Sins of the Sitter

Excerpt

“Well, Daniel?”

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 cock 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 need even 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 sex 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 cock 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 flushed face 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 shit 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. The 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 masturbating 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 sex?” 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 sex 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 cock 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 cock against it while trying to imagine the slippery satin cover and delightfully yielding insides are really Jennifer’s cruelly denied vagina. 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.

For the rest of the night I writhe and struggle fruitlessly, rattling my shackles and re-acquainting myself with the perverse thrill of bondage. But now that I’m an adult I finally realize what incomprehensible apotheosis my prepubescent body was endlessly striving toward in those days. And knowing this, and knowing the impossibility of achieving it while bound, turns all of that former yearning and craving into ever more maddening frustration. For hours unending I struggle and weep, rubbing my cock on the sheet and humping that big slick soft pillow like an alcoholic worrying at an un-open-able whiskey bottle. It’s not until dawn is breaking that I finally exhaust myself enough to remember Jennifer’s final order.

What did happen when I used to really get dirty? Soon enough I understand. And again the floodgates of memory are flung open.