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.