“How was your little nap?” Mistress Annette asked as I opened my eyes. I just moaned something unintelligible and rolled toward the voice. My body reminded me where I was and what I had been put through; I ached all over but my ass was particularly sensitive and quickly brought to mind the abuse I had been put through. “My asshole hurts,” I declared. “Yes, and it will hurt a lot more before this is all over. I think maybe it is time to explain what is really happening here. As you have probably figured out I enjoy the pleasure of abusing men and women, though men are my favorite targets, and I make a very nice living providing some special people with willing and unwilling servants and, from time to time, I select one to serve me. I recently lost my male servant, he felt he could no longer serve me and I sent him on his way,” she explained. “You seem to have plenty of men around,” I exclaimed. She smiled, “You mean Billy and Jeremy, they are just mindless pricks, tools to prepare someone to serve. I need someone who is able to think and who will help me procure other servants but I hadn’t found one, at least until you came along, now perhaps I have found that person, but we will see.”
The three girls came into the room again, “You still have one more task, and it is not an easy one. I have had a couple of people pass this one, but none have done it without being forced, that is where I am hoping you are different.” We walked into a smaller room adorned with a number of dildos of various sizes; in the middle of the small room was a narrow, low table. On that table was something that looked like a red traffic cone about nine inches high and looked to be four or five inches across, I shuddered. “I will give you two hours to get that butt plug in your asshole; once it is in place you must cum; you can cum by having one of the girls blow you or you can fuck any of them, any way you desire, but you must keep that plug in your ass, The girls will do anything you tell them, including allowing you to fuck them. If you fail to get that plug in your asshole and cum before the two hours is up you will be severely and I will either send you on your way or sell you to a master. If you are successful, you will assist me in what I do; this means you will come and go as you wish, unless I tell you to be here, to acquire the people I need. Any questions?” I thought for a moment, “If I am successful, do I get to fuck you.” She looked at me thoughtfully, “You may be sorry you asked that question, fucking me requires following my instructions and, should you fail, you will still be on your way, but if that is what you desire, so be it,” she said, then left the room.
I looked around the room and thought of the daunting task; my asshole still hurt like hell and I had to get that monster butt plug into my asshole…then cum. I looked at Shelly and the two other girls and my cock began to rise, “What do you suggest, Shelly?” She walked over and picked up one dildo that was about nine inches long and two inches in diameter, “Maybe we start right here,” she suggested. I felt my cock rise at the thought, something was happening to me; I was actually thinking about a huge rubber cock in my asshole as being something desirable. I walk to the bed against one wall then looked at the two girls. The redhead could not have been more than fourteen and, as I looked at her developing body I wanted to taste that young pussy, “What is your name,” I asked her. She smiled, “Linda.” “Linda, I want your sweet little ass laying on the bed near the top, I want to taste your sweet cunt and asshole,” I replied and she jumped on the bed and opened her young legs and exposed her sweet young pussy. I climbed onto the bed staying on my hands and knees and placed my face next to her young pussy, it smelled like cum and heaven, “I have just been fucked but Mistress Annette didn’t want me to clean up, she said you would take care of that.” She was right, I had gone from a simple man to a man willing to suck cock and get fucked in the ass…now I was going to clean another man’s cum from a young girls cunt…willingly.
I gave Shelly her instructions, she was to fuck my ass with the rubber cock, then gradually go to larger and larger cocks until I was ready to try that giant butt plug. I buried my face in Linda’s freshly fucked pussy and pushed my tongue into that cum filled hole. Shelly used a lot of K-Y to lube my asshole then pressed the head of her rubber cock against my battered hole. The head of the cock popped into my asshole quickly, meeting little resistance due to the lubrication. Fire raged in my ass as the cock slipped in and spread the walls of my stretched asshole. It still hurt, but something inside me wanted the pain as well as the pleasure of having a cock in my asshole. As Shelly fucked the cock deeper into my bruised hole I concentrated on Linda’s cunt. Even filled with cum her pussy tasted sweet with a slightly tangy flavor, I devoured her pussy, lapping and licking her then pushing my tongue deep into her used hole. Shelly was now fucking my asshole furiously causing my cock to jump every time she drove it deep into my gut. After about five minutes of using that dildo she went to the next one, which was easily an inch larger in diameter with something of a bulbous head. I stuck my tongue into Linda’s asshole and began fucking her with it, that dark hole opened like the mouth of a cave, allowing my tongue to go deep, “Yes, fuck my dirty asshole with your tongue, push it deeper.” That was when I felt Shelly press the huge dildo against my back hole and began trying to work it inside me.
I tried concentrating on Linda’s asshole and cunt but the pain in my asshole was growing as Shelly kept pushing on the fake cock. Linda grabbed my hair and held my face pressed tightly against her crotch as Shelly pressed harder, slowly spreading my asshole. I bellowed like a bull when the head of that monster popped into my ass…I was suddenly filled with fear and pain; pain like a fire in my ass and fear my asshole would split in two. I wiggled and screamed as she continued to force that monster into my asshole. I tried to tell her to stop but Linda’s pussy would not allow the words to escape and I once again tried to concentrate on the young girl’s cunt. As painful as it was there was a different kind of fire growing in my ass and somewhere in my mind I heard myself say, “Fuck me.” Linda’s clit was begging for attention so I pulled it between my lips, “Bite me,” she said and I gently nibbled on her clit, “Bite me hard,” she demanded. I bit down hard on her clit, causing her body to twitch as she raised her ass toward my mouth, “Harder…please…make it hurt.” Just as she said that Shelly pulled the monster from my asshole and slammed it back in. Without even thinking I clamped my teeth on her clit and bit down hard causing her to scream loud as her body convulsed and quaked through a bone jarring orgasm as Shelly forced the full length of that cock into my asshole. “Fuck my ass,” I begged, and she complied. There was the slightest trickle of blood coming from Linda’s clit. I was afraid I had damaged her seriously, “God, Jim, that was wonderful. Lick my clit please.” Each time my tongue touched her clit she jumped, “No, stoop, please, I can’t take any more,” so I focused on her asshole.
Shelly began pulling the giant cock from my asshole, lubed it up again and pushed it back in…then out and in again, each time my asshole allowed the cock in more easily, though the pain was still there. Pre-cum dripped from my rock hard cock in such volume that I wasn’t certain there would be any left for the main event. Shelly pulled the cock from my ass, “Are you ready?” she asked. Thinking about that monster butt plug caused my gut to churn, but I didn’t want my ass to shrink back again, “I guess so,” I said. The design of the support was such that I could rest on my knees, spreading my legs on either side of it, then push back into it and allow gravity to assist the process. I positioned myself as best I could and Shelly filled my asshole with lube then slid her hand inside easily and spread the stuff around, then put a thick coating on the plug. I leaned back into the plug and allowed half of it into my asshole before I met any resistance. I eased back up and slid back down, pushing a couple more inches inside before the pressure and pain became to great, so I sat there and allowed my ass to become accustomed to the additional width. Shelly brought a mirror over and placed it where I could see the plug and my asshole, I still had what seemed to be more to go than I was going to be able to handle; I looked at the clock, I had less than an hour.
The little dark haired Mexican girl that was with Linda and Shelly came over and pushed her pussy in my face, “Eat me please,” she said. I wrapped my hands around her firm brown ass and pulled her bald pussy to my face. She had a stronger aroma than Linda and the taste of her pussy was a little pungent, but I loved it all. Her pussy began to flow immediately as I buried my tongue between her lips and licked her protruding clit. “If you fuck me it will help,” she said as she slid down my body and sat on my hard cock, applying more pressure to my asshole, “is that ok?” Damn this little cunt was hot and I wanted my cock inside her young pussy so bad I could taste it but the head of my cock sitting at the opening of her young cunt looked huge…it would never fit, but what the hell, I had nothing to lose. As an answer I pulled her firmly against my cock and began entering that Nubian cunt, then she began pushing down. It was evident she had not had a cock this large inside her and that, though not a virgin, she had not been used much. The pain showed on her face but she continued to press until my cock was buried in her pussy, pressed against her cervix. Slowly she began to move up and down on my rigid pole.
As her pussy relaxed a little more she began moving a little faster and pressing harder. Each time she pressed down I could feel the pressure in and on my asshole, it felt like my hips would separate. She started moving faster, dropping her entire weight on me, now I was the one in serious pain, but there was a wave of pleasure along with the pain in my asshole and my balls felt like they would explode. Her movements became erratic and she slammed harder into my body, driving my cock deeper and the plug pressed harder against my hole. Suddenly she exploded, began screaming as an orgasm rushed through her body and as she climaxed she spewed hot piss and cum over my balls. I was moving closer to climaxing and I pulled her tightly to me, at the same time I felt the plug slide deeper. Suddenly the plug drove all the way into my asshole causing pain like nothing I expected and cum began flooding this young girls cunt. I couldn’t stop cuming and shaking, then collapsed in total exhaustion on the bench holding the plug in place. She finally rose from my cock on shaky legs, then I tried to stand…oooops.
The plug had me held in place. I had managed to get it completely inside and my asshole still hurt like hell, I could not escape the pain. I tried to lean forward and dislodge the plug but it was too painful, I feared I would end up with this thing in me forever. Mistress Annette entered the room, ”Well, I see you made it, having trouble getting up,” she laughed. A sharp pain hit the cheek of my ass, “When you awaken you will be fine.” Darkness fell.