The Babysitter

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Not to be read by anyone under 18, unless you’re a hot chick.

In which case my address is:

6669 NE 42nd St.

Point Place, WI (not really, but you can still drop by and see who lives there if you want)

The following is completely fictional. Any resemblance to reality is entirely coincidental. Contents of this story are merely creative license, not unlike a TV show or movie that uses real people in fictional settings and situations. However, if you do have video or pictures of events similar to the ones described below, feel free to forward them to me for closer examination. Feedback, comments, praise, criticism, death threats, nude photos, etc. can be sent to voodoojoe2000 at yahoo dot com (come on, you can assemble that into an actual e-mail address).

For personal use only. Feel free to distribute to friends, enemies, lovers, hopeful lovers, whatever, just keep my name and e-mail address on the story or I shall hunt you down and make you write the whole damn thing out by hand.

Celeb of choice in this story is Hilary Duff. The codes are (MF, cons, oral, mast, anal). Go fuck yourself and go read something else if you dislike those codes or want something more. Or better yet, write it yourself.

The Babysitter

By voodoojoe

“No no, don’t shoot,” Benjamin Jacobs pleaded, holding his hands up in surrender.

“Bang bang,” little Luca Comrie said.

“Oh, you got me,” Ben cried, grabbing his chest. Stumbling around on his knees, he made a show of gasping for air before toppling over and rolling onto his back. Coughing, he closed his eyes and let his tongue loll out of the corner of his mouth.

“Wow, impressive,” Hilary Duff said, laughing in the doorway.

“Mommy,” Luca said, rushing give his mom a hug.

“Were you a good boy?” Hilary asked Luca as she bent down to lift him up. “You killed your babysitter, so you couldn’t have been too good.”

“He was great,” Ben said, propping himself up on his elbows so he could look at Hilary.

Dressed in a little black dress from her night out, she was destined to feature heavily in his dreams when he got home. It went down to mid-thigh and hugged her curves like a (wet) dream with just enough cleavage to start a war in his head over whether he should drool over her tits or her ass.

“Well that’s good to hear,” Hilary said, giving Luca a tickle on his stomach and making him giggle. “But it’s time for bed, so say goodnight to Ben.”

“Good night,” Luca said, hopping down to give Ben a hug.

“Good night to you too,” Ben said, patting Luca on the back.

Grabbing Luca’s hand, Hilary pulled him towards the stairs. Ben let his gaze fall on Hilary’s ass in her tight dress for a moment as she climbed the stairs. When she turned the corner and disappeared down the hallway towards Luca’s bedroom, Ben finally allowed himself to stand up.

Getting to his feet, Ben adjusted himself. As a seventeen year-old male, watching Hilary’s ass as she climbed the stairs was more than enough to give him a partial chubby that was a bit uncomfortable in his standing position.

Glancing around, Ben saw his jacket sitting in a chair in the corner. He just lived next door so he didn’t even bother putting it on as he headed for the door to go home. He didn’t quite make it to the door though before Hilary saw him trying to sneak out.

“Don’t go yet, I still have to pay you,” Hilary said, looking down from the upstairs landing.

“Sure thing,” Ben said, milling around next to the door.

After making sure Luca was tucked in and on his way to dreamland, Hilary ducked into her room. She couldn’t believe what she was thinking, but when she bent over, she’d noticed Ben’s eye widen a bit as he stared at her cleavage. Then she’d felt his eyes glued to her as she went up the stairs.

She’d known Ben and his family ever since she and her husband had moved in next door to them a few years ago. It was obvious that Ben had a crush on her. Mike, her husband, had even joked on more than one occasion about how she should be careful wearing skimpy clothing around Ben or he might pass out.

Normally she mostly ignored Ben’s fleeting glances and felt flattered that a handsome guy was interested in her. But after a bit of a dry spell since her last failed reconciliation with her husband a couple months ago, seeing the hunger in Ben’s eyes had sparked something inside her that she couldn’t extinguish.

She wasn’t actually going to go through with it, he was still only seventeen and lived next door and she’d known him since he was just a kid. Yet there really wasn’t anything wrong with a fantasy. And, thanks to seeing him swimming both in his pool and hers over the summer, Hilary had a decently detailed picture of his body in her head. The only thing she didn’t have was what he looked like without swim trunks on, and already her brain was busy trying to come up with what his junk might look like.

“Snap out of it, Hil,” Hilary chastised herself as she imagine Ben dripping with water, the muscles of his arms rippling as he lifted himself out of the pool.

Taking one last look in the mirror and without even thinking she adjusted her dress to show a bit more cleavage. As she descended she saw Ben look up and then felt a twinge of arousal pass through her when his eyes widened reflexively when he noticed her tits.

“I hope you didn’t have to cancel a date or anything so you could watch Luca,” Hilary said when she reached the bottom of the stairs.

“No, I probably would’ve just spent the night playing video games with a couple friends,” Ben said, trying to look anywhere but at her chest.

“Well, thanks for giving it up for me, um, us,” Hilary said, grabbing her purse.

“No problem,” Ben said. “Luca’s a fun kid. Besides, I can probably skip my workout tomorrow with all the miles I logged chasing him around.”

“Trying to work off those holiday cookies, huh?” Hilary asked, her eyes flashing to Ben’s arms before digging her wallet out.

“Something like that,” Ben said, grinning.

“Shit,” Hilary muttered. “I forgot to get money. All I have is a twenty.”

“That’s okay, you can pay me later,” Ben insisted. “After all, I know where you live.”

“I’ll get your money tomorrow,” Hilary promised. An alternate method of payment flashed through her brain, but she quickly pushed it aside, though not before a mental image of her on her hands and knees with Ben behind her made an appearance.

“Whenever, I’m not in a rush to spend it or anything,” Ben said.

“You’re still free on Tuesday, right?” Hilary asked, putting her wallet back in her purse.

“I’ll be here and ready to walk the plank,” Ben said, making Hilary give him a weird look. “Luca wants to play pirates, so I’m sure you’ll be hearing him say ‘argh’ and ‘shiver me timbers’ a lot when you get home.”

“Sounds like fun,” Hilary said, laughing.

“What kid doesn’t love wearing eye patches and sword fighting?” Ben asked, grabbing and turning the doorknob.

“I’ll have your money tomorrow,” Hilary said as Ben opened the door. “If I don’t see you though, at worst, you can get it on Tuesday.”

“I’ll be here,” Ben said, closing the door behind him.

* * * * *

Yawning, Hilary lay in bed with the tv on, but she really wasn’t watching it. It was mostly a distraction to keep her mind off certain things, namely the boy next door. Every time her mind started to drift, it inevitably seemed to drift to thoughts of Ben doing certain things to her.

At first the thoughts were just picturing him naked; in her head he had a nice sized cock, of course. Then they’d proceeded to him actually using it on her. Before long Hilary had been soaking wet as she alternated between fighting her fantasies and actually embracing them a bit.

Grabbing the remote, Hilary flicked off the tv. She wasn’t quite in the mood to go to sleep yet as she reached over to the table next to the bed. Opening the top drawer she reached towards the back, behind the old magazines until her hand found the long, smooth object she was searching for.

Withdrawing the vibrator she debated whether she should go back for her lube but ultimately decided she was wet enough already. A couple hours of vivid sexual thoughts had left her pussy a virtual swamp and she knew from previous experience that she wasn’t going to be able to sleep until she took care of it.

Setting the toy on the bed next to her, Hilary tossed off the covers to reveal the pink lace camisole and shorts she was wearing as pajamas. Hooking her thumbs in her shorts, she lifted her butt and pulled her shorts down post her knees.

Lifting her knees, she grabbed the vibrator and brought it to her mouth. Giving the tip a little suck to transfer some of her saliva, a momentary image of giving Ben’s cock a similar little suck popped into her head and made her groan.

Moving the toy down to her crotch, she ran it along the length of her slit. Sighing, Hilary twisted the knob at base of the toy and felt it hum to life in her hands. Biting her lower lip, she pressed it against her clit and gasped as the sudden vibrations hit her.

Closing her eyes, she let the vibrations roll through her. Of course, it also let her mind wander and the image it churned up was Ben pressing himself against her back, his strong arms wrapping around her. His left hand wandered down to her pussy while his right pulled down the strap of her cami and pulled her breast out of the cup.

“Ohhh,” Hilary moaned quietly, pretending the hand cupping her tit was Ben.

Rather than fight it, Hilary rolled with it. In her fantasy Ben spun her around and threw her down on the bed. She watched in rapt attention as he pulled down his pants, her mouth watering as his cock sprang into view.

Wasting no time, Ben climbed on top of her. Reaching between them, Hilary grabbed hold of his cock, giving it a couple strokes and feeling the thickness of it in her hand before lining it up with her pussy.

Moving the vibrator down to her opening, Hilary pushed, penetrating herself in time with virtual Ben’s thrust into her. She was so soaked it slid into her pussy with ease and she arched her back, pretending to press her chest against his as she was filled.

With strong strokes Ben fucked her. Her fingers tweaked her nipple as the cock pumped into her. Each time she pulled the vibrator out to the end, she tilted the toy and ran the vibrating shaft along her clit before plunging it back into her cunt.

“Ohhh, Ben,” Hilary moaned to herself, picking up speed on her thrusts as her urgency grew.

Hunching her hips to meet the thrusts into her pussy, Hilary felt her orgasm barreling towards her. Her face contorted in pleasure and she fought to keep her noise down as she brought herself to the peak of pleasure.

Screwing her eyes shut tight, Hilary uttered a strangled cry as she came. She pushed the humming toy deep into herself and held still as her pussy clamped down on it. Her muscles seized up as waves of ecstasy washed over her.

Finally going limp, Hilary sighed and lethargically slid the vibrator out of her pussy. Twisting the knob, she turned it off, a satisfied smile crossing her face. Still picturing Ben, Hilary lifted the tip to her lips, using her tongue and mouth to clean her juices from the object that had just brought her so much pleasure.

“Mmm,” Hilary purred, feeling sleep finally starting to come to her as she tucked the toy back in its drawer.

* * * * *

“Ben!” Luca squealed, seeing his babysitter at the door on Tuesday.

“Hey, big guy,” Ben said, lifting Luca to set him on his shoulders.

“Oh, Ben, you’re here,” Hilary said, coming down the stairs in a leather skirt that came down to just above her knees.

“Wow,” Ben said before he could stop himself. “I mean, you look really nice.”

“Thanks,” Hilary said, smiling as she took in Ben in his jeans and t-shirt. “I got your money for you.”

“Cool,” Ben said, watching as she dug his money out of her purse.

“You know where all the numbers and stuff are,” Hilary said. “I don’t know when I’ll be home, so try to put him in bed by nine, but knowing you I’m sure you’ll finally put him down at ten and just tell me he was in bed by nine.”

“Busted,” Ben said, grinning.

“Okay, now I just need a kiss goodbye, and I’m out of here,” Hilary said.

“Sure thing,” Ben quipped, even leaning in to give her a quick peck on the cheek.

“I meant him,” Hilary said, pointing at Luca and trying not to show how much the joke kiss affected her.

“Of course,” Ben said, grinning as he knelt down far enough for Hilary to get her kiss from Luca.

“Okay, I’ll be back later,” Hilary said, heading for the door.

* * * * *

“You’re in a good mood tonight,” Bethany Carver observed as Hilary moved to the beat of the song in her seat. “Get lucky last night or something?”

“No, I guess I’m just in a good mood is all,” Hilary said, taking a sip from her drink.

“Ooh, cute guy checking you out,” Beth said, nodding towards a guy a couple tables over clearly making eyes at her.

“Not bad,” Hilary said, smiling at him.

“Ooh, here he comes,” Beth said, grabbing her drink and making herself scarce.

“Hi, I’m Alex,” cute guy said.

“Hilary,” Hilary responded as he slid into Beth’s vacated seat.

“Want to dance?” Alex suggested, holding out his hand and nodding towards the dance floor.

“I guess I could be persuaded,” Hilary said, taking his hand and letting him lead her out onto the dance floor.

* * * * *

“Want to catch a cab?” Alex asked over the music.

“Yeah, but I should do it alone,” Hilary said, regretfully.

After a couple hours of dancing, with more than a little bumping and grinding, Hilary was more than a little worked up. But she had to get home and she wasn’t about to take a strange man home, so as much as she liked Alex, she was definitely going home by herself.

“You sure?” Alex asked, frowning.

“Yeah, but give me your number and I’ll definitely call you,” Hilary said, holding out her phone.

On the one hand, he’d just put a couple hours into trying to get into her pants and it had clearly been a waste in that regard. On the other, he liked her enough that if she actually did call him, then maybe getting shut out right off the bat might not be the worst thing in the world.

“If you don’t call, I’m totally going to hold a grudge and never dance with you again,” Alex said as he put his number into her phone.

“We wouldn’t want that,” Hilary said, smiling as he handed her phone back to her.

* * * * *

“You look comfortable,” Hilary said, finding Ben stretched out on the couch watching tv.

“If I had a sandwich, then I’d really be comfortable,” Ben said, sitting up.

“Don’t sit up on my account,” Hilary said, taking a seat in the chair next to the couch. “So, how was my little man?”

“The usual,” Ben said. “We built a pirate ship out of cushions, wore eye patches, then we used cardboard tubes as swords until he ran me through a few times.”

“Sounds cute,” Hilary said, laughing.

While having a teenage boy as her go-to babysitter might sound weird to some, it actually worked out well. Ben was willing and able to play and do stuff with Luca that a girl might not. And Luca absolutely adored him, which was the most important part of it all.

“I should be getting home,” Ben announced.

“Actually, I’m kinda hungry,” Hilary said, kicking off her shoes. “That sandwich idea you had sounds pretty good.”

“Wait here,” Ben said, jumping off the couch.

“What are you doing?” Hilary asked loud enough for Ben to hear her on his way to the kitchen, but not loud enough to wake the kid.

“I’m making a sandwich,” Ben said, opening and closing the fridge and cupboards.

“Do you need help in there?” Hilary asked even though as she sat down her feet started to remind her that they’d just spend hours crammed into tight shoes and constantly moving.

“No, a sandwich is clearly within my abilities in the kitchen,” Ben said, using a little of this and a little of that to build his masterpiece.

A few minutes later, Ben came back with a plate with one sandwich perched on it. Cut down the middle into two triangles, he held the plate out for her. When she took half, he plopped back down on the couch and picked up the other half.

“Oh my god, this is really good,” Hilary said, shocked by what she was eating. At first she’d thought it was just going to be a regular ham sandwich, and at heart it was, but there was so much more to it and she was amazed that he’d been able to make it just with stuff she’d already had in her kitchen.

“Pair it with a nice beer, and it’d really be something, or so I’m told,” Ben said, making Hilary laugh.

“I might have to try that, but I doubt your mom would like it if I sent you home with beer breath,” Hilary said.

“Oh, they left for New Zealand this morning,” Ben said casually. “Dad’s got business and mom tagged along for fun.”

“That’s right, I remember your mom saying something about it a couple weeks ago when I came over to see if you could sit,” Hilary said between bites. “In fact, I think I’m supposed to check in on you to make sure you’re not throwing wild parties or sacrificing live sheep or whatever crazy thing your mom read about on Facebook this week.”

“I guess I’ll have to cancel the raid on the petting zoo and send the sacrificial altar back to Amazon then,” Ben said, dryly.

“You’re free to hang out here if you get bored and want to interact with people,” Hilary offered. “Though I’m sure you’re already planning to sneak your girlfriend in a few times.”

“Nah, she broke up with me before Christmas,” Ben said, shrugging his shoulders. “Seems she found herself a more exciting guy, or so she thought because a couple weeks later she tried to convince me to take her back. I, of course, told her to go fuck herself.”

“Good for you,” Hilary said. “I never liked her. She seemed like one of those girls that would expect you to do everything for her and then would get pissed if you even dared to ask if she’d bring you a cold drink while you were out working in the yard in hundred degree heat or something.”

“Not quite that bad, but close,” Ben said. “Your feet look like they hurt.”

“I’ve had worse,” Hilary said, lifting her feet and flexing her toes.

“If there’s one good thing that came out of dating Roberta, she was a pretty demanding taskmaster when it came to massaging her feet,” Ben said, nodding his head towards her feet.

“If you’re not offering, then too bad,” Hilary said, smirking as she turned in her chair. Draping her legs over the arm of the chair and couch, she put her feet in his lap. “I couldn’t tell you the last time my tootsies got massaged.”

“Next time I’m mowing your lawn in hundred degree heat, bring me a cold drink and we’ll call it even,” Ben said, pressing his thumbs into the sole of her foot.

“Ohhh, deal,” Hilary moaned as she leaned back against the other arm of the chair.

For the next ten minutes or so Ben worked on her feet, sending Hilary into a near tranquil state. He somehow managed to not only turn her feet into jelly, but unlocked a lot of the tension in her lower body just from massaging her feet.

“You’re hired,” Hilary said, completely relaxed when he finally let go of her left foot. “Though I think I made a grave mistake.”

“Which would be?” Ben asked, hoping he hadn’t pushed too far.

“I’m now on the verge of falling asleep and have no energy left to make it upstairs,” Hilary sighed. “I should have gone upstairs first and made you massage my feet up there.”

“Come on,” Ben said, standing up.

Before Hilary could ask what he meant, he slipped one arm underneath her knees and one behind back. Lifting her up, he moved around the chair and headed for the stairs. Hilary thought about telling him to put her down, but it solved the problem of having to walk up the stairs herself.

“Here we go,” Ben, said, using his foot to push open her bedroom door.

He’d seen her bedroom before, having been in the house a bunch of times, but he still felt a twinge of nerves as he carried her over the threshold. Crossing to the bed, he moved to the side and set her down on the bed.

“I’ll let you take it from here,” Ben said, his heart beating like a jackhammer as he looked down at her stretched out on her bed.

Maybe it was the months since the last time she had anything besides her fingers or vibrator between her legs. Or maybe it was all the close physical contact on the dance floor earlier. Or the foot rub. Or the ongoing fantasies from the last few days. Or maybe it was all of those things coming together into a perfect storm that kept her from stopping herself. Whatever it was though, she reached out and grabbed the back of Ben’s head and pulled him in for a kiss.

As Hilary’s lips met his, Ben was shocked, but he wasn’t about to stop her. Moving onto the bed on top of her he deepened the kiss. He really wanted to bring his hands into the equation to do a little groping, but he didn’t want to push.

For Hilary’s part, her brain was flashing warning signs, but her body refused to heed them. Once started, she couldn’t stop and as Ben hovered over her she moved a hand down to rest on his side, pulling him down on top of her.

Nervously, Ben pressed his crotch against hers, letting her feel his excitement. Feeling her moan into his mouth, Ben grew bolder and shifted his hips just enough to grind against her, getting another moan from the sexy MILF underneath him.

Feeling his cock pressed against her, Hilary felt her head spin in ways she hadn’t felt in years. She may have had a couple drinks at the club, but at the moment she was far drunker on lust and desire than on alcohol. Her brain was quickly being silenced and it stopped complaining altogether when she slid her hand even further down and cupped the front of his jeans, feeling his cock against her palm.

As if that was some secret signal that they had been waiting both of them immediately started pawing at clothes moments after Hilary’s hand came in contact with his crotch. Her hands went to his belt while his went for the buttons on her blouse. Both were nervous enough but Hilary’s experience had his pants open and her hand slithering into his boxers before he got halfway through her blouse.

Wrapping her hand around Ben’s cock, Hilary’s eyes opened wide. He wasn’t particularly long, but it was really fat, quite a bit thicker than even her seemingly optimistic fantasies over the last few days. Squeezing it, she gave it a tug, grinning as Ben moaned and quivered at her manipulations.

When Ben finally got her blouse open, Hilary clamped her thighs to his waist. Regretfully letting go of his cock, she rolled them over so he was on his back with her straddling his midsection. Sitting up, Hilary grabbed hold of her blouse and thrust her chest out as she pulled it down her arms.

“Shit,” Ben gasped, his eyes glued to her tits encased in a lacy light blue bra. He’d seen them in a bikini before several times, but the fact that she was on top of him, showing them to her in her bra, plus the prospect of seeing them without the bra, made it so much better.

Deciding to make him wait a bit more, Hilary reached down and found the zipper on the side of her skirt. Hilary didn’t want to have to get up for fear that it would make her come to her senses, so luckily the zipper on the skirt stretched the entire length of the garment and when it was all the way down she was able to pull it away and drop it to the floor next to the bed.

Unable to help himself, Ben’s hands slipped around behind her to grab hold of her ass. Hilary had worn a thong to avoid visible panty line so he was able to get skin-to-skin contact as he gripped her butt. He’d dreamt of fondling her ass since the first time he’d seen it in a pair of tight jeans, and now he had actually squeezing it.

“You’re wearing far too many clothes,” Hilary finally said, her hands reaching for his shirt.

As Ben sat up she lifted his shirt, pulling it off over his head. He wasn’t overly muscular or anything, but he worked out enough to have some definition in his chest and arms that if Hilary was being honest with herself, she’d noticed and admired before. And after tossing his shirt aside, Hilary ran the tip of her index finger along the contours of his six-pack.

Her finger finally reaching his waist, Hilary slid off of him. Pulling off his shoes and socks, she grabbed the legs of his pants and tugged until he lifted up and she was able to pull them off. With him in just her boxers, and his cock poking out of the flap, Hilary licked her lips as she got her first look at it.

Straightening up, Hilary pulled the straps of her bra down and slipped her arms out of them. Locking eyes with Ben, she hooked her fingers in the cups and peeled them down, exposing her tits to his hungry gaze. Pulling the bra down to her stomach she spun it around so the clasp was in front to make it easy to undo.

With Ben’s eyes trying to escape his head at the sight of her tits, Hilary moved her hands down to her waist. Slipping her fingers into the waistband, she pushed them down, exposing a patch of short brown pubic hair as Ben shifted his gaze down to her pussy.

“Turn around?” Ben asked when Hilary got her thong down to her knees.

Smirking, Hilary turned around, looking over shoulder to see the look on Ben’s face as he got an eyeful of the ass he’d been drooling over since she’d moved in. Feeling a little playful, she even bent forward at the waist, sticking her ass in the ass as she pushed her panties to the ground and stepped out of them.

“Oh god,” Ben groaned, seeing her pussy lips peeking out from between her legs and the tight little pucker of her asshole between the cheeks of her ass before she straightened up.

“Your turn,” Hilary said, turn around and looking at his crotch.

“Uh, yeah,” Ben said, hastily pushing his boxers down over his hips.

When his cock sprang free, Hilary locked her gaze onto it. Grabbing hold of his boxers, she pulled them the rest of the way off, leaving them both completely naked, nothing to hide even though she could tell he was fighting the urge to cover himself.

Crawling onto the bed between Ben’s legs, Hilary grabbed hold of his cock. She really wanted to feel him inside her, but the part of her that remembered what it was like to have sex with seventeen year-old boys knew that he’d never last.

So rather than climbing on top of him, Hilary took him into her mouth instead. Though she would’ve done it at some point anyway. She’d always enjoyed sucking cock, feeling it throb in her mouth and having a man at her mercy as she worked his cock.

As Hilary’s head descended towards his crotch, Ben felt his breath catch in his throat. Everything seemed to move in slow motion as Hilary wrapped her lips around the head of his cock. It was such a surreal experience that he damn near blew his wad before she even got much past the head into her mouth. Luckily though, he managed to hang on and push his need to the back burner for the moment.

Eyes wide open to record every detail, to the point that he was almost afraid to blink, Ben watched as Hilary’s pretty blonde head worked its way down his cock, taking several inches of his length into her mouth. It wasn’t his first blowjob by any stretch, but Hilary Duff sucking his cock was drastically different than having Cynthia McPherson give him head at a party. There was absolutely no comparison between his past girlfriends and Hilary, either in looks or experience.

“Such a beautiful cock,” Hilary murmured, pulling off of his cock for a moment as she let her hand stroke the shaft and distribute some of the saliva she’d left behind.

“Thanks,” Ben said, nervously. He’d never really thought of his cock as being special. He’d always worried it wasn’t long enough, though his girlfriends had never really complained.

Noticing the shortness of breath he was developing, Hilary dove back onto his cock. Working his cock into her mouth until he bumped against the back of her throat, Hilary pulled back slightly and grabbed hold of the shaft so she could bob up and down without worrying about going too far.

Setting out to make Ben come as quickly as possible, Hilary applied suction as she lifted up. Pausing with just the head in her mouth, she breathed in through her nose before pushing back down. Repeating the process, she soon had Ben hunching his hips in excitement.

“Uh, Hil, Hilary,” Ben stammered, feeling himself reaching the point of no return.

Not needing the warning, but still rather thankful for it, Hil merely increased her suction. Ben felt like she was going to suck his prostate out through his urethra, but when he opened his mouth, all he could do was squeak out a warning.

Feeling his cock pulse in her mouth, Hilary pulled back until just the head was still in her mouth. Sucking so hard her cheeks caved in, she literally tried to hoover the jizz out of his balls. When the first blast of cum exploded out of his cock, it splashed against her uvula, followed quickly by a second jet. Continuing to suck, Hilary moaned as her mouth was filled with her teenage neighbor’s seed.

“Fuuuuck,” Ben groaned when he was finally sucked dry and Hilary let his cock fall from her lips.

“Mmm,” Hilary said, tilting her head back and swallowing his load.

“Shit, that was amazing,” Ben gasped, shocked at what had just happened.

“That was just the start,” Hilary said, slipping off the bed.

Ben’s eyes followed her, drinking in the sight of her nakedness as she moved to the table next to the bed. Opening the drawer, she rifled around in it until she came up with what she was looking for. Lifting out the sleeve of condoms, she tore one off and dropped the rest on top of the table.

She was on the pill, and she trusted that he didn’t have any diseases, but she figured a condom might help his staying power. Even after removing a bullet from the chamber, she wanted to do whatever possible to make sure he lasted more than a minute or two inside her.

Ripping the foil wrapper with her teeth, Hilary pulled the condom out of the package. She’d thought she might have to suck his cock a bit more to get him hard again, but she wasn’t particularly surprised to find that staring at her body and the prospect of fucking her had put quite a bit of iron back in his pipe.

Taking hold of his hardening cock, Hilary lifted it until it was straight up and down. Placing the condom on the head, she unrolled the condom down the shaft. With him sheathed in latex, Hilary climbed back onto the bed, throwing a leg over his waist and settling on top of him, his cock pinned between their bodies.

Reaching out, Ben put his hands on her thighs. As she lifted up, he watched her grab his cock and drag it through her folds to moisten the tip a bit. Then as she aimed it at her opening, she eased down onto him, her pussy stretching to accommodate his girth.

“Ohhh,” Hilary moaned, feeling so full when she came to rest in Ben’s lap. He certainly wasn’t the longest guy she’d been with, but he was definitely one of the thickest.

Even through the condom, Ben could feel the heat and tightness of Hilary’s pussy around his cock. He was thankful for it though because it at least helped dull the intense sensations, though it did nothing to quell the mental side of things. After all, he was balls deep in Hilary Duff.

Leaning forward and putting her hands on Ben’s chest, Hilary lifted herself up, feeling slightly empty as his fat cock slipped out of her pussy. When she had barely more than the head still inside her, she paused before sliding back down, moaning quietly as she was filled again.

With her leaning forward above him, Ben’s eyes darted between the sight of his cock sliding in and out of Hilary’s pussy and the sight of her tits moving with her slow movements. Moving his hands from her thighs, he reached up and cupped her tits, squeezing them.

“You like my tits?” Hilary asked, pushing her chest against his hands.

“Oh yeah,” Ben said, lifting his hips to meet her thrusts.

“God, your cock feels so good in my pussy,” Hilary grunted, dropping down onto his shaft.

“Your pussy feels pretty good too,” Ben said, watching her bite her lower lip as she gradually picked up some speed.

“So big,” Hilary sighed, her eyes fluttering shut as she concentrated on the sensations.

Ben wasn’t the first guy she’d been with other than her husband, there was a guy she went on a couple dates with not long her separation, but that was it since her marriage. She was just too busy with her son and resurgent career to date much.

After being completely dormant for a couple months and being very hit-or-miss for a year before that, Hilary’s sex life really needed a jump start. And that was exactly what Ben, or more precisely, Ben’s cock, was providing. She could feel parts of her that she’d almost forgotten coming back to life as she bounced on top of him.

“Ohh ohhh ohhhhh,” Hilary moaned, feeling an orgasm starting to build inside her.

Picking up speed. Hilary was slamming down on Ben’s cock hard enough to make the room echo with the sound of flesh slapping together. Hilary was a little surprised how quickly her orgasm was arriving, but considering she’d basically been burning with need for days, she probably wouldn’t have been that surprised if she’d come the moment he’d entered her.

“Oh fuck me, Ben,” Hilary hissed, being pushed right to the brink.

“I’m not going to last much longer,” Ben warned. He was afraid he wasn’t acquitting himself that well, but he was a little overcome by watching Hilary enjoy herself so much.

“Not yet,” Hilary pleaded. She needed to come and just needed to hold out a little longer.

Trying desperately to focus on anything but Hilary’s body as she fucked him, Ben closed his eyes. Clenching his teeth, he tried to think about unpleasant things, but all that came to mind was the absurd amount of money Kim Kardashian made off a stupid game. That seemed to work though as he felt the urge start to abate a bit. Then he opened his eyes.

“Ohhhhh,” Hilary moaned, trying desperately to keep the noise down as she came.

Mouth hanging open, Hilary quaked on top of Ben as her body was assaulted with pleasure. A bliss like she hadn’t known in what at times felt like forever washed over her, making her feel almost lighter than air as she crested the peak.

And watching Hilary in the throes of climax was what pushed Ben over the edge. She looked so gorgeous that it was all he could take. Lifting his hips, he drilled his cock as deep into her clutching pussy as he could get it and let loose. With a low guttural growl, he tilted his head back and filled the condom, his body spasming with each eruption he made into the latex barrier.

“Mmmm,” Hilary sighed, head hanging down and leaning her weight forward on her hands still resting on his chest as she came down from her orgasm.

Feeling him start to soften inside her, Hilary lifted her leg and rolled off of him. Chest heaving, a grin spread across her face as she rolled onto her back. Bringing her feet close to butt, it lifted her knees into the air as she basked in the afterglow of sex.

“Where should I put this?” Ben asked, taking off the used condom.

“There should be a trash can next to the bed,” Hilary said, glancing over and being shocked to see his cock still three quarters erect.

Tying a knot in the condom to keep it from leaking, Ben leaned over the edge of the bed. Spotting the garbage can in question, he reached out to drop the used condom into it. Before he can let go though, he felt a hand stroke his cock.

“The power of youth,” Hilary sighed, feeling Ben’s cock come back to life in her palm.

“I should probably be getting home,” Ben said, his eyes darting to where Hilary was giving him a slow handjob.

“You could stay here,” Hilary offered. “I mean, if you wanted to.”

“If I stay, do you keep doing what you’re doing?” Ben asked.

“No,” Hilary said. When she saw the look of disappointment on Ben’s face, she giggled. “If you stay, you’re going to fuck me again.”

“Definitely staying,” Ben said. He reached for the condoms, but Hilary stopped him.

“I don’t think we’ll need that this time,” Hilary said, rolling onto her back and letting her legs loll open in invitation. “You should be able to last a bit without one.”

In case he hadn’t gotten the invitation, Hilary gave his cock a soft tug until he rolled over on top of her. Putting his left hand on the bed, he pushed himself up so he could reach between them to grab his cock. Taking aim, he pushed forward, plunging about four inches of his cock into her in one lunge.

“Uhhh,” Hilary groaned, her pussy being stretched by his cock once more.

Reaching up, Hilary put a hand on the back of Ben’s neck and pulled him down for a kiss. As his lips met hers, she parted her lips and let her tongue darted into his mouth. She moaned into his mouth as he pushed again, not stopping until his pelvis was pressed tightly against hers.

Pausing with every inch of his cock inside her, Ben marveled at the difference in the feel of her pussy without the condom. It was a cauldron of heat and after her orgasm she was drenched and he was glad he hadn’t tried to ride bareback for their first time, let alone without unloading one down her throat before that.

Pulling back, Ben planted both hands on the bed and started fucking her with the confidence and assurance that he’d lacked the first time. While he could count the number of women he’d been with on one hand, with Hilary being the thumb, he had enough experience with those others to know what he could do. And on his third erection with some of the novelty and idol-worship already worn off from the first time, he knew he could last for a bit.

So without worry of letting her down, Ben drove into her with force. When Hilary started to realize that she might have unleashed a monster, she grabbed his shoulders, hooked her legs around his waist and tried to hold on.

For a solid ten minutes he showed her what she’d not only been missing for the last year, but also for god knows how long before that. He was primal, yet caring, as he fucked her for everything she was worth. He paid attention to how she reacted and when she moaned he filed it away and repeated or came back to it later. If she didn’t respond the way he wanted, he moved on until he found something she did like.

After the first orgasm, she thought he’d done a good job and he could finish up and it’d be the best sex she’d had in ages. Then her second hit her and he showed no signs of slowing down. By her third, she was torn between wanting to feel him come inside her and never wanting him to stop.

Alas, as with all good things, their coupling was bound to end. Finally feeling stamina start to fray, he gritted his teeth, wanting to bring Hilary off one last time. He could tell she was getting close and he wanted to get there before he did.

Grabbing her legs behind the knees, he pushed them back and to the sides, opening her up as he slammed into her. The change lifted her ass slightly and changed the angle of penetration just enough to give Hilary that extra push she needed.

“I’m gonna come,” Ben said, feeling Hilary trip over into orgasm a moment before her loud moan gave him an audible cue.

“Come in me,” Hilary hissed, shaking with pleasure as she was rocked by orgasm.

Feeling himself passing the point of no return, Ben kept fucking her right until the last moment. Driving deep into her, Ben’s lips curled to show his teeth as the cum exploded out of his cock. Hilary could feel it splashing against her insides, driving her orgasm to even higher heights.

“Fuck,” Ben gasped, his body still spasming as he pulled his cock out of her.

“Fuck is right,” Hilary agreed, feeling that mix of euphoria and lethargy start to settle over her as her orgasm faded. “Get the lights?”

“Sure thing,” Ben said, yawning.

Slipping out of bed, Ben crossed the room to the light switch. Flicking it, the room was cast in darkness. Being a mostly strange room, he was careful on his way back, going slow with his arms out in front of him to make sure he didn’t trip over anything. When he found the bed, he slipped under the covers and quickly found Hilary’s form rolled against him. A moment later Hilary was completely out, sleeping soundly as Ben was a little slower drifting off next to her, though not by much.

* * * * *

Feeling the warm body next to her, Hilary awoke a little disoriented. It faded as memories of the night before flooded her brain. She filled with a mix of arousal and regret as she looked at her actions in the light of day. She’d taken advantage of a teenager, one who lived next door no less. And as much fun as it had been, and how very much she’d needed it, she couldn’t let it happen again.

But then, her hands started caressing the muscles of Ben’s stomach and rational thought started to disappear. Once more she was filled with thoughts about what else he could do with that cock and just how much she wanted to find out personally. After all, there were a bunch more positions they could try and she definitely wanted to suck him off at least once more.

‘Stop it, Hil,’ Hilary chastised herself, finally pulling her hand away from his body.

Knowing she needed to get out of there before she tried to wake him up in all sorts of fun ways, she tossed the covers aside. Slipping out bed, she grabbed her robe, leaving him sleeping in her bed as she headed across the hall to check on Luca.

* * * * *

“So then Ben jumped in the water and started fighting with the shark,” Luca said, giving Hilary a recap of the fun he’d had with Ben the night before.

“I won too, didn’t I?” Ben asked, appearing in the kitchen door.

“Ben?” Luca asked, wondering why he was there so early.

“It was late when mommy got home last night, and his parents are out of town, so Ben stayed over,” Hilary explained. “If you ask nicely, he might stay over again tonight.”

“Will you? Please?” Luca asked, excited at the prospect.

“Since you asked so nicely,” Ben said, his eyes glancing up to make contact with Hilary.

“Yay!” Luca said, raising one arm over his head as he chewed on a piece of bacon.

* * * * *

“So, what room am I sleeping in?” Ben asked, trying not to just assume there’d be a repeat of last night.

“The guest room,” Hilary said firmly. “What happened last night can’t happen again.”

“Okay, just friends,” Ben said, trying to hide his disappointment, and largely failing.

They’d spent most of the day exchanging furtive glances. There had even been a little kissing and groping on the couch while Luca took a nap, but when Ben had tried to slip his hand into her pants, Hilary had finally stopped him. After that they’d mostly behaved, even though she’d had approximately fifty thousand dirty thoughts about him between when he’d agreed to stay over and when she’d put Luca to bed for the night.

“Just friends,” Hilary agreed even though even she had trouble figuring out whether she meant it.

“Since you’re letting me stay here, the least I can do it make breakfast in the morning,” Ben said. “Any requests?”

“If you can make pancakes, you’ll be Luca’s hero, even more than you already are,” Hilary said, laughing.

“Pancakes it is,” Ben said, turning and heading for the guest room, and Hilary’s head turned to watch him even as she scolded herself for it.

* * * * *

Watching tv, Hilary’s brain wasn’t into it though. Her thoughts kept drifting down the hall to the stud sex machine she had stationed there and for some reason resisted taking advantage of. But the harder she tried to ignore him, the more her brain brought him to the forefront.

Feeling hungry, Hilary slid out of bed. Donning her robe, she snuck down the stairs. Seeing a light on in the kitchen she guessed she wasn’t the only one that had the same idea. Entering doorway though, she stopped in her tracks.

Standing in front of the sink in nothing but a pair of boxers was Ben. A glass of milk in his hand, he lifted it to his mouth. As he tilted his head back to drink his milk, Hilary’s eyes fixed on his abs and once more felt a little overwhelmed by lust.

“Oh, hey,” Ben said, jumping a little when he turned and saw Hilary standing there. “Hope you don’t mind, I was thirsty.”

“Make yourself at home,” Hilary assured him.

“So, you couldn’t sleep either?” Ben asked, making small talk.

“I was hungry, so I thought I’d come down and get a snack,” Hilary said.

“Shit, that’s cold,” Ben squealed as he dribbled milk out of the corner of his mouth and onto his chest.

Without thinking, Hilary grabbed a towel. Dabbing at the milk, Hilary suddenly became very aware of his proximity. As she dabbed lower, memories of him on top of her driving her to orgasm after orgasm filled her brain. By the time she finished cleaning him up, the temperature in the kitchen had shot up twenty degrees.

Unable to take any more, Hilary grabbed Ben and yanked him down for a kiss. Acting on autopilot, her hands went for the sash of her robe. Pulling it open, she pushed it off her shoulders, leaving her wearing just a silky nightgown with nothing underneath.

“I thought you said it couldn’t happen again?” Ben asked as her hands went for his boxers.

“Do you really want to stop?” Hilary asked, slipping her hand into his boxers and finding him already hard.

“Fuck no,” Ben grunted, lifting her up.

As Hilary’s legs hooked around his waist, he moved to set her on the edge of the counter. Slipping his hands underneath her nightgown and finding her bare pussy, Ben groaned in anticipation. When Hilary pulled his cock out of his boxers, he moved his hands to her thighs so she could aim it at her pussy.

“Ohhh, yeahhh,” Hilary moaned as he pushed forward, finding her more than wet enough to accommodate his size.

Remembering that they were in the kitchen and couldn’t take forever, Ben didn’t waste time on niceties. He barely paused when his cock was fully seated in Hilary’s pussy, immediately pulling back. When he drove forward again, Hilary moaned and used her heels to help pull him into her.

With a frenzy born from a combination of needing to be quick and releasing some of the pent up desires that hadn’t been vented last night or had built up during the day, they humped against each other. Leaning forward, Ben buried his face in the crook of Hilary’s neck, kissing and licking at the skin of her neck as he plunged his cock into Hilary’s fiery cunt.

“Fuck me, oh god, fuck me,” Hilary hissed into Ben’s ear, clutching his shoulders as she got lost in what they were doing.

Hearing Hilary begging him to fuck her spurred Ben on to give her what she wanted. It was so hot to hear her get so dirty and Ben wrapped his arms around her. Putting one hand between her shoulder blades, the other one went to the small of her back and held her tight against him as he drilled into her twat.

“That’s it, baby, fuck me,” Hilary moaned.

Going hard and fast, Ben screwed her with a fury that took her breath away. She wasn’t sure whether he was capable of being slow and gentle after two rather savage attacks on her pussy, and she couldn’t really decide whether she wanted to find out. The almost feral nature of his fucking was really working for her and slowing him down could ruin it.

“Fuck fuck fuck,” Hilary grunted, feeling an orgasm about explode inside her.

Trying to ignore his own impending climax, Ben barely missed a beat as he lifted her a couple inches off the counter. Moving his hand from the small of Hilary’s back, he slipped it underneath her, grabbing her ass through the fabric of her nightgown that she was sitting on. Setting her back down, trapping his hand in the enviable spot between the counter and her remarkably firm, yet fleshy posterior.

“So close, Ben, sooo clooooossseee,” Hilary moaned, burying her face in his neck as she was pushed right to the brink.

Biting down on his shoulder to muffle her screams, Hilary reacted to his ferocity with an orgasm to rival it. Her body shook so hard she literally bounced on the counter, bringing more than a little pain to the hand trapped underneath her. It was so violent, she felt like she was going to unravel as the pleasure shot through her.

With the pain in his hand helping distract him, Ben somehow managed to ride out Hilary’s orgasm. Keeping himself buried inside her, Ben used the hand on her ass to support her as he straightened up, lifting her as he went. Turning, he carried her out of the kitchen and up the stairs to bed.

He figured worst case scenario once he got there was that she gave him a handjob or something and sent him back to the guest room for the night. Actually, worst case would have been that she sent him back without any satisfaction at all and left it up to him to do it on his own, but he wasn’t worried about that. The best case scenario though was that she got him off, then let him fuck her some more, which is what wound up happening.

After setting her down so he could close the door behind him, Hilary had dropped to her knees and taken him into her mouth. Even after the partial rest with minimal movement inside her as he carried her upstairs, it had only taken a couple minutes for Hilary’s magic mouth to use his cock as a large straw to drink the cum straight from his balls.

Then when he’d expected to be sent back to the guest room, Hilary had reached down and pulled off her nightgown instead. Turning around, she’d climbed onto the bed on all fours and looked back at him and wagged her ass in a way that could only be considered an invitation.

Rather than take her up on what she’s obviously expected, Ben had surprised her. Instead of moving in behind her and stuffing her full of cock, he dropped to his knees and grabbed the cheeks of her ass with his hands as he jammed his face against her ass.

“Ohhhh,” Hilary moaned as Ben’s tongue shot out and flicked at her clit.

While he wasn’t the best pussy eater ever, he was definitely better, and certainly more willing, than the guys she’d been with at that age. Of course, the real shock came when Ben was dragging his tongue along the length of her slit to poke at her hole before moving back to her clit. She’d shifted unexpectedly and he overshot his target, his tongue winding up stabbing at the tight pucker of her asshole before either of them realized it.

Ben had quickly moved back to what he was doing, but the damage was done. Even through the two orgasms Ben brought to her with his tongue, Hilary’s anus still resonated with the ghost of his tongue and it wasn’t until he’d finally shoved his cock back into her pussy that their little foray into salad tossing was pushed from her brain.

* * * * *

“Fuck me, yeah, fuck me,” Hilary hissed as Ben fucked her from behind on Thursday afternoon.

After giving in not just once, but twice, and having her will shattered pretty convincingly both times, Hilary had pretty much given up on behaving herself. Upon waking up next to Ben, she’d found a nice hard cock tenting the sheets and after a brief tug-of-war in her brain, she’d climbed on top of him and woke him up by riding him like a rodeo champ.

Currently though, Ben had Hilary bent over the back of the couch stuffing her full of his glorious cock. Ben had come back from school to find that Luca was taking a nap and decided to have some fun. Grabbing her, he’d bent her over, flipped her skirt up, pulled her panties aside and shoved into her.

With one hand on the back of the couch to support her, Hilary used the other to reach underneath her. Finding her clit, she stroked it as Ben fucked her. The combination was electric as the danger of fucking the teen boy from next door while her son slept right upstairs did wonders for her.

They say that familiarity breeds contempt, but the opposite seemed to be at play. The more familiar Hilary got with Ben’s cock, the more she wanted it. And it didn’t help that the more familiar he got with her body, the better he was able to give what she needed.

“Ohhh come on, Ben, fuck my tight little pussy,” Hilary pleaded, her finger a blur on her clit.

Wanting to make sure they finished before Luca could wake up, Ben didn’t try to slow down. If anything, he went faster, driving into Hilary’s pussy hard enough to make Hilary gasp each time his pelvis slapped her ass at the end of each thrust.

“Fuck me so good, make me come,” Hilary gasped, forgetting everything but way her pussy was being savaged over and over.

“I’ll make you come,” Ben promised, gripping her hips and pulling her back onto his cock. “Then I’m going to come so deep inside you you’re going to feel it in your throat.”

“Ohhhh, do it,” Hilary demanded, looking over her shoulder and giving Ben a look so loaded with need that it almost pushed him over the edge by itself.

Getting a handle on himself, or at least enough to hold his orgasm at bay a little longer, Ben went with short, fast strokes. Viciously impaling her, he quickly had Hilary mewling as her orgasm rushed towards her. Finally achieving release, Hilary bit her lip to stifle her scream as she came.

Feeling Hilary’s pussy clamp down on him was all he could take. Driving deep into her cunt he snarled as the cum erupted out of his cock. Growling through gritted teeth, his hips jerked as spurt after spurt exploded into Hilary’s spasming pussy.

When he was finally empty, Ben pulled out. Seeing the white froth of the mixed fluids start to collect at the entrance of Hilary’s pussy, he pulled her panties back into place to help catch them before they dribbled all over the floor.

“I think I’m going to go take a shower,” Hilary said, standing up.

“I’ll entertain the munchkin if he wakes up before you get back,” Ben said, nodding.

* * * * *

“Want more?” Hilary asked Ben, holding up the last pork chop.

“If you don’t want it, sure,” Ben said, holding out his plate. “For some reason I’m really hungry tonight. I must have worked up an appetite today.”

“Must be Luca’s fault for making you chase him around,” Hilary said, blushing.

“That must be it,” Ben said, smirking as he took a bite of his salad.

“Better eat up then, because I think he might want you to chase him around again tonight,” Hilary said, making eye contact with Ben and hoping he could figure out what she really meant.

* * * * *

“Ohh ohhhh ohhhhhhh,” Hilary moaned, grabbing a handful of Ben’s hair and bucking her hips as his tongue worked on her pussy.

After Luca had crashed, draped across Ben while watching tv, Hilary had picked him up to take him to bed. When Hilary had gone to her room, she’d been ambushed by Ben. Clothes were quickly removed and Hilary shoved onto her back so Ben could feast on her pussy.

Clamping her thighs against his ears, Hilary yanked on Ben’s hair as she humped against his face. Squirming on the bed, she twisted onto her side, taking Ben with her. When he eased his middle finger into her, she groaned and responded by pulling on his scalp even harder and pushing his face even tighter to her crotch.

“There, there, ohhhh,” Hilary squealed, clenching her legs tightly around his head as she detonated.

One thing Ben had learned was that if a guy was willing to eat pussy, a girl was far more likely to let him keep fucking her. So few guys his age seemed willing that whenever he went down on a girl for the first time it inevitably tended to be the first time anyone had done it to her. Then even after breaking up with girls, a couple of them were always willing to be friends with benefits because they knew he’d make it worth it.

And Hilary was about three days into finding out why. She knew there couldn’t be a relationship between them and there wasn’t a future, but still… Just looking at him ignited her loins, and then when she broke down and let him near her loins everything else ignited.

Part of it was the fact that he was a new lover and everything was still fresh and interesting. Part of it was also that he kept legitimately blowing her mind. He had the abundance of energy and recovery power of a teenager and she was old enough to truly appreciate it, as opposed to when she was seventeen herself and thought every guy would be able to get multiple erections and go for hours.

Hell, even when she was seventeen she would’ve killed for a guy that could do that. A week ago she would’ve killed just for the abundance of energy. It was just terrible luck that when she finally managed to find one, he was ten years younger and still in high school.

But as Ben pushed her thighs together while she was on her side and aimed his cock at her dripping pussy, Hilary decided decisions about the future could wait. After wandering through a desert, she’d stumbled into a torrential downpour and she wasn’t ready to come in out of the rain quite yet.

* * * * *

“Uhh uhhh uhhh,” Hilary grunted as Ben pinned her against the shower wall and slammed into her pussy.

After fucking in several different positions, and Ben depositing his load all over Hilary’s tits, she’d suggested they hit the shower. And after a little soaping and a lot of groping, Ben had lifted her up and pressed her against the wall to fuck her underneath the steamy spray.

“Oh god, you’re killing me,” Hilary groaned, meaning it in the best possibly way.

She wasn’t sure how much more she could take, at least for the night. A good night’s rest and maybe the next day and she might change her mind, but for the moment she was really feeling tired, and her pussy was really feeling all the abuse he’d dished out the last couple days.

“Make me come and then I’ll finish you with my mouth,” Hilary promised.

“Pussy feeling sore?” Ben asked, feeling rather proud that he’d outlasted her.

“A little,” Hilary answered.

“Then I guess I need to finish you off,” Ben said, grinning.

A moment later the hand he’d put on her ass to help hold her up shifted slightly. Dragging his middle finger through the crack of her ass, he ran it over the tight pucker of her asshole. Before she’d even realized what was happening, he pushed forward, easing the tip of his finger into her asshole.

He’d read about it on the internet and even tried it on a couple girlfriends. One had thought it was weird and wouldn’t let him do it again, but the other really liked it. Whenever he stuck his finger in her ass while fucking her, she went off like a bottle rocket. He’d thought of doing it to Hilary before, but frankly, he had her on a bit of a pedestal and he didn’t want to do anything she might not like. But with her in need of being finished quickly, now was the time to test the waters if there was ever going to be one.

“OOOOOOOHHHH,” Hilary screamed as the sudden penetration of her asshole pushed her over the edge.

With her in the throes of orgasm, Ben slowed down his thrusting but didn’t stop. Instead he adjusted his grip on her ass, pushing his finger even deeper in the process. Feeling the way her anus was clenching and gripping his finger, he really wanted to see what else she’d let him put in there.

“Ohh gawwwddd, where did that come from?” Hilary sighed as she came down from her peak.

“You said you wanted to come quickly,” Ben said, shrugging his shoulders as he pulled out of her and eased her down onto shaky legs.

“Well, it worked,” Hilary said, reaching out and turning off the shower.

“I hate to be rude or anything, but…” Ben said, glancing down at the raging hard on sticking out from his body.

“Oh, right,” Hilary said, dropping to her knees on the tile floor.

Wrapping her hand around his cock, she took him into her mouth. She could taste her juices all over his cock. She’d never been with another woman, and never really was interested, but she’d always loved the taste of herself on a hard cock. It meant that it had just been inside her and usually meant that good things were happening, or had just happened.

Bobbing up and down on his cock, Hilary let her free cup and caress his balls. They were so big and heavy and really wanted to drain them. She wanted to feel his cum swimming around in her stomach and she sucked his cock like she was trying to turn him inside out.

“Fuck,” Ben grunted, putting a hand on the back of her head and splaying his fingers.

Holding her head in place he started to push forward, fucking her mouth with short, sharp thrusts. Her lips were stretched tight around his shaft and he watched her pretty blonde head working up and down his cock. It was a tough combo to beat and it rapidly took its toll on him.

“Uh, Hil,” Ben gasped, feeling himself reaching the brink. She’d swallowed the couple times she’d finished him off with her mouth so he had an idea what to expect, but he still wanted to at least warn her before just basting her tonsils with his man goo.

Ignoring his warning, Hilary kept working his cock. Feeling him start to throb in her mouth, she pulled back until just the head was still in her mouth. When the first spurt gushed into her mouth, she moaned and swallowed his cum as quickly as he could give it to her.

“Wow,” Ben said, his chest heaving as she pulled her mouth off his cock and nuzzled it against her cheek.

“Come on,” Hilary said, grabbing Ben’s hand and pulling him out of the shower.

Grabbing a couple towels, Hilary tossed one to Ben. After making sure they were dry, Hilary pulled him into the bedroom. Nodding towards the bed, she turned off the lights while he pulled the covers back. Slipping into bed next to him, Hilary cuddled up next to him, draping a leg over his thigh and an arm across his chest.

* * * * *

“He’s got a mind of his own,” Ben said, shrugging as Hilary shook her head in disbelief.

She’d woken up to find him pressed against her back, his cock hard and pressed firmly into the crack of her ass. After what felt like a couple dozen boners that she’d taken care of for him over the last few days, though it was probably closer to ten, he was still a human divining rod.

“Well put it away,” Hilary said. She regretted letting it go to waste, until she sat up and her nether regions screamed at her for overusing them. All in all though, if she was going to be in pain, it was about the best she could have asked for.

“Don’t worry, my parents come home tonight, so I’ll be out of your hair,” Ben said, reaching out and tracing small looping lines along her lower back.

“It’s probably for the best,” Hilary sighed. “We should probably try to go back to the way things were before things go any further and someone gets hurt.”

“My brain knows you’re right, but it’s hard to do some of the things we’ve done without feeling something that goes beyond purely platonic,” Ben said, shrugging.

“I’m too old for you anyway,” Hilary insisted. “You gotta find that lucky girl your own age.”

“I tell you what, any time you need your battery recharged, I’ll be here for you,” Ben said, grinning. “It’ll be tough, but I’d be willing to make that sacrifice.”

“I bet,” Hilary said, grabbing her pillow and hitting him on the head with it. “Now come on, we need to be up and about before Luca.”

* * * * *

“Come on,” Hilary said, beckoning Ben with her hand. After getting home from school, Ben had started watching tv with Luca so she figured they could leave Luca watching cartoons for a couple minutes.

“You rang?” Ben asked in a fake British accent, giving her a short bow.

“I was just thinking that if this is our last day, then maybe I should do something special,” Hilary said.

“One more for the road?” Ben asked, eyebrow raising as he started working out the logistics.

“Its Luca’s nap time, so it could be our last adult fun time,” Hilary said, grinning. “So I’m going to give myself to you. Anything you want to do, I’m completely at your whim.”

“Wow, anything is an awful lot of ground to cover,” Ben said, already knowing what he wanted.

“I mean it, anything,” Hilary said, the word ‘anything’ practically dripping with meaning.

“Then put him to sleep quickly,” Ben said, grabbing Hilary’s hand and pressing it against his crotch.

“Nap time,” Hilary announced, squeezing Ben’s rock hard cock before going to collect her son.

* * * * *

“Wow, you sure know how to greet a girl,” Hilary said as she entered the guest room and found Ben waiting for her sitting on the edge of the bed buck naked and his cock pointing straight at the ceiling.

“Don’t want to waste time getting naked,” Ben said, grabbing Hilary’s hand and pulling her towards the bed.

As she stood next to the bed with his thighs on either side of her legs, she raised her hands and let him lift her shirt off over her head. Next he tugged her pants down and she stepped out of them, leaving her clad only in bra and panties.

“Lay down,” Ben said, nodding towards the spot on the bed next to him. “Face down.”

Doing as he said, Hilary climbed onto the bed on her hands and knees and then settled down so that she was laying on her stomach with her feet hanging off the end of the bed. Lifting her head, she looked back as he slipped off the bed.

“You won’t be needing these,” Ben said, hooking his fingers in the waistband of her panties and tugging them down.

“I hope not,” Hilary said, lifting parts of her body to help him remove her panties.

“You said anything I want, so I want to worship the one part of your body I really haven’t gotten to yet,” Ben said, leaning forward and grabbing and squeezing the cheeks of her ass just in case she hadn’t figured it out yet.

“Um, okay,” Hilary said, shocked though she probably shouldn’t have been.

Looking back it kinda made sense. While the time he’d licked her ass had clearly been an accident, she’d felt his eyes on her ass a lot in the past and his hands had spent a lot of time on her ass the last few days. Plus there was the finger in her butt last night. But was she willing to go through with what he apparently had in mind?

As Hilary was debating whether she could do it or not, Ben was pulling apart the cheeks of her ass. The tight pucker of her asshole beckoned him from between them and bent in for a closer look. With her ass right in his face, he darted his tongue out and took an experimental lick of her asshole.

“Ohhhhh,” Hilary moaned at the sudden, though not really unexpected maneuver.

Taking another, longer lick of Hilary’s asshole, Ben decided he liked it. He’d never licked a girl’s ass before, on purpose any way, but as an ass man he’d long been curious about it. And now with Hilary promising to let him do anything, he’d figured why not try it with the ass he coveted most?

As Ben’s tongue played at her back door, Hilary was filled a mix of feelings. It felt kinda weird, but also really good. She’d never known her asshole could feel that good and the more Ben licked, the better it felt until she was groaning and pushing her ass back against his probing tongue. Maybe she could let him keep going for a little longer.

Pulling away from Hilary’s ass, Ben ignored the pleading groan as he rubbed around her anus with his thumb instead. Pushing slowly but firmly, he watched with rapt attention as Hilary’s asshole opened up to swallow his thumb.

“Shit,” Hilary gasped, his thumb feeling huge in such a tight hole.

“Does it hurt?” Ben asked, not wanting to hurt her.

“A little,” Hilary said through clenched teeth as she tried to get used to having something as big as his thumb in her ass.

“Want me to take it out?” Ben asked, slowly easing it back.

“Nooo!” Hilary gasped, causing him to push back in to the knuckle. “I mean, I promised you anything, so you should do what you want.”

“Okay,” Ben said, smirking as he realized she liked it more than she was admitting.

Moving his thumb inside her, Ben worked just a tiny bit in and out of Hilary’s ass. It gripped and clenched at his digit, welcoming it inside her and reluctant to let it go. Pushing deeper, he further forward and lightly kissed the small of Hilary’s back.

“Mmmm,” Hilary purred as kissed along her spine until he reached the top of her butt crack. His little fluttering kisses complemented the movements of his thumb in her ass.

“Ready for more?” Ben asked, wiggling his thumb and making her squirm.

“Sure, I guess,” Hilary said, wondering what his next step would be.

Easing his thumb out of her ass, Ben reached his hand under the pillow where he’d secreted her vibrator. They’d used it on her clit while he fucked her one night, so when she’d been putting the kid to bed he’d grabbed it and the lube. He’d figured that at absolute worst they’d spend the time going down on each other and he’d get to fuck her with it while he ate her pussy. But at the moment, he had another hole in mind for where to put it.

Holding up the vibrator, Ben smeared lube along the shaft. Satisfied that it was nice and slick, Ben used his free hand to pull her cheeks apart. With her asshole slightly gaped from his thumb, he pressed tip of the vibrator against the center and pushed.

“Uhhh,” Hilary grunted as he pushed the toy into her ass. It really wasn’t much thicker than his thumb, but it was so much longer and even though she’d felt the same vibrator in pussy a bunch of times, it felt way bigger in her ass.

“Feel good?” Ben asked, eyes fixed on the purple toy jutting out of her perfect ass.

“Kinda,” Hilary said. It didn’t hurt quite as much as she would’ve thought, and it felt sorta good, but mostly is just felt really weird as he slowly started to fuck her ass with the vibrator.

“Lift up,” Ben said, slipping a hand underneath her and applying just pressure on her stomach to get her to raise up onto hands and knees.

Moving further up the bed, Ben slid his right hand from Hilary’s stomach to her chest. As his left hand continued pumping the toy into Hilary’s ass, his right cupped one her tits and tweaked the nipple with his thumb.

“Oooooh,” Hilary cooed as the pain started to fade and the pleasure started to increase.

“Ready for my cock?” Ben asked, bending down to kiss her shoulder.

“Um, I, uh, guess,” Hilary said, suddenly nervous. While the vibrator was starting to feel really good, his cock was so much thicker and the idea of it invading her back door was downright scary.

“Okay then,” Ben said, pulling the vibrator out of her ass.

Looking at the toy, glistening in the light from the lube and her ass juices, Ben was torn on what to do with it. He didn’t want to just drop it on the bed and let that stuff mess up her sheets and everything but he didn’t have anything to wipe it off with.

“Here, clean this while I get ready?” Ben asked, handing Hilary the vibrator.

Taking the proffered toy, Hilary looked at it. Having sucked her juices off the same toy dozens of times, Hilary didn’t even think as she brought it to her mouth. Parting her lips, she took it into her mouth, tasting a different flavor than she was used to.

“Oh shit,” Ben gasped, stopping mid-squeeze on the tube of lube as he watched Hilary go ass-to-mouth with her vibrator.

“Huh?” Hilary asked, then looked down at the toy a couple inches into her mouth and remembering where it had been.

“That is so fucking hot,” Ben groaned even as Hilary started to blanch.

“Really?” Hilary asked, pulling the toy out of her mouth. Actually, outside of the slightly different flavor, it didn’t taste that bad. It didn’t really taste good either, it just tasted different.

“Oh yeah,” Ben said, smearing lube along the length of his cock.

“Hmm,” Hilary said, dragging her tongue along the shaft of the vibrator. Seeing the effect it had on Ben, and that it really wasn’t that bad, she made a show of cleaning it with her tongue and mouth.

“Ready?” Ben asked, finally moving in behind Hilary.

When she nodded, he grabbed hold of his cock and pointed it at the center of her gaping asshole. His heart was beating like a jackhammer in his chest as he found himself facing the wide open gates to Hilary’s perfect ass.

While he’d fantasized about anal, and soiled more than a few tissues while thinking about fucking Hilary’s ass, he’d never actually done it. As an ass man he’d watched a ton of porn and frequented several of those sex story sites so he knew he needed to be really gentle. But kinda like the first time he ever had sex, he was still really nervous as he pressed the head of his cock against Hilary’s asshole.

“Fuuuckkkk,” Hilary grunted, her eyes shooting open wide as the head of Ben’s cock pushed past her sphincter.

Her anus hadn’t presented much of an obstacle after the gradual stretching he’d given her with his thumb and then the vibrator, but it still hadn’t quite prepared her for just how thick his cock was. Yet, thanks to that stretching, she wasn’t screaming and howling in pain like she would’ve thought even ten minutes ago. In fact, as he started making teeny tiny thrusts into her ass, pushing just a little more of his cock into her with each thrust, the fire that she’d felt at the initial shocking penetration was slowly being replaced by a sort of tingle that felt sorta good.

Feeling the insane tightness of her asshole, unlike anything he’d ever felt before, even compared to when he’d fucked Jayne Schwartz and taken her virginity. He’d thought Jayne was tight, but that was nothing compared to the constriction he was trying to work through. It almost felt like he was slowly feeding his cock to a hungry anaconda or something, feeling it gripping and rhythmically squeezing him as inch after inch slowly disappeared into its mouth.

Finally reaching bottom, Ben pressed his pelvis against the firm globes of Hilary’s ass. Hilary groaned, unable to believe that she’d managed to take every inch of him up her ass, but the large throbbing chunk of man meat parked what felt like a mile into her bowels made it clear that she had.

Gripping Hilary’s waist and hips, Ben slowly pulled back, watching his cock slide a couple inches out of her ass. Wanting to be super gentle, he paused a beat before slowly pushing back in. It was agonizing, but he wasn’t about to just go hog wild on Hilary’s ass or anything.

“Uhh,” Hilary half grunted, half moaned as Ben’s pelvis bumped against her butt cheeks with each short thrust he made. He was still going slow enough that there wasn’t much power behind them, but it was still enough to remind Hilary of what they were doing.

Pushing into Hilary’s ass, Ben felt Hilary actually push back to meet him. Hoping it was a signal that she was getting into it, he went a little faster on his the next thrust. When she moaned in what definitely sounded like pleasure, he gave her another thrust about the same speed.

“You like that?” Ben asked when she moaned again, even clearer this time.

“Yeah,” Hilary said, surprised by what she was feeling. The pain, while not completely gone, was reduced to the type that actually seemed to complement the pleasure shooting through the nerve endings in her anus.

“Want me to fuck you harder?” Ben asked, giving her the first really hard thrust into her ass.

“Ohhhh god, yeah,” Hilary gasped as her lower body lit up like a Christmas tree as his body slammed into hers.

With Hilary’s permission, Ben opened things up a bit. Moving at a solid pace, though not even close to as fast as would’ve worked her pussy, he fucked Hilary’s ass, watching those marvelous cheeks ripple with the force of his thrusts. Each lunge was accompanied by the slap of their bodies meeting followed by increasingly loud moans from Hilary.

“Ohhh, fuck my ass,” Hilary moaned, meeting each of his thrusts with one of her own.

“Keep saying that and you’re going to make me come,” Ben warned, hearing her beg him to fuck her ass doing wonders for the mental aspect of sodomizing Hilary.

“Oh yeah? Fuck my ass, Ben, fuck it hard,” Hilary hissed, feeling him fuck her even harder in response.

“I’ll fuck it so hard you won’t be able to walk later,” Ben snarled, pulling on her hips until their bodies slapping together so hard the room echoed.

“Fuck, uhh, me,” Hilary grunted, slipping a hand underneath her to frig her clit.

Letting his eyes rove over her body, he started with where his cock was stabbing into the super tight confines of her ass. From there they ventured along the contours of her lower back and settling for a moment on the way her arm moved as she fingered her clit. After that it was onto her breasts swinging like pendulums underneath her with their movements before fixating on the her face, mouth hanging open in an O and her features locked into a look of rapture.

“You like having your ass fucked?” Ben asked even though the answer was plainly obvious.

“Uhh, yeahhh, fuck my ass,” Hilary pleaded.

“Gonna let me fuck it again some time?” Ben asked, his body screaming for release.

“You can fuck it whenever you want. Every day, every hour, just fuck my ass noowwww,” Hilary squealed, feeling her brain explode in a shower of ecstasy as she came from being fucked in the ass.

Ben was already on the verge of orgasm just from feeling Hilary’s super snug anal canal squeezing him in a death grip. Hearing her tell him he could fuck her ass any time he wanted, and then watch and feel her come from having his cock embedded in her shitter was way too much for him to handle.

“Gonna come, Hil,” Ben hissed through clenched teeth as tried to hold off just a second or two longer.

“I want to taste it,” Hilary said, looking over her shoulder at him. “I want to taste my ass on your cock and eat your fucking cum.”

How Ben managed to hear that, while still encased in the cocoon of Hilary’s bowels, without coming, he had no idea. Somehow though, he managed to yank his cock out of her asshole. Grabbing Hilary, he pulled her back towards him. As she turned to face him, he practically shoved his cock into her open mouth, desperate to unload the wad that was barely being held in check.

Feeling her warm inviting mouth close around the head of his cock, Ben stopped holding back. Eyes rolling back in his head he felt the jizz explode out of his cock. He’d held out long enough that a good amount of pressure had built up and the first spurt erupted with such force that Hilary barely managed to keep from reeling back in shock.

“That was amazing,” Ben groaned when his balls were dry.

“Pretty intense,” Hilary agreed, making sure to clean the rest of his cock with her tongue.

“If you keep that up, you know what’s going to happen,” Ben warned.

“As tempting as that is, Luca should be up soon and I need a shower,” Hilary said, sitting up. “Are you doing anything a week from Sunday?”

“Don’t think so, but it’s a school night so if you’re going to be out too late, I’d probably be better just crashing here after putting Luca to bed,” Ben said. It wasn’t entirely unusual for him to crash in the guest room if Hilary had a really late night.

“That’s fine, but I probably should be home by ten,” Hilary said, grinning knowingly. “You probably wouldn’t get home until twelve though.”

“I’ll clear my schedule then,” Ben said, grinning as Hilary slid off the bed.

“Good, because it’s going to take me that long to heal from this afternoon,” Hilary said, a little hitch in her step as she headed for the bathroom.

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