Pimpin' Out My Step-Sister

©2025 by the author using the pen name Smuttyandfun. All Rights Reserved.

Just so you know, everyone in this story is over the age of eighteen and more than happy with everything that's going on.

I almost broke out laughing at the shocked look on my friend Cory's face when my gorgeous step-sister Jess rushed to greet him at the door in the same sheer, skimpy outfit she'd been wearing all night. Her big luscious tits on display, clad in just a tiny thong that really showed off her shapely ass and barely covered her pussy.

"Um, hi, Jess," Cory murmured, eyeing her tits as his family eagerly followed behind him into the house. Their eyes popping, as one by one, they got an eyeful of my scantily clad sister.

Once Cory had introduced them, I explained that Jess was hoping to raise some money for her college tuition. While his dad, struggling to keep his eyes on her face, smiled and asked, "And what is it you're selling, young lady?"

Jess grinned and watched their eyes flare when she pointed at herself and shocked them when she told them, "Me."

Before they could say anything else, I jumped in and told them how it worked. "It's a hundred bucks for a blowjob, and two hundred if you'd like to fuck her."

Cory's dad looked a little concerned as he looked her up and down, and asked, "So, you're okay with this um... sex for money business, young lady?"

Slyly grinning, Jess nodded, sauntered over and brushed a hand across his chiseled jaw, gazing up into his big blue eyes. "I'm way more than okay with it. And if you'd tell me what each of you would like, I'd be happy to share myself with all of you."

Giving me the side-eye, Cory leaned in and quietly whispered, "Is this for real?"

"Yep." I nodded and flashed him a grin, feeling surprisingly proud of my sister, now that she'd said she was willing to take on his whole family. While I lowered my voice and explained to Cory, "The folks are away till tomorrow night. So, Jess decided to earn some money for her education while they're gone."

Obviously anticipating a fun-filled night, all five of them got their wallets out and dropped a pile of money on the table. While Jess walked over to Cory, captured his face in her hands, gave him a soft little kiss on the lips and had his eyes rolling back in his head when she pulled his t-shirt over his head and began to undress him.

Smoothing her hands over his firmly muscled chest, Jess ran her fingers through his blond chest hair and smiled. "And what would like to enjoy with me, Cory?"

"Um..." He hesitated, sounding a little uncertain. "I'd be happy to do anything you want me to. Even just being able to touch you would be like a dream come true."

"Then, why don't we get our clothes off," Jess suggested with a naughty smirk as she tugged down Cory's fly and began to stroke his big, thick bulge through his clingy, black boxers.

Sounding a little breathless, Jess glancing from one to the other, licked her lips and winked at his family, as she eagerly eyed the long, thick bulges in their jeans. "And then we can decide who would like to go first, while the rest of you watch, imagining all the things you'd like to do with me once it's your turn."

"How about we spit roast you?" His identical twin brothers said in one breath, chuckling as they elbowed each other, eyeing her luscious tits.

Their father looked confused. "What the hell does that mean?"

Jess laughed and explained. "It means, I'd have one of your big, strong sons pounding my pussy, while the other one slides into my mouth."

His chest heaving, Cory's eyes flared as he imagined his brothers enjoying her like that. "Then how about I take a turn with you, before they get started?" he suggested, letting his eyes slide over her tight little body.

"Sure," Jess agreed, coyly smiling as we all slipped out of our clothes. Nostrils flaring, anxiously sliding their cocks through their fists, they looked on spellbound as Jess stepped out of her thong and cast it aside, along with her sheer pink robe.

She was such a smoke show, I noticed they all sucked in a breath the moment they got their first look at her completely naked. Her big luscious breasts heaving in anticipation, her nipples fully erect, obviously aroused at the prospect of getting it on with five big, burly men, who all seemed blown away at the idea of getting busy with her.

"So, Cory," Jess said with a smile in her voice as she wrapped him in her fist, and began stroking him up and down. "Would you like to slide this bad boy between my lips? Or would you prefer to get off by pushing your way into my pussy?"

Cory's breath seemed to stall as he gazed down at her shaved mound and quietly murmured, "I would really love to get inside you."

Coyly smiling, Jess took him by the hand and led him over to the couch, slid onto her back, and spread her legs, so they could all get a look at her beautifully swollen pussy, that looked like it was just itching to be filled and fucked.

Meeting Cory's gaze, Jess crooked her finger, and flashed him an encouraging smile. "Well then, I think you'd better get down here with that big fat cock, so you can fill me up nice and tight."

Even as I watched him get down on his knees, trembling between her legs as he got off on the feeling of sliding his fingers over her sodden pussy, I kind of felt sorry for Cory. I knew he'd always dreamed of getting it on with my sister, but probably never imagined it would be with his whole family watching, all eagerly waiting for their turn to slide between her legs, or pump their way into her mouth.

Still, I got the feeling that Cory was enjoying himself, especially when Jess tugged down his head, slipped her tongue between his lips and gave him a hot open-mouthed kiss, while guiding his long, thick cock into her pussy.

"Oh, yeah!" Cory murmured, sounding elated once he managed to broach her opening and pop his mushroom cockhead inside her, groaning as he slowly began to pump. "You feel so good," he told her, pulling back and pushing in a little deeper with each thrust. Till they had a nice steady rhythm going, happily smiling into her eyes as he drove his way inside her.

"Hmm, so do you," Jess murmured, stroking a hand over his cheek, while Cory kept flexing his hips and pumping, till he was buried in her balls deep. "You're so thick, I can feel every inch of you pushing your way inside me, stretching me open to take you."

"And you're so tight, you fit me like a nice warm glove," he whispered, dropping a kiss on her lips.

Already shivering, Jess wrapped her legs around his wait, so he could go even deeper, while Cory hissed at the sting of her nails digging into his back, as he picked up his pace and really began to rail her, sweat beading on his brow as he did his best to drive her over the edge. We could see the way they were trembling. Almost there, his breathing ragged, he warned her, "I'm really going to fill you up." Jaw clenched, chest heaving, sweat pouring off his face, he dug his hands into her ass, and straight-up pounded her into the couch.

It had to be the most erotic thing I'd ever seen, watching them fuck like beasts in heat. I could feel my balls growing tight, hoping I wasn't going to lose my load and shoot up his back. Gritting my teeth, I slammed my dick through my fist, imagining it was me pumping my way into her body, fucking her raw. Having experienced that sweet, tight pussy first hand, I knew exactly how good it felt for my friend to be driving his cock into my sister, since I'd had the pleasure of pounding her ass into the bed and filling her up with my seed, just before they got here.

Glancing around at the others, I noticed Cory's family all looked pretty blown away, watching him nearly fuck her blue, the way their cocks were flying their fists lightning fast, while they growled and groaned, dripping gobs of precum all over the gleaming hardwood floor. As each of them imagined how incredible it was going to feel once it was their turn to get off with her.

"Looks like she's really enjoying herself," Cory's dad remarked on a shaky breath, squeezing his thick, veiny cock in his fist as we watched Jess's tits shaking as she went into a full-body shudder, as she got closer and closer to reaching the peak and flying over the edge, climaxing for at least the tenth time tonight.

I truly was in awe of my sister, after watching her give everything she had to all the men she'd been with, knowing that she not only craved it, but genuinely cared. As I realized, her goal wasn't just to get them off. What really thrilled her was seeing how elated they looked as they came, while she selflessly shared herself with each and every one of them.

I could feel my pulse racing through my veins, as I shuddered, sweating up a storm, as I watched her come. She just looked so beautiful the way she shivered, her whole-body blushing into a beautiful shade of pink as she reached the pinnacle, tossed back her head and cried out as an earth-shattering orgasm rippled through her body. Obviously delightedly to feel Cory getting off, she was wearing the most beautiful smile, as she watched him clench his jaw as he kept driving his cock deep his inside her. Even after he'd come, he still kept pumping, desperately growling as the got off on filling her up with another load.

"Oh, baby, that was amazing," Cory muttered, a sheen of sweat covering his body, as he breathlessly captured her face in his hands and kissed her, while still gently thrusting, obviously hating to pull out.

Looking pretty happy, Cory shook his head at me and grinned as he got to his feet, though I noticed his legs were still trembling pretty hard.

No surprise, his twin brothers wasted no time arranging Jess's body the way they wanted her, eager to drive into her from both ends.

"Oh, fuck yeah!" Jack muttered as he slid two fingers into her juicy pussy to give her a little finger-fucking. While his twin brother Joel, tipped up her chin, smiled into her eyes and quietly groaned, as he pushed his long, thick member past her lips and started thrusting.

Her eyes drifting shut, Jess quietly moaned, looking absolutely elated at the feel of Joel, stretching her lips to the max as he slid over her tongue. While she blissfully sucked him into the heat of her mouth, as he let out a deep satisfied growl at the feel of pumping his cock all the way into her throat.

While his brother Jack was working his thumb around her clit, looking pleased at our hard he had her shivering as she cried out and came all over his fingers.

Jaw clenched, sweat beading on his forehead, Jack fisted his cock in his hand. Holding our breath, we watched him line himself up, letting out a savage grunt as he pushed in, and broached her opening. He was so big, we all breathed a collective sigh of relief when he managed to pop his thick, angry red cockhead inside her, without tearing her up. Though we noticed she was shivering pretty hard as Jack bent and dropped a kiss on each of her heaving tits, as he began to flex his hips, driving himself deeper into her quivering body with every thrust. "Fuck, you feel good," he told her, as he took his time, obviously enjoying the feel of her inner muscles clenching tightly around his cock, sucking him in even deeper.

As Jack picked up his pace and began to rail her, we all glanced around at each other and chuckled at the erotic sounds her juiced-up pussy was making as he swiveled his hips and drilled his way inside her. No surprise, she was gushing, after taking so many loads. It was so arousing, the way it was oozing out of her, dripping down to her ass, such a beautiful, erotic eruption of white-hot cum.

"Oh, fuck, that's hot!" their older brother Keith muttered, savagely beating his meat in his fist, while we watched in awe as his brothers got off on pumping their way into both ends of my sister's quivering body. "Once they're done with her, I hope she'll be up for a little sixty-nine. I'd love to feel that sexy mouth wrapped around me while I drive my tongue into that pussy and give her a nice little tongue-fucking."

I noticed their dad looked entranced as he watched one twin clutching her head in his hands, growling as he thrust his way down her throat, while the other gently slapped her ass, chuckling and shaking his head at how good it felt, as the pair of them enjoyed the hell out of sharing my blissed-out sister. Who was blissfully shaking right down to her toes as the big muscular twins got closer and closer to shooting two more loads into quivering body.

"I can hardly wait to come inside that juicy pussy," Cory's father leaned in and confided, his rigid shaft shooting through his fist like a piston, creating a big, sticky puddle on the shiny hardwood floor. "I would love to have her impaled on my cock, riding me when I come."

"I'm sure she'd love that," I told him, as I remembered how insanely hot she looked with her hair wildly floating around her face as she rode me to the finish line, happily bouncing on my joy stick.

"So, you've fucked her?" he asked, looking surprised.

I shrugged, feeling a little embarrassed. "Well... as you can see, she's kind of hard to resist. And she's really just my step-sister, so yeah, we've enjoyed each other a few times." I said, trying to explain why I thought it was okay to not only get naked with my sister, but to enjoy the fun of coming with her, too.

As the rest of us watched the twins sweating up a storm as they got themselves off with my sister, Mr. Burnett nodded that he understood. "Yeah, I could see that. To be honest, I never dreamed I'd ever want to get it on with someone else's daughter. But she's so sexy and so sweet and so giving, I've got to get inside her before my balls explode."

Keith and I chuckled as we watched the three of them toss back their heads and shudder as they all came at once. Jack and Joel gritting their teeth, growling like beasts as they drove their cocks in and out my sister's quivering body, elated at the feeling of pumping two more loads deep inside her.

Jess looked so blown away, blissfully smiling as she wiped a shaky arm across her face to catch the cum slipping from her lips, while she happily spread her legs to let us see her gushing pussy, that looked so incredibly hot, all red and swollen and just oozing with cum.

Keith wiggled his eyebrows, and told his dad, "I guess I'd better get in there and lick that up, so we can finish her off."

Savagely squeezing his cock in his fist, Mr. Burnett, obviously fighting to hold back, gritted his teeth and nodded. While we watched his eldest son press a kiss to her lips, before her parted her thighs and dove in to clean up the seed that was gushing out of her like a river.

"Oh, fuck. I can almost feel her clenching around me." Cory's dad groaned, desperately pounding his meat, looking like he was right on the edge at the sight of his eldest son getting off on eating out my blissed-out sister.

The way he was growling, his face all slicked up, Keith seemed like he couldn't get enough, as he held her open with his thumbs, driving his tongue into her as deep as he could go, hungrily licking up every drop.

Once Keith finally came up for air, and he turned her around, Jess gladly returned the favor and sucked him into the heat of her mouth, rolling his balls in her fingers, while he grunted, nearly devouring her. Till he had her helplessly writhing in his arms and gushing into his mouth as they rode the wave together, shaking and moaning as they reached the peak and sailed over the edge, going into a full-body shudder, rocked to the souls of their feet by what looked liked an insanely powerful orgasm.

Still shaking, Jess had barely caught her breath, when she looked up and smiled up at Cory's dad, and gestured with a crook of her finger for him to step over to the couch for his turn.

Though she looked a little shaky, as Mr. Burnett helped her to her feet, she looked pretty pleased when she realized that he was getting on his back, his big, fat cock standing straight up in the air, intending for her to ride him.

Framing his face in her hands, Jess sank her tongue into his mouth and feverishly kissed him as he took hold of himself and held his cock to her opening, silently inviting her to slide down and impale herself on his rigid shaft.

"Ooh, you're a big one," she cooed as she carefully eased her way down, biting into her lip, till she was fully impaled with him looking utterly elated at the feel of being buried balls deep in the warmth of her body.

"Damn, you feel good," he told her, thrusting up, while Jess pushed down, till they'd worked themselves into a nice steady rhythm, forgetting all about us watching, as they got off on the feel of each other as they mated.

"It's been a long time since I came inside a woman," he told her as he cupped her breasts in his hands and kissed her nipples, making her squirm and shiver as he licked them each in turn, giving them each a little nip of his teeth, while Jess squealed and softly laughed.

"I can't wait to feel you erupting inside me," Jess said, smiling into his eyes as she rode him.

Mr. Burnett flashed her a teasing smile. "I hope you're using birth control, young lady. Because I've always been pretty potent. I got my ex-wife pregnant first time we tried for each of our sons."

"Then maybe you'll be lucky, and you'll put a baby in me," Jess teased, with a little smirk.

Just the thought of it had him rolling his eyes and groaning, as Jess swivelled her hips and took him even deeper, pushing him deep into her body.

As he clenched her ass in his big meaty hands, I could feel my dick pulsating in my fist as we watched him use her weight to fuck his cock, desperate to get himself off, he kept driving into her balls deep, slapping their bodies together. As he locked eyes with her, growling like a beast, we all stared mesmerized as they straight up fucked, undoubtedly spurred on by the idea of pumping her full of his seed, and planting a baby in her womb. "Just the thought of breeding you, has got balls aching. Fuck, I'm coming so damn hard, I just hope you can handle another load, baby girl, because this is going to be a gusher."

Jess let out a startled gasp when he drew her left tit into his mouth and started sucking really hard, their bodies frantically slapping together, the tension mounting as they began to crest. "Ooh, I'm coming so hard!" Jess cried out, digging her nails into his shoulders, while he kept thrusting up fast and hard. Jess couldn't stop shaking, as he nibbled on her nipples, tugging them with his teeth till he had her squealing her head off, and collapsing on his chest, quivering as she gushed all over his balls, coming harder than I'd ever seen her come.

Obviously not quite done with her, we watched amazed, when he flipped her onto her back, spread her open wide and kept ramming his cock inside her, deliriously muttering, "Oh, fuck, yeah!" His jaw tight, he kept plowing into her over and over, so lost in the feel of her, he just couldn't stop.

Till he had shivering right down to her toes, soundlessly crying out and tossing back her head as she came all over again. While he let out a deep feral growl, shouting, "Fuck, what a feeling!" as he jammed his cock deep inside her, his legs shaking as he climaxed, relentlessly pumping her full of his seed.

Amazingly, he still kept thrusting, until he finally gasped, collapsing on top of her, once he had nothing left to give.

Reaching between them, sliding a finger inside her, he smiled and said, "You feel that gush? That's my seed I just buried in your womb."

Jess studied his face, and looked at him wide-eyed, I guess never considering the fact that she might actually find herself pregnant after a night of bareback fun.

"I know it might sound crazy, but I don't think she'd be too be upset if it happened," I whispered to my friend Cory, as we watched them happily smiling into each other's eyes, while he gently stroked a finger across her cheek.