The Pleasure Contracts-Contract #1: Temptation

by Medium McClusky

  “Oh no, please more, Rory. Fuck me some more!” Dorothy pled. “Oh god, oh god, Rory. What you do to me!”

  She was lifting her head when his finger fit into the dimple of her asshole and pressed into it. Her ass swanned and his finger entered her body. Dorothy crossed her arms and submerged her head into them but shoved her body back, impaling herself on his finger, forcing it deeply into her ass. Rory leaned over her back to get the lube. He put some on his finger and smeared it around her hole, then pressed the coated finger into her body once more. Dorothy grunted and pressed back. His finger was soon swallowed by the tight, hot, dry orifice. He withdrew his finger and dabbed lube on his cock, lined up behind the crouching, tense woman and placed the helmet of his cock against her asshole.

  It fit into the indentation perfectly and when he pressed forward, the resistance nearly made him come. He grasped her ass cheeks and peeled them apart. Dorothy’s head rose and then dropped back to the bed, a groan rolling out of her. Her body quivered. Rory penetrated her ass, feeling the sphincter relax a little to accept him. He pulled back and shoved as hard as he could. His cock slid nearly three quarters of its length into her febrile ass. Dorothy raised her head and screamed, rocking to one side to balance herself with one hand. Her other hand disappeared between legs.

  “Ah! Oh Christ, Rory, fuck my ass!” Mrs. Hannah screamed. For a moment Rory worried about the neighbors but it was the middle of a Saturday morning. He pulled back and plunged his cock back into her twitching ass, this time knifing swiftly into her. She jumped then fucked her ass back at him, jamming herself on his steely cock. Grasping her hips, Rory thrust his stiff shaft into her ass. Mrs. Hannah screamed and screamed but her body continued to meet his thrusts, crushing them together, her ass taking him deeply each time. His orgasm roared through him and he pounded home in her body at the bottom of the last stroke. His cock convulsed in her ass over and over as he fed her his sperm. The clutching ass seemed to swallow him over and over again, pleasure rippling the length of his cock. At the end, he lost all strength and slumped over her back. Below them, he felt her vibrating hand and soon after, Dorothy Hannah shook through a very controlled but attenuated orgasm. Her head did not stop wagging and the orgasm continued to ebb and flow while Rory lay draped over her back for several minutes, his cock lodged firmly deeply in her ass.

  Her hand stopped moving and her body sagged, rocking to one side. Rory tipped back, pulling his shrinking cock from the confines of her ass. She rolled to her side and he dropped to his back.

  “Oh god.” She muttered. “Was that good for you?”

  “You could not tell? God, I am probably dehydrated from coming so much in your ass.”

  She half rolled to her back so she could turn her head and look at him. “Really? Did you like fucking my ass? I love it. I love cock in my ass. Ben used to have my ass two or three times a week when he was home. I never tired of having my ass fucked. But strapping me, God, that added something entirely new. Ben did that a time or two but then always mounted me on my back. I do love that.”

  “Shall we add it to your contract?”

  She smiled and rolled away from him without answering. After a few minutes they rose and for the first time, showered together. He took her the first time in the shower that afternoon. They napped together, tangled together on the bed, naked and sated. He woke around five and took her again, mounting her on her back while she was yet drowsy. He took her ass again later in the evening and fucked her again in the shower afterwards but he could not come, though she did, several times while he ate her under the water and fucked her from behind.

  Chapter 18: Used

  <<>> <<>>

  Rory staggered home around eleven to an empty house. He slept late on Sunday, rising to have lunch with his taciturn father and garrulous mother. He puttered and later in the day rang Dorothy’s doorbell again. He fucked her against the closed door, pounding her to a panting orgasm and leaving her staggering, sagging against the opposite wall when he opened the door and left her house. During the rest of the week, he used her body, entering her mouth, pussy and ass with regularity, sometimes all three in an evening before retiring to his own bed.

  Throughout the spring, Rory continued fulfilling the contract. Dorothy never denied him, never resisted, often climaxing soon after he entered her. One Friday, late in the night after he roused her, fucking her on the floor, on her knees, bent over the table and on her back on the bed, she confessed that the anticipation kept her aroused. Never knowing when he would appear and take her, it kept her in a state of heightened excitement so when he did appear, he could and often did enter her immediately.

  He had been on a date that night and had rubbed the girl to an orgasm while they watched a movie and then took her straight home. He dated many girls from school the months before graduation, even fucking a few of them but usually he would return to Dorothy immediately after he left the girl’s house. He took to frustrating himself, dating “good girls” who everyone knew did not fuck, did not put out and allowing them to tease him mercilessly. His apparent indifference to their attenuating charms puzzled them and two of them eventually succumbed to their own wiles and ended up with his cock slammed deep into their pussies.

  Teased or fucked, Rory would go to Dorothy’s house and either ring the bell to rouse her or open the door himself and wake her by lifting the covers and then her legs over his shoulders and entering her. Dorothy would wake and scream as he entered her, sometimes finding her unprepared and needing to wait for her body to realize he was close and smooth the way into her body.

  At graduation, he huddled with his latest date girl, fingering her through her gown and then fucking her after the ceremony was over. That night he fucked several of his liaisons but the next day, he took Dorothy day and night for the next two days, till she was so exhausted, raw, sore and sated she actually plead “enough” and stopped his assault on her sensual senses.

  Then in June, he saw Lisa. They talked several times but said nothing. She took a job in a local restaurant as a waitress and Rory would go there and sit drinking coffee, watching her. When she came to talk to him, he would get up and leave, usually going to fuck Dorothy. The first couple times, he beat Dorothy relentlessly, bruising her and marking her which remained evident on her body for days afterward. Dorothy screamed through orgasm after orgasm. The third time, Rory tied her and fucked her, binding her to her bed face down while he took pussy and ass in that order. She bucked through orgasm after orgasm. He followed that up with several different versions of binding her, tying her spread-eagled on the bed and leaving her while he went on a date, returning to fuck her senseless.

  The first time he asked Lisa out again, he fucked Dorothy for three hours after leaving Lisa. He told Dorothy about the girl and how he felt about her. Dorothy said nothing. Rory stopped dating other girls. He went out with Lisa, doing stuff like shooting trap at a shooting range or going swimming. They rarely touched and did not speak about their past experiences. After each time around Lisa, Rory retreated to Dorothy’s house and fucked her relentlessly, calling orgasm after orgasm from her quivering body. In mid-July, Lisa packed up and left town, moving to be with her mother in California where she had entrance to a two-year college. She kissed Rory on the mouth the day she left, the first kiss since her return and then she was gone.

  Rory went to Dorothy’s house and sat drinking the offered coffee, staring at his hands. Dorothy, who had learned to take cues from his mood, did not speak or touch him. No few times, she had been too aggressive or assertive and found herself bent over the table or couch or easy chair receiving a thrashing that left her weeping and bruised before he pulled her to the bed and flung her onto her back and fucked her levitating, pulsating and quivering body. She learned to follow his mood or, if she desired a thrashing, to defy it. The next day he did not touch her either. And the next. And the next.

  After six days, she suggested they clean Ben David’s office. Often
in the past he had asked her if she was going to clean it out and she always hesitated and he let it drop. When she suggested it, he lifted his head and they set to work. Gradually the submerged sexuality in him reemerged and he recovered from whatever evil spell Lisa had left on him. But he did not resume his usage of the woman bound to him by the contract. During a particularly hot afternoon, he asked Dorothy if she would teach him about sex, how to “take a woman so she wanted to be taken again” and she smiled, a careful, private smile. “I think you have mastered that quite adequately.” She told him.

  He smiled and took her in much the old fashion, thoroughly and pleasurably.

  Through the remaining weeks before he left for college, she told him one day of her sexual dream, of a fantasy and the next day he would seek to fulfill it. He raped her one night, dragging her to the floor of her own kitchen and fucking her, clad in black tee-shirt and mask. He ate her for a whole afternoon. She bought a vibrator designed for the ass and had him fuck her while the thing buzzed inside her, tickling his cock as she rode him, she ground her cunt onto his cock, taking it deeply into her, feeling the vibrating instrument against his cock buzzing deep inside her ass. He used it on her till they both convulsed with orgasm. She had him cuff her to the bed and lick chocolate and honey off her tits, her stomach, her back, her pussy. She asked him to take her ass for a whole week, over and over again, as many times as he could, twice and three times a day till she walked as though her ass was open, twisting her hips around her asshole. When she moved, it was as though she felt his cock were still in her. She went through a phase where she would entice him into her pussy and then shove a finger up his ass when he was buried deep in her body.

  His departure for college did not disturb her. She kissed him chastely on the lips the day before he left. His parents helped him load the car but when they were ready to go, he entreated them to let him “spend some time with her before leaving”. They waited while he dashed up the street to her house and let himself inside. He fucked her against the door, leaving her panting and gasping, his cum leaking from her quivering body. Her smell clung to him. His parents drove him to college with the windows down but made no comment. His new roommate at college was impressed with the aroma of stale pussy that lingered about him when they shook hands. Peter looked at his hand after shaking and then sniffed it with a wry grin.

  The first semester was arid, sexually for Rory. He went home for his mother’s birthday in October and celebrated it by fucking Dorothy. It was a quiet, gentle encounter, almost like lovers and Dorothy fairly glowed with the attention. Then Rory saw Lisa on the street and learned she had lost her bid to go to college, she did not elaborate. “She did not go” was the best explanation he could garner with careful questioning of those whom he thought might actually know. They were not many. He returned to Dorothy and took her hard and fast before returning to school. He thought about her often at school while he adjusted to the rigors of college academics, succeeding in most respects. At Thanksgiving he celebrated with his parents, staying at the house till his father was pleasantly drunk.

  “I am going out.” He told his subdued mother.

  Mary smiled wistfully, glancing past him at the snoring Frenchman in her front room. “Spending the night with Mrs. Hannah?” She asked casually as if it were the most normal thing in the world to be asking her son.

  Rory glanced at her, shrugged then nodded, deciding that if his Mother wished to have that conversation, he would let her.

  All Mary McQune did was nod. She asked nothing else, volunteered nothing else. It was that night that she found the contract, a fact Rory would not learn till after he returned from college the next spring. He took Dorothy twice and they slept. The next day they went out, braving the cold and the crowds to walk through the new Christmas decorations and the glittering stores. In a clothing store, he fucked her in the changing room, taking her quick and hard, knowing the other women could hear their clinched wheezing and Dorothy’s muted grunts as she orgasmed. That night, Rory beat her and fucked her ass and she oozed into his arms and they slept again. He left her sated and suffering bruises to return to college.

  Chapter 19: Agreement

  <<>> The End

  Returning for Christmas, Rory found her changed. He fucked her but she did not respond till after he had come inside her twice. He considered spanking her to rouse her from the lethargy but thought better of it, discerning something had shifted for her. He waited on her and that night, after he had fucked her on her back, coming himself, leaving her filled but either unsatisfied or unaffected, he fell asleep only to be awaked by her gentle shaking.

  “Rory. Rory? Rory, wake up!”

  Rory rolled over. Dorothy turned on the light. He shielded his eyes. “What? What is the matter?” For a moment the feeling of waking in someone’s bed flooded over him, a sense of strangeness which woke him to the moment. His dreams had him back at college.

  Dorothy crept onto the bed. She held a flat Christmas present in her hands, wrapped with blue Santa paper and tied with a green bow. She did not offer it to him but sat, her head bowed over it.

  “I have something for you.” She said, but still kept it in her lap. “Rory, I...I have been upset. Not upset, just, just confused. You have my contract but...there is more to it than this. I have been trying to figure out how to tell you about it....”

  He nodded, interrupting her to give her a moment to collect her thoughts. “Yes, I know. Something is bothering you. I can tell you are only partly here. It is fine with me; you still feel great when I enter you but I am not sure it is that great for you.” He half-smiled.

  Dorothy lifted her eyes and almost smiled but slipped back into the reverie that had claimed her.

  Rory waited.

  Finally, after several minutes, she just extended the package to him. “I, I don’t know if I should do this but I am. I am tempting you with something and I am...I never...Ben David understood about how to get someone to give him a contract. I don’t. You are a young man and this, this is...oh, just open it.”

  Mystified, Rory took the box from her and held it, weighing it and his options. He looked at Dorothy; she regarded him with something akin to horror mixed with anticipation. He ripped away the paper, eschewing being delicate as an unnecessary delay. It was not time to tease her with drama. Whatever was inside, she needed him to see it even if she could not determine if it was what she wanted or not. When he opened it, he could see why.

  The box held paper; pages of documents with pictures. The top one showed an attractive red-haired woman. At the bottom was a name. “Katherine McKetterick.” Rory read. He looked up from the portrait, printed onto regular copy paper. “Should I know her?” He asked.

  Dorothy shook her head.

  He flipped to the next page. “Holy shit, Dorothy, this is a bearer contract!” Indeed, it was. The page was similar to the first page of Dorothy’s contract but with a different signature. He flipped deeper, glancing through the provisions listed till he got to the last page. He flipped that up but found something written on the back. It was handwritten in elegant cursive so it was difficult to read upside down. He turned the box around. He glanced at Dorothy; she was watching him like a hawk, her eyes wide and alert.

  The writing said: “I wish my daughters to experience the ecstasy you have given me. I need and want you to take them as soon as they are of legal age to choose such a thing. Please believe that I wish it and they need it. I will explain when next you visit.” A woman and her daughters! Rory thought. Every guy’s fantasy but then again, she was attractive but what if her daughters...he did not finish the thought preferring to return to the present and not get distracted by handwritten notes. He turned the box around again only to receive a new and utterly different shock.

  “Holy shit! That is....” He stopped and flipped up the portrait. A bearer contract was beneath it, with her name, Christine Strauss Evergreen signed at the bottom. “This is a professor at school. They call h
er the Ice Queen! She teaches History and....” He trailed off, the import of what he was holding striking him like a snowball. His temples throbbed.

  He paged through her contract, finding no references to daughters or anything out of the ordinary, except for a notation that “her ass is magical” on one page. Rory shook his head, stunned at what he was seeing.

  The next contract had no picture. Instead, it stated the woman was a virgin. He skipped to the next one which did have a picture. Isabella Lure was a black woman with a brilliant smile and a killer body. “Lure.” He repeated softly.

  “Yes, the same. She is CEO of Lure Cosmetics.” Dorothy offered. “She owns the company.”

  “Fuck me! Lure Cosmetics?” Rory looked up from the contract to meet Dorothy’s gaze. She held his stare for a moment before dropping her eyes. “Bearer Contracts.” He said.

  “Contracts for Pleasure.” Dorothy whispered without looking at him.

  “Pleasure Contracts.” Rory repeated.

  To this, Dorothy nodded with a private little smile which passed away without a trace. She looked up at him. “Rory, I know this...I can imagine what you are thinking.”

  Rory shook his head, “Yeah, it is easy to imagine nothing. Is this for real?”

  Dorothy shrugged.

  The motion made her breasts move beneath the satin of her nighty. Rory felt his cock waken and he shook his head.

  “What are you doing to me?” He muttered meaning nothing by it but Dorothy’s reaction was completely unexpected. She covered her face with her hands then hugged herself, wrapping her arms around her own shoulders as though she were cold.