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“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.

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EstherChapter 3

When we entered the dining salon, all conversation stopped. I had changed from my travel clothes earlier, but was still in black. Esther was in a peach colored evening gown. As I said before, she was ravishing. Martha and Hatty walked behind us in their evening gowns. It was plain that everyone wondered who this girl was with the Royal Executioner and the Guild Master for companions. Certainly most of the apprentices and the other Guild members had not met, or been introduced to Esther. None...

2 years ago
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EstherChapter 2

“Are the statements, that the Lord Executioner made, true?” the Village Chief demanded sternly. “Yes, Un ... Uncle,” the young man finally answered very quietly. “A week in the stocks,” the Village Chief pronounced, “and the same for those two friends of yours.” The Village Chief then turned to me to apologize. “I am sorry I doubted you, Lord Executioner. It would appear that I need to pay closer attention to what is going on with the workers in the fields.” “An excellent idea,” I replied,...

1 year ago
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Theresas Deportment

"Language Theresa!" "But Mrs. Bradshaw, I only said..." "Hush Theresa, I will not have such rude vernacular spoken in my boarding house! Also, kindly remove your elbows from the tabletop. More over, the fork was placed on the left side of your plate for a specific reason." Theresa blushed as she looked around at the other five girls, some of them putting on airs. "I never ate before with my left hand Mrs. Bradshaw." "You are a student now in the most prestigious Ladies College in...

2 years ago
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Esther III

Esther III ? by: TamarainRubber Even though we knew we were going to be late for Lisa's party, we couldn't keep our hands off each other. For the next hour or so we grabbed each other like wild cats in heat. Her breasts heaving and her lungs gasping for oxygen, Esther still found the energy to warn me not to cum. At some point she did pull my cock out from behind my rubber bloomers and shoved every inch into her mouth. The clothes she had dressed me in only made me harder and,...

3 years ago
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Katherines Style Part Two

The next day I was in full Katherine mode from the moment I unlocked her door. I greeted Sunshine just like Katherine did, using the same tone of voice and gestures. Of course Sunshine reacted just she would with her female owner. As soon as I took her for a short walk and fed her, I went straight to my bedroom, well after the prior day I felt so much more comfortable there, I wanted it to be my bedroom. I took a shower and shaved everything again. I didn't know how I was going to...

2 years ago
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Esther IV

Hope you like Esther's latest installment! ESTHER FOUR By TamarainRubber I obediently followed Esther down the long narrow hallway that led into an enormous room filled with the sounds of clinking glasses, soft whispers and a bevy of leather-clad women and men dolled up as maids, rubber babies, and crossdressing sluts like me. Strangely enough (and very much to my pleasure), there was little if any evidence of the S&M parties I had only read about, but never...

3 years ago
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Katherines Style Part 3

The front door opened and again Frank came in, a little less dramatically than the day before but no less intimidating to me as I felt timid and weak dressed in my mother-in-laws things. Frank was half expecting me to be dressed as my normal slouchy male self, ready to put a stop to all this, but he was happy when he saw I didn't have the fortitude to do that. He actually smiled at me, "There's my little wife. That dress looks nice on you." I smiled back not knowing what to do, it...

4 years ago
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Absinthe makes the heart grow fonder

Caroline dumped her books so loudly on the table that it caused Mike to look up momentarily from his laptop.“Hi, Caroline, I take it the tutorial didn’t go so well?”Caroline slumped onto the chair opposite him.“The pompous bitch basically told me to start again.”“Look I know nothing about art, I don’t even know what I like, but I do know that you know your stuff. Why don’t I get you a drink and we can talk about something else.”As Mike placed the two pints of beer down on the table, Caroline...

Fantasy & Sci-Fi
3 years ago
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Esther stone

Esther sat on the side of the road, freezing, she feared that if she didn't find a place to stay soon, she probably freeze to death.Lately life had been pretty fucked up for Esther, both her parents had die before she could barley talk, and this year she had run away, because her foster parents were abusive.She had no one now, and was stranded on the side of the road. Esther picked herself off of the ground and started walking again, until a huge house came in sight. "Warmth." She said, she was...

2 years ago
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Esther Stone part 2

When Esther had woken up the next morning laying next to Romeo, she almost freaked out, but the all of the memories from the night before flooded into her brain."Oh god." She sat up and looked at Romeo's sleeping figure next to her, his teal hair was tossed about the pillow, and he chest heaved up and down, Damn he is so hot, she thought, I acted kind of crazy last night, her face burned, ugh, what the fuck was wrong with her these days? She felt Romeo's body shift a little and her heart sped...

4 years ago
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Esther II

Esther II By TamarainRubber I had found the woman I had been dreaming about, hoping she would be my lover for years to come. Esther was the first real lady I had encountered who actually seemed to be honest about wanting to share my passions. I prayed that I would not be disappointed. From how she reacted, I didn't think I would be, but I was the planet's biggest skeptic. For the past four hours, Esther made me try on an incredibly sexy collection of female fetish wear that...

4 years ago
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Athena Goddess of Wisdom

Chapter 1 – The Birth of a Goddess Zeke cracked his knuckles and spread out his fingers. They touched the black glass in front of him and the desk lit up. A white keyboard appeared and he started to type on the touchscreen desktop. His fingers bounced around the screen, typing across the keyboard of light. You see, Zeke was a genius beyond his years. He was currently eighteen and in his second year of college. His masterful mind crossed with a youth of video games made him into one of the...

1 year ago
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Theresas Deportment

"Language Theresa!" "But Mrs. Bradshaw, I only said. ..." "Hush Theresa, I will not have such rude vernacular spoken in my boarding house! Also, kindly remove your elbows from the tabletop. More over, the fork was placed on the left side of your plate for a specific reason." Theresa blushed as she looked around at the other five girls, some of them putting on airs. "I never ate before with my left hand Mrs. Bradshaw." "You are a student now in the most prestigious Ladies College in this country...

Lesbian
3 years ago
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Athena Ch02

“You ready sweetie?” He blinked, as if coming out of a stupor and looked back to her, to Athena, her expression playful, but her body language pressing. It hadn’t been so much of a question as it had been an order. Meekly he looked back at the window, looking through his own reflection to the street outside. They didn’t have far to go, but the short walk from her limo to the Hotel’s lobby was lined by an eager group of camera-toting men, the dreaded paparazzi. “But… The photographers,...

4 years ago
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Athena

He stood hugging himself tightly, not that it helped keep him warm anymore. The cold had long since seeped so far into him the only thing that kept him from running to find somewhere warm was the fear that, should he leave his spot, he’d return to find it taken and his chance of seeing her, Athena, gone forever. The singer Athena had caught the world by storm, nobody a year ago, the young woman had taken to the celebrity lifestyle like a duck to water and was now breaking records with her...

2 years ago
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Mathew and Beth part 3 Trip down southquot

It was a warm night in Georgia when I arrived for a very special meeting, This was not about business but it was very important to him as he was coming to meet for the first time his internet “friend”. Shannon his friend was a very subservient women who was proud to be just who she was and although for this first meeting they had something a little different in mind to give her master a new experience. What she didn't know was that I had a surprise for her as well, he was a bit of a romantic...

4 years ago
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Athena 1

Athena - 1 "Look at that stream! We should stop and go swimming!" Athena exclaimed as we barreled over a small bridge in the work van. I stop the van and put it in reverse and stop again, this time on top of the small bridge. I peer out of the window and gaze upon the stream. The water was crystal clear and as still as glass. I could see an almost perfect reflection of the trees on it's surface. "but we don't have bathing suits..." I responded. My response was flirty in...

3 years ago
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Hypothermia can I survive 3 cold women

Hypothermiaby oggbashan © Copyright Oggbashan April 2003 The author asserts the moral right to be identified as the author of this work.This is a work of fiction. The events described here are imaginary; the settings and characters are fictitious and are not intended to represent specific places or living persons.****************I have a fantasy of sharing a bed with two attractive young women preferably naked. Most adult males would share that fantasy. I never expected it to happen or if it...

3 years ago
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Athena Ch 01

There was something very special about Athena. I knew it right away from the moment we met. It was more than the fact that her hair framed her face like gilt around the most perfect of portraits. It was more than the fact that she took life as a game and played it. She was carefree without being spoiled. She was innocent without guile. She was unique. It was remarkable, really, that she was so enchanting, so child like, so incredibly unselfish. She had been born into wealth. Her father had...

2 years ago
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Clothesline Leather in Lawnville

Clothesline[This story is part of the Leather in Lawnville series.]   Clothesline By DuskPetersonYou can tell a lot about a guy from where he shops. Take my friends, who have specialized tastes. Some of them spend their time at the hardware store, while others take an interest in our town's fabric shop, which has needles and pins that make them drool. Still others hang out at the department store, eyeing the cutlery collection. Somehow all of us end up rubbing shoulders at the town's jacket...

2 years ago
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Athena Corp Chronicles Chapter 3 Downsizing

“I don't like it” Ian muttered before taking a sip of his jet black coffee. “Don't like what?” Marco asked in between bites of his reheated chicken parmesan. The two sat in one of Athena Corp's many cafeterias. They were chatting over lunch, as they did most days. The talk of fellow co-workers buzzed around them. It was a cacophony of commiseration over the many drastic changes to the corporate hierarchy in recent weeks. “What do you think I'm talking about?!? The shakeup! The layoffs....

3 years ago
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Clothespin Girl Superhero

Once a upon a time, a long long time ago yesterday in fact. Today I began my plan to catch the elusive one. The one who rescues clothespins from clotheslines. The plan was a simple one to string up 7 clotheslines facing the wind knowing that if she was near that she might hear the cries of the clothespins. Now that the 7 lines were up I just had to wait and hope the wind would do it's job and carry the cries of the clothespins. This quest started years ago when I first put a clothespin on my...

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