Pimpin' Out My Stepsister

PIMPIN' OUT MY STEPSISTER CH. 1

©2025 Smuttyandfun All rights reserved

Everyone in this story is over the age of eighteen.

I was busy studying for an exam when my stepsister Jess wandered into my room, of course without bothering to knock.

"Whoa," I said the moment I turned my head and saw what she was wearing. Holy fuck! She looked like sex on legs, in her thigh-high sheer pink robe, push-up bra, tiny thong and sky-high, fire-engine red come-fuck-me heels.

"What the hell, Jess. Don't you own any clothes?"

Smirking, she shushed me with her hand. "Calm down, Skippy. I just want to ask you something."

"Stop calling me Skippy. And I'm trying to study. I've got a physics exam tomorrow, so unless it's important, it'll have to wait." I turned my attention back to my laptop so I wouldn't have to look at her gorgeous tits spilling out of the top of her bra. She was such a smoke show, with her long blonde hair, and perfect set of curves, I could hardly believe we lived in the same house. Though I'd never tell her, I jerked off in the shower nearly every day just thinking about how sweet it would be to get her on her back and get her moaning.

I could still feel her standing there, staring at the side of my head, and I knew she wasn't going to leave till I heard her out. "Okay, what do you want?" I asked, hoping to get it over with, I turned back, steeled my nerves and looked at her.

"I was just wondering how much you'd be willing to pay to fuck me?" she asked, cupping her boobs in her hands, grinning.

"Wait. What?" She had to be yanking my chain, because now all I could think of was how incredible it would feel to rip that thong off her and sink my cock into her tight little pussy.

"Well, you heard what the parents said. Just because I got side-tracked for a bit, partied a little too hard, and flunked out of college, if I want to go back, they said it'll be my nickel this time. So, now I've got to find a way to make some money."

"I still don't understand what you're saying."

"Well, over drinks one night, a few girls at school confessed that they've made some really good money just from having sex. Of course, they only hook up with guys they know, so they're sure they can trust them. And apparently, they're making a shit ton of money, just for putting out."

I could feel my eyes flare as I looked her up and down. "Have you lost your freaking mind? Are you seriously considering turning tricks, just to go to college?"

She gave me an eye roll as she explained, "It's not prostitution if it's with people you know. It would kinda be like crowdfunding, only they'd be getting something out of it, too."

I planted my face in my hand and shook my head. "Jess, even for you, this is nuts. I can't believe you're serious. I mean, why can't you just get a job in an office or something for a while? You could probably make a decent salary just answering phones somewhere."

"I actually did check out a few jobs online, but unfortunately I'm not qualified to do much." Then she flashed me a naughty grin. "But I have been told that I'm really good at giving head. Not that you'd know anything about that. But if you've ever had the pleasure of having a girl go down on you, I'm sure I don't need to tell you that a lot of guys would be happy to pay big bucks to be with someone like me, who really enjoys it."

"My sex life is none of your business."

She stepped closer and patted my head. "It's okay, Skippy, I know brainy guys like you are often late bloomers. So don't feel bad, it's no big deal if you've never had your cherry popped." Then she stepped in behind me and I sucked in a breath when she began running her hands through my hair and down over my chest, till she was sliding her fingers over my abs, and tauntingly whispering against my ear, "But I bet you'd enjoy it."

I could feel my cock growing thick and hard in my boxers, and I wanted to tell her to stop, because no way did I want to lose a load, just from having her touch me. But when she spun me around in my chair, smiled and reached out and began stroking me through my sweat pants, my mind went blank and my needy cock took over.

I felt like I was in a haze, when she grinned and nodded at my bulge. "Let's get these pants down, so I can have a taste." Without even thinking, I was lifting my ass off the chair to help her, and she was tugging my pants down to my ankles.

When she looked up and got a look at my cock standing at attention, her eyes popped. "Holy fuck, Skippy! You're huge!"

I glanced down at my slicked-up dick and shrugged. I'd never really been into cock size, so I imagined that most guys were built the same way.

Still wondering if I was dreaming, I watched her drop to her knees, up-clip her bra, letting her magnificent tits bounce free. Before I could even think, she had my cock trapped between her warm plush, titties, giving me a kinky little titty fuck and getting her girls all shiny with what was oozing out of my dick.

Desperate to have a taste, she wrapped her hand around me, and started licking me up and down, moaning as she savored the taste of the juice, gushing out of my slit. "How did I not know you were packing something like this, little bro?" she asked as she plunged me past her lips and started sliding me over her tongue.

Deciding that I might as well enjoy it, my pulse racing, I dug my hands into her hair, flexed my hips, and began pumping into her mouth, fucking her face.

Then I heard a noise in the hallway and froze. "Holy shit, Jess! You left the door open, and the folks are going to catch us."

Jess just grinned, sliding me through her fist. "Don't worry, Skippy. Remember they said they were going to a concert in the city? They told me as they were leaving that they've decided to stay downtown for the night, and they won't be home till late tomorrow. I think the sound you heard is just the cat batting around that toy mouse she likes to play with."

"I just hope you're right," I said, as she smirked, plunged me back between her lips, and dug her hands into my ass, driving me deeper into her mouth.

"Oh, fuck me!" I groaned, feeling my balls getting tighter and tighter the harder she sucked. I realized she was right; my sister really did know how to give head.

She winked and let go of me just long enough to say, "Maybe later. But now I want to feel this monster exploding in my mouth."

"Well, you're gonna get your wish, because I'm really close. You've got me right on the edge."

Happily smiling around my cock, rolling my balls between her fingers, she tipped her head back, till I was pumping into her throat so deep that I could see my dick bulging out of her neck!

Clutching her head in my hands, I warned her, "You better be ready Jess, because I'm going to come so fucking hard, it'll choke you!"

Nodding her head, she just kept smiling around my shaft, still working her magic, constricting her throat muscles around my throbbing erection over and over, coaxing me into giving her what she needed - a nice big load of white-hot cum.

Desperately digging my hands into her hair, I could feel the pressure mounting, like a boiler about to explode, as she got me closer and closer to the edge. Gritting my teeth, I growled as the most incredible jolt shot down my spine right to my aching balls and out of the end of my cock. "Oh, man, here it comes!" I warned her, as I clutched her head, and kept pumping, shooting the biggest load I'd ever shot straight down her throat. And amazingly, she managed to swallow every drop without even gagging.

Jess was grinning as she pulled back, wiping a hand across her swollen lips. "Hmmm, that was nice," she cooed. "So, do you think any of your friends would pay to have me go down on them?"

Every inch of me trembling, I nodded. "Oh yeah. They'd be happy to pay whatever you want, if you suck them off like that."

We both turned and looked at my desk, when my phoned chimed. I picked it up, and took a look at the screen. "It's Nicky. He was supposed to come over to study tonight," I said, wondering if I should tell him to forget it.

Jess just grinned. "Maybe he'd like to come over here... just to come."

"Are you serious? You want to blow my friend Nicky, too?"

She shrugged. "As long as he'll willing to pay, I'll do whatever he wants."

I nodded. "Okay. Let me talk to him."

"Hey, Nicky," I said, my eyes glued to my sister's heaving tits. "If you want to come over, Jess is home."

Nick sounded confused. "Okay. So, is that going to be a problem?"

I chuckled, eyeing her diamond hard nipples, she was tugging between her fingers. "No, it's not going to be a problem for you, buddy. Just bring over a hundred bucks, and you'll see what I mean when you get here."

After I hung up, Jess was smiling from ear to ear, looking really excited. "Yeah, a hundred bucks a pop sounds good."

"You know his father is driving him over here. So... you may want to cover up."

Her eyes lit up and she chuckled, jiggling her titties. "Or not."

"Seriously, Jess? Don't tell me you're planning on blowing his dad, too."

She shook her head and slowly began to smile. "Nope. I'm planning on banging the living fuck out of that stud muffin. The man is a perfect DILF, tall, dark, handsome and divorced, with loads of money."

I just shook my head, glad that the parents wouldn't be showing up any time soon. Or they'd be pretty shocked to find their daughter doing the nasty with my friend's dad and probably anyone else who had a hundred bucks to spare.

The moment Nicky rang the doorbell, Jess raced past me, already shivering with anticipation as she pulled open the door.

Seeing Jess standing in the doorway in just her robe and panties, with her nipples fully erect, Nicky looked so shocked, Jess and I both broke out laughing, as she beckoned him to come in.

Before she closed the door, his father came rushing up behind him, holding his back pack. "Nicky, you forgot your bookbag in the car." When he glanced up and got a look at Jess half naked, his eyes flew open and he muttered, "What the hell is going on here?"

Jess just grinned and ushered him inside. "Come on in, Mr. Greco. We're just having a little fun tonight. And of course, you're more than welcome to join in."

I could see he looked conflicted, looking down at her gorgeous tits, then back up her pretty face. And since Nicky had mentioned that his dad hadn't really been dating since his parents split up last year, I'm sure he was tempted to throw caution to the wind, give in and take whatever she was offering.

"Where are your parents?" he asked, anxiously looking around our big family room, before his gaze zoomed back in on her big, lush tits.

"They've gone to the city, and they won't be back till late tomorrow," Jess explained. "Which is why we've decided to have a little fun tonight."

I could actually see him swallowing pretty hard, when Jess stepped up, took hold of his shirt collar and brushed her lips across his. Nicky and I smirked watching his father's hands shoot around her waist, pulling her in even closer, as he breathlessly asked, "So how does this work?"

Deciding I'd better handle the money end of things, I piped up, "Jess is trying to pay her college tuition. So, it's a hundred bucks for a blow job. And it'll cost you two hundred to fuck her."

I thought he might object to me pimping her out. But probably because the money would be going towards her education, he just nodded, pulled out his wallet and handed me three crisp one-hundred-dollar bills. Smiling into my sister's big blue eyes, he clutched her ass and squeezed, drawing her against his erection, bulging in his pants, and said, "I think that ought to cover it."

For a moment Nicky and I just stood and watched them kissing, Jess smiling against his lips, as she stripped him off. Both of them hungrily moaning out loud as she slid her hands down over his bare chest and down over his abs, till she was clutching his big, hard cock in her fist.

Rolling his eyes, Nicky finally realized that he should get in on the action, and he pulled off his sweater and ditched his boxers and jeans, while I did likewise.

"So, where are we doing this?" Mr. Greco asked, his hands massaging her tits, and his voice all low and growly as he smiled into her eyes, with his rigid cock standing straight up in the air between them.

"Why not right here?" Jess suggested, nodding at two long leather couches sitting on either side of the big stone fire place.

She winked at us, "And feel free to watch, guys. Because I've never been shy, and I do love an audience when I'm getting it on."

Probably too blissed out to care, Nicky's dad didn't seem to mind us being ringside, eagerly watching every move they made.

While the two of us groaned watching him peel off Jess's tiny thong and toss it aside as he spread her out over the couch, shaking his head at the enticing sight of her juicy pink cunt, just itching for him to reach out and slid a finger inside her. A deep rumble came out of him when he buried his head between her legs and had her squealing her head off as he ate her like she was the best thing he'd ever tasted.

"Oh, fuck. I can hardly wait to feel those big, lush lips on me," Nicky said, as we stood side by side stroking our dicks. I could feel my legs shaking as we watched them getting off, my sister nearly ripping out his dad's hair, as she writhed beneath him, while he fingered her pussy and fucked her with his tongue.

I gotta say, it was crazy hot watching them go at it, especially seeing the way her whole body shivered and quaked as she climaxed. It was like watching the hottest porn I'd ever seen, only with my sister being ravaged, instead of some porn star.

Though seeing him go down on her was hot, watching them fuck was even hotter. Both of us let out deep needy groans when Mr. Greco parted her thighs and let out a feral growl as he fisted his himself in his hand and drove his cock into her slicked up pussy, getting me rock hard and every inch of me trembling as I slammed my dripping cock through my fist.

His ass muscles kept flexing as he rode her, while Nicky I quietly moaned, wishing that we were the ones pounding her ass into the couch.

Which got me thinking, as the unmistakeable scent of sex filled the air, as he punished her with his cock, and she tore up his back with her nails, that I should be entitled to something for pimping her out. Like maybe having the pleasure of riding her sweet little cunt, once they were gone.

"Oh, wow! I'm coming so fucking hard!" Mr. Greco cried out as he straight up railed her, driving into her hard, deep and fast, pounding her pussy like he couldn't hold back. The sound and the smell of them mating was intoxicating, as we watched him ride her to the finish line.

"Then come inside me," she begged, fighting to breathe. "I want to feel every pulse when that bad boy explodes."

Mr. Greco nodded, clenched his jaw, grabbed her ass and fucked her with everything he had, driving into her like a man possessed.

Our chests heaving almost as hard as theirs, Nicky and I got right in beside them so we could get off on the sight of his rigid cock slamming the living fuck out of my sister's quivering cunt. I'd never seen anything like it. I swear I could almost feel his dick ramming her pussy, like I was the one burying myself inside her.

"Oh, fuck yeah!" Mr. Greco cried out, tossing back his head, letting out a deep, ferocious growl, his whole body shuddering as he erupted. Still flexing his hips, he slowly kept sliding his cock into my sister, like he hated to pull out.

Feeling a little overwhelmed, Nick and I were both breathing pretty hard as we watched him slide out and wrap his hand around his slicked-up dick, shooting the last of his load all over my sister's heaving tits. While they both laughed, smiling at each other, obviously pretty happy about what they'd just shared.

Jess looked so elated as she smiled over at us, sliding her hands over her cum-covered titties, tugging at her nipples, before she closed her eyes and slowly savored the sensation of licking each finger clean.

While Mr. Greco mumbled, "Yeah, baby, eat that up. Eat up every drop." As he thoughtfully pushed two fingers into dripping cunt and gave her a little finger fuck, to give her a little more of what she needed to help her get off.

Nick leaned in and whispered, "Holy crap. Look at her shake. It looks like she's coming again. Do you think she'll be too tired to suck me off now?"

Watching her shiver right down to her toes, I chuckled. "Nah, she'll be up for it." I knew she would too, now that I learned that my stepsister was really into sex, and obviously couldn't get enough of it.

I'd no sooner got the words out, when I noticed that Jess was crooking a finger at Nicky, and licking her lips, to let him know that he was next.

But who knew Mr. Greco was such a kinky fucker? While Nicky's dad stared entranced at the sight of Jess sucking back his son's rigid cock, he dove back between her legs and hungrily ate up the cream pie that was oozing of her swollen cunt and coating her ass with his seed.

"Oh, fuck yeah!" Nicky muttered, desperately twisting his hands in Jess's hair, getting off on being blown for the first time in his life. While his father desperately grunted and groaned, as he got off on eating my kinky sister into another body shaking climax.

Nick looked a little startled when Jess grabbed hold of his ass, to drive him even deeper into her throat. It wasn't long till he was crying out, "Oh, fuck, here it comes. Jess, I can't hold back. Can you feel it? I'm shooting my load right down your throat!" Of course, she just smiled, and swallowed every drop he gave her, happily licking her lips once he was done.

After everyone had come, and they all pulled apart, I went and got a few bottles of cold water, figuring they might need a drink after all the fluids they'd lost from their sexploits.

Side-by-side sitting naked on the couch, all of them were shaking their heads, looking a little stunned, probably still trying to wrap their heads around what they'd just done with each other.

Before they got up to get dressed, they both seemed pretty pleased when Jess gave them each a little hug and kiss. I guess as a thank you for the money sitting on the table, as well as for all the fun stuff they'd enjoyed together.

As the two of them waved goodbye, grinning back at Jess, still naked on the couch, I had a feeling they'd be back, probably with a few more ideas on how they'd like to share her.

While Jess broke into my thoughts, when she sat up and said, "Okay, Skippy, I think we'd better clean up this gooey mess, and get all this cum off the couch. Or mom and dad will be wondering why their asses are sticking to it every time they sit down."

Once we had everything cleaned up, Jess smirked, took me by the hand and pointed down the hallway. "Now I think it's time I paid you back, little bro."

My head was spinning when she walked me back to my room, got on the bed, spread and legs, grinned and said, "Bet you never thought your sister would be the one popping your cherry."

I was so fucking hard, just from watching her tits bounce and her ass sway as we were cleaning. So, no surprise, I was more than ready to dive in and give her a pounding she'd never forget.

When she licked her lips, spread her legs as wide as they'd go and said, "Come and get it, bro," she didn't have to tell me twice.

I could hardly believe I was finally going to get my reward. I was going to sink my cock into her juiced up puss and fuck her till my head exploded or she passed out, which ever came first.

Taking a long steadying breath, I got down between her legs, my heart beating like a drum as I fisted my steely cock in my hand and poised it at her opening. Knowing that once I pushed my way inside her, and filled her up, I would no longer be a nineteen-year-old virgin, I'd be a man!