The Pleasure Contracts-Contract #1: Temptation

by Medium McClusky

  She smiled sweetly and sipped from her ginger ale. “Been with many high school girls, lately? I hear you don’t date much.”

  “Been checking up on me?” He asked. “Where are you from anyway?”

  The question turned out to be a good entre and he pulled an account of her past from her. Divorced parents. She planned to spend her senior year with her father but then he got transferred here, to this city, and his mother who had arranged to spend a month in the Caribbean scuba diving with her newest beau, a young Adonis named Lance who, as it happened, was her SCUBA instructor. The plans were made and Lisa could not remain at the high school she had attended the last two years.

  “I have to admit that having you come onto me the first thing that first day helped a bunch. I had a place on the cheer squad but girls can be so nasty, I mean bitchy don’t I? Females can be so bitchy to each other and I was feeling pretty alone. Feeling desired, that relaxed me, helped me feel like I would fit in someday. So, thank you.”

  “Does that mean you are going to fuck me?” Rory asked, stifling a giggle despite his serious intent.

  Together they laughed and then they just went for a walk through downtown. She dragged him into a shoe shop and tried on stilettos. His objections had stopped when she stood the first time and pulled the long straight dress high up her thigh to show him what a “nice pair of heels does for a girl’s legs”, to which he added his hearty agreement.

  When she suggested they look at bras, he spluttered and begged off, saying “I don’t think we know each other that well!”

  He discovered she liked to keep him off balance and the evening taught him a couple things. One was that being gracefully off-balance was charming and attractive to Lisa. The other was that shopping for sexy clothes with a woman could be an incredible turn-on, even shoes. Leaving the last store, laughing and holding hands, he had a flash of doing the same thing with Dorothy and felt a stone form in his stomach around the thought that he would never be able to do that with Dossy. That night, after he dropped Lisa off, he stopped by Mrs. Hannah’s house and she fixed him cocoa.

  She asked him “how things were going with...?”

  “Lisa.” He offered and suddenly he was recounting his two dates with the girl. He had three cups before he ran down. Rory’s eyes had been filled with Lisa and his eyes were on the street beyond the dining room window, so when he finally looked over at Dorothy, he felt sheepish and fearful. But her face glowed, her eyes twinkled. She patted his hand before grasping it.

  “Bring her here next weekend. Bring a good DVD, one you like, something musky with maleness. See what happens. I will be gone for the weekend.”

  What happened was that Rory took Lisa’s sweater and bra off and spent a fair portion of Saturday evening making careful love to her incredible breasts. Lisa ended the evening by taking his cock in her hand and caressing him to orgasm which she caught in tissues. She left them tucked in the cushion, a fact she mentioned to him only after he kissed her good night on her doorstep. He retrieved them and put them into a sealed sandwich bag and handed it to her at school the next week. She gasped delightedly and spent, she told him later, the next two days trying to deflect the curiosity of the other girls.

  The next Saturday, Dorothy arranged to be gone again. The garage door closed on the car while it was still running. When Rory shut it off, Lisa leaned over, took hold of his face and kissed him hard.

  “No movie tonight.” She said.

  “Great, I was hoping you liked NCAA football games.”

  She smacked him.

  Inside Dorothy’s house, knowing the girl was prepared to give herself to him, Rory became nervous. He could not fathom the source but then, in a moment of clarity told himself that he had two excellent reasons to be nervous. He was about to fuck his girlfriend the first time in his lover’s bed. And he was fucking another woman in the very bed where he fucked Dorothy all summer long. It was not pressure, it was the dissonance with what society expected of a “good guy” and what he was about to do, eager to do.

  When Lisa kissed him the first time in the gloom of the kitchen, his nervousness evaporated. The feel of her smooth hot skin helped when he slipped his hand up under her blouse. He had told her how much he liked the ribbed white sweater she wore that first night he kissed her. She wore it that night and he discovered getting it off was a project. It had a delicate clasp at the top in the back and he finally had to turn on a light so he could figure out how to release it. He felt awkward and even with the light, it took him several tries to master it. Lisa took it off herself. A moment later the half-bra disappeared and Rory found himself staring at her breasts again, for the first time.

  He kissed down the slope of her chest, pinning her arms behind her. Lisa was a strong girl and it would have taken more than one hand to subdue her if she wished to fight him but she merely arched her back and presented her breast to his lips. With one hand he molded the breast as he kissed it, bending her back over the counter beside the stove. The overhead light lit his progress.

  Lisa gasped loudly when his lips finally fit over her vast aureole. His tongue teased her nipple till it hardened into a solid nub under his ministrations. Lisa’s hips rocked below them, pressing her pussy at him. Her legs parted and Rory slipped his thigh between them, meeting the pressure of her pussy with his own passionate response. He kissed up the side of her bare neck.

  “Oh, oh, oh Rory!” Lisa sighed as he ran his tongue around the curls of her ear. She shivered but did not move. “Oh.” She crooned.

  She wore a straight skirt cut high on each thigh with an angled drape in front and back, it was purple swirled with blue satin. Rory found the highest boundary of the hem and touched her leg. He had glimpsed the band of her thigh-highs and now he felt the skin of her leg with his fingers. Her mouth opened to his as his hand grasped her thigh. He slid his hand higher, wanting to know if she was commando or not and found the lips of her pussy immediately. Lisa ran a hand down his chest to his belt, opened it with the button and zipper and shucked them down his legs.

  Rory knew what she wanted then and with both hands, carefully lifted the front drape of her skirt. When her hand grasped his steely cock, he shuddered. She pulled his briefs down and directed his cock towards her pussy. Her legs parted and he felt her press his cockhead against her nether lips. He grunted and she groaned together as his cock entered her. She shuddered, leaning back onto her elbows on the counter. He clasped her hips and levered her body onto his cock. He sank into her and for a moment the flashing lights in his eyes blinded, dumbed and deafened him. His hearing returned as his hips pistoned his cock into the girl. Lisa was screaming, “Fuck me, fuck me, fuck me” over and over again.

  He did. The waiting was over.

  Moments after he first shanked himself into her completely, he came, pulling free to spray his cum onto her belly. Lisa opened her eyes.

  “It’s okay. Cum in me. I am protected.”

  Rory laughed. “Too late now.” He found paper towels and cleaned her off. The kitchen, recently cleaned smelled of Pine-Sol and male semen. He led her back to Dorothy’s bed and they stripped down the covers and sheet to lie down, now nude, together.

  “Are you sure this is all right?” Lisa asked after she hugged her huge tits against him and looped her leg over his.

  Rory’s cock was rising again. “I am sure. The owners will not be back for some time. We have all night.”

  “I have to be home by two.” Lisa said softly.

  “I thought you were a woman.” Rory returned.

  She grunted and pulled him on top of her. “I’ll show you what sort of woman I am!” Lisa hissed, taking his cock into his pussy. She rocked her pussy up and the cock slid deep into her body. She groaned when he bottomed out in her. “Fuck me, Rory. Fuck me like a man!”

  He did. He came after five minutes, pouring into her with unalloyed passion. When they regained their breath, Rory got warm wash cloths and cleaned Lisa. She cooed through the cleaning. When
he was done with himself, she insisted he remain standing. She got to her knees and took him into her mouth and sucked him hard again. He took her from behind, bent over the bed, plunging into her taut cunt for twenty minutes. She came several times while he pistoned into her body. When he finally came, they were exhausted and it was only eleven. They lay down and slept. It was three when they woke with a start and made the mad dash to her house.

  The next week, she was grounded.

  Chapter 12: Grounded

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  The playoffs started and they won that week but lost a heartbreaking game, on a missed extra point, the next weekend. After the “away” game, Lisa was still grounded for, as she explained it, “being a smart ass to my dad” rather than for being home late, so it was not Rory’s fault, or so she said. Her grounding was due to expire the next day. Rory was in no mood to party with his friends that night after the loss and went home. Despite the loss, he felt ebullient.

  He had applied earlier that year to a local private college and the more distant state school. The private school did not offer much hope he would get in but he applied just because it was close. That week, he had received acceptance letters from both. The state school offered an academic scholarship.

  Instead of going directly home, he stopped off at Dorothy’s house. It was nearly midnight when he rang the doorbell. He rang it once but felt immediately that he was making a mistake. He almost left but saw a light come on and figured the die was cast. It would be rude to run off now. Dorothy opened the door in her night gown, a white diaphanous ensemble with a long, floor-sweeping dressing gown which, left untied in the front, revealed her breasts, clearly visible through the material of her chemise.

  “Dossy, I am sorry. I never thought about it being so late.”

  “You lost the game.” She said, her eyes still not wide open. “I listened to the game. Come in, please, Rory, out of the chill.”

  He stepped into the house and closed the door.

  “Where is your girlfriend?” Even in the slanted light filtering in from the distant bedroom, Rory could see the stricken look on her face. “Oh dear, I am sorry. That was thoughtless of me to say.”

  “She is grounded.” Now Rory felt his face go hot. “We fell asleep in your bed and she was an hour late getting home and then mouthed off to her dad and made it worse. Two weeks.” He wondered if this would be awkward.

  Dorothy took his hand and led him back to the bedroom. He sat on the bed and she lay down on the other side. His presence there crackled between them. His cock hardened and for a moment, he considered taking her. But he had a date with Lisa the next night, he did not feel right about such an arrangement.

  “I have some news, Dorothy.” He said into the awkward silence. He wished he had not let her lead him back to the bedroom. Last time he was there, the last thing he did was take Lisa from behind. Now the room held the mixed memories of both women. It confused him but both brought him such pleasure, he basked in both sets of memories, imagining that they did not create conflict in him but suffering from it nonetheless. He looked down at Dorothy supine on her side of the bed and the certainty that he could keep the memories from entangling him in an untoward conflict shrank.

  “Oh? What would that be?”

  “Dorothy, should I not have come here?” He asked.

  Dorothy sat up then. “I am sorry, Rory, I am sad. I was dead asleep when the bell rang and I was dreaming of Ben David. Waking in the midst of such a dream slashed me with the reality that he is gone and I feel so sad.” She lifted her gaze from the folded hands in her lap. “I am not manipulating you, Rory. I just feel sad and am not awake enough to shake it just yet. What is your news?”

  “I got into Kallsworthy and AU State.”

  “Oh Rory, that is wonderful! Kallsworthy is very exclusive.” Dorothy stood. “We must celebrate. How about a glass of wine?”

  Rory stood up. He almost said no, almost said, “that sounds like a manipulation” because it felt that way but then decided to have faith in this woman and nodded. “That would be wonderful. I thought you would be pleased.”

  Dorothy got glasses and Rory opened the bottle. “To your future, Rory!” Dorothy offered and gratefully, he drank with her. The rosé burned his throat, very dry and pungent.

  “Which do you think you will take?”

  Rory shrugged. “That is not hard to figure out. If I do not get a scholarship, it will be AUS for sure. We are not rich so Kallsworthy is not really an option. I only applied to see if I could get in.” He poured another glass for them both.

  “I fucked her. Once in your kitchen and then a couple times on your bed. It was too weird, having another woman on your bed, like that. I want to drink to you, Dorothy. I cannot but think that most women would be beside themselves with jealously or something by now. So, to you, a most remarkable woman.” Rory drank and after a slight hesitation, Dorothy matched him, draining her glass.

  “I confess, Rory, I could smell you in my bed and I had to sleep on the couch. It was evil of you to leave the sheets like that.” Dorothy was smiling despite her words.

  Rory smiled, seeing the gleam in the woman’s eyes relieved him. He could not but feel he owed her something. As if she read his mind, she brought him a request.

  “Rory, truly, I slept in the midst of the two of you most of last week and I woke aroused several times each night. I cannot lie, I had sex with myself a lot last week. Can I ask something of you? And if you do not want this, say so. I might be intruding where I have no business but, I dreamed of this twice last week and again last night.

  Rory was curious but dubious about the wisdom of giving her leave to ask something of him. Despite his reservations, he nodded. “Anything, Dorothy, you know that. Well, almost anything.”

  She smiled and nodded. “I want to be here the next time you bring her here. I want to watch you with her.” Her smile faded as the words came halting out. Her eyes took on a fearful, guarded cast. “I am not trying to start anything or anything like that. Truly, I do like to watch.”

  Before he could stop himself, Rory asked, “Did you ever see Ben David with another woman?” His mind flashed back to the “throw away” comment she had made about Ben David’s journal and that he had “other women”. He had been so fixated on Lisa, he had not pursued the comment at the time nor had he felt then that it was any of his business. But now, Dorothy was asking to watch him fuck his girlfriend. That made it his business, didn’t it?

  Dorothy looked down at her lap. They sat in the living room, now replete with her eclectic dish collection. “No, no he didn’t but, but he did arrange for someone to watch him take me.” She looked up. “Rory, I was never so excited as I was then, knowing that someone was going to be watching me, us. Ben David took me during a party and paid one of the staff to watch us, or, as Ben David said it, to keep watch for us, keep a look out. But I knew what he was doing. I had listed watching, er, I mean we had discussed watching ah, someone I knew, you know, watching them have sex, like in the next bed while Ben David was having me and, well, he was thinking of that when he took me then, testing me to see if I liked having someone watch. I did. So, well, I thought you might like it, to show me what you can do with Lisa. And I can have the pleasure of seeing you, seeing you do her.” Dorothy finished and swallowed. She poured more wine and drank most of it, forgetting for a moment, to fill Rory’s.

  Rory sat stunned. The idea never occurred to him and he did not know how to react. It should have occurred to him. His first thought was that if Lisa ever found out that he planned or allowed such a thing it would be the end for them and justly so. Guilt and arousal grew up together in him.

  He sat silently for a while, thinking about what she had suggested. “Dorothy, I cannot say it would be wise to offer you the chance to see us, see us, see us, well, to watch us. But, Dorothy, it is your house. If you are here when I bring her here, how can I object about it? But I could not volunteer to show Lisa off to
you or be part of any suggestion that such a thing would be acceptable to either of us.” He stood up, “I hope you understand. This is your house and if you happen to be home next weekend when I bring her here, that would be your business entirely.” Rory hesitated, waiting to see if Dorothy would respond.

  She did, nodding before downing the last of her wine. “Of course, I should not have asked and of course it would be fine for you to a, use the house next weekend. Don’t you think she, she, Lisa I mean would be suspicious if you don’t wash the sheets?”

  Rory shrugged. “She left tissue full of my cum in your couch the first night. I had to return and clean it up. I suppose she thinks I just clean up after. Thanks, Dossy. Good night.”

  He left the house, suddenly fully understanding the sensibility of Poe’s “The Tell Tale Heart”. He was amazed he was not screaming to be heard over the roar of his own heart beating in his ears. He parked his mother’s car and went to bed, only considering Dorothy’s words when he was safely alone in the dark. The idea of having his lover watch while he fucked his girlfriend excited him beyond words. In the silent, empty darkness he admitted it to himself and felt noble for telling himself the truth immediately followed by the sensation of being a greedy bastard. Without prior knowledge of any plan, he could be as surprised as Lisa if they were “discovered”. At the same time, he was handing Dorothy a sure way to destroy his relationship with Lisa by using her house in the first place. If she wished, she could ruin everything.

  In the dark that night, he realized something or became aware of something at least that motivated him in dealing with Dorothy. He trusted her and he wanted to know if that trust was misplaced. He trusted her to have his best interest at heart and he felt she wanted that trust and would not jeopardize it. If she wrecked his relationship with Lisa, he would know she could not be trusted. He only hoped that Lisa would not find the situation to be utterly despicable. He intended to tell her, intended to discuss his past with Dorothy at some point. Just not now, not yet. His sleep came but fitfully.