Do You Trust Me? || JJ Maybank
mentions: john b, kiara, pope
requested: yes, i don’t have the exact request because it’s over on @maybanksbitch
summary: jj finds out you’ve never had sex. being the loving best friend that he is, he offers to show you what you’ve been missing.
warnings: swearing, underage drinking, mentions of peer pressure, fluff, protected sex (no glove, no love), very detailed and graphic fluffy smut
a/n: well, here it is! the end’s kinda shitty but honestly, i needed to finish this instead of going back to it on and off for a week. this is unedited because it’s long as hell and i’m lazy.
* not my gif. if it’s yours, please let me know so i can give you proper credit!
It was a lazy day at the Chateau for you and the Pogues. Everyone was debating on what to do for the day. John B suggesting surfing, Pope suggested fishing, Kiara desperately wanted to go swimming since it was blistering hot out. You and JJ were the only two who seemed keen on staying in. You’d rather sit around drinking and playing dumb games.
You sat with Kiara and John B in a half circle of old, stained lawn chairs. Pope and JJ were playing their favorite game that you called ‘Balance’. The one where you try and knock the other person off balance by pushing their shoulder. They were both holding strong, neither one leaning too far with each push.
Somehow you’d all gotten on the topic of hookups. JJ glanced your way and caught your eye for half a second. He’d been your best friend since you were in diapers, of course he knew you didn’t hookup with, well, anyone. The other Pogues didn’t know that though.
“Remember Fallon?” John B asked the group, sending JJ a sinister smile.
“Oh my God, she was obsessed with JJ!” Kiara shrieked through laughs.
You couldn’t help but laugh too, earning a glare from the blonde headed boy. Everyone remembered the crazy redhead who spent everyday at the Chateau looking for JJ.
“That was the first and only time we’ve ever had to lock the doors,” Pope recalled the memory, laughing when JJ shoved his shoulder harder.
“Oh, don’t think I don’t remember Crystal,” JJ teased, pointing a John B. “Or Brad,” he added and turned to Kiara with a raised eyebrow.
“God he still texts me,” Kiara muttered, shuddering at the memory of the Touron who practically fell in love with her last Summer.
“What about you, Y/N? We see the guys all over you at the parties. One ever stick?” Pope asked.
JJ’s jaw clenched at his question. He caught your eye yet again and almost fell over when Pope gave him a good push. You knew the blonde hated how guys treated you at parties. He was always there to get you out of those uncomfortable situations.
“Andrew,” you responded, feeling your chest tighten.
Your exboyfriend was a touchy subject. He dumped you after a year together when you still didn’t want to sleep with him. It never felt like the right time and at first he was okay with it, until he wasn’t. He tried to demand you sleep with him because that’s what couples do.
“He was your boyfriend, he doesn’t count,” John B said.
“I met him at a party though.”
“But he wasn’t just some hookup that became obsessed,” Kiara added.
“He was an asshole and friends with Rafe. Let’s leave it at that,” JJ intervened and gave up on the game with Pope.
The blonde walked over to you and instead of taking the empty chair between yourself and John B, he plopped himself right on your lap. You huffed and wrapped your arm around his middle when he leant back against you. You brought your bottle of Budweiser up your lips, giggling as some of the cold condensation dripped on JJ’s bare shoulder and he shivered.
The conversation changed quickly after that. JJ was protective of you and they all knew if they continued, they’d never hear the end of it. No one wanted to be on that end of JJ’s anger.
Eventually, it was decided that John B, Pope and Kiara would take the HMS Pogue our for a ride. Where they ended up was unknown, but they needed to get out of the house.
“Y’all coming?” John B asked as he stood up and stretched.
“Nah, I think we’re gonna hang back,” JJ answered for the both of you, though you weren’t complaining. You missed the days where it was just you and him. It would be nice to spend some quality alone time with your best friend for the first time in forever.
“Suit yourselves, you two have fun,” the brunette shrugged and went to follow your other two friends down the dock.
“But not too much fun!” Pope quickly called, pointing two fingers at his eyes then back at you.
JJ rolled his eyes and sent Pope his middle finger while you laughed. They all teased you two for being so close. They insisted that you were soulmates and just blind to it. You’d be lying if you didn’t feel some type of way towards the blonde, but you always pushed those feelings away. Soulmates could be best friends, right? They didn’t always have to be lovers.
“Okay, my legs are numb. Please get up,” you patted JJ’s stomach and let out a grunt as he stood.
JJ grabbed the chair John B had been sitting in and pulled it over so he could sit in front of you. He leaned forwards and rested his elbows on his knees, hands reaching out and grabbing your free one. He toyed with the bracelets on your wrist and tightened the ones that were coming loose.
You could tell his brain was at work with the way his crystal blue eyes glazed over. He wasn’t really even paying attention to what he was doing. You wanted to ask him what he was thinking about but also didn’t want to ruin the comforting moment. The rough pads of his thumbs started massaging gently into the top of your hand as his eyes flickered up to your face.
“I have a question. You don’t have to answer, obviously, but I’d like to know,” the blonde broke the silence with his soft voice.
You raised an eyebrow in response, giving him the indication to continue.
“I know you don’t hookup with people at parties, but I’ve also never heard you talk about Andrew in that way,” JJ started, causing your heart rate to increase. You knew where he was going with this. “Are you...have you-have you ever had sex?”
You mouth went dry at the blonde’s question. He may have been your best friend, but that wasn’t something you disclosed with him. Your friends may have been comfortable with expressing their sexual endeavors but not you. You let people think what they wanted and didn’t really care if it was true.
Your lack of response made JJ nervous. He didn’t want to pressure you into talking about something you didn’t want to. He couldn’t care less wether you had sex or not, he was just curious. “You can tell me anything, Y/N. You know I won’t judge you,” he added.
“I know, I know,” you told him, twisting your hand to hold the blonde’s. The tiniest smiled curled at the corner of his lips.
“I, um, yeah, no,” you stumbled over your words, cheeks heating up under JJ’s intense stare. “I’ve never had sex.”
You shook your head and let out a small laugh, avoiding his gaze and staring out at the water. “It never felt right with him. He dumped me because I wouldn’t,” you explained, feeling his grip tighten on your hand. “And I hate the idea of drunk, meaningless hookups too. It’s not like I don’t want to have sex, of course I do, just not like that.”
JJ’s bright eyes watched the way your index finger tapped against the neck of your beer bottle. His gaze trailed up your arm and stopped on your lips. He could see that you were chewing on the inside of your bottom lip. He watched your eyes flicker across the horizon, sparkling with the sun’s reflection. Your hair blew over your shoulder in the warm breeze.
“Do you trust me?” your blonde best friend caught your attention with his question.
You turned and met his stare, eyebrows furrowing a bit. You answered, “Of course I do. More than anyone in the world.”
“Would you let me make you feel good? Show you what you’ve been missing?” JJ was calm and collected on the outside, but on the inside his heart was hammering against his chest.
You didn’t know what to say at first. You’d be lying if you said you’d never thought about it. JJ was hands down, the most attractive guy on the island, in your opinion. And you knew him in a way other people didn’t. You didn’t know how you hadn’t already taken the dive and fallen in love with him sooner. With the way he was looking at you right now, it started to seem like a possibility.
The pads of JJ’s fingers started to ghost up and down your arm slowly, causing a shiver to run through you. He tilted his head and questioned you, “Y/N?”
You took a gulp of your beer to ease your nerves and set it in the cup holder of the chair. Breathing in deeply through your nose, your e/c eyes fell on his sapphire ones yet again. You head bobbed as you nodded and small smile spread across your lips, saying, “Yeah.. yeah, okay.”
JJ stood up and pulled you up as well with the hands holding yours. He interlocked you’re fingers and led you the short distance up to the Chateau. With each step your heart started to beat faster. You grasped the blonde’s hand tighter to try and keep yourself from shaking. He smiled over his shoulder at you as you crossed the threshold into the house.
The blonde’s hand left yours once you’d entered the spare bedroom. You turned and shut the door, flipping the lock into place just in case the Pogues came back during your escapades. You turned around and tried not to ogle at JJ who had shed his shirt in the few seconds you’d had your back to him.
A smirk curled on his lips as he sat down on the edge of the bed. You’d seen him shirtless thousands of times, but this was different. His eyes were a darker shade as he stared you down. A heat spread through your body as JJ used one finger to beckon you to him, a soft “C’mere” leaving his lips.
You took the few steps to the bed and stopped in front of him. His hands reached out and landed on your waist, pulling you in between his legs. He guided you down into his lap until you were straddling him. Your soft breaths mingled with his from the close proximity. Your hands found place on the warm skin of his bare shoulders.
“If it starts to be too much for you, just tell me to stop,” JJ’s voice was soft as he reached up and tucked your hair behind your right ear, “Okay?”
You nodded and gave him a small smile, whispering, “Okay.”
JJ’s pointer finger hooked under your chin and pulled your lips to his. He tasted like beer with a hint of mint and his lips were a bit chapped. He could taste your cherry chapstick and a soft hum left him. Your fingers slid their way around his neck and into the soft waves on the back of his head.
The blonde’s hands found your waist again as he pulled you closer. Your head tilted, deepening the kiss as you felt his tongue swipe your bottom lip. You obliged and allowed your lips to part, tongues dancing together. Your head was spinning. Never did you think you’d be kissing your best friend of sixteen years, nor that it would feel so good; so natural.
JJ’s fingers slipped under the material of your shirt, dancing against the soft skin of your hips. You pulled away from his lips, breathless. His eyes were soft as he gazed up at you and pushed his hands higher, your shirt moving with them. His hands sat on your ribs, thumbs stroking your skin.
“Can I take this off?” he whispered, eyes darting between both of yours, reading your expression to make sure you weren’t overwhelmed.
You bit down on your swollen bottom lip and nodded, holding your arms up as JJ removed the clothing. Your arms came back down, hands resting against his defined pecks as he took in your naked chest. It wasn’t unusual for you to not wear a bra. They were uncomfortable and itchy so you hardly ever wore one unless completely necessary.
“God, you’re fucking beautiful,” JJ breathed as his hands came up and cupped the mounds of flesh.
Your heart fluttered at the compliment, cheeks flushing and a smile spreading across your lips. JJ’s head dropped, nose nudging your jaw as you turned your head to the side. He pressed open mouthed kisses to your neck, sharp teeth gently nipping in certain spots. Your eyes slipped closed, breath hitching as he found your sweet spot and focused his mouth there.
His hands stayed on your chest, squeezing your breasts softly. He pinched one of your nipples between his thumb and pointer finger. On the other side his thumb brushed over the peaked nub with the lightest touch. A soft moan escaped your lips at the sensations he was bringing you. Your body was getting hotter, a tingling feeling intensifying between your legs.
JJ lifted his head when he was satisfied with the marks littering your skin. He brought his lips back to yours in a hard kiss, tongue immediately pressing it’s way into your mouth. His hands gripped your thighs as he turned the two of you abruptly.
Your back met the mattress and your lips seperated. He was settled between your legs, hands on both sides of your head. He took in the way your pupils were blown, parted lips puffy from the pressure of his own. Your hair was sprawled around you as short pants left your body. A smile tugged at his lips as he leant down to kiss you again. JJ was starting to think he didn’t care if you were the only girl underneath him for the rest of time.
His lips didn’t stay on your for long, wet kisses being pressed down your neck and chest. You watched him kiss his way down your stomach to the hem of your shorts. His eyes flickered up to yours in question as his fingers lingered around the button.
Your head moved in a single nod and that’s all it took for the boy to undo your shorts and pull them off, your underwear going with them. You felt shy under JJ’s hungry gaze as he dropped your clothing onto the floor. Your thighs went to clamp shut but he put his hands on your knees to stop you.
“Is it too much?” the blonde asked, staring up at you.
“No, no,” you responded quickly and smiled softly, putting a hand over the side of your burning face. “S’just no one’s ever seen me like this before.”
JJ smiled at you and glided his hands up your thighs, leaning down to kiss the inside of your knee. He started to trail his lips up the inside of your thigh slowly, eyes still locked on yours. “You’re beautiful,” he told you again against your skin.
You bit your lip to hide your grin and shifted as he pushed your legs open wider. JJ laid down flat on his stomach in between your legs, nearly moaning as his painfully hard cock brushed against the mattress through his board shorts. His eyes flickered up to your face and remained there as he leaned forward and tested the waters, tongue dragging through your folds slowly.
A soft gasp left your lips at the foreign feeling. The bottoms of your feet pressed further into mattress. JJ repeated the action a few more times, the drag of the velvety muscle against your clit sent jolts of electricty through your body. His middle finger came proding at your entrance, slipping in with ease.
He pumped the single digit and slid his ring finger in beside it after a minute. A soft noise of discomfort left your parted lips. JJ wrapped his lips around your clit and sucked softly to distract from the feeling. There was no stopping the smirk on his lips when a sharp moan left you as he curled his fingers. His tongue flicked at your sensitive bundle nerves and your fingers grasped onto the sheets tighter, another moan leaving your mouth.
“Ah, shit,” you hissed, face scrunching in discomfort as he added a third finger.
JJ looked up at you and then focused his mouth on your quivering inner thighs, trying to ease the pain. “I know, I know. But I’ve gotta make sure you’re good ‘n stretched so it’ll hurt less,” he cooed.
You nodded twice and breathed slowly as you willed your body to relax. JJ’s mouth came down and found your clit again. He swirled his tongue as he began pumping his fingers again. He was pleased to hear your whimpers turn back into moans.
The blonde pulled away when he figured you were stretched enough. He wanted nothing more than to have you cum around his fingers, then his cock, but he thought it might be too much for you. A soft whine came from the back of your throat when his fingers left you and he chuckled.
JJ came to a standing position beside the bed and undid the strings on his shorts. He pushed them down and kicked them off, dick standing hard and proud once it was free. He didn’t miss the way your eyes widened and you nervously swallowed as you eyed him.
“I know it looks intimidating,” JJ started, feeling proud that you were impressed. “But you’ll be okay.”
“JJ, you’re gonna rip me in half with that,” you stated, completely serious.
A loud laugh came from the blonde as he bent down and grabbed a condom from the box stored under the bed. He stood back up and crawled onto the bed, silver foil packet clutched between his fingers.
“That’s not gonna happen, baby, promise,” the nickname directed at you rolled off his tongue and your stomach flipped. You’d always teased each other with names like that but it was different in this sense.
You watched silently as JJ ripped open the condom package. His hands shook the slightest bit as he rolled it on and let out a puff of air from the little contact his erection received. He shuffled closer to you on his knees and hooked his hands under the backs of your thighs, pushing them towards your chest. You bit down on your bottom lip as you felt the head of his cock brush your entrance.
“Ready?” the blonde asked, bright eyes meeting yours. His thumb rubbed gently on the back of your thigh as if to tell you it’s okay to back out now.
You nodded in response and let out a deep breath through your nose. Your hand reached down and gripped onto JJ’s wrist that had your leg held back. He gave you a small smile then looked down between your bodies, free hand helping guide his length into your entrance.
Your mouth fell open, hand squeezing onto his wrist tighter as he pushed into you slowly, inch by inch. JJ’s jaw clenched as your pussy gripped him like a vice. He put the hand that was free on your hip and paused.
“Relax, Y/N, you gotta relax,” he groaned out, resisting the urge to plunge into you like he was used to.
“I’m trying,” you whimpered, tears stinging the corners of your eyes.
“Breathe,” JJ told you, “Breathe through it, baby.”
You sucked in a shaky breath through your nose and let it out your mouth, repeating the action until your muscles started unwinding. The muscular boy above you huffed when he felt you unclench around him. He pressed forward again until his thighs were pressed against the back of your own.
He stayed like that, letting you adjust, drawing soothing circles against your skin as he waited. He looked up to your face and saw you had your eyes clenched shut. His hand came up and caressed the side of your face, thumb brushing underneath your eye.
“You okay?” he asked softly.
You swallowed thickly and opened your eyes to look up at him. He was staring down at you in worry but his eyes were filled with nothing but adoration. The whole scenario was making your head spin.
You were laying there, stuffed full for the first time with your best friend’s cock. What?
“Y-Yeah,” you managed to respond, feeling breathless under his stare. “You can move.”
JJ put the hand that was on your face beside your head, leaning his weight on it as he hovered over you. He pulled out slowly then pressed back in. He pushed your leg back farther with the other hand and thrust his hips again.
It was an agonizingly slow pace, you knew that much, but he was taking his time with you and you’d never been so grateful. Anyone else probably wouldn’t have taken care of you the way JJ was. You couldn’t picture losing it to anyone else in that moment. He was the closest friend you had. He was your person.
JJ’s eyes moved between your face and down to where your bodies met repeatedly. He was entranced by seeing your tight walls grip him so deliciously, but also needed to make sure you were okay. He smirked slightly when he saw the crease inbetween your eyebrows disappear with each thrust and soft, pleasured noises started to leave your lips.
The blonde boy began thrusting faster, unable to contain the low groan that bubbled in his throat. Your hands moved up onto the back of his neck and wrapped around his bicep. Your blunt nails dug into his skin as you moaned louder, head tilting back and pressing into the mattress.
JJ readjusted his position, dropping to his elbows on both sides of you. You hiked your legs up on his hips, breath catching in your throat at the new angle. His cock made you feel so full, brushing against your g-spot with each stroke.
“Fuck, J,” you moaned out, fingers tangling in the hair on the back of his head.
The feeling JJ got when looked at you underneath him and you moaned for him was indescribable. A heat flooded his whole body. He wanted to be the one who made you feel good; the only one. The thought of anyone else seeing you like this infuriated him, but the feeling of your hand tugging on his hair brought him out of the trance.
“You’re doing so good,” he muttered, bending his head down to press kisses to your neck, “so good.”
JJ’s thrusts got harder, the head of his cock pressing up against that spot inside of you that made you see stars. You cried you, gripping onto him as he kept the pace, his mouth working more marks into your skin.
He didn’t think he could last much longer, not with how tight your pussy clenched around him every time he hit your spot, moaning his name in ear. He pushed his weight onto one arm and slid the other down between the two of you. He lifted his head and watched as your mouth fell open as soon as his fingers made contact with your clit. He rubbed in quick figure eights, working you up to your high.
“O-Oh shit,” you cursed, nails scratching against JJ’s shoulders as your back arched off the bed.
Your whole body was tingling, a tightening feeling coiling in the pit of your stomach. The rhythm of JJ’s thrusts never faltered. The sinful moan that tore through your throat as you came was music to the blonde’s ears.
“Fuck,” JJ gasped as you clenched around him, following you into euphoria with a moan of his own.
Your thighs shook, still hooked around his waist as you came down from your high. Your arms were still wrapped around his shoulders as he buried his face in the crook of your neck. The two of stayed like that for a few minutes, letting your heavy breaths return back to normal.
Eventually, JJ pulled out of you slowly, causing a small hiss to leave your lips. He climbed off the bed and went to dispose of the condom in the bathroom trash quickly. When he entered the room again, you were climbing under the covers, wrapping yourself in the blankets. You had a hazy look in your eyes and a dopey smile on your face.
“Was it everything you thought it would be?” JJ asked as he climbed under the covers beside you.
The two of you faced each other on the bed, heads nuzzled against the pillows. You hummed softly, eyes fluttering closed as exhaustion washed over you.
“Better,” you muttered in response, cracking your eyes open to peak at your best friend once again.
He was staring at you, soft smile adorning his lips as his eyes trailed over your face. He scooted closer to you and wound an arm around your waist. He pulled you against his chest and pressed a chaste kiss to the top of your head. His fingers trailed lazy patterns up and down your spine, lulling you into the best sleep you’d ever have.
“I love you,” JJ whispered, knowing you were deep in dreamland by now.
The blonde didn’t sleep, he just laid there and held you, replaying what just happened in his mind over and over again. He saw you in a different light; a light that he never wanted to burn out. Laying there holding you, butterflies fluttering happily in his stomach, all he could do was smile.
The two of you were definitely going to be having a long conversation on how to move forward when you woke up.