The Naughty Collection

by Ruby City Books

  I had a feeling that the three of us would end up getting together again, sometime very, very soon...

  THE END

  My Bucket List Series – Pegs and Holes

  Chapter 1

  My body was in desperate need of a break.

  Lately I'd been spreading my legs wide across all of whoredom, and with my beloved list down to two remaining challenges, I felt as though I had more than earned the right to give my tired and weary genitals a rest from being relentlessly pounded.

  Currently, I lay wrapped in the arms of my beautiful lesbian lover, Olivia, the shafts of golden morning sunlight streaming in through her bedroom window, causing our already soft and dazed bodies to glow in a sweet, sensual manner, as though lit up through a prism of amber. The two of us stared for a long time into one another's eyes, touching one another's soft bodies, caressing one another, and every so often leaning in to taste one another, our breath sweet and warm and tender, and I think we mutually agreed, the most delicious thing in the world. I pushed a strand of hair out of her eyes, and whispered to her. “You're so, so beautiful...”

  She smiled at me, in that soft way of hers, and said in response, “You're such a whore,” to which the two of us began to giggle like schoolgirls. As punishment for her insult I attacked her with kisses, our bodies writhing together, the heat radiating through our skin, causing us to work up quite the cloud of steam beneath the cover of the sheets.

  There was, of course, a considerable degree of truth to her friendly accusation. After all, she herself had been number three on my list of ten potential sexual conquests, by which I don't mean ten sexual partners, because on multiple occasions “conquests” entailed or would entail multiple partners... However, Olivia had by far been one of my favorite romps to date, my first taste of feminine flesh an absolutely delectable treat to be savored, just barely overshadowing my double penetration with Pete and Repeat in terms of shattering my expectations (and the integrity of my vagina.) Plus, now that I was down to the final two items on my To-Screw List and my sex life would be easing back down to a level that was more or less normal, I thought it was well past time for me to find a nice good pussy to settle down with for a while.

  Olivia's box seemed as though it would hold my possessions quite nicely...

  The two of us pulled apart after some time with light heads and hot and ready bodies, for some reason attempting not to get too riled up first thing in the morning, even though it was a Sunday and neither of us had jack shit to do anyway.

  We continued to stare at one another, our hearts beating beautifully against one another, and I stroked her hair, running the long, chestnut strands through my fingers.

  “You know, if I wasn't such a whore, the two of us would never have met...”

  She smiled, flashing those gloriously white sets of teeth, her grin rather analogous to staring directly into sunlight. “Wouldn't that just be a damn shame?”

  The two of us giggled, and she proceeded, “But- well, never mind...”

  “What is it?” I asked, removing another strand of hair from her eyes. I could have spent a lifetime just playing with that glorious girl's hair and not have been an ounce the worse off for it, I swear to God.

  She tilted her mouth off to the side, in a manner that was about as cute as fucking hell, and then answered, “Well... I guess I'm just sort of curious what all you've done so far... Like...What all is included on this list of yours...”

  I smiled, accustomed as I was at this point to reciting my sexual escapades, and always willing to share with an eager listener. “Well,” I began, like a college lecturer responding to a question that he's always wished some egghead student would ask him, “My first experience was with anal sex...”

  “Shit!” she said, her eyes growing wide, and I could almost feel her sphincter clenching up as she thought about it.

  “You're not kidding. Hurt like hell, but I feel as though I'm a better woman for it.” She laughed at this. “Then I decided to have sex in a public park bathroom after dark, and then nearly got thrown in the clink until I gave my arresting officer a blowjob in exchange for my freedom.”

  “Well fuck... I'm sharing a pussy with a wanted criminal, aren't I?”

  I smiled at her.

  “Then there was you, of course,” I said, putting my hand to her face with almost comical romantic tenderness after I'd just described giving fellatio to an officer of the law as a sexual favor. “My favorite...”

  That God-awful beautiful smile again.

  “Then I took another bang up the bung from a big black bone...”

  “Youch...”

  “You bet your sweet ass, youch.”

  “And then what?”

  “Then was, ummmm... A double penetration- no wait... No after that I screwed the married guy, and then I did the double penetration with Pete and Repeat...” I'd banged so many people at this point that I couldn't keep them straight anymore.

  “Wait... You've done a double fucking penetration?”

  “Yup yup yup...”

  “God, how are you not as stretched out as an old rubber band?”

  I smiled at this. Sometimes, Olivia had just the same way with words as I had.

  “And from there, I finished up most recently by doing my first ever porn video, and going to visit a dominatrix after that as punishment.” My ass was still sore from that one. In fact, it seemed that my ass was receiving the brunt of the punishment through the course of my lascivious experimentation, between having things that didn't belong in there inserted into it anyway and being whipped to a red and tender pulp with a bullwhip. This next item on my list was fittingly, (or un-fittingly?) going to be my ultimate intimate revenge for all the plethora of butt-hurt I'd been put through over the past month or so.

  “Woah woah woah... You've been in a porno video?” she asked, shocked at first, but gradually I could see the arousal washing over her face, and it made me smile.

  “Why? Does that turn you on?” I reached below the sheets and felt around the warm swath of her flesh for her pussy, sinking my fingers into her, and causing her to start as I pushed around the loose fleshy lips, getting my hand all wet as I suspected I would, working my new girlfriend into a pleasant little morning burn.

  “Mmmm... Maybe just a little bit,” she admitted as I fingered her, my manual efforts evidently too much torture for her to withstand confessing.

  “Go get your laptop,” I commanded, and it was with great sorrow that I had to remove my now slick fingers from that perfectly tight gash as she scrambled to fetch her computer.

  I showed her my video, with Mark the porn guy ramming his cock up my pussy, pumping and humping and bumping, and I noticed Olivia's eyes growing wide as she watched, saliva accumulating in her open mouth, sweat beginning to bead through her skin.

  “I take it you like what you see?” I asked, once more stroking her hair, but when she continued to be silent with her mouth hanging open, I decided to just go ahead and stick my fingers in there, giving her a taste of her own pussy fluids, the temptation far too sweet to resist any longer. This snapped her out of it finally, and she responded by looking me in the eyes, taking my hand in hers, and sucking lustfully on the inserted fingers, her tongue swirling around them, getting me just as turned on as she seemed to be growing. She pulled them out of her with a suctioned pop, and let my hand fall gently back onto the bed spread.

  “You might say that,” she said finally, smiling, and turning back to the screen just in time to see Mark splooging all over my pretty little face. She stared at the blank end screen for some time after the video had ended, as though something deep and significant was suddenly plaguing her thoughts.

  “Panty for your thoughts?”

  She laughed. “I think it's penny...”

  “I prefer panties, don't you?”

  Her next laugh was a sigh, my award winning humor paling in comparison to the seriousness of what was on her mind.

  “It's just that... Well... I'm
actually bisexual, rather than just a straight up lesbian...”

  “Oh? I wondered about that. So am I, obviously. Well, that or an indiscriminate pansexual with an insatiable libido, I'm pretty bad at this labeling shit. I just like sex. But anyway, welcome to the club, toots.”

  She smiled, her eyelashes fluttering, and I felt like I'd kept my sarcasm turned on for too long and belittled whatever it was she had to say by mistake. “I'm sorry, go ahead.”

  “Well... Maybe I should say that I'm bisexual in interest, but I've only ever had experience with women... Which is difficult for me... Because for some reason I've always been shy around men even though I'd like to get involved with someone that way, and I'm always a lot more comfortable around other women...”

  Holy hell! My dear beloved bisexual Olivia had never been properly penetrated! This presented some issues for me, as I'd been hoping to ask her to participate with me in the tenth item on my Fuck-It List, which would involve quite a bit of cock in pussy action without going into any further details on it at the moment...

  “Oh... Wow, I... Didn't know that... Well, I wasn't sure when the right time to ask you this might be, but... Well, I was sort of wondering if maybe you might want to help me here soon with the last item on my list. But, um... I'm not sure now whether you're ready for it or not.”

  “Oh? What is it?”

  I leaned in carefully, and whispered what I had in mind in her ear. Her eyes went wide.

  “Holy hell! That's... That's... Shit...”

  I smiled at her dumbfoundedness. “Should I take that to mean I've porked your curiosity?”

  “Well yes, but... But... Well hell, it's like you said, basically... I've never had a penis in me my entire life... How the hell am I supposed to go from an intercourse virgin to that?!”

  “Well... Maybe I could graciously assist you in getting used to being penetrated first... After all, this does also relate well to the next item on my list...”

  “Um... I'm... I'm not quite sure I understand...”

  I smiled lustfully at her, then reached into the night bag I'd brought with me for what turned out to be my weekend stay at her place, and rummaged around until I pulled out something long, hard, and veiny. Then she understood perfectly...

  I harnessed myself up in the series of black straps, harkening back to my days as a child being strapped into a car seat, though if any parent attempted to fasten their child into a car seat that remotely resembled anything like this, I can assure you it would buy them a quick and efficient ticket to a prison cell.

  “You're going to put that inside me aren't you?”

  “You bet your pretty little ass I am,” I said, putting my hand at the tip of my head, and stroking my nine inch shaft with my fingertips, pumping, pumping, pumping, letting the fleshlike material ooze softly through my grip. “Now spread your thighs, sweetheart, and let me teach you a little something about penetration...”

  She shook slightly, staring at my newly attached wang with uncertainty in her eyes, but a smile was beginning to spread across her beautiful face, and I could tell she was growing aroused at the prospect of my proposal. She spread her legs wide, and the loose pink lips of her vagina sparkled with arousal, nearly fucking blinding me with their shimmering.

  Oh yeah... She wanted the D...

  I stalked across the bed toward her like a fucking predatory animal, my eyes gleaming darkly with an intense lust, my tongue lashing out as I licked my lips at her, my own cooter beginning to get quite nice and juicy at the prospect of what was about to happen. In the blink of an eye I was getting horny as hell, but in a way that I'd never really experienced before- like it wasn't even just sex entirely that was turning me on, but absolute power. This cock now adorning my pelvis like some tremendous, pulsing growth was turning me into an animal, and it was as though I suddenly understood for the first time in my life what it must have been like for every last man who had ever penetrated me, or any woman alive for that matter.

  My body was over her now, our loins radiating their heat onto one another, the tip of my erection grazing her soft flesh as it bounced lightly up and down from my body. I leaned into that beautiful head of hers, her frightened breath blowing warmly into me, and I opened my mouth, stuck my tongue out, and slid it across my lover's beautiful cheek, letting my saliva smear across the planes of her flesh, claiming her, like an animal, as my own personal property.

  God, it felt as though the sugar and spice and everything nice that ran through my feminine veins was souring, congealing, and being transfused with all the snips and snails and puppy dog tails that can make men such domineering dicks.

  And I absolutely fucking loved it.

  She moaned as I entered her, shaking like a leaf as I penetrated the loose folds of her perfect pussy, sliding my cock, in, in, in, cleaving her luscious body down the center, stretching out the opening of an orifice that had largely become used to being eaten and rubbed against other pussies. I wondered rather goofily whether this qualified as popping her cherry, but decided for the time being not to think about it. The sounds of her agony as I slid inside aroused me like hell, and sensations began to mount within my own slippery genitals.

  God, oh God almighty how I was loving this...

  I began to pull slowly out of her, following the example of so many men who'd done the same thing through the squishy medium of my own gash through the years, and I savored the sound of my nine inch penis squelching through her vaginal fluids, the rubbing so intense that I could almost feel it despite not actually fucking her with anything involving any of my own nerve endings.

  She was whimpering, a sign which, during the course of our vulva-rubbing tribadism, would cause me to slow down and grow more tender in my movements. In this case, however, it produced the precise opposite effect, causing my blood to fucking boil with lust, and my need to destroy my sweet sweet bitch overpowering my desire to make this easy for her.

  I reared my ass back into the air, then let it come swinging into her body like a hammer, and WHAM! She moaned like fuck as I held myself dug into her body, holding myself so securely inside that I thought it might be possible for my manmade beaver cleaver to start ejaculating all up inside her.

  I knew, of course, that this was impossible, and that you had to order your dildos from Germany or Japan or some shit to be able to ejaculate with them, so instead I did the next best thing and started fucking her lights out with my newly beloved penis.

  I slammed and slammed and slammed into her body, her tits bouncing around on her chest like volleyballs, her eyes squinted shut as I plowed her like a motherfucker, the bed shaking on the verge of utter collapse, our bodies slapping loudly together with each relentless thrust, KLAP, KLAP, KLAP, KLAP, KLAP, KLAP, KLAP, the moans of unbearable sensation issuing forth from her perfect lips like some religious chant, “OH GOD, OH GOD, OH FUCK, OH FUCK, OH FUCK!”

  And as I pressed one final time up inside the moist crook of her vagina, my own body glowing with the slightest pangs of ecstasy, I could feel her form trembling with what she would later describe to me as one of the most powerful orgasms of her life, her limbs twitching, her body convulsing, and such a stain of sweat pooling up underneath her that she ended up having to wash and change her sheets later on that afternoon.

  I thought that maybe, just maybe, I could get used to having a penis I could cram into things...

  Chapter 2

  That's right, ladies and gents and ladies with artificial gent parts. The next item up for completion on my Fuck-It List was, as hinted, to anally fuck a man up his grisly little asshole using my dearly beloved strap-on dildo (my morning romp with Olivia had just been a pleasant little fling to break in my newly acquired cock, as well as to get her warmed up to participate in my tenth and final Fuck-It List challenge here in a few days. For those of you wondering, she did agree to participate in what I will elect to keep secret as my final act of depravity, if somewhat hesitant in doing so. And yes, I realize by now that this is becoming a he
avily overburdened parenthetical tangent, but it should serve as evidence of how goddamn fucking scrambled my thoughts were becoming with this fucking penis strapped to my crotch in my goddamn horniness.)

  Pegging was an art I had long fantasized about engaging in, but never really had the opportunity to indulge in the past. Like, you'd be surprised how many guys are reluctant to let you turn the tables on them in bed and cram something up their backside, now matter how many ridiculous things you let them do to your own body. I mean, stripteases, blowjobs, facials, swallowing cum, taking it up the butt myself, and still I wasn't allowed to indulge my one depraved fantasy of anal agony on a single willing male? I just don't know how gay dudes do it... Maybe my problem up to this point had been that I'd needed a bisexual who was willing to experiment and switch things up as far as roles went, and take it up the bunghole like a champ now and then just to satisfy me. I mean, shit, guys have prostates back there don't they? Taking one for the team surely can't be that miserable of an experience for them...

  But anyway, fuckily for me I had snared a proper buttfucker from one of the online personal ads I'd run, and was set to meet him that Monday evening. And in the meantime, this newly acquired masculinity was creating quite the depraved monster out of me, I don't mind telling you. It was like all the testosterone that cums along with having a penis had somehow been pumped into me when I strapped the motherfucker on, and it made me feel as though I had an immense power over the world around me whenever I happened to be wearing it.

  Accordingly, then, I left Olivia's apartment that morning still wearing the strap-on dildo fastened to my GPA (general pussy area,) my nine inch erection jutting prominently through the tight grey fabric of my pencil skirt as I made my way down the road. I was really strutting my stuff that morning, feeling absolutely goddamn invincible in a way I can't totally explain. I mean, hell, at one point I actually whistled at a cluster of sweaty, sexy construction workers, bouncing my ass just a little bit more, and loving the degree to which I astonished them with my rather overt advances. I could tell that they were doubly baffled, then, by the sight of an erection making a startlingly clear appearance through the fabric of my skirt, and just to fuck with them I decided to scribble down my phone number, then walked over and handed it flirtatiously to the strongest and sweatiest among them.