The Babysitter 2

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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.

Utica, NY (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.

Celebs of choice in this story are Hilary Duff and Reese Witherspoon. The codes are (MF, cons, oral, anal, cheat). 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 2

By voodoojoe

“Shit,” Reese Witherspoon grunted as she read the text.

“Bad news?” Hilary Duff asked.

“You could say that,” Reese sighed. “I’ve been planning a date night with Jim for weeks since we’ve been working so hard, and suddenly my nanny can’t work tomorrow. Normally I’d fire her, because if you can’t show up for work, then why bother, but I really like her.”

“I hear you,” Hilary said. “You find a good one, you don’t let them go.”

“You have a good nanny?” Reese asked, ears perking up. “Would you be willing to let me borrow her for an evening?”

“More just regular babysitter than nanny, and I don’t think Ben would like being called a ‘her’,” Hilary said, laughing.

“A male babysitter?” Reese asked, shocked. “Is he really good?”

“He’s the best,” Hilary said, nodding vigorously as she scrolled through the pictures on her phone. “Luca adores him. Here’s a picture of them reenacting Star Wars or something.”

“Wow, he’s cute, and young,” Reese said, looking at the picture of Luca dressed as Luke Skywalker and Ben as Han Solo. “How old is he?”

“Eighteen, but he’s a great kid,” Hilary said, smiling. “He actually lives next door so I actually knew him for a few years before. But he’s so good with Luca.”

“You and he haven’t, you know?” Reese asked, picking something up in Hilary’s praise of him. When Hilary blushed and lowered her eyes, Reese got her answer. “Oh my god, you have! Was it good? I never had much experience with guys that age because I met Ryan when I was twenty-one, but from what I did have, they, uh, didn’t know as much as they thought they did, if you know what I mean.”

“I think every woman knows what you mean,” Hilary said, giggling. “But Ben, while a bit raw, is very enthusiastic and a quick learner.”

“How many times have you guys done it?” Reese asked, realizing that it was obviously more than just once.

“A few times,” Hilary admitted with a sly grin. “Lets just say that occasionally I come home and he stays for an hour or two longer. Off the clock, of course. He might not have the staying power of an older guy, at least not at first, but he more than makes up for it in recovery time.”

“Too bad I’m married or I’d think about finding myself some young stud as well,” Reese said, feeling her body starting to respond to the idea of a guy that could go all night, or at least more than once a night. Her husband wasn’t bad in bed or anything, but it was usually once a week, twice if she was lucky, and as she hit her sexual peak it just never felt like enough.

“You can borrow Ben if you want, but I should warn you that he’s a bit of a, um, butt man,” Hilary said, hoping Reese understood.

“Ohh,” Reese said, feeling her body react even more. Not long after her first marriage ended she’d dated a guy that was really into asses for a bit. Eventually he’d talked her into anal and while it was one of those things that she’d liked enough to let him do it to her a few times it wasn’t something she went out of her way to do since. But as Hilary brought it up Reese’s brain refused to let it go.

“Here’s his number,” Hilary said, texting Reese Ben’s contact info.

“You sure you don’t mind?” Reese asked.

“As long as you don’t try to steal him,” Hilary said, nodding. “I’m willing to share him for an evening here or there, but I’d still like to be able to have him available for me once in a while.”

“I’m sure you won’t have to worry about that,” Reese said, smirking. “I’ll even make sure he can babysit once in a while as well.”

* * * * *

“Ohh ohhh ohhhhh,” Hilary moaned as Benjamin Jacobs drilled into her pussy from behind.

It had started innocently enough. She’d dropped by to tell him that she’d given his number to Reese, but he’d just gotten out of the shower and answered the door without a shirt and running a towel through his hair. Suddenly forgetting her train of thought, Hilary had let Ben grab her hand and pull her up the stairs to his bedroom.

Once on Ben’s bed, Hilary’s ability to think hadn’t improved much considering Ben had dropped to his knees, pushed her thighs apart and went to town on her pussy. After a pair of orgasms thanks to his tongue, Hilary finally pushed his head away so she could catch her breath.

As her head cleared a bit she managed to relay the information she’d gone over there to relay, including the tidbit about how Reese had reacted to him. The idea of Reese obviously sat well with him because he’d practically jumped on top of her, reaching between their bodies to aim his cock at her pussy before slamming forward and filling her up with this cock in one thrust.

He’d fucked her hard and fast, overcome a bit by both the idea of fucking Reese and the fact that he hadn’t plowed Hilary in a few days. Hilary had spurred him on with naughty talk about Reese’s MILF pussy. Somehow Ben had managed to hold off until Hilary came again before pulling out and covering her stomach with his seed.

After cleaning herself up Hilary had every intention of leaving. She’d gotten her rocks off and she really didn’t want to be in Ben’s bed when his parents got home. But when Ben reminded her that they only had a couple more weeks until he moved into a dorm, she’d started to weaken. Then when he’d assured her that his parents wouldn’t be home for hours, she’d let him position her on hands and knees so he could palm the cheeks of her ass while fucking her steadily from behind.

“Uhhh, come on, Ben, fuck my pussy,” Hilary hissed, feeling another orgasm building inside her.

While Ben would still be around -she wasn’t about to let him stop babysitting after all- he wasn’t going to be around nearly as much. And after a few months of having him right next door whenever she wanted to get laid she wasn’t nearly ready to have that change. Her pussy had gotten used to a regular dose of cock and wasn’t looking forward to cutting back.

“You want me to fuck you?” Ben snarled, moving his hands to her hips so he could get a better grip.

“Yeahhhh,” Hilary mewled as Ben ramped up the speed and power in his thrusts.

The room was filled with the sounds of sex. Bodies slapping together as his pelvis crashed into the cheeks of her ass, moans from Hilary as his fat cock stretched her pussy so wonderfully, grunts of exertion from Ben as he drove into her waiting snatch.

“Harder,” Hilary pleaded, then gasped as he gave her what she wanted.

As Ben pushed himself towards his breaking point fucking her as hard and fast as he could, Hilary let her head loll forward. Gripping his sheets in her hands she pushed back to meet his thrusts. Feeling sweat drip off her forehead, Hilary closed her eyes as she sought to reach her climax before Ben’s energy gave out.

“So close,” Hilary moaned as she hovered on the precipice.

Grinning as he moved one hand from her hip, Ben slipped the hand over her butt. Dragging his thumb through the crack of her ass, he stopped when it was just above the tight little pucker of her asshole. Striking before she realized what he had in mind, Ben pressed the tip of thumb against her anus and held it steady as she pushed back to meet his thrust.

“Oh gawwwwdddd,” Hilary squealed as her ass was penetrated without warning.

Already right on the edge, the sudden anal play was more than enough to push Hilary over the edge. Quaking in pleasure, her pussy clamped down on Ben’s cock. Unable to take any more, Ben tried to pull out to come on her ass.

“Noooo,” Hilary whined as she was suddenly left empty. “Come inside me.”

Barely registering her words, Ben nevertheless complied. Driving forward, he plunged back into her pussy. Shoving every inch of his cock into her sheath, Ben growled as he felt the cum rising up the shaft of his cock. The growl got louder as it exploded out of him, splattering against the walls of Hilary’s pussy.

Finally empty, Ben took another moment to feel the velvety softness of her pussy wrapped around his cock. Slowly sliding out of her, he let Hilary collapse onto his bed, their combined juices leaking out of her.

“Mmm,” Hilary sighed as he leaned forward, pressing his chest against her back as he kissed her.

“Want me to come over tomorrow night?” Ben asked, grinding his slowly deflating cock against her ass.

“What about Reese?” Hilary asked, sliding out from underneath him.

“If she calls, then I guess babysit,” Ben said, laying on his back and propping himself up on his elbows to watch her get dressed. “But even if she does, I could come by after.”

“I don’t know, it could be awful late by then,” Hilary said, giggling as she thought of Reese seducing Ben. She would’ve thought she’d be jealous at the idea of Ben fucking another woman after all the time they’d spent together, yet she actually found it hot. If he actually did it she knew she might feel different, but while it was still just theory it was incredibly hot to think of him making Reese scream out in ecstasy. “I guess if you find yourself with nothing to do about eleven or twelve, I might still be up if you wanted to drop by.”

As he watched Hilary put her bra on, Ben felt a little stirring in his loins. Before he could grab her and pull her back into bed though, his phone started ringing. Grumbling at his plans being balked, he rolled over to reach for his phone.

“This is Ben,” he answered, motioning with his hand for Hilary to turn around as she stepped into her pants and got a massive eye roll for his trouble.

“Uh, yeah, Hilary told me I should call you,” Reese said on the other end.

“Ah, you must be Reese,” Ben said, watching as Hilary buttoned her pants and bent over to pick up her shirt. “She said you might call.”

“Yeah, my nanny is unavailable tomorrow night and she recommended you,” Reese answered.

“I was going to spend some time with a friend tomorrow night, but I can put that off,” Ben said. “What time would you need me?”

“Say six?” Reese asked.

“Sounds good to me,” Ben said, frowning as Hilary stood in front of him fully dressed. “Text me your address and any special instructions and I’ll be there.”

“Awesome, you’re a life saver,” Reese sighed in relief.

“I think I need to thank you for getting me the job,” Ben said, tossing the phone onto the bed.

“Oh no, I need to get home,” Hilary protested rather halfheartedly as Ben reached for her.

“We’ve still got a few hours until my parents get home,” Ben said, grinning as Hilary didn’t even put up a cursory fight.

“You’re going to kill me one of these days,” Hilary sighed as Ben started removing her clothes again.

* * * * *

“You have my number,” Reese said after giving Ben a tour of the house and introducing him to her son, Tennessee. “Jim’s number and the number to the restaurant are on the table in case you have any questions. Bedtime is normally eight, but he likes to argue about it, so give him a little extra time if you want.”

“Phone numbers, bedtime, check,” Ben said, assuring her he had it down.

“Help yourself to the fridge, though I’d rather you skipped the wine, for obvious reasons,” Reese said, shrugging her shoulders.

“Underage and babysitting generally don’t mix well with alcohol,” Ben said, nodding.

“We should be home by eleven, midnight at the latest,” Reese said. “I’m sure you can figure out how to work the tv better than I do, so order a movie, use the wi-fi, whatever. Make yourself at home.”

“Well, have fun,” Ben said. “If you’re anything like Hilary, I’m sure you’ll want to check in every five minutes, so I promise not to get mad when you do.”

“Not every five minutes,” Reese said, smirking. “Maybe ten.”

* * * * *

Hearing the front door open, Ben was on his feet. He’d heard the key in the lock, so he was sure it was someone that belonged there, but he didn’t want to take it for granted. Coming around the corner into the hallway, he was greeted by an angry looking Reese Witherspoon.

“Home already?” Ben asked, sneaking a look at her ass in the tight red strapless dress she was wearing.

“That’s what happens when your husband decides he’d rather work than have a nice evening with his wife,” Reese said, kicking off her heels. With her older kids, Ava and Deacon, either with their dad or spending the night with friends, Reese had really been hoping a nice evening out would have led to a nice night in that was no longer going to happen. “Was he good?”

“He was great,” Ben answered. “I put him to bed and just checked on him a few minutes ago to make sure he was asleep.”

“Good,” Reese said, softening up a bit.

“So, feel like talking about it? I’ve been known to be a good listener,” Ben offered as she made her way to the kitchen.

“He had a deal that was supposed to be a done deal but I guess it’s falling apart and it needs his attention more than me,” Reese sighed, pouring herself a glass of wine. “So now I’m here with you while he’s at the office working phones trying to put it back together.”

“I can get out of here if you want,” Ben said, turning and pointing toward the door of the kitchen.

“Why? As far as I’m concerned you’re still on the clock,” Reese said, grinning.

Raising the glass to her mouth, Reese gave Ben an appraising look. He wasn’t huge, but considering how short she was, he was probably a solid foot taller than she was. And while he wasn’t super muscular, she could see enough definition in his arms to tell that he was in pretty good shape. Plus, he was really cute.

“So you’re going to keep paying me even though you’re right here?” Ben asked, not sure whether he should argue or not.

“I’m going to pay you until midnight either way, so you don’t have to stay,” Reese said, remembering what Hilary had said about him being really good in bed. That in turn reminded her that she should’ve been getting laid tonight.

“Any time you need a sitter, I’m your man,” Ben said, laughing as he followed Reese to where she’d set down her purse.

“I’ll have to keep that in mind,” Reese said as she counted out some cash for him. “This should cover it.”

“Actually, this is probably a little much,” Ben said, trying to give her back her change.

“Keep it,” Reese insisted. “Consider it a tip or a short notice bonus, or however you want to think of it.”

“Thanks,” Ben said, tucking the money in his pocket.

“If you wanted to stay though, I wouldn’t mind,” Reese said, giving him her best come hither look, which really wasn’t very good since she hadn’t practiced it in years.

It worked though because as she moved into the tv room, Ben was right behind her. Feeling butterflies in her stomach over what she was thinking, Reese turned to face him. Taking a deep breath, she reached up and cupped the back of his neck. Pulling his head down, she stretched to kiss him.

“That was unexpected,” Ben said, his pants suddenly feeling tight.

Not responding, at least not verbally, Reese kissed him again, this time letting her tongue press against his lips. When he opened his mouth to let her tongue in, her other hand drifted down over his stomach until it reached his waist.

Breaking the kiss, Reese gave Ben a look pure, unadulterated lust. Undoing his belt, her fingers popped the button on his pants. Pulling down the zipper, Reese pushed his pants over his hips and down his legs. Pulling back slightly, she hooked her thumbs in his boxers and yanked them down, getting her first glance at his cock.

“Damn,” Reese gasped, eyes widening a bit in surprise. It wasn’t particularly long, but it was so thick.

Licking her lips, Reese put a hand on Ben’s chest and lightly pushed until the got hint. As he sat down on the couch, she dropped to her knees in front of him. Reaching out, she grabbed hold of his cock, her fingers not even touching as they wrapped around his girth.

Giving his cock a couple strokes, Reese leaned in and ran her tongue along the underside of his shaft. When Ben groaned, she smiled and licked along the crown before opening her mouth. Wrapping her lips around the head of his cock she gave it a suck.

“Nnngghhhh,” Ben grunted as she swirled her tongue around the tip of his dick.

Reese didn’t always like giving head. It took her a long time to get to where she enjoyed it. It had always seemed to be expected, as if she absolutely had to suck a dick if it was presented to her. It wasn’t until after her first divorce, when she was older and a bit more experienced, that she’d realized there was real value to being in control and having her partner at her whim.

She didn’t give head very often though. Her and her husband were both way too busy for even a consistent sex life and what little time they managed to carve out wasn’t about to be spent that way. But after seeing his cock she just had to taste it, and if she was going to do something so naughty as to seduce an eighteen year-old guy, then she might as well do it right.

With just the head in her mouth, Reese tilted her head and made eye contact with Ben. Smiling around at him his cock, she slowly worked more of him into her mouth. Her lips stretched to accommodate him.

About halfway down his cock Reese stopped and took a deep breath. Applying suction she started working her way back to the top. Reaching the head, she broke the suction and let her tongue swirl around the crown while she breathed through her nose.

“Uhhhh,” Ben groaned as she bobbed up and down on his cock. Her hand stroked the lower part of his shaft as she slowly worked her mouth up and down the upper half.

Reese felt her pussy start to drool as she got more and more into the act. Ben’s cock was so thick that she couldn’t go very fast with her head bobbing, but neither of them really minded. She was enjoying feeling her lips stretched around his cock and, as a guy, Ben was just happy to have his dick sucked.

“Such a hot little mouth,” Ben hissed, putting a hand on the back of her head.

“Mmhmm,” Reese moaned in agreement as she worked on his cock.

“If you keep it up, I’m gonna come,” Ben warned as Reese increased her suction.

Normally a warning like that would’ve cause Reese to slow down, or even pull off altogether. At the moment however, it just made Reese suck even harder. She was lost enough in her lust that she really wanted him to come. If Hilary’s scouting report was accurate, Ben wouldn’t have a problem getting up again, so Reese didn’t see much of a downside to letting him unload one before the main event.

“Fuck, gonna come,” Ben grunted, his grip on the back of her head tightening as he felt the cum rising.

Still wearing her dress, Reese couldn’t let him pull out and come on her tits or face. So with the only option being her mouth, she pulled back until just the head of his cock was in her mouth. Sucking on the head, she stroked the shaft, jerking him off as he grunted and humped his hips.

“Ahhhh,” Ben groaned, leaning his head back as the floodgates opened.

The first blast took Reese by surprise a bit with the force behind it, but once she recovered it wasn’t too hard to keep up with him. As Ben painted her tonsils with his gravy, she moaned and kept sucking, even after the spasms had stopped ejecting cum. Finally letting his thick cock slip from her mouth, Reese tilted her head back and let the oyster slide down her throat.

“That was impressive,” Ben said as Reese continued slowly stroking his cock.

“And you have a lot to compare it to, huh?” Reese asked, smirking.

“Not nearly as much as I’d like, but a few,” Ben said, grinning.

“In that case, I’ll take it as a compliment,” Reese said, shocked that she was already feeling him start to respond to her handjob. “The power of youth.”

Once she’d stroked him back to full strength, Reese stood up. Grabbing the hem of her dress, she shimmied it up her thighs until it was around her waist. Hooking her fingers in the waist of her thong, she yanked it down, giving Ben a nice flash of her trimmed patch of pubic hair before she lifted one leg to step out of her underwear.

Kicking off her panties, Reese rested a hand on Ben’s chest. Putting a knee on the couch on either side of him, she straddled his lap. Reaching between them, she grabbed hold of his cock. Lifting up, she made eye contact with him as she aimed his cock at her opening.

“Ohhhhh,” Reese moaned as she eased herself down onto his cock, feeling her pussy stretch around his cock.

When Reese reached bottom, she paused to let herself get used to his size. Taking advantage of the pause, Ben wrapped his arms around her. Finding the zipper on the back of her dress, he pulled it down. As she started the lift up, he tugged her dress down to reveal the strapless bra she had on underneath.

With her dress bunched around her midsection, Reese eased back down, feeling him fill her up again. Moaning, Reese started to slowly rise and fall on top of him. His cock felt so big inside her and each time she dropped down onto it she felt so incredibly full.

Reaching around Reese’s body, Ben found the clasp of her bra. After a moment of fumbling with it, she was moving after all, he finally got it unhooked. Pulling the bra away, Ben licked his lips at the sight of her tits.

Leaning his head forward, Ben parted his lips. Capturing one of her nipples in his mouth, he covered his teeth with his lips and gently massaged the soft bud. When Reese moaned and pushed her chest out, he swirled his tongue around the nipple.

“Ohhhh,” Reese moaned quietly as he suckled at her tit.

Reese felt guilty for doing what she was doing, but the lust had taken over. With each thrust she made she lost herself even further to the pleasure and desire she was feeling. It had been so long since she’d experienced a new man and the knowledge that she was bouncing up and down on a taboo cock only made her desire it more.

“Such a big cock,” Reese hissed into Ben’s ear.

Faced with a choice between responding or continuing to suck on the nipple, Ben chose to mumble something that sounded like a thank you while rolling the little pink nub between his lips. Softly biting down on it, he tugged on it until it popped free of his mouth.

Shifting focus to her other breast, Ben quickly captured its nipple between his lips. Sucking on the nipple he brought one hand up to her chest to palm the recently vacated tit. With one hand doing nothing, Ben couldn’t help himself as he reached around to grab her ass.

Feeling his hand on her ass reminded her of Hilary’s warning that he was an ass man. As he squeezed her butt cheek, Reese moaned and quickened her pace. Clutching his head to her chest Reese felt the pleasure rise inside her much faster than she would’ve thought possible.

Making short, quick bounces on Ben’s cock, Reese’s breathing became ragged. Biting her lip to stifle her moans so she didn’t wake up her son, Reese felt her legs start to weaken. Groaning, she tried to get to her orgasm before her legs gave out, but it just wasn’t working.

Sensing her predicament, Ben abandoned her chest. Moving his other hand to her ass, he squeezed the cheeks as he lifted his hips and drove into Reese’s pussy. Before the moan was out of her mouth he was already plunging into her again.

Fucking her hard and fast Ben used his grip on her ass to hold her mostly steady as he drilled into her. He could feel her body responding to the treatment as she buried her face against his neck to muffle the sounds of impending climax.

Each thrust Ben made into her pushed Reese closer and closer to her climax. Yet as she reached the precipice she seemed to stall and hover with it so close, yet just out of reach. And then suddenly, she was there.

“AHHHHHH,” Reese screamed into Ben’s neck and collarbone as she came.

Holding Reese’s quaking body tight against his own, Ben gritted his teeth and managed to ride out the waves. He was very thankful that he’d already come once or he never would’ve made it through without busting his nut.

“Mmm,” Reese moaned as she finally settled down on top of him. Straightening up, she started to lift off until she got halfway up and realized he was still rock hard. “You didn’t?”

“It was close,” Ben admitted, grinning.

With that, Reese started realizing that maybe Hilary wasn’t overselling him after all. Sure he was cute, and he had a really nice cock, but even more important than those things was stamina. And if Ben could keep from blowing his wad like that, then maybe he really was as good as Hilary said. Hell, even if he actually had come and managed to stay hard, she was still impressed.

When Reese dropped back down onto his cock, it sent a pretty clear message to Ben about whether they were done yet. Smirking, he moved one hand up to the middle of her back while the other stayed on her ass. Lifting up, he turned and planted her on her back on the couch.

“Noooo,” Reese groaned as Ben suddenly pulled out of her.

“Don’t worry, I’m not done yet,” Ben said, grabbing the dress that was still bunched up around her midsection. As she lifted her butt off the couch, he pulled the dress down her legs and let it drop to the ground.

Standing up, Ben took a moment to take in the sight of her naked body. It wasn’t as tight as those of girls his age, but it still looked damn good to him. After all, he was an eighteen year-old guy and any naked woman was something to be worshiped. But Reese really did look gorgeous as she laid there waiting for him to fuck her some more.

“Like what you see?” Reese asked, giving him a slightly nervous smile.

“Oh yeah,” Ben said, nodding as he moved onto the couch.

As Reese spread her legs, Ben moved in between them. Grasping the base of his cock he guided it towards her opening. Pushing forward, he watched her pussy open up to take him back inside, wrapping around him like a glove.

“Ohhh,” Reese moaned, her hands going to her chest to cup her tits and tweak her nipples.

Reaching bottom, Ben put his hands on the couch on either side of her. Barely pausing to let her get used to the size of his cock, Ben pulled half of his cock before driving back into her. When Reese bit her lip to stifle her moan, he withdrew again.

“Uhhh, harder. Fuck me harder,” Reese urged.

Taking her at her word, Ben gave Reese what she wanted. Bringing his knees underneath him, he put as much power behind his thrusts as possible. Each push caused her tits to jiggle with the force and that only spurred on Ben to increase his pace.

“Ohhh, that’s it, Ben. Don’t even worry about me, just fuck me until you come,” Reese hissed.

Part of her request was that she wanted to see what he was capable, but mostly it was out of not wanting to get caught. Her husband often slept in his office when he worked really late like tonight, but there was still a chance he could come home at any time. Or her son could wake up and come looking for her. It was just better to let him rut away until he was done and end it quickly than try to drag it out in hopes of getting another orgasm that might not even happen anyway.

That didn’t mean Reese wasn’t having a good time as Ben drilled away at her pussy. The energy and vigor with which Ben was using to fuck her was exhilarating and she could definitely see what Hilary saw in him.

“Fuck me,” Reese grunted, lifting her hips to meet his thrusts. “I want you come on my tits. You want to come on my tits, don’t you?”

“Oh yeah,” Ben snarled, somehow ramping up his intensity even further as he thought about covering her tits with his goo.

“Shit,” Reese groaned as Ben somehow hit another level. She hadn’t gotten fucked with this much energy in years and despite herself she started to feel the tiny germ of an orgasm take root inside her.

As Ben kept going after she’d expected him to succumb, Reese felt the tiny seed of pleasure start to flourish. It grew, slowly at first, but quicker as she got more and more into what he was doing to her. Ben, however, was still just an eighteen year-old guy and couldn’t be expected to hold up such a punishing pace forever.

“Ahhh,” Ben muttered, clenching his teeth as he suddenly yanked his cock out of Reese’s pussy.

Moving up the sofa to straddle Reese’s midsection, Ben gave his cock a couple quick tugs. Throwing his head back he felt the cum erupt from his cock. It arced through the air, striking the underside of one of Reese’s breasts before the second shot came in a little higher and striped her tit across her areola.

Feeling Ben’s warm seed splashing against her skin, Reese moaned and instinctively pushed her chest up. She’d been left much closer to orgasm than she would’ve thought possible, but she fought the urge to try to get there with her fingers. Instead, she brought her hands to her chest.

“Mmm,” Reese moaned, making eye contact with him as she rubbed his jizz into the skin of her breasts.

“Damn,” Ben groaned. No girl had ever done that for him and it turned him on beyond belief.

“As much as I’d like to put that to more good use, you should probably go home,” Reese sighed, noticing that his cock was showing signs of life again. The power of being eighteen.

“Uhh, yeah, okay,” Ben said, averting his eyes and climbing off of her.

“I had fun tonight,” Reese said, sitting up. “Thanks for, you know, everything.”

“If you ever need a babysitter again, I would be more than happy to do it,” Ben said, smiling.

“I’ll keep your number handy,” Reese said, torn between wanting to call him again and feeling guilty for wanting to call him again.

* * * * *

“She begged me to come on her tits, so when I was ready, I pulled out and let her have it,” Ben said, recounting his evening to Hilary Duff as they sat in Hilary’s kitchen.

“Wow,” Hilary said, picturing Ben and Reese together.

“You don’t mind, do you?” Ben asked.

“No way, that was hot,” Hilary insisted. “So, when is Reese going to call again?”

“I don’t know if she will,” Ben said, shrugging his shoulders. “She said she’d keep my number handy if she ever needed a babysitter again, but I think she was already feeling guilty, so I don’t think she will.”

“Oh well, I guess that means you’ll have more time for Luca,” Hilary said with a half smirk. “And me.”

“You know, it’s not quite midnight,” Ben said, grinning as he gave her a kiss.

“I might think it’s hot, but I’m not going to let you jump right from her bed to mine,” Hilary said, putting a hand on his.

“It was worth a shot,” Ben said, grinning.

“Luca’s going to be with his dad this weekend if you wanted to drop by,” Hilary suggested.

“I think I’m going to go home and take a shower,” Ben said, standing up. “Shoot me a text on Saturday when you want me to come over.”

* * * * *

“This is Ben,” Ben said, answering his phone.

“Uh, this is Reese,” Reese said, sounding nervous on the other end.

“Oh, hey,” Ben said. “What can I do for you?”

“Well, I was wondering if we could talk,” Reese said.

“Yeah, sure, did you want to somewhere or something? There’s a coffee shop just down the street,” Ben suggested, his mind whirring in opposite directions about what she might want to talk about.

“No,” Reese said quickly. “I mean, I was hoping we could do it somewhere private.”

“Want me to come over there?” Ben asked.

“Actually, I was wondering if I could come over there?” Reese countered.

“Sure, want me to text you the address?” Ben asked, trying to parse the conversation in his head.

“That’d be great,” Reese sighed. “I’ll be there in a bit.”

* * * * *

“Come in, come in,” Ben said, moving out of the way to let Reese enter the house.

“Thanks for meeting me,” Reese said as Ben led her into the living room. “I just wanted to talk about last night.”

“Let me guess, you don’t think we should do it again?” Ben asked as she took a seat on the couch. He figured it was either that or she wanted him to take her to his room and fuck her senseless, but this seemed more likely.

“What we did was a mistake,” Reese sighed. “I’m married and you’re a teenager.”

“I’m eighteen, if that helps,” Ben piped in.

“Maybe a little, but not enough,” Reese said, laughing slightly. “It doesn’t change the rest though.”

“Figured as much,” Ben said, shrugging his shoulders. “But if you ever need a babysitter again, I’d be happy to do it. He’s a great kid and we had fun.”

“Tell me about it,” Reese said, smiling. “All I heard this morning was Ben this, Ben that. You made quite the impression on him.”

“I also had a lot of fun after he went to bed,” Ben said, smirking.

“So did I, which is why it can’t happen again,” Reese sighed, feeling more than a little guilty for thinking about letting Ben take her upstairs and give her an encore. “You also can’t tell anyone.”

“Don’t worry, I won’t tell anyone,” Ben insisted, picking up something in her mannerisms. “Well, I told Hilary, but she won’t tell anyone.”

“Good,” Reese said, more than a little relieved that he at least seemed to be sincere in his agreement.

“Though if I remember right, I still owe you one,” Ben said, raising an eyebrow.

“Owe me one?” Reese asked, confused.

“You sucked my dick but I didn’t get to eat your pussy,” Ben clarified, moving in closer. “Tell me to stop and I will, but until you say the words, I’m going to keep going.”

With those words ringing in her ears, Ben slipped off the couch. Kneeling in front of Reese, he put his hands on her knees. Locking eyes with her he slowly slid his hands up her thighs, sliding underneath her skirt as he waited for her to tell him to stop. When he reached her crotch without so much as a peep, Ben knew she wouldn’t.

Reese had honestly come over with the intention of not letting last night repeat itself, but as Ben pulled her underwear down her legs she knew her resistance was hanging by a thread. She told herself that, as he said, he owed her some oral sex, but deep down she knew that if he knew what he was doing he’d definitely do more than eat her pussy before she left.

Starting slowly, Ben softly lapped at her pussy. Not wanting to push her, he settled in for a nice long session where he gradually worked her up to it. And just before he got her there he slid a finger into her pussy. The combination of his tongue on her clit and his finger working in and out of her pussy set her off.

But much to Reese’s surprise, Ben wasn’t satisfied with giving her one orgasm. After she came down from her peak he slowed back down, but as she started to respond to his ministrations again, he went after her again, building the intensity as he went until she exploded again, and then a third time not long after the second.

“Ohh, stop, stop, stop,” Reese groaned, finally unable to take any more.

Giving her clit one last flick with his tongue, Ben finally slid his finger out of her pussy. Disengaging from her pussy he pulled back to grin up at her. The look of dreamy detachment on her face as she looked back at him told him all he needed to know about his performance.

“So, does that make us even?” Ben asked, cocking an eyebrow.

“Not even close,” Reese sighed. “After that, I think I owe you now.”

“Do I get to pick how you repay me?” Ben asked, trying to decide whether he’d rather have her suck his dick or fuck her. He really wanted both, but he wasn’t going to push his luck. Actually, really pushing his luck would’ve been trying to fuck her ass, but he was sure that wasn’t happening.

“I don’t see why not,” Reese said, biting her lower lip as the idea of giving him a choice added a certain level of suspense.

“Then we should probably go upstairs,” Ben said, standing up.

“Okay,” Reese said, watching as he picked up her panties and handed them to her.

Extending his hand, Ben helped Reese up. Keeping hold of her hand, he led her up the stairs towards his bedroom. Closing the door behind him, he kicked off his shoes. Grabbing his shirt he pulled it off over his head before going for his pants.

“If you suck my dick and then I fuck you, does that mean I owe you again?” Ben asked, stepping out of his pants.

“Pretty sure, yeah,” Reese said, nodding her head.

“Works for me,” Ben said, pushing down his boxers.

Grinning, Reese dropped to her knees. Shuffling forward until she was right in front of him, she reached out and wrapped her hand around the base of his cock, her fingers not even touching as she gripped him. After giving his shaft a couple strokes she opened her mouth to take him inside.

After the performance Ben had given her downstairs, Reese was intent on showing her appreciation. She’d always been a bit more spirited in the bedroom after a guy ate her pussy, and as she worked her way up and down his cock, now was no different.

“Uhh, yeah,” Ben grunted as Reese sucked hard enough to cause his knees to go weak.

Stroking his shaft with one hand, Reese used the other to cup and fondle his balls. She could feel him turning to putty in her hands as she pulled back until only the head of his cock was in her mouth. Swirling her tongue around the head, she flicked the pee hole before working her way back down his cock.

“Get on the bed,” Ben grunted, realizing that if he let her keep going he wasn’t going to last much longer in her mouth.

“You sure?” Reese asked, still stroking his cock.

“I guess that depends on where you want me to come the first time,” Ben said, trying not to think about the handjob she was giving him.

“I bet you want to come on my face, don’t you?” Reese asked, letting her tongue dart out to flick at the crown of his cock.

“Jeez,” Ben grunted, nearly losing it as he pictured Reese’s face covered in his cum.

“Ooh, you do, don’t you?” Reese prodded, tilting his cock upwards so she could lick along the underside of his shaft. “You want to coat my face in your filthy cum?”

“Yeah,” Ben admitted, feeling his cum rising at the thought.

While talking dirty to him Reese had used the hand that wasn’t stroking his cock to unbutton her blouse. When the last button came free, she pulled it open. Barely missing a beat in her handjob, she managed to push the blouse off her shoulders and hoped it would be enough to avoid getting any of his cum on it.

Normally Reese wasn’t a big fan of facials. They were messy and she hated when it got in her eyes, but seeing how Ben reacted to the idea had made her determined to do it. Besides, the idea of another man’s jizz dripping off her chin kinda turned her on, made her feel dirty.

Feeling his cock pulse in her hand, Reese gave it a couple more quick strokes. Pointing it at her face, Reese watched as the first white ribbon of cum leaped out her. Just before clamping her eyes shut she felt it strike her upper lip. With the dam broken up, her face was battered by spurts of hot gravy, his thrusting hips causing the angle to change slightly with each eruption until she had streaks of white coating her face from nose to chin.

“Shit,” Ben grunted, his hips still humping against her hand even as his balls ran dry.

“Have fun?” Reese asked, giggling slightly as she opened her eyes to look at him.

“Oh yeah,” Ben sighed as she finally let go of his cock. Seeing the mess dripping off her face and onto her upper chest, he grabbed a t-shirt and held it out for her.

“Then I guess you owe me again,” Reese said, taking the shirt and using it to wipe her face.

“Get on the bed and I’ll do whatever you want,” Ben said, licking his lips and tasting remnants of her juices.

“Ben?” Reese asked, sitting on the edge of the bed.

“Yeah?” Ben asked, watching as she slid back towards the middle of the bed.

“Hilary said you were an ass man?” Reese asked, feeling the butterflies in her stomach as she pushed down her skirt.

“She did?” Ben asked, wondering where it was headed.

Taking a deep breath, Reese rolled over onto her stomach. Ben’s cock lurched as he caught sight of Reese’s ass. He still didn’t want to get his hopes up though, even when she pushed herself up onto hands and knees. When she pushed her ass back in his direction and gave it a little shake, he practically swooned and took the invitation.

Hedging his bets a bit, he grabbed one of Reese’s butt cheeks in each hand. It certainly wasn’t the tight, skinny ass like most girls his age, but that extra fleshiness made it even better. There was an ampleness to it that he loved feeling in his hands, yet it was still very firm and only had a little give as he pressed his fingers into the surface of the skin.

When Reese didn’t object, he leaned in. Opening he mouth wide he pressed his teeth against the surface of one butt cheek. Not so much biting as just slowly closing his mouth, he dragged his teeth along her skin until it was almost closed and then let his lips replace them to turn it into a kiss.

“Mmm,” Reese sighed, looking back over her shoulder as he literally kissed her ass.

After repeating the process on the other cheek, Ben used his hands to pull her cheeks apart. He saw the lips of her pussy peeking out from between her legs but his eyes were drawn to the tight pucker of her asshole, just begging to be licked.

“Oooh,” Reese moaned, hitching her ass up higher as Ben ran his tongue along the rim of her anus.

Gripping and squeezing Reese’s cheeks, Ben was in heaven. He had a fantastic ass to play with and a tight little asshole to munch on. If she’d told him to do stay like that for four hours, the only problem he would’ve had was that it wasn’t longer.

“Ohhh, you’re good at that,” Reese hissed as Ben alternated between light strokes along the surface of her asshole and rougher licks that probed at her hole.

While anal was normally something Reese could take or leave, she loved having her ass licked. As far as she was concerned, it was totally worth the pain and mess and everything else that came with having her ass fucked if it meant getting her ass eaten in preparation. And as Ben’s tongue slathered attention on her tender butthole, Reese started to feel a craving for something else in her ass that she hadn’t felt in years.

“Fuck my ass,” Reese grunted as Ben’s tongue poked at the center of her starfish until she felt her sphincter start to yield to it. “I want you to fuck my ass.”

Hearing the magic words, Ben didn’t need to be told twice. Pulling away from Reese’s ass, he ignored his instinct to get back in there when she groaned at being left alone, but it was a necessary evil. Giving her ass one last squeeze, he slid off the bed so he could grab his bottle of lube.

For his birthday Hilary had given him a couple presents. The first was the bottle of lubricant he’d just fished out. The second was a little slumber party and the opportunity to use the lube, repeatedly. Within minutes of Luca being put to bed he was balls deep in Hilary’s ass, then again after she’d used her mouth to clean him up and suck him back to hardness. For the third time he’d woken up in the middle of the night to find her sucking his cock before climbing on top of him and bouncing away with him buried in her ass. Then finally he’d butt fucked her in the shower the next morning before going home.

Squirting a healthy dollop of lube on his hand Ben rubbed his fingers into it to warm it up a bit as well as get some on his fingers. Dragging his slick fingers through Reese’s crack, he found her asshole and rubbed a moment before pushing.

“Uhhh,” Reese grunted as she felt his finger slide into her ass.

Feeling her snug asshole grip his finger had Ben rock hard. Well, he’d been rock hard pretty much the moment she shoved her ass in the air and invited him to feast, but as he prepped her ass to accept his cock he achieved iron bar status.

“Do it,” Reese hissed as Ben started pumping two fingers into her ass.

Grinning at her eagerness, Ben straightened up. With some excess lube still in the palm of his hand, he wrapped it around his cock and smeared it along the shaft. Just to make sure he added a bit more and stroked his cock a couple times to get it nice and coated.

Stepping up behind Reese, Ben guided his cock towards the shiny crinkle of her anus. Pressing the tip against her asshole, he felt her tense up momentarily before willing herself to relax. Feeling her asshole start to give way, he pushed forward, the head popping past the muscle of her sphincter and into her ass.

“Ohhh fuuuckkkk,” Reese gasped, her eyes going wide as saucers as her asshole was penetrated. When she’d told him to fuck her ass, she hadn’t bothered to think about how big he was. He was so much bigger than anything else she’d had back there, yet as he pushed himself in deeper she found herself moaning and pushing back against him.

“You must really like getting fucked in the ass,” Ben observed. Between her eagerness and the moans as he slowly worked his way into her, it was clear she was enjoying it.

“Not normally,” Reese confessed. “But right now, I love it.”

“Just so you know, any time you want to get ass fucked, I’m your man,” Ben said, gripping her hips and lunging forward, burying the last two inches up her ass.

“I’ll, ohhh, keep that in mind,” Reese said, her head spinning as she felt like she was going to rip in half from the large cock throbbing inside her rectum.

As Ben slowly extracted a few inches of his cock, Reese felt a weird thrill shoot through her. When he reversed course and pushed back into her, she felt the nerve endings in and around her anus come to life in ways her ex had never managed. She wasn’t sure if it was because she was older and she reacted to things differently, or maybe it was his thicker cock, or just that she was so turned on, but anal was never like this before.

“Ohhh, fuck my ass, Ben,” Reese hissed as he drove into her ass.

“Faster? Harder? Just fuck it?” Ben asked, looking for some kind of direction as he slid about half of his cock out of her gripping asshole.

“Harder,” Reese groaned, pushing back to meet his thrust as he plunged into her tight asshole hard enough to make the room echo with the sound of his pelvis slamming into her fleshy butt cheeks.

“Like this? Or do you want to fuck your ass even harder?” Ben asked, watching the globes of her ass ripple deliciously with each thrust he made into her back door.

“A little, uhh, harder,” Reese grunted, shocked at how much she was enjoying being sodomized.

“You have an amazing ass,” Ben said, increasing the power in his thrusts just a bit, like she wanted.

“Then fuck it, fuck it so good,” Reese demanded, slipping a hand underneath her.

As Ben slammed into her ass, Reese’s finger found her clit and it was like setting off a bomb inside her. The burst of pleasure was incredible and instant. Within seconds the combination of the cock stuffing her ass and the finger on her clit had her on the verge of coming already.

“Ohh, fuck my ass, fuuuuckkkkk iiiitttttt,” Reese screeched, her body exploding in orgasm.

Feeling her seize up in climax already, Ben was shocked, but that didn’t stop him. If anything, it spurred him on since he hadn’t had enough to build up his own despite the extremely tight confines of her asshole. He slowed down considerably given the way her asshole had clenched up around him, but he kept driving into her ass, making her moan with each thrust.

When Reese’s orgasm finally ran its course, Ben finally stopped. Moving his hands to her ass, he gripped her butt cheeks and pulled them apart as he eased his cock out of her ass. He groaned at the sight of her asshole gaping wide open as he popped free.

“Still hard?” Reese asked, turning around to see his cock red and throbbing as it jutted out from his body.

“I didn’t come,” Ben said, shrugging his shoulders.

“Then why did you stop?” Reese asked, shocked.

“I don’t know,” Ben answered honestly. Actually, while she definitely enjoyed it while it was happening, he wasn’t sure whether she would’ve wanted him to keep going or not.

“Well, we can’t leave you like that,” Reese said, staring at his cock as she finally shed her blouse. It had been hanging open since she’d decided she wanted a facial but then had gotten caught up in her desire for anal play and forgotten it.

“Where do you want me to stick it?” Ben asked, staring at her tits as she unhooked her bra and pulled it down her arms.

“Come here,” Reese said, laying down on her back on the bed.

Moving in between her spread legs, Ben let her grab hold of his cock. He half expected her to guide him into her pussy but instead she continued to push him lower until the head of his cock was pressed against her asshole. When she gave him a little tug, he pushed forward, feeling his cock slowly engulfed in the tight warmth of her ass.

“Ohhh,” Reese moaned as he surged forward until he was balls deep in her asshole.

As much as she’d enjoyed feeling him fuck her ass from behind, she almost liked this position better. She didn’t expend any energy holding herself up and she could see him as he gripped her thighs to start moving in and out of her ass. It also gave her perfect access to her pussy to diddle herself while he butt fucked her.

“Such a butt slut,” Ben said, watching as her fingers resumed stroking her clit.

“Ahhh, fuck my ass harder,” Reese hissed as Ben set a moderate pace.

Using his grip on her thighs he did just what she wanted. Holding her in place he drove forward with as much power as he dared in such a tight hole. The moment his pelvis slammed into her, he immediately pulled back until half of his cock was outside her asshole.

“Harder,” Reese grunted, lifting her hips to meet his thrusts as his cock bored into her asshole.

Leaning forward, Ben placed his hands on her chest. Cupping a tit in each hand, he shortened his strokes down to just a couple inches as he fucked her hard and fast. Her hand moved at an equally fast pace on her clit as they both frantically sought release.

“That’s it, take my cock up your fucking Oscar-winning ass,” Ben snarled, squeezing her tits as he drilled her ass.

“Uhh, yeah, fuck my, ohhh, ass,” Reese pleaded, reaching between their bodies with her other hand to feel his cock plunging into her asshole.

“I’ll fuck it so hard you have trouble walking later,” Ben promised, feeling his orgasm start to approach.

Lost to his lust and need, Ben pounded in Reese with abandon. Luckily Reese was just as lost and even though she was sure she was going to sore when the endorphins wore off she loved every second of it. It was worth it to feel him fucking the shit out of her, in command even as he went out of his way to make sure it was good for her as well.

“Gonna come,” Ben warned, humping away at Reese’s ass even as he felt the cum churning inside him, crying out to be unleashed.

“Uhh, come in me,” Reese hissed, wanting to feel his cum splashing around in her bowels. “Come in my ass.”

Nodding his head, Ben continued to pound mercilessly into Reese’s asshole. As Reese moved her fingers on her clit at a blinding speed,  Ben felt his toes start to curl with the first blush of his climax. Gritting his teeth he made a couple more thrusts before it was just too much. Driving deep into Reese’s asshole, he let out low growl as he let loose.

“Ohhh yessss, AHHHH,” Reese screamed, the sensation of feeling him erupt inside her setting her off as well.

Instinctively making short pushes against Reese, as if trying to get even deeper inside her, Ben poured his essence into the snug confines of her asshole. With each spurt, Reese’s anus and rectum squeezed him, milking him for all he was worth until he was finally empty.

“Shit,” Ben grunted, collapsing on top of her, his cock still in her asshole as its tight grip kept him from going soft quite yet.

“Damn,” Reese sighed, her thighs lolling apart as she luxuriated in the warmth of his body covering her.

Eventually Ben’s cock softened enough to slip from her ass. Lifting up off of her, he grabbed one of his dirty shirts and handed it to her so she could catch his cum as it leaked out of her. Sitting up, Reese sighed as she realized she must have looked a mess.

“I hate to run off like this, but I really need to go,” Reese said, grabbing for her clothes. “I was going to go to the gym, but I think I just got a much better workout.”

“Any time you need another workout like that, I’m here for you,” Ben offered as she pulled on her blouse.

“You know what, I think I will go to the gym,” Reese said, stepping into her skirt. There was no way she was going to work out after that, but it would give her an excuse for taking a shower in the middle of the day.

“Or you could stay here and see if I have another one in me,” Ben suggested, grinning.

“Tempting, but I think I might need another workout in a couple days,” Reese said, acknowledging that she definitely wasn’t going to stay away like she’d initially intended. It was wrong and she knew she shouldn’t, but a guy that seemed to like eating pussy and could fuck like a dickens, all with the energy and stamina of a teenager was just too much to pass up.

“Give me a call,” Ben said, still completely naked as Reese nodded and slipped out of the room.

Ben wasn’t alone long though. Before the front door even slammed shut with Reese’s departure, his bedroom door opened with the beaming face of Hilary standing in the doorway.

“I saw Reese’s car and came over to say hi, but then no one answered the door and I let myself in,” Hilary explained as she crossed the room to stand in front of Ben. “God, it was so hot listening to you and her like that.”

“I thought you weren’t going to let me jump from her bed to yours?” Ben asked as Hilary dropped to her knees in front of him.

“I’m not going to fuck you,” Hilary said, her hand wrapping around the base of his rapidly inflating cock. “But I am going to suck your dick and taste Reese’s ass on it.”

With that, Hilary did just that. Taking the head into her mouth she moaned as she tasted the remains of Reese’s ass on it. The knowledge that it was Reese she was tasting drove Hilary nuts as she worked more of Ben’s cock into her mouth. She loved tasting herself on Ben’s cock, or his fingers, or her toys, after they’d come out of her ass, but this was the first time she’d tasted another woman’s ass.

“If you keep that up, I’m going to want to find somewhere else to stick my cock,” Ben grunted as Hilary bobbed her head up and down on a little more than half of his cock. “Reese made me come twice, but I’ve still got one left if you want it.”

Ignoring him, Hilary used her right hand to stroke the bottom half of the shaft while her mouth worked on the upper half. She’d spent enough time with his cock in her mouth to have some idea of what he could handle. And after a couple orgasms, he wasn’t going to come any time soon, so she didn’t worry too much about that.

“At least swing your body around so I eat your pussy,” Ben pleaded, knowing that if he got her shorts off he’d find little resistance when he tried to fuck her.

Finally letting his cock slip from her mouth, Hilary thought long and hard about giving in and letting him fuck her. But in the end she decided that she could wait. She really didn’t want him jumping right from Reese to her, or vice versa, so with more than a little regret, she gave his cock a little pat before standing up.

“You’re mine tomorrow,” Hilary said, making damn sure he knew it wasn’t a request. She was going to fuck his brains out, probably all over her house, depending on how much energy he had.

Before he had the chance to respond, Hilary had already turned and distracted him with the sight of her ass in tight, denim shorts that had been cut off just barely past her butt cheeks. It really wasn’t fair how easily she was able to control him, but he wasn’t about to complain. At least not until she’d closed his bedroom door behind her and broken the spell.

“Well, I guess I better do a load of laundry,” Ben sighed, realizing his room reeked of sex and his bedding  was soaked in his and Reese’s love juices.

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