Flirting with Jason Ch. 02

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She spends a night alone with Matt.
4.8k words
4.67
83k
19

Part 2 of the 2 part series

Updated 09/22/2022
Created 01/18/2007
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~Avalon~
~Avalon~
27 Followers

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.

~Avalon~
~Avalon~
27 Followers
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