Siblings... With Benefits? PT1 (Siblings With A Problem) (Patreon)

[I can't wait to see you tonight Derrick. My heart is pounding.]

The message came in a few hours ago and the teen - Derrick - can't stop looking at it in both excitement and nervousness. The young man was sixteen and looked the same, though he was a fair bit smaller than other boys his age. The dark haired boy almost jumped as a pair of hands covered his brown eyes.

"Guess who?" His sister's voice says from behind him. The teen clicks his tongue. "Santa Claus." He says, his voice as monotone as he can make it. His sister snorts. "Horrible guess little D. Try again." Derrick groans. "Stop calling me that Jazz." Jazz giggles as she takes her hands off of his face. "Well then Derrick -" She puts emphasis on his name "- I guess you don't want your loving sister to babysit you tonight."

Jasmine - Jazz - was his older sister. She was in college a couple of cities away, but the twenty-two year old was thankfully the person his parents hired to watch him tonight. His sister had green eyes and long, dark red hair. She was honestly a knock-out and it wasn't a surprise that the family had to - metaphorically of course - beat off guys with a stick when she was in high-school.

Derrick raises his head slightly to look past her, seeing no one outside his door. He stands up - upset that he barely reaches his sister's neck - and does a more thorough check behind her. Jazz raises an eyebrow, a mischievous smile on her face. "Oh, were you hoping to sneak out?" Derrick rubs his neck nervously. "Me and Willow were going on a date tonight. I think... I think tonight's the night." He says, his face heating up at his own words.

Jazz's smile gets wider and she elbows him playfully. "Aww, my baby brother is hoping to score tonight?" Derrick again does a quick peak behind her, but she waves a hand. "Mom and Dad already left. They wanted to get a head start to Chicago." See, this year was their parent's high-school reunion. He was lucky that they got Jazz to babysit him. He's supposed to be grounded after all, and he can't go on a date - and maybe lose his virginity - if he's grounded.

"Ok, ok that's good." Derrick says, as the teen sighs in relief as he sits back down. Jazz takes a seat on his bed across from him, and smirks at him as she holds her head in her hands. "So you got condoms?" He nods, opening a drawer on his desk. He digs around inside for a moment before pulling a pack out. His sister does a 'grabby hands' motion and he throws them at her.

She catches them easily. Jazz blinks for a moment, before whistling. "Damn, you sure these will fit?" His sister asks, raising an eyebrow. Derrick's face reddens, he knows it does. "Uh, yeah. I put one on. They're a perfect fit." Jazz shakes her head, the smirk now even wider across her face. "Fuck, I shouldn't call you little D anymore then." Derrick points at her.

"Call me big D and you're in for a world of hurt." Jazz huffs out in laughter. "Oh I'm so scared." She mocks, before suddenly snapping her fingers. "Oh yeah, I should like, be a responsible adult and set a curfew for you, right?" Derrick holds back his own laughter. "Please sis, you wouldn't know responsible if it slapped you in the face."

Jazz scrunches her face up. "How absolutely rude of you to say such a completely true thing." Derrick can't stop himself from laughing this time, and Jazz joins him. Once the two calm down, Jazz throws the pack of condoms back towards him. "Be safe, make sure to use those and be back around midnight." Derrick gives her a salute, and Jazz just blinks.

"I can't believe anyone actually wants to fuck you." And to be fair, he can't either. He didn't even think Willow actually wanted to date him at first. He assumed one of her friends had put her up to it a few months ago, when she went up to him and asked him what he was doing that Saturday. But now they've been dating and he's been so unbelievably happy.

Jazz smiles softly at him, before reaching over and flicking his nose. "You look ridiculous right now." His sister says playfully, and Derrick can't help but sigh dreamily. "I uh. Yeah, yeah I know. It's just... Willow is really awesome." He says, causing Jazz's smile to grow wider. "I'm really happy for you D. Just remember, nothing happens that either of you aren't comfortable with. Ok?" Derrick immediately nods.

"Of course! Of course, I just... I'm nervous as hell right now." He says, trying to ignore the butterflies in his stomach. His sister pats his bed, and he practically jumps off of his chair and sits next to her. "Alright, after making sure that you and her both want it, then you have to take it slow." His sister says, her tone actually rather serious.

"No one wants it over with too quickly, and guys especially have a lot of trouble lasting long their first time." Derrick heard that a lot. He always assumed it was true, but it's nice to get a confirmation. His sister rubs his back, and he leans on her shoulder. "So make sure that there's a lot of touching. A lot of kissing, that sort of thing. She might prefer something else but generally this is a safe bet for most people." Derrick nods as he stares up at his sister intently.

"What would you... Recommend?" He asks, only slightly nervous talking about sex with his sister. Jazz huffs out a laugh, and pats his back a little too hard. "You don't need my advice for THAT. Just, listen to her and let her lead. If she's too nervous, then gently reassure her and be a perfect gentleman." Jazz then turns her head to face him, and her smirk returns
.
"Unless she wants you to be a complete animal. Then you ravage the shit outta her." Derrick quickly turns his head, and his sister laughs again. "But odds are she'll want you to be gentle, so just do that unless she asks for you to be a bit more rough." Derrick takes the information in and swears to keep it in mind. Jazz pulls apart from him and yawns.

"Probably going to take a nap or something. If I'm still asleep when you leave, wake me up mister!" His sister yells as she walks through the door. "Ok! Love you!" Derrick yells, and gets only a cackle in response. Typical. Hasn't seen her in nearly three months and the first thing she does is give him sex advice and then leaves to take a nap.

He'll admit that he is a little hurt that she didn't want to hang out, but he gets it. She's a college student in her last year and he's only halfway through his Sophomore year in high-school. She's got better things to do than to hang around him all of the time. At the end of the day, he's just grateful to see her again, and hey, they've got two full days after tonight to hang out. He's sure he'll see her at least a little bit of that time.

Right now, he needs to figure out what to wear. He's got a date with one of the best girls on the planet after all.

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

Jazz briefly remembers waking up. She remembers her brother saying he's leaving and that he loves her. She's not sure if he said anything else or not, because she fell asleep again almost immediately afterwards. When she did finally wake up, she yawned loudly as she turned her head towards her bedroom clock. She rubbed at her eyes before it came into view.

11:26 PM.

Well, she had nearly a half hour before her brother got back. And she also slept damn near six hours. One more yawn happened before she kicked the blankets off of her and stood up stretching. After that, she debated about changing into something a bit warmer than her thin shirt and black panties, but decides against it. She'll probably go back to bed in a few hours anyway.

School had been really rough on her, and she was aching to get every bit of rest that she could during the next couple of days. She grabs her cell phone off of her nightstand and checks any new notifications while she heads towards the living room. Sadly, she's got nothing. None of the guys she's texted has gotten back to her which also serves to make her more irritated.

She doesn't even want a relationship! She needs a fuck buddy to help with her stress and damn it, not a single of her friends want to take her up on it? Jazz walked past the bathroom and poked her head in. She stared at her reflection, trying to see if anything was wrong with her. She was fit. She had a nice rack. She had a great ass. She was a total bona-fide hottie.

So why didn't any guy WANT her?

Ugh, she's so annoyed. She shakes her head, walking away from her reflection. She's got the house to herself and if no one wants to fuck her, she'll gladly handle that problem herself. She hopes that her brother is getting some action at least. Hopefully he'll be a little late in case her 'session' runs longer than she expected.

The young woman makes her way into the living room, and immediately syncs her phone and the TV up. It's been a long time since she got to watch some porn on the big screen. It's just as she's getting ready to start finding some good shit that suddenly the front door starts to jiggle. She whips her head around just in time to watch as her brother walks into the house. She quickly rids the screen of anything... Unsavory.

Her brother barely even notices her, however. Instead, he walks towards the hall. He's not... Ok, first off, he didn't need to be home for a half hour. Secondly, he is walking way too slowly for a teen that should have just lost his virginity. As upset as she is that her alone time has just been shattered, she's not an asshole.

"Lil' D?" She calls to him on her spot on the couch. Derrick does a half turn, apparently surprised that she's right there. But the confusion on his face quickly gives way to sadness. "Um. Hey Jazz. I'm back early. I'll just..." He points towards his room, but Jazz raises an eyebrow, before pointing next to her on the couch. Derrick looks back towards the hallway for a moment, before his head falls, and he walks over to her.

He flops down on the couch, and Jazz looks him up and down. "So what happened?" She asks, before poking his chest. "And tell me the truth." Derrick doesn't speak at first. Instead he just stares at the ground. "We... Well the date was fine." He finally says, before sighing. "Afterwards we went back to her house. Her parents both work nights so we were alone." Jazz nods her head slowly. "We went up to her room and started kissing. There was some touching and... And then we undressed." Jazz hates the fact that her body is reacting to his story.

It's not that she's overcome with sheer and utter lust, but fuck, she'd just been ready to finally have some much needed... Alone Time™.
"So I put my condom on and she was really nervous. I remembered what you said and I let her lead. Then we... Started I guess." Derrick mumbles the last part, turning his head away. At first, Jazz thinks she's going to have to talk him into spilling the rest of the story, but thankfully he continues.

"She really didn't like it. We tried slowly. We tried quickly. Every single time I got close, we had to switch things around." Derrick tried not to sound frustrated, but Jazz could tell he was upset. "Finally she just wanted us to stop. She wasn't enjoying herself and she absolutely..." Derrick sighs heavily, rubbing his eyes.

"She said she never wanted to try that again." Jazz couldn't relate. At all. Fuck she was fourteen when she lost her V card and she couldn't get enough of it. Still, not everyone is like that. So, she pulls her brother close and gives him a strong hug.

"I wouldn't worry too much. She was probably just as nervous as you, if not more." Jazz said, breaking the hug. "Give her a bit and she'll probably want to try again. I can't imagine this one awkward experience will ruin everything." Jazz says with complete confidence. Derrick seems unconvinced, but shrugs anyway.

"Maybe... I just. I just wanted to be alone." Whether or not he wanted that alone time to be just plain old alone time or Alone Time™ remained to be seen. However, Jazz's own fire is starting to fade, and if he actually doesn't have blue balls then maybe she can help take his mind off of it.

"So, you wanna go to your room or do you want to hang out with the coolest chick in town?" Jazz says, injecting some humor into her voice. Derrick manages to smile, and turns his attention to the TV. "What are we watching?"

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

The weekend comes and goes, and at first, Derrick decides to listen to his sister. Maybe Willow would come around. But she doesn't. Then a week passes. Then three. After a month, he decides to text her, see if she's feeling up to trying again.

[No Derrick, I meant what I said. I never want to try sex again. It was horrible and I felt sick the entire time.]

Derrick liked to think that he was a nice enough of a person. He wasn't going to pressure her if she didn't want sex, but that wasn't even the main issue. Not really. What was worse was the fact that a few weeks prior to what was supposed to be their first time, his girlfriend had explained how she didn't... Didn't masturbate.

And she didn't want him doing that either. She never gave him a good reason for her 'belief'.
Not masturbating was definitely a hard pill to swallow, but Derrick told her he wouldn't. And he has no problem not jerking off if she doesn't want him to. But... But if he can't jerk off, and if she doesn't want sex... He doesn't know what to do. Not one bit. So they text back and forth for a while. It becomes painfully obvious that she isn't budging on either stance.

If you really love me, you'll respect my wishes Derrick. I love you a lot, but I have my boundaries and I won't bend them. I'm sorry.

Derrick is stuck. Stuck between a rock and a hard place. He just... Just doesn't know what to do. On one hand, he's absolutely crazy about Willow. She's his first girlfriend, but she is also one of the nicest people he's ever met. He doesn't want this relationship to be ruined. He can handle this. He's positive he can.

…

But it's going to be hard. Really hard. He needs advice. His parents aren't going to be able to help - they never were the ones who gave him all the information he needed to know about sex - so that meant he only had one option.
It's going to be a long bike ride…

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

Jazz groaned as she checked her phone. It seemed as if she'd gotten a match on Tinder but they backed out at the last second. Why does everyone want a damn relationship nowadays? Where are the guys that just want to fuck? She has no clue how she can't find a casual sex partner, but she's certainly getting annoyed.

It's Friday, she had just done her last class, and she was now relaxing in her dorm. Her roommate, Nikki was gone. She'd apparently been sick or something and she was home now, her parents taking care of her as best as they could. She hopes her kinda-sorta-friend didn't catch Covid. That would suck. She decided to text her friend when suddenly, she received a text from her brother.

[Hey, is it fine if I dropped by?]

She... Huh. Ok.

[Are you all coming to visit?]

After a few seconds, another text comes through.

[No, I'm alone. I was hoping to talk to you. In person?]

Well she didn't have any plans for the night. Might as well have her brother with her. Then they can be bored together.

[Sure, you wanna spend the night? I'm bored as fuck.]

The next text comes in almost immediately.

[Is that allowed? I don't want to get you and your friend in trouble.]

Jazz snorts.

[She's home for the next week or so. She's got something. Maybe the big C.]

She waits for another text, but weirdly enough, a few minutes go by without a reply. Then, there's a knock on her door. She turns her head towards the noise, and then turns back to her phone. Jazz huffs, as she jumps up and rushes to the door. She swings it open and there, with his fist raised, is her little brother. She quickly grabs him, dragging the boy inside.

As soon as she closes her door - but not before checking the halls to see if anyone spotted them - she turns and glares at her brother. He turns his head quickly. "Did you ride your bike up here?" She asks. Thankfully he nervously laughs. "It's better than hitch-hiking?" Which yeah, ok, that's one worry she has off of her chest. Still though, she crosses her arms. She needs to be tough.

"Why would you ask me if you could talk, if you were already here?" Jazz asks. Derrick winches. "I know, I should have asked way sooner, but I had the chance to leave and I took it." Jazz can't stay mad at him for long, so instead, she groans. "At least tell me you told Mom and Dad a good excuse." Derrick smiles. "I told them me and Jimmy were gonna hang out. He said he'd cover for me so all I have to do is ask if I can spend the night."

At that, he frowns. "How much trouble will you get into if they catch me here?" Jazz waves a hand. "Practically none, you're my little bro! They'll just remind me of the dorm rules and we'll all go on our merry way." Or she'd get thrown out, but hey, it didn't matter that much.
College was a giant waste of time anyways if you asked her.

"Ok... So I'll text Mom and see if I can stay the night."

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

Well, Jazz has to admit, she's glad that her and her brother were able to spend more time together. The age gap meant that when he was younger, any time spent with him was basically just baby sitting and they really couldn't build up a meaningful relationship like that. At least in her opinion, it's hard to say you're friends with the annoying brat who you bring juice boxes to while also making sure they don't die.

But the last few years, they'd really gotten decently close. Even with her nearly two hours away. All of this was to say, she's glad that their mom said he could stay the night. Granted he was supposed to be a few blocks away, not a few cities. But what their parents didn't know wouldn't hurt 'em.

"So, you want to get the talking done first, or postpone it till later?" Jazz asks her brother. He puts his phone down, patting her bed and she playfully rolls her eyes as she sits next to him. "Alright so, you remember how you said that Willow would get over the way she's feeling?"
There's no fucking way.

"Well she hasn't. She said it was awkward and terrible and that she felt gross and all sorts of stuff that..." Derrick rubbed his face. "I don't think it was me but... But still, I don't know what to do." Jazz almost considered laughing. Odds are, young Willow was asexual. Or weird. One of the two.

But her brother was definitely upset, and the last thing he needs is to think that all of this is because of him. "Oh, D... Listen, I know that it's hard when you have a significant other who doesn't like sex, but -" Derrick shook his head. "It's not just that! It's... I haven't..." Oh. oh. Yeah. The other part.

Jazz sighed. She really hated this, but damn...
"Alright, so I've got a few questions." She says, as she turned herself in the bed, sitting Indian style in front of Derrick, the young teen mimicking her movements. "First, are you going to break up with Willow?" Derrick's eyes widened. "No! I can't, I still... I still really like her." Jazz sighs, before she shakes her head.

"Alright then. Second question. You and one other person live in a house alone. They don't cook you food. They don't want you to cook yourself food. What do you do?" Derrick scrunched his face up, a look of total confusion spreading across him.

"I... I'd go find food somewhere else?" As soon as he said those words, his jaw dropped. "Wait, you don't mean... You want me to cheat?" Jazz shrugged, a sympathetic look on her face. "It's either that or jerk off. You don't have to cheat." Derrick opened his mouth and closed it. Several times. After a few moments, he throws himself back on her bed. "Even if I wanted to cheat, who would I do it with?" Her brother asks, as he stares up at the ceiling.

"I... Willow was the first girl who ever actually talked to me for more than a few seconds." That's depressing. Like really depressing. She flopped down next to him. "Look, I'm not telling you to run off and get a second girlfriend, you just need to find someone willing to fuck." She states plainly. Heh, it's actually ironic in a way.

She wants someone to fuck and he practically needs someone to - Wait... No. Fuck no, that has to be the worst idea she's ever even thought of! She can't believe she even... Hmm… Derrick pokes her in the stomach, a look on his face. "What's wrong?" Jazz swallows air, before she sits up quickly.

"D... I might... I know someone you can fuck." She turned to face her brother. "Me."

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

Derrick blinked. There was no way he just heard that right. He sat up slowly, staring directly at his sister. She stared right back, nearly unblinking. Jazz's face was completely serious. "Jazz... What the fuck are you saying?"

He asks. Jazz bites her lip. "Ok, so lately - more than lately, the past few months - school has been kicking my ass. I've tried to get a fuck buddy or friends with benefits situation going, but I haven't gotten anything from anyone." She snorts. "Everyone I meet wants a relationship."
Derrick grabs at his hair.

"We - Jazz I - what the fuck?" He says again, because he cannot stress that enough. Jazz gently shoves him. "Dude, I'm saying that we can take care of each others urges. It's not like I'm saying we need to shack up and have kids!" Which ok, yeah that does make the situation slightly better, but - he can't believe he's even CONSIDERING this!

"It's still fucking wrong Jazz! On multiple levels! I'm barely sixteen and I'm your fucking brother." He cannot stress that part enough either. Jazz says, before taking a very, very deep breath.

"I know it's weird as hell, but I've been horny as shit for months now and not a single person is willing to help me out." Jazz says, and then pointed harshly at Derrick. "And if you don't want to jerk off and Willow won't fuck you, you're in the same boat as me. We need someone to release our urges on."

Something must be seriously wrong with Derrick for that to actually make sense. He wanted to come to Jazz for advice, not for this!
"How... If we do this, how the hell could we even look at each other the same way again?" Jazz chuckled. "I don't know, say hi when we see each other, talk about the weather." Derrick shakes his head.

"Jazz, I'm serious. If we do this, we... Fuck, I can't believe I'm even..." The teen really doesn't know what the fuck to do. Jazz moved away until she was on the other side of the bed.
"Forget it. It's a terrible idea. I'm just... Just so fucking horny lately and masturbating isn't helping." Derrick takes the time to look at Jazz. He can tell that she's frustrated. Upset.

... Son of a bitch.

"I guess we can try some things out. Maybe not sex, but..." Jazz looked back at him, a look he couldn't identify on her face. "Are you sure? I know it was my idea, but I don't trust my brain right now." Honestly, valid point. Not many people would recommend both cheating and incest in the same conversation. Still though... If this helps him to save both his relationship with Willow and help his sister out? He's up for it.

Kinda.

"So..." Derrick asks, his nervs suddenly very, very high. "What do we do now?"