BABYSITTING BENEFITS free porn video

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Babysitting BenefitsbyVelius Ironhorn©
Here's a true story. Or is it? Names have been changed for the sake of propriety, but it's pretty damn close to true events. Unless it's not, then names haven't been changed. Alas, I've already gone off on a tangent. Don't let the title throw you, the actual participants are of legal age.

So, let me start off on a downer. My mom passed away last year. Just one moment in a long line of stressful events for my family. Without getting too much into it, my parents were separated and in the process of divorce when it happened. The tension has been pretty bad, especially since my father is such a pain in the ass. He's one of those cranky old curmudgeons that always needs something to complain about, which is part of why my mother left him.

I currently live in a tiny house with three other miserable bachelors. It's cramped--barely enough for two people--and up until now, I've avoided being caught jerking off to Internet porn by only the slimmest of margins. Here comes the real set up: Ever since then, everyone on my dad's side of the family have come out of the woodwork with their sympathy-driven holiday invites and whatnot. They're good folks, but I'm not much of a people person. However, it did create the opportunity for this titillating tale.

Cut to: An unseasonably warm weekend in early Spring. I get a call from Aunt Marlene, who asks if I'm for babysitting duty. She and her husband Bill were planning a cut/paste romantic dinner and their normal sitter couldn't make it.

Meanwhile, their eldest daughter Roxanne would be going out with friends immediately after work to celebrate early her eighteenth birthday coming tomorrow. That means their rambunctious youngest daughter Kerry would need some supervision for the evening. You've already heard enough about me to understand how I would appreciate any opportunity to get out of the house. The chump change they're offering doesn't interest me, but I accept all the same. I hop in my Ford P.O.S. and drive over to their place in record time.

Kerry's a affable k**. She's a total tomboy and more of a geek then me. I get there and we spend the majority of the night eating pizza and playing video games. I can tell she's totally sweet on me, but this story isn't about her. Which is a good thing, because she's way young for this crap and I don't want to get arrested. She could be pretty smokin' in a few years, but I digress.

The grandfather clock downstairs chimes eleven and we're already two hours past her bedtime. I've got no idea how frisky her folks are feeling tonight, so I figure we ought to pack it in before they come home and I lose my cursory twenty bucks. We have one last deathmatch for the road and I drag her reluctantly into bed. Once she's settled, I exit and close the bedroom door, on the back of which is a poster her dream boy, Gary Sinise.

Ah, blissful silence.

The only thing that keeps me from geeking out completely is a delicate constitution. I need to eat real food once in a while, so no living on instant ramen and Mountain Dew. Hours of loud techno music and rhythmic explosions give me a headache. Now that the night's fun was over (or so I thought), I set up my laptop on the dining room table and started pecking away at my latest attempt at erotic literature.

Maybe that's when I started writing this very story. Or did I just blow your mind?

I'm getting pretty into it. You know that mental place where the words flow unheeded? I was there, man. Sweaty, short of breath, pitching a tent as I write the juicy parts. Mmmmmm, juicy parts... To avoid reaching into my pants while I write, I force myself to break away and go raid Uncle Bill's liquor cabinet. Nothing takes the edge off like a whiskey on the rocks. Even as I mix, I'm thinking about the next lurid sex act.

I was so into it that I didn't hear the clicking from down the hall that meant the front door had been opened. I come back into the dining room and Roxanne is leaning over my chair, peeking at my latest masterpiece-in-progress. My sweet foxy Roxy. Oh yeah, she's the subject of this story.

I remember playing tag with a midget in a pink tutu while all the adults thanked me for keeping the young'uns occupied. Roxanne has filled out nicely since then. She's now a half-head shorter than me, which is pretty impressive considering how tall I am. Thick brown hair almost as dark as mine is matted around her neck and shoulders, greasy from working in a Friday's-like restaurant kitchen followed by a night of dancing with her girlfriends. Dark eyes glitter in the dining room's low light and her pouty lips are turned up at the corners ever so slightly, clearly amused by what I was in the middle of writing. But it's not her expression that catches my eye first.

Roxy still has a bit of baby fat, so she's got some thick curves and waistband bulges that most guys in my neighborhood would be turned off by. Me, I've never been into the skinny l****a types and I think Roxy's full figure is positively bodacious. She's still wearing the tight belly shirt uniform with a generic restaurant name glittering across her double-dees. Her arms are folded on the back of the chair, generous bust hanging over them. There's a sparkle of silver at her throat. Roxy's favorite necklace pendant--a 'male' symbol sold as a promotional item for a certain spy movie spoof--points down into her cleavage like a signpost to paradise.

The old soldier is standing at attention, saluting that sweet land of liberty.

Now I've got two problems. She hasn't yet noticed my embarrassing situation, but she is about to reach the story's climax, no pun intended. I can only prevent one from happening. Taking a chance, I trip over the power cord and pull it out. Like clockwork, my crappy old laptop crashes because I'm too cheap to buy one with a decent battery. The sting of knowing I forgot to save my work and will never be able to rewrite all that as good the second time is tempered by the look of disappointment on her face. Gretzky shoots, Jesus saves!

Roxanne looks up at me and I make a show of trying not to spill my drink. It draws her gaze away from the deep shadows my crotch is casting, or so I hope. Her smirk turns into a sneer. "What are you doing here?" she asks.

Did I forgot to mention that puberty made her kind of a bitch too?

"Sorry, ma'am. That information is on a strict need-to-know basis."

She huffs in mock exasperation and her bosom jiggles impressively. "Um, hello? It's my house."

"Not for much longer. I claim this dining room for Mother Russia!" I punctuate the statement by slamming my drink down on the table, splashing the sharp tonic across it. I resist the urge to see if it smokes on the hardwood like in those old Westerns.

"Whatever!" she replies with a convincing valley girl accent, despite the only valley of significant size within ten miles being down her shirt. Roxy brushes past me and heads for the stairs to the bedrooms. "You better clean that up."

"I only take orders from the Kremlin."

Her emphatic reply--"You are such a weirdo"--wafts down from the second story. As I wipe the table with a dish rag, I silently thank that the muse of comedy has seen fit to grant me a sense of humor when it really counts. I track the dull padding of her feet as she walks around her room, then down the hall, and into the bathroom. There is the muffled squeaking of pipes as she turns on the water and steps into the shower. I try not to think about her voluptuous body, wet and soapy...

Trying not to think about it.

After booting up my poor laptop to make sure no serious damage was incurred, I shut it down for good and pack it away. No sense testing fate.

One of the best features of Bill and Marlene's house is the living room. A plush corduroy couch runs the length of the front picture window and makes a right angle across from the entrance. Bill's big screen TV is perfect for watching sporting events, hi-def DVDs, or import Asian porno. But I'm not so stupid as to test it out for that last option. He's got satellite too, so there are several hundred channels of nothing just ripe for the surfing. By the time I hear Roxanne's footfalls crossing back to her room, I've settled on a subtitled kung fu movie on the international channel.

I'm sure it's been a busy night for Roxy and I expected our discourse to end where it did, so imagine my surprise when a round-bottomed goddess descends the stairs in her evening finery: pajama pants and a white tank top that does a marginally better job of concealing her womanly curves than the belly shirt did. Hair previously slick with sweat is now buoyant and luxurious, shining in the flicker of the television. She crosses the room towards me and nonchalantly plops into my lap. She's been doing that for years, probably because she thinks it annoys me. On the contrary, by no means is it an unpleasant position to be in, but Roxanne isn't the small girl she used to be.

My comment as to the nature of her weight comes out as a whoosh of breath. "You're getting a little big for this, don't you think?" I groan, internally begging her not to get up. Her butt may be a little on the big side, but it feels great through the thin fabric.

"Shut up," Roxy snaps, jabbing me in the ribs. But she doesn't move, except to pluck my whiskey from the coffee table. She brings the glass to her full lips and takes a sip, then makes the classic 'whiskey face'. "You drink this piss?" she asks incredulously. That doesn't stop her from taking another sip.

I risk snaking an arm around her middle. "And so do you, apparently." I snatch the glass out of her hand and drown it before I'm caught with an inebriated minor. "Whiskey is a man's drink, girly. It'll put hair on your chest."

Shock crosses Roxanne's face and she pulls open the front of her tank top. She's not wearing a bra and I swear I see a flash of nipple, but I resist the temptation and laugh at her gullibility. Roxy jabs me again and crawls away, giving me a nice view of her shapely rear. She settles into the corner of the couch and drops her bare feet in my lap.

"I've been standing all day. Give me a foot massage," she commands with the air of a princess.

Feet may not be on my personal list of fetishes, but the mood is right. Roxy crosses her ankles; while I massage her right foot, her left heel inadvertently digs into my groin. Out of the corner of my eye, I see she's pulled up her shirt and is absent-mindedly fingering the navel ring she convinced her parents to let her get for her sixteenth birthday.

Sergeant Johnson returns for a second tour of duty. "You gonna reciprocate?" I joke, wondering if she realizes how she's influencing my physiology.

Roxy snorts at me, but her eyes remain glued to the television. The Red Tiger is about to get revenge against Master Dragon Claw for his grandfather's murder. Emboldened by her lack of attention, I start to work my magic fingers.

Truth be told, I'm no great catch. I'm extraordinarily average of build, perhaps a little heavy around the middle, with a plain face. Hooking a women may be the hard part, but I can reel 'em in. Chicks dig a tortured artist. When it comes to th bedroom, most men are in it for themselves, their own personal gratification. I know what the ladies like and if they enjoy it, I do.

True to form, Roxanne begins to squirm. She twists the hem of her tank top around a finger. Stiffening nipples poke through the fabric. Her legs press together reflexively. My cousin utters a moan, then catches herself. She rolls on her side and tucks her legs up, pulling her feet from my grasp. I can almost see Roxy's face glowing red in the dark living room. It gets really quiet as the credits role.

"You have sex yet?" she asks suddenly.

I admit to being mildly offended by that particular phrasing. "You have to ask?"

"Well, I always had you pegged for the thirty-year-old virgin type," she counters, the sharpness returning to her tone.

"You wound me, dear cousin. To answer your question: Yeah, a couple times now." In the dim illumination of the television, I come to the conclusion that red hair is the only thing that could make Roxy any hotter than she already is. "What about you?"

There's no hesitance in her answer. "No. My boyfriend wants to, of course. But I don't think I want that...yet." She laughs ruefully. "Doesn't stop him from asking for blowjobs."

"Ever give it to him?"

"Only if he's gonna pay me back." Roxanne stops. It seems the similarity of our words has occurred to her as well.

"I'm always more than willing to go down," I offer by means of continuing this thread of dialogue. "Heck, sometimes that's the best part."

No response.

"Heh... Okay, this is an awkward silence." The corner of her mouth twitches, like she's trying to suppress a smile. "So, is it my turn?" I ask, kicking off my sneakers and presenting my smelly be-socked dogs to her.

Roxy laughs in spite of herself and throws a pillow at me. Tension breaking maneuver: successful. Grabbing the pillow, I pounce on her. Roxy's laughter creates ripples down her body, accentuating the fullness of her figure. Her undulations remind me of a woman in the throws of orgasm. I stop long enough to let her catch her breath, then my assault begins anew, teasing fingers searching out the most sensitive areas of her ribs and stomach. A squeal comes out of her that surely woke up the entire block.

We freeze. No sounds from outside. And more importantly, none from upstairs.

When it seems the coast in clear, Roxy makes another squeal, this time of irritation. She knees me in the gut and I collapse atop her. I can't possibly hide my erection as it now presses against her hip. Her loose bedclothes are disheveled. The weather's been so warm, I'm not wearing much either. From my vantage point with my chin nestled in her cleavage, I can look squarely into her face and see the conflict there. She's now dealing with the same clash of desire and reservation that I've felt towards her for years.

My eyes lock with hers. The next show comes on and it's a police procedural in syndication. Roxy's warm, shallow breaths have the bite of whiskey, despite how little she drank, and I know mine must be worse. The grandfather clock ticks away.

Roxanne's hands come up under my shirt, sliding across my broad back. That's all the incentive I need and I lean forward, her cute pout meeting my own lips. She may have admitted to being a virgin, but is clearly no amateur at the art of snogging. The drink we shared notwithstanding, she tastes like strawberries. Who wears lip gloss to bed? Was she hoping for the same thing I was? The possibility runs through my head and excites me all the more.

Her hands come up through the neck of my shirt and she runs her fingers through my close-cropped hair. Roxy just hit the sweet spot. You guys know what I'm talking about. Ladies, try it sometime. We like it. A lot.

I reach up under her tank top for the breasts that have been driving me crazy since they grew in like spring melons. Better than I could have imagined, the soft firmness of her flesh makes my fingers itch. They stretch, trying to encompass her voluptuous orbs entirely, which is impossible. They find her nipples and Roxy gasps against my mouth, her tongue searching for my own. She moans as I tease them, slowly circling the areolas with feather-light caresses. Roxy bites my lip in protest.

A spark of static passes between us as I manipulate the stiff nubs. Carefully stroking, pinching, twisting.

"God, I can't take it anymore!" comes her husky cry. Roxanne pushes me away and I watch as she draws her legs up to her chest and reaches for the waist of her pajamas. She yanks them down her hips and to her knees, exposing herself to me. It's dark, but I can tell she's not wearing panties either. My cousin groans as she tries to grind against the pole in my pants, but I pull back. "What are you waiting for?" she demands.

I silence her with a finger on her lips and wait for the clock. It chimes once, twice, twelve times in all. I give the confused girl my winningest smile. "Happy Birthday, Roxanne. Welcome to the age of consent."

As I lower my head, Roxy pushes against the couch and raises her hips, now almost vertical in the effort to expedite my touch. I hold her hips steady and spread the hot meat of her thighs. She shivers at the feel of my spicy breath as I examine her. My cousin's womanly mound is mostly hairless. A few spots of darkness in the gloom indicate missed patches of stubble and I see a few fresh razor nicks. She shaved tonight, for me.

Grateful, I cease the teasing and dive in, taking the mound of her pubis into my hungry mouth. I suck on her young flesh, bathing her with my tongue. Roxy responds lustily as I dip into her womanhood, deeper with each push, longer with each stroke. It may sound cliche, but she taste's like honey. Her nectar is thick and creamy, sweet with her desire and flowing freely in the need for attention.

She moans again as I replace my tongue with probing fingers. They spread her wide, unfolding her delicate flower and caressing each petal with meticulous precision. Each finger is followed by another, filling her tight, virginal cavity. My kisses and licks over her skin gather up beads of sweat and juice, tickling her, enhancing the sensations that radiate through her body.

Parting the cheeks of her ass with my thumbs reveals the tight pink knot of her anus. I press my lips against it and feel the orifice tighten, then relax. Roxy does not protest. Softly at first, then with growing insistence, I introduce this oft under-appreciated erogenous zone to the gentle ministrations of my tongue. Her fingers dig into my denim covered legs as I encourage her anus to open itself to me. As she becomes accustomed to this new intrusion, I switch tactics again. My mouth returns to servicing her nether lips while a nectar-coated finger slowly inserts itself into her ass. She clenches reflexively, then eases up enough to allow a second finger to enter. They curl around, exploring the inner folds, finding the most secret sensitive spots.

Roxanne begins to pant and I know the time is right. Curling my tongue up inside her, I lash at the hard, hidden clitoris. Her thighs clamp down on either side of my head, threatening to smother me, but I do not relent. My sweet cousin has never before had the opportunity to experience such a coordinated attack on her most pleasurable regions and is unable to resist my technique for long. Roxy's whole body goes ramrod straight as she climaxes and she bites a knuckle to keep from screaming aloud; biting so hard that I worry she may draw blood. She begins to shake as the first wave passes, then melts onto the couch, shuddering rhythmically with subsequent jolts of orgasm.

Her eyes are glazed with contentment and she says nothing. I've never struck a woman speechless before and--even knowing it's more a product of her own inexperience than my expertise--I take it as a compliment. But now that her lust is slated, I become all too aware of my own predicament. Twice now, I've ignored my own needs and my stiff manhood aches. As I lay next to my exhausted cousin and gather in my arms, I can't help but grind into her bare hip.

The girl's eyes clear and she comes to a sudden understanding. "Guess I'm being selfish," she whispers meekly.

"That's nothing new," I reply. She scowls playfully and punches me in the stomach. I make to kiss her again, but she ducks out of my embrace.

Roxy's eyes glitter up at me mischievously. "No, you were right before. It's your turn, now." Her hands slide down my chest and stomach, then over my pants, kneading the hard rod contained by denim. She slaps my hands away from helping her unbutton them. The zipper opens haltingly, fighting against the strained material. I raise my hips obligingly and she pulls down my pants and boxers together.


he evidence of my excitement almost slaps her in the face as it springs up. My cousin just stares at it and I begin to feel a little self-conscious. I'm a thick seven inches cut, nothing to sneeze at, but I always wondered if it looked small compared to my body size. She scrunches her nose at the musky scent, but if she's dissatisfied with the size, it doesn't show. In fact, I can tell this is her first time with a penis in person, judging by the reverential way she studies mine.

Her fingers brush it, then jerks away as if burned. "So hot," she mutters. They come up again and encircle it. Working slowly, deliberately, Roxy massages my erect organ, as if studying each swollen ridge and pulsing vein. Her breath, heavy and moist, tickles the engorged head that is inches away from the lips I've wanted around it for so long.

I reach down and run my fingers through the chocolate brown tresses that cascade around her face. My cousin looks up at me sheepishly through her bangs and after a long time, I see once again the cute little girl that liked throwing stuff at me. What boldness she showed has passed; she has no idea what to do.

Taking her cheeks into my hands, I guide her down. Her thick lips quiver anxiously as they meet the round head of my member. She starts to kiss it and her touch makes my skin burn like fire. I moan encouragingly, spurring her on to try more. Roxy consumes the red bulb and swirls her tongue around it; I have a mental flash of a girl in a pink tutu, watching me with intensely dark eyes as she sucks on a lollipop. Her lips press around me tighter and her tongue laps harder. I wince as she nibbles lightly. Inexperienced though she is, I fear I've waited too long and may lose my control early.

Mercifully, Roxanne releases me from her mouth with a wet pop. She looks up at me questioningly as she begins to lick along the underside of my shaft and I fail at holding in a chuckle. Full cheeks color at the perceived mistake, but she soldiers on, modifying her approach. Her lips wrap around the base and move upward, a wide lick narrowing with each inch until only the tip flicks across the frenulum. One hand lightly strokes my length while the other massages my balls. She continues this for a while, until I to moan in frustration. I plant my feet on either side of her and begin to thrust my hips, trying to dive back into her luscious mouth.

With my head resting back, I can't see what Roxy is doing as she withdraws from her activity. After a moment, she grips my erection firmly and engulfs the swollen head once more. But now there is a new sensation as wet fingers slip between my butt cheeks and find the manhole. Without further ado, her fingers dig into me. I'm no anal virgin either, so it's far easier and definitely welcome as the muscular ring contracts around her knuckles.

"Mmm! Kinky," I joke. Sweat runs into my eyes.

"Yoo slarmig id," my cousin mumbles, barely intelligible around the slab of meat between her lips.

Lightning shoots up my spine as Roxanne miraculously finds my prostate on the first try. Realizing her success, she prods the spongy tissue mercilessly, causing my considerable bulk to writhe in delight. Her mouth descends the shaft of my member, taking in several more inches. Fingers tightly wound about the base stroke at a feverish tempo, yanking up to meet her lips and slamming back down to my crotch. Her tongue does nothing, all her efforts concentrated on sucking like a vacuum. My cousin's technique is sloppy, but effective.

As I reach my climax, I unintentionally jerk into a sitting position. I distantly notice her muffled sound of alarm as the added weight of my chest pushes her head down, driving my member deeply into her mouth, but I'm in no state of mind to pay heed. I swear I hit her tonsils as I cum, injecting seed straight down her throat. Jizz fills her mouth and bubbles at the corner of her lips as she chokes it down.

Finally, I'm spent. Months of pent up tension evaporate as I sink into the comfy corduroy cushions. Roxy's face comes into my view, her red expression livid. Eyes burning darkly, I can tell she's preparing to ream me a new one.

Without warning, light floods the living room through the picture window. The sound of crunching gravel reveals Bill's SUV has just pulled into the driveway. Her anger forgotten, Roxanne stumbles off the couch, yanks up her pajama pants, and bolts into the kitchen. I duck low to avoid being seen and follow. I barely make it past the threshold before she jams a wad of paper towels into my groin. I cringe, but obediently dam my still-leaking manhood and stuff it away.

"Dammit, now I gotta take another shower!" she agonizes.

"Go. If they ask, I'll tell them you just got back yourself."

"It's an hour past curfew!" she shrieks. Roxy gasps and covers her mouth and her eyes go wide. Kerry still seems to be asleep and there's no indication her parents heard from outside.

"There are worse things you could get in trouble for," I remind her. She nods quickly and turns for the stairs. "Wait!" She jolts to a stop and I give her a peck on the check, then slap her ass. "Sweet dreams, cuz'."

Roxy vaults up the stairs and the voice that replies from the second floor now has the tone of a girl who got away with doing something naughty. "Good night!"

On cue, the front door opens; Bill and Marlene walk through. "So how was it?" my aunt asks.

"Uneventful," I lie, turning off the television.

Bill has stopped in the middle of taking off his jacket and he looks around, like a bear noticing a foreign scent in his den. The analogy couldn't be more appropriate. Uncle Bill is sorter than me, but twice as wide with the muscular build of a construction worker born and bred. There's no doubt in my mind that he could break me in two if he so desired. I do not want to get on his bad side.

"When did Roxy get home?" he says at last.

"Just a couple minutes ago. She's upstairs. I was getting ready to leave now that she's back."

"Tsk, that girl," he growls. "Her curfew is eleven. I'll give her a talking to in the morning."

"Cut her some slack, Boo," Marlene says, using his private nickname. "It's her birthday after all."

Bill eyes me sharply and I make a zipping motion across my mouth, indicating that his secret is safe with me. Satisfied, he relents. "Fine. But just this once. Here, k**, lemme pay you." Ham hands dig into a jacket pocket for his money clip, but I wave him off.

"No need, Roxanne already paid me." It's almost the truth. I pat him on the shoulder and give my aunt a hug. "I hope your evening was more fun than mine. G'night!"

I leave and close the door behind me. Once I'm safely on the other side, I let out an explosive sigh of relief. That was a close one, but my record of skin-of-my-teeth saves is unbroken. As I climb into the old Ford, a shout goes up from inside the house. My hands turn clammy as I realize I left the liquor cabinet open. Looks like I'll have something to explain at the next family reunion.

I glance up to the second story windows and spot Roxanne waving at me from her darkened bedroom. Something to look forward to as well, methinks.

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My name is John, a typical “English” name for a typical “English” guy. At the age of 15 my family, mother father and two sisters were tragically killed in a motor accident whilst I was on a Rugby tour in the U.K. My nearest relative was my father’s cousin Herbert, or Herb as he liked to be called. Herb was married to Josie, they had not been fortunate to have children of their own and so willingly accepted me into their family in America. It was obviously a shock and upheaval and as such I...

2 years ago
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Babysitting The Twins 1 Revised

To people who are about to read this story: YES, THIS IS A YOUNG STORY, THAT MEANS UNDERAGE, NOT ADULT. SO IF YOU DON'T LIKE THESE KINDS OF STORIES JUST STAY AWAY. I DON'T NEED TO SEE THE STUPID COMENTS, BECAUSE YOU DON'T LIKE THESE KIND OF STORIES. . I do like feedback; I'm not a professional writer so I'm sorry if it's not perfect. I did read through it a few times and I hope I got out most of the dumb mistakes. I'm very sorry if I didn't. Babysitting The Twins I’m...

4 years ago
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Babysitting Kizzy

Introduction: Young Minx Let me introduce myself, sorry for the guys who just want a quick wank but as this is true here is the prelude to what turned out to be a great adolescence after a devastating start. My name is John, a typical English name for a typical English guy. At the age of 15 my family, mother father and two sisters were tragically killed in a motor accident whilst I was on a Rugby tour in the U.K. My nearest relative was my fathers cousin Herbert, or Herb as he liked to be...

2 years ago
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Babysitting Sis Part Two

Introduction: The affair escalates… Babysitting Sis Part Two It was late at night and he couldnt sleep. He and his thirteen year old sister had had sex together in the family pool earlier that evening while he was supposed to be babysitting her, and now he couldnt stop thinking about it. He had a raging hard on as the scene played through his mind again and again, one hand stroking the rock hard cock as he pictured what had happened. All he knew at that moment was that he wanted his sisters...

4 years ago
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Babysitting the Twins

Introduction: A little something I thought up… Ive been babysitting for my neighbors since I was about twelve or thirteen, so thatd make it a five year business for me. I just turned eighteen earlier this month, and Ill be heading off to college later this summer. Ive never really had to get a job, just because my neighbors go out so much that it keeps me paid steadily! Naturally I do have favorite families to look after and others that I do not like so much. My favorite in particular is the...

2 years ago
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Babysitting Candy

Introduction: This story is a work of fiction and contains descriptions of Babysitting Candy When Jessica turned fourteen, her mothers best friend and neighbor asked if she would like to earn a little money babysitting her daughter when she wet out. Jessica was thrilled at the idea of earning her own spending money. Besides she thought her mothers friend Tina was very sophisticated and looked upon her as the kind of woman she wanted to be when she grew up. Jessicas family lived on the edge of...

2 years ago
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Babysitting

BabysittingShe didn't know why he was babysitting her, she was old enough now not to need a babysitter when her parents went away, besides he was almost the same age as she was! ?She followed her mother around a little dejectly as she showed him the place, as well as the phone numbers to the various local take away places. ?She knew this boy too, he was one of the bad boys at school always getting in trouble and known to be quite mean. ?Finally her parents leave, giving her a hug as they leave...

4 years ago
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Babysitting Fun

Introduction: Julie missed the party to babysit, but didnt miss the fun… Graduation was just around the corner. I couldnt wait. Id spent the last two years planning on where I was going to college and couldnt wait to get away from under my parents thumb. It was Friday and I was planning on meeting up with some friends at a party. It was a come in uniform party and I was just putting on my little catholic school girl uniform when my mother came into my room. I forgot to tell you. I told Mrs....

4 years ago
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Babysitting fun1

“I forgot to tell you. I told Mrs. Winters you’d babysit for her tonight. She has to spend the evening with her sister and needs you to watch the baby.” I pulled up my white socks and just looked at her. I love my mother but she does this to me every time. “I was planning on going to a party, Mother. Not babysit.” “Well, so now, you’ll babysit. You said you wanted extra money for summer and college. Here ya go. Besides, you can go to other parties. I know there’s probably another one...

2 years ago
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Babysitting for my Uncle part 2

~•~•~•~•~•~•~•~•~•~•~•~•~•~ "Surprise..." my uncle and I hear from the door. I cover myself quickly and look at the door. I knew that quiet voice as my cousin's who was currently in college. Well now I knew he was home as he stood in the door frame with a few bags in his hands. His facial expression was unreadable. I didn't know if he was surprised, scared, turned on, or calm. That scared me more than anything. I didn't want this secret to leave the room. I could feel tears slowly...

2 years ago
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Babysitting the Twins Again Part 2 Sweet Sixteen

Debbie gives two gifts to her sweet sixteen sister. …Jenny is overwhelmed. Babysitting the Twins Again - Part 2 - Sweet Sixteen The marriage and honeymoon are over and Debbie settles into a life of family bliss. She’s never been happier, but she realizes that big changes are coming. Debbie is starting to show. It’s been great, but she must stop being the receptacle for all that the young twins ejaculate. The summer of strenuous sex must end… Monday morning When the twins...

3 years ago
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Babysitting Craig

I had done more with other boys in the neighborhood when I was around Craig's age, but that seemed to stop just before, or shortly after puberty. Some of them began to realize that it was sort gay to do things like comparing the size of our boners, or play games of truth-or-dare that always lead to the removal of clothing. We should have just called the game "dare" because I don't recall any of my little playmates selecting "truth." It was always somthing along the lines of: "I dare...

4 years ago
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Babysitting the Aunt Kay Way

This story takes place back in 1980 and involved a young man named Lance Bowman, an 18 year old lad about to graduate from high school, and his Mom's sister Kay, who came to babysit that spring when Lance's mother was hospitalized once again for the recurring health problems which would eventually take her life.The babysitting was actually for Lance's k** sister Emma, because Lance was a very trustworthy lad who could take care of himself. Lance was fine with that, because he was very fond of...

4 years ago
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Babysitting

Babysitting By RogerGirl I'm sitting at the kitchen table on Friday afternoon eating a bowl of cereal while my parents scramble to pack their bags for their weekend trip to Vegas with the neighbors. I try to hold back my anticipation for them to leave so that I can spend the next two and a half days indulging in my secret hobby. Don't worry I'm not into drugs or drinking and I'm not planning to invite my girlfriend over to have sex nor am I planning a wild party. ...

1 year ago
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Friends With Benefits

The whole concept of Friends With Benefits can be a little controversial, depending on who you ask. There are dudes out there who claim it never works out, that there are always strings attached, no matter what she says. I’ve had my share of supposedly casual hookups that went sideways when the babes got jealous, but it doesn’t always go that way. In my experience, things tend to work out best when you’re really up front about what you want. These days, you don’t have to be looking for a...

Hookup Sites
3 years ago
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Babysitting Blues

The fact that my gym was in the same building that I lived and worked was a plus. The incentive program my boss set up didn’t hurt either. The gym was state of the art and he could see my workout history any time he wanted to and he actually paid me for it. He insisted I stay in shape “for the business” he would say. I was perfectly ok with that as long as it resulted in money in my pocket and a tight body. The money was special. I didn’t tell anyone but the fact that a secretary, excuse...

3 years ago
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Babysitting for Married Men 2

When I finally built up my courage to make something happen, I dressed for the job "to the nines," short skirt, silky blouse, black underwear including a garter belt and stockings. I stuffed a strip of condoms in my purse. Toni was far away in Minneapolis. By the time I came over, the day-sitter had left and Toni handed me the baby. I love babies and I let Eric watch me cooing over the baby and make baby talk. "She's so cute," I said. This gave him a big smile, but he had to rush off...

2 years ago
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Babysitting Alex Part 4

Wednesday I woke up and I was alone in bed, so I got in my underwear and went downstairs, Aky and Mark were in their underwears playing Xbox, I was actually starting to see both of them as my little brothers, I was mostly always alone because I am an only child, that led me to be a little cold towards people and of course, a bit shy when meeting new people, but seeing both of them there, made me get warm, and happy. "Good morning you two" I said. "Morning" both said not taking...

2 years ago
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Babysitting Sucks Chapter 2

Matthew opened the front door. “Hey baby.” It was Lorraine, Matthews girlfriend. She was absolutely gorgeous, he knew he was hitting well out of his league with her. She had silky smooth, perfectly straight, mahogany hair. Her skin was flawlessly tanned, her eyes a mesmerizing, turquoise, and her smile could kill demons it was so heavenly. He knew that he should be thrilled to see her but after what had transpired a couple of days ago, he was less than pleased that she had turned up...

4 years ago
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Babysitting he was no baby

It was for a family in the next block and they had a 12 yo son and an 8yo daughter. On the third time I sat for them I was using their toilet and the boy walked in and said “Can I fuck you“ and he was fondling his penis sticking out his pajama pants. I was really astounded at his proposal and his forthright manner in which he asked. He also had quite a big cock for a boy his age. My immediate reaction was to say “no”. I was quite taken back and could not think of anything else to say. His...

3 years ago
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Babysitting Sis Part Two

Part Two It was late at night and he couldn’t sleep. He and his thirteen year old sister had had sex together in the family pool earlier that evening while he was supposed to be babysitting her, and now he couldn’t stop thinking about it. He had a raging hard on as the scene played through his mind again and again, one hand stroking the rock hard cock as he pictured what had happened. All he knew at that moment was that he wanted his sister’s tight pussy again, wanted to feel her move...

3 years ago
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Babysitting Candy

When Jessica turned fourteen, her mother's best friend and neighbor asked if she would like to earn a little money babysitting her daughter when she wet out. Jessica was thrilled at the idea of earning her own spending money. Besides she thought her mother's friend Tina was very sophisticated and looked upon her as the kind of woman she wanted to be when she grew up. Jessica's family lived on the edge of town in a pretty new housing development. Every house in the...

3 years ago
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Babysitting games

One day, Tony called me and asked me to come over. When I knocked on his door, his seven year old brother, Tommy, answered and proceeded to tell me that their parents were out playing golf and that Jason was babysitting them. I followed him back to Tony’s room where everyone was hanging out. I sat on the bed and looked up and Jason. I’d seen him around the neighborhood but I didn’t really know him. He was fourteen and our age different was such that we ran in different circles. After a...

4 years ago
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Babysitting with Tara pt1

It all started about 2 weeks ago. My friend Tara and I were babysitting, a normal activity for us on Sundays, seeing as both of her parents worked nights and she had two younger siblings. It was somewhat late, around midnight, but we were both sitting on the couch, just kinda shooting the shit, waiting for her parents to get home. Normal stuff, like which teacher we hated the most, how we think we did on the biology test. Normal, 16 year old bullshit. The conversation started to get a bit...

2 years ago
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Babysitting my little cousin

Introduction: When they could not find a babysitter, Mom and dad asked me to sit for my little cousin. The publishing rules say that everyone in these stories has to be at least 16 so even though the story is totally fiction, everyone in it is at least 16. Enjoy. Babysitting my little cousin. My name is Todd. I am 19, six foot one and weigh 160. Im told that I am attractive. I dont want to sound conceded but I have to agree and that makes it pretty easy for me to get dates. I dont have or want...

2 years ago
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Babysitting

EveryThursday night I babysat for the Harrisons. Like always I arrived home from school at four o’clock and jumped into the shower before heading over to their house. It was my senior year in high school, only one month till graduation. I was psyched for the school year to be over, but I knew I would miss babysitting for them. I had gotten the job because I went to school with their eldest son Jason. He graduated two years before me and went off to college. After I got out of the shower I went...

2 years ago
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Babysitting Amanda 1 and 2 edited

Note: This is a re-write of Babysitting Amanda 1 and 2. I cannot plagiarize my own stories so do not accuse me of such. As usual, do not waste time with accusations and insults against me. Finally, some ages and details have been changed from the original stories. If you have not read my stories before, make sure you read My Cousin Tom 1 and 2. Characters: Jake- 16 Amanda-14 Becky- 7 Jane- 30 Let me introduce myself. My name Jake and I am 16 years old. I was your classic horny teenage guy. My...

4 years ago
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Babysitting for the Ulichnys

* Hey everyone, this is a long WIP, and i'm willing to let people contribute, feel free to add or write a chapter, and if the quality is good, it will stay.* The Ulichny's had always been good clients. Their three kids were well behaved, quiet and always seemed to be ready for bed. Babysitting for them was always fun because it usually meant plenty of free time to just relax, and get paid for it. Chantal was a good looking woman, at best. She wasn't skinny, but wasn't big either. Around your...

Gay
3 years ago
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Babysitting brothers Daughters

My older brother called and said he needed a big favor. His company was sending him on a business trip overseas and he will be gone for the next couple of months. He could take his daughters with him but Cat, short for Cathy, will be graduating from high school in a month and she didn’t want to leave and miss it. Mel, short for Melody, is a star pitcher for the school’s softball team and they stand a good chance of going to the playoffs and she doesn’t want to miss our either.He wanted to know...

4 years ago
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Babysitting

EveryThursday night I babysat for the Harrisons. Like always I arrived home from school at four o'clock and jumped into the shower before heading over to their house. It was my senior year in high school, only one month till graduation. I was psyched for the school year to be over, but I knew I would miss babysitting for them. I had gotten the job because I went to school with their eldest son Jason. He graduated two years before me and went off to college. After I got out of the shower I went...

Straight Sex
2 years ago
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Babysitting Karen

My wife and I were babysitting Karen; the daughter of the wife's brother. ***Melissa, my wife and I have been married 15 years and we have an incredible sex life and sex drive. We have tried everything, or so I thought, until my niece came to stay with us for a weekend.Melissa's brother and wife had to go away for some business seminar so asked my wife to baby-sit. Karen is 14 and very cute, but very tomboyish, the type that wears jeans and loose fitting shirts all the time and likes to play...

1 year ago
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Babysitting for Married Men 2

Mrs Riker had recommended me to the Jacksons as a babysitter, and I have to tell, you Mr. Jackson was a hunk. He had weight lifting equipment in the basement and it was well scratched up from repeated use. Eric had the classic broad shouldered figure of a guy who stayed in shape without becoming musclebound. I vowed to have him the moment I first saw him. I started working on him the second time I sat for them, especially when his wife Toni was out of sight. There's a way you can be so glad to...

Erotic
1 year ago
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Babysitting can be fun

Jenna was a tall black haired bomb shell with big tits and a nice arse. Nikke had smaller tits but a nicer arse. They were both in skinny jeans and t-shirts while babysitting nikki's next door neighbours kids sleep over. There were 6 18 yo boys down stairs playing games when the girls were bored. "hey nikki, why dont we go and get some fun out of those virgin boys down stairs? Jenna suggested "lets do it." Nikki replied with an evil smile. They both went down stairs snuck up on the 18yo boys...

Group Sex
1 year ago
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Babysitting for Married Men 1

I'd been babysitting for the Rikers since I was 17 and they both were really nice. Candice taught me so much about taking care of their babies and now little kids, Jeremy and Jessy. Matt was always polite and friendly and always inquired about my schoolwork and sports. I'd had a schoolgirl crush on him off and on, but of course I knew he was married, so I always put it out of my mind. I was just 18 and Candice had to go out of town to visit her mother, who I guess was needing to move to a more...

Erotic
4 years ago
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Adventures in Swinging Ch 04 Friends With Benefits

Ron and Charlotte seemed like a perfect match for us. They were around our age, lived fairly nearby, and had little swinging experience. He was handsome, fit, and bald – Kathleen’s favorite traits. She was very cute, petite, and had a beautiful smile and gorgeous eyes – my favorite traits. When we exchanged messages online, they seemed intelligent, honest, and genuine. In our lengthy search for “friends with benefits,” they seemed almost seemed too good to be true.As attractive as Charlotte...

Wife Lovers
2 years ago
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Fringe Benefits

Driving into the driveway this house looked pretty promising. The ad was about a garage apartment and the house had a three car garage so it should be pretty large. Dan parked his car, got out and headed for the front door. Knocking on the door he was glancing around taking in the nicely manicured lawn and fantastic landscaping. The door swung open and Dan was struck a little speechless. Standing before him was one of the sexiest women he had ever seen. Dark auburn hair and green eyes. ...

3 years ago
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BENEFITS

"I hope this apartment is nice" Dan thought. He had been looking at apartments all day and had seen some real shit holes. This apartment was a little more expensive than what he had planned, but it would be worth it. He had to start work on Monday and it was already Saturday. The new job he was starting in Flagstaff hadn't given him much notice, it was a great opportunity, but it was all such a rush.Driving into the driveway this house looked pretty promising. The ad was about a garage...

2 years ago
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Fringe Benefits

“I hope this apartment is nice” Khan thought. He had been looking at apartments all day and had seen some real shit holes. This apartment was a little more expensive than what he had planned, but it would be worth it. He had to start work on Monday and it was already Saturday. The new job he was starting in Flagstaff hadn’t given him much notice, it was a great opportunity, but it was all such a rush. Driving into the driveway this house looked pretty promising. The ad was about a garage...

4 years ago
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Friends With Benefits

Friends with Benefits By Teri Franken Chapter 1 My daughter was grown up and away at school, the dog had died and my wife was ready to do her own thing. I found myself divorced and on my own in Chicago, just my job and my "hobby" to keep me company. I was an upper level manager at an electronics company and made a nice six figure salary. As for my hobby, well let me say that I enjoy being comfortable when I am at home, and when I am dressed in women's clothing. Yes, I am a...

3 years ago
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Teaching Benefits

Teaching has great benefits that far outweigh the costs. I know that not everybody enjoys those benefits in the same way, but there is a thrill that comes when your students "get it." When that light bulb goes on over their head and you can see that what you've tried to share has been received, there is a sense of incredible happiness that floods your soul and lets you know that you have done well. Of course, there are other benefits, as well, that extend beyond the altruistic. When I...

4 years ago
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Melanies Discipline Regime Unforeseen Benefits

The routine was well established. Claire operated the ‘Zero-tolerance-no-second-chance’ discipline regime, which Melanie readily accepted.Melanie was eighteen years old and had tricked her step-mum into changing grounding and time-out to an instant over-her-knee bare-bottom spanking with scolding before, during and afterwards. Melanie preferred the immediate, albeit painful, discipline to the arduous grounding which was normally up to seven days with the occasional longer period, and even a...

Spanking
4 years ago
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Starting Of Friends With Benefits

Hi, Guys and Girls, I have been a big fan of ISS for at least 3 years and this is my first sex story I’m publishing which is my real life incident which happened to me a few months back with my friend Archana at the escape cinemas in the express avenue at Chennai. So about me, I’m 21 years old guy from Chennai and I stay at Nungambakkam. I love to travel, watch movies and TV series and the best thing about me is I’m a professional state level swimmer, so I have a very good body which I’m really...

3 years ago
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From Friends To Friends With Benefits

This is my first story in ISS but a real one, My name is Rahul and I’m from Tamil Nadu. The heroine of this story is Sindhu(name changed). Sindhu and I were close friends from college and in this story I will tell about how our 5 years of friendship suddenly turned into friends with benefits kind of relationship. I never had any sexual intention on sindhu throughout my college days. I completed my UG in a college from my hometown. I became friends with her since day 1 that’s because we use to...

2 years ago
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Best Friends With Benefits

Hi, I am Vijay, 23 male from Kerala. My email id is This is a true sexperience with my best friend Revathi. I write this with her permission. For our privacy Names are changed. About me, I am an average mallu boy. I don’t have a big dick (it is 15cms, i measured with a ruler). I am good looking and fair. Revathi is a little dark complexioned, but beautiful with big round eyes and have perfect shapes. This story happened four years before. I joined college after one week the classes started....

3 years ago
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Love At First And Friends With Benefits

Hi friends, I am rahul I am 27 years old and this story is about my first sex experience which happened with my best friend ruchika(name changed) she was one of the best bombshells in our college, guys would used to die to talk to her, I was quite lucky to sit next to her because I was her best friend, I always had feelings for her but never shared it with her because I did not wanted to ruin my relationship with her. I was also dating a girl that time so I didn’t feel that it is appropriate to...

4 years ago
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Sex In Mysore With Friend With Benefits

I’m reading stories on ISS since a year and thought of writing down my story also which happened 5 months back. Let me introduce myself. My name is Rahul and I’m 5’7ft with an average build and 6 inches dick which can satisfy any unsatisfied female. Mail me on My friend and I were in 2 different colleges and it was the first few days of college. I knew her from past 4 years and we were best of friends. We used to have all types of talks including sexual talks and stuff. One day while we were...

2 years ago
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Benefits

Copyright ©2005. All rights reserved. Caveat lector. "What are you staring at?" she asked calmly, knowing full well what he was staring at. Startled, he tore his eyes away and looked toward her face. He could feel his eyes being pulled inexorably downward again and fought the urge with every ounce of willpower he could find, but it was not enough. When she had entered his office for her interview, he thought he heard some soft talking and a giggle from outside the door. He had an important...

3 years ago
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Babysitting

So during a scorching hot summer i didn't feel like going into the evil sun light and get sweaty sack so i stayed in my cool basement secluded from anyone. *(yes i sound like a creep)* But one day my mom wanted me to stop being a useless shit and go and do something so she told her friend that " I WOULD BE ABLE TO BABYSIT" Dumb bitch! well i got to go to this smoking babes house and it was TOTALLY WORTH IT! So I arrived at the house around noon sweating hot from biking up this crazy hill and i...

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