Stiff Competition 5

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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.

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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 Elisha Cuthbert, Debby Ryan, Hilary Duff, AnnaSophia Robb, Elizabeth Gillies, Victoria Justice, Jessica Alba, and Peyton Roi List. The codes are (MF, FF, cons, oral, anal, toys). Go fuck yourself and go read something else if you dislike those codes or want something more. Or better yet, write it yourself.

Stiff Competition 5

By voodoojoe

Anal Night

“I think we’ll do something a little different tonight,” Vanessa Hudgens announced to the camera. “Instead of drawing a name and a challenge, I think I’ll issue a challenge to everyone. From now until midnight, anyone that sends me a picture of themselves getting fucked in the ass gets twenty-five bonus points. I don’t care if it’s by a male or female. I’ll even let you fuck yourself in the ass, but only the first person to get the picture to me will get that bonus. So go, get your freak on, and make sure to get nice clear shots with your faces in the same shot as the cocks in your asses. And to keep you girls from fighting over who gets to take it in the butt, the girls doing the fucking get points as well.”

* * * * *

“We should do it,” Elisha Cuthbert said, nudging her longtime on-again/off-again fling, Joe Swanson, as they watched Vanessa’s video.

“Really? You just expect me to just up and fuck you in the ass just like that?” Joe asked with an almost straight face.

“I guess I could get my husband to do it,” Elisha said, smirking.

“Whoa, no need to do something desperate,” Joe said, grinning as he stood up.

“You set up the camera, I’ll get the lube,” Elisha said, dashing off.

“Grab the good stuff,” Joe hollered after her as he put her camera on a tripod.

While Joe set up the camera, and even arranged her computer to capture some video as a fail safe, Elisha rummaged through her toy box looking for her lube. While her husband was off playing hockey during the season she spent a lot of nights alone, and had the collection of toys to prove it. Though when Joe was in town and her husband wasn’t, she got to spend some time with a real cock instead of the fake ones.

“Aha,” Elisha said triumphantly, holding up a bottle of lube.

When Elisha returned Joe had already ditched his pants and was laying on his back. Popping the cap on the bottle Elisha squirted a healthy amount of lube into the palm of her hands before passing the bottle to Joe for him to do his part.

Joe had fucked Elisha in the ass enough over the years to have the drill down pat as she settled her pussy over his face. This wasn’t a sixty-nine though, something Joe was reminded of as Elisha wrapped her hand around his cock to smear lube along the length of the shaft.

As Elisha got his cock nice and slick Joe worked some lube into her asshole, making sure to slide his middle finger in and out of her tight hole a few times to make sure it was good. Then just to be safe, and because he wanted to, he fingered her asshole a couple more times.

Facing Joe’s feet, and the camera, Elisha moved down his body until she was hovering over his waist. Reaching down, Elisha grabbed hold of his cock and held it up as she lowered herself into position. With his cock pressed against her asshole, Elisha bit her lower lip and pushed, feeling the exquisite mix of pain and pleasure as her anus opened up to accept the large member into her ass.

“Ohhhh yeahhh,” Elisha moaned as she made little bounces on his cock, taking more of his cock into her ass each time.

Settling on top of Joe with his cock fully embedded in her ass, Elisha looked at the computer screen as an image of their joined bodies filled the screen. Right next to it was her camera aimed at the same thing, though zoomed out far enough to get her whole body in the frame, clicking off pictures every few seconds. Leaning back, she put a hand on Joe’s chest and lifted up, making sure to hear the shutter on the camera capture an image of his cock halfway up her ass.

With that taken care of, Elisha forgot, or at least ignored, the cameras. She had more important things to worry about, like the cock she was working in and out of her asshole.

Watching Elisha rise and fall on his cock, Joe marveled at her. Even in her thirties she was still extremely gorgeous, quite possibly even more so than she was in her teens. And while he got bored with most women after a handful of months, Elisha still managed to capture his interest after a decade. Some of that was probably because she was easily the hottest woman to ever touch his special areas, and some of it was probably because they only got together a few times a year so they never had enough time together to get tired of each other.

Grabbing Elisha’s hips Joe used them as leverage to lift his hips and meet her bounces. No matter how many he’d  fucked her ass over the years, feeling her tight asshole gripping and squeezing his cock was the best feeling in the world, though her silky smooth pussy wasn’t far behind.

“Uhh, fuck my ass, Joey baby,” Elisha hissed, knowing that being called ‘Joey’ always got him to give her a little extra as punishment.

“Don’t fucking call me Joey,” Joe hissed, driving into Elisha’s ass. “Just for that, you’re sucking my cock.”

“Naughty boy,” Elisha moaned, letting him make one more thrust into her ass before lifting off his cock.

Licking her lips Elisha maneuvered into place between his legs. Grabbing his cock she took a moment to make eye contact with Joe as he propped himself up on his elbows to watch. Opening her mouth she slowly lowered her head until she could wrap her lips around the head of his cock.

“Taste that ass all over my cock,” Joe grunted as Elisha eagerly stuffed more of his cock into her mouth.

Murmuring in response, Elisha worked her way down his cock until she felt the head bump against the back of her throat. Taking a breath she reversed course and pulled back until just the head was left inside her mouth. Giving the head a nice suck, Elisha popped her mouth off his cock completely and bent the cock forward so she could lick around the base of the shaft.

“Should we make sure we got a good picture, or should we just keep going to be safe?” Elisha asked between licks.

“I vote keep going,” Joe said, grinning as Elisha turned around and dropped to hands and knees, waving her ass at him.

* * * * *

Staring at the glistening dildo in her hand, Debby Ryan felt a twinge of nerves mixed with a bit of excitement. Looking into the bathroom mirror, Debby reached behind her and used one hand to pull apart the cheeks of her ass while the other pressed the tip of the dildo against her asshole.

Grimacing slightly as she pushed the dildo into her ass, Debby paused with just the tip inside her. Knowing that Vanessa would require more, Debby resumed pushing  until she had several inches up her ass. Slowly pulling out Debby fucked her own ass with the dildo, working more into her asshole with each stroke until she felt the base press against the cheeks of her ass.

After hearing Vanessa’s challenge, Debby knew she had to do it. With two strikes against her already, she really needed the bonus points. Without them she’d probably have to do a lot more than take a dildo up her ass to acquire some from another contestant, like letting the Michalka sisters spit roast her for an hour or two.

Grabbing her phone off the bathroom counter, Debby turned her back to the mirror. Putting a foot up on the edge of the counter so spread her legs, she reached back and grabbed hold of the dildo. Framing the picture so it got her face as well as a reflection of her ass with the dildo hanging out it, Debby snapped the picture.

After quickly sending the picture off to Vanessa, Debby put the phone back down on the counter. She thought about taking the dildo out of her ass, but decided if she’d already gone through the pain and trouble of inserting it into her asshole, she might as well finish the job.

So leaning against the counter Debby started to slowly fuck herself in the ass with the dildo. Pressing her ample tits into the counter top, she slipped her free hand underneath her to rub against her clit. The combination was electric as Debby worked herself over with the kind of care that boys never seemed to show.

The first time Debby had drawn an anal challenge she’d been nervous, having never even really thought of taking it in the ass, but Brenda had been so gentle that she was shocked when she came with the strap on fucking away at her virgin ass. She was even more shocked when it was followed a few minutes later by another orgasm.

The first couple times Debby had let a guy butt fuck her though hadn’t been nearly as nice. One of them hadn’t been bad with a nice little orgasm to show for her efforts, but the other one had been rushed and painful and if hadn’t been for that first experience, she probably would’ve sworn off butt sex forever. But she’d persevered and discovered that if she told the guy what she wanted, it made it infinitely more enjoyable for both of them.

Hands moving faster, both the dildo and the finger on her clit, Debby’s breathing got shallow and heavy. Her hand expertly worked the toy into her anal cavity, filling her up perfectly as her finger molested her clit. It was working perfectly as she felt her orgasm start to build inside her.

Spreading her legs and instinctively lifting her ass to push against the dildo, Debby grunted each time the toy bottomed out nine inches inside her, well, bottom. The toy was not only long, but it was quite thick as well, stretching her asshole deliciously until she could feel every bump and fake vein on the shaft pass through her anus.

Just as Debby was approaching orgasm, she heard her phone buzz next to her. She groaned at it but she was too close to do much more than glance in its direction before turning her attention back to the dildo sliding in and out of her asshole.

“Uhhhh,” Debby moaned, her legs quivering as she felt the first blush of climax.

As the ecstasy hit her full force Debby pushed the dildo as deep into her ass as she could, until the base pressed against the cheeks of her ass. Resting her head on the counter Debby’s toes curled, lifting up onto the balls of her feet as her body instinctively humped against the finger and toy that were bringing it such pleasure.

“Ahhhhhhh,” Debby shuddered, her body shaking as she came hard.

Once the orgasm had taken its course she shakily reached for her phone. Propping herself up on her elbow she picked up her phone and saw that she had a text from Vanessa. Her eyes went wide when she read it.

“2x pts ATM. Need vid,” the text read.

Shrugging her shoulders, Debby spread her legs nice and wide. Switching to the camera, she started recording video as she aimed it at the dildo still sticking out of her ass. Grabbing the base with her other hand she made a show of pulling it out of her ass, even giving Vanessa a nice little lingering shot of her gaping asshole before turning the camera back to the sex toy.

Making sure to keep the dildo in the camera’s sights as she raised it to her mouth, Debby took the head between her lips. With one eye on the screen of her phone and the other on toy in her mouth, Debby set about sucking the dildo clean of her own ass juices.

Ass-to-mouth wasn’t her favorite thing in the world, but if Vanessa was going to offer double points, Debby was going to take them. Pretty much anything else she’d have to do for extra points would likely involve her sucking a soiled phallus as well, so she might as well get them from Vanessa.

While she preferred to get fucked in the ass by girls, she much preferred going to ass-to-mouth with real cocks over fake ones. Actually, in general she preferred sucking real cocks to fake ones, but there was just something so amazing about feeling a real pulsing cock in her mouth right after it had been up her ass. Probably because it never failed to get the guy really turned on to watch her do something so kinky and perverted, even the more experienced ones that had seen everything, like Vanessa’s Boys.

Debby didn’t have enough experience or desire to deep throat, but she knew Vanessa wouldn’t require that. Vanessa just wanted to see Debby taste herself and as Debby worked the first few inches in and out of her mouth, it was more than enough to earn the points.

* * * * *

On her hands and knees, AnnaSophia Robb moaned and let her mouth hang open as the double-ended dildo was eased into her asshole. As the toy neared the halfway mark AnnaSophia couldn’t believe she had nearly nine inches of fake cock up her ass.

“You really do have an amazing ass,” Hilary Duff said as she fed the toy into the young blonde’s ass.

“Uhh, thanks,” AnnaSophia gasped, her eyes rolling up in her head as Hilary started to withdraw the dildo.

While Hilary and AnnaSophia might have seemed like an odd couple, they’d actually known each for a couple years. Hilary had actually been the one chosen to initiate AnnaSophia into the competition, with a thorough and complete fucking of every hole in her body. Since then they’d stayed in touch, getting together every so often to fuck up a storm when they both had free time.

The kid was with his dad, so Hilary was going to get laid. And since Vanessa had gifted them a perfect excuse, Hilary had picked up her phone and informed AnnaSophia in no uncertain terms that she was coming over. Not that AnnaSophia would’ve bothered to argue or anything, but she’d started getting wet from the she’d seen Hilary’s name on the screen.

“Want more, or are you ready?” Hilary asked, holding ten inches of purple cock in her hand, the other eight inches hanging out of AnnaSophia’s asshole.

“I’m ready,” AnnaSophia answered, moaning as she felt the toy being jostled inside her.

Turning her head AnnaSophia felt her pussy spasm when she saw Hilary smearing lube along the length of the other end of the dildo. Hilary had only lubed up AnnaSophia’s end at the start to make sure she could grip it as she pushed it into AnnaSophia’s ass. But now that AnnaSophia was ready, it was Hilary’s turn.

Still holding onto the end of the dildo, Hilary moved until she was facing away from AnnaSophia. Backing up, she positioned the tip of the dildo against her own anus. Forcing herself to relax Hilary pushed back, moaning as the toy penetrated her asshole.

“Ohhhhh,” Hilary moaned, pushing more of the dildo into her ass.

“So hot,” AnnaSophia hissed, watching Hilary in the mirrored closet doors.

“So big,” Hilary grunted when she finally felt her ass cheeks press against AnnaSophia’s.

“Wow,” AnnaSophia said, surprised by how sexy it felt to be ass-to-ass with Hilary, especially with a nice big dildo between them.

“Uhh, take the picture,” Hilary said, pulling forward and twisting her body enough to give a clear view of the dildo penetrating both their asses in the mirror.

“Smile,” AnnaSophia said, holding up her phone. Framing it to get both their faces in the shot, AnnaSophia snapped the picture.

Setting the camera down, AnnaSophia could’ve easily sent the picture to Vanessa and called it a day. But the dildo felt so good in her ass, she didn’t want to be finished quite yet. Luckily, Hilary felt the same way.

Clenching her asshole around the toy, Hilary pulled forward, drawing the toy with her. As she did so, it slid out of AnnaSophia’s relaxed asshole, causing the petite blonde to moan. When the toy was a little over halfway out of AnnaSophia, Hilary pushed back, driving it back into AnnaSophia until their butt cheeks slapped together.

“Ohhhhh,” AnnaSophia cooed, both at her ass being filled again and the feel of Hilary’s ass against hers.

Having done this with Hilary before, AnnaSophia clamped her asshole around the toy this time. Her turn to lean forward, she looked in the mirror and when she saw several inches of dildo outside of Hilary’s ass, AnnaSophia pushed until she felt the jolt of their asses slamming together.

“Fuck my ass,” AnnaSophia groaned as Hilary took her turn to clutch the dildo and lean forward.

Slipping a hand underneath her, Hilary found her clit, moaning as she timed it so that her first touch of her little nub coincided with AnnaSophia driving the dildo into her ass. Then as she gripped the toy with her ass she frigged her clit as she pushed back at an insistent AnnaSophia.

And so it went, each time their asses slapped together, the other one took control of the dildo. They worked like a well coordinated team, each drilling the other’s ass with a thrust before relinquishing control for a thrust. That way they both got to fuck and be fucked at the same time.

“OHHHHHH,” AnnaSophia howled as Hilary slammed the toy into her ass and triggered her orgasm.

As AnnaSophia came, her ass seized the toy tightly so Hilary took the opportunity to unclench her anus and let it slide in and out of her asshole freely with each thrust she made. In no time it worked as she slipped two fingers into her pussy and slammed her ass back onto the toy.

“Fuuuucckkkkk,” Hilary drawled as her own muscles tightened up and rippled with sexual release, her sphincter milking the hard piece of plastic lodged in her asshole.

* * * * *

“Say cheese,” Liz Gillies said as she aimed her camera to capture both Victoria Justice’s face and the strap on a couple inches inside Victoria’s ass at the same time.

“Cheese,” Victoria said, her smile turning into a gasp as Liz took the picture and then shoved the rest of the strap on into her ass in one thrust. She was lying on her back with her legs pulled back to her chest to give Liz unfettered access to her backdoor.

“Such a hot little ass,” Liz grunted, slowly sliding the toy out of Victoria’s tightest hole.

Victoria’s ass had always been one of Liz’s favorite parts of her friend. For such a slim girl, Victoria really had a shapely butt. It tended to stick out there so invitingly, just begging to be fondled and played with, something Liz was never one to pass up.

“Harder,” Victoria hissed as Liz went at half speed, knowing that Victoria was a bit of a butt slut that liked it hard.

Liz had always loved fucking Victoria, going back to the first time. Victoria had walked in while Liz had been going down on Ariana Grande and before Victoria could move, Liz had pulled Victoria down onto the couch next to Ariana. Rather than be mad at being interrupted, Ariana had gleefully helped Liz strip Victoria naked and the two of them had spent the next several hours partaking greatly in the wonders of Victoria’s body.

After that, the three of them got together in various combinations several times a week right up until their show had been canceled. Even after that though, Liz still made sure to hook up with each of them whenever their increasingly busy schedules permitted.

“Like this?” Liz asked, driving her strap into Victoria’s ass hard enough to make the room echo with the sound of their bodies slapping together.

“Uhhh, yeah,” Victoria gasped, feeling that amazing combination of pleasure with just smidge of pain as Liz violated her asshole. “Fuck my ass.”

Gripping Victoria’s thighs, Liz drove forward, burying her strap on into Victoria’s ass over and over. Liz’s hips were Victoria’s pelvis with enough strength to make her breasts bounce wonderfully, giving Victoria a nice bonus to go along with the ass fucking.

Where Liz envied Victoria’s slender frame and bubble butt, Victoria had spent quite a bit of time wishing she had tits like Liz’s. That had translated into more than a little time lavishing them with all sorts of attention. Victoria figured she knew them even better than her own and probably could’ve picked them out blindfolded she’d spent so much time squeezing and fondling them over the years.

“You’re such a fucking slut, you know that?” Liz hissed as Victoria slipped a hand down to frig her clit.

“Yeah,” Victoria mewled, dipping a finger into her pussy and feeling Liz’s toy sliding inside her through the thin membrane separating her holes. “Huge slut.”

“Beg me to fuck your ass,” Liz snarled, feeling the other end of the strap on rub against her clit pleasurably with each thrust into Victoria’s asshole.

“Fuck my ass,” Victoria moaned, her pretty face contorting in pleasure each time Liz plunged forward. “Fuck it so hard.”

“I said beg,” Liz said, drilling into Victoria’s ass and then stopping to rotate her hips and stretch out Victoria’s anus a bit before sliding back out.

“Please fuck my ass,” Victoria pleaded, her finger flying on her clit as Liz’s cock in her ass got her more and more worked up. “Oh god, please make me come all over your cock in my ass.”

“Not yet,” Liz said, grinning evilly as she suddenly yanked the toy from Victoria’s ass. “I think you should earn it.”

“Oh no, anything but that,” Victoria said, playing along as she realized what Liz had in mind.

“Oh yeah, suck your fucking ass juices off my cock, now,” Liz said, grabbing Victoria’s hand and pulling it away from her pussy.

While Victoria would’ve preferred to have Liz keep fucking her until she came, she wasn’t too upset about stopping. Ass-to-mouth turned her on greatly, so it wasn’t exactly a chore for her as she rolled over and swung around to face Liz.

Grabbing the base of the toy, Victoria wrapped her lips around the tip. Tasting her own ass on the surface, Victoria pushed down, taking more of the fake cock into her mouth. When she felt the dildo press against the back of her mouth, Victoria swirled her tongue around what was in her mouth as she pulled back.

“Turn around,” Liz commanded when Victoria had popped her mouth off the strap on.

“Yes, ma’am,” Victoria said, grinning as she turned around and presented her ass to Liz.

Moving in behind Victoria, Liz aimed the strap on at Victoria’s still gaping asshole. Pressing the tip against the opening, Liz pushed forward, watching her toy disappear up Victoria’s ass once more. While she didn’t go too fast, it only took a few seconds before she had the whole thing buried in Victoria’s asshole.

“Ohhh fuck,” Victoria moaned as she felt Liz’s pelvis press against her ass.

“Fuck is right,” Liz snarled as she immediately started withdrawing the toy.

With Victoria already primed, Liz didn’t bother with the niceties. The moment she had a little over half of her dildo outside Victoria’s ass, she slammed forward, driving back into Victoria’s butt and then pulling back. Over and over Liz thrust into Victoria’s tight little ass, driving the Latina increasingly crazy with each hard push she made.

“Whose ass is this?” Liz sneered, pulling on Victoria’s hips as she impaled her friend.

“Ohhhh, yours,” Victoria moaned, her hand finding its way back to her pussy to play with herself while Liz drilled her ass.

“Fuck yeah it is,” Liz snarled, slamming into Victoria’s ass with as much force as she dared.

“Ohhhh, make me come, Lizzie,” Victoria begged, the air being driven from her between each word with Liz’s thrusts.

“I love making you come from being ass fucked,” Liz grunted, her lips curling in concentration to show off her teeth as she fucked Victoria’s ass.

“Uhhh, sooo close,” Victoria moaned, her eyes shutting as she dipped two fingers into her pussy to feel the large toy sliding in and out of her asshole.

“Come for me, Vicky,” Liz hissed, wanting to push her friend over the edge. “Come from having my cock buried so deep up your ass you’ll still be feeling it next week.”

“Fuck me, Lizzie,” Victoria moaned, her body starting to shake with the early onset of her climax.

Sensing that Victoria was about to get her cookies, Liz buried her toy to the hilt in Victoria’s ass. Swirling her hips Liz leaned forward and grabbed Victoria’s tits. Pinching the nipples between her fingers, Liz kneaded Victoria’s breasts and made short strokes into her friend’s ass.

“Ohhhh gooooddddd,” Victoria moaned as she felt her orgasm slam into her full force.

“That’s it, Vicky, come for me,” Liz hissed into Victoria’s ear.

“I am,” Victoria mewled. “I’m coming so hard.”

“Ready for another taste of your ass?” Liz asked as Victoria’s body shook with ecstasy.

“Mmmm, yeahhh,” Victoria moaned, her arms going from under her, sending her sprawling face down on the bed.

Feeling Victoria’s asshole go slack, Liz yanked the toy out of her ass. Moving up the bed, Liz rolled Victoria onto her back. Squatting over Victoria’s face, Liz took hold of the base of the strap on and aimed it at Victoria’s open mouth.

“Mmm,” Victoria moaned around the dildo as Liz pushed more of it into her mouth.

“That’s it, suck your ass off my cock,” Liz snapped, sliding the toy in and out of Victoria’s mouth. When she was satisfied with Victoria’s work, Liz finally removed the dildo from Victoria’s mouth and sat back on the bed. “That wasn’t bad, if I do say so myself.”

“Next time it’s my toy and your ass,” Victoria said, grinning as she watched Liz unbuckle the harness and slide it down her legs.

* * * * *

“I don’t know about this,” Peyton List said nervously as she felt the stiff piece of plastic press against her virgin asshole.

“You’ll love it, I promise,” Jessica Alba said, drooling over the prospect of taking the pristine teen ass in front of her and making it hers.

After Selena had seduced her and popped her cherry, Peyton had gone a little wild. Okay, so maybe a lot wild. She’d discovered how amazing sex could feel, and no longer had to worry about the pain of having her hymen busted open, so she’d spent the last couple months fucking up a storm.

The day after Selena, Peyton had let Debby Ryan fuck her. A month or so after that she’d met Jessica at a party and she’d been putty in Jessica’s hands. By the end of the night Jessica had already dragged her into a coat closet and licked her pussy to two orgasms. She’d then taken the panties Peyton had been wearing and told her she’d have to call her later to reclaim them.

The next day Peyton had called Jessica like she’d been told. But when she’d gone to retrieve her panties, Peyton had wound up on her back with her feet straight up in the air with Jessica driving a large plastic dildo into her tight little cunt while she came over and over. Finally after who knows how many orgasms Peyton had begged Jessica to stop. On unsteady knees she’d gotten dressed to go home.

But after the fucking Jessica had given her, Peyton hadn’t been able to stay away. Every few days, maybe couple weeks, depending on when she could get away, Peyton found herself getting fucked silly by Jessica in all sorts of positions and locales.

There was one thing Peyton had denied Jessica though, and it was the one thing Jessica wanted more than anything at the moment. She’d been trying to talk Peyton into anal ever since their third encounter, and Peyton had finally seemed open to the idea. It might have had something to do with Jessica spending a good half hour licking her ass until Peyton’s brain had gone too numb to object when Jessica had suggested she put on her strap on and fuck her virgin ass.

As Peyton started coming to and realized what Jessica was doing, she’d started getting nervous. Jessica’s tongue on her starfish had felt amazing though, so Peyton wasn’t saying no, but she needed a firm hand willing to push a little and get her past her nervousness.

Luckily for both of them, Jessica had enough experience ass fucking women to know the difference between a girl that really didn’t want to do it and one that was just apprehensive. And as she pressed the tip of the toy against Peyton’s anus, Jessica stroked Peyton’s skin and cooed reassurances.

“Holy fucking shit,” Peyton gasped, her eyes going wide as Jessica pushed forward, forcing open her virgin asshole as the tip lodged inside it.

“Relax,” Jessica said, pausing to give Peyton a little time to adjust to the fake cock invading her ass.

“Too big,” Peyton grunted, grimacing in pain.

“Just relax,” Jessica said, using her phone to take a quick picture of her strap on just barely sticking out of Peyton’s deliciously pale ass.

As Peyton started to relax, Jessica pushed forward just a little. When Peyton groaned and tightened up, Jessica slowly pulled back until the toy was almost all the way out of Peyton’s ass. Pushing forward again Jessica made a bit more progress into Peyton’s asshole.

“Fuck,” Peyton hissed as she felt a small twinge of pleasure buried under the pain.

Recognizing the tiny shift in Peyton’s voice, Jessica got a little more insistent with her thrusts. Each one burrowed a little deeper into Peyton’s bowels and had a little more power behind them as Jessica sought to plunge every inch of her strap in into Peyton’s no-longer-virginal back door.

“Uhhh,” Peyton grunted as Jessica worked three-quarters of the toy into her.

“That’s it, Peyton,” Jessica said as she watched Peyton start to get into being sodomized.

“Oh god,” Peyton groaned when she finally felt Jessica’s pelvis press against the cheeks of her ass.

With as much of the dildo in Peyton’s ass as she could get, Jessica paused and reached forward to cup Peyton’s tits. They weren’t huge by any stretch, but they fit perfectly on her slim frame and were more than enough to fit satisfyingly in the palms of Jessica’s hands.

Cupping Peyton’s tits, Jessica slowly withdrew about half of her toy. Pushing back into Peyton’s ass, Jessica was pleased to hear Peyton moan in pleasure when she bottomed out once more. Using Peyton’s tits as handholds, Jessica started making short thrusts into the teen, butt fucking her with not quite half of her dildo.

“Ohhhh,” Peyton moaned, still feeling a little pain, but it was rapidly being overwhelmed by the pleasure, not to mention the naughtiness of what she was doing.

Increasing the speed and power of her thrusts with each plunge into Peyton’s asshole, Jessica followed Peyton’s lead. It was a lead Peyton didn’t know she was showing, but Jessica was experienced enough to read Peyton’s body language and go from there. And at the moment, Peyton’s body language was begging for Jessica to push her even though Peyton herself seemed nervous with all the brand new sensations bubbling up inside her.

“What do you want?” Jessica asked, wanting to hear Peyton admit what she wanted.

“Fuck me,” Peyton moaned, pushing back against Jessica’s thrusts.

“Fuck you where?” Jessica asked, letting go of Peyton’s tits and straightening up behind the blonde teen.

“Fuck my ass,” Peyton said, feeling a surge of naughtiness at begging to be fucked in the ass.

“I bet you want it hard, don’t you?” Jessica asked, pulling out almost the entire length of the strap on before tugging on Peyton’s hips and driving every inch of it back into Peyton’s ass.

“Ohhh fuck,” Peyton groaned, her rolling up in her head as Jessica started fucking her with the full length of the dildo.

“I think that’s a yes,” Jessica said, grinning as she repeated the feat.

“Ohhhh,” Peyton said, letting out a guttural moan as Jessica stopped taking it easy on her and really started to fuck her ass.

As Jessica slammed into her ass, Peyton tried to focus on not being overwhelmed by it. Her asshole was wrapped tightly around Jessica’s strap on and each thrust ignited nerve endings in her anus that she hadn’t even known existed. It was all so hot that even the dull ache of having her asshole stretched so far beyond anything she’d ever experienced before was barely registering in her brain.

“Give in to the pleasure,” Jessica said, realizing that Peyton was still trying to hold back. “Give in and let yourself come from being fucked in the ass.”

“Ohhh yeah, fuck my ass,” Peyton moaned as she felt Jessica’s pelvis crash into her butt cheeks with each thrust.

“So fucking tight,” Jessica grunted as the tightness of Peyton’s ass started taking a toll on her.

“So fucking big,” Peyton moaned, pushing back to meet Jessica’s thrusts.

Peyton couldn’t believe how amazing it felt to have something sliding in and out of her ass, especially something so big. It felt kinda like how she imagined a baseball bat being shoved through a keyhole would feel, except somehow it sent all sorts of tingly sensations shooting through her body. And somehow, against all odds, Peyton felt herself on the verge of a rather sizable orgasm from having her asshole reamed out by a fat cock.

“So close,” Peyton mewed as she sought release.

Feeling herself getting close as well and wanting to make sure Peyton got her reward for being such a good little slut, Jessica slipped a hand underneath her teen lover. Peyton bucked against her, impaling herself even deeper on Jessica’s toy than ever before, when she felt Jessica’s fingers make contact with her sensitive clit.

“Oh god, I’m coming,” Peyton howled, fingers curling into fists around the sheets on the bed as her asshole clamped down on the toy buried inside it.

Listening to Peyton’s squeals, not to mention the way her ass was pushing the other end of the strap on against her own pussy, pushed Jessica right to the brink. Slamming the toy into Peyton’s ass with as much force as she could manage, Jessica threw her head back and let herself go with a loud roar of pleasure.

With her body already quivering and depleted, the force of Jessica’s final thrust was enough to throw Peyton off balance. Her arms giving out, Peyton fell forward onto the bed, pulling Jessica with her as she landed face first with Jessica’s body weight on top of her.

Putting her hands on the bed Jessica pushed herself up on shaky arms. Keeping the dildo lodged deep in Peyton’s ass, Jessica shifted around so she could get onto her knees without pulling out.

Grabbing her phone, Jessica put one hand on Peyton’s ass. Using the hand to pry open Peyton’s tight cheeks, Jessica used her other hand to take a couple pictures of her strap on buried to the hilt inside the blonde’s tightest hole. Finally pulling out, she withdrew slowly, making sure to snap a couple more pictures.

When the toy came free of Peyton’s ass with an audible pop, Jessica decided to see just how slutty Peyton could be. Grabbing the base, she walked on her knees up the bed. Rolling Peyton onto her back, Jessica presented the filthy toy to the young blonde.

“Eww, what a-,” Peyton started to ask before Jessica cut her off by stuffing the dildo into her open mouth.

At first Peyton wanted to be mad and disgusted as Jessica forced her to suck the dirty toy, but as Jessica started to push more of the strap on into her mouth Peyton started to get aroused. Initially it was more about being controlled and dominated, but then she started to think about how nasty it was her taste her own ass and soon she was feeling an excited shudder go through her body.

“Smile,” Jessica said, pausing with half of the strap on in Peyton’s mouth to take a picture.

Doing as she was told, Peyton smiled around the dildo. The view through the screen of her phone was so hot Jessica almost forgot to take the picture, but she managed to snap herself out of her reverie to press the button and heard the click of the shutter burning the image into the memory.

“Wow, that was a good one,” Jessica said, looking at the picture on her phone as she slipped the dildo out of Peyton’s mouth.

“Promise you won’t send it to anyone?” Peyton asked as Jessica showed her the picture.

“Only you,” Jessica said, telling a little white lie. Or a big fat lie, but Peyton didn’t need to know about the real reason for the pictures at the moment.

* * * * *

“Wow, look at that,” Vanessa Hudgens said as she looked at the pictures of Peyton with Jessica’s dildo up her ass. “Not only does Jessica get bonus points for Anal Night, but she also cashed in the bounty on Peyton’s ass. Looks like we’re going to have quite the little anal slut on our hands. Better start brainstorming ideas for her initiation now because I want her in the game as soon as she turns eighteen. Now if we could just get Bella Thorne’s ass violated.”

“That’s already been taken care of,” Vanessa’s sister, Stella said, popping into the frame.

“Wait, what?” Vanessa asked, turning to look at Stella.

“Bella’s ass, it’s been taken care of,” Stella said, shrugging.

“Since when?” Vanessa asked, wondering how she didn’t know.

“Like months ago,” Stella said. “Me and Sammi took turns fucking her until she could barely walk the next day.”

“And you never told me?” Vanessa pouted.

“Because you tell me everything?” Stella countered.

“What are you talking about, I tell you everything,” Vanessa said.

“Like the thing with Jennifer Lawrence last week?” Stella asked.

“Wait, how’d you find out about that?” Vanessa asked, raising an eyebrow before turning to the camera. “Anyway, I’ll be back to draw a name tomorrow, so make sure to check back then.”

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