Siblings... With Benefits? PT3 (Siblings With Urges) (Patreon)

It was only a couple of weeks since Derrick and his sister had had their 'fun' in her dorm room. Since then, the two kept in much closer contact then before. At first, many of Jazz's texts to him were flirtatious. She even sent him some very scandalous pics as well. After a week of this (and a week of fighting off the urge to masturbate to said pictures) though, they started talking about everything.

[Sis : Ugh, Math is a fucking bitch that needs to be eradicated from the face of the 🌎.]

Derrick chuckled, as he laid in his bed.

[You really are that dumb huh? I bet I could do your classes for u AND score an A. Or a 100. Or whatever college does.]

[Sis : Hah! Don't make me laugh brat, u couldn't even fail right over here. Stick with middle school shit.]

Derrick snorted at that.

[Oh, so now you're fucking a middle schooler then? For shame Jasmine, for shame.]

[Sis : Hah hah, very funny mom.]

Derrick could feel the sarcasm oozing from her words. He bites his lip slightly.

[You know, I never really understood the whole daddy/mommy thing, but…]

He sends the message to give himself time to think. Jazz sends one right back though.

[Sis : I'm not calling u daddy fuckface ♥.]

Derrick holds back laughter.

[No! No I ugh... Next time we fool around and shit, you wouldn't mind if I uh…]

He was too embarrassed to say it. Thankfully, Jazz got the point.

[Sis : Oh! U want to call me mommy huh? I knew u you were a total sub.]

Derrick can't deny it, but he definitely isn't going to admit it.

[I just - I think I have a thing for older women. And no Jazz, I don't want to fuck mom.]

Fuck, Derrick almost threw up in his mouth thinking about it. It takes several minutes before Jazz texts him again.

[Sis : I almost died idiot! I nearly fell off my bed laughing so hard!!!]

Derrick imagines that for a moment, and then laughs. He of course, makes sure not to fall off of his bed.

[😂 u fucking dumbass!]

[Sis : 🖕]

Derrick grins slightly.

[Speaking of, when? I really want to.]

He hopes he's not coming off as needy or pressuring. It's just that his first time was terrible on all accounts and he can't take it anymore; Derrick wants to have a REAL first time.

[Sis : 🙄 All u men ever think about. Haven't any of u ever heard about dinner and a movie?]

[I'm fairly certain if I tried to take u on a date, youd get pissed and leave.]

[Sis : Heh, u rite. And I guess I can try to talk the parental units in the house into going out for a night. Offer to babysit my adorable baby brubber like the innocent angel I am 😇.]

Derrick nearly dropped his phone.

[I'm pretty sure there's not a single angel like u dumbass.]

[Sis : Oh, youll be singing a different tune when I'm through with u dweeb.]

[What if youre the 1 who'll be singing? I could easily have you doing the aheago face, laying on the floor while you beg me for more.]

Derrick's eyes widen as the next message comes in. It's a picture of her bare tits. She's shirtless, laying back on her bed. She's smirking up at the camera.

[Sis : Please bro, u can't handle me. Just be a goooooood boy and do exactly what mommy says.]

Derrick can't take his eyes off the picture or her message. Ever since that incident in her room, he can't get his sister out of his mind. Logically, he always knew she was attractive. But now it's like a... Like he was nearly blind and got a new pair of glasses.

[Sis : U still there? Did my tits turn you on that much?]

Derrick is about to respond, but a moment later, another picture comes in. This time, her smirk is gone. It's replaced with a much more... sultry look. Her free arm is underneath her breasts, and she's cusping her boobs.

[Sis : If u wanted more pics, u only have to ask baby 😉]

[The wink ruins it.]

His phone goes off not a moment later. Derrick regrets having his Bluetooth earphones in, because he nearly jumps. He quickly swipes the green telephone icon. "What? I was being completely honest."
"Ughhhh fuck you dweeb! I don't know why I waste these precious pictures on you anyway." Derrick snorts loudly. "You know you love me." He can practically hear her eyes rolling. "Yeah sure, whatever loser. At least I wasn't beating off." The teen groans.

"I wasn't even jerking off!" He says, maybe a little too loudly - his parents were home after all - "It's just, the pics surprised me." His sister chuckles. "Those aren't even the tenth nudes I've sent you. You really are that easily bothered by my stunning beauty?" Derrick clicks his tongue. "I wouldn't say that you're beautiful. That's going a bit far."

"Oh hoho! The boy has some sass to him today! How absolutely adorable."
"What? I'm not adorable, I'm badass!"
Jazz snickers over the phone. "Please, you're the furthest from badass. Maybe AN ass." Derrick pinches the bridge of his nose. He doesn't know why on God's green earth he has to be attracted to this thing. "I don't know what I see in you." His sister laughs. "Hot ass tits. Wonderful hair. The best pussy on campus."

"If you really have all that, then why couldn't you find a boy toy to fuck?" As soon as the words leave his mouth, Derrick worries that maybe he went a bit far. Thankfully his sister just scoffs. "I don't know what it is about these new age guys and all the 'I don't want sex, I want feelings and cuddles' and all that bullshit, but I'm sick and tired of it."

Derrick hums. "I get it, I guess. Though I do like cuddling.” Jazz snorts. "Yeah, I know. Had to find out the hard way when I graciously let you sleep in my bed." Derrick laughs softly. "I mean hey, you were fun to hold." Ok, now that was definitely a weird thing to say. "I... Don't know how to respond to that. But I guess I'll say thanks?" Derrick nearly kicks himself.

"Anyway, you said you'd try to come over soon?" He switches the topic. "Yeah I'll see what I can do. Hopefully we'll get together again soon." Derrick would go back up there, but her roommate was back and he knew that having any type of sexy time (ugh that felt so cringe) over there wouldn't be a good idea.
"Next class should be starting soon bro. Gotta go. Love you though! And have fun with my pictures!"

In typical Jazz fashion, she hangs up, always happy to get the last word. He puts his phone back down and sighs. Derrick should really be grateful that school was closed today, but honestly he's just been really bored. In fact, if he's not talking to Jazz, he's usually just laying here. He debates taking a nap, but his phone dings. Derrick lazily grabs it.

[Willow ♥ : Hey, can we talk?]

Derrick's heart skips a beat for a moment, before he quickly responds.

[Yeah sure, what do you need babe?]

Not a few seconds later is there a response.

[Willow ♥: My parents are out of town again. Come over?]

Derrick doesn't even need to think about it. He quickly types a response as he grabs his clothes and dresses.

[Ok! Be there in a minute!]

He's out of the house faster than he can say bye to his parents.

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

Jazz drops onto her bed with a thud. She's so damn exhausted. School sucks, there's no question about it. She's tempted to just sleep and forget about the last few hours of her life, but decides against it. Jazz wonders how easily she can talk her brother into some phone sex. Her roommate is supposed to be out for the night after all…

She's about to grab her phone when it dings. Jazz blinks at the device for a moment, before looking at her hand. "Am I psychic?" She asks herself, before shaking her head and grabbing her cell. The noti was one she'd set up personally, so she knows it was from her brother. Her eyes widen as she reads it though.

[Best Brother Forever! : So me and Willow had sex again.]

She's rather caught off guard if she's being honest.

[Oof. My condolences.] She says quickly. At first she wonders if that was the wrong thing to say, but the next text comes through fast.

[Best Brother Forever! : Yeah... She didn't want me to eat her out. She gave me a blowjob and we fucked.]

[Did she use teeth? I know how big your dick is, there's no way she didn't gag.] Jazz says, knowing that she could easily take his entire length into her own mouth easily.

[Best Brother Forever!: She wasn't... Bad. I did cum twice.] Jazz bites down on her lips nervously. She really doesn't want to lose him as a fuck buddy.

[Well, we both know I'd be better 😉]

[Best Brother Forever! : She... She definitely isn't very good at all of this. Willow told me she's willing to have sex every so often, but only for me. I…] She sees him start and stop typing a few times. She's about to interject when he responds.

[Best Brother Forever!: Don't get me wrong, I really like her. I think I love her, but... But we can keep... Doing stuff... Right?] Jazz has never felt so relieved.

[Of course! I was actually about to message you and see if you wanted to do a little bit of naughty stuff now 😘]

Best Brother Forever! is calling

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

"So tell your favorite big sissy all about your day?" Jazz asks him in a cutesy tone. Derrick takes a deep breath. "Ok, so she texted shortly after we stopped talking. She said she wanted to see me." Derrick explained.

"When I got over to her house, we sat down in her room and talked. She said that she knew she wasn't being very fair to my needs and that she was sorry." Derrick laughs softly. "Willow said that me and her could have sex every so often, but that she still didn't like it. So we went straight to kissing which was fine and all. But then I asked if she could give me a blowjob."

"Heh, if you wanted one, you should have asked last time you were here." His sister purs seductively through the phone. "What happened next?" Derrick continued. "She made a wince or something but then quickly agreed. So she pulled my shorts down and just... Gave me a blowjob." His sister laughs.

"That's it huh? Was it that bad?" He doesn't want to fully admit that it was bad; he did cum after all, but... "I - she just kept moving her head really. Nothing else. Her tongue got me there though-" His sister cuts him off.

"How much could she take?" Derrick really doesn't want to admit that either, but he doesn't have much of a choice.
"She barely put the tip in her mouth."
There's a slight pause on the other end of the line.

"Aww. I'm sorry baby. I wish I was there right now. You could jam all of that flesh rod of yours straight down my throat." The teen can feel his body starting to react to her words. "At least tell me she swallowed." Derrick fights back the disappointment of the evening as he presses on.
"No. As soon as I came she stopped sucking and it got on her face. She uh... She didn't like that." His sister just hums curiously.

"I mean, facials are ok. I prefer to swallow though." Jazz then chuckles evilly over the line. "Tell me bro, would you prefer to cover my face in your baby batter, or would you want me to swallow it all down?" Derrick ensures that his door is locked before he sits back down on his bed, pulling his shorts and boxers off.

"I'd want to do both." He says quietly. "I'd want to drown your face in my cum and then fuck your throat until it all comes out." He says. For a second, he thinks he may have gotten too aggressive. His sister just whistles.

"Fucking hell, I'm a bad influence on you, aren't I?" Jazz asks, a mischievous tone in her voice. Derrick licks his lips as he slowly starts to jerk himself off. "I can't help it Jazz, you just... Ugh you do things to me."

"I don't do enough to you if we're both being honest." Her voice sounds slightly off. He wonders if she's masturbating too.
"If you were here, right now... What would you do to me?" Derrick asks, his face red from embarrassment and from arousal. His sister laughs.

"Oh there's so much I'd do. First I'd probably let you have your way with my throat like you wanted." Derrick closes his eyes, letting only his hand and his ear guide him to pleasure.
"You'd really let me fuck your throat?" He asks. "Like, jam my dick down it until you couldn't breathe?" His sister moans. "Fuck yeah I would. What kind of sister would I be if I didn't let you use me whenever you wanted?" Jazz's voice then gets lower.

"You'd let me use you too right? Like, if I wanted to hold to down and just absolutely ravage you, you'd let me?" Derrick picks up his pace, going from slow to a more settled speed. His sessions never felt like this before...
"Yeah. Yeah, we can use each other whenever we want, right?"

"Of course!" Jazz moans out, rather loudly. "Of fucking course we can baby. I promise I'll be there soon. I want so badly to take good care of my adorable baby brother." Derrick licks his dry lips, as a moan escapes him.

"You're so much better than Willow sis. You're hotter, smarter and just..." He doesn't know where that comes from, but his heart does sting slightly at his words. Jazz sighs, in what he's pretty sure is pleasure.

"That's not a surprise. I'll bet no little girl like her can handle you sweetie. Only I can do that." Derrick chuckles. "Is it bad how much I want you sis? Because I want to fuck you so damn bad right now."

"It's only natural to desire the sexiest person D. It's why I want you. You and your fat cock." Derrick feels it. Knows it's coming.
"Sis, I'm so close. So damn close." He says. No. No, he begs. He begs her for the right to cum. To finish without her permission would be impossible.

"Me too baby. Cum for me, I'm cumming for you!" The orgasm hits him hard, and he has to aim his dick towards his shirt to soak up his sperm as he ejaculates over it. He hears his sister moan; he can imagine her shivering in pleasure, like when he was last over there, giving her an orgasm that shook her to her core
.
When he got the same type of orgasm
afterwards.

He calms down, breathing heavily but slowly into the phone. "Best. Phone sex. Ever." His sister says breathlessly. Derrick just shakes his head. "That was way more fun that I thought it'd be." He admits. Jazz hums in agreement.
"I don't care what happens, I'm getting over there ASAP." His sister promises him.
He hopes she's right.

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

Four days after their first long distance sex session, Derrick's parents decide to go out for their anniversary. Which, Derrick would like to point out, wasn't for another three months.
He had a feeling his sister had something to do with it, and that was confirmed later when she texted him.

[Sis: I got us the house to ourselves for a full day. Don't u wuv me? ]

He rolled his eyes, but smiled as he texted her back.

[I've always loved you dumbass. Now when are you going to be here? In a few hours?]

[Sis : U that desperate for some pussy bro? Damn keep your pants on, I'll be there just before they leave. Take a nap or sumfin.]

Derrick is about to text back, but as he does, he realizes that there's no telling how late the two of them WILL be up tonight.

[A nap might be a good idea actually. I'll see you soon?]

He doesn't get a response as he lays his head down. Derrick checks his phone periodically, but nothing pops up. Eventually, he starts to drift off…

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

A sensation is the first thing his mind notices. His ear feels oddly wet, and through the haze of sleep, he still feels it clearly - especially as a tongue runs along his ear. Derrick's eyes go wide and he nearly jumps, causing him to smack into someone.

"Ouch!" A female voice squeaks out. Derrick groans as his mind fully wakes up, and he's met with the sight of his sister rubbing her cheek.
"Fucking hell D, you have a hard ass head." Derrick rubs his eyes as he yawns. "Your fault for scaring me." He says, his voice only slightly touched by sleep. Jazz snorts. "I'm oh so sorry that licking your ear terrifies you. I'll make sure to never do it again."

His smart-ass sister says. He pushes her slightly as he goes to stand up, but she quickly pushes him back down. "Nope! Mom and Dad left a while ago and I told them I'd check on you every so often." Derrick looks up at his sister as she holds him down (with one fucking hand) and tries to glare at her. She only smiles.

"Ok, what does that have to do with the fact that I can't get up?" Jazz flicks his nose. "Well, since the two of them are already checked into a hotel nearby, and since YOU said I can use you whenever I want, I figure we can do some lewd shit."

Derrick snorts.

"You're the only person who says lewd unironically, you know that?" The teen says, as his sister rolls her eye. She unzips her jacket, throwing it on the floor nearby. Derrick groans. "Are you at least going to pick that up?" His sister answers him by flopping on the bed next to him. Figures. Guess he'll have to pick it up later.

"So, anything happen between you and Willow lately?" Derrick sighs, shaking his head. "No. Nothing since the other day." He says. "I'm glad that she loves me enough to try - which did I mention that? She said she loves me yesterday? - but it's all just so-"

"-Frustrating right?" Jazz says, her face just inches away from his. Derrick's about to kiss her, but she beats him to it. She starts off strong, her teeth biting at his lips carefully as her hand holds his head steady. The bites are rough, but not painful. If anything they only make everything hotter.

After what feels like years, but was probably seconds, Jazz rolls on top of him, straddling him as she keeps the kiss going. She forces her tongue into his mouth and wrestles his tongue down. He's not... Fuck, Jazz is so aggressive, unlike the first time they did this. He doesn't hate it though. Derrick won't admit that he likes it, but he sure doesn't hate it.

After his sister breaks the kiss, she leans on his forehead.

"Fuck this is nice... You really ok with me doing anything to you?" Derrick is puzzled, but it quickly hits him. "You mean you were serious?" He asks, and nearly punches himself as he watches her genuinely deflate. "Son of a bitch, I knew it was just pillow talk." Derrick quickly raises up as much as he can, and he ends up halfway sitting, halfway laying on his bed.

"No no! I just - you can do anything." He says quickly, and Jazz rolls her eyes. "I'm serious sis, I absolutely will let you do whatever you want." He says, his voice more firm than before. As soon as he notices her hardness going away, he pokes her stomach.

"That means I'm next though alright? I want that blowjob you were talking about." Jazz huffs, a small smile on her face. "All men want one. You're no different. So sad." His sister says, before she tilts her head slightly. “So then, I can do anything huh?” Jazz says mischievously, as she slowly pushes him back down to the bed. Derrick gulps as his sister eyed him like a hungry predator on the hunt.

“Yeah. Anything you want.” Jazz hums in delight. “Then I'm going to ride you. Hard.” Her hands grab his shirt and practically rip it off of him. Derrick's heart races. “R-really?” He asks nervously. Jazz just laughs as she tosses his shirt across the room. “Oh yeah. You're going to lay there and I'm going to take out all my sexual frustrations out on you.” Jazz takes her own shirt off and throws it on the floor, before she takes her pants off.

Derrick follows suit, though it does take some time to kick his shorts off while she's on top of him. Once the two are finally naked, Jazz grabs his cock and rubs it gently. “I've wanted this monster inside me since I first saw it.” Derrick chuckles. “What, years ago when you helped bathe me?” Jazz slaps his stomach, and rolls her eyes.

“Do you want to feel my pussy or not D?” She states blatantly. Derrick nods. “Yeah… Yeah. I want a better first time than I got.” Jazz smirks as she lines his dick up with her slit. “Oh Mommy is going to give her baby boy the best time ever.” A shiver runs down his spine, and as she inserts his dick into her pussy, he nearly cums instantly.

She was SO much wetter than Willow ever was. Her heat might even be more intense too, he's uncertain. What he does know is that this is a pussy a million times better than his girlfriend could ever even hope to have. “Holy shit this is amazing.” He says softly. Jazz just coos. “Mmh it's everything I wanted and more… Fuck I needed a dick so badly.” Well, she can have his anytime she wants.

He's not joking, this is absolutely amazing. And any lingering feelings of guilt he had towards cheating is flushed out as his sister begins to ride him. She slides up and down his cock so easily, unlike when he was with Willow. His dick is drowning in her pussy, the heat, the wetness, the tightness? It's unreal. He moans pathetically as Jazz leisurely rides him. She laughs.

“Damn D, you really are enjoying this aren't you?” Jazz bends her head back, and hums. “Can't say anything's different for me. Your cock is amazing.” Derrick chuckles breathlessly. “G-glad to be of service.” He tries to throw her a smile, but Jazz snorts. “You're not doing so hot, are you?” Derrick holds firm, and shakes his head. “I'll be fine. Just don't - don't stop. Please.” Jazz smiles.

“Why the hell would I stop? This dick of yours is top tier; I'm never letting it go.” Jazz then leans down, and pulls Derrick up with her left arm, holding him tightly. She pulls him up a bit until he's practically dangling in the air as she fucks him hard. “Hope you aren't planning on living alone in a few years. We're living together.” Derrick manages to put both of his arms around her, and gains some leeway. He begins to meet her thrusts, drilling into her.

“Oh fucking hell that's nice.” Jazz says, her breathing finally starting to match his. Derrick kisses her neck, her cheek and even her ears. “I agree… We're definitely living together. I want this pussy on call.” Jazz starts to laugh, but moans again. “What about your girl?” Derrick grits his teeth as he forces himself not to cum.

“I don't give a damn anymore. I don't need anyone else but you.” Jazz huffs out a breath of air. “Careful baby, Mommy doesn't need a relationship right now.” Derrick looks into his sister's eyes. Her face is… Is absolutely gorgeous. “I don't need one either. I just need you.” Jazz moans louder, and Derrick doesn't think he can take much more.

“I… Fuck, I'm not gonna last much longer.” Jazz slams down faster onto his cock, the sounds of flesh slapping together echoing in his room. “Then fill Mommy up! To the brim, don't spill a fucking drop!” The siblings kiss once more, and Derrick's will breaks. As her tongue slides into his mouth, Derrick unleashes one of the biggest loads of his life into his sister's womb. His dick throbs as her pussy squeezes and contracts around it, and be buries his head into her shoulder.

Jazz moans and her body shivers against him. “Fuck this is so good.” His sister says in a relived, blissful tone. Jazz falls forwards, and he slumps back against the bed as she lands on top of him. They lay there in post-coitus satisfaction. He's not sure how long they were there, but before long, he gets a text. The sound that plays is Willow's sound.

He looks at his phone, and snorts derisively. Jazz chuckles softly. “Willow I'm assuming?” Derrick chuckles. “Who? Far as I'm concerned i don't know her.” Jazz slaps his chest gently. “Now, to be fair, I taught you better then that.” Derrick shrugged. “We're better off separated. She deserves someone who doesn't appreciate sex and I need an insatiable sex queen I can worship everyday.”

Jazz gently scratches his chest, as she looks at him with a naughty grin. “Hmm I think I know someone.” She teases. Derrick rolls his eyes, as he rubs her back absent-mindedly. “No need Mommy.” He says sarcastically, before he turns his head. “I uh… I really like saying that.” Jazz just grins harder, as she starts to slide down further in the bed. His cock springs out from her pussy, and he hates the feeling of the cold air around him.

“Well, since you've been such a good boy for Mommy, I guess I should give you a reward.” His heart begins to race once more as he remembered her promise. His dick, defeated by her succulent pussy, raises once more as Jazz finally scoots down enough to see it. She starts to kiss and lick his erection, and Derrick sighs in pleasure as he lays his head back down.

“Mmh your cock tastes really good covered in my juices.” Derrick snorts. “Our juices comrade.” Jazz bursts into laughter. “Dude! Did you really - fucking shit!” Derrick joins her, but the two calm down quickly. “I really shouldn't suck your dick now. Like after that dumb joke I shouldn't fuck you ever again.” Derrick points at her. “But you promised, and my Mommy doesn't go back on her word.”

It feels a little awkward to talk dirty, but he guesses he did a good enough job when Jazz smirks back up at him. “Hmm I AM a good Mommy, and I would never leave my dearest baby boy alone.” She starts to kiss his cock once more, and Derrick loves it. Her lips are so soft, and inviting. After a few more kisses, she licks his tip greedily. “Ready baby? If you thought my pussy was good, I'm gonna mind break you with my throat.”

She gives him a single wink, before she puts her lips on his tip and slowly pushes forward. Her mouth definitely is different from her pussy, for the sole fact that her tongue instantly attacks his cock relentlessly. Even as she slowly engulfs his erection, her fleshy muscle slobbers all over him. First his tip, then his shaft. As soon as she fits half of him inside her mouth, she pulls back, and then immediately goes back down.

It's a deadly assault, one that makes him moan her name as she consumes his dick. “Jazz… Ja- Jazz.” He says breathlessly through his moans. She's just started and he's already light headed. His sister laughs on his dick, the vibrations doing things to him. She doesn't stop though, not in the slightest. Instead, she starts to go deeper every single time she goes down. Taking more and more of him into her mouth - and then he feels it.

Her throat. It wraps around his cock so tightly that it's almost painful. His sister continues to take more of him until finally her lips are touching his groin. She stays there for a moment as her throat swallows his dick - repeatedly. Derrick can't do much other than lay his head back down. As much as he wants to see this, he doesn't have the strength to keep his head up.

“Fuck, don't stop. Please don't stop.” He whines pathetically as his sister gives his dick the best pleasure he's ever felt in his life. She starts to move again, and every second his dick isn't in her throat is a second wasted in his opinion. Pretty soon everything else starts to fade - he thinks his phone rings, but he's not sure. He grabs it and yeah, it's ringing.

Willow. He can barely focus, but he does ignore the call. As his body is racked with pleasure, he manages to make one, single text.

[We're done. Bye.]

He turns his phone off and then tosses it somewhere on the bed. As he looks down, his sister has an eyebrow raised - while simultaneously giving him the best blowjob ever. “Ended it. Never need her again.” Is all he says, and he starts to pant as his legs start to spasm. “Fuck, I'm gonna cum… Please Mommy make me cum.” He's not even aware of how absolutely pathetic his voice sounds, but even if he was, he wouldn't care.

Jazz goes even faster on his cock, her tongue and throat destroying it. Finally, his first shot comes out. Then another. And another. He was wrong about before, THIS is the most powerful orgasm he's ever had. He's got no clue how much cum he shoots in his sister's throat, but after what feels like an eternity in bliss, his orgasm finally fades. Jazz plops his cock out of her mouth.

“Holy shit baby, that was amazing.” Her voice doesn't even sound hoarse. “Man… How much did you cum?” Derrick can't even talk right now. Jazz laughs softly as she climbs back up next to him. “You there, or did I actually mind break you?” Derrick makes a noise that could be considered a laugh. “I… Fuck. Almost.” Jazz gives him a wicked grin.

“Well we have all night. I'll break you before too long.” Derrick doesn't think he's ever heard a better sentence in his life.