Note: This story was dynamically reformatted for online reading convenience. The Perks of Babysitting Mf, Mfff, inc, oral, anal ___________________________________________________________________________ _____ Chapter One: Monday To my continued shock and surprise, our first night together passed without so much as a hiccup. The girls swam until seven, splashing around in the pool while I did anything to keep myself from thinking about their wet, half-naked bodies floating around in the backyard. I called in pizza around seven and the waterlogged teenagers traipsed in, leaving a slick chlorine trail behind them as they ran upstairs to shower and change into their pajamas. I had resigned myself to the fact I was likely going to be cleaning up after my stepsister and her friends all week. Still, in spite of their messiness, the girls were being remarkably well behaved. Amy especially (who had grown a brattish streak along with her tits), was remarkably accommodating, even remembering her pleases and thank yous. I expected it was because my house had saved her from spending the week up on Grandma Ester's farm, churning butter and memorizing Bible verses. She probably knew I could have Ester down here in just two hours with a phone call, so she seemed to be behaving herself as best she could. Cassidy was, as she always was, a sweetheart who helped clear the table and throw away the demolished pizza boxes after dinner. I had no idea that three young women could destroy three pizzas so quickly, but teenagers had the appetite of teenagers, no matter what sex. We chatted by the dumpsters for a bit, about school, summer plans, and old teachers I still remembered. By the time we got back, Ashley had hijacked my gaming system, and was currently setting up a game of Rock Band with Amy on guitar. I played a few sets with them, opting to take over bass since no one else really wanted. But after the third replay of Carry On My Wayward Son, I had to pack it in (to cries of "pussy!" from Ashley behind the drum kit). Much as I would have liked to spend my Sunday night playing video games, I had to make an appearance at the tech company my firm was consulting to see how they were implementing our business plans. I went to bed Sunday night, optimistic that the week would be a normal one. I couldn't have been more wrong if I tried. ___________________________________________________________________________ ___ Monday morning came earlier than I wanted to, as I passed Cassidy on my way out at seven. She had always been something of a hippie so I wasn't surprised to see her drinking tea and meditating in the window seat when I came downstairs. I said I would be back by threeish and she sleepily bade me to have a good day. Needless to say, it was a promise I couldn't make. I spent all afternoon handling a business owner who couldn't understand why his business wasn't turning profit, despite the fact that he had recently purchased a second summer home in the Hamptons. There was a lot of shouting and "put your manager on the phone" thrown around and the only thing preventing me from reaching across the conference table and elbowing him in his face was the thought of payday coming Friday. So I smiled, nodded, and told him I would consult with my bosses before spitting on the ground on the way out just after four. I needed a drink and a long soak in the hot-tub; both at the same time if the girls weren't still living in my pool like a bunch of squatting ducks. But by the time I got home, I was surprised by the lack of laughing, screaming, and splashing by that had been a constant presence in my house for most of the summer. A brief glance around the living room and kitchen showed neither hide nor hair of the girls, and part of me rejoiced at having the house to myself for a little while. They probably had walked to the bus-stop or the shopping center a mile off. I could only hope that they had gone out to get pizza or meet some friends for the evening, and I had a few hours to unwind with a beer. Whistling at my newfound fortune, I opened the fridge, rifling around for a cold domestic beer as the door to the back yard slammed shut. "That for me?" Ashley's voice came from behind me, startling me into banging my head on one of the kitchen shelves. Ashley let out a sharp bark of laughter, toweling herself off as she stepped into the kitchen in a black bikini with a towel wrapped around her shoulder. "Where's the others?" I asked. "Nice to see you too," Ashley said with a tight smile. "They went to go shopping; I wanted to swim a little more...so, can I have that?" "Are you twenty-one?" I asked, cracking the beer open on the side of the counter and taking a long sip. "I'm almost sixteen," Ashley said, toweling her hair off, tossing the towel on the table, and leaning on the kitchen counter. I tried not to stare at the way her black thong hugged the contours of her thick, firm ass, but the way Ashley was leaning made it almost impossible. "You know, math wasn't always my strongest subject, but I think sixteen's a long way off from twenty one," I said, taking another sip as Ashley made a face. "Ugh, don't be a fucking prude," Ashley grumbled, pushing herself up onto the counter and crossing her firm, shapely legs in front of her. "It's not like I haven't had a beer before, you know." "I'm gonna tell your parents," I teased, laughing at the way her brilliant blue eyes rolled in the back of her head. "Oooh, I'm terrified," Ashley cried, holding her hands up as she slid off the counter. "Come on; one sip." "I'm not the most responsible person in the world, but I draw the line at feeding beer to fourteen year olds," I said, making my way towards the living room as Ashley chased me. "I've done worse, you know," Ashley huffed, chasing after me as I continued my trip towards my bedroom. "And I'm fifteen!" "Like what; weed?" I laughed, holding the bottle over my head as Ashley grabbed for it. "I don't care what your parents let you do when you're at home, but when you're staying with me-" My attempts at being a responsible adult were cut short as Ashley grabbed two fistfuls of my shirt, reaching up on her tiptoes and shoving her tongue in my mouth. I nearly dropped my beer, feeling her soft, pink tongue swirl over mine for a brief second, long enough to snatch the beer bottle from my hands before she pulled back. It took me a moment to overcome my surprise long enough to say, "What the fuck?" Ashley simply smiled secretively at me, taking a small sip from the beer with an approving nod as she turned to head up the stairs. I watched her go for a moment, hips swaying deliberately and ass sticking out with each step she climbed. Ashley paused at the top of the stairs, giving me a questioning glance before continuing down the hall towards my bedroom. As you can see, my metaphorical nuts were in a metaphorical vice. I could have done nothing and let a girl not old enough for her learner's permit close herself up in my room with a bottle of alcohol, or I could have followed her which, judging by her expression, seemed to be exactly what she wanted me to do in the first place. I lingered at the bottom of the stairs for a moment, before deciding to follow. "Ashley!" I called out, taking the stairs two at a time. I reached the top as she turned into my bedroom, shooting a teasing glance at me as she took another long sip of beer. I licked my lips, loosening my tie as I followed her into my bedroom. She was lying on my mattress when I got in there, flat on her belly with her legs kicking idly behind her as she nursed the beer I had been formerly drinking. "Give it to me," I said, traipsing over to her and holding out my hand. "Give what to you?" Ashley asked, eyebrows raising curiously. "You're going to have to be more specific." "Cut the shit; you know what I want," I said, hands on my hips as I stood in front of her. "Hmm...okay," Ashley said, holding out the half-empty bottle for me. "But you're gonna have to trade me something for it." "What the fuck are you talking abo-"I trailed off as her palm pressed against the bottom of my cock through my jeans, giving it a small squeeze as she looked up at me with an approving smile. "Nice," she said, fingers unbuckling my belt as she shimmied closer to the edge of the bed. "I can work with this." "What the fuck are you doing?" I hissed, stepping back a pace as my cock twitched in protest. "I'm sorry, is this the first time you've had a girl try and give you a blowjob before?" Ashley laughed, crawling off the bed and slithering towards me, scantily clad ass shaking with every step as she approached me. I was backed up against the desk, glancing down at Ashley as she knelt in front of me. "No wonder you broke up with your girlfriend." "She broke up with...you know what, that's not the point!" I said, batting her hand away as she reached for my zipper. "Ashley, you're half my age." "Not quite," she laughed, managing to unbutton my pants and tug my zipper down before I could stop her. "Come on; I said I owed you one for letting us crash here. Lemme pay you back." "Pay me back by not stealing my beer!" I hissed, hands bracing on the desk as Ashley tried to tug the front of my briefs down. "You can't do this?" "Can't I?" Ashley asked, again squeezing my quickly hardening cock through my underwear. I let out a small gasp, trying to keep my pulse from pounding out of my body. "Feels like you want me to...you didn't think I stayed behind because I wanted to swim, did you?" I should have known that someone like Ashley Derricks wouldn't have passed up an opportunity to go shopping for no good reason. Her wet, black hair clung to her neck and shoulders, pink lip between her teeth as she looked up at me with hungry brown eyes. "You can't be surprised," Ashley laughed. "You know I want you, right? And I always get the things I want." She took my stunned silence for compliance, tugging down the front of my briefs as my fully erect cock sprang to life in front of her. "Hell~o," Ashley purred, licking her lips as she settled on her knees in front of me. "What do we have here?" I wasn't exactly going to win any size contests, but eight-and a half long and one inch wide was probably a bigger cock than Ashley had ever seen in her life. She looked at it like a hungry dog stared at a bone, and for the first time I realized the depths of her infatuation with me. I had a beautiful, fit, fifteen year old who I had lusted after since her fourteenth birthday kneel between by legs, looking at my cock like it was a four course steak dinner. I can still remember the way the strand of saliva that dripped off her tongue as she looked up at me. Tell me you would have been strong enough to walk away. Tell me you could have said no when you thought that literally no one would have ever found out about it. I didn't care that I was being twisted around a teenager's little finger; I didn't care about anything except for the girl who looked like she had been waiting for this moment since puberty. "...fuck it," I groused, downing the rest of the beer in one gulp and looking down at her expectantly. If she was going to be this grabby with me all week, I figured it was better to get some of it out of her system. Besides, her perky little ass had been haunting my waking dreams and I needed some measure of relief. "Get to it, then." "Really?" Ashley said, raising her eyebrows in surprise. "Shit, what's with the one eighty?" "I decided to stop looking a gift horse in the mouth," I said, unbuttoning my shirt and peeling it off. I wasn't exactly in my college basketball shape, but I went to the gym regularly enough that Ashley took an approving glance over my bare stomach and chest. "Hey, I'm not complaining," Ashley said, reaching back and undoing the topknot holding her bikini top together. "I was ready to keep at this all week if you didn't give it up today." She shook her hair out, shimmying out of her top as her petite breasts came into view. I had never given her breasts much thought up until this point but now that I had a proper look at them, I had to admit they were pretty cute; still an A-Cup but with enough weight to bounce a little as she resettled in front of me. Ashley took deep breath, wetting her lips with her tongue as she reached out and kissed the tip of my hard, aching cock. The first wet pass of her tongue caused my legs to lock up, hands gripping the desk behind me as I panted through my nose. Ashley locked eyes with me as her lips parted, taking inch after inch of my cock in her mouth until she was about halfway down the shaft. I bit back a small snort of laughter as her cheeks bulged, tongue lapping at the bottom of my cock as she struggled to take more in. "Bit more than you can chew?" I teased as she pulled back for air. "Fuck you," Ashley snorted, squaring up to the tip of my penis again and pressing forward. She seemed to get deeper and deeper down onto my cock with every bob of her head, ardently determined to get as much of my prick in her hot, wet mouth as possible. My bedroom soon filled with obscene suckling and gulping sounds, as one of my little sister's best friends struggled to swallow every inch of me. I wish I had a camera that first time, just to capture the image of a fifteen year old punk slut hungrily devouring my cock, ass wiggling back and forth anxiously as she worked. Now and then she would come up for air, gasping as she kissed up and down the length of my shaft with hungry, suckling pants. It wasn't the finest or most refined blowjob I had ever received as Ashley seemed to be pulling out whatever trick she learned from porno to get me off. Still, the combination of Ashley's sloppy enthusiasm and her tight little jailbait body made it one of the most erotic experiences of my life. "Fuck, you're eager," I rasped, hand gripping the back of Ashley's hair and pulling her up as she gagged on my length. "You don't know what kind of pencil dicks I've been practicing on," Ashley panted, spitting a wad of excess spit and pre-cum onto my floor. "If I had your measurements, I might have just stuck to practicing on cucumbers; you're fucking thick, dude." "Flatterer," I said, petting the top of her head as she gave a sticky, toothy grin up at me. In spite of her brattiness at times, Ashley was a serious cutie. After a moment's respite, Ashley settled back into position, slowly pushing her lips down inch after inch of my aching cock. The deeper she got, the more she seemed to be struggling to take me in her tight teenie throat, but she was nothing if not determined. She pushed on, cheeks bulging and eyes watering a little as she forced the last few inches into her mouth, nose burying in my crotch for a brief moment as she raised her hands in a victory pose. "Fuck yes!" Ashley cheered, pumping her fist as she came up for air. "Not bad for a first timer," I chuckled, hand on the back of her head as I lined her up again. "C'mon; finish what you started." "Who's eager n-oomph!" I pulled Ashley forward, watching her lips part instinctively as she bobbed her head up and down on my cock. I watched inch after inch of hard, slick meat disappear into her mouth, feeling her tongue loll along the bottom as her throat muscles milked my head for all it was worth. Water ran out of her eyes as she sucked me off, drool running down her chin and gagging every few strokes. I was concerned she was taking too much too fast, but I noticed that her right hand slipped down the front of her bathing suit, toying with herself as muffled moans vibrated along the length of my cock. It seemed the little bitch got off on being choked; a fact I resolved to file away for later. Lust can do strange things to people. Moral lines you might not have crossed get disregarded when the object of your most perverse fantasies tempts you to fall. I'm not a saint; no one graduates from an MBA program with their soul in tact. But in that moment, watching a girl I had known since preschool fight to get every inch of my dick in her mouth while fingering herself, I felt the faintest moral thread snap. Once you fuck a teenager's mouth, there was no unfucking it. And now that I had felt what her mouth was capable of, I wanted a bit more. "Need a hand with that?" I asked, tugging Ashley back as she took a deep gasp, breasts slick with her own saliva and heaving despite their petite size. Ashley followed my gaze back to the bed, rolling her eyes with a fond sigh as she slowly got to her feet. "Figures," she snorted, taking me by the hand and walking me over to the matters. "I know what you want...it's what every guy wants, isn't it?" "Can you blame us?" I asked, watching her hips sway deliberately as she bent over the side of my bed, tanned little ass sticking up for my enjoyment. "Not really," Ashley said, giggling as I tugged the strings holding her tiny thong up. I let out a small moan as I saw the faint white tan-lines her thong left behind, kneeling behind her and taking each cheek in hand. "I have to admit, I've been saving my v-card for a special occasion." "No way you're a virgin," I chuckled, earning an offended glare from the girl leaning over my bed. "The fuck is that supposed to mean?" Ashley sniffed, gasping as my tongue pressed against her hot, wet slit. As something of a connoisseur of cunnilingus, I wasn't going to pass up an opportunity to feast on prime fifteen year old puss. What thrilled me more was that the fuckwits she had been sucking off probably didn't return the favor, watching her wiggle, squirm, and gasp as I ate her out from behind, thick juicy ass pressed against my cheeks as I did. "On second thought, maybe you are new to this?" I chuckled, sliding a finger inside her with remarkable ease. "Bet no one's touched you like this before, have they?" "N-no," Ashley stammered, hands clenching the bedspread. "Figures," I laughed, smacking her lightly on the ass as I got to my feet. She yelped, going up on the balls of her toes and swaying her hips from side to side as I rested my hands on them. "Pencil dicked little boys will always let you down." "Have you fucked enough to know?" Ashley snickered. "Smartass," I growled, hands slowly parting her tight little cheeks and running my tongue over my lips as her tight little asshole came into view. I considered for a moment fishing around for a bottle of lube and pounding little Ashley in her tightest little ass-et. But her warm, wet, dripping cunt lay just a few inches down, almost beckoning me in. "You sure you want this?" I stammered, bracing my hands on the sides of her hips as I lined up the tip of my cockhead with her waiting little pussy. Ashley just looked over her shoulder with a hungry little smirk, pressing her ass against my crotch and slowly shimmying it back and forth. "Do I need to make it more obvious?" Ashley asked, arching her back to get a look at my prick as I pressed it against her moist folds. I took a deep breath as something in the back of my mind told me this was a mistake; that I should throw her out as quickly as possible and pretend I hadn't just asked her to deepthroat my cock. There was no such thing as light statutory rape, and if I was in for a penny, I might as well have been in for a pound. Slowly, I began to push forward. Ashley's mouth fell open in a silent gasp as I wiggled my head in, creeping forward inch after inch into her impossibly tight little snatch. I thought I wouldn't fit for a moment, panting as I struggled to get more of myself inside of her. Ashley covered her mouth, free hand balling in my sheets as her eyes screwed shut. She pressed back as much as she could, legs shaking as she tried once again to get my relatively mammoth cock inside her. "Fuuuuck," she groaned, head bowing as I gripped her hips for leverage. "God damnit, dude, you're fucking huge!" I couldn't exactly argue with that, the way her walls gripped and fought against the intrusion that was slowly slipping inside her every inch of the way. I nearly blew my load just getting inside her, grunting as my hands tightened their grip on her body. Still I pushed on, drawing more and more obscene sounds from my young partner as I slowly, deliberately deflowered her. "Jesus fucking Christ, you're splitting me apart!" Ashley laughed, more out of amazement than actual pain. She pushed back as much as she was able, sighing through her slightly parted lips as I passed the halfway mark. "Fuck, I'm gonna be walking funny tomorrow, aren't I?" "I-If you can walk at all," I panted, leaning over her petite body as I forced the last few inches in. "Someone's cocky," Ashley whimpered, angling her hips up to take the last few inches in. In spite of nearly being skewered by a bigger cock than she had ever seen, the girl still had the gumption to trash talk me. I'd be lying if I said that didn't compel me to push my hips forward the rest of the way, savoring the sensation of being totally hilted inside of her and the startled little moan she gave when I hit rock bottom. "Fuck, I didn't think you were gonna fit," Ashley chuckled, wiggling her hips back and forth as I struggled to catch my breath. "I-I think we both bit off more than we could chew," I sighed, hands gripping the bedspread as I struggled not to blow myself inside her so soon. "So-speak for yourself, dude," Ashley insisted, bucking her hips back up against mine. "Come on; I got an itch I gotta scratch." I bit my lip, desperately thinking over the ballbreaking day I had endured to get here as a means of keeping my cool. I steadied my shaking legs, taking a deep breath as I began the torturous journey back out. Ashley fought every inch as I pulled back, squeezing and milking my prick like she would never get it again. I breathed hard, struggling to focus as I pulled everything but my cockhead out. I could see the sweat of exertion popping up on her back, feeling her shiver and hearing her moan as I pulled inch after inch out of her. I paused for a brief moment as I reached the peak of my thrust, taking a moment to squeeze her wonderfully tight little ass before driving forward again. Slowly, bit by bit, I managed to pick up the pace. I was glad the house was empty, as Ashley was anything but a quiet lover. She almost screamed when I hit her cervix again, head pressed against the comforter as she struggled to keep up her end of the work. But a virgin was a virgin, no matter how big she talked. There was only so much a young girl could do when experiencing her first cock, most of which was limited to panting, whimpering, and moaning while her unplowed pussy was used for the first time. As for me...well, nothing really describes the feeling. I can't put into words what it felt like, carnally using a cute little teenie bopper that had been a teasing little brat for years. The pleasure was so much more than just the physical; there was a visceral and satisfying emotional aspect to seeing one of the town's biggest brats lying under me, naked as a jaybird and swearing as I fucked her pussy bareback. I can't tell you how it felt to finally spear that little slut after dealing with her wantonness since she got her tits in. All the teasing, all they pouting, all the foot stamping tantrums were being paid back tenfold. After not getting laid for nearly a year, I had ended one of the shittiest workdays of my life with a cold domestic stout and hot teen cunt bouncing on my dick. Ecstatic didn't even begin to cover it; this was satisfying so many of my basic human needs at the same time I felt like I was fucking floating. "Y-You're fucking loving this, aren't you?" Ashley panted, looking over her shoulder as I began fucking her hard enough to make her perky little tits jiggle. "You like fucking this little teenage pussy, don't you?" I couldn't respond in anything more coherent than a grunt, fisting my hands in the sheets on either side of her hip as I shortened and sped up my thrusts. "Fucking perv," Ashley panted, nails digging into the backs of my hands as the bed began to rock. "Getting your rocks off in fifteen year old pussy. Bet your last girlfriend didn't give you pussy this good, did she? Bet she wasn't as tight as I am, was she?" Ashley pushed her back up against my chest, rocking her hips back and forth as I rode the little vixen into the mattress. "How does it feel knowing no man's ever been inside me before?" Ashley purred, tilting her head back and looking me in the eye as I got closer and closer to my climax. "Mm, yeah, fuck me just like that, baby. Work my little pussy just like that, stud. Make me a woman; make me-" Ashley trailed off with a wailing moan as her orgasm seemed to take her totally by surprise. The sound of her moaning my name as loud as she could, panting `yes yes yes!' over and over as she convulsed around my shaft pushed me over the edge. With a low grunt, I came harder than I remember ever cumming before in my life. My vision went white, my legs nearly gave out from under me, my hands clutched at Ashley's as I pumped load after load into her warm, waiting pussy. I came back to reality as Ashley giggled underneath me. I rolled over onto the bed, cock slipping out of her with a wet pop as Ashley rolled on her back, hands crossed over her stomach and staring up at the ceiling with a dreamy smile. "Jesus," Ashley panted after a minute. "I wouldn't have fucked around with the boys in freshman year if I knew you were this good..." I nodded mutely, still too boneless to do anything but stare at the ceiling and contemplate what had just happened. I was dimly aware of Ashley sitting up, glancing over to her as her fingers dabbed at the steady stream of cum that leaked out of her sopping pussy onto the mattress. "Shit, you really let me have it, didn't you?" Ashley laughed, smearing her fingers on my chest and standing up, steadying herself on the bed as her legs wobbled slightly. "Don't sweat; I've been on killer birth control since middle school?" She met my questioning glance with a laugh, wiping the hair out of her eyes as she bent over to pick up her thong. "Periods are a bitch, man," Ashley said, tying her thong back on her hips as I pushed myself into a sitting position. "Ashley," I said, still reeling from the feeling of being inside her. "This was...this can't happen again." Ashley laughed, turning back to me with a small smirk as she refastened her bikini top around her chest. "It will though." "I'm serious," I said, watching Ashley black thong darken as more of my cum leaked out of her. "Ashley this was-" "Just the beginning," Ashley said, turning to face me with a devilish smirk. "Unless you want me to tell my dad what happened in here?" I paled, the thought of Ashley's Marine father finding out draining the blood from my face as the door opened downstairs. Ashley turned, padding out of the bedroom and lingering in the doorway. "See you tonight," Ashley giggled, waving as I sat on my bed, naked and for the first time understanding just how fucked I was. I couldn't have known then that Ashley was right; this was all just the beginning of a long, and torrid affair. _____ AN: Hmm, should I continue?