Babysitting Benefits

Story Info
Favor to family creates dream opportunity.
4.9k words
4.17
447.3k
35
0
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

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 kid. 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 lolita 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.

12