He whispered in her ear, “Remember my promise?” as he gave three slow, shallow thrusts. Shana did. She bit her lip during the fourth slow, shallow thrust. She shook her head in feeble protest through the fifth and sixth slow, shallow thrusts. That frozen rod drained her of all intelligent faculties. He opened his mouth and positioned his bite during the seventh and eighth shallow thrusts. The ninth was infinitely deep, which felt to Shana that he was sliding in endlessly, all the way into the pit of her being. She let out a moan which shook the walls of the stone den.
TO BE CONTINUED
My Bucket List Series – Little Miss Anal
Chapter 1
I must have stared for ten minutes straight at that fucking calendar on my desk.
It was one of those cartoon ones, with a newspaper comic per day on each page, the style of the drawings and humor all lifted shamelessly from Gary Larson, so that the characters all just had fucking black lines for eyeballs. Of course not a single one of them was genuinely funny- perhaps it was the fact of the theft that made this a case. But I can't recall ever having laughed at a single one of them, yet I do recall buying the goddamn thing every year for the past half a decade or so. The series had some dumbass name that made it seem as though it would be the funniest fucking thing you'd ever read- “Square Pegs” or “Your Fly's Down” or “Funny Business” or “Why Don't You Just Go Lobotomize Yourself and Have it Over With?”
The comic in question of course featured a chicken and a cow, topping off the Larsonesque theft, and I'm not sure why the hell I was staring at it for so long. It sure as fuck wasn't the least bit funny. I don't even remember what the weak punchline was, but for whatever reason I was transfixed on it... I dunno. Maybe it was the specific fact that it was so unfunny that I felt so drawn into it.
I absolutely fucking despised this calendar.
I couldn't stand it, and most days I wanted to hurl it against the fucking wall and watch every last page of lifted work come flapping through the air and settle to the floor in a scattered frenzy of debris.
And yet I bought it. Every fucking year, around Christmas, “Welp, I need a calendar this year. Time to go to the goddamn mall and pick up my motherfucking copy of Funny Business.”
And I hated myself for it.
Maybe my hatred for the calendar itself wasn't quite so bad (although it was fucking abysmal,) but it was more like what it represented that I despised.
It was me, religiously purchasing something I didn't give a fuck about, so that I could set it on my desk in the cramped little cubicle at the job I didn't give a fuck about, so that co-workers whose bloated faces I couldn't fucking stand could come up to my cubicle and snoop over my shoulder at it, often reminding me that I'd forgotten to turn the page that day, and graciously doing it for me so that they could get to today's strip. I hated smelling their hellish breath wafting past my nose every time they chuckled at the unfunny jokes- they all had halitosis from eating all fucking day at their desks, the dopamine released with the consumption of food the only mild titillation of their minds they got on any given day. Well, that, and pressing their gross bodies up against me to laugh at my apparently hilarious calendar.
And that was what my life was.
I watched it pour away like sand through an hourglass with the tearing away of each awful page of the calendars, pictures of clowns and outdated pop culture references and cowboys and people on deserted islands with a single palm tree in the middle of the ocean, and fuck fuck fuck fuck fuck.
Everything about me was just a compromise.
I derived no pleasure whatsoever from my day to day life, I just fucking lived it.
I'd consumed myself with getting all the details just right- chug my way through college, amass a small fortune in student loans, get a job that had about five percent of anything to do with what I'd studied to begin paying them back, get used to said job and become so comfortable there that I would probably work there until I died, or more likely they just laid me off for no particularly good reason...
Yeah. I'd worked hard to ensure that everything was just right. Little Miss Anal, carefully assembling every minute detail of my own personal prison, down to the fucking Gary Larson ripoff calendar on the cubicle desktop of my agony.
In case it isn't abundantly clear by this point, I was rather discontent with my lot in life.
It was passing me by, and I was just letting it. There was absolutely nothing in my days that made them worth living, because by the time work was over I was far too tired and far too mindfucked to do anything remotely enjoyable. So I just went home, laid alone in bed, and watched shitty TV on my laptop until I fell asleep. I would wake up the next morning, an entire season or so past the point where I'd left off, and I wouldn't even rewind the fucking show. I would just tune right back in for an hour or so before getting ready for work, because it wasn't like I was actually emotionally invested in whatever garbage it was. It was just something to numb my senses for a bit. Emotional substitution, I guess.
I couldn't even remember the last time I'd had someone else in that bed with me.
Isn't that awful?
It must have been a fucking year or so since the last time I'd had sex at that point... I mean, the creeps at my office sure as hell weren't getting beneath the sheets with me, and where the hell else was I supposed to meet anyone? I drank alone at home, tucked beneath my covers, and any old friends who might have hooked me up all lived halfway to fucking China at this point. What was I going to do, start hitting on fucking grocery store clerks whenever I went out shopping? I was better off just buying a fucking cucumber to stick up my crotch and having it done with for the day than I was wasting my fucking breath.
And I wasn't always that way, either, and I think that's part of what made it worse.
I'd had a pretty banging sex life in college. I don't know if party girl was quite the right term for me- I certainly wasn't the wildest person there. But I mean, if you're even a remotely attractive girl in an environment like that, it's pretty likely by the time you graduate you'll get bounced off more cocks than you can shake a prick at. (Yeah, I know. That last bit didn't make a lot of sense, so sue me. Just let me bitch and don't interrupt me.)
I'd had a LOT of good sex in college. I had my legs open more than my textbooks, I studied male anatomy more than I studied my actual coursework, I hit the sheets more than I hit the books, etc., etc., fill in your appropriate innuendo after the beep.
College is like the fucking sexual goldmine when it comes to eligible, insatiable males, and I certainly made wonderful use of the easy access while I could.
Sometimes, remembering those days, I started squirming in my seat at my desk, getting hot and bothered and overall quite horny, picturing the muscular gym rats who'd fucked me like an animal in their beds, pummeling my cooter like the needle of a sewing machine smacking down, THMP THMP THMP THMP THMP, getting wetter and wetter and wetter between the legs as I remembered the long lost lust for the sensation of cock seeping into pussy, the pink warmth of my body swallowing a guy's prick, spitting it back out, and gobbling it back up again, as though it was more me swallowing their bodies than them having to thrust, and I swear to God I just about started cumming at my desk just fucking thinking about it, not even having to lay a finger on myself, but the memories alone making me lightheaded with arousal, oh, oh, oh, oh...
And then Paul from accounting would stop by my desk.
He would rub his fat, cream-filled-donut-inflated belly against my shoulder, and I would watch the crumbs of food dance on his mustache as he droned on about whatever mind-numbing paperwork he was handing me to file, and I would smell his halitosis bleeding through the air into my nostrils, and he would reach over with his ass in my face to pick up my cocksucking Funny Business calendar, then laugh more uproariously than any sane human being should at one of the unfunny jokes.
And there went my libido.
God fucking dammit.
This had to stop.
I co
uldn't keep living like this, letting my best years slip behind me while I went about life unsexed and unfulfilled in just about every aspect of my pitiful existence. There had to be a change.
And there was going to be.
I could feel something blossoming inside me, a sudden burst toward freedom, something that I was absolutely sure I had to act upon now or let it go forever unfulfilled thereafter.
I stood up from my chair.
I picked up that calendar from my desk, and I threw it in the trash bin as I walked out the door, leaving early and unannounced for the first time ever in the years that I'd been there.
Little Miss Anal was about to be unleashed.
Chapter 2
Actually, it wasn't quite that simple.
See, I wasn't really sure what I was doing, and I probably wouldn't have figured out a way to make myself go through with it if it hadn't been for the inextricable inclusion of lists into my day to day life.
I got the idea of a bucket list. People in situations similar to my own, writing down all the things they wanted to do before they croaked so they don't forget to do them over the course of their miserable, mind-numbing lives. And I mean, they were all pretty much the same list. “I want to sky dive! I want to bungee jump! I want to travel! I want to dance like no one is watching!” Like, it's all just sort of stuff that people think they should do because of inspirational posters at the jobs they hate. They see a picture of a mountain against a black backdrop, with the word “REACH” written in big bold letters underneath, and suddenly their life goal is to climb fucking Mount Everest.
And I guess there's nothing wrong with that. I guess I can get past my surliness to admit some of those things would be pretty fun. Like I've always kind of wanted to see the Northern Lights, so... I guess when one of my main goals is to see some flickering lights I shouldn't chide other people for what they want to do with their lives.
But, at any rate, my list was driven less by wonderlust, and more by just plain, good old fashioned lust.
See, it took me a while to get it started, but once I got on a roll, it became pretty easy to think of things to write down for it. I did some internet research as well- among other things, looking through porn categories to help me come up with ideas.
I was putting together a list of things I decided I wanted to try sexually, things that would push me past my limits, and I eventually started getting so aroused by the idea that it was like I couldn't stop writing. I must have had forty or fifty things down at one point, from shagging an eighteen year old again, to fucking another woman, to joining the mile high club... But I crossed off most of these about as quickly as I thought to write them down. Like... Pee play? I watched some videos of that and was a little turned on, but... Well, it seemed like one of those things that, if it was titillating at all, it was only so in watching someone else do it, preferably on screen, and several such similar items were quickly cut away, including but not limited to dressing up like a furry, and-
You know what? Forget the cancelled items. I'm kind of embarrassed to admit half of them...
Suffice it to say, I eventually trimmed it down to a neat enough quantity- ten items, none of which I'd ever tried, a fact that made me realize just how incredibly limited my sex life had been up to this point.
But still, it was a start, and having everything listed out in front of me might just be enough to help keep my nose to the grindstone and my knees around my head.
I was going through with this, and I wasn't going to back out.
I called it, aptly, the Fuck-It List.
Fuck all the empty standards I'd set for my life up to this point that had only ever managed to trap me in my unhappiness. Fuck other people telling me what was good for me. Fuck it all.
Fuck Little Miss Anal and her obsession with doing things the right way.
In fact, I intended Little Miss Anal to be the first person crossed off of my list of virgin personas...
I had two main means of going about finding meat for my consumption, if you want to objectify men in such a base manner according to their funky parts (which I most certainly did.) I lived in a pretty metropolitan are, so finding sausage seemed like it wouldn't be much of a problem. But I didn't want to play the endless game of cat and mouse looking for someone to chase my tail. No endless flirting, no buying drinks for men across a bar and searching high and low for just the right guy.
I would turn to the one surefire place where there was always someone ready to spread your legs apart for you and start pumping away within an hour of initial contact- the internet.
I opened up my computer and turned on my webcam. I found an app that set the photo taking software on a timer, and I set that up as well.
Then I got naked.
I peeled out of my clothes, down to my birthday suit, and started touching myself, getting myself in the right mindset. You know, tweaking my nipples and getting them hard, pushing my fingers up my pussy and pressing the pink wet meat around, then pulling my hand back out of myself and tasting my own fluids...
Hell, I was a lot kinkier than I thought I was now that I was actually getting myself in the right mindset for it.
I didn't record my doing this stuff, I should point out. I wasn't quite ready for that...
But I did get myself quite hot and ready (not to mention as sopping wet as a washed up beach towel) and it got me limbered up enough for the task at hand.
I slipped into a tight set of lacy red lingerie, a skimpy little bra and a pair of thong panties so tight they practically split me the fuck in half up the ass crack.
And then I started posing.
CLICK, CLICK, CLICK went the camera, as I shifted through my most ridiculous, and therefore sexually appealing stances. My spine curved. My hips thrusted unnaturally high into the air. One hand on my waist, the other pushing up my right tit in its cup. Bending over, so that the g-string ran ridiculously high up my ass crack, looking like it might get sucked into my fucking body. Taking the bra off, and holding my arm across my chest like a censor bar, covering the nipples up, and thereby making my tits look enormous as they pressed up against me. And then, why the hell not? Just for the fuck of it, with my arm still across my nips, I reached my other hand down into my panties, the fingers about halfway down beneath the fabric so that it looked like I was getting ready to masturbate as the timer went off.
And then... Fuck... I did masturbate.
I was just so caught up in the idea of what I was doing that I couldn't help but enjoy my body a bit while I was at it, pulverizing my pussy with my own hand, churning myself up like an Amish person churns butter, rubbing and rubbing and rubbing and “Oh, oh, oh, oh, OHHHHHH...”
Christ. It was a good thing I started this list shit when I did, because I was only just now starting to realized how fucking sexually repressed I was getting.
I had to dry the cunt fluids off my hand before going over to the computer and putting my pics to good use. I'd intentionally and successfully kept my face out of almost all of them, and in the three or four that I hadn't managed to I went about cropping my head off with some photo editing software.
Once I had a nice little batch of my snatch, I began uploading the photos in the two places I mentioned earlier. I didn't know how easy it would be to get different sets of bodies for all the different things I wanted to try, and so I wanted to send out requests for all the different things I was looking for right away. For the more “basic” challenges, like this first one, I would use a typical dating site, and just search for people looking for casual sex. It seemed like it should be easy enough to find takers, and I could be a little more choosy with who I let into my body.
For the more extreme things, which I imagined might be a little more tough to find takers for that fit my qualifications, I sent out anonymous personal ads, describing exactly what I wanted, and what the terms were for me to involve myself with someone in that capacity. I sent out about six different ads in total, though I eventually had to space them
out for a couple of days to avoid getting flagged as a spam poster. I just put the things up in the order they appeared on my list- I didn't mind if things got jumbled up a bit, just as long as I was sure to cover every base. I also replied to a few other people's ads if they seemed like they were already seeking what I was, and in a few cases that panned out.
There was also one case where I had to write a very specific e-mail using neither of the aforementioned routes. I suspected this one might be the most tough to snag a shag for, and I sent along a few of the photos I'd taken without cropping out the faces, just to have a better chance of landing it.
But you'll find out more about that later...
For the time being, with all my appropriate channels of sexual communication utilized, I began to browse the dating site for my first kinky conquest.
Now, I don't know whether you've ever been a woman looking for casual sex on a dating website, but browsing through profiles is like looking for a needle in a hay stack. Or, more aptly, looking for a worthwhile cock in a sausagefest.
I mean, let's face it, there aren't many guys who wouldn't accept casual sex if offered, regardless of whether or not they choose to admit it. And they aren't quite as choosy as women about it, at least not online, so when you set your search results to casual sex you pretty much end up with every swingin' dude on God's green Earth. And I can speak for no one but myself here, but in my humble opinion, very few of them come anywhere close to cutting the mustard of sexual viability.
Hipsters with blasé expressions, ridiculous haircuts, one fucking eyebrow cocked in an intellectual pose so that you can tell they think quite highly of themselves, and beards that make them look like Amish men (this is my second Amish reference over the course of this story, isn't it? I must have a fetish or something. Remind me to invest in some Beverly Lewis books when this is all finished...) Chubby toeheads in sunglasses with tough guy expressions on their faces, flipping off the camera. Scrawny shirtless guys with tattoos and sad faces, who quite frankly have no business whatsoever being shirtless...
The Naughty Collection Page 8