Siblings... With Benefits? PT2 (Siblings With A Solution) (Patreon)

Jazz looked over at her clock. It was only a few minutes until six. "The dorms are mostly empty on Friday night. Most of us go to parties and shit and we're out until at least three." She says, her brother nodding. "Ok. So... What's that have to do with us?" Derrick still seemed really conflicted. Jazz couldn't blame him.

If she had even a modicum of will power she never would have mentioned anything about this.

But, what's done is done. And it's not like they're in love or some bullshit like that! They'll just help each other out with a problem. Any sibling would do that, right? Right! There was nothing wrong with this. Jazz shakes her head roughly. "I mean, that in about an hour or so, almost everyone will be gone for the night. Which means there's less of a chance for someone to knock on my door or for someone to hear us."

Derrick nods his head slowly, as he fiddles with the strings on his hoodie. Jazz hesitates, before scooting closer towards him. He freezes for a moment as she rubs his leg. "Look, we don't have to do anything. I'm stupid for even bringing it up." She says, giving him one last chance to back out. Sure, it'd suck for her, but she'd rather have a slightly bad time then pressure him into both cheating on his girlfriend AND committing a crime.

Which, she was too, she supposed.

"It's just so sudden." Her brother says, in a voice so small. "Like we were never super close until recently and what... What if this ruins that?" Jazz leans forward, giving his forehead a sisterly kiss. "Think of it like... Helping each other with homework. Or doing the other's chores." Derrick suppresses a smile, which Jazz will definitely consider a win.

"Alright, you've convinced me." Derrick says, actually sounding somewhat convinced. He does hold up his hand though. "I do have three rules." Jazz smiles. "Sure thing. What are they?" Derrick holds up one finger. "Rule one, is obviously, not a single person can ever know." Jazz nearly laughs. "Obviously. Second rule?" Derrick holds up another finger.

"Second rule is that if either of us decides to stop all of this, we stop immediately. Whether we're in the middle of doing... Stuff... Or we just wake up and don't want to do it anymore." Simple enough rules so far. "Deal. Last one?" Derrick holds up one last finger.

"No actual sex. It's not incest or cheating if we don't actually have full blown sex." Oh, how utterly and totally naive of him to think. They'll have that rule broken before midnight if Jazz has her way about it. Still, she nods seriously. "That's ok." She lies. "Anything else?" Jazz asks, and Derrick seems to ponder the question for a moment before he shakes his head.

"Nothing I can think of. Just be patient with me. I'm new to... Everything." He says lamely, and Jazz pats him reassuringly on his leg. "Hey, I'm right here with you. I'll teach you everything you need to know." Including how to properly have sex, even if he doesn't know he's going to learn it yet. Derrick practically lunges forward and embraces her in a hug.

While she does hug him back, she hopes he's not a cuddler in the sack. Jazz never cared much for that.

As the hug breaks, Derrick scratches his head. "So what do we do now?" They've got some time to kill, and Jazz knows just how to kill it. She flicks his nose. "Hey!" He tries to swat her hand, but she'd already pulled back. "If I remember correctly brat, you and me are due for a rematch on Smash." Derrick rubs his nose, glaring at her adorably.

"Get the damn game set up. Your ass is mine." Huh. She wonders if that's a threat, or a promise?

.........................................

Derrick sadly loses. Ten times in a row. The teen wants to slam his head against the wall, but he's got more self control than that. He looks over to his sister, who currently is having the time of her life. He stands up, walks over to her TV and shuts it all off. Jazz just laughs quietly as he sits back down.

"Something wrong Little D?" She asks mockingly. Derrick just shakes his head. "I'm never playing Smash with you again." The teen says, causing Jazz to laugh. "Ah you know you'll be back. I'm the only one willing to play and you know it." Which, yeah, ok she has a point. Derrick sighs as he leans his head against her shoulder.

"So, what now?" Derrick asks. His sister hums as she checks the clock. "It's almost eight. We can probably get away with some stuff right now I guess." Derrick's heart skips a beat, and when it returns, it's twice as fast. He takes a deep breath, and his sister rubs his back. "You ok?" She asks, and Derrick takes one last breath before nodding.

"Yeah it's just... I'm nervous." Understatement of the year really, but his sister just smiles and accepts it. "Well don't worry. This'll be fun! Promise." She says, before she starts clicking her tongue in thought. "Ok, so how about some kissing?" She asks. That's probably easy, he thinks. Wordlessly, he leans forward, and his sister does the same.

Jazz cups his face as the two inch closer, her breath hitting his face. A moment later, their lips touch. It's rather innocent at first as the two keep the kiss very tame. Derrick has to admit, he's not grossed out by it. Eventually, his sister licks at his lips, and he's all too eager to oblige her as he opens his mouth. Jazz's grip on his face tightens up as her tongue and his dance and twirl around each other. Derrick didn't think kissing could be this good.

Don't get him wrong, he's always enjoyed kissing Willow, but their make out sessions were rare, and even then they weren't as... As... Derrick doesn't know how to describe it. Eventually, Jazz breaks the kiss, her tumb running over his lips. She gives him a small, half smile as she takes a few breaths.

"Damn D, You're way better than I thought." He's not sure if his face was already red, or if her words did that to him.
"You uh, you're great at this." He says softly, and Jazz just shrugs. "I am a natural, aren't I?" She gloats, before Jazz licks her lips. "You can touch me you know. I'm certainly going to be touching you." His sister exclaims, before she leans back down and his lips are once again captured by hers.

This time though, her tongue doesn't enter his mouth. Instead, she licks and sucks on his lips as her hands run up and down his chest. Nervously, he reaches a hand forward, laying it down firmly on her stomach. He rubs it for a moment, before snaking his hand further and further up. His sister, however, is much more bold than he is.

As soon as he starts to move his hands on her stomach, she reaches under his shirt and feels his bare stomach and chest. Jazz pulls away slightly. "Not a lot of muscle on you huh?" She snickers. "I always knew you were a lazy dweeb." Derrick glares at her as he feels her body through her sweater. Sadly he's pretty sure she's more toned than he is, but whatever.

He sticks his tongue out at her. "At least I'm smarter than you." Derrick says, and Jazz laughs. "Yeah? Well I'm way hotter than you." Derrick glares so hard he can barely see her. "What, you already out of witty remarks? Guess I'm better than you at that too." An in attempt to shut his sister's stupid face, he slides his hand further up, grabbing her boobs at the same time as he lunges forward for a kiss.

He manages to knock her over, and he finds himself on top of her, his hands full of her boobs (even through the sweater they feel nice) and his tongue pushing into her mouth. Jazz laughs, though the sound is weird with the two of them still kissing. He breaks the kiss, and Jazz just raises an eyebrow at him. "What was that? You trying to shut me up?" She then gives a half snort, half chuckle.

"It'll take more than a loser dweeb like you to do that." His sister says, and part of him knows she's just goading him on. But still... He squeezes and rolls her breasts around, the sizable fleshy fun bags (did he really think that?) way more flexible than he assumed they'd be.

Willow doesn't have boobs. Not really anyway. And when he tried to lick her nipples, she squirmed uncomfortably and he stopped. He always had to stop... He breaks out of his thoughts when his sister sighs, the sound more of relief than of bordem. "You know... You're not that bad D." She says, before suddenly she pushes him. In a flash, she and him were both sitting on the bed. She had one arm wrapped tightly around him.

He was stuck. He tried to squirm, but Jazz just gives him a devilish grin. "Oh no, you got to feel me up, it's my turn now." His sister says, before using her free arm to rub at his knee. She doesn't stay there long though, and as she inches closer and closer to his shorts' waistband, his heart starts to beat faster and faster. This is really it.

No more playing around, he'll have to accept the fact that he's both fooling around with his sister, and he's kinda, sorta cheating.
Neither of these things feel particularly bad however, as his sister pulls his shorts down. It's a bit of a struggle for her though, doing this while he's sitting, but as she gets them down to his thigh, she stops.

His dick is now free. She whistles quietly. "Fucking hell Derrick. You really weren't lying." Jazz says, and Derrick grumbles. "I told you I had the right size." Jazz hums.
"I just assumed you were being... Optimistic." The older woman says, as she traces one of her fingers on his dick. He almost shivers. "This has got to be near seven inches. Right?"

Derrick blinks, completely stunned. "Yeah, it's really close. How did you know that by just looking?" Jazz grins. "I've seen my fair share of cocks Little D. Though yours is definitely one of the bigger ones." Derrick isn't really shocked by that. He knows he's a bit bigger than the average guy.

Jazz pulls her hand away from his penis, but only to spit in it. Then she immediately returns her hand, and firmly grasps his dick. Derrick takes a deep breath as she slowly moves her hand up and down. "So tell me D, how does my hand feel?" Jazz asks, her voice low and sultry. Is... Is she trying to go for dirty talk? Because there's no way in hell he knows how to do that
.
"I... It feels ok." Derrick says, unsure of himself. Jazz just rolls her eyes, though there is some playfulness to it. "Just ok? Am I doing better than your girlfriend?" Derrick bitterly laughs. "Definitely better... Your hand almost feels better than when we were fucking." He says, and though it pains him to say that, he won't lie. Jazz isn't just moving her hand up and down. There's a technique to it that she's doing and it's legitimately really nice…

She's twisting and turning her hand, the spit she used as lube now almost not even needed as he can feel pre-cum starting to slip out and onto his dick. He bites down on his lip as he refuses to finish so soon. Jazz however... She licks his cheek. "Oh? Are you getting close?" Jazz whispers the words, and Derrick can't speak. He needs to focus. But she doesn't let him. Jazz starts to lick and kiss his neck as her hand goes faster.

"I don't... I don't want to..." Jazz bites down on his neck, the sudden pressure and mild pain slowing down his orgasm. But it doesn't last that way for long, not when she starts sucking and biting his neck. "Fucking hell..." Derrick mutters under his breath, the sensations all attempting to overcome him. As his dick starts to pulse and throb however, Jazz immediately stops. She pulls both her hand away from his cock and her mouth away from his neck.

He doesn't whimper. He doesn't.

"Aww, you upset Little D?" Jazz asks, the sickeningly sweet way she talks makes her seem innocent, but Derrick can't even begin to care that she's the furthest thing from it. "Why'd you stop?" He asks. He doesn't whine.
"Don't whine about it, I just need to make sure you'll have enough juice for the rest of the night."

Derrick glares again (though he knows Jazz would call it a pout) and jabs a finger into her stomach. She just laughs. "I'm not a one-shot wonder, ok?" In fact, he can go three or four times he thinks. Especially right now. Jazz rolls her eyes - and this time it isn't playfully - as she grabs Derrick and falls back onto the bed.
Again, he finds himself on top of her, and she jabs a finger into his stomach, mirroring him from before.

Unlike her though, he doesn't laugh. He winches. "You want an orgasm? Make me cum then." Jazz says, and then smirks up at him. "Rock my world, I'll rock yours." Derrick may be new to sex, but he's not naive. This could be challenging or it could be nearly impossible depending on the type of girl his sister is.
Still, he needs a release. Badly. So he nods.

"Alright. I'll give you the best damn orgasm of your life." He promises, and watches as Jazz playfully scoffs. "Sure. Get to work." His sister practically orders. Derrick wonders what he should do first. Undress her? Feel her up some more? He's not sure, not at first. But then he decides to do what every single person has done at least once in times of hardship.

He wings it.

Derrick runs his hands underneath her sweater, feeling her bare stomach for the first time. He's tempted to go north and grab her boobs, but for now, he's got to focus on her. Even if she likes her breasts being played with, that won't bring her any closer to an orgasm. He... Thinks. He pushes her shirt up to reveal her stomach, and he kisses it gently.

His slow, sensual pecks turn into tiny bites. Jazz sighs. "Really not feeling anything. I thought I was going to have the best orgasm ever?" His sister taunts. Derrick ignores her, doing his best to stay focused. She didn't seem phased by his efforts on her stomach, so instead, he tugs at her jeans.

"Finally, I thought you'd never take them off." Jazz says, and Derrick takes a deep breath. "If you're going to critique every move I make, then what am I doing here?" Jazz blinks, surprised by his sass apparently. "You're here cause you got a dick and I need one." Jazz states, though Derrick rolls his eyes.

"How romantic." He deadpans, as he finishes pulling her jeans off. He tosses them to the floor and stares at her panties. They're dark red, similar to her hair. Jazz gives him a small kick to the side. "Like what you see?" The older girl teases, and Derrick quickly - too quickly - shakes his head. "Like I could like anything that comes from you." Derrick says, and he knows it's a weak retort, but he's not quite on top of his game right now.

Jazz just smirks at him, before she opens her mouth. In an attempt to shut her up, Derrick rushes back to his knees, and rubs her pussy through her thin panties. The effect is immediate, and Jazz lays her head back. "Fuck, no one's touched me in ages." His sister says quietly. Derrick files that information away to be recycled and removed from his brain, and he goes to work.

He teases her, his rubs focused and slow. He licks at her inner thigh while his hands keep their pace up. The teen listens as his older sister lightly moans and sighs. After a short time of this, he decides to end the teasing. He grips and pulls his sister's panties down. Jazz moves her legs, giving him room to get them off of her. Once he's finished, his eyes lock onto her vagina. He swallows hard, before lowering his head down next to it.

The smell is unique, and intoxicating. He doesn't think he could be anymore turned on then he is right now. He nervously reaches for it with his hand, and starts to rub at her folds. "Hmm... You're not half bad D." Jazz says, her voice sounding sincere. Derrick, after some careful touching, and he's sure that she's wet enough, rubs around her entrance as he tries to see exactly where the sweet spot is.

Once he finds it, he slips a finger inside, while he goes for said sweet spot - and licks her clit. Jazz's reaction is instantaneous. She shivers on the bed, and Derrick has to hold back a grin. When he did the same thing for Willow, she just pushed him away in frustration. He's honestly glad to know - for sure - that it wasn't him being bad at sex that ruined his and Willow's first time.

"Where... The fuck did you learn how to do this?" Jazz asks as she tries to control her breathing. Derrick raises his head slightly. "I read a few things. Wanted to make sure my first time was memorable." Which it was, but not the way he wanted it to be. Jazz laughs, though it turns into a moan. "Her loss is my gain. You really aren't bad at all dweeb." Jazz says, and Derrick is determined to make her cum.

Maybe she'll stop with the insults if he does a good enough job. Though he doubts it.
He brings his mind back to the task at hand, and continues to lick and suck on his sister's clit. He adds another finger into her pussy and really notices just how wet and tight she actually is.

Willow was tighter, but definitely nowhere near as soaked as Jazz is. Jazz's pussy is also more... Textured, he guesses, is the word? Willow had a rather smooth vagina, with tiny bumps here and there. But Jazz is the exact opposite.
He... He wonders what it would feel like if his dick was inside.

Derrick tries to will the thought away, but it stays. In an attempt to take his mind off of that, he looks up at Jazz. Which only made it all worse. She was squirming now, her breathing getting more and more erratic as he tends to her pleasure.

"Fuck... Fuck this is so damn good." His sister says, before she lets loose another moan. The sound is just... He wants to hear it again. He redoubles his efforts, moving and wiggling his fingers around more inside of her wet cavern. Her clit never leaves his mouth as he acts like it's a piece of candy that needs desperately to be sucked and licked.

Finally, Jazz reaches a breaking point. She squeezes his head with her legs as her back arches. "Fuck, FUCK!" She screams, as her pussy tightens almost painfully around his fingers. But Derrick doesn't dare stop. Not until she falls back on the bed. And even then, he merely slows down. His ministrations become much more subdued as his sister recovers from her orgasm.

It's not until she laughs that he stops.
"It wasn't the best one I've ever had, but fuck... That was definitely top ten." Derrick wonders if that's on the high or the low end. "I'll give you the best one ever one day. I swear it." Derrick has no clue where THAT came from, but his sister just grins. "Oh, so you definitely want to do all of this again?" He chews on his lips for a moment as he thinks of a response.

"I really liked that." He settles on saying. "It was way more fun when the person you're doing it to actually enjoys themselves." Jazz hums thoughtfully. "Yeah, I guess it would suck if the other person wasn't enjoying it." Derrick wonders if she was ever in that position. He's about to ask, when suddenly she grabs him and once more switches their positions. She's on top now, and he's on bottom, grumbling.

"I wish you would say something instead of just chucking me around like a bag of ice." Jazz smiles, and smacks his chest. "I'd apologize, but A, we both know I wouldn't mean it, and B..." She runs her hand down his chest, ending at his shirt. Jazz grabs it and lifts it off of him. "Well, I think what I'm about to do to you will count as an apology." Jazz grabs at her sweater, pulling it over her head. She then takes her bra (it matched her panties, Derrick noticed) and unclips it, the fabric falling from her body afterwards.

Derrick stares at her chest as she grabs his boxers, pulling them and his shorts the rest of the way off. Her boobs were nice. Large, yet still perky, unaffected by gravity in the slightest. Jazz chuckles, squeezing her breasts between her arms. "You really like my tits, don't you D?" Jazz asks, her sultry voice cutting through his hazy mind. Fuck, he's so damn horny right now. He really doesn't care in the slightest that she's his sister anymore.

He licks his lips. "Yeah... Yeah they're awesome." Jazz reaches over him and opens her nightstand drawer. "Well, you can grope 'em all you want, until I find what I'm looking for." Derrick doesn't need a written invitation, and her words are barely finished as he reaches up and grabs her bare naked boobs. His hands practically melt around them as he feels her up.
His first thought is that he really can't believe how soft they are. Like... Fucking hell.

His thumb moves across her nipple, and all Derrick can think about is how much he wants to suck on her boobs. Sadly she pulls back before he can ask. He notices that she now has a tube in her hand, and when he starts to sit up, she quickly pushes him back down.

"No. Stay." Jazz says firmly, and Derrick huffs as he looks at the tube in her hand. She opens it up and starts to... His heart skips a beat. Jazz starts to oil up her chest. And she doesn't just put a little on. No, she empties the entire bottle on her boobs. Some of it drips down onto his stomach as she lathers her breasts with the sticky substance.

"I figured that since Willow doesn't have tits as awesome as mine, that she probably never did this for you." Jazz says, as she tosses the bottle away. She scoots down in her bed just a bit, and grabs his dick. After a few tugs, he's back to full mast and Jazz just smirks at him. "I promised I'd rock your world. So you better hang on tight." That's the only warning he gets before his cock is promptly shoved in between her boobs. The oil quickly covers his dick and his thighs as well as his stomach not long afterwards.

Derrick sucks in a breath as she starts to move her breasts up and down around his rock hard cock. It slides easily in her cleavage with the amount of oil she covered it in. Her bed is going to be so messy after this is all said and done, Derrick thinks. "Do you think I need more oil?" Jazz asks rhetorically, and Derrick holds back a moan as his dick is smothered in her soft, silky, sticky tits.

"I... Fuck." That gets a snort out of Jazz. "What's wrong little bro, cat got your tongue?" Jazz says as she pushes her boobs together, as hard as she can. She then holds them tightly as she moves faster. Son of a bitch, this feels so damn good. Derrick can't stand it. "Your tits feel amazing Jazz. I love it." Derrick confesses, his mind back to being hazy with lust.

"Aww, thanks D. Your cock is really nice too." Jazz says, her smirk still plastered on her face. "It's so big and hot between the ladies. I can't imagine what it'd feel like inside me." Derrick can't either. But he wants to find out. Wants to find out so badly. Jazz keeps the pressure up, and with the oil now getting all over his lower body and the bed, everything is becoming one sticky mess.

"Fuck, I did overdo it didn't I?" Jazz asks, though there's no hint of regret in her voice. Derrick laughs breathlessly. "You did, but that's fine. I love it." Jazz smiles at him, before rubbing her tits up and down quickly, alternating them between his dick. "Then why don't we add some more to the mess D?" Jazz says with her voice dangerously low.

Derrick can't take it anymore. His half sitting position falters as his body falls back on the bed, and he just barely has enough time to look up as he cums.

Thankfully, Jazz keeps going. She doesn't stop, not until he finally stops ejaculating. Derrick takes slow, delicate breaths as his heart calms down from the orgasm. He chuckles as Jazz slowly jerks him off with her tits. "I take back everything I said about this arrangement. I love it." Derrick says, as he looks into his sister's eyes. They practically glow with excitement.

"So, does this mean you'll get rid of that pesky 'no fucking' rule?" Derrick is still a little bit hesitant if he's being honest. He really doesn't want to fully cheat on Willow. He's pretty sure he's in love with her after all. But... One look at his sister brings those walls down.

"Yeah... Yeah. Let's do it." He says, but he quickly points at her. "Not now though. This bed like, really needs to be cleaned. And so do we." Jazz deflates slightly, but does wince when she looks at the state of her bed. "Yeesh I really did go hard on the oil." She exclaims. Derrick almost laughs, but coughs instead.

"We can always do it later. Until then, we should definitely clean up." His sister agrees, and it's not long before her sheets are washing and the two are together in the shower. Nothing actually happens though. The two just clean each other up. Derrick isn't quite sure where all of this is going to go…

But fuck, he can't wait for more.