> Truth or Dare
Pairing: Bear Bailey x Fem!Reader
Warnings: SMUT, i believe in bottom bear sorry hes lowk pathetic in this
A/N: holy moly my first Bear draft got way much more attention than I thought it would agh. I also just want to note that just because I write for Bear does NOOOOOT mean I condone his actions in the movie!!!!!! This is strictly fictional and js cuz i think michael johnston is cute :p
Ian's house felt like pure hell for Bear Bailey right now; obnoxious music blasting through speakers, the smell of alcohol lingering throughout every surface of his place. Bear hated large crowds of people, he didn't understand how he ended up best friends with the one dude that loved to throw parties more than anything in the world. It wasn't his usual scene, but there was one motivator for coming to these. You.
You were everything to Bear, after spending so many months pining after Nikki who didn't give him the time of day. You had appeared into his life like an angel. The sweet girl who managed to land a job at Cassel's after just moving into town, you were sweet and kind to him like it was the most natural thing in the world. Bear fell for you, hard. He was even more grateful when Ian had decided to officially indoctrinate you into their little group.
Bear returned from getting a drink to where the four of them were all seated--Nikki, Ian, Sarah, and Y/n. The party was still as loud and claustrophobic as usual, but within this small circle it made Bear feel a little safer. Ian perked up when Bear came back, instinctively wrapping an arm around his shoulder with a smug grin on his face.
"Perfect timing! I wanna play drunk truth or dare." Ian beamed, cut off by Sarah's scoff.
Sarah, who looked unimpressed by the idea, shook her head.
"That is such a childish game," Sarah rolled her eyes.
Bear was ready to agree before he was cut off--
--"Aw, come on, it'll be fun!" Your voice cut through like a symphony, nudging Sarah with a playful grin. Bear's heart nearly stopped when you turned to him, that soft look in your eyes. You saw Bear in a way no one else did, you always acted like you actually wanted him there.
Ian looked proud that someone had stood up for him, yelling out a dramatic "thank you!" in your direction before dragging Bear to sit down on the couch with all of them.
Bear sucked in a breath, mentally cringing at his words before he even said them; "I really don't like these types of games."
The group erupted in groans, as if they were expecting that from him since he always shyed away from anything even slightly outside of his comfort zone. You leaned over, squeezing at Bear's arm gently with a pout on your face.
"Please, Bear. It'll be fun!"
He couldn't really argue with that, not when you were practically begging him to play..he was so weak. Slowly, he just nodded without a word and leaned back against the couch like a dog being told to 'sit'.
The game went on normally, embarrassing stories being shared, Nikki downing a bottle of vodka because she didn't want to do something that Ian had dared her to do as the cards gave prompts to follow. Eventually, it was Bear's turn. He shakily pulled a card and looked down at it, eyes widening at the 'truth' card that he had pulled.
It read: "Share your worst sex story".
Bear practically choked on his breath; he didn't have any. Oh god, Ian would never let him live this down if he told the whole fucking group that he was still a virgin.
He let out a nervous laugh, reaching for his drink as he tried to subtly slip the card back into the deck. Maybe if he drank, he wouldn't have to sit through the embarrassment of admitting the truth out loud. Nikki noticed though, she huffed out a 'dude, you're so boring!' before leaning forward to swipe the card. Nikki analyzed the card for a moment, before laughing softly and turning back to Bear.
"Seriously? No one is going to judge this, Bear." She giggled, flipping the card around for everyone to see.
His stomach dropped as all eyes turned to him, should he just make a story up on the spot? Bear swallowed hard, feeling the heat rush to his cheeks as he looked down at the ground.
"I, uh, don't really have any..." He mumbled against his beer bottle, averting everyone's gaze as he tried to focus on literally anything else. Sarah's eyebrows shot up in realization and Ian barked out a laugh, slapping Bear on the back of his shoulder.
Ian's smirk turned mischievous, he always took everything way too far.
"No way, are you telling us you're a virgin, Bear Bailey?" The mockery in his tone was clear, Nikki suddenly looked really guilty for accidentally subjecting Bear to this clear humiliation. Not that anyone really cared that much, Ian just loved to revel in someone elses misery.
Bear's head tilted up, staring at the group with pure embarrassment--Nikki looking guilty, Sarah giving him a sympathetic smile, and you... oh god, you had heard that..and you looked annoyed at Ian. He suddenly stood up, muttering an excuse about being dehydrated before ducking away from the crowd.
'Stupid, stupid' was all Bear could think of as he walked into a secluded hallway of Ian's house. Why did he freeze up like that? He should have just made up a fake story to throw everyone off his trail.
His self-pity was quickly interrupted when the floorboards creaked and his head snapped up, eyes locking onto you.
You gave him a soft smile, leaning against the wall. It was silent for a few moments, almost uncomfortably so before your voice slowly cut through it.
"Ian's an asshole." You reassured him, trying to meet Bear's gaze but his eyes were glued to the floor.
He let out a soft chuckle under his breath, fiddling with his fingers like an anxious little kid before he looked back at you with flushed cheeks.
"It is really embarrassing that I've never...uh...before." Bear skipped over the word 'sex' because it almost felt too crude to slip out in a casual conversation. Especially with you of all people, the subject of his fantasies ever since he met you months ago.
His gaze landed on your face, your eyebrows were twisted together, and you opened and closed your mouth a few times, as if you were thinking of what to say but hesitating every time it almost slipped past your mouth.
Then, you blurted it out and Bear's heart stopped in his chest.
"I could help you with that."
Holy shit, did he hear you right? His eyes snapped to yours; you were stiff now...almost as if you couldn't even believe you had said it yourself.
Bear laughed nervously, sputtering out a "w-what?"...but he tried to ignore the hope that was blooming in his chest.
Bear had never been religious in his life, but he was starting to believe that there might be something watching over him because this was nothing short of a miracle. He didn't even understand how he got here, but you...dragged him to an empty bedroom in Ian's house.
Bear was so overwhelmed, letting out soft whimpers everytime you dragged your walls up and down his cock. it was unlike anything he had ever felt before, warm heat wrapped around him in a way that made his head spin. His fingers were grasping at your waist, the mattress creaking obscenely as you rode him for the very first time. Nothing compared to this, not even the time he first did molly with the group had made him this dazed and happy.
"A-Ah- Please...!" Bear gasped when you sank down on him with each thrust, his back arching off the bed. There was no way this was real, he had to be fucking dreaming.
He was embarrassed of his noises, he knew they weren't very masculine sounding like most men in bed usually are. Bear was almost afraid you'd mock him for it, but you just stared down at him with a soft smile and kind eyes.
Your hand cupped his cheek gently, guiding his eyes up to meet yours.
"You're so good for me... you like that?" Your voice was soft, hushed into his ear like it was only meant for him.
Bear nodded without hesitation, moaning out a "yeah" as his eyes squeezed shut from pure sensation. His legs were twitching at his side, fighting to ignore the instinct that begged to messily thrust into your pussy. He was close, embarrassingly close, and you had just barely started.
It was hard to focus on the feeling of holding back when your hips were moving back and forth on him, tightening around him so good. Bear’s eyes squeezed shut, he was trying so hard to hold back..to not be embarrassing and finish quickly like a dumb virgin, but it was becoming harder by the minute.
“A-Ah..! S-Slow down..m’gonna cum..” Bear whimpered, grasping at your hips in a desperate attempt to slow down.
You just giggled at him, pushing your hips forward faster and suddenly Bear was spiraling. You wanted him to cum, you didn’t care if it was too early. Bear clawed at your waist, back arching off the bed as he tried so hard not to lose it.
Bear’s head was thrown back against the pillows, his hips twitching as he drove up into you one last time before cumming. He looked like a vision beneath you, gasping out your name as he unloaded into you, cumming harder than he ever had in his life.
It seemed like time had stopped and Bear’s ears were ringing before he collapsed against the mattress, dazed as you finally gave him some mercy to slow down.
You rolled off him, landing beside him..he had a dorky grin on his face, arms wrapping around you.
“T-Thank you..” He shakily mumbled against your shoulder, as if you had just done some sort of favor for him.
