next two hours you will be fucked by larger cocks, suck cock until your jaw aches, I will personally fist fuck your ass then you will volunteer to sit on a four inch wide butt plug and drive it up your own asshole. By the time we are through here you could drop a full sized brick from your ass and not even strain.”
Randy shoved another two inches into my asshole, blazing a path of pain that threatened to drive me insane. When he once again jammed hard into my asshole he gained much more ground and I felt darkness closing in. Mistress Annette jerked my head back again and spit in my face, “Don’t you dare pass out on me, if you do I will tear your asshole wide open. Now, you are a whore, you better make your customer feel wanted,” she said as she slammed my face back onto the cushion. Fighting to remain conscious I begged Randy, “Fuck my ass you bastard, make me feel it. Push that monster deeper in my ass, fuck me like a cunt,” my voice came in gasps as I tried to make it sound like I meant it. If nothing else Randy was obedient, he backed his cock out slightly then slammed it back in hard and fast then began fucking me. “I just fucked a little cunt a few minutes ago and she wasn’t near as tight as you, but since I recently blew my load it is going to take me a long time to do it again,” he said as the last inch of his cock crammed into my asshole pushing the head of his cock into my guts.
Now my pain was doubled. While he ripped my ass sideways he was punching into my colon, threatening to rip it out and shove it into my guts. He didn’t stop, he just kept on pounding my ass and I kept begging him to do so for fear of what would happen if I didn’t. It seemed like hours before his movements became jerky and he got both fists into my hair and slammed into me so hard I could hardly breathe. Just as he was about to blow his load I could feel my cock rise and a twinge of pleasure tickled inside my ass. With three bone jarring thrusts he spewed his hot seed into my ass and fell on top of me, knocking what breath I had left from my body. I was shaking from pain and exhaustion plus fear of what was yet to come. “You have ten minutes before your next guests. Clean yourself up and be ready when they come in,” instructed Mistress Annette. I rolled onto my back and looked at her, “I can’t do this any more, please let me go.” She laughed, “You ain’t seen nothin’ yet. You agreed to this and by damned you will go through with it. You are going to do exactly what I tell you or you will pay dearly for it,” she said as she wrapped her hand around my balls and squeezed hard. I bellowed in pain, “The next time I touch your nuts it will be with a riding crop. Now, get your useless ass out of here and clean up, you are starting to disappoint me, and you do not want to do that.”
It took three girls to help me to the shower, the warm water felt good. Shelly helped me clean up, “Jim, you have got to please her, if you don’t she will make the pain twice as bad and she will send you packing after she is through. Please, try to find a way to enjoy it, stop thinking about the pain, search out the pleasure and don’t ever tell her you want to leave; first off she will not let you go until she is through so it will do no good and secondly she will not be pleased with you and she will make it worse.” I was trying to figure out how she could make it worse but I didn’t even want to imagine that. After the shower I felt a little better then Shelly gave me something to drink, “It will make you feel better and there is another agent in the drink that should actually take the edge off the pain.” I drank the liquid and instantly felt energized. Then she pushed her finger into my ass with some kind of cream on it, my ass instantly felt better, “I am sorry, Jim, this cream will make your ass hurt less but it will also cause the tissue to shrink, making your ass tight again.” My ass was actually tingling and burning a little, the feeling was not only erotic but it was developing an itch deep inside that needed to be scratched; she pushed two fingers in my ass and my cock jumped.
We returned to the room and found Mistress Annette standing with two men; one looked like he could bench press trucks and the other was tall (well over six feet) and thin, he couldn’t have weighed more that 200 pounds. “Jim, meet Bobby (the truck wrestler) and Jeremy (the toothpick), they are your next customers.” The drug was really starting to kick in and my ass was filled with an itch to be scratched. “You now have a couple of decisions to make; the first decision is whether you will be secured or can I trust you to cooperate. If you decide to cooperate you will first receive three strokes with the cane, if you must be tied I will not cane you at all,” she said as she walked toward me. Now, I have never really had to make any hard decisions in my life, in fact this was probably the hardest; on one hand I won’t have straps cutting into my body but I must suffer the cane; on the other hand I will not be introduced to the cane but I will be anchored in place. “You have ten seconds to decide then I am going to decide for you and I can assure you my decision will be more painful than either of the choices…five seconds,” she stated. Without examining it any further I said, “I’ll take the cane.”
“Your second choice may be easier. You will suck both men’s cocks and they will both fuck your ass as well; your only chance is that you pick the right one because one of these two men will not be able to do both if he cums, the other will quickly regain his erection and be able to continue. When one of them cums they will switch whether the other is through or not. You have fifteen seconds to decide,” she stated. Too many things went through my head; if the one in my ass cums first and he can not continue I will not have to taste my own asshole; but if the one who cums in my mouth can not continue I will only have to suffer one fucking. “Five seconds,” she counted down. I was just about to answer when I heard the cane cut the air and I was lifted from the ground, “I will fuck the tall one,” I screamed before another blow could fall.
The two men dropped their pants as she directed them to, I was awestruck. The shorter of the two had a cock as big around as a coke can and about ten inches long; the taller man had a cock almost as big around and it hung almost to his knee. I didn’t know anything like that grew on a human being, both of them were freaks in their own way. Now I was really scared; my asshole had been stretched but the ointment had countered that. These guys were so large that I was going to have difficulty accepting their cocks in either hole and I was guaranteed an abundance of pain for my efforts. Jeremy began stroking his long cock and it seemed to double in size (I doubt this is true but it sure seemed that way). He looked at me as a dog would look at a piece of raw meat, “I haven’t had a sweet thing like you in a long time. I’m going to rip your ass apart then shove my shit coated, cum covered cock down your throat. Have you ever tasted shit?” he laughed. I was going into a panic, I could already feel the pain and had not been touched yet. I wanted to beg Annette to let me go, promise her payment…anything if she would just let me go, but I knew she would refuse.
I tried to keep my cool as the two girls escorted me, on shaky legs, to the wedge in the middle of the room. Mistress walked over and grabbed my hair, “Bend over and show me your ass.” Without hesitation I did as instructed and instantly felt a sharp pain in the left cheek of my ass, “That shot will do a number of things, first it will relax you a bit, not so much that you will go into a drug haze, but it will relax you. Second there is a narcotic in the shot that will lower your inhabitations and make you less resistant. Third is an aphrodisiac that will have some strange effects on your body. There is also a drug that is a slight hallucinogen, just to make things interesting. Lastly is a drug that effects the nervous system, it will intensify physical feelings; pain will feel more painful, pleasure will be much greater. It will take only a few minutes to kick in, in the mean time I need to check out your ass after which you can begin by getting Jeremy good and hard before he starts fucking your sweet little ass.” Without warning she shoved two lubricated fingers in my asshole; not only was it painful because my ass had tightened up but there was also the recent damage done to it. It was all I could do to remain bent over as she fingered my sore hole, at the same time I could feel a degree of warmth as she scratched the itch that was building, but it was making that itch worse. She pulled her fingers from my asshole and instructed the girls to prepare me.
I was placed on the wedge, face up with my head on a pillow at the lowest part of the wedge, my ass hanging over the upper part. “I almost forgot, you have three strokes coming,” Annette said as she approached with what looked like a riding crop, “Roll over on your face and keep your ass high. This time you will thank me each time the crop lands and you will make no other sound.” I did as instructed and soon heard a high pitched whistle just before the crop landed; the pain was intense and I could not help but release a cry of pain. The fire blazed through my ass and seemed to be getting worse rather than lessening, “Thank you Mistress Annette,” I said in hopes she would not count my little cry against me. The second landed with such ferocity I was certain the skin on my ass split, “Thank you Mistress Annette,” I said, very near tears now. Before she landed the next blow she stood with her feet on either side of my head, the blow landed with accuracy that could only be accomplished through much practice or a lot of luck, I vote for the first. The crop landed between the cheeks of my ass causing a burning in my ass like nothing I had ever imagined and the tip landed on one nut; the pain was like the fires of hell and I bellowed, “Thank you Mistress Annette,” as tears flowed from my eyes. “Very well, that was much better than I expected. Now, on your back and show Jeremy what a wonderful cock sucker you are.” I writhed in pain as I slowly rolled to my back, “Jeremy, please let me suck your cock,” I begged, trying to be as convincing as possible.