Aye, There's the Rub

Ass or Pussy.

Chloe bent over in the backseat of Zack’s sedan, hands spreading her buttocks, offering up both holes for Gavin’s consideration and delight. He felt his cock, slick with Chloe’s slobber and sticky with his own cum, stiffen further, as if trying to stretch from his body to hers. It was as hard as iron, a solid piece of length only becoming more engorged as he tried to decide between sticking his dick in her ass or sliding it into her pussy. She swayed her hips from side to side, like a metronome, tempting him to pick a hole to fuck, biting her lip and giggling as Gavin paused, half in the car, half out, trying to make the choice between her ass or her pussy.

If that wasn’t the age-old question that had plagued mankind since the dawn of time, then Gavin didn’t know what was. It was also an impossible choice. He was being asked to pick between one tight, wet hole, and another, tighter, hotter hole, and even having experienced both, he still couldn’t decide which was sweeter. Maybe with more time, he might have thought about it, but he’d just assumed he’d be fucking her pussy in the back of the car. Having the option suddenly thrust upon him had caused his own body to grind to a halt.

Still, he had to think fast. They were in a parked car outside a night club and eventually their friends would come back. Ass or Pussy. It was tough to pass up Chloe’s juicy pussy, especially how dripping wet it was right now, but it was even tougher to ignore that wide, curvaceous ass, and the winking little rosebud between her cheeks. What made it even hotter was just how much Chloe enjoyed taking a dick in her ass. He’d been surprised to find that she took such delight in being fucked in the butt. Yet, it really did heighten the experience for him to know that when he was fucking a girl that she genuinely enjoyed being fucked.

“Oh fuck, uh…” Gavin continued to debate with himself as he found new strength in his legs, crawling into the backseat behind her. “Um…ass!”

Chloe squealed as Gavin dove head first between her cheeks, covering her pink rosebud with his mouth, his nose wedged against her tailbone. He licked all around the rim with the flat of his tongue, causing Chloe to moan lustfully. She gripped the cushions for support and squinted her eyes shut, half drooling on the passenger seat while her mouth gaped open, gasping as she made her pleasure audible. Her other hand remained on her ass, holding her cheeks open for Gavin’s mouth. She looked back, a pair of glasses sitting atop a mop of dark hair so tight against her buttocks that she couldn’t even see his face.

She felt his tongue move from the edge of her hole to the centre and apply just enough pressure that her willing, wanting ass began to open for him. He rolled his tongue and made it thin, shoving it inside her as deep as a thick finger. He pulled back, sliding his tongue out again, his lips separating from her hole with a wet pop. Her asshole gaped slightly at him before he moved back in, stabbing his tongue back inside her ass and swirling it all around to lubricate and widen her hole.

Beneath her ass, as he continued to work her with his tongue, he moved his hand down between her legs, cupping her dripping puss. He dragged his hand backwards, gathering a handful of her liquid desire in his palm and brought it to his cock. Though it was still slick with her saliva, he stroked himself while he tongued her ass, coating his length in her natural lubrication. When he felt he’d adequately prepared his cock, he moved his hand back to her pussy, gathering up another cup of her juices. His mouth left her ass with another sucking pop but the sensation of his tongue was quickly replaced with his hand, smearing her ass, inside and out, with her wetness.

Once he’d soaked her ass and his cock with her womanly fluids, he straightened up, though still hunched to avoid hitting his head on the roof, and shuffled in close behind her, until the head of his cock nudged against her pussy. He took his dick in hand, holding the shaft firmly, and angled it upwards towards her ass. He leaned forward, placing a hand on Chloe’s back for balance. She realised what he was doing and lowered herself back against him, the dual motions making them meet much faster. His bulbous mushroomed tip pushed against her wrinkled hole, Chloe hands still holding open her ass to allow his cock a direct path.

He felt some initial resistance, but her ass quickly opened and swallowed his head whole. By this point, Chloe had been taking a dick in her ass, or a dick shaped object at least, almost every single day. Some days twice a day. Her ass was still just as tight as it was before she’d come but she found herself able to adapt and accommodate the thick length sliding in past her anus much more easily now. As such, it only took Gavin a couple of thrusts before he was completely, balls deep inside Chloe’s rectum, her insides wrapped snug around his hot, hard cock.

“Ooooooh, fuck, yeeeessss,” she cried out, delighted to have her ass filled once again. “Mmhm, your dick feels sooooo goooood in my ass.”

“Shit, Chloe, you ass feels so good on my dick,” Gavin retorted, gritting his teeth as he felt her ass squeeze around his twitching dick. “I gotta start fucking you before I lose my mind.”

“Yeesss, go on, fuck me, fuck my ass,” Chloe encouraged him gleefully. “You picked my ass to fuck, so do it, fuck it good.”

Gavin didn’t need any more prompting, not that he need any to begin with, but satisfied Chloe was ready to begin the main event, he grabbed her waist with both hands and started to move his hips. He pulled back until his head was peaking out, her anal ring just about to stretch open to allow the fat head to pop out, and then he thrust back, filling her ass with the whole length of his cock again, nice and slow, letting her experience every inch of molten meat, every ridge and vein as it pushed inside. She groaned, low and animalistic, almost demonic, as the slow insertion made her tense and ****.

Gradually, Gavin increased his speed. With each repetition of withdrawing his length and sliding it back inside, he shoved his cock back in just a little faster, pushed in deep just a little quicker, held it there shorter, pulled out sooner. His hips began to meet her ass with ****. At first it was a small clap, barely heard over the sound of air being pushed out of her ass by his dick or her cute little pants or his own laboured grunts. Those too became louder. The clapping of flesh on flesh became a smack and then a thunderous thump as he railed her ass with the full length of his cock.

“That’s it, fuck my ass, fuck it hard,” Chloe moaned, pushing her ass back against Gavin’s thrust. “Shove it deep inside, hmmm, fuck, soooo goooood.”

“Ah, shit, your ass is the best Chloe,” Gavin replied, closing his eyes as he pistoned in and out of her ass rapidly. “I can’t believe it feel this good already. I only just came in your mouth and it feels like I could cum again any minute inside your ass. It feels amazing.”

“Mmmhm, yeah, cum if you wanna cum,” Chloe permitted, feeling the heat rising in her body as she imagined his sticky, warm load coating her rectum. “Oooooooh, I can’t wait.”

“You sure?” Gavin asked, fucking her still but holding back as tempting as it was to simply cream her asshole. “What about you?”

“If you cum in my ass, mmmmm, I’ll probably cum tooooo,” Chloe admitted, and then glancing down to the floor behind the passenger seat, she smiled. “But I might have something that could help with that.”

Gavin looked at her confused, as she turned her head away and reached down to her bag that sat before the backseat. She rummaged around for a moment, Gavin’s dick still firmly wedged in her ass, her asshole wrapped around his shaft, buttocks bucking back against his bewildered, slowing thrusts.

“Don’t-don’t stop,” she insisted lustfully as she pulled something from her bag and slid her hands below her body. “K-keep going, faster, hmmm, yeah, harder.”

Gavin focused and resumed his previous pace, at least for a moment, flinching when he felt something thick and rubbery prod against his balls. He tried to look between her legs, but he couldn’t see. Looking back up at Chloe, he asked, “What is that?”

“Just a little present from Hanna-aaaaaaaah,” she sang as she found her pussy hole with the strapless strap on, gripping it by the bulb and pushing the length into her hole. Her soaked hole happily accepted it, covering it with her juices as she pushed the whole thing inside.

Her best friend gasped as he felt the fake cock rub against his very real cock through the thin, fleshy veil between her pussy and her ass. Chloe could feel the cocks pressing against each other, with her wall caught in the middle, and she held the strap on there, rubbing back and forth slightly, caressing Gavin’s cock as much as herself. She slid it inside herself, faster, harder, her pussy sucking wetly on the cock every time she pushed it in. Gavin moved to match her, faster, harder, rhythmically pumping her ass full of his cock in time with her.

“Oh, fuck, that might actually just make me cum faster too,” he warned her, his cock growing sensitive as it was rubbed by Chloe’s strap on through her pussy walls, and feeling his balls bouncing off her hands.

Chloe simply grinned, as she reach down, behind the fake balls of the fake cock, and said, “If you like that, you’ll love this.”

And then she turned on the vibration.

Instantly, she screamed into the shoulder of the passenger seat, the shaking and shuddering of the strap on causing great ripples of pleasure throughout her insides. She felt Gavin grip her hips tighter, holding himself balls deep inside her ass, groaning as he too felt those same ripples rolling up and down the length of his shaft.

“Ooooh, oh, holy shit, it feels like your whole ass is vibrating around my cock,” he sang, amazed, moments before the sensation intensified and he felt a familiar shooting feeling along the length of his cock. “Ah, I can’t take any fucking more, I’m cumming.”

As he said the words his slit opened, and his cock spewed forth cum deep into her ass. She could feel it hot and viscous in the furthest reaches of her ass. Rope after rope fired from his tip, unloading inside her until she felt clogged with cum and cock. He was still cumming when she, true to her word, climaxed, when the felt his seed seeping into the walls of her rectum. Her pussy flushed with fluids, at first gushing out around the cock and then pushing it out completely. She squirted, completely unhindered, spraying the backseat of Zack’s car, her cum drenching the cushion.

They came, and came, and kept cumming, until both were drained and spent. Gavin slumped back, his softening cock slipping from her asshole with a small pop. Chloe rolled onto her side bringing her legs together, and curling up on the backseat. The pair rested, catching their breath, as Gavin’s eyes feel upon the, still vibrating strapless strapon, the realistic design making it seem like a real cock laying at Chloe’s feet. At least until it came to the root, where it turned up into what looked like a thick spherical handle, thicker than the rest of the cock. He was shaken from his thoughts as Chloe reached out and took it in her hands, turning off the vibration, the smile on her face telling him that she’d caught him looking.

“It’s a strapless strap-on. This part here…” she said, tapping the bulbous sphere. “goes in here.”

She shuffled around to face Gavin, sitting on her knees, her legs parted as she reached down between her legs with the cock. She found her pussy with the bulb and slid it inside, her wetness allowing it to easily fill and stretch her. It was keeping it inside that required concentration when she was this wet and aroused. She looked up at Gavin’s face, an expression of bewildered, conflicted desire painted upon it. She could tell that he was struggling, just as she once did, with how hot and erotic the sight of herself, full tits and round ass with a thick cock jutting from between her legs, looked.

“It’s hot, right?” She encouraged him, patiently waiting and allowing him to tentatively nod before asking, “would you like to help me clean it up?”