Omaha Squad Smuts

Jack Johnson: Sister's Boyfriend

-Background-
You're in a whole lot of trouble after you lose your virginity to your older sister's boyfriend.
-Your POV-
"Hey", Jack slurred as he opened the door. Is he drunk? "Hey, Jack. Where's y/s/n at?", I try to peek my head in the apartment, but he moves his body to block my view. "She's not here. Why?", he says while holding onto the door frame for support. "I needed to drop her clothes off. I borrowed a few things the other day. Do you know when she'll be back?", I try to make this conversation quick. I can tell he's been drinking all day, no telling when she left. "Probably in a few hours...", he trails off, "Why don't you come in and chill for a while?" "No, thanks. I really should be getting home", I try to think of an excuse, but fail. "Oh come on. Have some fun", he puts his arm around me and pulls me in. I shuffle my feet in and he sits on the couch, forcing me to sit next to him. We sit in an awkward silence for what seems like an eternity, until he speaks. "So do you have a boyfriend?", he questions. I look up at him, confused, but his attention is directed towards the tv. "Um... no. Why?" I don't understand why he would ask such a weird and personal question. "I don't know. I'm surprised", he responds, still fixed contently on the tv screen. "Why is that surprising?", I question. "You're hot... and your body is nice so I thought someone would've cuffed you up by now", he shrugs. How in the fuck can he be so nonchalant about this conversation? He's perfectly fine flirting with his girlfriend's little sister. I'm still in high school and he's already 23. I don't understand. My heart is doing flips, and I instantly feel guilty. I shouldn't be swooning over the fact that my sister's boyfriend is flirting with me. I clear my throat and squirm around in my seat. "Jack?" "Yeah, babe?", he responds, this time looking at me. His eyes are dark and they have bags under them. How can someone look so exhausted and hot at the same time? My stomach is doing flips at his pet name for me. I can't even find the words to respond. He moves towards me and lays his lips on mine. What the fuck? Is the really happening right now? Am I really doing this? His lips feel so soft. He licks my bottom lip, silently asking for entrance, but I deny him. I pull away and my breathing is uneven. He smirks when he sees the redness on my cheeks. "Why d-did you do that? W-we aren't supposed to b-be doing that", I stutter. I mentally slap myself for sounding like such a dork. He laughs lowly at my words. "You didn't like it?", he questions. He lays his hand on my knee, rubbing softly. "I-I don't know... I've never kissed someone before", I admit. Why would I tell him that? Why would I reveal that I'm a senior in high school and I've never had a boyfriend, or kissed anyone, and that I'm still a virgin. "What?", he shakes his head in disbelief, "That was your first kiss?" He laughs and I feel uncomfortable. "Oh baby... you have a lot to learn before college. Let me show you, princess", he says before grabbing my hand. He pulls me to the bedroom and tells me to remove my clothes and lay on the bed. I hesitate at first, but when he pulls his shirt off to reveal his abs, a wave of tingles rush to my core and I obey his demands. Maybe we won't get caught. I pray we won't get caught. Was he going to fuck me or are we just going to make out? I would accept either. He goes to the bathroom and comes back with a tiny silver package- a condom. He sits on the bed and pulls his pants off, along with his boxers. "Come here", he motions for me to kneel in front of him. I assume I'm going to give him head so I put my hair in a loose ponytail. I'm a virgin, but I watch porn, so I know exactly what to do. I take his already-hard member into my hands and pump him a few times. He stares at me, intrigued by my actions. I take his tip into my mouth and suck gently. "Fuck", he breathes. I start to bob my head and I hollow my cheeks out for added pleasure. His breathing gets heavy as I go faster. "Stop... stop. I'm close", he says in a hurry, while grabbing my arm. I wipe my mouth of the surrounding saliva and stand up. He lays back, "Ride me." "I can't... I mean... I don't know how", I say nervously. "Oh shit... my bad. I forgot", he sits back up, "Here, um lay down. I'll take care of things." My heart races at his gentle words. I lay down on my back and allow him to hover over me. He rolls the condom on and I start to get worried. Should we really do this? What if we get caught? As if he's reading my mind, he speaks up, "Are you sure you want to do this?" All I can do is nod. He positions himself at my now soaking entrance. He slowly pushes in and I bite my lip as a tear slips out. I didn't know it would hurt this bad. I kind of don't want to do it anymore, but I can't back out now. "Are you ok?", he looks up, "Fuck. I'm sorry. I'll stop. I know it hurts." He tries to pull out, but I lay my hand on his back and apply pressure, letting him know I'm ok with his actions. I take a deep breath and he pushes the rest of himself in. He pauses, allowing me to slightly adjust to his size. After a few moments, I tap his back and he starts moving. He thrusts slowly, making sure not to hurt me. I moan, barely audible. I reach down and rub my clit, as I always see in the pornos. Sure enough, it adds tremendously to the pleasure. I start moaning and he increases his speed. The sound of his skin slapping against mine and our moans is the only thing I can hear. I feel a bubbly sensation build in the pit of my stomach. "Fuck, princess... you're so fucking tight", he moans in my ear. With my free hand, I tangle my fingers in his hair. "Jack... I think I'm close", I whisper as I keep rubbing my clit at a steady pace. He nods his head and thrusts even faster. My vision goes black as my orgasm washes over me. My legs shake and I moan uncontrollably. My walls clench and contract around Jack, causing him to fill the condom with his warm liquids. He collapses next to me, both of us attempting to catch our breath. "That was amazing", Jack breaks the silence. I can still smell the alcohol on his breath. "Mhm... thanks", I say awkwardly. "You're so tight. Your sister isn't as tight as you. I might have to swap yall out." I get up and start putting my clothes back on when I see someone standing at the door. Fuck. It's my sister. "Y/n don't bother trying to talk to me... and Jack... you can go fuck yourself. Both of you deserve each other", she says softly, her voice is hoarse from the tears building up. I'm at a loss for words. I have no idea what to do. I turn to Jack and he looks at me, unbothered. "You aren't freaking out?", I question, curious as to why he has no reaction to her presence. I hear the door slam and I look at him, still waiting for an answer. He takes a deep breath, "She cheated on me the other day. I don't feel bad for her." I'm shocked. My sister has always talked down on people who cheat, and for her to become one herself is unbelievable. I sit back down on the bed, trying to figure out how to explain all of this to my parents. Jack scrolls through his phone, not even bothering to put his clothes back on. "Is it ok if I stay here? I don't want to go back home to my parents", I ask Jack, hoping he'll be ok with it. "Yeah. Stay here as long as you need", he reassures me. Fuck... this is going to be a huge mess. At least J is here to support me. I guess being with him wouldn't be so bad. I can't imagine why my sister would cheat on him. He's so handsome and he fucks good. I forget about my problems for the time being and enjoy Jack's company.