Playing Dirty Pt. 04 – Anal


PLAYING DIRTY Ch. 4

The other chapters of this story are in Mature. This will probably make more sense if you begin from the beginning.

Everyone in this story is over the age of eighteen.

And I hope you enjoy this chapter.

**

There was just something about Jon’s cock. All I knew was that I couldn’t get enough of it.

Like right now, moaning with my eyes closed, savoring the taste of him gliding over my tongue, I was in heaven. I’d never been much into giving head before, but since he’d come into the picture, I seemed to be sucking him off at all times, and loving every minute of it.

I loved how my pussy would pulse and clench with need as I sucked at him, already anticipating how incredible it would feel once I’d gotten him good and hard, and ready to fill me up, till I ached. Damn, for a nineteen-year-old kid, he sure knew his way around a woman’s body, especially this particular woman, who was more than happy to let him explore.

“Oh, fuck, that feels good, Serena,” Jon groaned, flexing his hips and pumping his cock even deeper into my mouth, going half-way down my throat, before pulling back to let me breathe.

As he twisted my long blonde locks in his hands, even the slight sting in my scalp as he tugged at my hair and began to fuck my mouth, felt divine. I’d never felt like such a sex goddess until Jon wandered his hot little ass into my life. Until he’d come along, I hadn’t even realized what a vanilla sex life I’d had.

No one ever ate my pussy the way that he did, till I was feverishly slamming my cunt against his mouth, and shamelessly screaming at him, “Oh, fuck me, yes, yes, yes! Just like that, eat me, baby, eat me up!”

Of course, I was happy to return the favor. I smiled around his cock as I felt him grow even thicker as he began to pulsate on my tongue, and knew it wouldn’t be long till he came. His voice deep and raspy, he pulled out and told me, “On your knees.”

I loved it when he went all Dominant on me, so naturally, smirking to myself, I quickly obeyed, got down on all fours, grinning at him over my shoulder as I thrust my ass back, willing to have my naughty lover fill me up.

Every inch of me began to tremble as I looked back, watching him stroke all that long hard man-meat in his hand. The heat in his eyes made it clear that he was preparing to give me a pounding I’d never forget.

Clenching the sheets in my fists, anxious to feel him sliding his way inside me, a little shiver raced through me, my nipples tingling and my pussy clenching in anticipation, knowing that my lover boy knew just how to give me what I needed.

Most guys I’d known, usually just went through the motions of pushing in, doing the old ‘in and out’ a few times, and with a grunt they shot their load and pulled out. But not my Jon, with him, it felt like a naughty new adventure every single time.

Getting up behind me on his knees, still stroking his cock, I gasped as he bent and slowly lapped his tongue over my slit, muttering, “Damn, I love the taste of you, Serena. You’re so fucking sweet.” Then he took his time and warmed me up with a hot little tongue bath and a highly arousal two-fingered fucking, till he had my nipples rock hard and my pussy dripping. He had me tingling all the way from my clit to my hair line, barely able to catch my breath, as I felt him getting in behind me, nice and close, just from the heat of his body. Slowly, he took his time and eased his fat mushroom-shaped cockhead into my needy pussy. Then I smiled as he leaned over my back, and breathed against my ear, “But even more, I love the feel of you sucking me in and milking me dry. I swear, it’s like heaven whenever I’m buried inside you.”

As he started to work his way in a little deeper, I thought how he could be so sweet, and yet talk so dirty.

Our flesh slapping together as he rode me, I was so into the zone that I let out a gasp when I felt him nudging his pinky finger into my tight little back hole, at the same moment he was filling up my pussy with his cock. Shocked, confused, and oddly unbelievably turned on, as he worked that little sucker into me, my mouth dropped open and I really started to pant.

I’d never even considered anal before, but now I was curious to know what it would feel like to have something the size of his big heavy monster pushing its way deep into my virgin ass.

He was just so insatiable, there wasn’t a part of me that he wasn’t eager to explore.

Damn, once he actually slid his pinky past the initial sting and started to fuck my ass with his finger, too, instead of just teasing like he usually did, I don’t think I’d ever felt anything hotter than having both my holes filled and used in tandem. It’s just felt so wickedly good, I just couldn’t stop squirming and shifting on my knees. But when he decided to reach under me and started tugging on a nipple, I almost climaxed from the sensory overload.

It all just felt so good that I never wanted it to end. Everything I owned being stimulated to the max, was nearly enough to have me levitating right off the bed, sure that I’d never felt as turned on in my life.

I could feel my heart actually jump in my chest, when he whispered against my ear, “I got us some lube today, baby.”

I looked back at him. “What for?”

He chuckled. “Thought maybe I’d trying filling up your ass, seeing as you’ve been enjoying me teasing you like this the last few times we’ve fucked.”

“Oh, yesss,” I hissed as he kept up the onslaught, working a steady rhythm in and out of my tingling pussy, while still carefully teasing my quivering ass. “Please, Jon,” I finally begged him.

Then I pulled a face as it struck me, that I might actually have lost my mind, when he reached into the night table for the lube, realizing that I’d actually just begged to have my ass fucked, too.

Wow, I really had become someone completely different with him, someone I barely recognized. Considering I was happy to go along with almost anything he was curious to try with me. And how could I possibly refuse him, when so far, he’d given me nothing but pleasure, pretty much non-stop from the day he arrived.

I felt oddly bereft, when I felt him pulling his cock from my clenching pussy. Nothing I loved more than having him deep inside me filling me up, especially when he was hitting my g-spot. He was just so big, I’d never felt so full or ever felt as elated as when he’d ridden me good and hard, wringing one orgasm after another from me, till I could barely even think, much less breathe.

My eyes popped when he got his face between my legs and spread my butt cheeks open wide, and lashed his tongue from my quivering pussy all the way to my tight little back hole.

Oh lordy, when he poked in with his tongue, and fucked me a little with that too, I couldn’t believe how crazy good it felt as the most indescribable tingling sensation raced through my pussy, all the way up my spine. Fuck, the things he did to me should be outlawed. Guy ought to come with some sort of warning label to warn a girl to beware, because I imagined the ideas he got in his head, were probably illegal in about ten different states.

“I need to get you good and wet, to get you ready, and relaxed,” he explained, as he worked my tight back pucker with his tongue, while sliding two fingers in and out of my needly little puss, till he had her so wet she was squelching.

I believed him, too, glad that he was preparing me for what was to come, seeing as he was hung like a fucking stallion.

“Hmmm,” was all I could muster, as he made love to both my holes with his smart tongue and fingers, sending me right over the edge and into the abyss, as the most perfect orgasm I’d ever experienced began to wash over me, carrying me off on a wave of pure adulterated pleasure.

After coming that hard, just from a little foreplay, I was curious to know how much hotter it would feel when he actually took my ass. Already tearing up the sheets with my hands, I groaned, “Damn, Jon, it just feels so crazy good whenever you’ve got your mouth on me.”

The next thing I knew the little devil had three fingers working my poor pussy into an even stronger climax. While he kept fucking into my ass with his tongue, making me wonder if the tingling sensation racing through my poor pulsing snatch, making it clench like crazy, would ever come to an end.

Too zoned out to even hold myself upright, I breathlessly collapsed, landing face-down on the bed, with my ass still poised shamelessly in the air.

I turned my head and saw the wicked glint in his eye as he stroked his shimmering cock in his hand, that he’d lubed up, till he had it nice and slick. As he prepared me for what I knew would be something pretty jaw-dropping, when he claimed that one last piece of me, that he’d yet to conquer.

“We’ll take it nice and slow, okay?” he said quietly, as he worked his slickened middle finger all around my quivering little butt hole, lubing that up, too. “And believe me once we try this Serena, you’re going to want it again, I promise.”

Since I’d already wanted it enough to beg, I didn’t doubt it. But just the wondered of that big fat cock of his pushing into my tight little bum hole had me tensing up, and my little virgin pucker clenched up tighter than a clam shell.

Before he’d even touched me with it, I thought how much it would hurt, or if I could even take it all, without having to ask him to stop. But as he carefully eased his slick middle finger inside me, though it felt tight, once he worked his way past the resistance of my tightly clenched sphincter, after he’d told me just to breathe and let myself go and relax, surprisingly, it started to feel okay. Gradually, the more he worked it, it actually started to feel way more than okay as he fucked me with his finger, till I was eagerly pushing my ass back, shamelessly begging for more.

“Okay, now I’m going to switch it up, and I’m gonna use my cock. But just tell me if it hurts too much and we’ll stop.”

“Just do it, Jon. Don’t stop,” I told him, hoping I could take it like a champ, because I didn’t want to wimp out, now that we’d come this far. Truth was, I wanted it all. If what we were sharing was gonna have to end soon, I wanted to experience every last thing we could do together.

Then once his sister returned from England, and we had to end it, at least I’d have my memories, I could revisit whenever I needed to. Sure, that this would be something I’d never forget; the first time I experienced anal, especially with someone as gifted as Jon, had me already quaking, as I anxiously thought what it would actually feel like to have someone the size of him, filling me all the way up from behind.

Holy mother-fucker! I soon found out! My eyes shot open and I gasped, the instant I felt him broach my tiny back hole with his big, fat honking cockhead. I’m not gonna lie, that bastard stung like an absolute bitch!

Slightly panicked, eyes-wide, I shot a look at him over my shoulder, pleading with him to take it slow. “Jesus, Jon, you just feel so fucking big. Are you sure it’s going to fit?”

He chuckled. “Baby, just be patient, and it’ll work, I promise. Believe me, I’ve enjoyed this enough to know that we’ll both get into it, if we take our time.”

Partly to take my mind off the insane stinging sensation radiating through my ass, I thought again how at nineteen he could possibly have as much experience as he’d had.

But considering the fact he was flat out beautiful, blessed with the most amazing long-lashed emerald green eyes I’d ever seen, and that ever-present sexy smirk, a delectably chiseled body and of course, one helluva an insanely long, hard cock. I’m sure no woman in their right mind would ever have turned him down, if he suggested that he’d like to get busy with them, no matter where, when or how. No wonder he’d had tons more experience than I’d ever had, though at nearly thirty, I had ten years on him. My love life had just never been all that interesting, at least until he’d wandered into my life.

Letting my eyes fall shut, I did all I could to tune out the pain of being filled tighter than I’d ever been filled, feeling like an over-stretched sausage casing as he stretched me out to the max. Gradually, I began to zone into the pleasure of taking it from behind, as the most indescribable sensation I’d ever felt began to slowly filter its way through me. As he gently flexed his hips, and carefully began to work himself in a little deeper with each thrust, I actually started to smile.

Adding two fingers into the mix, he started to work my pussy, till he had every inch of me feeling like a quivering mass of nothing but hot jangling nerves. Which had me wondering if it was feasible to actually die from coming harder than I’d ever come before, convinced that I’d never felt anything even half as good as having both my holes worked over at once.

My eyes rolled back in my head, as I realized that there really was something to this double-penetration company, which would explain why so many women were into it.

The feeling of fullness alone, packed tight with two fingers working my clenching puss, with his cock buried deep in my ass, was almost too delicious to describe. He had every inch of me humming, sure that I’d never felt anything so overwhelming as being packed to the absolute max, as he magically seemed to hit every last nerve ending, I owned.

I rolled my eyes at the feel of his thick, heavy cock sliding deep into my body, as he filled my tingling cunt to the absolute limit with three fingers now. Tightly packing both my holes at once, had me too overwrought with sensations I’d only ever dreamed of, to even utter a word. I felt like a tea kettle ready to boil over and open my mouth and scream, he had me so primed. Thrilled beyond belief, I started groaning as I felt the first wave hit me like a tidal wave. Throwing back my head, moaning, I happily licked my lips.

Fuck me, this kid knew his stuff. And lucky me, I was the one getting to experience every last trick in his book. And holy crow, was I ever enjoying the experience. The delicious sting of being filled so tight, almost to the point of pain, was almost indescribable, it just felt so insanely good and yet almost wickedly depraved, considering where he was buried.

Each breath was coming hard and fast as I shamelessly began to thrust back, amazingly desperate for even more. Even as the slight stinging sensation persisted, though gradually it was becoming more bearable, and actually morphing into something pretty incredible. It all just felt so dirty and raunchy, and yet so freeing to let myself go like this, that I just couldn’t stop quivering at the wondered of him fucking my virgin ass while working my poor pussy into a tingling frenzy.

There was no way I could deny it. He was right, and I was loving every minute of it. Though he had every last inch of me feeling like it was on fire, from the roots of my hair to the tips of my toes as he plowed into me deeper and deeper, giving my ass and pussy a going-over like I never even knew they could take.

I could actually feel the juice from my cunt dripping down my thighs as the most jaw-dropping climax I’d ever experienced began to tear through me hard and fast, almost knocking me flat. My climax kept mounting and mounting, till finally I reached the peak, and I felt like a woman possessed, tossing my head from side to side, screaming out his name. Quaking and shivering like crazy, sure that I’d never come as hard, I’d honestly had never known such bliss. Damn, as he really began to work me hard and rough, all I could do was gasp for air, while eagerly pushing my ass back, desperately begging for even more. As I felt him beginning to pulsate deep in my body, preparing to come and fill me up with his seed, I silently pleaded for this ecstatic feeling to never end, hoping it could just go on forever. Knowing that he had the power to drive me this wild, just felt too amazing to even wrap my head around.

And he was right, I would want it again, and again and again! It just felt too wickedly delicious to be denied.

What a shameless sex fiend I’d become with him. On my knees, hoping he’d never stop fucking my ass, he’d turned me into someone I never knew existed. A woman revelling in the feeling of letting loose and letting her inhibitions go, unashamed of finally getting exactly want I wanted from my lover. By the time he was shooting his load, splashing his way inside me, I’d come too many times to even count, as my sexy young stud kept plowing me for all he was worth.

Before Jon, I’d at all times been a little shy, preferring to have the lights out, so we wouldn’t have to look at each other, and feel embarrassed about what we were doing, or even having to see each other naked. Yet now, as I looked back in awe at the determined set of his jaw, sweat dripping from his face, as he gritted his teeth, dug his fingers into my hips, and mercilessly pounded my ass, growling like a beast with its mate, I wouldn’t have missed seeing that lust-filled look on his face for anything in the world.

When he finally threw back his head and yelled, “Fuck, Serena, here it comes! Oh man, I’ve never come this fucking hard in my life!” I let go, and came right along with him, shuddering right to the soles of my feet as we climaxed together, my pussy clenching tight around his fingers. And let me tell you the feel of him pumping for all he was worth, plowing as hard and deep as he could go, splashing deep inside me with everything he had, felt utterly indescribable as my whole body just kept on quaking, like an electric jolt was rifling through my veins from his pulsing cock right into the soul of my being.

I could feel my pussy pulsating in tandem with his cock, as we both came hard enough to nearly stop our breath. I’d never experience anything even close to this with anyone other than him — which made me wonder why it ever had to end.

Jon finally pulled himself out of my ass, and collapsed breathless on the bed beside me. I could feel one last shiver racing through me, at the delectable sensation of his cum sliding down my thighs as he tugged me into his arms, captured my face in his hands and desperately kissed me.

Though our life had become like one big, long highly erotic dream, I was starting to think that I never wanted this dream to end.

Of course, you can not at all times get what you wish for. So no bring surprise, just as we were slowly catching our breath, smiling into each other’s eyes, and still playfully plucking at our lips, my cell phone rang. It was Jon’s sister Anne, letting me know that she was coming home a few days early and bringing along her new man that she’d met in London.

“Oh, that’s great,” I told her, doing my best not to sound like I hadn’t just climaxed so many times that I could barely think straight, much less carry on a lucid conversation. Though, shocked at his stamina, I smiled as I slid my hands through Jon’s thick, dark hair while he was busy sucking and licking around my both my nipples in turn, getting my pussy tingling all over again. He was getting me so worked up, I had to fight to keep my voice steady as I asked, “Did you want to talk to your brother, Anne?” half-hoping she’d say no. Because that would mean he’d have to stop playing with the girls, at least long enough to talk on the phone, which right now, I sort of hated to have happen.

“No, it’s okay, knowing Jon he’s probably busy online, or having fun playing one of his games. So just let him know that I’ll be home tomorrow night. And I can hardly wait for you to meet my new man.” I could hear the smile in her voice, and I was happy for her. Although, I had my doubts that she’d be as happy for me, considering that my man just happened to be her little brother.

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