Ashley's Last Pizza Delivery

"Open it, try to make it open up," Bernard told Ashley, hand on the back of her head.

She looked up at him, then nodded. Facing forward again, Ashley looked up at Brandon. She squeezed her ass cheeks firmly, her fingers digging in, and for the first time in her life, she actively tried to make her asshole open.

"Is he going to cum in my ass?" Ashley asked Bernard but said to Brandon.

Brandon was again beading sweat on his forehead as he held his cock. As Bernard instructed, he tilted his plum-shaped head down and put his tip next to her asshole. He looked into Ashley's wrinkled dark knot. It began to gape slightly.

"Just relax... breathe..." Bernard coached, holding Ashley's head.

"Mmmmmph," Ashley sighed. She focused on the strange sensation of easing her clenched asshole.

Brandon watched her pink hole open and gape. It seemed like a welcoming gesture. His cock bucked and spat a long wad.

"Gah!" Brandon cried.

He was not known for his aim. The surging action of his curved shaft sent powerful blast arcing over Ashley's body. The cum streak landed in a hanging thick string from the back of her left thigh, over her left breast, and onto her left cheek.

"mmm oh fuck," Ash said flatly. She bit her lip.

"Relax, just relax," Bernard told Ashley.

"C'mon, Burley, up her asshole!" Simon offered encouragingly.

If not good for aim, Brandon was good for volume. He shifted his hips back and saw Ashley's knot open slightly wider.

"Gah!" he grunted, pressing his tapered knob against Ashley's slightly dilated hole.

The creamy burst hit the hole and mostly slipped inside.

"oh," Ashley replied as the hot wet stream piped up her ass. She sighed and Brandon pressed his head harder. He spurted again.

"GUUH!"

"OOH!" Ashley chirped, wide-eyed as Brandon directed a warm rocket straight up her rectum. She gripped her butt cheeks tighter and inhaled.

The surprise inhalation made her asshole dilate just slightly wider. With the cummy lube and Brandon's pressure, the narrow tip of his head sunk in.

"GAAAGH!" Brandon grunted, thrusting. With his head partially inside the teen's tight asshole, the entire sticky wad sprayed directly up her ass.

"HOOOH Oh Wow..." Ashley marveled. She'd never had anyone fuck her ass, let alone cum back there. "Oh fuck." The sensation of thick hot spunk flooding her asshole was new. She'd only pushed stuff out from there. "Fuck... Mmmmm..."

"Breath, Ashley, breath," Bernard said, watching her forehead scrunch.

"He's putting it in... nnnggh... in my asssss..." she sighed, watching her determined teen classmate apply steady pressure. She blinked steadily as his cock was disappearing between her butt cheeks below her pussy. "Fuck..."

With cum spread over the hole, her rim was slick enough that it opened for Brandon's head. Due to the long plum shape of his knob, it took tenacity, but the first inch sunk in, then the second, then his bulb slipped in completely.

"...nnnnggghhOHFUCK!!" Ashley chirped.

Brandon unloaded fully, his cock reaching the intended target. It felt like someone had put a soft hot condom around his cock head that was ten sizes too small. He wasn't going to penetrate her further, but he could finish unloading with abandon.

"NNGuuh...uuunnggh...nnnggghhh..." he sighed, watching his banana-curved shaft as it bucked, spanning between his groin and Ashley's tight rectum. Cum wads pumped through it steadily. His head was throbbing inside her with each deposit. Her glistening lips were swollen and hungry, separated by a thin barrier from where Brandon was dumping his load. He moved a hand back to her mound and flicked her clit with his thumb as he finished.

Ashley panted, grunting with each abundant spurt as it splattered her rectum. She wasn't sure what the state of her asshole was as Brandon filled it with cum, but her pussy was an absolute mess. She was staring at it as he started thumbing her clit.

"Oh-shit-oh-shit-OH-FUCK!" Ashley cried, flinching in pleasure. She came again. This would be her very first orgasm with a dick in her ass.

The boys congratulated Brandon and he felt like a sports star that just scored a goal. He massaged Ashley's hard thick nub through her climax, then reluctantly dislodged his long tapered head from her gripping butthole.

"Hah, fuck..." he said, inspecting the teen cheerleader's now devirginized asshole. "It's still very tight, but she's holding most of it in," Brandon reported.

"Ok boys, lets get her up on the table on her hands and knees. We need to move quickly before the cum oozes out," Bernard commanded.

Ashley was still dazed from her third or fourth orgasm. She was starting to lose track as Simon and Zack helped her turn over and get onto all fours. The young brunette teen was positioned on top of the large gaming table, wearing her long smooth hair in two pigtails on either side of her head. She had her superhero logo t-shirt bunched above her huge, dangling tits, which were now splotchy red. They swung low below her heavily, topped by her wide ever-hard nipples. She knelt on the table with her knees spread about hips width and was naked save for the tiny, bunched-up top and her sneakers.

As the group watched, Ashley reached back and squeezed her ass cheeks. She shuddered slightly as the first alabaster cum runner stretched from her tight hole in a thin line. It dribbled over her pussy lips, then down to the table, dripping between her knees. She smiled back at them as a thin line of spunk drizzled out of her like pancake syrup.

She was a sight for sore eyes as the horny teen Dungeon's and Dragon's group attacked the busty young cheerleader/pizza delivery girl/burgeoning cum slut.

Simon was the most athletic and was the first to get in position behind Ashley.

"Aw man," Zack said disappointedly, just a step behind.

"We'll all have our turn," Bernard said coolly, stroking himself and standing to Ashley's right as he reached down to fondle her hanging funbag.

As Simon stepped up behind Ashley, he was tall enough that he wouldn't need to climb up on the table. He could mount her standing. Her fat cheeks loomed even larger as Simon placed his thick dark shaft between her porcelain cheeks. Then he palmed her broad soft buns and pushed them together. They encompassed his shaft, leaving only his throbbing, leaking head visible.

He could feel Ashley's hot, soaked, inviting pussy lips kiss his balls.

Simon Slater was not the biggest guy on the football team or the most popular, but he was a starting linebacker and had enjoyed many blowjob sessions with the cheerleaders. He was large for his age, but had surprising agility for his size. Somehow he had developed a reputation as a nerd among the popular crowd and as a dumb jock among the more academically-oriented circles. As such, he hadn't had as much success with sex as he had liked. He'd never fucked a cheerleader.

There was actually a point of contention between the guys on the football team and the girls on the cheerleading squad. Their coach, Betty Faux, strongly encouraged the girls to give regular and advanced-technique blowjobs. This was a service provided mostly to the boys on the team, but occasionally served the cheerleading squad in other ways.

But Coach Faux was very strict. The girls were not to have sex with the guys. Blowjobs were given eagerly and freely but the squad was not permitted to develop a reputation for being sluts. Do not fuck. There were some exceptions of course. Some of the players dated cheerleaders and well, teens will be horny teens, but for the most part, the football team never got to fuck the cheerleaders.

Ashley was aware of this restriction and considered it applicable only in the context of sports. This was extracurricular. Being a transfer student, she came from a rival high school cheerleading squad where the rules weren't as tight. She was no virgin, at least not vaginally.

'Well, not anally now, either,' she realized as the guys crowded around her.

Simon didn't know or care about her position on Coach Faux fuck-ban. He drew his raging hard cock down Ashley's butt cleavage and placed his flared head on her soaked cunt lips. It felt like warm butter.

"Wait until the other guys hear about this," he said, smiling broadly and staring down at Ashley's broad ass cheeks. His head was parting her lips, just below her tight, cum leaking asshole. "Victor is going to shit himself," Simon said, referring to the star quarterback on the team.

'Even Victor hadn't fucked Ashley,' Simon thought, happily slapping Ashley's right cheek.

The brunette girl winced as the blow landed.

"Fuck!" She looked over her shoulder as she felt Simon's head push into her needy cunt. Her eyelashes fluttered. "Fuuuuhhhhcccccck..." she sighed as he drove in balls-deep in one thrust.

"HOOoooooh shit," Simon howled as his raging erection was snugly enveloped. He couldn't help himself and immediately drew back and slammed in again. Her big bare butt clapped against his hips.

"FUUHCK!" Ashley whined.

"AAAANGH!" Simon grunted. He slapped her butt again.

Simon liked to start slow, but he was unable to control himself. He felt an animal compulsion to fuck this hot brunette teen with all his might. He suddenly grabbed her shoulders and began slamming back and forth into her pussy. The steady clap of her bouncing, rippling ass cheeks filled the room.

"Anngh, AAAARGH... FUUUUCK!" Ashley did her best to brace herself on all fours as the large linebacker gripped her and began jackhammering her young cunt. Brandon's cum was oozing out of her tingling asshole and running down Simon's churning shaft. As she leaked cum from her ass, Simon was essentially fucking Brandon's cum back into her. And adding his own abundant precum.

Simon breathed steadily, a practiced athletic technique, holding Ashley's shoulders and giving to her fully. Their bodies clapped in rhythm. Her huge hanging tits began adding a softer fleshy sound as they swung below her dramatically, sometimes clapping together also.

Brandon was watching, eagerly recovering for his next opening and stroking himself. Zack was on Ashley's left, rubbing his long, hard, pale cock against her swinging left breast. His arrowhead-shaped tip compressed her supple flesh. Bernard was still to Ashley's right, occasionally squeezing her right boob, but mostly focused on directing the action. His big black cock had been rock hard the whole time and was now shining from Ashley's previous oral attention and his own foamy precum. Bernard nodded to Zack and he slid over in front of Ashley.

"Fuck yeah," he said happily, taking one of Ashley's pigtails in his right hand. This got her attention and she turned to him and placed her swirling tongue on his tapered dick head. Then she stuffed it into her mouth.

"Fuck yeah!" Zack cheered as she slurped down his long stiff cock.

Ashley blinked, tasting Zack's tangy precum and taking his long cock into her mouth. It was raging hard and throbbed steadily sliding through her lips and against her tongue. After being throat-fucked by Bernard's monster, she took Zack's cock straight down her throat in one thrust. It nestled into her snug throat with a wet squishing sound.

Suddenly, for the second time that night, she found her body being ping-ponged back and forth between two of her classmates, impaled by cock from either side. Her voice rose over the clapping sounds of her flesh as she moaned on the dick thrusting back and forth in her mouth. Simon and Zack were occasionally grunting as they used Ashley's holes.

And although she couldn't say as much with her mouth full, it sounded like she was coming again.

"GGGGGGGGGGGGHHHHHCCCCCKKKK!" Ashley gurgled, her body lurching. Neither thrusting cock slowed.

"All your planning has really paid off," Brandon said, moving into Zack's place on Ashley's left. He reached down and guided Ashley's hand to his thick banana cock. She began stroking him, moving like a drone in her climaxing state.

"I guess we'll find out, won't we," Bernard replied, still on Ashley's right. He took her hand by the wrist and brought it to his bloated black shaft. She squeezed it and automatically began pumping.

Ashley was bobbing on Zack's cock and he had a ponytails in either hand. She was jerking off Bernard and Brandon while Simon fucked her doggystyle with zeal. He was almost savage with his fervent powerful thrusts.

"Ungh, whew... uh, whew... ugh, whew..." He grunted and breathed steadily as if doing reps in weight lifting.

"That's it, Simon, stretch her pussy out good, but make sure you can also stretch out her asshole. I want her to be nice and loose for the triple before you bust a nut," Bernard coached.

"Hey man, whew... I'm not... Anywhere near... -whew- ... Busting a nut..." Simon ensured him, speaking between breaths.

Zack laughed and yanked his long cock out of Ashley's mouth. It slipped out and wobbled stiffly, dripping with spit.

"OH FUCK!" Ashley grunted, her mouth suddenly vacant.

"No way," Zack said easily, holding his cock as his friend pounded the teen cheerleader. "Slater's about to nut."

"Fuck fuck fuck!" Ashley cried. "OH FUCKKKK MEEEEEEE!"

Simon didn't break his pace, his thrusts clapping Ashley's ass.

"Psssh, you are the one pulling out," he retorted.

Zack looked down and pulled back on Ashley's pigtail, stroking himself. The brunette's scrunched-up, heart-shaped face rotated up to him. She was panting.

"Mmmm, suck my balls," he said, standing on his tip toes to place his balls over her lips.

"AAATTHHAAAHHH," Ashley vocally tongued his sack, then managed to slurp both nuts into her mouth. She moaned and began swirling her tongue around his entire ballsack.

"Fuck," Zack said, looking into her blinking blue eyes and stroking himself over her bobbing face. She kept her lips sealed around the base of his nuts as her body jostled with each of Simon's thrusts. He jerked precum out of his cock and watched her tongue swirl inside her cheeks, around his balls. Her lips were hoovered around the base of his balls. The suctioning sensation drove him wild. "Yessss..." he hissed.

"Hnnng... fuck... whew... nnnnggg..." Simon looked from the brunette's face as she sucked his friends balls to her big ass. "Look at you, she's going to make you nut just by sucking your balls."

Without breaking stroke, Simon let go of one of her shoulders and slapped Ashley's butt.

"Mmmmmmm," she moaned on Zack's balls, sucking them while stroking two cocks and fucking a third. As Simon's blow rang out on her ass, Zack's balls slipped out of her mouth.

-PPPOPPP-

"Ha, Fuck," she said, looking over her shoulder and grimacing. Spit hung from her chin.

"No way, man," Kyle said, turning her face back to him. He put one hand on Ashley's head and held her firmly with the other under her chin. He aimed his cock to her lips and stuffed in balls-deep. He began steadily, fully stroking into her face.

"You are gonna cum before I do. I'll bet you fifty bucks," Zack challenged his friend, face-fucking Ashley fully. His balls swung back and forth against her chin. His thrusts jostled Ashley back into Simon.

"Psssh, make it a hundo and you gotta deal, chump," Simon raised, slapping Ashley's ass again and slamming her against Zack.

"Deal!" Zack cheered.

Ashley moaned steadily, pinned between the two friends fucking her back and forth from opposite ends. Her suppled body was volleyed back and forth as the two boys tried to one-up each other. To her credit, she managed to steadily jerk off Bernard and Brandon.

"I think Simon's done for," Bernard whispered to Brandon. "He's slowing down."

"fuck... oh... huhhh..." Simon was grunting, his pace dropping. His thrusts slowed but what he lost in tempo, he seemed to be building in power.

"Fuck... OH! FUCK!" he stopped completely. His hands moved to Ashley's puffy ass cheeks and he grabbed them hard.

"HA! Dude, your done!" Zack said, still holding Ashley by her chin and the top of her head. He fucked her face steadily, shaft churning back and forth.

"GGGLUCK GGLUCK GGGGLUCK," Ashley's throat clicked.

"Fuck Zack, hold still for a sec," Simon said, clenching. He felt his lurching cock swelling against Ashley's pussy walls.

"No can do amigo, a bet's a bet," Zack said, not breaking pace. His balls slapped steadily against Ashley's spit-coated chin.

"GLUCK GLUCK GGLUCK," Ashley reported steadily. She suddenly noticed that Simon had paused and was gripping her puffy ass cheeks. His strong hands were squeezing her butt with increasing intensity, and she felt his heavy, trembling cock thicken inside her. Her slick pussy was stretched even further.

"shiiiiit..." Simon sighed.

"MMMM...MMMMM!" Ashley moaned, her eyes widening, as in response to Simon's widening shaft. His cock was filling with thick cum wads, ready to expel them into her. Her grip inadvertently tightened on the dicks in her hands.

"Don't forget her asshole," Bernard warned. He felt his cock head flare in her tight grip. He'd already dumped two loads in her today, but that was hours ago. He knew he'd have another thick nutty load for the sexy young cheerleader.

"Fuck, Zack, Oh SHIT OH SHIT," Simon said, his jaws clenching. He felt the pressure in his balls boil over. His throbbing cock surged deep inside Ashley's stretched teen pussy and he pushed as hard as he could into her soft cheeks. Cum spewed out in chunky wild bursts as Simon began to unload.

"GAHFUCKIMCOMING!" he yelled, red-faced.

"MMMMFFFF!" Ashley grunted, feeling her pussy being flooded. She winced at the force of Simon's spunk blasts as he gripped her buttcheeks tightly. She squirmed but was held fast by Simon and by Zack.

"Hah! Hahhh... hah...." Zack said triumphantly, still holding Ashley's head and fucking her face. "Ohhhh shiiiit," he sighed, sounding as if his confidence was deflating.

"FUUUUUCK!" Simon roared, shaking as he began pumping his hips in time with his spitting cock. His shaft convulsed wildly as he blasted cum wads into Ashley's cunt.

"Oooooh shit," Zack said, sounding even more worried.

"Fuck Simon, her asshhole!" Bernard reminded him.

This was a crucial part of the plan. Simon's cock wasn't as big as Bernard's, but it was just about as thick. The idea was for Bernard to have his big dick in Ashley's ass. It was the only one of her holes that Bernard had not dumped a cum-load into yet. But he'd need Simon's thick, shorter dick to stretch Ashley's butthole first.

But now Simon was unloading deep in Ashley's pussy. Her asshole would be practically untouched.

"GLUCK GLUCK GGLUCCCK"

Ashley's throat echoed with a wet report with each of Zack's deep thrusts. It was obvious that Slater had lost the bet by coming first. Zack had actually been ready to cum when he made Ashley suck his balls, but held off to win the bet. Now, he was free to release the pressure in his balls.

"OH!" Zack thrust in fully. "SHIT!" he said sharply.

Bernard, Brandon, and Zack all heard the splattering sound as Zack's cock began coating Ashley's throat with hot soupy jizz.

"SHIT!" Zack grunted. Another audible flood sprayed Ashley's esophagus.

"HNNNNGH!" She grunted, taking it.

"fuuuuuuck..." Simon sighed flatly.

"At least shoot some up her ass, c'mon!" Bernard said harshly to Simon.

"SHIT!" As Zack swore with each burst into Ashley's stomach, she grunted and drew steady breaths through her nose.

She felt Simon pull out of her flooded pussy. Ashley moaned but couldn't look back as her head was held in place. Zack was still spurting down her throat.

"nnnnnghhhh," she sighed evenly.

"Put it in her ass, Simon. I don't care if she's not gaping yet. There should be enough cum to slip inside," Bernard instructed, watching him move his thick head up, to her pink hole. It was still shining with cum filling.