16 comments/ 138715 views/ 25 favorites Flirting with Jason By: ~Avalon~ I looked up from my desk as Jason entered my office. I'd been working tirelessly for the past two weeks on a project, rarely even taking a lunch and I was happy for the diversion. Never mind the fact that Jason was pretty damn cute and a nice way to be diverted. "Hey gorgeous," He grinned at me, "I'm going out for drinks with some buddies tonight, wanna come along?" As I considered it, my mind was drawn back to the last time Jason and I had gone out for drinks together. He was so much fun to flirt with, and I really needed to unwind. Jason is always joking around at work. He's boyishly handsome, tall, fit but definitely not a pretty boy. "Sure," I smiled back, "Sounds like fun." We made arrangements for him to pick me up later. Driving home, I once again thought about the last time we went out. We had a purely platonic friendship, but there was definite sexual tension between us. The flirting that night had gotten a bit more intense than usual. It started out playfully, drinking and laughing, discussing our fantasies. I probably revealed a bit too much when I told him that I'd always fantasized about being with two guys, and particularly double penetration. He was surprised and told me that it was nice to see behind my good girl exterior. When he pulled me out to the dance floor, it was raw and primal. He held me so close; I could feel his body responding to me. I was convinced that something more than flirting would happen that night. But, to my disappointment he dropped me off at home with nothing more than a friendly peck on the cheek. I took a long hot bath when I got home; relishing the way the warm water caressed my body. As usual, I let my mind and my hands wander, imagining what might have happened that night, and hoping for what might happen tonight. Running my hands over my body and bringing myself to a short, sharp orgasm. It had been a pretty rough year. My ten year marriage had ended and my kids were growing up too fast. Where ever I went I was starting to feel like a fifth wheel. I was the token single woman in her thirties amongst a sea of happy couples. I had been set up on a few dates that year. I quickly realized long before the end of the date why these men were single. Mostly, they were boring, they either had nothing to say or they seemed far too wrapped up in themselves. I stood, surveying myself in the mirror. I'd never been able to see myself as a whole person, but instead I would always look at and find fault with each individual part. My face, I had always viewed as ordinary, the girl next door. I always wished I was more exotic looking. I yearned to be stunning. For some reason, all I could see then was my medium length, medium brown hair, my small nose, average sized, average shaped eyes. What I didn't see, were the things other people noticed, the pure green of my eyes, standing out against the natural tan of my skin, unmarred by even the slightest hint of hazel, and the fullness of my lips, with their perfect Cupid's bow centre, that actually did give my face the touch of exoticism that I wanted but couldn't see. I had no idea how many men had stroked themselves while they imagined looking into my emerald green eyes, and pushing their throbbing erection between my pouty lips. Jason was, in fact at almost precisely that moment standing in the shower, leaning against the wall, furiously pumping his prick with his hand, imagining the feeling of my mouth. As he spurted his cum all over his hand, he was picturing it landing first on my tongue, and then on my tits. In high school, my friends used to tease me and call me Barbie, because my figure so closely resembled a Barbie doll. After having two children, and the laws of nature taking its toll, I felt less comfortable with how my figure had turned out. While it was true, two pregnancies, and less time for the gym had added a bit of weight, and curves to my frame that were non-existent before, it had also added a lushness and sensuality to my body that hadn't existed before either. At that time, I was only beginning to appreciate my body. My breasts are large for my frame and full, my waist is small, and I've come to love the curve from my waist to my hips. I dressed carefully; wanting to make sure I looked sexy, but not cheap. I do in fact look my best with no clothes at all, or a bra and panties at the very minimum. For some reason with my chest being so much larger than the rest of me, in clothes it gives me a top heavy appearance, without clothes, it works just fine. The mid thigh black skirt, black stockings, black boots, black and blue baby doll top and of course black bra and panties made me achieve the look I was striving for rather well. I gave one final glance in the mirror, at first thinking I looked pretty good, then sighing as I tugged the clip out of my carefully styled hair, shaking out my wavy locks and sticking my tongue out at my reflection. I gave my hair one final toss, giving it a tousled, sexy look and felt more at ease. I sat down and waited, once more allowing my mind to wander to where I hoped this night might lead. Jason arrived exactly on time, the ringing of the doorbell jarring me out of my fantasy. "God Tina," He gulped, "You look amazing." I smiled softly at him as his eyes traveled over my body. "Thanks," I said with a grin, "You're looking pretty good yourself." We made small talk as we drove to the club. I kept noticing happily, that he was focused far more on me, than on the road. We made our way through the crowded club. He held firmly on to my hand as we sought out his friends. Arriving at the table, he introduced me to everyone there, two girls, who paid little attention to me, two guys, who also barely acknowledged my presence seeming far more interested in their dates than anybody new coming to the table, and one other guy who Jason introduced as Matt. While Jason looked like the boy next door, Matt was exotically good looking. He was tall, with a bigger build, not heavy but nobody would ever call him skinny, dark hair, dark skin, dark eyes, he looked like a model. Matt stood up and shifted over in the booth, allowing me to slide in beside him. "So, what's a cute girl like you doing going out with an ugly fucker like him," He laughed. I laughed along with him, "He's not so bad," I said smiling at Jason. "I'm going to get drinks," Jason announced. He then leaned over and whispered in my ear, "Do NOT move, and don't listen to a word he says." With that he wandered off to the bar. The foursome sitting at the table got up to dance, the girls giggling and pulling the guys toward the dance floor. "Yanno," Matt whispered, "Jason said you were beautiful, but beautiful doesn't do you justice." "Thank you," I whispered back and blushed slightly. It's not that I wasn't used to compliments. I usually got my fair share of attention, but back then I usually doubted the sincerity of the compliment. This guy was so incredibly good looking. I imagined that he could have any girl in the place. I looked up as Jason slid in next to me, presenting me with a much needed drink. He knew that when I first started drinking I preferred something that tasted more like juice and less like booze. What he brought me did the trick and I was drinking it down fast. The drinks were soon flowing; the conversation was becoming more playful as we started to unwind. At one point I excused myself to go to the washroom, forgetting my purse and having to lean strategically across the table to retrieve it. I noticed both Matt and Jason looking where my shirt gaped open as I leaned over. They noticed me noticing, and I grinned as I walked away. I got back to the table and once more sat between Jason and Matt. I was really enjoying all of the playful banter and flirting, it was making me feel beautiful and sexy. "Let's go dance," Jason announced, pulling me by the hand toward the dance floor. The music was loud, pounding with bass. I wasn't sure if it was the drinks or the company but I was feeling really good. I became bolder, pressing my body against him while we danced, closing my eyes as his hands slid down over my waist, down to my hips. Out of the corner of my eye I could see Matt approaching the dance floor. I jumped a bit when I felt him come up behind me. Jason pulled back slightly as Matt moved in closer. His hands traveled the same road that Jason's had; resting against my hips, but Matt pulled me gently back against him. He bent forward and whispered in my ear, "You look so fucking hot dancing like that." He pressed the beginnings of a hard on against me, making me moan slightly. I could feel my body starting to react as I pressed back against him, swaying to the music, feeling him grind himself against me. Jason was watching with an amused look on his face. He reached out and grabbed my hands, pulling me out of Matt's grip and announced, "I think it's time go." "Already?" I protested, "I'm having fun." "We can go drink at my place. It's cheaper and I have music." We hopped in a cab, the three of us sitting in the back seat with me between them. Jason had his arm around me, his fingers resting against my neck, touching me lightly and sending little shivers down my spine. Matt had his hand resting against my thigh. It was all I could do not to slide forward so his hand would move up higher. I leaned back and sighed deeply. I was thinking how much fun this night was turning out to be. Once we got to Jason's, he poured drinks and turned the music on. Instead of a hard pounding dance beat like in the club, this was soft, slow jazz. He pulled me against him and we started to dance. Our bodies crushed together. He pulled me in so tight; I could feel him growing hard against me. Jason stepped back slightly and once again, Matt stood behind me, his arms wrapped around me, moving his hips to the beat. Matt's hands slid up, casually brushing his fingertips against my breasts. He slid his hands up and down, each time touching the sides of my breasts, then sliding his fingertips underneath, dancing along the underside of each breast. "God!" I gasped. My knees weakened. "Relax Tina," Matt whispered in my ear, "We're going to make you feel so good." He kissed the back of my neck, sucking it gently as his hands slipped under my top, raising it as he slid his hands up to cup my tits. I was on sensory overload. Every nerve ending seemed to be on high alert. Jason leaned forward and kissed me hard, drawing my tongue into his mouth and sucking it gently making me moan against his lips. He only broke the kiss to watch as Matt pulled the lacy fabric of my bra forward, exposing my soft flesh and my light brown, rock hard nipples. I started to moan as Matt circled each nipple with his fingertips. He had a perfect touch, alternating from barely touching to pinching almost roughly. I could feel Matt's cock pressed against my ass, and I started to press back against it, moving my hips, still attempting to keep up the pretense of dancing. Jason started kissing my neck, licking and sucking his way down to my chest, making a trail of heat with his tongue. Matt's hands dropped back to my sides and Jason cupped my breasts, licking the tops of them and making them shiny with his saliva. I slid my fingers into his hair, arching my back, my entire body aching with need. I reached down and pressed the palm of my hand flat against the front of Jason's jeans, feeling his cock jump against my hand. He traced my nipple with his tongue, then sucked it into his mouth, raking across it with his teeth. All the while I could feel Matt standing behind me, easing my skirt up slowly, his cock becoming harder as I kept pushing back against him, grinding my ass against him. I could almost feel my pussy start to drip with wetness when Jason pushed my tits together and ran his tongue from one nipple to the other. I love that feeling; it's like an electrical current running from my nipples directly to my clit. "That feels so good," I managed to mutter. Matt eased my legs apart with his hands and slipped one strong hand between my legs. He ran his fingertip over my panties along my slit, feeling the puffiness of my pussy lips and the dewy wetness. "Mmmm you're wet," he growled. "Wet?" I thought, I couldn't believe I hadn't cum already. My clit was literally throbbing. All I did was moan weakly as I tried to keep myself calm. Jason stepped back at this point, clearly thinking with nothing but his cock. He unbuttoned and unzipped his pants. I watched breathlessly as he reached inside and gripped his throbbing tool. Matt pushed my panties to one side, and once again ran his fingertip up and down along my pussy. My clit jumped every time his finger moved up, it was agonizing the way he teased it, coming so close and not touching it. He worked one finger slowly inside me, purring into my ear as he did, "Such a sweet, wet, tight little pussy." Jason was slowly stroking his cock, gripping it and releasing. "Suck his cock for him Tina," Matt growled. I quickly dropped down on to my knees and pressed my tongue against the base of Jason's prick, slowly dragging it up to the crown, tracing the ridge with the tip of my tongue before wrapping my wet lips around it and sucking it into my mouth. "Fuck," Jason groaned as he sank down on to the floor, pulling the rest of his clothes off. I watched him with appreciation. His firm toned body was glistening in sweat. He slid his fingers into my hair; closing his eyes and guiding my mouth back down on to his cock. He groaned again as my lips worked their way down, enveloping every inch of him in my mouth, sucking softly then slowly pulling back again. This was an area I felt comfortable in. I was thankful for the short period of time in which to get myself back under control. I looked up at him, clearly seeing the pleasure on his face as he began to move his hips, thrusting himself into my mouth. I was on all fours, leaned over on my elbows, my ass in the air, sucking his cock for all I was worth. Matt had still been standing, watching me suck Jason's cock. He knelt down behind me, and I almost jumped out of my skin when I felt the warmth of his breath against my pussy. He pushed two fingers firmly inside me, and began licking my puffy lips. "Your pussy tastes so fucking good," He whispered. All I could do was moan around Jason's cock. My clit was literally aching for contact. It seemed almost like a beating heart, it was throbbing so much. He seemed to sense it and moved his fingers out of my pussy, and pressed them against my clit. He pushed his tongue inside me, literally fucking me with it, and began to rub my clit. He rubbed it lightly at first, then harder as he sensed my need to cum. I was pushing back, against his fingers and his tongue. My throbbing clit was giving off little sparks of energy. Jason was attempting to hold me still as he thrust into my mouth. "That's it, fuck her mouth." Matt encouraged him. He moved his lips to my clit, sucking it gently, and pushed two fingers back inside me. "Oh God, yes, please suck my clit," I pulled back and moaned as my entire body tensed and I started to cum, writhing and gasping as he sucked and licked my clit, fucking me hard with his fingers. As soon as my climax began to subside, they changed positions. I was still trying to catch my breath as Jason moved behind me. I looked up, watching Matt strip off his clothes. He was incredibly beautiful; his body seemed to ripple with energy. He knelt in front of me. I couldn't stop myself from gasping. His cock was long and thick, and leaking pre cum. He held my head still with one hand, gripping the base of his cock with the other and rubbed it across my lips. He leaned over and kissed me. I could taste the tangy sweetness of my juices on his lips and tongue. He then sat back, looking at me as he slowly stroked his erection. Jason was looking down, seeing me on all fours, my pussy lips exposed and engorged. "Your pussy is so wet," He groaned as he rubbed the tip of his cock against my slit. He had one hand on the small of my back, pushing me firmly down as he rubbed his hardness against me. "God, Jason, fuck me please," I pleaded, pushing backwards against him. I wanted his cock inside me so badly. I don't think there's ever been a time in my life before or since that I've literally needed to get fucked with such intensity. "So fucking tight," He whispered as he pressed his throbbing prick inside me. I groaned deeply as he filled me slowly. My muscles contracting as he sank into me, and once more I was speechless except for deep unintelligible moans. It felt absolutely incredible. "Oh yeah, that feels so good," I groaned. "Open your mouth Tina," Matt commanded, "I'm gonna fuck your pretty mouth while he fucks that pretty pussy." I licked my lips and opened them slightly as he held his cock and fed it into my hungry mouth, stretching it open. Jason started moving his hips slowly, pushing against my g-spot with every thrust, making my body quake. Matt held firmly on to my head and pushed his cock deeply into my mouth. He began moving his hips with the same rhythm as Jason, fucking my mouth. I slid one hand down, alternating between rubbing my aching clit and cupping Jason's balls. I felt another orgasm welling up inside me, and moaned around Matt's cock as I started to cum. Matt pulled back, his eyes closed; he began stroking his cock into my open mouth. I could feel Jason's cock begin to throb inside me, pulsing and jerking, filling me with his cum as he called out, "Fuck, fuck, fuck." I looked up at Matt watching him stroke his prick hard and fast. I begged him softly, "Please cum on my tongue; I want to taste you so badly." I was mesmerized watching the thick ropes of cum erupting from him, seeing his body shudder and shake. He pushed his dick back into my mouth after the first shot hit my tongue. I sucked it greedily, cherishing the musky, salty taste before swallowing every drop. We all lay back, exhausted, basking in the afterglow of incredible sex. I lay between them and lazily explored their bodies with my hands. Reaching down I pressed the palm of my hand against Jason's softened tool. I grinned at him as I felt it hardening against my hand. I slid down between his legs, slowly licking his cock and savoring the taste of our intermingled juices. I wrapped my lips around him, feeling it growing fully inside my mouth. "Such a good little cocksucker," he croaked. Matt sank his fingers into my hair and pulled me up to kiss him, his hot tongue exploring the inside of my mouth. "Get on top of him," He murmured against my lips, "I wanna watch you fuck him." I straddled Jason's now fully erect prick, rubbing my aching pussy against it. He slid one hand around my waist the other holding his cock, aiming it straight up. He guided me up and then pulled me down roughly onto it. We both moaned deeply. I tried to move slowly, grinding my clit against him with every stroke. Cupping my tits and pinching my nipples. Little electric sparks ran through me every time I pushed down against him. His hands moved down further, grabbing my ass and guiding me up and down, harder and faster. Matt moved behind me and I moaned loudly as he ran the tip of one finger up and down the crack of my ass. I felt his tongue grazing one thigh then the other. I closed my eyes, and groaned as his tongue moved to the crack of my ass, slowly licking up and down. Jason held me down, completely still against him, while I tried to push back against Matt's tongue. "Mmmm," He moaned, "What do you want Tina?" "Please," I gasped. "Please what?" I could hear the teasing tone in his voice. "Please tongue my asshole," I begged. Jason held my ass cheeks wide and kept me completely still, his cock buried firmly inside me as Matt began lapping at my rosebud. There is something about this particular act that I love. There is an amazing intimacy about oral sex, but having my asshole licked has an every greater intimacy. That combined with the forbidden, almost dirtiness of the act makes my head spin. I love getting it and I love giving it when the guy allows me to. Flirting with Jason Ch. 02 It was Thursday evening. I had just changed into to my pajamas and was settling down to watch "Friends", when the phone rang. "Whatcha doing?" A deep voice spoke from the other end of the phone. "Hi Matt," I felt a lurch in my stomach. This was definitely a rare occurrence. In the eight or so months since Matt, Jason and I had been playing together, I think this may have only been the second or third time Matt had ever called me. "I was just watching tv, what about you?" I tried to keep my voice light. "I'm watching porn," He laughed a bit, "Let's go out." "Is it good porn?" I asked, "And... you could just come over here if you want." "It's not bad," He responded, "I don't wanna come over, I wanna go out. I'll come by and get you in an hour." "Okay," I replied, "Where do you wanna go?" "I have a place in mind," He said, "And Tina?" "Yeah?" I said weakly. "I want you to do something for me," His voice was low and husky. "Okay," I tried to keep the tremble out of my voice, "What is it?" "Wear that black shirt, the sheer one," He stated. I immediately knew which one he was talking about. He and Jason had both been very appreciative of it the last time I wore it. "Wear a skirt, something loose, stockings, and your sheer black bra and panties." "Ummm," I pictured that particular top with my sheer black bra underneath it. My nipples would be completely visible. "You want me to wear THAT in public?" "Okay," I could hear the grin in his voice, "You can wear your black sweater over it, the one with the buttons." "And do you have any preference in my shoes?" I tried to make my tone sound teasing. "No," He laughed, "But wear something with a heel. I'll see you in an hour." "God," I thought as I hung up the phone. There is something about Matt which always leaves me feeling unsettled. I was a bit surprised that he even noticed anything about my wardrobe, especially enough to have a preference in what I should wear. Matt, Jason and I had gotten together quite a few times over the last while. It was amusing to me that we always kept up the pretense of going somewhere, rather than just getting together to fuck. A few times Jason and I had gone out alone, still with the same ending result. When Jason would call me to ask me to go out, I always hated the pleading sound in my voice when I would ask if Matt was coming. I really did enjoy spending time with Jason. He was sweet and romantic. Everything about him and everything he did, had an air of lightness and good humor to it. Matt on the other hand, it didn't matter what he said, he could be asking the time and it sounded dirty. After my shower, I started to get dressed. I was overcome with a shiver of nervous anticipation. Matt and I had never gone out alone together. I took a deep breath and kept dressing, trying to push the feeling away. Standing in front of the mirror, I was thankful that I would be wearing the sweater over my top. It really was a pretty blouse. It had a high neck, with buttons all the way down, it clung to my breasts and was very flattering. It was also very see through. With my black sheer bra underneath, my nipples were clearly visible. I pulled my sweater on, and fastened one button at my waist. The effect was perfect. My cleavage was highlighted nicely, covered only in the filmy fabric. I chose a short, black flirty skirt. It was fun and playful with a ruffle at the hem. I wore very little makeup, just a touch of pink and brown eye shadow, a sweep of mascara and dark lipstick. I let my hair dry naturally, not trying to tame the waves like I usually do. I pulled the front pieces back with a clip, smiling at my reflection. I sat down and waited, completely unsure what this night would bring. I knew that when the three of us went out, the night would always end in sex. With Matt alone, I wasn't as sure. He arrived about half an hour later then he'd said he would. For some reason with Matt it seemed expected that he would be late. I'm a compulsively early person. I feel like my entire life is run by clocks. I worry constantly about what time it is, although strangely I don't own a watch. I opened the door when he rung the bell. His eyes swept over me slowly and he said, "Very nice." "Thanks," I answered. Driving to the club, I plunged in to my usual attempt to lighten any situation and tried to engage him in the most ridiculous conversations. I hated listening to my own blathering and seemed unable to stop. When we pulled into the parking lot, I let out a sigh of relief, and quietly muttered, "Thank God." He laughed a bit and got out of the car. He led me to a booth. I sat down while he went to get drinks. It was still fairly early, not quite ten o'clock yet and the club was just starting to fill with people. It really was a fairly seedy place. Although I liked that it wasn't filled with twenty year olds. Most of the clientele seemed to be in their thirties and forties. He arrived back at the table, and I laughed when I saw the drinks he was carrying. Jason would always know to start me off drinking slowly. I really don't handle my booze very well, and I get tipsy pretty quickly. Also, until I'm tipsy, everything but fruity concoctions taste terrible to me. Matt had a tray with two shots of what I assumed was tequila, since he also had lemons slices and a salt shaker. He also had two mixed drinks, which after a sip, I realized was rum and coke. I drank my drink down quickly, and Matt announced it was time for the tequila. He had his beautiful dark eyes on mine as he pushed the sleeve of my sweater up. He held my arm and leaned forward licking about two inches above my wrist. He grinned when I gasped a bit, and liberally applied the salt to the spot where he had licked me. He took his time licking the salt off my arm, quickly shot back the tequila and sucked the juice from the lemon slice. It was incredibly sensual. He kissed me very lightly, his lips really only grazing my own. Then he handed me the salt shaker. "Your turn," He grinned at me. I wanted to make sure I did this right. I moved a bit closer to him, and pulled the neck of his t-shirt to the side, pressing my tongue against his exposed skin. I felt him shiver a bit and smiled, pleased with myself. I shook some salt on the glistening wet patch of skin, and swirled my tongue against it once more. I took a deep breath, downed the tequila and sucked the lemon into my mouth. I winced a bit at the taste; it reminded me of the way turpentine smelled. "Good girl," He whispered, "I'll be right back." He returned a few minutes later with more drinks, no more tequila though thankfully. The little bit of alcohol had taken the edge off my nervousness. I felt bold enough to ask him what kind of porn he had been watching. "Nothing out of the ordinary," He shrugged, "But it was good enough to make my dick hard." Hearing him say that made me shiver again. "Oh," I said softly, "So that's why you called me." He laughed and said, "Well, I was sitting there with my cock in my hand and I thought, why waste this when I could be fucking Tina's tight little pussy." I looked down and bit on the side of my bottom lip. He slid his hand under my chin, tilting my neck up to look at him and said very softly, "Take your sweater off Tina." I started to protest, "But...." He cut me off with a finger to my lips and said, "Shhhh, just do it, you trust me don't you?" I nodded weakly and undid the button on my sweater. He smiled as I shrugged it off my shoulders, his eyes glued to my chest. "It's a little cold in here," I managed to croak. "No, it's not." He slid a bit closer to me, his thigh touching mine and lifted his hand, grazing my nipple with his thumb. He kept his eyes locked on mine, and continued lightly running his thumb over my nipple, almost scratching it. It was agonizing. Everything about this guy screamed sex, it drove me crazy. "You're getting wet aren't you?" His voice was husky. "Yes," I whispered. He took his hand away and moved it to my lips, pushing his index finger into my mouth. I sucked it softly, moaning a bit around it. He pulled his finger from my lips and moved his hand back to my breast, touching my protruding nipple with his wet finger. I shivered uncontrollably. "God to the washroom right now and take your panties off." He commanded. "Oh God, Matt...." I started to protest and he once again cut me off with a finger to my lips. "Go on," He said firmly. I slid out of the booth and made my way shakily to the washroom. I was only barely aware of the men I passed, staring at my nipples, prominently on display through the filmy fabric of my shirt and bra. I tried to clear my head, but I couldn't seem to. It was strange how much I wanted to please this guy and stranger still as I realized that I wanted to do this. I slid back into the booth. He looked at me expectantly. "Did you?" He asked. I nodded slowly, "Uh huh." He slid his hand along my thigh to the hem of my skirt, inching it up slowly, his fingertips heating my flesh as they moved up. He worked my skirt up until the bare flesh of my thighs was showing from the tops of my stockings. I was starting to breathe hard. He kept his eyes locked on mine and slipped his hand between my thighs, sliding them apart. He ran his finger just above the top of my stocking, creating a line of heat along my bare flesh. His fingertips moved up with agonizing slowness. It seemed like this was going on for so long, when he finally touched one fingertip to my pussy lips. I groaned deeply. "I like how you follow instructions," His voice sounded thick, and raspy. He slid his fingertip up and down my slit, making me shake with desire. I looked around nervously, wondering if anybody in the crowded club was able to tell that I was having my bare pussy touched right under the table. My clit was throbbing, my pussy leaking juices. "I love how hot and ready your cunt is," He pulled his finger away, and pushed it back into my mouth. I wrapped my lips around it, greedily sucking my juices from it. "Sit forward in your seat," He demanded firmly. I scooted forward a bit, my ass right on the edge of my seat. He slipped his hand back under my skirt, and pushed his finger firmly into my sopping wet pussy. "Oh God," I couldn't help crying out. My pussy contracted around his finger. "I wonder if anybody walking by realizes that I'm fingering you right now," He stated calmly as he worked his finger in and out of my tight hole. "Matt...God," I started to rock my hips slowly, groaning every time he pulled his fingers back, curling them so they dragged along my g-spot. "Are you gonna cum for me baby?" He leaned forward and kissed me before I had a chance to answer, drawing my tongue between his lips and sucking it softly. I moaned into his mouth. I started to shake as his thumb pressed against my clit, rubbing it firmly as he fingered me faster, the wet squelching noise only adding to my desire. My pussy was throbbing, my clit pulsing. I started to cum, his lips on mine keeping me from crying out. My entire body shook and my pussy clenched his fingers as he pushed them harder inside me. When the wave subsided, he slid his fingers out of me. He brought his hand up to his mouth and licked each finger slowly. "You have such a sweet tasting pussy," He groaned. He stood up and took my hand, "C'mon." "Are we leaving?" I tried not to sound as excited as I felt by the idea of leaving. "Not yet," He grinned, "We're going to the dance floor." The club was now packed with people. All I really wanted to do was leave, take Matt home and fuck him senseless. He led me to a less crowded corner and pulled me into his arms. He turned me so my back was to the wall as we danced. He pressed up against me, grinning as I pushed myself against him. He had his hands on my ass, squeezing it. He led me further into the corner, my back a foot or so from the wall. I felt his hands start to gather the material at the back of my skirt, working it up. He slid his hands under my skirt, kneading the cheeks of my bare ass as we danced. He dropped the material of my skirt, and moved his hands to my face. He kissed me lightly, tracing my lips with the tip of his tongue, before pushing it into my mouth. I murmured against his lips and sucked softly on his tongue. God, he was a great kisser. His kisses were incredibly sensual and full of desire. He broke the kiss and moved behind me. He wrapped his arms around me and pulled me back against him. I started to move my hips, pressing back against him and grinding myself against his cock. "I love your little ass," He whispered. Once more I felt the material of my skirt moving up my thighs. "Oh God, Matt..." I seemed to be saying that a lot tonight. I shivered slightly, as he pressed against me once more. "Do you know how hot you are Tina? How sweet your pussy tastes, how good it feels when it milks my cock? How much I love fucking your tight little ass?" He kept whispering to me. My pussy was throbbing again and leaking juices down my thighs. I loved listening to his voice; everything he said made me shake. I swallowed hard and whispered back, "I love the way your cock feels inside me, I love it when you fill me with your cum." I heard him groan and felt his cock throb against me. I reached behind me and tried to maneuver the button on his jeans. "Mmm," He groaned, "You want my hard cock don't you?" "Yes," I whispered, and continued working on his jeans. He pushed his finger into my mouth, and I groaned as he slipped it between the cheeks of my ass. He slid it up and down, making me push back and moan. Every time his finger passed over the pucker of my asshole, I could feel it open reflexively, wanting him. He rested his back against the wall, and pulled me back firmly against him, his prick nestling in the crack of my ass. I was only vaguely aware of the people around us. All I seemed to be able to concentrate on was how much I wanted him to fuck me. He moved my hair off of my neck, and began licking, kissing and sucking it. Little shivers danced down my spine. "I bet," He whispered in my ear, "That you'd let me fuck your ass, right here and now, wouldn't you?" He sucked my earlobe into his mouth. "Yes!" I said, no longer whispering and not really caring who heard what, "I want you to fuck me so badly Matt." He was moving his hips, his cock gliding between the cheeks of my ass. His breathing was shallow and rapid. His hands were gripping my hips, moving me with him. "Such a dirty little slut," His voice was thick and hoarse. "God, Matt fuck me please," I begged him. This all seemed so insane. Here I was with my skirt pulled up in the back in a crowded club and the sexiest guy I've ever known had his cock between my ass cheeks. My pussy was dripping juices down my thighs. It was nuts and it was the hottest moment of my entire life. The truth was, he could have told me to suck his cock right then and I would have gladly done it, and not cared for a second who was watching. I felt him pull back and turned to see him doing his pants back up. "C'mon," He said, grabbing my hand and pulling me towards the door. "We're going?" I asked. "Yeah," He responded. We walked out of the club and through the parking lot, quickly toward his car. He'd parked on an end of the lot. We got to his car and as I reached for the door handle he stopped me, turning me around and kissing me roughly. His hands moved to my tits, cupping them and squeezing them, his thumbs flicking my nipples. "I love your tits," He groaned, bending and sucking one of my nipples through the fabric. I reached down and started to rub his cock through his jeans. His hands dropped and he quickly unbuttoned and unzipped his pants, reaching in and pulling out his thick prick. I curled my hand around the base, squeezing it gently. "I love your cock, I love the way it feels, I love the way it tastes." I moaned. He pulled me around the back of his car, placing his hands on my shoulders and pushing down gently. "Suck it," His voice was husky and demanding. I dropped down onto my knees, grateful for the grass that surrounded the parking lot. I held his cock in my hand, squeezing it gently once again. I watched a little bead of precum form on the head of his cock and pressed my tongue against it. I whispered, "Matt, you taste so good." I wrapped my lips around the thick head, slowly sucking; working my wet lips down till every inch of him was buried inside my mouth. "That's it Tina," He groaned, "Suck it good." I loved listening to his voice while I licked and sucked him. "Lift up your skirt," He said, "I wanna watch you finger your pussy while you suck my cock." I gathered my skirt around my waist and began rubbing my clit hard and fast. "Spread your legs and fuck yourself with your fingers." I pushed two fingers firmly into my soaking wet pussy, frantically rubbing my clit with my thumb. He moved his hands to my face, holding me still while he thrust his cock into my mouth. "Fuck your little cunt Tina, make yourself cum," Hearing his voice made my clit throb and ache deliciously. I was moving my hips up and down, riding my fingers. I started to feel that spreading warmth of impending orgasm move its way through my body. "Take your shirt and bra off, I wanna cum on your tits." He hissed. I sat back and stripped off my shirt quickly, tossing it to the side. He laughed as I struggled with the clasp on the back of my bra. I was breathing rapidly, my hands were shaking. "Would you help me please?" I surprised to hear how shaky my voice sounded. He grinned at me and moved behind me, undoing the clasp on my bra and sliding his hands forward, underneath the fabric to cup my tits. He walked back around, in front of me and watched as I struggled to take it off the rest of the way. I was dimly aware of the noises in the parking lot, cars starting and people's conversations. He was slowly stroking his cock, with that smirk he gets on his face when he knows that I'm unsure of something. "Do you care that someone might see you Tina?" His voice was slightly louder than a whisper. "Anybody that sees are only gonna be thinking how hot you are, and how good you look with my dick in your mouth." God, his voice, I swear he could make me do anything just by saying it. He slipped one hand back into my hair, holding the base of his cock in his hand and rubbing the fat head across my lips. I opened my mouth, looking up at him as he pushed it between my lips with a grunt. "Your mouth is so hot," He groaned. "Rub your pussy Tina, finger it good for me." I slipped my hand back down, pushing my fingers against my clit before pressing them back inside my soaked hole. I no longer cared about the sounds of the cars starting or the drunken voices of people making their way home. He reached down and roughly grabbed one of my breasts, pinching my nipple. I jumped and gasped and thrust my fingers harder inside my pussy. Once more I felt my orgasm spreading through me. I was moaning around his cock, my fingers moving furiously. He pulled back, stroking his dick hard and fast. "Oh God, Matt, please cum on my tits, cover me with your cum," I pleaded as I started to cum. "Fuck," He moaned loudly as the first shot erupted from the head of his cock. I pushed my tits together, holding them up for his bath of cum. He made me want to be dirty. He made me want to do everything I'd ever fantasized about. The car next to the one beside us, started up, bathing us in soft light as its headlights turned on. Somehow that added something to the situation. I looked up at him, and cupped one of my cum soaked tits in my hand. "I love the way you taste," I whispered and lowered my head, raising my breast with my hand and licked his cum from it. Flirting with Jason Ch. 02 "God, Tina, that's so fucking hot." He began stroking his cock again, coaxing it back to its full girth. He grabbed my wrists and pulled me up so I was standing. He kissed me hard and spun me around. He pushed firmly on my shoulders so that I was leaning over the trunk of his car. I heard the car pull out and was ridiculously disappointed. He pulled up the back of my skirt again, and knelt down. I moaned as he licked from the lacy top of my stockings to the edge of my pussy and back down the other thigh. "Matt, lick my pussy... please," I gasped, unable to stand his teasing. He ran his finger up and down my wet slit. "You want my tongue Tina?" He opened my pussy lips with his thumbs. "God, yes.. please. Fuck me with your tongue," I pressed back, aching for contact. He flicked the tip of his tongue against my exposed clit, causing my entire body to spasm in reflex. He was holding me wide open, completely exposed to him. "Such a pretty pussy," He whispered and pressed his tongue inside me. His fingertip was flicking against my clit as he pushed his tongue in and out of me. "Yes, yes.. Oh God.... That feels so fucking good," I gasped and began thrusting my hips creating more friction on my clit against his finger. "That's it baby, cum on my tongue," He panted. "Fuck, Yes... Oh God, Matt.. Yes," I called out loudly as I started to cum, rocking my hips hard, grinding my clit against his finger. He sucked and licked and rubbed as I poured my juices on his tongue. While my pussy was still contracting, he stood up and pushed his rock hard cock firmly inside me. "So hot and wet," He groaned and thrust his hips. "Fuck me hard, Matt, please," I gasped and tried to push back against him. "I love how tight and wet your little pussy is," He said and thrust harder into me. He slid one finger down and pressed it against my asshole. "Oh God, yes," I groaned. I couldn't get enough of this guy. He knew exactly how to rock his hips to make his cock grind against my g-spot. Every movement sent shocks through my body. "I'm gonna make my cock nice and wet, and then I'm gonna fuck your sweet little asshole," He said. "Yes.. please, fuck my ass," I gasped, wanting it so badly. I started to shake as he pulled out, arching my back for what was coming. He spread my ass cheeks open with one hand, and pressed his wet fat cock head against my puckered asshole. "You love getting your ass fucked don't you?" He growled and pressed the head of his prick inside me. "God.. yes," I groaned, "I love it.. I love the way you fuck my ass." He moved slowly, inch by delicious inch. I closed my eyes and bit my bottom lip. The searing pain that ripped through me only enhanced the currents of electric pleasure that washed over me. He held me completely still against him. His cock firmly buried inside me. We both moaned at the same time as he started rocking his hips lightly. "Rub your clit and finger your cunt Tina," He said loudly. The words were barely out of his mouth and I had two fingers plunged into my pussy, my thumb grinding against my clit. I could feel his cock against my fingers. "Do you want it harder?" He said. His voice was so husky and thick. "Yes...please," I begged, "Fuck my ass hard," He started thrusting hard and fast. My fingers were moving furiously inside me, trying to keep up with him. "Cum in my ass.. please Matt," I groaned. I wanted his cum so badly. I wanted to feel his hard prick throbbing inside me, filling me with his cum. "You're so dirty, such a good little slut," He said. He was fucking me so hard it almost brought tears to my eyes. I started to cum again. It was his voice. He knew exactly what to say to me to make me cum. "Fuck .. yes, Oh God, it's so good," I cried out loudly as I started to cum. "That's it Tina," He growled and thrust hard one last time, "Fuck...Unh." He started to cum. I could feel it pouring inside me, heating my insides. He wrapped his arms around me and pulled me up against him, his cock slipping out of me. He turned me around and kissed me once, roughly on the lips, making me ache for more. "I guess I should get you home," He said. "Ummm, yeah I guess so," I replied. He grabbed my shirt from the grass while I struggled into my bra. He held it out for me, grinning while I put it back on. "Shit," I spat out, "I left my sweater inside." "Oh, so go get it," He said. "Forget it," I said. It occurred to me as I got in the car that Jason would have rushed in to retrieve my forgotten sweater for me. But, while Jason was sweet and fun, it was Matt that I couldn't seem to do without. If it wasn't for Matt, I probably would have stopped playing with Jason a long time back. "How did I let you convince me to do this?" I mused, more to myself than to him. "Do what?" He gave me a questioning look as he backed out of the parking space. "Take me out, buy me a couple drinks then fuck my ass in the parking lot," I couldn't help but laugh at myself. "Cuz," He grinned at me, "You love it." It was true, I did love it. Matt was exciting. He was intense. One look from him, one word out of his mouth and my pussy was dripping wet. He dropped me off with a quick kiss and a soft goodbye. No promises to call me, no "see ya later." It infuriated me that he was so aloof, and infuriated me more that I was so hooked on him. Flirting with Jason "You like that Tina?" He whispered. "It feels so fucking good." I groaned in reply, almost in tears with the barrage of sensations. He seemed to turn his tongue into a dart and pressed it inside me. It was the most incredibly sensation, being probed with his warm, wet tongue. He pulled back slightly, running his fingers along my pussy lips spreading my juices onto my asshole and pushed one wet finger firmly inside me. He began moving it slowly as Jason once again began thrusting up inside me. He added a second finger, letting me catch my breath as he pressed it inside me. He moved his fingers in and out of my asshole in perfect time to Jason's cock in my pussy. I have this thing with anal sex. Almost an obsession I guess. It is one of the most amazing feelings. The pain somehow heightens the pleasure of it. My ex and I had indulged in it occasionally, sometimes I would fuck myself with a vibrator while he fucked my ass, although he could rarely last long feeling the vibrations along with me. Right then, I desperately wanted my ass fucked. I'd fantasized about this for a long time. "Oh God. Yes. Please," I murmured softly. "Ask me," The teasing tone had returned to his voice. He pulled his fingers out of me and began rubbing my asshole with the head of his precum soaked cock. "Oh God, Matt, please fuck my ass," My voice was thick with desire. I was literally shaking with need. Jason held me completely still, and with aching slowness Matt pressed the tip of his cock inside me. I tried to control my breathing, slowly and steadily, knowing the pain would be short lived. I could feel myself opening up to him. He pulled back slightly and then pressed in further, the searing pain mixing in with the pleasure. I don't know quite how to explain that feeling of being completely at someone's mercy. I know that some people don't like it, but it's a feeling that I love. He was clearly experienced with this. He took his time, despite my trying to press back and get him further inside me. He worked his cock into my asshole with deliberate slowness. Every tiny bit making me want more. All I could do was moan and beg, pleading him. "Such a good little slut," He whispered. And then, he was buried completely inside me. We all stayed still, allowing my body to become accustomed to the barrage of sensations. It was like time stood still, I had wanted this for such a long time. Jason broke the stillness first and pulled me down pushing his tongue into my mouth while he began to thrust up inside me. Matt began to move his hips, his cock moving slowly in and out of my asshole. He ended each thrust with a hard push that sent waves of pleasure through me. I've never felt anything so incredible. Normally, I'm pretty noisy when I'm fucking. I like to let the person know how much I'm enjoying it. And, for some reason hearing dirty words coming out of my own mouth, heightens my pleasure. But, at this moment, I was struck almost speechless. Managing little more then to murmur, "Yes, yes," and occasionally, "Oh God." Matt was moving faster, his hands on my cheeks, holding me open and fucking my ass hard. I felt completely full, dirty, slutty and incredibly sexy. Jason slid one hand down between us, and pressed his finger against my swollen clit. I immediately started to explode in orgasm. "Oh God, fuck me harder, please," I begged as I started to cum. Jason was first, his cock responding to the spasmic contractions of my cunt. He started to erupt inside me. "Ugh, oh God, yeah, fuck," He groaned along with a string of other mostly inaudible words. Matt was almost immediately after. He thrust hard twice more and poured his cum deep into my bowels. I could feel every jerk, throb and pulse of his cock deep within me. Matt pulled away, laying on his side and easing me off of Jason. I could hardly catch my breath. He held me close whispering to me, telling me how hot that was, and how beautiful it was. We lay there for a few minutes before I decided I better get myself into the shower. I kissed them both lightly on the lips and headed off to the bathroom. Standing under the water the first thing I noticed was how much my knees stung when the hot water hit them. They were rug burned, and badly. I didn't notice that at all when it was happening, but I guess spending that long on my knees on a rug, it was inevitable. My entire body felt sore, and used, but amazing all at the same time. I was dripping cum from both my pussy and asshole. I stood under the water for what felt like hours. As soon as the water started to cool, I got out. I walked back into the living room. Matt was sound asleep on one couch and Jason was lying on the other with a big grin on his face. "Thank you," I whispered and leaned over to kiss him lightly. "God Tina, that was amazing. You were amazing," He whispered back. I started fumbling around for my clothes, feeling just a bit self conscious in only a towel. "I guess I better get going," I said. "You could stay," He replied grinning. "We could leave him sleeping on the couch and my bed is big enough for the two of us." "As tempting an offer as that is, I think I better go," I said. He called me a cab, feeling badly that he'd left his car at the club. But, it was probably better that way. It would have been such a strange drive home. Already I was thinking about Monday morning at work, if things would be weird between us. When the cab arrived, he was a total gentleman, holding the door open for me, and paying the driver. He kissed me very lightly goodbye and stood watching while the cab pulled away. Monday morning, I tried really hard not to blush when he passed by my office. Things were a bit odd at first, but turned back to normal pretty quickly. We returned to our relationship of laughing and joking, teasing and flirting. We had a few more nights out, a couple of times it was just me and Jason, a few times it was the three of us, another time it was the three of us and a female friend of theirs. I think I managed to actually surprise them a bit more than usual that time.