Sheila’s Training Ch. 02

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After my post-dinner dumpage was done I took stock of the clock and the training exercise in front of me.

The smallest plug was a slender-looking pole of black rubber about four inches in length. Compared to its comrades it was petite, I reassured myself– small comfort that was, since if Matt was to be believed, those would also be going inside my tight lil’ bottom before long.

A sigh shook its way out of me as I changed into something more comfortable. Since I was going to be doing something dirty, maybe getting dirty in the process, I fished out some lycra leggings from my laundry hamper and put on one of my insouciant baby-tees (Bam-Bam and Pebbles: “We Be Clubbin'”) sans bra so I could have access to everything when the time came for cumming.

With the leggings down at my thighs I squirted some lube and began to rub my hind hole like before. Mmm, I could get used to this. The anus makes for a funny little button. Hidden back there. So sensitive to the touch. I let it suck in my finger-tip. It was like I could hear my asshole cooing or something. In a way I felt naughtier than I had when Matthew was watching me do this earlier. After all, I was here on my own, I didn’t have the excuse now before God and Country that my gay sidekick made me do it. I was a free citizen, just a farm-fresh, freshly pooed American gal hanging out in her dorm room, and why was I standing there probing my rectum with a lubricated digit, eh?

As it happens, in prep for sliding a sex toy inside of it, natch.

So there I was, lubing up an anal toy for the first time. Mind you, I have a bullet vibe for my clitty and a silicone Rabbit-type vibrator that could pass for a Canadian Olympic totem in case of a parental dorm-raid. So it’s not like I’ve never gotten off with a sex toy before. Still, this was virgin territory.

For a few moments, as I caressed the soft rubber probe in my wet fingers, getting it impossibly slick before blast-off, I almost wished I had Matthew here to order me around. The reassuring insistence in his voice had really taken me places, in more than one sense. He had put me in my anal zone, that’s for sure. Maybe it was something more like SubSpace.

I finally reached back with that thing in my hand and used the other to yank my right ass cheek off to the side a bit. Novice that I am, I might have been trying to poke my perineum (ha ha, ‘taint’, ‘taint it?!) before I managed to square up the pointy tip with my butt hole. I was hardly willing to put the slightest pressure behind it, and my asshole didn’t feel yieldy. Shit. I passed the probe to my other hand, reached back again with my slick finger. Ahhh. Rub rub rub. There now, I mentally told my asshole. I let it suck my fingertip in again. I got more vigorous, started fucking back and forth inside the tightness. The tight mouth fit like a hot little glove, but it was open now, curious, inviting. I smiled to myself, feeling all bleary again like I had before with Matthew. Like a drug almost.

I tried again with the plug and it immediately found its target. My anus sucked the tip in. I let it sit there a few moments, let it slide out till I could feel the very tip just asking for entrance, and then I put some weight behind it. I didn’t bottom it out (!) but it was in a ways. I slid it out some, and back in. So smoothly it went. Like there was no resistance at all.

I got kinda bow-legged standing there with a slightly naff scent coming up from my unlaundered leggings (or was that a fresh odor from my snatch?), working that toy in and out back there. Before I knew it I had pushed it in one time and it was in to the hilt! My hungry little anus was kissing the little tapered ending and the rectangular base of rubber was now housed back there in the cleft between my buttcheeks.

I was so pleased with myself I raised my arms up above my head and started to do a little güvenilir bahis impromptu victory-boogie, but before I had jacked my pelvis to the Lady Gaga hymn inside my head for a few measures I started to feel this sliiiiiding coming from down below. Shit! I reached back and firmly pressed my plug back inside me. This filled me with more than one sense of relief! Oh, fuck yeah!

I pulled up my leggings and got even more serious about my celebration. I put on Gaga for real and let my body squirm. Probably you’ve realized by now that my affectations to Goth-lite-lite are about as bogus as they come. Talk about ‘perky Goth’? Christ, I’m worse than the heroine of “Vampire Kisses” or something. Hahaha, I love that title. I made little sucky kiss-kiss noises, all the while very aware of the kiss-kiss action the hole in the center of my pert swinging ass was doing. That slender plug wouldn’t quite stay buried to the hilt. It didn’t feel like it was gonna pop all the way out and stick there like a crap I’d taken inside my leggings but, all the same, I sure wouldn’t want to venture outside trying to hold it in. It was like the bottom inch kept wanting to slide out for air, so I’d have to reach back and pat the base back in place. Which was fun, actually. It was making me feel like a messy anal slut. My secret friend and I were making hot conversation with each other.

I was starting to think about making up some kind of ass-appropriate play list for this and future butt-plug fueled bedroom dance sessions when Ted called. Looking for a booty call? Well, that’s not really how he rolls. If it’s weekend love it’s usually scheduled in advance, and if it’s a weekday it’s probably some civil chit-chat on Hobbesian assumptions in the “Discourse on the Origins of Inequality” or something. ‘Assumptions’: pun acknowledged, but not intended! –“Yes, why don’t you come over?’ I told him. I was only twenty minutes into my mandated training session. It could be fun, keeping a straight face while I’ve got this thing fixed inside of me.

Ten minutes later he shows, wearing a not-too-baggy grey henley and some neatly-whiskered jeans. I’m guilty of dragging him a bit toward the metro-side of the equation, I know. He’s so cute though. I keep him on a fairly short leash when I want.

I was sitting demurely when he arrived– I had no intention of cutting Ted in on my training activities. Maybe when it’s all done he can enjoy some of the fruits of my endeavor? Not that he’s given to outrageous moral panics, but you never know– these philosophy majors can rationalize some pretty extreme positions that have nothing to do with real life.

“Oh my god, so I was checking out the shelves of new paperback acquisitions in the library, and you wouldn’t believe– we’ve got new Oxford editions of Duns Scotus, Erigena, an anthology of Warsaw Circle essays in modal logic pre-1937, there’s some Midwestern University Press edition of Karl Marx’s student essays going back to when he was eleven, not one but TWO new monographs on–“

“Hm-hmm,” I said brightly. “You’ve had a busy day!” I exclaimed, like a proud momma admiring her son’s drawing– as if he actually had something to show for his day. Or as if I didn’t have something to show for mine! –“Why didn’t you bring them all in with you?” I asked, actually just mildly curious to see these riches he was bedazzled with.

“Oh, there’s the whole two weeks waiting-period before you can check them out. I’ll just have to sit in the library and read them there.”

“Oh you poor dear!”

“Yeah, I won’t keep you long really, I’m going to head back and stay out there till they close at midnight. God, I don’t even know where to begin. Those Marx essays, you won’t believe the precocious insights he had into the color blue–“

I let him ramble. I know he might sound a bit ridiculous but really I like him for his ability türkçe bahis to be excited over abstract things. There need to be more people like that, I reckon. Anyway, while he went on about how the Western value-structure seeks to alienate us from the primary colors I wasn’t feeling the least bit alienated from my hot backdoor. I sat there on my bed while he stood and rambled, and I gave my tush little rocks back and forth and felt the probe in my bottom like a warm rod reaching sweetly into some invisible core inside of me and radiating, radiating this liquid warmth outward till I felt it burning inside every pore. There had been a bit of drizzle outside and Ted had little droplets on his glasses and his hair was kinda mussed and, standing there, I just started to feel about him like he was this cool damp furry critter that I needed to rub up against to work off some of this heat pooling on my skin. Thoughtlessly I reached out for him and crooked my fingers in his belt loops.

“Come here,” I said, not tugging, just holding him like that.

“What– what is it, Sheels?”

I took a firmer grasp on his hips and motioned him forward. “I just think you need a little reward, big strong boy like you thinking all these big penetrating thoughts,” I cooed, getting him close where I wanted him while I put my hands up under his shirt and rubbed on his belly. I was looking up, beaming at him. “You’ve got such a long night ahead of you too, I want to send you back to the library refreshed.”

I smirked lasciviously and unbuttoned his pants. I gave him what I hoped was a sexily demure sort of butterfly-lashes look while my hand was stroking him through his–oh Jesus– tighty-whities. Must work on that. “You don’t mind, do you?” I asked hopefully.

He looked unsure but I just went on with my cooing banter. “I know a real scholar like you would never submit to a blowjob in the stacks like those dirty loser would-be thinkers, those fucking poli-sci majors or whatever they are, do with their little library cock-trawling whores but, there’s no reason why a man of Genuine Intellect shouldn’t get a little BJ action in between all his bouts of philosophical heavy lifting– is there?”

When you’ve got a doorstop in the backdoor, these kinds of things come to you.

Ted couldn’t seem to formulate an objection, so I pulled his dick out from its tighty tent and started to stroke it while I went on. “I’m going to be thinking real hard about all the amazing ideas you’ve shared with me when you’re gone, but that’s nothing compared to the worlds of discovery you’ll be unlocking for yourself back in the library. And I know you’re gonna need all your energies to wrestle with all those Great Thoughts, and the last thing an intellectual hero like you can afford is to have his nasty little cock trying to intrude upon all his Heavy Thinking. So– I think it’s probably my duty to all the Graces and Muses and all those other hussies to take care of your animal urges before you get back to the Temple of Knowledge so you can do your thing in peace. Yes?”

Poor boy, his mouth was fixed in a silent O, so I matched it with one of my own by fitting the head of his cock inside my mouth. I wasn’t quite done teasing him so I just let it get wet and warmed up, stroking the peehole very softly with my tongue while I fit my lips tightly around the base of his cockhead, my fingers stretching back the foreskin tautly. I let it pop out of my mouth and eyed the smooth hard form of his cock admiringly. My fingers were rubbing it in smooth rhythmic strokes, from beneath the head to its base. With his undies still on it was like this smooth disembodied appendage. It made me think of shaving his crotch sometime.

“Do you think you can stay standing for this?” I asked. I really did like this little game of meek service to my scholar-boy. And I didn’t want to get up off of my tush güvenilir bahis siteleri either.

“Yeah, I’ll try,” he said, thoughtlessly. Good enough for me. I smiled, then gently worked his stiff member out of its cotton confines and got his undies out of the way. With all that around his knees he wasn’t going anywhere. He pulled his shirt off without prompting, so there was nothing in my way and I could savor the full form of the boy. I let my hands roam. He has a nice body, he’s no aspiring Greek athlete but he’s nice to the touch.

I caressed the underside of his cock with just the backs of my fingers, the offending knuckles that open up my asshole now lingering along his sensitive shaft. I started giving the underside of his glans smooth little licks with my tongue, flicking up towards his urethra, getting a taste of salty precum. My fingers possessively stroked the top side of his dick. When I let the whole glans pop back in my mouth I started rocking my chest back and forth, my hands taking hold of his hips, pushing him forward, rocking his pelvis in little bumps, back and forth. My tongue snaked out to lick the underside of his shaft, then I’d close my lips around his girth and take it in, deep.

I started clenching his butt cheek in one hand while the other rubbed the base of his cock stem. I could tell he was in his zone so I just let myself slide into a good rhythm. I was in heaven. It was like I had two warm popsicles in me at both ends, filling me with slick heat. I had the urge to touch my clit but I told myself it could wait, I wanted to fulfill the letter of my ass training instructions and anyway, this was about Ted’s pleasure. Which made me feel slutty and dirty, made for service. Servicing his very hot and hard cock deep inside my mouth, admiring his taut ass with the stroke of my hand.

Without really thinking about it my hand snaked its way inside the hairy cleft of his bottom and a finger started to rub there. First above where his asshole would be. Then reaching down past it to his perineum. Ted didn’t show any signs of protest. He’s read his Greek philosophers, hasn’t he? I was a bold girl tonight, I didn’t care. I let my finger find that hot dry little button, his rosebud. It wasn’t all nice and slippy like mine, oh no. I’d never really bothered to look at it, certainly never touched it before. I would’ve loved, at that moment, to have some lube on my finger, and . . . But I just rubbed away, rubbed slowly and gently over that tight little button while my mouth sweetly suckled his smooth hard shaft, the sound of his groans very distant, far far away until suddenly his spunk started shooting inside my throat and I milked him proudly, my ass grinding away into the mattress, my rectum clenching madly around the plug inside while my mouth softened around Ted’s cock, swallowing the remains of his spunk and getting him clean.

There weren’t many words after that. Ted lodged no complaints about my stroking the outside of his asshole, which made me very happy. He could tell how happy I was. I tried not to shoo him off too hard, but of course I really did want him to get back to his books now so I could deal with my program.

It was past the hour when I finally got down to getting myself off. I winded up with three fingers lodged tightly in my cunt, not thrusting, just opening me up there while I diddled my skittle frantically, my ass by now feeling like a boiling cauldron. Almost the second after I stood up and had my leggings back in place, the butt plug really did plop out, tenting in the back of them. I fished it out and looked at it, glistening black and radiating heat. I was exhausted just looking at it. I washed it down, running it under cold water trying to cool it off. The sight of its larger siblings was a sweet torture when I sat it inside my drawer. Afterwards I had to dab myself down, backside and forward, with separate wads of kleenex. What a messy girl I was!

I drifted off to sleep early that night, my hips sometimes rocking the mattress in a mindless rhythm of their own, still wakeful with the phantom sense of the intruder out back.

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