0 comments/ 22901 views/ 1 favorites A Bad Bet By: darkindigo That was the bet; one night and no one could accuse me of being a pansy ever again. Also 20 bucks. It might seem pathetic to you, but that 20 bucks will feed me for a week. How bad could it be, anyway? Harvey sat alone in the bedroom with the lights turned off, listening to the laughter of his friends just outside, apparently still bargaining with her. The idea had been discussed innocently enough at first- theoretical strippers are still mostly harmless- but when it was suddenly upgraded to hooker, plans started getting dicey and now he was cut out of the loop altogether. The woman they found was an average looking woman with short, blonde hair. She wore a tight, red tank top over a short, denim skirt and walked with a pronounced sway in her hips. Before he was pushed through the bedroom door, she had looked him over once and smiled, showing a gleaming set of white teeth, though one in the back appeared to be missing. Lord knows what they were saying now. Quietly, he stood and tiptoed to the door. He pressed his ear flat against the wood, but recoiled in shock when the handle began to turn. Luckily, it was only one leap backwards to the end of the bed. "Paid in advance, such nice boys." She closed the door behind her and put away what looked suspiciously like a wad of bills in a small, black purse, which she then deposited near the door. "Harvey?" Her voice was a pleasant alto. "Y-yes ma'am?" "Oh heavens, darlin'. Just call me Ruby. Now, your friends have arranged a little somethin' for you. They say that you're as ripe as a new cherry and I don't rightly know if you're up for this, but I haven't turned down a sum of money quite like this before, so I haveta ask," Ruby stepped closer, her breasts just about eye level, "Are you willin'?" Little Harvey responded instantly, but Big Harvey took a moment longer. Technically, he could back out and probably no one would blame him too much, but he wasn't about to let them see him chicken out. "Yes." "All right, then." Ruby took his hands and pulled him up. With surprising sweetness, she touched his face before softly kissing him. Harvey forgot to react, so she pulled back and laughed saying, "I won't bite... yet." The next time, he kissed back. "Wait," he said when they broke apart, "Why are you... I mean, don't you just..." Once more, she laughed prettily, brushing a lock of golden hair from her eyes. "It's your first time, sweetheart; you'll remember this for the rest of your life. Besides, dirty tramps need love, too." Her sentiment was sincere, but she immediately undermined her words by pulling off her tanktop to reveal an expanse of smooth, pendulous breasts. "Go on and touch them," she said, noting his transfixed gaze. Though his hands shook, Harvey did reach out and caress both tits, feeling their weight fill his hands and rubbing her nipples with his thumbs. Impulsively, he leaned down and took one in his mouth, rolling the little bud with his tongue, making her breathe heavily. "You will be fun to teach," she stepped away and turned toward the door. Click. "Let's not let the others bother us." Ruby then bent over and reached into her purse, taking out a length of something that Harvey completely ignored in favor of ogling her beautiful ass and wondering if his hand would be smacked away from reaching under her skirt. She straightened and approached him, pushing him back onto the bed and directing him to slide back until his hindquarters hit the headboard. "This isn't something I do very often, at least not for my regulars. Your friends wanted you to have the works, so you'll have the whole package. You'll like it." She straddled him in a full kneel, her boobs bouncing around his face and prompting another attack with his tongue, and took his wrist. Swiftly, she bound it to one post on the headboard and then, before he could recover his senses, bound the other. "Hold on a minute..." "Shhh." Ruby settled back on his knees, trailing a finger down his chest. "Let me do all the work..." She pulled out a pair of scissors he hadn't seen before and, ignoring his protests, cut his black, t-shirt to ribbons. He received two kisses to the chest to assuage his annoyance, then promptly found himself without pants. Ruby grabbed his ankles and pulled him flat, then bound his ankles to the remaining bedposts. Harvey tested his bonds, pulling gently at first, then full on yanking until he gave himself minor rope burns. This nylon twine was industrial grade, apparently. "That's a good boy." She stood on the bed and he noticed for the first time that she was wearing glittery red stilettos the color of rubies. Also, she was wearing a thong and watching its string rub roughly between her lips was quite distracting. She paced back and forth over him for a moment as if she had just caught a wild tiger, then sat on his thighs facing him. Her scissors made another appearance pulling double duty by dispatching his briefs and making him fear losing his manly bits via cold metal. On the bright side, his erection was now unrestrained by jeans. Ruby touched his throbbing dick, teasing him with her fleeting fingers. He swallowed a whine, willing himself not to beg for something more. "Mmm, still not saying a word, are we?" she asked, punctuating her question with a sudden grasp of his shaft. "In this relationship, we ask for what we want. If not, then we are punished." From her back pocket, she produced the scariest, black-leather riding crop Harvey had ever seen. He had no idea how he hadn't noticed the thing before, but now that he was staring down its stick, he wasn't sure he really wanted to see it at all. "Do you understand?" "Y-yes ma'am." Smack! His left nipple was suddenly made of lightning. "What did I ask you to call me?" "R-ruby..." "That's right." Her fingertips massaged away the hurt. "Now, I think there was something you wanted from me? Something involving... this?" Ruby's lips hovered close to his tip, her hot breath making him close his eyes with anticipation. Harvey nodded, then quickly said "Yes!" when he felt leather press into his thigh. He could feel her heavy breasts settle on each of his hipbones. "Tell me what you want." "C-could... you suck me?" He was instantly rewarded with delicious heat wrapping around his cock. Her tongue stroked the backside of his shaft and swirled around his tip. While her lips caressed him, she held her breasts around him and let her warm skin hold him. She stopped altogether much too soon, sitting up and briefly touching herself before standing and letting her thong slide down her long, curvy legs and kicking it off her ankles. With delicacy, she straddled his hips again and took him in her hands. "I'm going to fuck you," she said bluntly. "Do you want me to?" "Y... yes." "Ask nicely." He gasped as her lips rubbed against his head. "P-please." She complied, letting him slide inside her so slowly it made his toes curl. When he felt her clench around him, his head fell back and he thrust upwards to feel as much of her as possible. Ruby moaned softly, rising and falling again. He was better prepared for the sensation this time, but when his eyes closed, he still saw stars. Once again, she stopped far too soon, an actual whine escaping him before he could clench his teeth. "Now, I'll tell you what I want." She untied both his hands, allowing him to sit up. "I'm going to let you fuck me again and this time I want you to fuck me as hard as you can for as long as you can. Understand?" She didn't hesitate for a moment, but promptly turned around so her back was to him and slammed her weight down. His mind felt like it was made of fire. Instinctively, his hands grabbed her ass and helped to guide her erratic strokes. Soon, he bent his knees and lifted his back to thrust more deeply. Harvey didn't last much longer past that point- his breath was ripped away by the urgency of his release- but his knees held him for several more seconds before he collapsed. He was dully aware of Ruby's weight lifting away and off the bed. Eventually, his breath became calm and he was able to open his eyes to see her at the door, fully dressed. "It's been fun, sweetheart, but I've got places to go and money to earn tonight." She winked and blew him a lipstick-y kiss before opening the door and making to leave. "Wait!" said Harvey desperately, "Aren't you going to untie my feet?" "Hm... nope! Goodbye!" Slam. Maybe he wasn't going to live this down after all. A Bad Boy This story takes place before events described in "Can I Get A Ride? Pts 1 & 2" Author does not condone the use of mind-altering substances for the base pursuit of "getting high". * She had a crush on a boy. She knew that he was probably no good for her. Her mama had warned her about boys like him, attractive in that scruffy way, leather jacket over white tee shirt, cigarette behind his ear, baggy blue jeans. She had been warned, repeatedly, that boys like him would only break her heart, and wouldn't she please just pick a boy who was going to be a doctor or a lawyer or an accountant or some other insufferably boring thing. That was probably why she had such trouble concentrating, when she knew he was sitting right behind her in their Introduction to American Literature class. Their professor was assigning a new book for them to read, and an essay on it due on Monday. Since it was Wednesday, Lauren didn't feel that it was enough time. Professor Crowe dismissed them before she had a chance to complain. The quiet bad boy behind her passed her on his way out, and dropped a folded up sheet of paper on her desk. "Hey, you dropped this," she said. He turned and winked at her and then left the classroom. She opened it up and read it. "Meet me in the bookstore at 4 if you want help with your essay. Peace & Love, Jonny" Lauren flipped open her cell phone to check the time. It was 10:30 in the morning. She still had a few classes to get to before then, but then she would be done at 3. She couldn't concentrate in any of her classes. Instead of taking notes she drew hearts and peace signs, wrote "Jonny and Lauren" in the hearts, doodled and hoped. Three o'clock couldn't come soon enough. She dashed to her dorm room to change out of her hoodie and blue jeans. She wasn't sure why, but for some reason she wanted to wear a short skirt and a tight shirt. Her roommate was gone, so she changed into a very short plaid skirt, that had a flirty bounce to it. She decided that she wanted to look every bit the badass that he was, so she put on her favorite black thong, the one that tied together at the sides, her fishnet stockings and black garter belt. She put on a black push-up bra and a tight white blouse, that buttoned up the front and was simply too small for her, and glimpses of that bra could very easily be seen between the buttons of her blouse. She put on black high heels, and sauntered off to find Jonny. She found him, at four o'clock, in the campus bookstore, looking through a selection of Hemingway novels. "Hey," she said, leaning against the bookshelf. He looked up at her, and she did her best to repress her silly grin when she saw his eyes practically popping out of their sockets at the sight of her. "Hey, Lauren, what's going on?" "I came to get some help on my essay," she said. He pulled a thin book out of the bookshelf. "Old Man and the Sea," he said. "That doesn't look very long." "It'll only take a couple of hours to read it. But we might need all weekend to get our essays right." "I'd love the help." "I'd love to spend the weekend with you," Jonny said. He checked his watch, and then asked, out of the blue, in a quiet, low voice, leaning close to her: "Do you smoke pot?" Lauren blushed and shook her head. Something from the past came back to her: "Just say no." D.A.R.E. classes and some damned annoying cop. She realized she didn't know a thing about pot, just that it was smoked. "Have you ever smoked it?" he asked her, in that same low voice. She had to shake her head again. "Do you want to?" he asked. She looked up at him, into those damned dark eyes, and wondered vaguely if she was making a mistake when she nodded. He put the book back. "I already have a copy at my apartment," he said. "Where's your apartment?" she asked him. "Just off campus. Rosemary Street," he said. They walked through campus together. "What did the time have to do with smoking pot?" she asked him. "Stoner ritual, or something," Jonny said. "According to folklore, four-twenty is always an occasion to smoke some pot." "Huh," she said. They came to the edge of campus and crossed busy College Avenue at a stoplight. Jonny lit his cigarette. He offered her one, but she shook her head "no." He only took a couple of drags before he threw it away in the street. They came to his apartment building and he opened the door, leading her into a hallway. He opened the third door on the left with a key, and Lauren found herself in a small studio apartment. Old rock n roll posters covered the walls and ceiling of the studio apartment. A queen-sized bed sat on the floor in the corner. There was a sofa, in front of a TV with a couple of video game systems. Behind the sofa were two long low bookshelves that were overflowing with books. There was a desk with a computer, but it was turned off. Jonny took a peak at the clock on the wall. 4:15. He sat down on the bed and opened a drawer, pulled out a plastic baggie half full of green leafy nuggets. She sat down on the sofa and watched as he rolled up some of the weed into a joint. It took a few minutes, but then he sat down on the sofa next to her. He raised one end of the joint to his lips, lit the other end with his Bic cigarette lighter, and drew in on the smoke. He handed it to her after he blew out the smoke. She took it and raised it to her lips. "Just breathe in," he said. She did and coughed after holding in the smoke for just a few seconds. She coughed and the smoke rushed from her lungs. "Whoa, that was a big hit, Lauren, don't worry, you'll get the hang of it." Jonny took the joint back and took another hit, then handed it back to her and stood up. He turned on a blacklight near the bed and pulled the blinds on the window, and the room was aglow in neon color. Lauren looked around with bloodshot eyes, realized she had a joint in her hand, and took another hit as Jonny sat down again next to her. Jonny took the joint from her and took a hit. He breathed it out and took another hit and handed it back to Lauren. She was slow to take a hit, but she did, and then found herself wondering what it was she felt on her leg. She handed Jonny the joint and watched as he took it, took a hit, and set the joint down in an ashtray. She saw that it was his hand on her leg. "What about the essay?" she asked. "I need to read that book." "You're not going to be able to remember much of it now," he said. His hand was inching its way up her fishnet stockings, coming dangerously close to the hem of her skirt. She wanted to scoot away from him, his touch was making her nervous, but she found herself scooting closer to him. Her thoughts were lost in the clouds of her mind, and she just went with the flow when Jonny started kissing her neck. "No," she said, "I shouldn't, I have a boyfriend," but her protests were in vain. She leaned into him as he kissed up and down her neck, and she realized that she was incredibly wet between the legs. She wondered for a moment who that pesky boyfriend was, failed to conjure his name in the haze of her mind, and began to fall in love with this pothead Jonny from class. He was pushing her onto her back on the sofa, and he was on top of her. She watched him unbutton his blue jeans and pull them down past his knees. There was a great tent in his boxers, and Lauren realized that her thong was soaked through. He was spreading her legs—and she was letting him—and he lifted her skirt to take a peak at her kitty. "I love your stockings," he said. "We shouldn't be doing this," she protested, meekly, as he reached up her skirt, examining her thong, finding it was only tied together. He deftly untied both sides at once and pulled it away from her. He felt how it was soaked with her juices, and he raised it to his face, smelled her, tasted her, before throwing the thong to the floor. She tried to get away, then. "No," she said, "please, don't, Jonny, I just wanted help with my essay." She tried to sit up but he pushed her back down, hard. He grabbed her shirt in the middle, where it buttons, and pulled the two sides of the shirt apart, hard. Buttons flew across the room and Jonny stared greedily at her exposed chest, the sexy black push-up bra. He grabbed her wrists, one in each hand, and put them over her head. He managed to get both her arms into a hold in one on his hands. She squirmed under him. "Let me go," she said. "Please, Jonny, no, just let me go." He didn't say anything. With his free hand he pulled down his boxers to his knees, and she saw his hard cock, standing erect and ready. His grip on her was too strong. She couldn't get away. She tried to shut her legs but he was already between them. She felt his hot hard cock rubbing against her crotch, searching for that wet entrance. "You dressed like such a slut to meet me," he was saying in her ear. His body was pressed against hers, his cock rubbing against her, the tip of his cockhead finally finding the wet entrance to her. He didn't push it in immediately. She tried to move away from him again, but with his free hand he grabbed her hip and suddenly forced himself deeply into her. She cried out and he put his hand over her mouth. They stared at each other. He started to slowly slide his cock out of her, until just the head was inside. Then, slowly, he slid back into her. "You dressed like you wanted me to fuck you. Isn't that what you wanted?" She tried to speak but his hand was still over her mouth. "Do you want to be my little whore? My little slut?" He slid his cock in and out, still holding her prone beneath him. In and out, his cockhead hitting all the right spots in her pussy with every thrust. "I'll give you all the weed you want if you just fuck me whenever I want, is that what you want? To be my little whore? Is that why you dressed up like a schoolgirl slut?" He was fucking her faster now. She closed her eyes, moaning into his hand. She started bucking her hips against his thrusting, trying to get more of his cock into her. Something primal had taken over in her. He took his hand off her mouth and she moaned louder. "Yes yes yes yes yes," she cried out. She wrapped her fishnet stocking legs around him at his hips, bucking her hips and using her legs to push him deeper inside of her. "Is that what you want you little slut?" he demanded. "To be my whore?" "Yes yes yes yes yes yes," she cried out. She opened her eyes and realized what she had just done, and that it was too late. He let go of her wrists and she wrapped her newly free arms around him, grabbing his ass with one of her hands, his cock filling her pussy. He grabbed her ass then and pulled her up with himself, and then sat down on the sofa, Lauren on top of him, his cock still buried deep in her. He ran his hands up and down her fishnet stocking legs, felt up her skirt, played with her garter belt, felt up her tits, all while she rode him hard. She was bouncing up and down on him on the sofa, his cock hitting her in all the right spots, and then suddenly she was coming. She drove herself hard down onto his cock, dug her fingernails into his back, cried out: "I'm coming Jonny I'm coming!" She bucked her hips with him deep inside her, moving his cock around in her pussy, her pussy squeezing at his cock, pulling at it, trying to get more of his hot, hard, thick cock into her. He squeezed both her tits, hard, and she loved it, and then her intense orgasm began to subside. "Now make me come, you cockslut," Jonny demanded. She knew exactly what to do. Slowly, careful to keep his cock inside her, she turned around, 180 degrees, so that her back was to him. He moved himself closer to the edge of the sofa, so she could get her high-heeled feet on the floor. "I love this view of your tight ass," he said. He grabbed hold of her hips, to help balance her, and started moving her up and down, taking his cock deep into her, and then all the way out to the head. They got into a rhythm. He slapped her ass whenever he wanted her to speed up. Lauren was coming again before she knew it, his cockhead hitting all the right spots every time she went up and every time she went down. "Fuck me hard you slut," Jonny said, and she did. Suddenly, using his grip on her hips, he pulled her hard down on his cock, and held her there. He leaned back and grabbed hold of her tits, pressing her body against his, and he bucked his hips, driving his cock deeper inside her than it had been yet. Then she felt his cock grow inside her, stretching her pussy like it had never been before. He held her tightly. She didn't know anything that big would ever fit inside her. And then his cock exploded inside her. They screamed out in ecstasy as his cock shot streams of his white hot cum deep into her pussy, filling the depths of her kitty. He held her for a moment, hugging her tightly. She kissed his cheek, and then he helped her off him. She sat down next to him on the sofa again, leaned against him. He put his arm around her, and with his other hand grabbed the half-smoked joint from the ashtray. He relit it and took a hit and offered it to her. She took it, idly wondered if she would ever be sober again, and then took a hit. "Now, about that essay," Jonny said. "What essay?" Lauren asked. She took another hit and gave the joint back to Jonny. "The Old Man and the Sea." "Oh, right." He pulled the thin book from the bookcase, opened it to the first page, and began reading it aloud to her. A Bad Boy Pays Up We had things too great. I never knew a more special feeling in my life and now I only know sorry for the loss of that feeling. I let my own insecurities and fears take that from me. How could I deserve such a special person and how could she really love me. Those were the thoughts that lead to the problems we have now. Together we are trying to work through them though only time will heal the pain caused with my hurt and anger. I still struggle with the feelings that she could not love the real me: the real me that no one has ever really loved. No one has ever wanted me unless they were getting something out of me. What a God awful mistake: now that feeling is so broken I doubt that it will ever come back. If she only knew how sorry I was for falling apart and hurting her maybe things would be different maybe they will be again someday. Sometimes it gets so frustrating that everything is just how she wants it with no compromise. What to do about that I don't know. I know I am not allowed to make demands or stand up to her. I just hope that things will improve but she is ok with things are they are or so I thought. How I miss those mornings where I touched her and felt my heart skip a beat and now I touch her and she runs from the bed. Trouble between us started with me being loud and angry. I stood up and that was not allowed. Now I am left with my memories. Now I am being punished for that outburst. I live with my memories of slow passionate love making; memories of heat and sweat and breathless abandon. How I miss those moments but they live in my heart and mind. She surprises me though this morning. She stays and kisses my arm as I stroke her supple breasts. My arms wrapped around her and my body pressed to her I kiss her neck as I stroke her nipples. Silently we both slept in that position: memories of an earlier night play in my mind and I feel my excitement grow. I stoke her softly and feel her start to stir. I kiss her neck down her shoulder: her eyes flutter as her lips part. I kiss them gently. She begins to wake and kiss me back. I take her in my arms and kiss her again and she wraps her arms around me taking my hair in her fisted hand. "You are being a bad boy and playing unfair." She whispers then kisses my arm again. She then kisses me back passionately. 'Morning love.' I say with a deep rasp in my voice. You mumble 'Morning, now slow down boy' and kiss me again. We hug each other kissing deeper and with more heat each time. My lips part and I slide my tongue between her lips and feel meet tongue meet mine. I moan softly as our tongues dance a seductive dance around each other. She then pulls back and looks at me laughing softly. "Is someone horny?" she asked lifting one brow. "I love you." I whisper. "And that means you start this without asking." She says. I know where this is leading and I get more aroused. My hand slides up her side again to her breasts and cups one in the palm. My fingers seek her nipple and tenderly roll it between them. I hear her moan and kiss her lips again, taking her moan within me. I move my hand to the other breast and move my head down to take her nipple into my mouth. My tongue playfully flicks the nipple nestled in my mouth. Her skin tastes like honey as I lick the nipple in a slow concentric motion. I hold her close to me and feel her arch slightly to my body. She moves her hips to mine in a slow steady motion back and forth. "You know what I like." She says. "You better be a good boy and make me happy." I slide my hand down her side and cup her labia in my hand feeling the heat of her on my fingers. I slide my finger to her pussy feeling the wetness. I feel a pulsing in my body as I become harder pressing against her leg. I moan again deeper and louder. I want her so bad but I take my time. My finger slowly moves through her wetness to your clit and strokes it. I feel her shiver in my arms as I again swallow her moan with a slow passionate kiss. My breath comes faster as I kiss her. I kiss you lightly as I stroke her clit and kiss her neck and your chest and then your breasts. I slowly move down her body steadily stroking your clit. She arches towards me and moans knowingly. I kiss her tummy and move to her labia. Her hands move to my head and guide me to her. I hear her moan and move my fingers to her pussy as my tongue parts hers. She pushes her hips to my mouth. My tongue slides over her hot pulsing clit. My tongue begins to move in a slow circular motion around the head, flicking it from time to time as I feel her jump ever so slightly as I do. My fingers move in and out of her pussy as I lick your clit. I take one wet finger and move it to her ass and feel it tighten noticeably. Her hands grab my hair tightly forcing my face against her hot pulsing clit. I move my fingers rhythmically in and out of her putting more pressure on your ass as I do. She relaxes letting my finger in. She pushes her hips to me hungrily. She grows wetter as she cries out pulling my hair in her clenched fists. I suck her clit and feel her shiver again as I take her pussy and ass with my fingers. I know her movements and know she has peaked twice now. She is hard and throbbing under my lips as I suck harder on her clit. She cries out calling my name. I feel her shudder again and pull my hair pulling my face away from her. I am pulsing hard now feeling my cock grow rigid wanting her. Her hands pull me up next to her and she orders me to take her. I turn her and move behind her sliding my cock between her legs stroking her ass and moving to her pussy. I pause there kissing her neck. She moves your hips back to mine and forces me inside of her. I feel her pussy pulse on my cock and begin a slow steady movement in and out letting my shaft stroke her ass as I do. She tightens and loosens on me. I grow harder in her wetness moving the full length in and out of her pussy. I reach around and stroke her clit and she lets out a cry. I feel her tighten on my cock and know she has climaxed again. I move faster now moving my head all the way out and stroke her ass. She begins to move lower and slower forcing my head harder against her ass. I keep teasing her taking her pussy hard and stroking her ass with each thrust. She reaches her arm around and grabs the cheek of my ass and in a low sensual voice she orders me to take it. She moves making it harder not to be in her ass. I tease almost entering but sliding the shaft past it into her pussy again and again. She digs her nails into me and demands that I take it now. I press the head of my cock to her ass. 'Fuck it NOW.' She says as she painfully digs her nails into me. It makes me more excited feeling she claws at me. I thrust into her ass as she pushes back on me at the same moment. I let out at gasp and she cries out as my cock goes deep inside of her. She grabs me harder feeling her nails dig into me. I move with her not coming in or out while she gasps with the pleasure of the pain of final penetration. I start to move in and out thrusting deep and hard. I feel her so tight on my cock. She tightens her ass as I pull out and drive in harder each time. The friction increases as I take your ass faster and faster. My back arches as I drive in hard as I can. Her hand still holds my ass tight digging her nails in. I get unusually aroused feeling that: the pain heightens my arousal. She tightens her ass making it harder and harder to penetrate and she moans with each thrust. I drive in deep and the throbbing begins. I know the end is near. 'Cum baby.' She cries out. I hold it feeling the throbbing increase with each thrust. I start to shake and drive deep exploding deep in her ass. I hold my hips to hers as my body shudders. I push deeper as a second shudder takes over. I cum deep inside her with a gasp: I feel a third shudder take over and hold onto her tightly with a deep moan. I hold her to me neither of us moving. I whisper 'I love you.' I begin to relax next to her. I hold on to her feeling my heart still racing. I kiss her neck telling her again how much I love her. This is how she lets me know the argument is over and this is how we love each other.