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Surprising His Sitter

Short story By: goldeniangel

Rick's tired of lackluster dates... and then he gets the surprise of his life when he comes home to find his usual baby-sitter lying in his bed and masturbating with a dildo while calling out his name. The kid's asleep... so what now?

Submitted:Dec 20, 2013    Reads: 12,497    Comments: 21    Likes: 34   

She was going to say it. Rick gritted his teeth into an approximation of a smile as Laney fluttered her eyelashes at him and then their waiter, the very picture of a helpless female.

It'd be a lot more endearing if the dilemma she was facing had an importance. Or if she hadn't said the exact same thing on the other two dates he'd taken her on.

"Ooooo, I don't know," she cooed, pouting her lips out. "Do you think we should indulge a little? I already ate so much!" Tinkling laugh as she rubbed her hand over her completely flat stomach.

The dating world had turned brutal, even though he'd only been out of it for a while. Half a year to meet and fall in love with his wife, another half to plan and have a wedding. One year to the birth of their son and her horror at what carrying a baby had done to her body, her rejection of Jordan in her resentment and another year till the divorce was finalized. They'd both wanted children and he'd never minded her constant obsession with her looks until after Jordan was born and she'd wanted him to get a vasectomy so that she wouldn't "entirely" lose her figure by getting pregnant again. He'd rather liked her curvier figure, but nothing he'd said had made any different. Clarissa had neglected Jordan to go to the gym and spa, and all their discussions about having at least two children, hopefully three, had gone completely out the window and his marriage had gone belly up.

Now Jordan was four and Clarissa had signed all rights to him away. Rick didn't want his son to grow up completely without feminine influence, and to be honest he rather missed having a woman around the house, and he still wanted marriage and more kids, the whole nine yards, so he'd decided it was time to get back into the dating scene.

Before Clarissa he'd never noticed when a woman talked about food, her weight, calories, or hemmed and hawed over dessert. Now he noticed every instance of it and it drove him batty wondering if they would have the same reaction to being pregnant and a mother that Clarissa did. Surely she had to be unusual or no one would be having babies... but any attraction he felt for a woman went out the window once she started to remind him of Clarissa.

Granted, Laney wasn't his normal type anyway. He was pretty sure that parts of her were already plastic, even he could tell that her hair was dyed (and what was with those chunks of blonde?), and she had a tendency to flirt like thought she was in a movie or something, but she'd chased him down at the coffee shop he normally frequented and he'd thought why not? Rick knew he was a pretty attractive guy, thirty one years old, tall, dark and handsome, and he certainly didn't have trouble getting a date when he wanted one, but none of the women he'd asked out had worked out and so he'd thought why not try someone who wanted to ask him out? It had a certain appeal, woman who knows what she wants and everything.

But then why couldn't she ever decide if she wanted dessert?

"I'm feeling kind of full myself," he said, handing the menu back to the waiter. "Just the check please."

Laney pouted at him and he fought the urge to roll his eyes. If she'd wanted dessert she should have said so. And he didn't want to spend any more time with her than he had to at this point.

Pay the check, get her out to the car. Make awkward conversation on the way to her house.

"So, we're done a little early," she said flirtatiously as he walked her up to her door. "Want to come inside for a cup of coffee... or some dessert..."

For a moment he seriously considered going inside just to get laid. It had been... hell, it had been months since the last time he'd been with a woman and that had been the night of a drunken bar crawl with some of his buddies when his divorce was finalized and he could barely remember it. But then he'd feel obligated to go out with her again...

"No thanks," he said. "Have a good night."

"Will you call me?" Now she was looking up at him with big eyes, but she didn't actually look sad. Just a little disappointed.

He hesitated and then decided to go for the truth. "I'm sorry Laney, I like you and you're a great woman, but there's just no spark for me."

To his relief she didn't pout, instead she let out a little sigh and shrugged her shoulders. "Yeah... I guess I should have realized that considering that you've never even given me a good night kiss. Oh well. Have a nice night, Rick."

"Thanks, you too."

Somewhat bemused he headed back to his car, checking his watch on the way. Wow. They really had rushed through that date, it was almost an hour and a half earlier than the time he normally was home from a date. Reaching into his pocket to grab his phone to let Dana, his baby-sitter, know that he was coming back early, he cursed when he realized it was out of battery.

A quick search of his car turned up one of Jordan's snack packs that he must have thrown on the floor at some point, but no car charger. Oh well. He'd always texted Dana when he was on his way back, ever since there had been a series of break-ins in their neighborhood so that she didn't get freaked when someone came through the front door.

Dana had been baby-sitting Jordan for the past three years. She'd been eighteen when he and Clarissa moved in, still living with her parents and going to community college; next year she'd be going to the local university and still living at home with her parents to save money. Thank goodness or he'd have to go looking for a new sitter.

If he'd been a younger single man when he'd first moved in he probably would have had the hots for the cute little girl next door. While she wasn't a knock out, or even the kind of girl that made guys heads' turn, she had a wide smile, firm curves, and short brown hair that bounced around her chin when she walked. The kind of girl a guy would feel immediately comfortable with and then he'd notice her soft pink lips, the way her eyes sparkled when she laughed, and the innocently seductive sway of her hips. Clarissa had occasionally made snide comments, because Dana wasn't a perfect size 2, but he'd always defended her - and secretly wished that Clarissa would take the hint that he didn't mind a few curves. Maybe more than a few. He'd loved Clarissa, but even before she'd gotten pregnant with Jordan he'd realized that they may have moved too fast... they hadn't even really lived together before getting married and her body / looks obsession had suddenly become clear once they were. More than once he'd enjoyed getting an eyeful of the girl next door, enjoying her natural good looks and her aura of cheerful confidence.

Being ten years older than her made him feel like a dirty old man when he checked her out, but fortunately Dana had never seemed to notice. And Jordan just adored her. She came over to play with him sometimes even when she wasn't babysitting, giving Rick plenty of time to indulge in dirty baby-sitter fantasies. Unfortunately Dana had never indicated that she noticed him at all, she was all about Jordan.

Or maybe that was fortunate. Dirty old man. He laughed at himself. Like a twenty one year old would have any interest in a thirty one year old divorcee with a three year old. Keep dreaming.


The house was mostly dark when he pulled up, which meant that Jordan was behaving and sound asleep. Dana was probably in the television room, watching a movie.

Grabbing the snack pack he'd found, Rick heading up the front walk and unlocked the door. To his surprise he didn't hear any noise at all, which is what he would have expected had Dana been watching a movie. Frowning he walked into the hallway through the stairs; from the bottom of the stairs he was able to see into the back of the house. The kitchen light was on but there was no one in there.

Maybe Jordan wasn't behaving as well as he thought and Dana was having to read him a story or something. Lately Jordan had been fighting bedtime. Smiling in amusement, Rick headed up the stairs to see if he could help.

The sound of a low moan when he reached the top of the stairs made him frown in surprise. Jordan's door was firmly shut, but his own bedroom door was open just a crack and light was shining through.


It was a sound that he hadn't heard in a long time. Months. Low, sultry, he found himself moving without thinking, as if it was a Siren's call beckoning him onwards to certain destruction. Blood pounded in his head and he felt his cock twitch in response, the instinctive physical reaction of a male to passion in a female's voice.

He was only a step away from the door when he heard his name and any reservations he'd had left, any hesitations were wiped away in pure, unadulterated lust as the blood in his groin surged and his cock hardened to the point of being almost painful. It had been far too long since he'd heard a woman say his name like that.

A gasp. "Oooooo… Oh god… Rick… please…."

Fingers pressed against the door and it swung open.

The vision before him would be seared into his brain for the rest of his days. Directly across the room from him, laid back on his bed with her thighs spread wide, knees pointed at the ceiling and feet firmly planted on the mattress, was Dana as he'd never seen her before. She wasn't wearing a single stitch of clothing. The roundness of her breasts, the pert dusky dark pink of her upright nipples, the creaminess of her thighs, his mind catalogued all of it in the time it took to draw a shocked breath. Both hands were busily moving between her thighs, one shoving a plastic dildo in and out of her glistening cunt, the pouting pink lips shaved completely bare, just a small thatch of hair on her mound which was almost obscured by her other hand as it played with her swollen clit.

In the time it took for her to realize that she was no longer alone in the room, the smell of her arousal had hit Rick's nose and joined the visual in going straight to the primitive side of his brain. He was halfway across the room, cock throbbing with need, before he even realized he was moving.

It was her shriek that stopped him, and he jerked his eyes up away from her delectable pussy and to her face as she sat up, her thighs coming as her hands flew to her breasts, shielding herself from his view. They stared at each other for a long moment as they both tried to compose themselves.

"You're home early," Dana squeaked, her pretty face going from bright pink to a darker red. "You didn't text." It was almost accusatory the way she said it.

"My phone died," he said, hand going to his pocket and patting it. Dana's eyes followed the gesture and then slid several inches to the right to land on the obvious bulge of his cock. She turned even redder, but it was like she couldn't look away.

He knew the feeling.

Scrunching her knees closer to her chest, her ankles crossed in front of her privates so that he couldn't even see the dildo that was still lodged inside of her, and her knees obscuring her breasts, she covered her face with her hands as if the full impact of the moment was finally catching up with her. "Oh my god… oh my god…"

"Dana… Dana it's okay." He found himself moving again before stopping to stand awkwardly next to the bed. How to comfort a mortified naked girl with a fake cock stuck inside of her while his own erection showed no sign of subsiding?

Plus it was really hard to concentrate while his brain was busily focused on storing images of Dana's soft skin, the way the curve of her breast pressed against her knee, the fact that her ass and maybe even her wet pussy were pressed against his sheets. He had to stifle the urge to just grab her and replace the dildo with his own cock.

On the other hand… she had been calling his name. While masturbating on his bed.

His brain yelled at him that he was a dirty old man, even if it was really only by comparison to her, while another part of him said that ten years wasn't really that big an age difference.

Reaching out, his hand hovered over her shoulder, wanting to touch her but unsure of her reaction if he did.

"Dana, really it's okay, I don't mind," he said. What an understatement. Tonight would be burned into his brain forever, and he'd jerk off to each and every second of it. Multiple times.

Big brown eyes turned up his way, shiny with unshed tears. Her voice was shaky. "You don't? I mean… you aren't disgusted with me?"

Oh god, please don't cry, he thought. Anything but that.

"Disgusted with what? Do you know how long it's been since I've had a gorgeous naked woman in my bed screaming out my name?" He chuckled a little and sat on the bed next to her, close to her but not quite touching her. Dana just stared at him as if she couldn't believe what she was hearing, but she didn't scream or jump up and run away so he took that as a good sign. "It's definitely not something that I have any objections to. Especially since I take it Jordan's fast asleep."

Although Dana's blush had never really gone away, it had subsided a bit and now it came back. "He is. And I kept the door cracked so I could hear him yelling if he woke up, although he never has before."

"Never…" Another rush of blood - how was it possible he had any left? - went straight to his groin as he realized that this was not the first time Dana had masturbated in his room. In his bed. God he just wanted to jump on her and smother her with his body and…

"I'm so, so sorry Rick… I'll understand if you never want me to baby-sit again."

He blinked, bringing himself back to reality and seeing how miserable she looked.

"Dana… I'm not upset. You'd be even farther away from Jordan if you were downstairs watching T.V. You're a great sitter and he loves you… and…and…" As he'd been speaking Dana had relaxed a little bit and her knees had moved just far away from her breasts that he could see her pink nipples again; still hard and oh so tempting. God he wanted to get his mouth around them and suck and - she cut off the view and he jerked his eyes back up to her face, his cheeks flushing hotly. Now he'd been caught too.

The look on her face was the most incredible mix of emotions - desire, hope, embarrassment, anxiousness, fear…

"Dana…" he licked his suddenly dry lips. "Dana, you were calling out my name right?"

She closed her eyes, as if she couldn't bear to look at him while she answered. "Yes."

"Oh thank god."

Her eyes fluttered open again, startled, as he leaned forward and cut off whatever she was going to say with a kiss. All the reasons he'd kept himself from thinking about her in that way had gone flying out the window. Soft lips parted on a gasp and he took advantage of the reaction to sweep his tongue into her mouth. There was a momentary hesitation and then she gave in to the kiss, her hands coming up to grip his collar and he leaned forward. His body weight pressed her backwards as he plundered her mouth ruthlessly. Dana whimpered as her head hit the mattress, her body writhing next to him.

Blindly he reached out and groaned as he touched the soft skin of her stomach, his hand immediately traveling upwards to cup her breast. They both moaned as he made contact with the soft mound of flesh, his thumb sweeping upwards to caress her nipple.

She shuddered and gasped as he broke off the kiss, shifting his weight so that he was kneeling between her legs, leaning over her so that he could get both of his hands on her gorgeous breasts. As he squeezed and kneaded the soft flesh, her thighs closed and rubbed against the outsides of his legs, her back arching upwards to thrust her breasts further into his hands.

For a moment her fingers dug into his shoulders and then moved upwards and into his hair. Rick was watching himself play with her boobs, fascinated by the way the soft flesh spilled out between his fingers, the rubbery nubs of her nipples so malleable between his fingers. With her hands in his hair, Dana brought his mouth down to her chest, and he went very willingly, sucking one nipple hard into his mouth and eliciting a small cry from her.

"Rick…" she moaned. "Oh god… that feels so good… Oh suck my nipple hard…"

His own groan muffled by her flesh, he felt his cock throb. Had a woman ever dirty talked to him? It was hot… not as if his dick needed any more encouragement with Dana all soft and sweet and yet somehow demanding, naked beneath him. Mewling, she writhed and her legs wrapped around the backs of his thighs, trying to pull his lower body down for her to rub against.

"The other one… please Rick, suck the other one…"

Not a problem. His mouth latched onto her untended nipple, leaving the first one slick and shiny with his saliva. As he suckled, his right hand slid down her body and over that trimmed mound of hair to find the soaked base of the dildo that was still halfway inside of her, partially displaced by her spasming inner muscles. Dana writhed and cried out as he pushed it back in and then began fucking her with the dildo while he sucked and bit at her nipple.

The squishing sound of her wet pussy giving way under the thrust of the dildo nearly unmanned Rick. It had been far too long since he'd had a woman underneath him, much less a passionate and vocal creature like Dana. She continued to moan and grind against him as he fucked her with the dildo, her nails raking through his hair and then down his neck to his front where she started pulling at his shirt.

Reluctantly he released the dildo so that she could pull the shirt over his head. Next thing he knew Dana was pushing at him and he rolled onto his back as she grinned down at him, all traces of embarrassment or shyness completely eradicated. Her eyes skated over his muscled chest and stomach, followed by two fingers that stroked from the center of his collarbone down to the straining button on his jeans.

"You're so hot," she whispered in a husky voice. "You have no idea how many times I've fantasized about you."

Rich groaned as she leaned down, her heavy breasts swaying, and sucked on of his flat nipples in her mouth, returning the favor. Her tongue traced around it and then she gently bit down on the tiny nub, his cock throbbing in response. One delicate hand rested on top of his bulge and his hips thrust upwards in response. The speed at which she got the front of his jeans was impressive.

When she got her hands into his pants and wrapped her slim fingers around his cock, he thought he might actually levitate off the bed, it felt so good.

"Good grief," she muttered, staring down at where her hand had disappeared into his pants. "You're huge!"

Laughing, Rick pulled her mouth down for a kiss, enjoying the way her fingers flexed and squeezed him tightly as he kept one hand firmly on her neck, the other reaching up to pluck at her nipple. When Dana finally pulled away she was panting, and he pinched at her nipple to try and pull her back down to him.

"Take off your pants," she ordered.

"Yes ma'am."

It took a moment, but she helped to him ease his pants over his hips before she tugged them completely off of him and threw them onto the floor. As she moved he reached for the dildo and pulled it free, replacing it with his fingers. God… hot, tight, and so very, very slick. Dana whimpered as she rested her hands on his legs, held in place by the pleasure that she was receiving from his fingers as they invaded her body.

She turned her feverish brown eyes to look at him, her face flushed with sexual excitement. "I want you to fuck me."

Triumph surged… and then broke.

"I don't have any condoms in here… they're all out in my car." And if he had to go all the way out there right now he might actually explode.

"I'm on the pill… I'm clean. Promise me you're clean." Dana turned towards him, unfortunately the move made it impossible for him to keep fingering her, but that disappointment was replaced by the hot promise of going bare-back in her pussy and the fantastic view of her breasts hanging down over his body. He reached up to cup them and she moaned, arching her back and thrusting her strawberry nipples towards him.

"I'm clean," he said truthfully.

With any other woman he would have never just trusted her word. But this was Dana; he already trusted her with Jordan, which was trusting her with more than his life.

She took his mouth with a hungry kiss, her bare body rubbing deliciously against his, nipples rasping over the wiry hair on his chest, cock cradled in the wet crack of her pussy lips. It felt incredibly. Her pussy juices coated the length of his dick as she rubbed herself against him, her clit bumping over the ridge of his head with every stroke of her hips. So wet… so slick…

Caressing and squeezing the handfuls of her breasts, he thrust upwards, feeling her shuddering moan as his movement increased the intensity of their connection. Leaning forward she kissed him again, adjusting their positions so that the head of his cock was snugged into the entrance to her body. It was heaven as she pressed downwards, the wet heat of her mouth echoing the snug haven of her pussy as it sucked in his cock.

Groaning, Rick's hips moved of their own accord, pushing upwards and into her as she sank downwards. She was so sloppily wet and prepped from the dildo that he speared her easily on one stroke, her walls tightening around him in pure feminine reaction. It was like a massage around his cock, her muscles stroking the entire length, and he squeezed her breasts hard as she ground down on top of him.

The dildo hadn't been nearly as large as his dick, but it had made the swift entry possible, and Dana pushed herself upwards on top of him and began riding him with passionate abandon. Her body rose and fell, breasts bouncing, pure sensual ecstasy written in every line of her body and the expression on her face.

"Rick… fuck… Oh you feel so good… god you're so big it almost hurts but it feels so good…"

"Oh fuck Dana… fuck yeah, ride me…" Although he'd never tried dirty talking himself he found that her own vocalizations motivated his, and he could tell that she liked hearing him by the way her pussy clasped him even tighter as he rasped his pleasure. "God you're so wet… so tight… fuck that's good… ride me sweetheart…"

He pinched her nipples and used them to guide her movements, up and down, up and down. The sound of her wet pussy slapping against his body was driving him wild. Her strokes were long and hard, all the way up to the head of his cock before slamming back down to take him fully inside of her. Every few bounces she would grind herself down against him, gasping and moaning as her clit rubbed hard against his pubic bone. It made his cock jerk inside of her every time she did that as her pussy lips rubbed all over his groin and the base of his cock was squeezed tighter and tighter.

It was as if every dirty thought from the time he'd moved in, every fantasy he'd ever had about banging a baby-sitter, every messed up inclination to hit on a younger woman, had suddenly come to life in the most incredible scenario possible. And now she was bouncing on his cock, riding him for all she was worth, and moaning and talking as filthy as if she was in a porno.

Knowing that he wasn't going to hold out much longer if he let her keep up the pace, Rick used her nipples to pull her downwards. She resisted a little bit, despite the pinch, as if she was enjoying the slight amount of pain that having her nipples pulled hard caused.

Wrapping one arm around her back, Rick flipped them over, his cock still embedded deep inside of her body.

Dana stared up at him with wide, shocked eyes.

"That was hot…" Her voice was breathy, almost disbelieving, and the awe in her face made him feel like a sex god.

Especially when her next response was to practically attack him. She pulled his lips down to hers, sucking his tongue into her mouth with all the fervent need of a woman in heat. Her hips pressed upwards, grinding her body against him, and he groaned as he fought his body's response, which was to immediately spill his load. He hadn't come this far just to lose control like a teenaged boy during his first time, even if that's kind of how he was feeling right now.

Instead he slid his arms down to hook underneath her thighs and then pulled them upwards, locking his elbows into the crook of her knees. Now her pussy was fully splayed, open and accessible to his marauding cock, her movements hindered by the positioning of her body so that he could take his time. Long, slow strokes interspersed with faster shallow ones, keeping the rhythm sporadic so that she was never quite sure what to expect.

Dana writhed beneath him as much as she was able, her kisses becoming more fevered, more impassioned as she cradled his head between her hands and then raked her nails down his chest.

"Rick… oh fuck… Rick… oh please fuck me… I need to cum… please Rick, fuck me hard… oh please…"

Hearing her begging for him was music to his ears. He could feel his balls tightening and knew he didn't have much time before he was going to fill her pussy with his jizz. Releasing her legs he slid his arms under her back and around her shoulders so that she could wrap her legs around his body, her ankles digging into his buttocks as they clenched and flexed, driving his cock into her hard.

Fingers clutching his shoulders, Dana threw back her head and screamed out his name as her pussy contracted, squeezing his cock so tight that he felt like she might actually break it off. He gasped, body heaving with a brutal thrust, but she was clenched so tight around him that she moved up and down with him, all of the force of the thrust driving down onto her clit and she sobbed and the walls of her cunt rippled.

"FUCK!" Rick buried his face in her hair, his hips flexing in minor increments back and forth as he flooded her body with hot cum, spurt after spurt squeezed out of him by the orgasmic contractions of her pussy. All the tension in his body seemed to drain out along with the hot froth, leaving him slumped on top of her as she shuddered and milked the last dregs of his orgasm from him.

They rocked against each other in silence for a moment, breathing deeply. Her hair smelled like raspberries. Her fingers stroked hesitantly along the back of his neck, playing with the little strands of hair there. They were pressed so tightly together that he could actually feel her shyness returning as if it was a physical thing.

And he didn't like that. He didn't want her to feel shy or awkward around him. For the first time in a long time, he knew exactly what he wanted.

Propping himself up on his elbows, he cradled Dana's head in his hands, fingers buried in her hair, and smiled down at her as she blushed and looked away then looked back up at him.

"If you're not doing anything next Friday," he said in a conversational tone, "instead of baby-sitting, would you like to go out to dinner with me?"

She smiled up at him, a brilliant smile of relief and joy, her face lighting up as she realized that there was going to be no awkward aftermath, no rejection. "I'd love to. Or you know… we could do tomorrow."

Rick grinned. "I'll see if I can find a new sitter. I have a feeling I'm going to need one."


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