Sins of the Sitter

Chapter 2: Déjà Vu-2

And with that, my captor leaped off and abandoned me, sprinting out of the room for the nearest extension.

Left alone and denied in mid-fix, I slumped in my bonds, whimpering into my gag. For the next twenty minutes or so, I waited in desperate hope for the resumption of our game. Yet the rapid rise and fall of the dimly-heard conversation going on in the next room showed no sign of winding up. At last, my withdrawal sparked rebellion in me. I began applying myself cleverly and diligently to escaping my bonds rather than just frantically and ineffectually.

It took me another ten minutes; but, at last, I worked my hands free. Then it was an easy manner to remove the gag and free the rest of me. Still more than a little piqued at Jen’s prolonged absence, I left the chair by the window and moved to the TV.

I quickly found some cartoons, and with the short attention span of a seven year-old, I was soon absorbed. After five minutes, I’d forgotten all about my big, intimidating babysitter and our exciting, interrupted game. That couldn’t last, of course. Suddenly, I heard an outraged shriek from behind me.

“How DARE you!”

I spun in chagrin, seeing the meaning of my life glaring at me in unmitigated outrage.

“How DARE you escape from me? Who do you think you are, prisoner? You are my property! You belong to me every second of your life that your parents are out! You do what I say always, and you stay put wherever I place you until I come back to reclaim you, just like a temporarily discarded toy!”

Her blue eyes glared, her face was flushed, and her blooming chest heaved with uncontrollable anger. Seeing her so overwrought, I wilted in fear and shame. And yet, once again, my little p***s began twitching. Swamped in conflicting sensations and emotions, all I could do was cower and goggle up at her.

“Well!” Jennifer snarled. “I think it’s finally time for you to get a spanking! You have certainly earned one with this little stunt!”

She strode across the room, seized me by the ear, and hauled me to my feet. I cried out at this, but I couldn’t resist as she dragged me back to the hard wooden chair I’d lately escaped from. But this time, she sat down in it. Then, for the first time ever, she ripped open my pants and yanked them down to my ankles, along with my underwear.

“Lay over my lap now! I’m going to spank the skin right off your ass! That’ll teach you to disobey me!”

Somehow I overcame my trepidation and did as instructed.

I’d never been spanked before, not even by my parents, who rarely noticed me at all. But as my face hung down toward the ground, it flushed red-hot. Excitement swelled unbidden in me as Jennifer grimly warned me.

“This is going to hurt like hell, iel. But maybe it will show you once and for all who’s in charge around here!”

Then for the first of thousands of eventual times, her heavy arm swung and her big strong hand smacked hard against my bare, quivering little ass.

I barely bit back a cry. It hurt all right! But there was also something compelling about the pain, something unwanted, and yet inexplicably necessary. Jen spanked me again and again and again; and, squirming in her lap, I found myself overwhelmed by a need for something I knew not what. Soon my moans and whimpers had more to do with this feeling than even the ever-climbing pain in my bottom. And young and naïve though I was, I soon perceived an element of enjoyment in Jen, something that went well beyond the satisfaction of just imposing justice.

After that she began leaping at every opportunity to spank me. Not only that, but our games quickly became ever more sadistic, culminating in the torturous yet helplessly compelling cowboy fantasy I’ve already described. And as for me, I gradually became so addicted to laying across Jen’s lap that I began purposely misbehaving, giving her every excuse I could find to pull down my pants, put me across her thighs, and spank me – as she did regularly until I was twelve years old, and she finally left me for the soon-to-be-revealed mysteries of higher education.

***

“Well, iel?”

Eleven years and five seconds later, I’m yanked back to the present by my gorgeous former babysitter in her now entirely predictable new persona. I blink up at her as she crushes me to her huge, leather-clad body, glaring down at me with an impatience and barely controlled zeal that has my already rock-hard c**k pulsing madly in its confinement.

“Don’t you agree that you were a very naughty boy for spying on me today and for buying who knows how much disgusting pornography to jerk off to all these years? Don’t you think you need to be severely punished for all of this?”

Of course, as Susan Sarandon says in Bull Durham, guys will put up with anything if they think it’s foreplay. But, after this flood of recollection, I don’t even need this excuse. Somehow, in my terrible loneliness, I’d put the truly depraved extent of our former relationship almost entirely out of mind the last few years. All these memories now crashing in are incredibly arousing and yet scary as hell.

Do I really want to go there again? And do I actually have a choice? My painfully hard and pulsing prick says that I do and don’t respectively. Conquered again, and this time as a legally recognized adult, I eagerly if uneasily submit to my former and soon to be forever owner.

“Yes, Jennifer. I was a very bad boy this morning. I definitely should have closed the shutters as soon as I realized it was you over there and that you were naked. Spying on you, and treating you like some kind of pornographic s*x object, was inexcusable. I deserve to be spanked now as never before.”

“Yes, you do!” affirmed Jennifer. “And I will amply punish you for that first felony immediately. Later, I will also most appropriately and permanently punish you for jerking off, and for every time you’ve done so before and I wasn’t around to catch you at it. But first, we are finally going to relive some wonderfully exciting old times: the bare beginning of our new relationship. Stand up here in front of me!”

Tremulously, I obey her. And right away she rips open my pants and yanks both them and my briefs all the way down around my ankles, just as she used to. But then my erstwhile babysitter finally reveals real evidence of her recent extreme education.

Instead of just bending me over her lap like before, she first positions me properly and then bends my c**k all the way down until it points straight at the floor. Then, when she folds me over her leathery lap, my erection is excruciatingly back-bent.

Still, in this unnatural configuration, it throbs and burns like never before, and if the pain is magnified alarmingly, then the masochistic pleasure I take in this renewed acquaintance is enhanced even more. I’m keening with need even before she delivers the first of surely another ten thousand or so future spanks.

And then that first one falls: a stinging smack against my ass that is all nostalgia. The pain and shame I feel at being punished by my beautiful guardian is as intense as it ever was. Yet, the arousal is now undiluted, no longer a glandular mystery but a most driving delight. I moan happily at this long overdue re-acquaintance and squirm deliciously as the spanks smack steadily down, a rain of uncounted blows I suddenly want never to end. Soon my entire ass burns with pain, and my face flushed with a most compelling shame, as my former babysitter begins to harangue me as she punishes me in another eerie echo of yesteryear.

“Who’s in charge here, boy? Who has total authority over you? Who is your superior? I am! I am your superior in every imaginable way! I am older than you, smarter than you, and far more educated than you! I’m much bigger than you, much stronger than you, much better-looking than you, and far more sexually desirable. I am everything a human being should be, and you are nothing! Less than nothing! So, from now on, you will always obey me instantly and absolutely, just as you did as a child! In fact, you’re still a child compared to me, and you always will be! So get used to this again, you naughty little boy! I still own you body and soul, and it’s my right, my privilege, and above all, my duty, to punish you whenever I see fit!”

She goes on in this fashion, spanking me ever harder; and, despite my runaway arousal, the connected pain and shame eventually have me sobbing like the worshipful little boy I’ve suddenly reverted to. Only then does Jen at last cease beating me.

“All right, that’s enough. Stand up.”

Painfully I rise, still crying, and stand before her staring shamefully at the floor.

“Stop sniveling! That’s what you get for being a dirty little boy. And stop rubbing your bottom. Let the pain recede on its own.”

Again I obey and try to cross my hands in front of me. Immediately Jen slaps them away, exposing my still urgently upright measly three (if that) inches. She seizes this, easily wrapping the entirety of my erection in her hand, and starts slowly, firmly pulling on it.

“Look at you! You’re crying, but you’re still as big and hard as a pathetic little s**t like you can get. You loved that, just like you did in the old days. Didn’t you?”

“Yes, Ma’am,” I mumble.

“I suppose you’ll begin purposefully misbehaving again too. Don’t think I didn’t know all about that! You’re just lucky I love dishing it out as much as you love taking it. Well all right then. Either way, the ass-beating is just beginning. But now it’s over with for tonight. Take off all your clothes and get in bed.”

Finally! My heart soars at this, and I race to comply. But instead of following suit, Jennifer merely withdraws a pair of shiny steel handcuffs from her bag and follows me. Once I’m lying on my back in bed, she leans over and takes my entire prick into her mouth as easily as she did her hand.

She sucks hard on me, and my fantastic ecstasy at this first-ever experience is boundless. Her tongue tickles that oh-so sensitive underside, and then she bobs up and down, professionally fellating me until I’m gasping and groaning, clutching handfuls of satin sheet and hovering on the bare verge of ejaculating. Then she abruptly stops and orders me to roll over.

Mystified and cruelly denied, I comply. Straightaway she pulls my arms around behind my back and cuffs my wrist together.

“There!” she declares. “Your punishment for m**********g starts right now. You will never touch yourself again unless I allow it. These cuffs should keep you from indulging in any more filthy, forbidden activities. And as I recall, you used to beg me to put you in bondage. You enjoyed that even more than being beaten! So enjoy it now!”

What? I can’t believe this! She’s right, of course. But…but…

“But aren’t we going to have s*x?” I hear myself whine. “Aren’t you going to ‘relieve me of my virginity’?”

“Hell no!” Jen scoffs at this. “Leastwise not tonight. No, there will be no s*x for you, you dirty little boy. Instead, you’re going to lie here helpless all night and remember what used to happen to you when you really got dirty. I’ll be back for you tomorrow afternoon. You can make me dinner so start planning recipes. After all, how many times did I cook for you? Then later, we’ll relive some more old times. Until then, good-bye.”

I still can’t believe this! And yet, without another word, she turns her back on me and marches out the door, leaving me handcuffed, naked, amazingly erect, and incredibly horny. My raging-hot c**k is still cool and wet with her saliva, still tingling with the aftermath of sensations as heavenly as they were unprecedented.

Groaning with dismay, I begin squirming desperately against that slick satin sheet, rubbing my demanding erection as fervently against that soft warm waterbed as I ever did the cold concrete floor of the basement closet. Nothing can relieve my need however. Eventually, I even manage to straddle a big soft feather pillow; to lie atop it and hump like mad, pumping my hips and sliding my c**k against it while trying to imagine the slippery satin cover and delightfully yielding insides are really Jennifer’s cruelly denied v****a. Yet, not even this is enough to get me off, and at last I collapse in exhaustion, weeping in frustration, and feeling that tortured organ burn and throb like never before.