Stiff Competition 3

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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.

Harrington, DE (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 Stella Hudgens, Ashley Tisdale, Kate Upton, Vanessa Hudgens, Elizabeth Gillies, Selena Gomez, Peyton Roi List, and Kendall Jenner. The codes are (MF, FF, cons, oral, anal, inc, first, 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 3

By voodoojoe

Hazing Fun

“Since she’s now eighteen, my little sister, Stella, wants to join our little competition,” Vanessa Hudgens announced to the camera, letting it zoom out to show the younger girl sitting next to her. “So today we get to have our little hazing ritual. Are you ready Stell?”

“I’ve been ready for months,” Stella said, excited.

“To make sure no one could accuse me of taking it easy on you, I decided to let everyone out there decide what you should have to do to prove you want to be in the contest,” Vanessa said. “Suggestions ranged from a gangbang of like twenty guys, which I rejected because I just don’t have that kind of manpower on hand, to something as simple as eating Selena’s pussy. I think we all know who submitted that last one.”

“I’d eat Selena’s pussy even if it wasn’t a challenge,” Stella said, looking into the camera. “Seriously, anytime, anywhere.”

“You can answer that later,” Vanessa said as Stella’s phone predictably started ringing. “Anyway, I picked a few of the better suggestions for your first task and then let everyone vote on it. And they picked double penetration by two fellow contestants. So I drew names the last time we had a meeting.”

“Who’d you pick?” Stella asked, suddenly feeling nervous. While she’d had sex with girls before and wasn’t a virgin in her pussy or her ass, the latter thanks to Vanessa, she’d never done all three at the same time.

“First name was Ashley Tisdale,” Vanessa said, making Stella squeal as the short blonde entered the room.

“Ash!” Stella said, throwing her arms around Vanessa’s BFF.

“Hey, Squirt, you ready?” Ashley asked, pulling open her robe, making Stella gasp at the sight of the strap on around Ashley’s waist.

“I let them pick what toys they want to use,” Vanessa said, herself staring at the rather large dildo dangling between Ashley’s legs. “So they might be a little on the big side.”

“You think?” Stella asked, her eyes glued to the biggest cock she’d ever seen, real or fake.

“The second name I drew for you was Kate Upton,” Vanessa said, directing Stella’s gaze to the busty supermodel walking into the room. She grinned as Stella’s jaw dropped at the sight of the statuesque blonde.

“Holy shit,” Stella said, her eyes shifting to Kate’s tits as she pushed her robe off her shoulders and let it slide down her arms. As her eyes followed the robe Stella gasped again when she saw that the dildo Kate had between her legs was almost as big as the one Ashley was wearing.

“Still want to do it?” Vanessa asked her baby sister.

“Yeah,” Stella said, trying not to panic.

Stella was nervous about taking one of those huge fake cocks inside her. The thought of taking both of them at the same time was scaring the hell out of her. But she knew Ashley wouldn’t hurt her and Vanessa was there to stop things if they got out of hand.

“Come here,” Ashley said, beckoning Stella to her.

When Stella stepped forward Ashley reached out and put a hand on the back of Stella’s neck. Leaning in she kissed the younger girl, feeling Stella relax as she returned the kiss. Finally breaking the kiss Ashley made eye contact with Stella and let her fingertips caress Stella’s jaw and neck.

“Lets get you naked,” Kate said from behind Stella, hoping someone else taking command a little might help Stella along.

“Okay,” Stella said, nodding her head as Kate reached around her to undo the knot holding her dress closed.

“Why don’t I lie on the bed and you can be on top?” Ashley suggested as Kate pulled Stella’s dress off.

As Ashley scooted back towards the center, Vanessa grabbed the webcam. She wanted to give the audience a nice vantage point, so while Ashley settled herself Vanessa aimed the camera so it was pointed at the action from the side.

When she was ready Ashley locked her eyes on Stella. Lifting her hand she crooked a finger at Stella, beckoning her best friend’s sister in the sexiest manner possible. In fact, Stella was so turned on Ashley’s seductive pose that she climbed onto the bed on autopilot.

Moving to straddle Ashley, Stella reached down and grabbed the dildo. Her fingers barely fit around it as she lifted up and aimed it at her entrance. Dragging the head of the dildo through her folds Stella transferred some of the fluids that were seeping out of her to the toy before pushing down and letting it ease into her.

“Ohhh,” Stella moaned as her pussy was stretched further than ever before.

As Stella slowly lowered herself onto the strap on, Ashley kept her eyes on Stella’s face. While she very much wanted to watch Stella’s tight little pussy stretching to accommodate the girth of the toy, she also wanted to watch the various emotions and sensations play out across Stella’s face. Besides, she’d always found that eye contact added so much more to the act.

Settling fully on top of Ashley, Stella felt impossibly full with the large dildo imbedded deep inside her. Taking a deep breath Stella pressed her knees into the bed and started to lift her body, letting the toy slide out of her. When she’d lifted up as far she dared, Stella reversed course and dropped back down, moaning loudly as she was filled again.

“That’s hot,” Kate said to Vanessa.

“You don’t know the half of it,” Vanessa said, watching her baby sister slowly rise and fall on top of her best friend.

After glancing at the computer screen to make sure the angle on the feed was fine, Vanessa picked up her phone. Aiming it at the couple on the bed Vanessa started filming, getting a little footage for her own personal use. But as she shot she kept finding her focus being drawn to Stella’s ass, particularly the little dimpled hole between her baby sister’s cheeks.

“Here, hold this,” Vanessa said, handing off her phone to Kate.

“Sure,” Kate said, taking the phone.

Kate wasn’t quite sure why Vanessa had passed it to her, but she wasn’t going to question the woman in charge of the competition. Regardless, she got her answer soon enough when Vanessa moved onto the bed behind Stella and pulled apart Stella’s butt cheeks.

“Oh shit,” Kate gasped as Vanessa leaned in and started lapping at Stella’s asshole.

“Oh god, yeah, eat my fucking ass, ‘Nessa,” Stella grunted, pushing her ass back against Vanessa’s tongue as she pushed down on Ashley’s toy. “Fucking lick your baby sister’s tight little ass and get it ready.”

“Here’s the lube,” Ashley said, handing a bottle to Vanessa.

“Mmm,” Vanessa said, blindly groping for the proffered item since she didn’t want to pull away from the yummy ass in front of her to locate it.

Popping the cap on the bottle Vanessa gave Stella’s ass one last lingering lick before pulling back. Squirting a healthy dollop of lube on her finger Vanessa slipped her finger between Stella’s butt cheeks. Finding the tight hole she rubbed around the outside before pressing against the center and pushing the digit into her sister’s gripping asshole.

“Fuuuuuckkk,” Stella grunted as her anus was penetrated.

With the dildo in Stella’s pussy, Vanessa’s finger felt huge in her ass. Once more she was struck by a sense of near panic as she tried to imagine how a dildo the size of the one around Kate’s waist could possibly fit in her tiny little ass. The only thing that kept her from begging out was the knowledge that if she stuck with it then she’d finally be in Vanessa’s contest and she’d get the fun and excitement that came with it.

“C’mere, Kate,” Vanessa said, adding a second finger to Stella’s ass to help stretch it out.

When Kate stepped forward, Vanessa withdrew her fingers from Stella’s ass. Grabbing the bottle of lube Vanessa squirted a stream along the length of Kate’s strap on. Setting the bottle aside Vanessa rubbed the lube around, making sure it was good and slick before grabbing a towel to wipe off her hands.

“Give it back,” Vanessa said, indicating her phone.

When Kate gave her back the phone Vanessa moved to the side, but not very far. As Kate moved in behind Stella Vanessa made sure to get a nice close up of the second dildo zeroing in on her baby sister’s asshole.

“Ready?” Kate Upton asked.

“Do it,” Stella said, closing her eyes.

As Ashley grabbed Stella’s ass and pulled her cheeks apart, Kate pressed the tip of the toy against Stella’s anus. Kate pushed gently but firmly and at first Stella seemed to tighten up and repel the invasion. With a little persistence though Kate soon felt the little starfish start to give way.

“Holy fucking,” Stella screamed in shock as her asshole was forced open.

It might be more than a bit of a cliche to say that Stella felt like a telephone pole was being shoved up her ass. Just because something is cliche doesn’t make it not true though and between the dildo in her pussy and the one just barely inserted in her asshole Stella felt like she was going to be ripped in two.

“Breathe,” Ashley said, moving her hands up to stroke Stella’s back and sides.

“It’s so fucking big,” Stella grunted, trying to adjust to pair of dildos inside her.

“I know, but try to relax,” Ashley said, smiling as she felt Stella take a deep breath above her.

“Good girl,” Ashley said, giving Kate the sign to push a little more into the teen.

“Fuck,” Stella gasped as another couple inches disappeared in her asshole.

“Is it feeling better?” Ashley asked Stella as Kate inched the dildo into her rectum.

“A little,” Stella whimpered as Kate lunged forward and finally buried the rest of the strap on into her stretched out anus.

“Fuck her, Kate,” Vanessa said, watching it all unfold through the screen of her phone.

With Stella still trying to come to grips with having both of her holes filled with large chunks of plastic, Kate pulled back. It wasn’t much, maybe a couple inches, but when she pushed back into Stella’s asshole the younger girl groaned and her eyes rolled up in her head.

“Come on, Stella, lets give your sister a show,” Ashley said as Kate a few inches of fake cock out of Stella’s ass.

“Oh god,” Stella moaned as Kate pushed back in with enough force for the sound to echo through the room. “Fuck me, both of you.”

With that, Kate started to slowly pump in and out of Stella’s asshole. Once Kate had set a steady rhythm Ashley followed suit, working her own toy into Stella’s pussy. Each time Kate pulled back Ashley lifted her hips and pushed into Stella’s pussy, then as she pulled out Kate filled Stella’s ass again.

“Holy shit,” Stella gasped as she felt the two dildos moving against each other inside her.

Even though she’d adjusted to being stretched so much, to say Stella had gotten used to it would be inaccurate. The pain was largely gone and what was left was no match for the sheer amounts of sensations that were coursing through her body. Every thrust ignited a new little part of her and as Kate and Ashley picked up speed the thrusts were coming faster and harder.

“So hot,” Vanessa said as she watched her baby sister get fucked by two hot girls at the same time.

Thrusting hard into Stella’s ass, Kate’s already enthralling tits jiggled and shook and demanded Vanessa pay attention to them. If it had been pretty much anyone other than Stella as the meat in the sandwich, Vanessa would’ve spent the whole time just staring those marvelous mounds of flesh. But it was her baby sister getting stuffed within an inch of her life so Vanessa focused more on the toys plunging into Stella’s holes. She would’ve been a complete idiot to not let her attention drift every so often up to the tidal wave of boob flesh Kate was putting on though.

“Ohhhhh,” Stella groaned as she felt an orgasm approaching.

Realizing that her little sister was about to come, Vanessa moved so she could get a nice shot of Stella’s face as she came. It was worth it as Stella let out a scream and clawed at the bed, her face contorting into a look of almost suffering, yet with an undercurrent of the purest form of ecstasy.

As Stella was hammered by her orgasm Kate and Ashley continued to fuck her. They slowed down a little to make up for the added tightness of Stella’s holes, but other than that they showed her no mercy. Both women continued to drive in and out of Stella, prolonging her orgasm until she finally slumped on top of Ashley.

Part of Ashley and Kate’s job was to keep going until Stella couldn’t take any more and begged them to stop. No one bothered to let Stella in on that piece of information though, so when Stella’s body went limp they increased their speed again until they were fucking Stella as hard, or maybe even harder, than that had been before her climax.

“Holy,” Stella hissed as she started to come around and found herself still being used as a fuck doll by the two women. It felt amazing to be at their mercy like that but Stella really wasn’t the type to sit by passively and let people do stuff to her without joining in.

As Ashley lifted up to drive her toy into Stella, Stella met her thrust with one of her own. Then when Ashley started to pull out Stella pushed back to meet Kate’s plunge into her ass. Of course that just encouraged the two of them to fuck Stella’s holes even harder, but Stella didn’t mind too much.

There was still a small modicum of pain underneath all the pleasure coursing through her, but not enough to make the situation unpalatable. If anything, it added a little something to the experience. Not enough to make her want to see if getting punched in the face made sex better or anything, but it still helped push her along a little.

“Uhhh, oh god, fuck my ass, Kate,” Stella grunted as Kate Upton pounded her ass into oblivion.

Turning her head Stella watched the look of concentration on Kate’s face as she fucked her ass. Sweat was pouring off Kate’s face and her blonde hair was mussed and matted with exertion. But what got Stella, like her sister, was the way those tits undulated and rippled with each thrust. It was a double whammy for Stella as each thrust sent incredible sensations shooting through her, but it also sent Kate’s tits bouncing in the most wonderful ways.

“Fuuuuckkk,” Stella grunted, already feeling a second orgasm sneaking up on her.

“Does little Stella want to come again?” Ashley asked, recognizing the look on Stella’s face.

“Yeahhh,” Stella murmured as Kate and Ashley continued to work her over.

“Mmm, just think about it, Stella,” Ashley said loud enough to be heard over the various grunts and sounds of flesh slapping together. “All those hot girls just waiting for you to fuck, or guys with hard cocks waiting to fuck you. They’re all yours when you’re done.”

“Gonna fuck ‘em all,” Stella mewed as she felt a massive orgasm building inside her like a hurricane.

“Mmm, they’re going to line up for a piece of you,” Ashley promised as she added a little extra power to her thrust.

“OHHHHHHH,” Stella screamed as her entire body was engulfed in ecstasy. Every muscle in her body clenched and constricted as electricity shot through her nerve endings. Everything in her field of vision turned a bright white as her eyes were flooded with an overabundance of light.

“Wow,” Vanessa said as she watched her baby sister come like a freight train.

And still Kate and Ashley continued to fuck Stella. As the younger girl collapsed on top of Ashley, barely capable of coherent thought, the two dildos kept slamming into her. They were relentless and just going and going, like the Energizer Bunny on speed or something.

“Fuck, stop stop stop,” Stella pleaded when she was finally able to form words.

“Had enough?” Ashley asked, finally slowing down.

“Pull out slowly,” Vanessa told Kate as the busty model started to remove the dildo from Stella’s asshole.

As Kate slid the dildo out Vanessa moved in and focused the camera on it. When it came out with a pop, Vanessa got a nice shot of her sister’s asshole, red and gaping from the punishment. Then she turned her attention to the dildo waving in front of her, shiny and slick from the lube and Stella’s juices.

“Here,” Vanessa said, handing off the phone to Kate.

Kate barely had time to grab the phone and refocus it before Vanessa took the dildo into her mouth. Kate moaned as she watched Vanessa suck the toy clean. What really shocked Kate though was when Vanessa took a deep breath with about half of the fake cock in her mouth, relaxed her throat, and then kept going until her nose was pressed against the harness.

“That’s why she’s in charge,” Ashley said, seeing the look of shock on Kate’s face.

“Mmhmm,” Vanessa murmured around the toy as she used her to tongue to lick off every bit of her baby sister’s essence from the surface.

With Stella still tired and weak from her sandwiching, Ashley helped her by rolling over. Now on top of Stella, Ashley pushed herself up and slowly pulled the dildo from the teenager’s pussy.

“Uhhh,” Stella groaned. After being stretched so far by the two dildos, she suddenly felt very empty without them inside her.

“Congratulations, baby girl,” Ashley said, bending down to give Stella a kiss. “Welcome to the competition.”

“Mmmm,” Stella purred, a big smile crossing her face.

* * * * *

“Look at my little sister, all sweaty and fucked out,” Vanessa said as Stella leaned her head on Vanessa’s shoulder. “But now she’s a full member of the competition.”

“Yay,” Stella said, a dreamy smile crossing her face.

“What d’ya say, Stella, feel up to drawing the next name?” Vanessa asked.

“Sure,” Stella said, reaching into the jar and pulling out a name. After handing the name to Vanessa she reached into the challenge jar and withdrew another piece of paper for Vanessa.

“Liz Gillies, you’re on the clock,” Vanessa said, reading the first paper. “And it looks like your challenge is to get tit fucked. Well at least she has the chest for it.”

“Mmhmm,” Stella agreed, turning her head to rest her chin on Vanessa’s shoulder.

“Liz has twenty-four hours to get it done,” Vanessa said, turning on the timer. “Doesn’t matter who does the tit fucking, it just needs to be a guy.”

Thanks For The Mammaries

“Uhhhhhh,” Elizabeth Gillies grunted loudly as the monster cock repeatedly plunged into her tight snatch.

“That’s it, Chuck, fuck that pussy,” Vanessa said, gleefully watching the action.

After drawing the challenge, Liz had called Vanessa to find out what exactly it entailed. Simply put, Vanessa informed her, Liz could do whatever she wanted to whoever she wanted. The only thing that mattered was that within twenty-four hours a man needed to press his cock into her cleavage, slide between her tits a few times, and then spew his cum all over her.

Then Vanessa had brokered a deal. One of her helpers had gone over and above the call of duty to keep a contestant from getting caught during a particularly sensitive situation. He’d been assigned to document Aly Michalka’s challenge to fuck a relative in a restaurant when he’d noticed a server about to enter the room. He’d managed to alert Aly and her sister and then stall the server long enough for the sisters to slip out a side door without being discovered.

Vanessa had thought about letting Chuck fuck Aly and AJ as a reward for his quick thinking, but then decided that Aly and AJ should do that on their own. But then Liz’s name had popped up, and figured that Chuck, being a fan of both big tits and pale white girls, might enjoy her.

So Vanessa had given Liz a few bonus points to let the big black dude with the huge cock have his way with her tits. And being a bit of a size queen Liz had decided that other parts of her could use some attention as well once she’d seen what Chuck was packing.

“So fucking big,” Liz hissed as Chuck slammed into her from behind.

Liz figured he must have been a good nine or ten inches long and as big around as her wrist. As her pussy clutched and gripped his cock she was actually kinda glad she’d resisted the urge to let him fuck her ass. She was pretty sure it would’ve felt amazing once she got used to it, but she was also sure it would’ve hurt like hell being ripped in half by the tree trunk he called a cock.

Gripping Liz’s hips Chuck settled into a nice pace fucking her doggystyle. He knew that he was pretty much just a piece of meat to Liz, and not much more than that to Vanessa, but as a single guy in his early twenties, it didn’t matter that much. What mattered most to him at the moment was that he was balls deep in a sweet little pussy.

Letting her head drop down to touch the bed, Liz pushed back to meet Chuck’s thrusts with as much power as she could muster. He’d been fucking her for a solid half hour, at least, and she’d already come multiple times. Her face was dripping with sweat as she got the best fucking she’d had in months, maybe ever.

“Almost there,” Chuck said, finally feeling himself near the point of no return.

“Pull out,” Liz grunted, torn. She really wanted to feel him come inside her, feel him shove as much of his cock into her as possible and then shoot so much jizz up her cunt that it would leak out around his cock. But at the same time she knew if she let him do that she’d lose the challenge and already have a strike despite being relatively new to the game.

Pulling out of Liz’s pussy, Chuck pushed on her hip until she toppled over onto her side. Quickly moving to straddle her he pushed her onto her back. Hovering over her chest Chuck squatted until he was practically sitting on her upper stomach just below the rib cage.

“Do it,” Liz said, putting her hands on the sides of her breasts and pushing them together around the large slab of meat between them.

As Chuck flexed his powerful glutes and began to slide his cock between Liz’s melons, Vanessa grabbed her camera. Pointing it at the action she started snapping pictures. On each cycle the cock would disappear into the fleshy tunnel of Liz’s chest and then he’d thrust forward and enough would stick out to threaten to bump Liz in the chin.

“Here it comes,” Chuck warned as he felt the cum start to rise up inside him.

Pushing forward Chuck grunted as the first jet erupted from the end of his cock. A thick rope struck Liz under the chin, dripping down her neck. Subsequent spurts splattered all over her neck and upper chest, leaving her already milky white skin dotted with jizz.

* * * * *

“Look at that pearl necklace,” Vanessa said, giggling as she showed the pictures to her viewing audience. “Chuck really gave it to her good.”

After finishing the slideshow Vanessa reached down and grabbed the jars and lifted them onto the table. Reaching into them both at the same time she swirled her hands around, mixing them up. When she was satisfied she dug through and grabbed a slip of paper from each and pulled them out at the same time.

“Ooh, this should be fun,” Vanessa said, grinning as she read the papers. “The jars have spoken and they say Selena Gomez in the kitchen with a virgin. Wait, sorry, I was playing Clue with Stella earlier. I mean Selena has to fuck a virgin. Bonus points if it’s a girl. Which means hymen intact, at least until you get through with her. Now go, you’ve got twenty-four hours.”

The way the bonus points worked was that each challenge had its own degree of difficulty. Bonus points made the challenge more difficult but added extra reward. A girl could go for the base challenge or she could shoot higher looking for valuable bonus points. But once she chose there was no going back and if she failed she got a strike and no bonus.

From there, once the points were granted it was up to the participant as to what to do with them. The most common usage was to cash them in to have a strike wiped off their record. Some, however, liked to trade them amongst themselves for stuff. Prices varied depending on how many points and how desperate the other party was to acquire them, but often at least one lewd sex act was involved in such point transfers.

Pop Goes The Cherry

After getting her challenge Selena had immediately started texting all her friends. She needed to find a virgin but no one she could think of fit that one very important criteria. Finally she’d gotten a text from Debby Ryan that had put some hope back into her.

Apparently Debby’s co-star, Peyton List was still clinging to her cherry. Even better, Debby reported that she was even open to a little girl-on-girl. In fact, Debby had even gotten her to engage in a little carpet munching a couple times but when the subject of a dildo had come up Peyton had balked and refused to go further.

Normally that might be considered a bad thing for what Selena had planned, but Selena wasn’t too concerned. Debby wasn’t exactly the overly aggressive type so if a girl said no Debby was likely to stop rather than push just that extra little bit to overcome a roadblock. Sometimes women wanted to play hard to get and make a person work, especially young virginal types. Selena was confident that Peyton was already mostly there, she just needed that extra little push.

Being a huge fan of Selena, Peyton had literally jumped at Selena’s invitation to hang out. Selena had said something about being a fan, which was one of the most amazing things Peyton had ever heard, so she’d quickly agreed and made an adjustment or two to her schedule to she could hang out with one of her idols.

Thus Peyton found herself sitting on the couch with a bowl of popcorn in her lap watching trashy reality television with Selena Gomez. Every time someone on screen did something stupid they’d made a joke and laughed and just generally had a good time.

After a couple hours, just enough time for Peyton to settle in and get comfortable, Selena made her move. Under the guise of reaching for popcorn Selena leaned over and kissed her, surprising the teenager and causing her to freeze for a moment.

While the move had been unexpected, it was far from unwelcome as far as Peyton was concerned. She’d experimented a bit with a couple friends so the idea of making out with another girl was far from unprecedented.

Feeling Peyton start to respond and return the kiss, Selena knew she had her. Pushing it to the next level Selena grabbed the bowl of popcorn without breaking the kiss and moved it to the coffee table. With that out of the way Selena slid her hand up Peyton’s leg, sliding under the pretty blonde’s skirt until she reached her crotch.

“Ohhh,” Peyton moaned as Selena’s fingers rubbed her pussy through her panties.

“You want me to fuck you, don’t you?” Selena asked, pressing her middle finger hard against Peyton’s clit.

“Yeah,” Peyton said, nodding as the fabric of her panties added friction to the equation and creating a sensation she’d never felt before.

“Show me how bad you want it,” Selena hissed, pulling her hand away. “Take off your panties and spread those legs for me.”

Not wanting to disappoint one of her idols, Peyton quickly slipped her hands underneath her skirt. Hooking her thumbs in the waistband of her panties she pulled them down, unceremoniously kicking them off before laying back and spreading her legs like Selena wanted.

“What a pretty little pussy,” Selena said, lifting Peyton’s skirt to get a better look. There was a small patch of short pubic hair above it but Selena was pleased to note that Peyton at least trimmed it up off the labia so she wouldn’t have to contend with hairballs when she was done.

“Lick me, please?” Peyton nervously pleaded.

“Such a naughty girl, wanting me to lick your pussy,” Selena said, tracing her finger up and down through Peyton’s folds without her panties in the way. “Is that what you are, a naughty girl?”

“So naughty,” Peyton agreed, lifting her hips to press her crotch against Selena’s fingers.

“Mmm, tell me what you want,” Selena said, kissing the inside of Peyton’s thigh a few inches below her eventual target.

“Lick me,” Peyton said, her hands resting on her stomach as she lifted her head to look down at Selena.

“Louder,” Selena said, kissing the inside of Peyton’s other thigh, a little closer this time.

“Lick my pussy,” Peyton said louder.

“Almost,” Selena said, moving in close enough for Peyton to feel her warm breath on her pussy.

“I want you to eat my pussy, ahhhh,” Peyton said, almost yelling before it turned into a loud moan when Selena gave her what she wanted.

Not wanting to give Peyton time to rest Selena went to work. She aggressively attacked the pussy in front of her, making Peyton writhe as Selena did stuff with her tongue the youngster had never experienced. It was all so much and Peyton felt herself being swept away on a tide of ecstasy.

“Ohhh, mmmm,” Peyton moaned, her eyes wide open as she soaked in every touch and lick Selena made.

“You like that?” Selena asked between licks.

“Yeahhh,” Peyton mewled, putting a hand on the back of Selena’s head and pushing it against her pussy.

“Then you’ll love this,” Selena said, reaching between the couch cushions to pull out the vibrator she’d secreted there.

“Huh?” Peyton asked until she felt something press against her slit. Lifting her head she looked down and saw Selena dragging the toy through her folds to wet the tip. “Wait, stop.”

“Stop what?” Selena asked, playing coy.

“No toys,” Peyton said, trying to push away Selena’s vibrator.

“Why not? Are you scared?” Selena asked, twisting the base the vibrator until it sprang to life.

“Ohhhh,” Peyton gasped as Selena pressed the toy against her clit, sending strong vibrations shooting through her.

“And that’s only on low,” Selena said, grinning as Peyton’s eye rolled up in her head from the new sensations. “Still want me to stop?”

“Noooo,” Peyton responded, her whole body quivering as she tried not to be overwhelmed.

She’d had her pussy licked a few times, even returned the favor a couple times, but she’d never played with toys before. Immediately Peyton realized that maybe she’d made an error in that though. The vibrator felt amazing with pleasure coursing through her radiating out from her clit, like waves after dropping a rock into a puddle.

“Good,” Selena said, drawing circles around Peyton’s clit with the tip of the vibrator. “Just wait until you feel it inside you.”

“Wait, I, um, uhh,” Peyton stammered as Selena’s remark registered.

“Don’t worry, you’ll love it,” Selena assured her, sliding the vibrator down until it was positioned at the opening of Peyton’s pussy.

“I’m a virgin,” Peyton finally blurted out. She wasn’t saving herself for marriage or anything, but when she’d pictured losing her cherry, it certainly had been to a vibrator wielded by another girl.

Those were the magic words Selena had been looking for. Rather than have one of Vanessa’s Boys lurking around outside watching, Selena had hidden a video camera instead. And while she didn’t completely need Peyton to admit to being a virgin to satisfy Vanessa, it sure would make it tough to argue the evidence.

“I kinda figured,” Selena said, moving up Peyton’s body. “It’ll only hurt for a moment and then it’ll feel amazing. But if you really want to stop everything.”

“No, I mean, uh,” Peyton muttered nervously as she faced the moment of truth. If she said no then she’d keep her cherry but Selena would stop when she was so close to coming.

“What is it, Peyton?” Selena asked, pushing the end of the vibrator against Peyton’s pussy just enough to let Peyton feel her labia start to open.

“Fuck me,” Peyton said, deciding that she wanted Selena to make her come.

Grinning at Peyton’s acquiescence Selena pushed forward, making Peyton grunt in pain as her hymen was torn asunder. Not giving Peyton time to think about the pain Selena leaned her head down and pressed her lips to the pretty blonde’s as she pushed several inches of vibrator into Peyton’s pussy.

With Selena’s tongue in her mouth and the vibrations from the toy rumbling and shaking the heretofore untouched inner walls of her pussy, the pain of losing her virginity was quickly overwhelmed. The discomfort was still there but as Selena slowly slid the still humming vibrator out Peyton moaned at the movement.

“How does it feel?” Selena asked as she slowly worked the toy in and out of Peyton’s vise-like snatch.

“Sooo goooood,” Peyton moaned, her hips lifting off the couch to hump at the vibrator every time Selena pushed it into her.

“And it’ll only get better from here,” Selena promised. “Later we can try a few other things now that you don’t have to worry about your cherry.”

“Mmm,” Peyton moaned at Selena’s promises.

“But first I want you to come for me,” Selena said, watching Peyton’s pretty face as it screwed up in a look of concentration.

“Uhhh,” Peyton grunted as her orgasm swelled. With each thrust Selena made it grow, each vibration adding to the pleasure amassing inside her.

“You’re getting close, aren’t you?” Selena asked, noticing the flushing in Peyton’s skin.

“Uhh, yeahh,” Peyton responded, nodding her head slightly as she felt her ab muscles start to tense.

“Then come for me,” Selena said, twisting the dial on the vibrator to increase the intensity.

The effect was immediate as Peyton’s eyes rolled back in her head. With a loud scream her hips shot up off the couch as the biggest orgasm of her young life ripped through her body. Shaking violently Peyton was completely unprepared for the level of pleasure shooting through her.

“Whoa,” Selena panted as she turned off the vibrator and watched Peyton collapse into a boneless puddle.

Pulling the toy from her lover’s pussy, Selena looked on with some envy and more than a little pride as Peyton’s face took on a dreamy quality. It was the kind of look a girl only achieved under certain circumstances, usually from getting fucked senseless.

Slipping off the couch Selena crossed over to where she’d hidden the camera. With Peyton still in her post-orgasmic stupor Selena grinned into the camera, even blowing a kiss to Vanessa before reaching up to turn it off.

* * * * *

“I think it’s safe to say we’ll be extending an invitation to Peyton when she turns eighteen,” Vanessa said as she played the video. “She’s going to be absolutely gorgeous in a couple years. Shit, she’s gorgeous now. In a couple years we’ll all be jealous of her.”

Reaching the end Vanessa restarted the video. Finding the moment when Selena busted through Peyton’s cherry, Vanessa put in in slow motion and watched the mix of pleasure and pain on Peyton’s face. It was such a hot moment that Vanessa played it several times.

“And with that Selena wins the challenge and gets the bonus points,” Vanessa announced. “She’d also like to let interested parties know that her points are available in case anyone wants to inquire about them. If you’re not willing to let her tie you to a bed with a ball gag in your mouth, then you should probably let someone else bid on them though.”

The Punishment Due

“Before we get to picking names, there’s still a punishment left to levy,” Vanessa said, turning the camera to show the tall, leggy brunette standing off to the side. “If you remember, Kendall was supposed to have sex at a sporting event but couldn’t get it done.”

“My sister wouldn’t let me out of her sight,” Kendall Jenner groused.

“Then she had to go work so I let her put off her punishment until now,” Vanessa said, reaching into a drawer and pulling out a butt plug still in it’s plastic clam shell package. “Your punishment is to walk around with this in your ass all day.”

“What?” Kendall asked, shocked. Normally punishments seemed to consist of spankings or maybe a little oral sex. She certainly hadn’t been expecting a butt plug.

“Come on, lift up that skirt and take off your underwear, if you’re wearing any, that is,” Vanessa said, opening the packaging of the sex toy.

Resigned to her fate Kendall did as she was told. Turning around she slid her hands under her skirt and hooked her fingers in the waist of her panties. As Vanessa doused the plug in lube Kendall slid her thong down her legs.

“That’s good enough,” Vanessa said, pushing Kendall forward.

Flipping Kendall’s skirt up Vanessa shifted the leggy model so her ass was facing directly into the camera. Prying Kendall’s tight cheeks apart with one hand Vanessa used her other one to bring the butt plug up to press against Kendall’s asshole.

Gasping at the cold feel of the lube Kendall closed her eyes and willed herself to relax as Vanessa eased the tip of the plug into her asshole. She’d engaged in anal a couple times so the penetration wasn’t too bad, at least not until the toy started widening past anything she’d ever felt in her ass before. But before she knew it she felt her anus close around bulbous end and the flat base pressed against the cheeks of her ass, holding everything in place.

“There we go,” Vanessa said, moving to the side to make sure the webcam got a nice view of the base sticking out of Kendall’s ass. “Until you come back here for me to take it out in four hours, it is not to leave your ass, except maybe in the bathroom. I’m going to call you at random times and you will answer. Then you have two minutes to find some place to take a picture of the plug still in your ass and text it to me. If you don’t answer or don’t text me the picture, you fail, get a second strike, and another punishment. Do you understand?”

“I think so,” Kendall said, straightening up.

“Good,” Vanessa said, helping Kendall pull up her thong. “And I will be checking the time stamp on the pictures so you can’t keep sending me the same picture or take several in different rooms or from different angles and then send them to me as if you just took them.”

“Okay,” Kendall said, already squirming from feeling the firm lump of silicone lodged in her rectum.

“Then be back here in four hours,” Vanessa said, giving Kendall a nice swat on the butt that made the teen yelp from the shock wave of the spanking causing the butt plug to move and rub against the inner walls of her bowels.

* * * * *

As Kendall went through her day the butt plug drove her nuts. Every step caused her anus and rectum to flex and contract around it. Even when she sat down and tried to forget that it was there, she’d cross her legs and feel it rubbing around inside her.

By the time she pulled up in front of Vanessa’s house her pussy was practically dripping with arousal. She really hadn’t enjoyed anal the couple times so the thought of a butt plug feeling that good had been a foreign concept. But between the seemingly constant stimulation and the naughty feeling she got every time someone looked at her and she wondered if they could tell she a little something extra under her skirt, it was easily the most aroused she’d ever been without direct contact to her pussy.

“You’re a little early, but you can wait a little,” Vanessa said, greeting Kendall at the door.

“Thanks,” Kendall said, moving past Vanessa and into the house.

“I guess I should make sure you’ve still got it in,” Vanessa said, grinning even though she could tell from the slight hitch in Kendall’s step that she was still wearing the plug. It wasn’t major and if Vanessa hadn’t been looking for it specifically she never would’ve known.

With her back to Vanessa Kendall reached back and lifted up her skirt. Sure enough there was the flat base of the toy peeking out from underneath the strap of Kendall’s thong. Also highly visible was the large wet spot on Kendall’s panties from the stimulation.

“Someone enjoyed their day,” Vanessa said, smirking at Kendall’s obvious arousal.

“You have no idea,” Kendall moaned, turning around and letting the skirt drop back into place. “Or maybe you would, I don’t know. But every time you called and I had find a bathroom or closet or something to take a picture of this thing in my ass, I got so hot.”

“And yet you couldn’t do anything about it, could you?” Vanessa asked, smirking as she nodded for Kendall to follow her to the spare room she used as contest headquarters.

“If I’d known what it was going to be like I would’ve stayed home and just spent the day fucking myself instead,” Kendall said, following Vanessa.

Opening the door Vanessa motioned for Kendall to step inside. As Kendall moved over to the bed she started to sit and then seemed to think better of it. Straightening back up she milled around as she waited for Vanessa to get everything booted up and ready to broadcast.

“Well, now that we’re four hours later, our friend is back,” Vanessa said, turning the camera momentarily to show Kendall. “Though I’m not sure she really wants to have her butt plug removed because she absolutely loved it. Her panties are totally soaked, aren’t they, Kendall?”

“Completely,” Kendall said, moving into the frame.

“You know the drill,” Vanessa said, spinning around in her chair to face Kendall.

Turning around Kendall bent over. Reaching back she flipped up her skirt to show everyone that she did indeed still have the toy imbedded in her asshole. Hooking her fingers in her thong she tugged it down as she bent forward and stuck her ass towards the camera.

“Hmm, do you want bonus points, Kendall?” Vanessa asked, getting an idea as she reached out and slipped her index and middle fingers between the base and Kendall’s butt cheeks.

“What do I have to do?” Kendall asked, biting her lower lip as the flared portion of the plug was pulled against her anus.

“Answer first,” Vanessa responded. “Do you want them? If you say yes, it becomes another little challenge with, say, fifty bonus points if you do it. Say no and you can pull up your thong and go home to diddle yourself for a couple hours.”

“Yes,” Kendall said, figuring she could handle anything Vanessa threw at her. Plus, fifty bonus points was a lot and could almost wipe out her strike all by itself.

“That’s what I wanted to hear,” Vanessa said, pushing her thumb against the base of the toy and slowly pulling until Kendall’s anus yielded and allowed the plug to be removed. “Now, clean up your new toy.”

As Vanessa shoved the filthy thing into her face Kendall was shocked. The toy had just spent the last four hours wiggling around in her ass picking up who knows what. There was no way she was going to do it. Except she’d already committed to it and if she didn’t it would be her second strike already.

Taking the butt plug from Vanessa, Kendall brought it up to her face. She could smell it and it wasn’t pretty, but she couldn’t let it stop her. Closing her eyes and breathing through her mouth she spread her lips and inserted the tip of the toy into her mouth.

“So far so good,” Vanessa said, more than a little surprised that Kendall was doing it.

Trying to ignore any foul tastes Kendall pushed more of the plug into her mouth. While she was busy being disgusted though Kendall was surprised to discover her body reacting to what she was doing. It was just nasty and depraved and as her lips stretched to accommodate the flared portion she started to really get into it.

“How does it feel to be so fucking nasty?” Vanessa asked, as if reading Kendall’s thoughts.

“So ‘ot,” Kendall said around the bulbous portion, acting almost like a ball gag.

The toy wasn’t much more than a few inches long so Kendall was able to fit the whole thing in her mouth. As her lips settled into the notch between the base and the main portion of the toy she could feel the tip of the plug just bumping against the back of her mouth.

“Make sure to get it nice and clean,” Vanessa said, using her finger to motion for Kendall to spin the toy around in her mouth.

Treating the butt plug a bit like a lollipop or a popsicle, Kendall pulled it in and out of her mouth, turning it as she went. Her tongue stroked the smooth material of the toy as it cleaned every inch of it.

“That’s probably good enough,” Vanessa said, tempted to call in one of her helpers to test whether Kendall’s blow job technique was as good on the real thing as she was exhibiting at the moment.

“God I’m horny,” Kendall said, smacking her lips after her little ass-to-mouth experience.

“Then you’re in luck,” Vanessa said, clapping her hands and several men appeared in the doorway just as the video feed faded out.

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