Shots Straight Up, Or With A Twist?

It was my turn to smile as I pulled her hips back while thrusting forward, sinking even deeper than I had before in one hard thrust. "Fuck, yes!" Jessi cried as I took over the pace now, pumping my cock in and out of her as she worked her hips in circles each time I pushed deep. Her head had sunk down some, resting on her forearm as she continued to look back at me lustfully, her body shaking with each hard stroke into her cunt. I could see her juices glistening on my shaft, hear the wet sounds as our bodies slapped together, and felt her stiffen and press into me even more when I reached my hand around to stroke and rub her clit while fucking harder. We continued to tease and praise each other with our words as well, Jessi saying "I love how your cock feels in me, fuck me harder, oh yes that's it baby fuck me deep!" while I responded with "Your pussy feels so good, you're fucking soaked girl, fuck I love it," and the like between gasps of pleasure. Jessi did surprise me with her next words, looking into my eyes as she said "I loved it when you tongued my ass, it was so hot. Did you like rimming me you fucker?" at the same time she reached back with one wet finger and began teasing and circling the same hole as I stared. She continued to barely penetrate herself as she continued looking back, and I couldn't help but slow my pace and try to focus as I processed this new act. "MMmm that feels good, do you like it lover?" she half-whispered as I watched her forefinger sink deeper into that back hole, grinding slightly as she writhed under me, "Don't stop fucking me baby, please!" Re-centered on the moment I started to push in and out again, not quite as fast as before as I watched and felt the change in sensations as she became more aroused and uninhibited by the moment. Her finger moved in time with my cock as her mouth lay half-open, both of us lost in the moment as we moved further. "I... I want you to fuck me there. Please." Jessica muttered after one particularly deep thrust, sinking her finger to the base at the same time and holding it there.

I'd only had anal sex a couple of times before, and never in this relationship. It wasn't anything Jessica and I had discussed before, and from the way she was asking I could tell she was waiting for my reaction as to whether I would think this was too strange or not. But all I could think of was how sexy and incredible this woman was, how turned on I was for her, and how ready I was to try this new, intimate act. Seeing that she was still waiting for my reaction I leaned down over her and wrapped one hand around her, holding tight as I kissed the back of her neck. At the same time I withdrew my aching cock from her pussy, easing it slowly up towards her asshole. I felt her hand move free as well, taking hold of my shaft as she lined things up. "Go slow," she whispered, "Just til I get used to it."

With that she started slowly pushing back onto me, while in turn I gently eased forward, feeling the tight ring resisting the head of my cock at first, then seeming to open with a pop as I started to enter. We both paused for a moment as she gasped and bit her lower lip; Jessi adjusting to the penetration of her ass while I was doing my best to hold back at the incredible tight heat surrounding my prick. After a few breaths I felt her relax some and I sank a little deeper. "Mmm yes, more baby," she said, and I leaned back up taking hold of her hips once more as I worked my cock slowly into her amazing ass. From this vantage point I could see the way her cinnamon puckered hole was stretched around my hardness, the arch in her back, and the still-glistening juices on her mound and thighs below - far better than any porn I had ever watched. Fortunately her pussy had been wet enough, particularly when combined with my rim-job earlier, to give us enough lube to keep going with this. By now I was over halfway in, and Jessi suddenly shoved back taking me to the base as she seemed to find that magical point, crying and moaning in one breath as I filled her. The feeling of her clenching down on me was beyond words, like some perfectly molded velvet glove massaging me with every breath. "OK, now do it. Fuck me up the ass, right now," that sultry smile once again as she looked back at me watching my body move.

With those words I slowly pulled back, and eased forward again; my thrusts moving just a bit faster and smoother with every stroke as we both adjusted. I couldn't believe it, I'd gone from just making out with my girlfriend at a party, to a hot sex session in the back of my truck where anyone could see. Before long I was fucking her ass almost as deep as I had her pussy, letting my cock work in and out as I watched every stroke in lust and awe. It was clear that Jessica was enjoying the new act as well, her moans and dirty talk continuing as I took her ass, with her right hand reaching beneath and obviously rubbing her clit fast and hard as she pushed back to meet my thrusts.

Remembering her teasing me just a short time ago I was suddenly inspired, and once more picked up that evil bottle of Jack which had started this whole adventure. Jessi jumped as I dribbled it once more on her body, running down the crack of her ass and around the juncture of my cock and her hole, then continuing to mix with the juices below leaking from her sweet pussy. "You fucker!" she laughed, moaning as the liquid mixed with what we were doing, and giving her a bit of a burn I'm sure as it worked around my cock - but it only seemed to encourage her more as she shoved her hips back harder to meet me. But yet again, Jessi surprised me as she took the bottle from my hand once more. Pushing back as she held onto me, keeping my cock buried to the base in her tight hole, she took a quick hit from the bottle then winked at me and said "Watch this then you kinky bastard." With that she reached down between her legs with the bottle and worked the neck slowly into her pussy while still grinding against my dick in her rear. "Oh yes, so fucking dirty! Now do it again baby!" she moaned as she began to fuck one hole with the glass bottle in time with my now shorter and faster strokes of hard flesh in the other.

This was fucking amazing - not just the kinky image below me as we moved together; but also in the way I could feel the bottle working through the thin layers of skin between us, the way it made her asshole seem to tighten down even more around my penetrating shaft, the wet sounds of both openings being fucked and her loud moans each time she sank the bottle deep enough to rub her clit. An hour ago I never would have imagined a scene like this outside of some movie, now here I was living it on a summer's night with the sexiest girl I'd ever been with. Jessica was obviously into it as well, her own moans and dirty talk coming faster and hotter and rougher as we proceeded. "Fuck my ass. Use me. Oh fuck that feels so good. I'm fucking wet. God I love your dick in me. Do you like how fucking dirty I am? Keep fucking me harder," is the barest sample of the words she said, each moment, each thought just encouraging me to enjoy this more and more.

I'd love to tell some story about how this went on for hours, each moment even hotter and sexier than the last - but the truth is, it's a miracle I lasted even this long. After only a few more strokes I could feel the point of no return approaching, and as I suddenly watched her almost collapse and cry out loudly (no hiding what was going on now!), her ass and cunt clenching down as one as she came even harder than before, it was enough to push me over the edge. With Jessica still obviously in the midst of orgasm I sank my cock deep inside her, holding it there as jet after jet of hot cum erupted, seeming to drain a year's worth of sperm deep inside her as she unconsciously milked me through my own climax. Through it all I kept grinding into her, not wanting the moment to end and loving every sensation as I continued to watch and listen and feel her body react below me. We both slowly came down from the moment, my cock softening slightly as I eased from her, while she pulled the bottle free and settled onto her stomach on the sleeping bag once more. I lay down beside her, wrapping one arm around her as we kissed - this one gentler but still full of passion. "Wow, that was incredible Jessi, what brought that on?" I asked.

She grinned and playfully bit my chin before replying "Just was in the mood to show you a different side of me. We'll have to play drinking games more often I think!"

I couldn't help but agree.