Pimpin' Out My Stepsister Ch. 02

PIMPIN' OUT MY STEPSISTER CH. 2

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

Everyone in this story is over the age of eighteen.

After a night of kinky fun, my stepsister Jess was in her bathroom cleaning up, getting a shower. While I was busy calling my friend Raj, trying to line up another "date" to help her raise some money for her college tuition.

When I asked Raj if he was busy, he sounded a little tired the way he yawned and mumbled, "I've been studying since this morning, and just turned off my computer. I was gonna grab a snack and try to get some sleep. Why, what's up?"

"Well, my sister is trying to earn some money for college. So, I wondered if you and your dad would like to come over?"

"Ah, she's not selling cookies, or Tupperware or any of that kind of shit, is she? Because if she is, I'm sorry, but I'm not interested."

I laughed, imagining how shocked he'd be once he discovered what she was really up to. "No. It's nothing like that. Just come over with a couple of hundred bucks and you'll find out when you get here. And I promise you'll be glad you came."

"Okay. But why do I need to bring my dad?"

"Trust me. I've got a pretty strong feeling, once he knows what's happening, your dad will want in on this, too."

"Okay. We'll be there soon."

Jess looked positively giddy, anxiously waiting by the door in her thigh-high sheer pink wrap and tiny thong, and come fuck me heels.

No surprise, I was getting hard just looking at her, since I could see her big, luscious tits rising and falling, through her translucent wrap. And her nipples were already diamond hard; she was so eager to get busy with them.

Though hating to label her, I guess she was a bit of nympho, because she really got off on having sex. Tonight, she'd already sucked me off, got eaten out by friend Nicky's dad, then fucked him, before she blew Nicky. And lucky me, she even gave me a nice steamy little thank you fuck, once the two of them had left.

Now she was almost bouncing in her shoes, just itching to get it on with Raj and his dad. So, there was no getting around it, she really was insatiable.

Raj barely had a chance to ring the doorbell and Jess flung the door open and pulled him in for a hug. He looked pretty shocked when he hugged her back and realized as his hands trailed down over her slender body, that she was almost naked, when he found himself squeezing her bare ass.

I couldn't hold back and quietly laughed at the way his dad's eyes flared once he followed him inside and got a look at my sister, with her tits exposed, and her pussy barely covered by her tiny thong.

"What on earth is going on here?" he asked, suspiciously looking around at the three of us.

I piped up and explained. "It's okay, Mr. Kumar. My sister Jess is just trying to earn some money to pay for college."

He waved a hand at her in her sheer little wrap. "So, what will she be doing, dancing for us in this outfit?"

Jess grinned, stepped in close, stroked his cheek and shook her head. "No. I'll be doing a lot more than dancing. Actually, you can do anything you want with me, once you've paid me."

His eyebrows shot to his hairline as he eyed her luscious tits, obviously dying to get at them. "And how much would it cost me to lick your pretty nipples?"

Since I was handling the money, I cut in and told him, "It's a hundred bucks for a blow job, and two hundred if you want to fuck her. And of course, you're more than welcome to have some fun with her titties while you're at it."

"And do your parents know you're doing this?" he asked, as he reached into his pocket for his wallet.

"No. They'll be away till tomorrow. So, while they're gone, I thought we could have some fun together," Jess said, grinning as she ran a hand down over his body, making him gasp as she brushed her fingers over the large bulge in his pants.

Once he dropped five hundred bucks on the table in the entry way, Jess stepped in and started to undress him. While Mr. Kumar reached up and quietly moaned as he cupped her breasts in his hands and got off on twisting her long, hard nipples between his fingers.

"You've got such beautiful perky breasts, my dear."

Jess grinned, looking pleased. "Well, if you'd like, you can slide in there and enjoy a little titty fuck, once I've got you nice and hard."

"Oh, I would love that. That would be my biggest fantasy come true, to be able to fuck a beautiful pair of tits like these." Then he cautiously asked, "And can I come on them, too?"

Smirking, Jess nodded, as she unzipped his fly and pushed his pants down to the floor. "Of course. You can come anywhere you want, on my tits, in my pussy, or all over my face. The choice is yours, because I just want to please you."

His eyes rolled back in his head as he got off on the feeling of squeezing her big plush titties. "You're such a lovely girl, with such nice big breasts and beautiful hard nipples." Mr. Kumar chuckled. "It feels so good just to be able to touch them, I think I might even come, just from the sensation of squeezing them in my hands."

Considering his dad wasn't overly tall, Raj and I both looked at each other, surprised, as Jess sat back on her heels, looking equally amazed, once she got him naked, and we all got a look at the size of his cock, jutting straight out from his body, like a flag pole, and already dripping with pre-cum. He was really long and fairly thick, so I knew Jess was going to enjoy him, no matter what he decided to do with her.

I chuckled as we watched Jess lead him over to the couch, when Raj leaned in and whispered, "Do you think your sister would let me fuck for another two hundred bucks?"

I chuckled, already knowing she'd be more than willing. "If your dick is anything like your dad's, I think she'd be happy to let you do anything you want with her."

Raj nodded, watching his dad interacting with Jess. "Then I think I'll go for the whole deal, and get her to blow me, before I get in there and pound her."

"Yeah, I'm sure she'd like that," I quietly whispered back, knowing Jess had to be thrilled to have two more well-built men to help her get off, now that I knew how much she needed it.

Eyes-wide, Raj and I watched Jess, naked on her knees, shivering with excitement, as she cupped her tits in her hands and slid them over his father's slightly furry thighs. She looked elated, happily humming around his cock, when she plunged him into her mouth and began to suck him off. While Mr. Kumar groaned, looking spellbound, as he gazed down at her and began to flex his hips, pumping his dick in and out of her mouth. Twisting his hands into her long blonde hair, as the pressure mounted, he started tugging as she blew him, making Jess whimper even louder.

My sister looked so blissed out, as she got off on deep-throating his dad, I was starting to think that money might not be her only motivation, as I realized that I'd never seen her so happy. Being able to share her body, seemed to be something she actually craved. And if I was lucky, once the two of them left, maybe she'd be willing to share a little more of herself with me.

Raj's dad, softly groaning and running his hands through her hair, murmured, "You're such a beautiful selfless girl, doing this for me. It's been so long since I've felt the touch of a woman, you have no idea what this means to me."

Dusting kisses up and down along his shaft, while gently massaging his balls, Jess gazed up at him and smiled. "Actually, I think I do. Everyone craves affection, and I'm just glad to be here for you to give you what you need."

We watched his legs starting to shake, as he began to erupt. Clenching his jaw, Mr. Kumar grunted and took hold of his cock and aimed it at her tits. Jacking it through his fist, quietly growling, he started shooting, till he had her tits covered in a nice thick coating of white-hot cum. Her nipples looked so erotic, dripping over her heaving breasts and flat little tummy, right down to the floor. They both smiled and quietly laughed when she grabbed a glob off her right nipple and slid it into her mouth, then opened up to let him see it sitting on her tongue, before she swallowed it, and happily licked her lips.

While his father dropped onto the couch, looking a little dazed after what he'd just enjoyed with my sister, Raj quickly peeled out of his clothes, and smiled at Jess as he stroked his thick, hard, veiny cock in his fist.

Of course her eyes lit up, once she saw how big and thick he was. "So, I'm guessing you'd love to feel that nice big dick of yours sliding over my tongue, eh, Raj?"

"Yes, please," he said with a teasing smile as he walked over and stood in front of her with his cock bobbing in her face. His hand trembled as he reached out to smooth his fingers over her long, silky blonde hair. While Jess reached out to stroke his erection, dusting hot open-mouth kisses over the swollen crown, making it pulsate and grow even thicker. "But I'd also love to come inside you, if I could," Raj said, looking a little hesitant.

"Mmm. I'd like that, too." Jess moaned as she licked up the big drop oozing from his tip, smiling as she swallowed it. Before she slid him past her lips and started gently sucking, drawing him deep into the heat of her mouth. And by the looks of it, half way down her throat, judging from what was bulging out of her neck as Raj clutched her face in his hands, flexed his hips and softly growled as he gazed into her eyes and fucked his way inside her.

Entranced, the three of us stared wide-eyed at the erotic sight of his long hard shaft buried balls deep in my sister's hungry mouth. Her lips stretched tightly around him, making her look like an actual porn star, happily smiling up into his deep brown eyes as she explored him with her tongue.

Just watching the way she was sucking off my friend, blissfully moaning while sliding her tongue up and down along his shaft, and rolling his balls between her fingers, as she dreamily gazed up into his eyes, was almost enough to get me off. So, I thought I'd better slip out of my clothes, so I could at least stroke my dick while I watched them.

I smiled at Raj's dad, Mr. Kumar, when I realized he had his shaft in his hand, and was already semi-hard, just from watching her work her magic on his son. As Jess clutched his thighs, and eagerly pumped him in and out of her mouth, happily sucking him off.

It wasn't long till Raj was groaning like a beast, fisting her hair in his hands and flexing his hips as he fucked her face. "I think I'd better get you on the couch, so I can get inside you," he said in a deep throaty rumble, his legs really starting to shake, obviously getting pretty close to the edge, and almost ready to climax.

Happy to oblige, Jess gave his cock one last sloppy kiss, wiped away the saliva dripping from her lips, and hopped to her feet. Flashing us all a saucy grin, Jess got on the couch and spread her legs open wide, so we could see her pretty pink pussy glistening with her arousal, just itching to be fucked.

His voice trembling, as he eyed her quivering puss, Raj asked, "Can I lick you first?"

Jess smiled, admiring his rigid cock. "Of course. You can do anything you want with me, I'm yours, Raj."

Raj had been dating a girl for about a year before they broke up a few months ago, so I knew he really needed this. He was so desperate for a taste of her, he had all of us groaning as we watched him get down between her legs, grab her ass in his hands and lift her bottom right off the couch, so he could slide his tongue inside her and bury his face between her thighs to feast on her, obviously starving for it.

"You taste like honey," he murmured, licking her up and down, while Jess writhed, when he dragged his tongue from her tight back hole right up to her swollen clit, tracing circles around it with the tip, making her shiver. "I'm really going to enjoy getting inside you," Raj murmured as he hungrily fucked her with his tongue.

Already breathless, every inch of her quivering, Jess nodded. "And I can hardly wait to feel that big, bad boy splitting me open wide once you push your way in."

I really started oozing as I watched the way she was shaking, as Raj desperately growled, suckling her clit between his lips, while giving her a rough little finger fucking.

Raj's dad and I just stood and stared in awe, beating our meat in our fists, quietly groaning together as we got off at the sight of her losing it. Jess just looked beautiful as she came, with Raj's tongue buried deep inside her, while she shivered right down to her toes.

"You have such a sweet pussy, I hate to leave it, but I've got to get inside you before I mess up the couch."

"Then don't hold back, Raj. Just fuck me with everything you've got," she pleaded, desperately clinging to his muscular forearms.

Coyly smiling, Raj lifted her legs onto his shoulders, grabbed his cock and lined himself up. "At this point, you've got me so hard, I won't be able to hold back, because I really need to fuck you."

Jess's eyes rolled all the way back in her head as he carefully pushed his way in, till he managed to pop his big, red, angry, cockhead into her tight little opening. Till he had her stretched to the max around him, his thick shaft lodged just inside her. "Oh, fuck you're tight," Raj murmured as he flexed his hips and started thrusting, gradually burying himself inside her a little deeper with each pump.

Mr. Kumar smiled over at me, looking proudly at his son, eagerly mating with my sister. "She's such a sweet girl, sharing herself with us like this."

"She really is," I agreed, since she'd made everyone so happy, just from letting us enjoy her.

My heart was pounding like a drum as I watched Jess starting to quake, as my friend Raj picked up his pace and really started to ride her. Slamming her ass into the couch, he growled like a beast as he pounded the living hell out of her pussy. I knew she had to be getting close judging from how hard he had her shaking, every inch of her quivering, she cried out moaning louder with every thrust.

"Raj, it just feels so crazy good the way you're stretching me inside to take you. It's the most delicious sting I've ever felt. And I can't wait for you to erupt and fill me up and paint my insides with everything you've got."

Suddenly, Jess threw back her head, opened her mouth and shrieked, her back arching right off the couch when Raj bent and drew one of her hard, red nipples into his mouth, giving it a little bite and tug, while he kept thrusting deep inside her. Gritting his teeth, savagely punishing her with his cock, we groaned right along with him, feeling every thrust as Raj swivelled his hips and drove into her deep, hard and fast, just the way she loved it.

"Oh, fuck! I'm coming so damn hard I can hardly see straight!" Jess cried out, uncontrollably shaking in his arms, as he clenched his jaw and ravaged her, slamming into her over and over, pounding her with everything he had. "Oooh, yesss!" Jess cried out, desperately quaking and clinging to his arms. "It just feels so good with you, Raj, I can't even describe it."

"And you feel like heaven," Raj told her as he picked up his pace and straight up railed her. Ramming his way inside her, pounding her ass into the couch, he slammed his teeth together, growled, threw back his head and cried out, "Oh, fuck me, yes!" as he came in blinding rush, and still kept right on pumping, giving her everything he had.

With one last gasp, he collapsed on top of her, his dick sliding out of her with a big gush of cum. Jess grinning from ear to ear, reached down between them and slid a little dollop between her fingers to paint her nipples, while she smiled against his lips, while Raj bent his head and kissed her.

"I want to see you again," he told her, dusting kisses all over her face, making her laugh as she happily wrapped her arms and legs around him and hugged him tight.

"I'd love to see more of you, too." Her breasts heaving, as they struggled to catch their breath, Jess playfully wiggled her eyebrows. "Especially like this, naked between my legs."

Raj chuckled and kissed her one last time before got to his feet, and smiled at his dad, who was grinning right back, after seeing the fun his son had just had with my gorgeous sister.

I noticed his father left another two hundred bucks on the table as they were leaving, probably because he was so happy with everything they'd shared.

I had a feeling they'd be back too, as I eyed my deliriously happy sister, still on her back on the couch, looking so hot with her legs parted, with a nice thick line of Raj's cum sliding out of her pussy, and her big, beautiful tits still heaving hard.

"So, I'm guessing you're done for the night," I said, still jacking my cock in my fist, as I eyed her beautifully swollen pussy.

Licking her lips, Jess smirked watching my sticky cock fly through my fist. "Why? What did you have in mind, little brother?"

She'd got me so aroused, watching her getting everyone off, I decided it was time to call the shots and I straight up told her, "Get on your knees, ass in the air. I need to come inside you before my balls burst. You've got me so fucking hard, I'm throbbing."

Jess didn't hesitate. She was on her knees in a heartbeat, shaking her ass, looking sexy as fuck, she grinned at me over her shoulder, practically begging me to plow her. Her legs parted, cum oozing from her red, hot cunt, just aching to be filled and fucked and pumped full with another big load, I swear I'd never seen anything so arousing.

When I got in behind her and pushed two fingers into the heat of her, she mewled like a hungry kitten as I gave her a little finger fuck, making her come all over my fingers.

My knees shaking, I was so desperate to get inside her, I took hold of my throbbing cock, lined myself up and groaned at how incredible it felt as I popped my big, fat cockhead inside her and started thrusting, stretching her insides to take me, as Jess desperately whimpered, eagerly clenching around me.

"Ooh, you're so thick, it feels like you're splitting me in two. But it's almost indescribable, it just feels so good the way you're invading my body and filling me up, ramming your way inside me, you beast. It's such a delicious sting, I can already feel the pressure beginning to mount, just from the delectable pain of you tearing me up inside with that big, fat cock."

"My balls are getting tight," I warned her, as I felt the familiar rush racing through my veins as I kept flexing my hips, pumping into her body. "I'm going to come so fucking hard, you're going to be floating, Jess."

"Then fill me up, Skippy. Don't hold back. I want to feel you exploding when you coat my womb with your seed."

Gritting my teeth, I nodded. "Here it comes." My heart hammering in my chest, I kept thrusting, driving my cock into over and over, like a rutting beast. Till finally, I threw back my head and growled as I felt the explosive gush firing up from my balls, as I erupted deep inside her clenching pussy, coating her insides with another big, hot load.

Once I'd come, still buried in her deep, I collapsed on top of her. Still fighting to breathe, Jess turned her head and smiled, when I pressed a kiss to her back, and told her, "Oh fuck, that was amazing, Jess. You feel so good, I wish I never had to pull out."

"You're telling me. You made me come so hard, my poor pussy won't stop clenching, it's like an orgasm that won't quit."

I pressed a kiss against each of her taut little ass cheeks as I took hold of myself and pulled out, enjoying the erotic sight of my sister's quivering pussy expelling what looked like a gallon of thick white cum.

"So, do you think you've had enough now?" I asked her as I got to my feet with my cock still dripping.

Even after the savage dicking I just gave her, she just eyed me, looking shocked. "Are you kidding? The money I've made tonight will barely pay for my books. While I grab a shower, I think you'd better phone another friend, and hopefully it won't be too late for them to come over for a little fun."

I shook my head and laughed as I watched her wiggle her way to the bathroom with her legs clenched together, so she wouldn't leave cum spots all over the hardwood floors.

While Jess was in getting a shower, I cleaned up and took care of the couch. Once I got dressed. I decided to phone my friend Cory, who lived with his divorced dad and three brothers, who were all into sports and really buff.

I figured if five of them weren't enough to wear her out, then I could just keep calling around to see who I could get to come over, till she finally gave in and decided she couldn't take anymore.

Cory sounded intrigued, when I invited him over with his family, including his dad, who was a successful realtor with offices all over the state.

"So, what's going on? Are you having some kind of party?" Cory asked.

"You'll find out when you get here, buddy. I know you've always had a thing for my sister Jess. So, if I were you, I'd round everyone up, get in the car and get your ass over here as fast as you can. And bring all the cash you've got."

"Well, if it's something to do with Jess, then I guess I'd better turn off the football game, so we can head over there and find out what's going on."

I chuckled, thinking about how much fun they'd be having with my sister, as I told him, "Yeah, I think you guys are going to be pretty happy when you get over here. And you can thank me later."

I could already feel my cock beginning to thicken and twitch in my jeans as I imagined how elated my sister was going to be once she realized she'd be enjoying five big, buff men all at once.

She'd be in heaven.