If You Wish Upon a Star

Trent bit his lip as his eyes moved from Ashley to Madison and back again. He’d come to the cabin to fuck Madison, but Ashley’s offer was tempting. Both were girls that he’d wished he could fuck, but he never imagined he realistically had any hope of getting either with Brandon around. Now both were throwing themselves at him. Even if Brandon was around the cabin somewhere, this wasn’t an opportunity that he could just turn down. If the threesome wasn’t an option and he had to pick one though…then it had to be Madison.

“Sorry, Ash,” Trent said, causing Madison to grin like the cat that got the cream. “But if you’re single and back on the market then I can have you anytime. But Madison will always be Brandon’s sister. The chance to fuck her is a window that may not open again.”

Ashley’s eyes twitched, as she clenched her fists by her side, resisting the urge to straight up punch the large, black football player for implying that he could have her any time he wanted. But she reminded herself, the goal was to get Trent to fuck her, not to kill him, though both would satisfy the end criteria of him not fucking Madison. Taking a breath, she turned around and stuck her hands into her bottoms.

“If that’s the case, how about I up the ante to something that Brandon never had the pleasure of?" Ashley purred, as she pushed down her pink panties, completely baring her round, white ass to Trent. “And just so we’re clear. This is a limited time offer. Going in 5…”

She held up one hand, open with the fingers and thumb extended to indicate the count of 5 that she was running down. Trent swallowed hard and licked his lips at Ashley’s firm, toned ass, her panties around her thighs casting a dark shadow over her mound between her legs. Fucking Ashley’s ass, he thought, now that would be something else. He looked again at Madison, indecision overwhelming him again.

“4…” Ashley announced, curling in her pinky.

“Well?” he asked, picturing Madison bending over and pulling up her dress, showing and offering the same.

But it wasn’t to be, as Madison took a stand-offish stance and turned up her nose at Ashley.

“3…” The blond cheerleader called out, lowering the ring finger on her open hand.

“If you’d rather fuck her stanky ass, go ahead,” Madison retorted, knowing it was a weak play. It wasn’t that Madison was adverse to anal, but it wasn’t something she was willing to do with anyone other than Brandon, and Ashley knew it, smiling widely as she heard Madison’s response.

“Stanky…hmm, you tell me, Trent, does it look clean to you?” Ashley asked, using one hand to pull a cheek to the side, exposing her tight, little wrinkled rosebud to Trent’s eyes, as she folded in the thumb on her hand. “By the way, time is running out…2…”

“Fuck, that looks hot,” Trent said, leaning in closer to Ashley’s buttocks. “I bet it’s real tight too.”

“Oh, but I’m sure you could stretch it out with that nice black cock you’ve been wanting to fuck me with for all these years. But only. If. You. Pick. Me.” Ashley wiggled her butt as she emphasized the last five words, finishing by lowering her middle finger. “…1…”

“Sorry Madison, I gotta. You win, Ashley, you win,” Trent declared, grabbing her ass and groping a cheek in each of his big, black palms. “I wanna fuck your ass!”

“Ah,” Ashley gasped slightly, surprised by Trent’s sudden, strong hands on her ass, then grinning victoriously at Madison. “Of course you do.”

Madison snarled wordlessly, at a loss for why Ashley had sabotaged her plan. Sure, she and her brother’s ex-boyfriend had been at odds since their break-up, but Ashley had never come after Madison like this. And it couldn’t be the dress thing…surely, making her strip in front of everyone had made them even in that regard. It just didn’t make any sense to her why Ashley would do something like this now…and fucking another man so openly so soon after her break up with Zack…something was fishy with this whole situation, Madison decided.

As she turned to storm from the living room, she got her answer in the form of her brother, standing in the doorway to the kitchen, having been watching the whole scenario unfold. And he was smiling, just as triumphantly as Ashley, and in that moment Madison knew. This hadn’t been Ashley’s plan. It was her brother’s. He had called in every favor he could with his ex-girlfriend to snatch Trent out from her grasp. She swallowed her rage and embarrassment and immediately began formulating a new plan. She couldn’t let him win, or they’d never be together again. Fortunately, her brother seemed to be under the misguided notion that Trent was the only one she could use to make him jealous.

As Madison stomped away, Ashley felt Trent pull her even closer, squeezing and weighing her cheeks in his hands as he rubbed his face over her cheek, like a purring cat. He turned and placed his lips against her rump, gently kissing skin at first, becoming rougher and wetter, leaving a sloppy trail around the curve of her ass, listening to her breathing becoming heavier as he neared her centre. His teeth grazed over her perfect, white, unblemished skin, threatening to leave a mark. While one arm left her ass and snaked around her front, his big dark muscles looking like she was wearing a thick, black anaconda for a belt, her other hand moved between her cheeks.

He loosely sucked his thumb for a few seconds, slathering it in slobber, uncaring if it dripped down into her crevasse, then slid his hand down the middle of her ass. He felt her squirm with lust as his hot fingers floated over her asshole, passing over it as they plunged down between her legs, feeling her gaping puss dripping. She gasped, involuntarily bucking backwards, as his fingers danced over her entrance, his thumb at the same time, sticky and wet nudging at her rosebud. He teased her, tempted her with his whole hand, fingers and thumb both so close to both of her holes but neither entered but tickled her senses rubbing up and down, round and round, and side to side, pulling roughly at the skin, her body flushing and glowing red every time.

“I always knew you had a nice ass,” Trent complimented her as he planted another kiss on her cheek while he rubbed at both her ass and pussy simultaneously. “But that fucking cheerleader outfit didn’t do it justice.”

“Well, the point is to fire up the fans and the players to do their best,” Ashley’s mouth hung low, as she looked down at Trent over her shoulder, her body struggle not to simply succumb to the dual direction of pleasure flooding her body. “Mmhm, it’d be no good if everyone was too distracted by our smoking hot bodies to focus on the game.”

“If your intention was to incentivize, you should have just come to the locker room,” Trent said, standing, half bending, half lifting Ashley so that he could continue rubbing circles around her wet, mushy lips and asshole. “Tell the team that if they win they get to fuck you and I guarantee we’d have the best season of our lives.”

“And I have to do that every game?” Ashley’s eyes fluttered as Trent withdrew his arm from around her waist, bringing his hand to his jeans and briefly rubbing the shape of his cock through the denim. “Sounds less like a cheerleader and more like a team slut; just a hole for you to work out your frustrations off the field.”

“Firstly, you’re more than one hole,” he said, leaning in and kissing her roughly, while below his hand sped up, groping at her two lower holes harder until her pussy began to squelch, and his thumbnail pushed past her rim. She gasped sharp and loud, breaking the kiss. Trent grinned and said, “And, you know, I think that’s all some of the players need. A good clearing out.”

“And-ah-by some of the plah-players do…do you mah-mean yooooou?” Ashley moaned, waves of pleasure assaulting her from Trent’s hand teasing both her pussy and ass simultaneously. She tried to pull away, to catch her breath, to cool down, but Trent’s arm was back around her waist, pulling her closer to him again. This time she felt something solid and hot nudge against her hip.

Looking down she saw Trent’s cock freed and his jeans pushed down to his ankles. She had no idea when he had done that, her building orgasm distracting her from almost everything around her, even the big, black man whipping out his cock. The good news was it wasn’t quite as thick as Zack’s, the only other man who had fucked her ass, so at least she should be able to take it. However, Trent’s dick was big, black and eager to fill her; he wasn’t likely to be half as gentle as Zack had been.

Ashley couldn’t think about that right now. In fact, she could barely think at all with Trent’s thumb in the asshole, tugging at the hole as his fingers stroked forward and back over her swollen, sodden lips. He was unrelenting, sensing the pleasure building inside her and working her over and over until Ashley could feel herself right on the brink. She was teetering right on the edge, swaying on her feet, held up by Trent’s strong arms, the world swirling around her and feeling so fragile, as if a light breeze would push her over the edge and shatter her into a thousand pieces. The breeze turned out to be a gale, as Trent plunged two fingers into her pussy. And, Ashley came.

She felt herself falling backwards, or possibly being guided. Her mind seemed to flutter in and out of consciousness as it swirled with pleasure, her body like a foreign, detached limb she was watching move. She looked down and saw two black legs behind hers, and felt her back resting on upon something warm and strong, but looking over her shoulder, she only saw Trent’s face, grinning. His hand was no longer playing with her pussy or ass, but her body was still shuddering, her voice still moaning breathlessly as the aftershocks of delight bombarded her body.

Straddling his legs, she sat up, peeling herself off his chest and lifted her body above his lap. Below her, his strong, young black cock pointed straight at her puss as if knowing exactly where it should go and needing no help to get there. But Trent did grab her ass again, lowering her down on his pole since Ashley was too much in a blissful daze to really do much of anything. She heard his groan behind her as her warm, wet, velvety walls wrapped around his cockhead and slid down his shaft, Trent completely controlling the pace as he steadily sank his entire length into her.

Or perhaps he was holding her in place and lifting his hips, thrusting and pushing his cock up into her hot, snug tunnel until his engorged head knocked against the entrance to her womb. She was so wrapped up in pleasure she couldn’t quite tell if she was moving or he was. All she knew was that when that fat black cock was inside, her ass pressed right to his thighs, she felt so full, so good she almost came again immediately. The high of the last orgasm lingered in her body, her skin tingling and flushing at the slightest touch, nevermind the hung black cock currently invading her hole.

“That’s what I’m talking about,” Trent cheered behind her, marveling at his cock disappearing into her body like it was a magic trick. “You like that big black cock in your little white pussy?”

“Mmhmmyeahmmmhm,” Ashley half slurred, half moaned, feeling winded every time Trent filled her up, struggling to breathe consistently as he plunged into her harder and faster, his hips beginning to slap noisily against her thighs.

“Just think, all that time you were with Brandon, and you coulda been sitting on this,” Trent teased, pumping her rapidly briefly, and then slowing down again as he re-positioned his hands under her legs and lifted both up, spread. “I gotta tell you, this is some good pussy. The kind men would play to win.”

“You-you,ah,boys and, hah, your-your games,” Ashley panted, leaning back and trying to hold herself up with her arms but found her body too weak right now, instead collapsing back his chest as before, this time with Trent’s cock in her pussy and his hands holding her thighs, keeping her legs high and wide. “Brah-Brandon ussssseeee-used to be the sa-same. Ah-after eh-every win, we’d fuh-FUCK-an-ah-and I fucking swear it w-uh-was never ah-as hot as-ah wuh-when he-he was hah-high offofa guh-game…”

“Yeah, there’s nothing like the adrenaline you feel from taking on another team and putting them down. After all the hard work and effort, when you’re breathless and sore, then you come out triumphant and suddenly you’re full of energy again and it feels like you can conquer the world. I bet that was the best sex you ever had with Brandon,” Trent mused, holding Ashley’s half folded body as he pistoned his cock into her, coating his member from root to tip in her juices. “But a pussy this good deserves more than one cock. Just think, you could have had a whole locker room full of cocks ready to dick you down right.”

“Ah, ah, that’s yoh-your fah-fuck-fantasy, no-not mah-mine,” Ashley mumbled, barely able to speak coherently as Trent began fucking her faster and harder again. Though she couldn’t deny the buzzing in her pussy from imagining the whole football team lining up to get a piece of her.

“No, my fantasy, as of exactly fifteen minutes ago, is to fuck your ass,” Trent told her unequivocally as he held her tighter, wrapping his whole arm around her legs and stomach, parceling her up on top of him as he pummeled her pussy with his whole length in full, quick strokes. “So, I’m gonna fuck you til you cum again, and get my cock all nice and wet, and then I’mma make my dreams come true.”

“Oh, fuck,” she breathed, feeling as if Trent’s words were literally rippling through her body. Hearing the man lay it out like he did, exactly how he planned to use her, was like her body was kicked into another gear, her body surging with electric power, knowing that the cock plugging her pussy would soon be in her ass, just as soon as she came.

She hadn’t expected to enjoy herself this much, expecting to still be thinking too much about Zack to truly appreciate Trent and his big, black cock. But being with Trent wasn’t like being with anyone else. In most of her relationships, she was the one in control, tempting and teasing, leading them astray. It was true of Gavin and Brandon, and even Zack to an extent, though with Zack it felt more equal. But they all cared for her, to varying degrees. To them she was hot, and pretty, completely fuckable, but something to be worshiped and desired to be fucked by.

With Trent, he was in control, telling her exactly how she was going to be fucked. He didn’t really care about her well-being, only so much in that he wasn’t outright abusing her, but he was here for the pleasure he could get from her body, and by George was he going to get it. The closest she’d come to feeling this powerless to a cock was sneaking in and fucking Kurt in the dark almost a week ago, or when, slightly intoxicated and buzzing from a game of Strip Never Have I Ever, Gavin had fucked a dozen orgasms out of her body over the coffee table. They certainly weren’t the type of men she’d ever marry, or even date, but, shit, could they make her cum.

And cum she did for the second time that afternoon, her pussy pulsing and clenching rapidly around Trent’s cock, leaking so much fluid over his cock that Ashley felt dehydrated. He pumped her a few times, prolonging and intensifying her climax, and making sure that her juices flowed over every inch of his dick, until he could even feel it drip from his ballsack. She moaned, almost screaming as she felt her body being drained, until her throat felt hoarse, and she could only whimper as, finally, Trent’s thrusts began to slow. He pulled his cock from her hole with a sloppy slurp, and gently lowered her legs.

Without support, her petite frame wobbled, still twitching from tiny bursts of pleasure coursing throughout her body, and slumped to the side, her legs curling up. She rolled onto her back, into the groove of the cushion as Trent got up, her body lying open and supine and feeling entirely too warm. She strained to lift her head as Trent approached again, kneeling on the sofa with one leg sliding in behind her thigh and the back cushion, while his other leg remained extended to the floor. Without protest, she allowed him to grab her legs and push them back, practically folding Ashley in two and hooking the knees under her arms.

Her body formed a sort of crooked ‘C’ shape, her head at one end looking down, her pussy and ass completely exposed on the other. With the legs pushed completely back, a feat made easier by her cheerleading practice, her hips were completely parted, her asshole completely displayed to the black teen looming over her. In the light, it glistened from where her juices had trickled down over her buttocks from when she’d came only moments ago. With two strong hands on her thighs, Trent shuffled in closer, bringing his big, black cock closer to her hole, it too shimmering with Ashley’s personal lubrication.

Looking down at the long, thick cock as it neared her ass, it was easy to forget that it wasn’t as thick as Zack’s, that she’d had bigger cocks in her butt. All she could see was the blackness of the cock before her and her puckered, little pink rosebud, the two seemingly incompatible. She swallowed hard as his wide cockhead pushed against her. Her ass resisted, but she could feel the skin around her hole beginning to stretch, about to give way. But his member bent, and Trent winced, pulling back instinctively. She watched him come at her again, this time holding his cock in one hand, keeping it steady as he pressed the head to her wrinkled anus.

The skin stretched, just like last time, discomfort and slight pain sobering her from her lust and orgasms as he held his cock to her asshole, pressing gentle but steady. Then, just as Ashley thought it would never go in, her ass opened and swallowed his helmet in one quick gulp. She threw back her head and groaned before looking down again, mesmerized by the sight of her own ass bulging with Trent’s cock. And that was just the tip. Taking a moment to breathe with the tight rim of her anus around his sensitive head, he released the shaft and placed his hand back on her thigh, more for grip and leverage since her legs were securely fixed behind her arms.

“Fuuuuck,” Trent growled, beginning to push more of his cock into her ass, pushing forward and gaining little ground, but pulling back even less for fear her snug hole would simply push him right out again. “This is even tighter than I expected.”

“Wha-what did you expect?” Ashley gasped, watching another inch of his black cock disappear into her white hole, her pussy lips twitching hungrily as her ass was filled. “You’re only the sec-second guy to ever fuck my butt.”

“Pity I couldn’t have been the first, but if this is you loosened up, I can’t imagine what it was like for him,” Trent mused, bringing a hand down to her pussy and rubbing her clit, her sudden burst of pleasure causing her ass to swallow even more of his cock. “Guess I’ll just have to make this memorable for other reasons.”

There was no way she’d forget the time one of Brandon’s teammates fucked her ass in Heather’s family cabin because her ex-boyfriend had asked to in order to prevent his twin sister from fucking him, but she couldn’t tell Trent that. Instead, she lay, curled up like a pretzel, with the broad, black teen, rubbing her clit and fucking her ass, making her moan and sigh as inch after inch of his cock slid inside, feeling longer than anything had ever felt in her life, until eventually, finally, he bottomed out, his heavy balls pressed right against her curved tailbone.

Not that Ashley had any time to congratulate herself for taking all of his cock, as he immediately began to withdraw, until he felt her begin to stretch around his glans, and slid all the way back in again. He went slow, at first, opening up her ass to fully accept every inch of his throbbing, veiny black dick. As he felt every subsequent thrust becoming easier, he began to pick up the pace, pulling his cock out faster, and shoving it in harder, their bodies slapping and clapping, like a beat to the rhythm of Ashley’s ass fucking.

His hand remained on her clit the whole time, his thumb rubbing back and forth over the sensitive nub in time with his cock being buried in her hole. She could feel that same, familiar sensation swirling in her core and could feel a third orgasm approaching in her very bones. And she could tell by the way Trent grit his teeth and panted that he was close too. Maybe it was just the tightness of her ass still, but sometimes a girl just knows, and she could tell that Trent was almost ready to burst. Though it wasn’t surprising, not many men could have touched her and fucked her and held out this long without coming. No wonder Tanya and Amber raved about him.

“Ever had someone cum in your ass?” Trent brusquely asked, his not so polite way of telling her he was close.

“N-no,” Ashley moaned simply, her own body pulsing with every thrust of his naked cock into her ass.

The one time that Zack had fucked her ass, Brandon had been in the room, blindfolded, and when he was ready, he pulled out and came over her tits. It was strange to realize she’d been quieter in that room with Zack’s cock in her ass than she had been today, loudly getting fucked in the public living area, and yet no one had come to see what was up. If she wasn’t about to take Trent’s cum right up her asshole, she might have been more curious about that. Instead she focused on her own orgasm, rumbling just beneath the surface, approaching like a train and erupting with what felt like volcanic ****.

She released her legs as her back arched, though they didn’t go far, held in place by Trent’s hands and arms, pushing her ass up against his cock, burying him deeper than ever in her rectum, feeling his mushroomed head stretching out new depths. Her pussy twitched, her inner walls convulsing, her ass mimicking the action around Trent’s cock. He’d held off as long as he could, but Ashley’s ass squeezing his shaft like a firm, strong, warm hand was the last straw. He shuddered and swore and spurt forth his cum painting the insides of her ass so deep he imagined she’d be shitting out his seed for days to come.

They continued, softly grinding against each other, working through their own orgasms and slowly easing Trent’s cock from her ass, until their climaxes subsided and Trent’s softening member slipped from Ashley’s ass with an audible pop. He fell back, taking deep breaths and wiping the sweat from his brow, while her legs finally fell flat, stiff and sore from being held high for so long. Gingerly, she rolled over, prone upon the couch, her ass still tingling from the thorough assfucking. Looking at her now, with her ass pushed up, her hole gaping and winking as a trickle of his cum leaked out, he knew it had been a job well done.

It was also tempting him to fuck her again, maybe this time doggy-style. There were so many great views of this girl taking his cock that he hadn’t seen. He was spent, from having just cum, but if he had a minute to cool down, perhaps clean up and splash some water in his face, maybe he’d be ready for round two. Excitedly, he jumped up.

“Where’s the john in this place?” He asked, gathering up his jeans and looking down the two hallways.

“There’s a bathroom down there,” Ashley lazily pointed, without looking up, half speaking into the cushion.

Hearing him dash off, Ashley absently wondered if he was off to find Madison, perhaps hoping to still get what he wanted from her. If she wasn’t wiped out, she would have stopped him, but she, and her ass, needed to rest for a minute. Besides, as far as she was concerned, she’d upheld her end of the deal. She’d fucked Trent, and Madison hadn’t. Whatever happened next was up to Brandon to stop.