The Madison Cole Project

Dangerous as it was, Madison was too stubborn to back down now. She could suffer a little bit of embarrassment now if it meant winning over all. Besides, she might not necessarily have to tell people how she found out the truth about what happened between Victoria and Shawn, the truth alone should speak for itself. She was coming out of this deal better than Shawn was, making Brandon jealous, getting the real story and only simulating sex with Shawn. Those were terms she could live with.

“Fine,” Madison said resignedly, trying to give him as little satisfaction in her agreeing as possible. She looked around the dark, dirty alley and asked, “how do you want me?”

“Turn around, and bend over,” he ordered, using his hands on her waist to pivot her body to face away from him, and then with a hand on the small of her back, he angled her so that her ass pointed high and out. “Now start recording.”

With one hand on the wall for balance, Madison held out her phone on the other, opening the camera app and switching to the video function. With a brief look over her shoulder, she checked if Shawn was ready. He gave her a short nod, and she pressed the red circular button at the bottom of the screen and it turned to a stop icon, indicting that recording had begun.

“Hi, bro. I’ve been thinking a lot about what you said, you know about seeing the world and expanding my horizons…and especially the part about me fucking other men,” Madison sweetly declared, as if she were introducing a how-to video. “I thought you should know what exactly that looks like…and the kind of man I might be fucking.”

She angled the camera upwards to show Shawn’s face. He lifted his hand to give a tight wave to the camera, then made a very deliberate show of slowly replacing his hand on Madison’s ass. He rubbed the cheek through her dress in a circular motion, stopping to squeeze and jiggle it every few seconds.

Gasping despite herself, Madison turned the camera back onto her red, aroused face. “This could have been you, Bran. I wanted it to be you. But if I can’t have you, well out in the big, bad world this is the type of big, bad person who might be able to…h-hey!”

Shawn had grabbed the hem of her dress and pulled it up over the swell of her round, athletic ass, until it bunched around her waist. Her buttocks prickled, exposed to the cool evening air, only a small black thong running between the globes of her cheeks keeping her pussy hidden from Shawn’s predatory eyes. Madison shot him a look over her shoulder at the unexpected exposure, but the older man just smirked.

“All part of the presentation,” he assured her in a low voice. With a twirl of his finger, he said, “Keep going.”

“I…um, I…” Madison struggled to collect her thoughts as she turned to face the camera again, feeling Shawn’s fingers kneading her cheeks, squeezing and tugging, prying them apart and making the material inbetween pull tight against her mound. “I…I know you might want to look away, but…but I don’t think you will. I remember you told me how you listened in on Zack and Ashley on their date…how you listened and watched them fuck behind your back. You didn’t want to, but you couldn’t stop yourself, you couldn’t look away until you’d seen it all.”

“Oh shit, I never knew your brother was such a cuck,” Shawn laughed as he continued to roughly spread and massage her ass.”

“Shut up!” Madison growled, flinging her head around again. “He is not.”

“Play along,” Shawn hissed, barely above a whisper, punctuating his words by raising his hand and bringing the flat of his palm down hard against the top of her cheek with a loud, ringing smack. She yelped and her skin glowed red, as he continued. “You don’t want him to think this isn’t real, do you?”

“Fine,” Madison relented again, with a click of her tongue, before adding, “But slap me again, and I slap you.”

Shawn simply smiled as Madison turned warily back to the camera. What was the saying? Give a man an inch and he’ll take a mile. This might all be an act, but it seemed that Shawn was determined to have his fun with her either way. But he was right. This video would be useless if Brandon didn’t buy its legitimacy. And if she cut it short, Shawn wouldn’t tell her what she wanted to know. So, she continued filming.

“I want you to watch the whole thing. I want you to watch me,” she panted, her voice sultry and steamy. “You think you want me to be with other men, to get married and have kids but that’s why you need to see exactly what that entails. Because this is what you’re going to be imagining in your head every single time you see me on the arm of another guy. This is-whoa!”

A chilly breeze blew across Madison’s exposed rosebud as Shawn grabbed the sides of her panties and yanked it down around her thighs. He leered down at her gusset as it pulled away from her drooling lower lips, sticky and damp with her obvious, glistening arousal. Madison whipped her head around for a third time, realising that her entire ass and pussy had now been exposed to the shaven headed man standing behind her, a large, noticeable bulge forming in his trousers.

“What the fuck do you think you’re doing?” she demanded whilst trying to keep her voice from rising.

“Gotta make it look authentic,” Shawn insisted, bringing his hands back up to her ass, grazing her pink, tight little asshole with his thumbs as she gripped and pried apart her ass cheeks again. “No one’s gonna believe you got fucked if your thong is still wrapped around your ass.”

“Oh, okay,” Madison said breathily, agreeing with his logic. “Just warn me next time.”

“Hmm, so there’s gonna be a next time?” Shawn asked with a smug grin, one hand sliding lower between her legs.

“That’s…that’s not what I-” A small moan escaped her mouth as Shawn’s fingertips danced over her labia, feeling her wetness clinging to his digits.

“Nice and wet already. I love when a girl is just ready to go,” Shawn said loudly, taking his fingers from her pussy and bringing them to his lips, sucking her honey from the ends. He replaced his hand, feeling her hole gaping slightly now, looking for something to fill it. “Have you been thinking about this all day?”

She wanted to tell him it wasn’t him she was wet for, but she didn’t trust her voice to stay low in this state of arousal. It was Trent who was responsible for getting her riled up, or more accurately the idea of fucking her brother’s rival to make him jealous. The idea of Brandon pulling her away from another man and declaring that he needed to be the only man who could fuck her and then completely ravaging her got her hotter than either of these men.

But Shawn wasn’t entirely wrong. She had been thinking about this all day. Not Shawn, to be exact, but simply getting fucked. Camping out in nature with her brother turned lover, spending their days completely naked and fucking whenever they pleased was like having sex on tap. To suddenly stop, cold turkey, as it had been today, was utter torment. Just thinking about her brother’s cock sliding back inside her had her pussy slick and tingling.

“Wh-what are you doing?” she managed to ask, ripples of pleasure half-winding her as Shawn’s fingers slid along the length of her slit.

“Relax, this isn’t sex,” Shawn told her, sliding his hand back along her pussy until his fingers met her hole. Pushing between her open lips, he pressed his middle and ring fingers into her. His pinky and pointer slid back down, squeezing her labia together, rubbing against her clit. “Just enjoy it. Besides, we wouldn’t want Brandon to get the wrong idea.”

“No, no, nothing’s wrong,” she moaned, bowing her head while Shawn pumped his fingers inside her, her juices leaking out over his hand. “Oh shit, that feels good.”

She told herself that she was playing it up for the camera, to make Brandon jealous but Shawn’s fingers really were generating a lot of pleasure inside her tight, wet box. She lamented that a scumbag like him could be so good with his fingers. There were good men all around the world who lacked basic sexual skills, but of course a jerk like Shawn would know exactly what he was doing, fingering her and teasing her clit and lips simultaneously. It felt like he had a dozen more fingers than he actually had.

Another moan rose from her lungs as Shawn jammed his fingers into her up to his knuckle. The pleasure was so distracting that she didn’t even feel Shawn’s other hand leave her ass or hear as his belt buckle was undone. She missed the lowering of his zip and the rustle of clothing as he pushed his trousers and boxers down to his ankles. It wasn’t until his cock slapped against the middle of her ass that she stopped mid-moan to look around again, realising what he’d done.

“Shaaaaawwwwwn,” she breathed hoarsely as a warning.

“Relax,” he said dismissively, taking his cock in hand and laying it along her spine. She could feel his balls pressed against her anus as the molten warmth of his cockmeat rested upon her back as if he were measuring how deep inside he could go. Beneath, his fingers quickened, penetrating her harder.

“Shaaaaawwwwwn,” she cooed again, the threat waning in favour of pleasure.

“That’s it,” he said, hearing the change in her voice. Leaning back, he created some space between them, enough for his cock fit between their bodies, albeit poking her ass just a little and leaving a small pre-cum spot on her cheek. Curling his fingers up, he rubbed against the rough ridges inside.

“Shaaaaawwwwwn,” she sang, letting loose with her moaning down, Shawn’s fingers on her sensitive parts making it difficult to distinguish between the pleasure pulsing through her body and the man giving it to her.

In one swift movement, he pulled his fingers out of her hole and replaced them with his cock, sliding his hand down his shaft and coating it in her juices as he shoved his head in as far as her fingers. Madison choked mid-moan, feeling the thicker phallus pushing in deeper than what had been there before, feeling his searing heat melting her from the inside, her fluids leaking out over his length. His hands moved back up her waist, their original spot, gripping her tight as he pushed further inside.

“That-that’s you cock. Your-your cock is inside me,” Madison exclaimed the obvious, the sudden penial penetration causing her to drop her phone onto the alleyway ground. She was too consumed with cock to care right now, looking over her shoulder as she took another inch, and dropping all pretence, growled, “you were supposed to pretend to put it in, not actually put it in.”

“You lied,” Shawn pronounced the words deliberately, marking his triumph and vengeance as he sank another inch inside. “So, I lied.”

“You bastard,” Madison grunted breathily, another inch sliding inside. Fuck it felt never ending. Bigger than Brandon for sure. As big as Kurt she guessed, though she’d only ever had him in her hands. But Shawn felt girthier, but again, it was hard to judge with her pussy as the measure as bolts of pleasure shot throughout her body, her walls clamped around his length.

“Don’t be mad, you’re getting what you wanted. A man to make Brandon jealous, that is, if you can bare to tell him,” Shawn chuckled smugly, pulling her hips back against him as he pushed in completely, her ass slapping against his hips as his balls swung against her mound, tapping against her clit. “The best way to ensure your silence isn’t through your embarrassment of pretending to fuck me, or even actually fucking me, but knowing that I fucked you and you actually enjoyed it. You’ll never tell anyone anything I say, because any time you do, you’ll have the memory of you cumming on my cock.”

“F-fuck you,” Madison spat as Shawn began to slide his cock in and out of her properly now.

“You already are, sweetheart,” Shawn taunted, gripping her hips tightly as the slap of flesh on flesh began to fill the alleyway. “Now I believe I said I’d tell you what happened at the apartment? Do you still want to know? Even knowing that you’ll never tell a soul?”

“…yes,” Madison admitted, gasping as every thrust of Shawn’s cock drove her against the wall and knocked the air from her lungs.

He leaned in over her back, grabbing her hair with one hand, the other still clutching at her hip. Pulling her head back he leaned into her ear, his laboured breath warm against her skin. He whispered directly to her, knowing that she could hear.

“I fucked her, just like I’m fucking you,” he revealed. “And now she belongs to me.”

“And you think that’ll happen to me?” Madison scoffed, even as he slammed the whole of his cock inside her without any resistance. “I’ll never be yours. Brandon is-”

“Brandon can have you,” he cut her off, ploughing into her harder and faster now so that her words became a squeal. “I bet you believed that bit about me wanting to stick it to the football players. The only one I wanted to stick it to was you. I never had any problems with them, nor them me. People are just so quick to find excuses, a reason for everything. The only reason here was me fucking you. So, Brandon can have you, once I’ve finished with you, of course.”

Madison could only moan as he fucked her harder and harder, again and again, with repeated depth. Her body sizzled with pleasure and hating herself from enjoying Shawn’s cock driving in and out of her tight, wet hole. Worse still, she could feel it building, folding, coiling up inside of her, even as it spread to every corner of her body. At her centre there was a tightness, a delightful, erotic tension that could fire at any moment.

Shawn drove into her from head to root in one single stroke and that turned out to be the ticket. The moment came and so did Madison, her body erupting like a firework, euphoric electricity shooting off in every direction, her body shuddering to contain it and failing as she screamed bloody ****. A few people walking past cast a glance down the alley and saw the couple fucking and thought nothing of it. Just another drunk couple, too intoxicated to wait until they got home. Madison only wished she was drunk enough to use that as an excuse.

Her pussy walls tightened around Shawn’s length, his whole cock plugging her hole, the tightness putting just enough pressure on his cock to make him cum. She felt him unload inside of her, ropes of cum splashing against her spasming walls. She groaned, hating that she’d let him cum inside her fertile young pussy, but hating more that the feeling of warm cum inside her hole was intensifying her climax. She’d gotten use to the feeling of Brandon erupting inside her and now her pussy no longer discriminated. Cum was cum and it felt good inside no matter who’s cock it came from.

Her orgasm continued for several minutes after which Shawn’s deflating cock slipped from her hole, his load leaking out her gaping slit. She took some time to catch her breath as the lust and pleasure evaporated from her mind. As she began to think clearly again, she wheeled around, preparing to punch the asshole for lying and fucking her like that. But he was gone. Madison stood alone, panties around her knees and Shawn’s cum trickling down her thighs.