Flirting with Jason

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.