Sins of the Sitter

Chapter 1: Reunion My name is Boynton. And f**k me; I’m so excited I can’t sit still! I keep roaming from room to room, checking to make sure nothing is amiss in this ridiculously big house. Meanwhile I’m constantly peering out the windows at the even more lavish mansion across the street. f**k me again; I can’t believe I’ve actually got a date tonight with my incredibly hot neighbor. First off, Jen’s a polished and sophisticated twenty-four. I’m a mere bumbling and naïve eighteen. Before today, we hadn’t even seen each other in over six years. But before that, we spent a lot of time together. As my next door neighbor, Jen served as my babysitter for over half a decade. From the ages of six and twelve and twelve and eighteen respectively, she was recruited by my parents to watch over me whenever they went out – which they did almost every day and night. Of course, as multi-millionaires, my parents could have hired a nanny to watch over their only child. And as the only daughter of multi-millionaires, Jennifer Johnson had no need of the relative pittance she was paid. But the Boyntons didn’t get rich by wasting money. And the thought it good for Jen to develop some responsibility as she grew up. In the coolest serendipity, it worked out perfectly. I was in awe of this big, beautiful older girl. And she enjoyed having a lonely little boy to lord it over. By the time I was eight, I was hopelessly enthralled. I was absolutely crushed when she finally moved out of state to attend college. For the next six years, when most junior high and high school students were busy feeling out (and up) the opposite s*x, I didn’t have a single date. Jen had spoiled me for girls my own age. And as a short, slight kid lacking in social skills, the only girls I could’ve had would’ve been equally undesirable. Forget about it, my standards were just too high. I graduated high school a virgin who’d never been kissed. And so I’ve remained, despite my suddenly outrageous wealth. Not three months ago, my parents died in a plane crash, leaving me their sole heir. Holy s**t, the house and property were mine, along with a bewildering array of investments and more bank accounts than I could count. Okay, I admit it, I was less than crushed. My parents were always distant, even neglectful of me, practically leaving me to be raised by my neighbor. With them out of the picture, I didn’t have to worry about college, becoming another money grubber, or even working a day of my life. Sounds like Xanadu, right? Unfortunately, I shortly found myself lonelier than ever, rattling around an enormous house day after day with only the occasional domestic help for company. But then wonder of wonders, glory of glories, from out of the blue suddenly struck more good fortune. Mr. and Mrs. Johnson, now getting on quite a bit, decided to retire to somewhere in the Caribbean. You know, some place they could run out the clock on a sun-soaked, tax-exempt beach. Good for them. But how much better for me! Their impossibly lovely daughter, having recently received her Master’s degree, apparently decided to return from school and take up residence in the empty family home. The mailman told me. But I didn’t dare believe it until I looked out my bedroom window this morning. Holy s**t, there she was, sunbathing on her huge front lawn. We both have very long driveways. So the distance was considerable. But the master bedroom which I’ve lately taken over is on the second floor, and I had the advantage of height. And f**k me, there was no mistaking that distinctive hair: full and thick and impossibly glossy, black as a raven’s wing. It even appeared to be longer than when I’d last seen it, hanging down to brush the bra strap just visible across her still damp T-shirted back as she walked out the bedroom door. And her amazing body was immediately unmistakable as well. Jen is a really big girl, fully eight inches taller than my pathetic little five foot seven. And she’s really f*****g big in every other respect. I don’t mean fat now – perish the thought! But she is BIG-boned, solidly built, thick in the arms and legs and body, with bulked-up shoulders, bulging biceps and breasts that still somehow outsize the rest. And holy s**t, didn’t she appear to be topless as she reclined in her lounger, just out of range of the sprinklers? My heart was pounding as I raced to the closet and dug out my binoculars. I returned to the window, prick rising in anticipation. I focused in and gave an impossible moan of appreciation. Jen was not just topless, she was entirely nude. And her huge, beautifully natural breasts surpassed anything to be found in my extensive porno collection. They even put my maddest fantasies to shame. I stood there studying her for nearly an hour until she finally rose and slipped back into her robe. I swear she glanced directly at me a second, grinning up a bit at the high window where I hid. Then she turned and went inside. Naturally I went straight to bed. Utterly captivated, I shucked off my pajamas and frantically m*********d. That vision of divine loveliness playing across my eyelids was so compelling that I couldn’t have waited for the world to end. I achieved the climax of my life in under a minute. Spunk pumped out of me like a gusher, emptying me comprehensively. Still I thrashed and spasmed like an electrocuted epileptic. At last I lay there spent, panting and gasping and feeling incomparably blessed. Then I began scheming out ways to renew my nefarious neighbor’s acquaintance. *** Like any good soldier with an impossible obstacle to surmount, I concentrated first on preparation and surveillance. I washed and dressed myself like never before, shaved and carefully splashed on the old cologne. Then I alternated between checking every square centimeter of the house and using my binoculars to keep a close watch on the Johnson’s – just as I would oh so obsessively do for the rest of the day. And, at last, my opportunity presented itself. About three in the afternoon, the mailman’s jeep made its slow way around the cul-de-sac that forms the end of our secluded suburban street. And once he’d passed Jen’s box on the way to mine, I saw her front door open. The lady of my dreams emerged wearing only skimpy white shorts and a tightly stretched, dark blue tube top. I stowed the binocs, raced downstairs, and then commenced a perfectly timed yet seemly nonchalant stroll out to my own mailbox. Naturally, through my calculations, hers, or both, I arrived on the opposite side of the turnabout just as she was emptying her receptacle. She looked up then, feigning surprise at my arrival, and greeted me with a beaming smile that could never have been more genuine. “ny! I was counting on you still being around! How are you doing?” She crossed the road toward me. Holding her mail in one hand, she engulfed me in a strong, smothering hug before I could even reply. Squashing me against her breasts, she actually lifted me off my feet, crackling my spine, and bruising my ribs before setting me back down. I was still gasping for breath and scrambling for my oft-rehearsed greeting when she spared me the necessity. “Look at you! My little ward is all grown up – sort of!” She loomed up close, grinning down at me. “You’re a rather pretty young man now, aren’t you? But you’re still a shrimpy little wimpy one!” “I…I…I guess so, Jenny,” I stammered, utterly intimidated by her size, proximity, and our rather intense history. But the second I looked at her feet, she put her fingers under my chin and tipped my gaze back up to meet hers. “Don’t worry, ny. I remember you best as the ashamed, lonely little boy enthralled by his beautiful babysitter’s superior femininity. And that’s the way I shall always love you. So let’s catch up now, my obsessed little neighbor. What have you been doing with yourself all these years?” Intimidated even more, I cowered under her mocking regard and admitted the shameful truth. “Nothing at all, really. Just finishing up school. You know me. I was never much good at making friends, much less scoring dates. And then my parents died, leaving me the house and everything. I don’t need to work, nor do I feel like it. But since then, I’ve been lonelier than ever.” “I heard about your parents. I’m sorry.” “Don’t be. They were inattentive pricks. You were more of a parent to me than they ever were.” Jen grinned again at this. “Yes, I was, wasn’t I?” She continued to grin unsettlingly at me, and I found myself fumbling around for a topic of conversation. And naturally my most desperate wish emerged from my lips. “So are you back to stay or what?” “I sure am!” she exclaimed, still favoring me with a knowing, laughing look in her eye as I squirmed in her shadow. “My parents retired and moved out, leaving me the house. I’ve finished my Master’s in Feminist Issues. But I have no more need or inclination to go to work than you do. Hell, babysitting you was the only job I’ve ever had or probably ever will. So you can definitely say I’m back here to stay, neighbor.” “That’s so wonderful!” I gushed. “Oh, Jen, you know I’ve always been hopelessly in love with you. Seeing you again now is the best thing that’s ever happened to me!” “You mean seeing me naked this morning was the best thing that’s ever happened to you!” she smirked. “I saw the lens flash from your binoculars at least a dozen times, ny. I know you were spying on me, you naughty boy! I’ve got a good mind to put you over my knee, just like in the old days!” Immediately mortified, and yet inexplicably turned on by this, I could only stammer, blush, and look at my shoes. “You jerked off while you did it too, didn’t you?” My humiliation quadrupled at this accurate accusation. Yet, I’d never been able to lie to Jennifer. Somehow I managed to nod, still looking down at the ground. “I’m desperately sorry, Jen. But I just couldn’t help myself. You’re the first naked lady I’ve ever seen – the first real one, anyways. And I love and desire and missed you so damn much.” Jen gave a gloating laugh at this. “Well, little ny, maybe I’ll just have to make your dreams come true and relieve you of your silly virginity one of these days. I think we are going to be very close from now on, closer even than when we were kids. Why don’t we go out for drinks tonight? We’ll relive some old times.” Naturally I was both astounded and ecstatic at this prospect. Somehow I managed to close my dropped jaw and look back up at her at last. Her brilliant blue eyes – always so wonderfully bright in contrast to her raven-black hair – still held a definite mocking glint. And, as always, her beauty and superiority practically paralyzed me. But, nevertheless, I managed to scramble up a bit of craft. “Um…well…I’m not old enough to legally drink yet. But my parents left a fully stocked bar and hundreds of DVDs. Why don’t you come over and watch a movie tonight? We’ll order a pizza or something too.” “Excellent!” Jen exclaimed. “I’ll be there after dark. See you then.” My head swimming with all this, I turned to head back up my driveway, only to be stopped by another mocking laugh from my neighbor. “Say, ny, don’t you think you ought to check your mailbox? That is why you came out here, isn’t it?” “Oh, yeah,” I muttered, and opened the box. And, of course, the only thing in there was this month’s issue of Playboy. “Pornography!” cried Jen immediately. “Oh, you really are a bad boy! You’re going over my lap for sure now!” And with that, she gave me a playful swat across the ass, turned, and headed back up her own driveway. I stood and watched her go for a minute. Then, face burning, gut churning, and my c**k a hot little rock against my pocket, I made my own dazed way back up to the house. *** So anyway, the rest of this day has passed impossibly slowly. But now, just as I’ve completed one last restless circuit of the house, the doorbell rings. I’m currently at the bar – there are two of them actually, one in the downstairs living room and one in the master bedroom. I’ve chosen the latter for entertaining my beloved, and not just because my new bedroom has the best entertainment center and houses the DVD collection. I’m hoping the proximity of that enormous waterbed will facilitate things a bit. Could it really happen? Could tonight finally be the night? Was Jennifer really serious? The thought of finally losing my virginity, and to the only woman I’ve ever considered worthy of giving it up to, has had me in an anticipatory tizzy ever since we parted earlier. Now my system responds to the sound of chiming by kicking my heart rate into overdrive and setting swarms of butterflies loose in my belly. Immediately, I race down the stairs and over to the front door. I take a second to collect myself and pull it open. Then, for the second time today, my jaw drops open although this time it’s as much in unaffected admiration as astonishment. Surely this towering apparition can’t be real. She must be a wet dream come to life, or a gloriously vengeful goddess come down to Earth to collect the souls of her chosen sinners. Her incredible beauty and intimidating size are immensely accentuated by an absolutely smashing black leather outfit. To start with, her hair has been curled just enough to make it even more alluring. Her make-up job is minimal yet perfectly applied. Yet that’s but the bare beginning. Her pointy-toed, stiletto-heeled boots give her nearly a full foot of height on me, putting her incredible breasts at just the level of my shocked-wide eyes. Her pants are skin-tight and decorated with shiny steel spikes along the seams. Most amazing of all, those watermelon breasts are uplifted and only barely contained by a skimpy matching black leather silver-spiked brassiere. Otherwise, she wears only similarly matching spike-studded collars about her neck and biceps, and fingerless, knuckle-spiked gloves encase her big strong hands. A huge, sparkling diamond stud decorates her otherwise completely bare belly, and inch-long silver scimitars dangle from her earlobes. Taken in all at once, this impossibly arousing ensemble is as fearsome as it is unprecedented. Never have I ever seen any woman dressed thus, much less my completely familiar yet never mundane girl-next-door. I can only stand there and goggle up her while Jen smiles grimly down at me, reveling in my appalled, awestruck arousal. She gives me nearly a full minute to appreciate her incredibly intimidating appearance. Then she barges in uninvited. Stepping right up to me, she blatantly invades my personal space. The bare upper slopes of her leather-clad breasts brush my nose; and, without a word, she reaches down and boldly gropes my crotch. Feeling my throbbing erection, she finally deigns to speak to me. “Look how hard you are!” she breathes down. “College has made a whole new woman out of your babysitter, hasn’t it? Or maybe it just finally fully unleashed a potential your childhood spent under my power certainly helped develop. “In any case, beginning tonight, we’re going to set about exploring that mutual potential to the very fullest. Now get me a f*****g drink, boy! I want a double bourbon on the rocks!” “Yes, ma’am,” I manage, the honorific issuing from me unbidden. I’m immediately unmanned and continue as obsequiously as I can. “If you’ll come with me, I’ll take you to the bar, DVD collection, and a fifty-eight inch high-definition plasma-screen TV.” “Good boy,” my hulking neighbor purrs. Then she follows so close behind me I swear I can feel her breathing down the back of my neck as we mount the stairs and make our way to the master bedroom. Once there she moves immediately to the couch I’d placed before the TV. She opens a small black handbag, lights up a joint, and picks up the list I’d printed out detailing the entire inventory of the DVDs that I’d either acquired or inherited. Meanwhile, I go to the bar and pour us a pair of Wild Turkeys. Normally, I don’t drink hard liquor – there’s also a keg of Beck’s Dark on tap and that usually suits me. But given my former babysitter’s intimidating new appearance and attitude – which I’m now forced to admit was quite more than hinted at in her earlier incarnation as the only true authority in my life – I feel it’s best to ingratiate myself with her as much as possible. I return, bringing the bottle and ice bucket with me. I set them down, serve her whiskey, and right away she points out a title on the sheet. “There: Aliens. The extended director’s cut. We’ll watch that.” Dutifully, I retrieve the disk, insert it, and begin playback. Then I take my drink and join her on the couch, careful to leave a respectful space between us. Jen, however, has other ideas. “Scoot over here, ny. I won’t bite. At least not yet…” I obey and right away she wraps a big strong arm about my shoulders. She pulls me up tight against her, my short, slight form dwarfed by her big voluptuous one. “Now keep quiet,” she orders. “This is one of my favorite movies, and I’ve never seen the extended version. I don’t want to miss anything.” I sit and remain dutifully silent, utterly blown away to be enfolded so by this huge, gorgeous older woman. Her left breast is squashed against my shoulder, her body is oh-so big and warm, and the heady female smell of her is indescribably delicious. As sexually, romantically, and even human contact-deprived as I’ve always been, Jen has me in heaven already. I work steadily on my drink and make no demurral as she periodically freshens us both up, even though her body weight, experience, and overall tolerance dwarf mine. Then as the film progresses, and Sigourney Weaver’s Ripley character develops from an unsure peripheral role into an aggressive, dominating force and, finally, into an absolutely iconic action-movie protagonist, the similarly powerful female sitting next to me can’t help but violate her own order. Ever more emphatically, she extols Ripley’s perfect combination of motherly nurturing and ass-kicking aggression. “Look at her! She makes the entire squad of highly-trained male soldiers look like p***y little wimps! The only one who can hold a candle to her is the only other female in the cast: the buffed-up Vasquez, who wields the biggest weapon and is the platoon’s most effective soldier. And, of course, the two men who are supposed to be in authority are the weakest links of all: the incompetent, ineffectual lieutenant and the treacherous, effeminate company man. God, I love this movie! It’s the one mainstream sci-fi action franchise that tells it like it is: with the women properly dominant and the males exposed as the weak, limited creatures they are!” She goes on and on in this vein, more and more exposing and alluding to the radically feminist indoctrination she’s received while away at college. This is both unsettling and arousing to me, and ever more the latter as I get drunker. Self-deluding barriers begin to break down, and I’m force to recognize that it’s the air of superiority she’s had over me from a very impressionable age, more than her will-sapping beauty and monolithic size, that form the keystone of my attraction to her. Still, it’s a little scary hearing her scathing talk and wondering what other radical new attitudes and appetites her years at college have unleashed in her. As unbearably horny as I am, and desperate to finally have s*x with this icon of aggressive femininity, even being increasingly drunk isn’t enough to give me the courage to make the first move on her. As weak and insecure as the stereotypical male she constantly derides, I slump quietly against her, clutched in her one-armed embrace and quietly waiting to follow whatever lead she takes. Then finally the movie ends, and the evening’s real entertainment gets underway. Ripley slays the monster, adopts the child fate has placed in her care, and the credits roll. My erstwhile babysitter squeezes me even tighter against her soft warm side then, and sighs with exquisite satisfaction. “That was so spectacular. That movie never fails to fire me up. Thank you for the invitation tonight, ny, and for having the wherewithal to indulge my rather particular tastes. I’m most pleased with you right now.” Naturally, my heart soars with this, and I burrow ever deeper into her big warm flank. But then her voice and manner suddenly harden. “However, that doesn’t mean I’ve forgotten about your absolutely necessary punishment! On the contrary, it just makes me that much more determined and excited about delivering it. “You know that you were a very bad boy this morning, iel. We absolutely have to relive some old times in response. There is no alternative. So now I’m going to give you a very hard, extended, good old-fashioned bare-assed butt-spanking, just like I used to. Any objections, boy?” And there it is at last, the key to everything that’s been driving me tonight. In the few brief seconds before I respond, I’m cast back twelve full years into the past to relive those crucially formative times in my mind.