Naughty Boy! Ch. 04

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Lust and love taken to a whole new level of debauchery.
15.8k words
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Part 4 of the 5 part series

Updated 10/17/2022
Created 07/22/2004
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Warning: Please ensure that you have read the previous chapters of Naughty Boy! before beginning this story, as this is a continuation of those postings. I would wish to thank all of my appreciative fans, and I hope that you all enjoy.

TheCaptain

My mother, Erica Thompson, married to a very rich and successful businessman like Roger Thompson, knew all the right people and was a member of all the right clubs. She went to all the right restaurants, drove flashy cars and wore expensive ornamentation when out on the town with her glamorous, up-market girlfriends. I did not go to the same extremes as Mom did – I just liked driving a good car and having a bit of cash in my wallet – but I was not as into all the rich-glamour scene as she was, and I guess I really had nothing to prove to those friends and companions who knew me.

It was mid-morning on a Saturday, so I didn't have to worry about going to university, and could just sit back and take it easy all day. I liked the few days of peace and quiet that I was able to get, and because Roger was working almost all the time of late, I was able to spend most of that free time with Mom.

One day, as I was cuddling with her on the huge bed, our bodies entwined and coated in mixed sweat from our earlier loving exertions, Erica raised her head up off my chest to look me straight in the eye.

"Oh honey, you're the sweetest thing… I don't know how I've deserved such a fantastic son, but I'm so very thankful, my darling." Without so much as a moment's hesitation, Mom kissed me on the mouth, hard, with so much passion it almost overwhelmed me. Her tongue slid in between my lips and down my throat, while she reached down with her right hand at the very same time to wrap her hand tightly around my limp prick.

Slowly, with tender-loving care, Erica began to tug me off, working her hand up and down the full length of my dick as I leaned back all the way into the pillow as far as I could go and closed my eyes tightly, trying to keep a semblance of self-control as wave after wave of pleasure washed over me.

I could feel Mom moving her left hand up and down my right thigh, and then she worked it up til it was resting lightly on my muscular, well-chiselled chest. Her long, red fingernails, which I could not see because I had my eyes clenched tightly shut but I could imagine just as clearly all the same, began to lightly scratch their way up and down my chest, and I let out a sharp gasp of pleasure as the passionate feelings building up inside me reached a catalytic crescendo.

It was one of my favourite things, to have a woman run her long nails all over my super-sensitive body. Especially when it was my magnificent mother, Erica – she was the most incredible babe I had ever had the pleasure of fucking, and I had known a lot of women in my short but varied sex life.

Tugging off my wood-stick with her right hand while running her fingernails all over my chest with her left hand, I grunted and gasped in pre-orgasmic delight as Erica used all the formidable skills of her experienced years to cause me the most pleasure that she could. I had to open my eyes and look back at her, and when I did, I found that she was already staring straight at me. Our eyes met and we exchanged knowing smiles, then she kissed me for the third time and grinded her body up against my side, sliding her moist wet pussy up and down my leg.

I needed to fuck her, needed her so badly it was tearing me up inside. So I moved both of my hands around til I had a firm grasp of her big, meaty butt, then began to squeeze and mash the cheeks of her ass, pulling them apart and then quickly slamming them back together again in rapid succession. I kissed her passionately on the lips, on her chin, on her nose and down her neck. I pulled her hurriedly around until she had straddled my waist, and I could feel the mushroom-shaped head of my dong slipping in between the moist lips of my mother's dripping pussy-hole.

The sensations that coursed through my body were radiating out from the very tip of my cock, which was sinking inevitably into Mom's suctioning smoo. Oh Lord Almighty, it was amazing. Every time I got a piece of my mother Erica's magnificent pussy I was blown away, and found it even better than the last time.

There wasn't a force on Earth that would have stopped me from getting the very thing that I wanted most, above everything else. I grabbed a tight grip on both of Erica's hips and quickly slid all the way inside her, filling her up to the brink, jamming every last inch of my cock up inside her hugging wet tightness.

Soon, Erica was bouncing slowly up and down on my throbbing, rock-hard prong, getting slowly drawn into the pleasurable sensations of the debauchery, her cunt gently squeezing and releasing my dick as we eased ourselves into a rhythmic fucking motion. I pushed the forefinger of my right hand slowly into the tight crevice in between Mom's butt-cheeks, seeking out the tiny puckered hole of her anus with the tip of my finger.

When I found it at last, pushing in against the super-tight, wrinkled orifice until it began to give out under the pressure, I leaned over and slipped my tongue into my Mom Erica's mouth for her to suck on. Pushing in as hard as I could, I managed to get almost the entire length of my forefinger in my mother's clenching anal duct, while I continued to slide my cock in and out of her wet, tight twat all the while, not once easing up on my brutal fuck-tempo.

She began to raise and lower herself faster up and down on my prick, and I could feel a sense of near-desperation coming over her as Erica sought her own sexual release. Her body was tightening up on the inside for a climax of gargantuan proportions, while sweat coursed down the length of her body in rivets, and her face and upper torso were flushed with blood.

I grabbed onto Mom's left shoulder with both hands and used my arms to help drive my own thrusts deeper into her sensational snatch. She let out an earth-shattering scream as the pleasure simply overwhelmed her, while her body was wracked by wave after wave of orgasmic seizures and the walls of her cunt threatened to rip my dick completely off as it clenched down on my rigid pole. It was as though she had been waiting for that very moment to unleash a torrential flood of thick, clear girl-cum all over my blistering cock and balls.

"Oh shit baby… oh Jesus fucking Christ yeah." Mom slowly coasted down from the heights of her orgasmic passion, stroking the side of my face tenderly as she continued to slide up and down on my prick.

As she came, I could almost feel my own climax rushing on at the same moment, but then something peculiar held me in check and I did not blow my load. Instead, I let out a long sigh and the tension just seemed to seep out of me. The urgency and sheer passion of the moment was lost on me, at least for the time being – though the hard-on definitely wasn't!

She was so beautiful right there at that precise moment that words alone could not adequately do her justice. With the light coming in through the window to the west, shining down brightly from the sky high above, Mom simply looked positively glowing. For the millionth time over the past few weeks that I'd been screwing my mother and her younger sister, I had to thank the gods for my good fortune.

I just hoped I could make the fun last forever…

Reaching up with my left hand to squeeze Mom's tits and pull on each one of their hardened nipples in turn, I started to gently thrust my dick up into her twat again, taking Erica a little by surprise. She let out a soft, sharp gasp of surprised pleasure as I worked my prick-stick steadily in and out of her slippery, tightly-clenching pussy, and then groaned from deep down in her belly when I hooked my finger a little bit inside her anus and pulled back on it. Soon enough, waves of heady pleasure were washing over Mom as I kept on masterfully fuelling the fires of her desire, goading her on with the way I teased her and the skill in which I loved her.

Pulling the finger at last out of Mom's ass as I rolled her over onto her back on the bed and moved over with her until I was on top, I made sure both of her long, sleek sexy legs were swung around on either side of me and then hurriedly guided the head of my penis into the pink, fleshy folds of Erica's hot, sopping wet pussy. I slid slowly into the opening from whence I came until finally I had all 9" of my monstrous member buried up to the hilt inside her. God, it was the tightest fuckin cunt… I loved it!

Working my prong rhythmically into and out of my very own mother's aching, gripping twat, I felt beads of sweat begin to form along my brow and down the length of my back, but I brushed the discomforting feelings aside and just kept on persevering. Erica was soon grunting and moaning like a stuffed pig, her eyes bulging wide and her mouth hanging open as I drove into her hard with every thrust and left her longing for me with every withdrawal.

"AAAHHHH FUCK YYYYEEEEAAAAAHHHH LLOOVVVVEEE MMMMMEEEE!!!" Mom moaned, arching her back and letting out a raggedy shudder, her body trembling with pre-orgasmic pleasure as she began to tense up in arousal.

I needed to get off desperately, and knew that I would have to have her from a different angle to get the friction that I needed to cum. So I helped lift Mom's legs up over my shoulders and began to go to town on her gaping, saturated cunt, driving my prick in and out of her like crazy.

It just felt so wonderful and so right, it almost made me think life couldn't ever get any better… but then I fucked her somewhere else, in another variation… it always did seem better than the last time, no matter how good that last time might've seemed to be.

"OOHHH SSSSHHHIIEEETT…" I gasped, feeling a tingling sensation start to grow from my swaying ball-sacs and spread quickly out to every other inch of my body. I was soon alive with radiant energy, from the very top of my head to the tips of my toes, and my swollen, blood-gorged cock, jammed all the way up inside Mom's squeezing love-vice, swelled up like a balloon inside of her to the point where I thought I was going to cum for sure.

It was just mind-blowing. I felt as if I was literally going to fry my brain inside my skull, such an intense, almost primal sense of pleasure was washing over me. My ass-cheeks clenched and my balls throbbed achingly as they banged a regular tempo against the firm, round orbs of Mom's own backside.

I leaned in and kissed her hard on the mouth, shoving my tongue down Erica's throat and pushing her long sleek legs in almost to the point of inflicting pain on her joints. She kissed me back just as hard and her hands came round to grab onto my ass. I worked my way slowly around Mom's face, kissing and nibbling on every sexy inch of her, til I had my tongue in her left earlobe.

"Oh Lord I need to cum so much, Mama…" I whispered into her ear, and a rippling wave of ecstasy coursed through Mom's body after I had finished talking, almost as if this admission on my part had turned her on and made her have a mini-climax.

"AHH YEH CUM FOR MOMMY!" Erica groaned, driving her hips up against my downward thrusts and using the muscles of her vagina to clench down on my rigid dick-wand while the opportunity presented itself.

But it was a little bit of luck – mixed in with Mom's own natural sense of sexual inspiration – that sealed the deal and had me cumming buckets of jizz all up inside her.

Erica reached around with the forefinger of her right hand and suddenly pushed it fair up my tight, puckered rear end, causing my anal-duct to clench and contract quickly around the intrusion.

At first, there was a sharp, intense stab of pain, then a dull, achingly throbbing sensation as the initial jab subsided and my body began to adjust to the unexpected invader. It took me a few moments to realize after Mom had shoved the finger up my ass that I had been cumming, but when I finally did come around and my mind computed what was happening, I was immediately swept up in a whirlwind of sensations.

I didn't even have any idea that so much semen had been building up inside me, but the gooey, sticky, extremely messy evidence was irrefutable. The throbbing, pulsating rush of cum that tore out of me felt more like a flood of piss flowing through my cock than a orgasm, and I had definitely never cum so hard before that very moment in my life.

There was so much jism that I felt it oozing out of her and over my balls even before the last spurt of spunk had shot out of my cock. I collapsed on top of Erica and just lay there where I lay, exhausted and totally unable to conjure up even the briefest burst of energy required to move off her chest.

We stayed locked together for the longest while, the both of us gasping and panting as though we'd run a marathon, our bodies drenched in sweat, both of our hearts beating away like prime race-horses in full gallop… I myself was breathing so hard I thought my lungs were going to burst from the strain.

"Oh Mom, you spoil me so much it's almost criminal…" I sighed, stroking her naked back as my limp cock at last slipped out of Erica's cum-bloated pussy. A thin trail of jizz still linked the head of my schlong with her puffy, swollen cunt-lips… but neither one of us really cared about that, or the fact that we were both sweaty and reeked of sex, or the fact that the bed sheets were slick all over with our combined love-juices.

None of that mattered a good Goddamn when two people who loved each other as much as Mom and I were making love… the world could've gone to hell in a heartbeat, and neither one of us would have batted an eye.

##

I'd almost completely forgotten about my little escapade with Mandy Swanson the other day while Mom was out shopping, and about the promise I had made to give her fiancé, Charlie Ingram, a call. We had been best friends, a long time ago, and it was about time to let bygones be bygones and get back together again. I could see the wisdom in that now, after the years had passed by and the hurt at my then-girlfriend Mandy running off with Charlie, who I had thought was my best friend for life, who I had always thought would be loyal and true to our friendship, had faded away.

Strange, sometimes, the way life plays out for us…

Picking up the piece of scrap-paper Mandy had used to quickly jot down Charlie's mobile phone number before she had left, minus her panties and with my cum still dripping down out of her well-fucked bunghole, I began to punch the numbers in carefully one at a time before waiting for the call to connect. After a short while, I finally got through, and heard Charlie's voice on the other end: "Heya, Charlie here, how can I help ya?"

"Hey, Charlie! Howz it goin', man? Long time, no hear, hey mate?" I said to my former pal with a smile in my voice. I could not believe I had actually come through, and was actually talking to Charlie, no matter what I thought about him at the moment. There were still underlying feelings of pain and anger, but hey, that was life, and I just had to suck it up and get over it.

"Kenny! Fuckin' oath, man, it's real good to hear from you! Mandy told me you had enjoyed my little gift, as I knew you would man!" Charlie said with a hearty chuckle, and I couldn't help but grin at his brazenness. Oh yeah, he knew exactly how to push people's buttons. That was definitely Charlie Ingram in a nutshell. That was why he was a very good, extremely effective businessman. That's what Mandy had told me, and I didn't doubt her for a second. "Hey man, you should come down to my club as soon as you can, and I'll show you a real good time, I promise you!"

"Haha, yeh I bet," I replied with a slight smile. I had had a talk with Mandy before she had finally left the other day about Charlie and about what he was doing with himself, and she had filled me in on his latest enterprise. It was a ‘gentleman's club', or most commonly known as a strip club. Pretty ritzy, too, she had told me, a place called ‘Sugar & Spice' over in New York. I had to say that my curiosity had been kindled. "Well, I've got the weekend clear coming up, so I guess if you can catch up with me then, that'll be great."

"Fantastic, man! I'll give you the address now…"

The phone call basically dwindled off from that point onwards, but I got the address to Charlie's new club, and we managed to work out a time and a place where we would meet up. I began to anticipate a pretty fun evening of adult games and heavy drinking, and Charlie promised that Mandy would be there as well. She was looking forward to catching up with me again, he told me with a hearty, good-natured laugh.

Charlie definitely wasn't nearly as attached to his future wife as I would have expected, but then he had a way with women that always seemed strange and utterly peculiar to me. Well, to each their own, hey? I thought to myself. Good luck to them both, that's all I had to say about it... they had their own lives to lead, and I had mine to worry about.

The immediate future seemed bright, and full of promise. I just had to make sure I didn't make any mistakes, or commit myself too much to anything that made me feel uncomfortable in any way. But I was pretty sure I had a lot of fun in store for me pretty soon… I had some ‘catching up' to look forward to!

##

Charlie Ingram looked just as I remembered, which wasn't saying much because we'd only been estranged for the last three years. He'd always been pretty tall for as long as I'd known him, and that definitely hadn't changed, as he had to be at least over 7' tall by my rough estimate. With a flamboyant, easy-going personality and a breezy sense of self-assuredness and confidence that never seemed to be lacking under any circumstance, Charlie was made for high-rolling, risky enterprises, where there was big money to be made and a long way down to fall if one failed at the game.

He still had longish, wavy dirty-blonde hair and bright, piercing blue-grey eyes, at once both full of life and utterly devoid of any real emotion. Charlie always knew how to play things right, and was always willing to show people exactly what they were expecting to see.

"Ahh, Kenny, old pal, it's so great to see you again!" he exclaimed, coming out to the front door to meet me when the ‘doorman', a massive black bouncer by the name of Matthew, announced my presence into a collar radio-transmitter. Charlie held out his arms and I stepped into his embrace for a brief, heart-felt hug. It had been awhile, and all the way over here I had been thinking about all the ground we had lost in our friendship. The past was the past and it was time to move on…

"Charlie, mate, buoyant as always!" I shot back, holding him back at arms-length and running an appreciative eye up and down his body. It had to be the suit, I thought to myself – it was an Armani, Navy-blue, and very sharp. Charlie had invested a sizable about of dough to get that suit, and had clearly been measured to his somewhat unique frame. He looked like a million bucks. "Man, you've really got yourself a sleek-looking joint here!"

I was just referring to the outside and the inner foyer of the club; I couldn't quite get my head around what I was already seeing, it all just seemed so opulent and stylish, but I had a sneaking suspicion that the best was yet to come. Charlie, who was leaning the way into the depths of his establishment, leaving Matt behind at the door with a slight nod of thanks, only turned to face me for the briefest moment and gave me a slight, conspiratorial smile, then carried on walking forward. I could do nothing more than follow his lead, which is exactly what I did.

When we got into the ‘bowels' of the strip-club, where all the dancers and customers were milling about the place in naked or near-naked splendour, I felt as though I was in a magical, incredibly surreal wonderland. There were women of all shapes and sizes dancing and swaying, shaking the bounty God (or a plastic surgeon) gave them for the benefit of the customers, covering nearly every race and nationality under the sun. I was quite impressed.