Tonight - Jack Gilinsky First Time Smut
boy/character: jack gilinsky
authors notes: um this is my first smut so idk what to tell ya I’m very new at this…
“I don’t want to get hurt”
“I’m not gonna hurt you.” The characters murmur sitting inside the car.
“You know I’d never hurt you, right?” Jack says moving his large hand up and down my leg slowly. The two of us were tangled together sitting on our shared couch as “Struck In Love” plays on the flat screen. We had been together for nearly 10 months and Jack was still as sweet as he was on the first date.
“I know that.” I smile up at him, his brown eyes sparking like his million smile.“Good.” Jack says placing a kiss on my temple. I smile at him, watching as he turns his head back to the movie. I sigh running my fingers through my thick hair. I smirk slightly before I place my hand on Jacks upper thigh and kiss his cheek. I feel his features stretch into a smile before I continue my kisses down his defined jaw. “Babe,” Jack groans fidgeting in his spot on the leather couch, “I’m trying to watch the movie.” He says struggling to finish his sentence. I pull away from him and stand up from the couch turning to stand in front of him.
“(Y/N),” Jack says annoyed before I sit on his lap batting my eyelashes, “wh-what are you doing, baby?” I ignore his question and connect my lips to his. His brown eyes flutter shut and his large hands grab my back holding me on his lap. Jack rolls us over laying me down on the couch him hovering over top of me. We break the kiss and I see Jacks precious smile and his perfect ruffled hair. “You are so beautiful,” Jack smiles moving my hair from my blushing face, “and distracting. I need you, now. Let’s go upstairs.” He stands up, holding out his hand and I take it. We walk up the stairs and my stomach begins to turn. Is this really happening? Tonight? Am I really going to lose my virginity tonight? I think walking up the endless stairs. Jack opens our bedroom door and we walk inside, sitting on the bed.
“Look-I don’t want to hurt you.” Jack mumbles playing with his fingers, “I love you so much and if I know that I hurt you-I-i don’t think I could live with myself. (Y/N) you’re my whole world.”
“Jack-” I cut him off by grabbing his hands, “I love you. I want this. I would rather lose it to you then anyone else on this planet. I’m ready.” It had always been a discussion in our relationship, I never wanted to because I was terrified of what would happen. But I knew that Jack was the one, and tonight was the night.
“Are you sure?” Jack says turning to me his dark eyes lingering on my features. “110% sure-” I barely finish my sentence before I feel Jacks smooth lips on my neck. He picks me up from my bed by my butt and he gently places me down on my back before breaking the kiss to place a delicate kiss on my nose. “I love you, (Y/N).” Jack says quietly and I smile.
“I love you, Jack.” I say in the same quiet tone before Jack moves his hand to the bottom of my black t-shirt. Quickly, Jack takes the shirt off over my head and tosses it behind him. He moves his lips from my lips to my neck and my breath hitches. I tug my lip between my teeth, watching him stare at my exposed skin. His brown eyes gaze upon my black lace bra and I mentally thank myself for wearing like bra Jack bought me for Valentine’s Day.
“I like this,” Jack says his lips centimeters away from my chest, “where you get it?” He says cocking an eyebrow. His plump lips move down between the valley of exposed skin on my chest and I feel pressure between my legs.
“Jack-” I moan, “your sweatshirt.” I say clawing at his clothes.
“You want me to take it off?”
“Yes, please.” I say and Jack follows my wishes. Jack’s sweatshirt is tossed across the room where my shirt is.
“I like this on you,” his long fingers trace the outside of the thin bra, “but it would look better on the floor.”
“Cliché.” I joke and Jack smiles before bringing me forward unclasping my bra and dropping it to the ground.
“So beautiful.” Jack comments before placing a sweet kiss on my forehead. He licks his pink lips before kissing his way down to my chest. I squirm underneath him wanting his touch somewhere else. His lips kiss up and down my chest, before his bottom lip drags over my left nipple. And his hand grabs my right breast. His fingers massages my right breast while his mouth works on the other. His teeth gently graze my nipple and I moan in pleasure.
“J-Jack.” I whimper and he switches his mouth to the left and his right hand to my other breast. His mouth moves away from my chest and kisses his way down to my pant line. His eyes flicker up to me and a smirk catches his lips. “May I?” He asks and I’m too overwhelmed to answer so I just nod my head quickly. Jacks thin fingers pull my sweatpants down and they pool around my ankles. Jack gently tosses them aside before he blows lightly into my covered core. His hands wander up my legs hooking onto my hips. His dark eyes catch my light ones before he places small kisses on the inside of my thighs. Jack hovers over me placing a sweet kiss on my lips and I return it. He smiles one last time before going to the end of the bed and hooking his fingers around my underwear and tugging them down.
“Yes.” I nod vigorously. His lips attach themselves to the inside of my thighs once again before slowly making their way to my core. His tongue licks my slit before he sucks gently causing a wave of pressure to rock through my body. His tongue pulses up and down my slit again and his eyes look up to meet my graze. I throw my head against the pillow in pleasure when I feel Jacks thin fingers graze the outside of my cult. Slowly, he inserts one finger and I feel my core wrap around him. “Jack.” I pant and Jacks head snaps up to look at me. “Wait are you okay?” He says about to pull out.
“Yes,” I sigh heavily, “it feels amazing.” Jack smiles to himself before moving a second finger in and moving both in and out. His tongue still works at my slit as his fingers move in and out causing my back to arch in pleasure. He takes his fingers out and licks them clean. I sit up and pull him on top of me before I tug his tight pants off, chucking them onto the floor. “(Y/N),” Jack hesitates, “this is supposed to be about you.”
“I don’t care,” I smirk, “I gotta learn at some point right?”
“You make a very valid point, baby.” He says and I smirk up looking through my lashes. Jack lays down on his back propping his bare chest up by his elbows. His large erection clearly visible through his thin boxer briefs. Slowly, I crawl over his legs until I’m eye-level with his boxer waist band. My teeth grip the elastic waistband between my teeth and drag down. “Are you sure you’ve never done this before?” Jack groans as I smirk up at him. I hook my fingers around his boxers and pull them the rest of the way down. I watch intently as Jack’s bulge moves from the tight fabric of his Calvin’s to the brisk air. He was huge. How was I, supposed to fit that…there? I subconsciously ask while swallowing the nervous lump in my throat. “Babe,” Jack notices my sudden nerves, “we don’t have to. I love you no matter what, it doesn’t matter if it’s tonight or tomorrow or never. I love you (Y/N).” He finishes and I feel a rush of confidence and I nod with a smile. I take a deep breath and wrap my hand around his shaft. Slowly moving up and down I notice Jack’s head fall back and a smirk creeps onto my lips. Moving faster I continue to pump his cock before I kneel down and lick the head of his hard member. I slowly lick the shaft up and down before taking the throbbing cock into my mouth. I hallow my cheeks and suck lightly. “Damn,” Jack moans, “(Y/N). Oh my god.” I quietly chuckle to myself before repeating my actions.
“Fuck baby,” Jack runs his hand through my hair before tugging at the ends, “you are so hot.” I batt my eyelashes at him and I watch as his bottom lip gets pulled between his perfect white teeth. God that is so hot. “(Y/N), I’m gonna cum.” He moans and I pull away and Jack pulls me to his chest. “I love you, (Y/N).”
“I love you, Jack.”
“You ready babygirl? I don’t want to hurt you.” Jack farrows his eyebrows.
“I’m ready, Jack.” I smile and he places a sweet, gentle kiss on my lips. Jack flips us over and kisses down my chest, again, to my core. The pressure between my hips is stronger then ever and I feel sick. The nerves of excitement and anticipation are ridiculous. I want this, I need this. I’m ready. I tell myself over and over knowing I am but I can’t admit it.
“(Y/N),” Jack says breaking me from my thoughts, “are you okay baby?” I nod with a smile before I feel Jacks two fingers pulse in and out while his other hand pulls the table drawer open grabbing around in the draw. After few seconds he pulls out a condom and put the wrapper between his teeth and rips the package open. Slipping the silky condom over his erection he licks his fingers clean and hangs above me his member lined up with my core. “Are you ready babygirl?” Jack says nervously.
“For the millionth time, yes.” I smile wrapping my arms around Jacks neck bringing his tempting lips to mine. Slowly, he pushes his cock into my slit and I separate our lips and throw my head back against the pillow. He adjusts himself before asking if I’m okay again. I nod at the unusual feeling and Jack starts to rock his body in and out. “Oh my god-Jack!” I claw at his back and Jack moans.
“Damn baby,” He bites and sucks on my collarbone, sure to leave a mark, “you’re so tight.”
“Jack-” I arch my back to wrap my legs around him and he pumps in and out faster. It was a weird feeling that was just indescribable. New but normal and strange but certain.
“Are you okay?” Jack asks kissing the corners of my glossy eyes.
“Yes,” I swallow looking into his deep brown eyes, “oh my fuck-” I moan and I catch a smirk on his face. I notice the beads of sweat on Jacks forehead has he moans my name sensuously.
“D-deeper!” I yelp and pull Jack closer by his muscular sides, “right there."
"That’s where you like it, baby?” He kisses my chest sloppily while I nod. “God you are so hot.” He says kissing my neck leaving hickeys here and there.
“Jack-” he moves rapidly almost at his climax, “I’m gonna cum.” I squeal under him and he brushes his nose against mine.
“It’s okay babygirl, whenever you’re ready princess.”
“Now?” Jacks strong hands find mine and they intertwine both laying by my head.
“Now.” Jack calmly says and we reach our climaxes together, my toes curling and my vision hazy.
“Jack, I-” I barely get out before Jack automaticity looks guilty. “Did I do something wrong? Are you okay? Oh god I hurt you didn’t I?” Jack stutters while pulling out of me and throwing the condom in the trash.
“Jack,” I grab his face and he lays down beside me, “you were perfect. It was perfect. Everything was perfect. I love you.” I smile as Jack pulls me into his bare chest our sweaty skin sticking together like pieces of a puzzle.
“Oh thank god, I thought I fucked up!” Jack sarcastically laughs and I slap his chest, “but really (Y/N) how are you? You feel okay?” How was I? It was a weird question, I was sore for one thing but I knew tomorrow would be worse for sure, and I knew that I felt amazing. Relieved almost.
“That was amazing. I’m so amazed. I-I don’t know what to say.” I say at a loss for words.
“So it was good then?” He asks raising one of his perfect eyebrows.
“Perfect.” I correct him.
“Good,” Jack grabs the blanket from the end of the bed and tosses it over us before turning the TV on, “I love you more then anything (Y/N).”
“Thank you for everything, tonight was amazing, Jack. I love you.” We both smile Jacks eyes flickering down at mine and he presses a soft kiss to my forehead before my eyelids become heavy. I feel myself drift off into sleep but before I do I hear Jack mumble, “You are all I ever wanted (Y/N).”
A/N: Oh wow ok wow my first smut what am I. This sucks and I apologize. Forgive me god.