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As a surprise to no one, Shigaraki has never been in an intimate relationship with anyone. His master always said that he should focus on the task at hand, taking down the entirety of hero society starting with All Might. And he had managed to push the craving of intimacy to the side for the longest time. Until he met you. You were a bright light shining in the dim atmosphere surrounding the bar. Like a moth to a flame, Shigaraki found himself drawn to you, praying every second that you'd talk to him.
Shigaraki was awkward around you, of course. He would stutter and could never look you in the eye without trembling, your overwhelming tenderness making his heart race. He almost passed out when you moved a strand of messy hair out of his face while he was concentrating on a video game, his grip on the controller coming dangerously close to disintegrating it entirely. Your casual touches sent all the blood rushing south, leaving him lightheaded whenever your fingers would brush his arm when you gently moved him out the way, bending down to grab a bottle of water out the fridge. Maybe you knew what you were doing, maybe not, but Shigaraki quickly excused himself to his room to deal with the consequences of your actions all the same.
Today, he decided to treat himself nicely, pulling a hoodie you had let him borrow from under his pillow and shoving his face in it. Taking deep breaths of your scent, his cock twitched in his shorts, face reddening as he imagined what it would feel like if you were actually there. Your hands are so soft, they'd feel heavenly running over his body, making him tremble under your touch. Shigaraki let out a quiet whine at the thought of your lips pressed against his, grinding his hips against the mattress.
Your voice would be so sweet in his ear, praising him and reassuring him as your hands explored every inch of him. His hand shot down between his legs and dipped into his shorts, grasping his aching cock and tugging it how he imagined you would. Slowly and gently, you'd be so careful with him, knowing he's a virgin and not wanting to overwhelm him during his first time. Oh. The thought of you taking his first time made his eyes roll back and a raspy whimper escape his drooling lips. Shigaraki's hand wrapped around his cock tighter, imagining how tight you'd feel around him. Letting out a string of moans, he imagined how perfect your voice would sound calling out for him, saying his name over and over as you rode him.
"Shigaraki." He could imagine it so vividly.
"Shigarakiiiii." He whimpered loudly.
"Hey, Shiga-" His door clicked open and his blood ran cold. You were standing in the door way, frozen mid sentence, staring at your leader jerking off with his face buried in your hoodie.
He wanted to cry so badly, but all he could do was stay perfectly still as you stepped closer, closing the door behind you before sitting on his bed. Your hand reached out to cup his chin, bringing his tear-filled eyes to meet your gentle gaze.
"I'm sorry for interrupting," your apology was genuine, no ill intent, no mocking. You were silent for a moment before carefully inching closer to him. "Would you want some help?"
Shigaraki blinked, completely stunned that you were even so much as considering doing anything of the sort with him. He waited for the sadistic laugh, waited for you to call him a loser and leave. He kept waiting. It never came.
He swallowed thickly and nodded, allowing you to move him to sit up beside you before wiping his tears with your sleeve. You cupped his cheek, stroking it gently before leaning closer to him. He could feel your breath on his lips, his heart thumped in his chest.
"Can I kiss you?" Your voice was barely above a whisper, as if any sudden movements or loud noises would scare him off. Shigaraki found himself only able to nod again, rendered completely speechless by you.
Your eyes crinkled with a smile before leaning in to press your lips against his. Soft. You were so gentle with him, light kisses easing him into the feeling before pressing more firmly. Your hand never left his cheek, guiding him in his first kiss. Shigaraki tried his best to match your movements, always just a little too clumsy and a little too slow but you didn't complain. In fact, as soon as he snapped out of the initial haze of the kiss, he noticed you were letting out little hums with each kiss. The blush covering his face reached his ears at your sighs, his cock twitching and leaking with every noise you made.
Your tongue swiped over his bottom lip, drawing a shiver and a low moan from him before parting his lips to give you access. The feeling of your tongue lapping over his made his head spin, the tension in his stomach becoming too tight for him to handle. All it took was one little moan from you and his cock was twitching, shooting out rope after rope of cum, stars popping behind his closed eyes as you kissed him. Shigaraki felt dizzy, the embarrassment of cumming in his shorts just from a kiss settling in as you pulled away to let him catch his breath.
"I-I'm sorry," he hiccuped, tears welling in his eyes. He had everything he wanted and his stupid body ruined it. Your hands were cupping his cheeks again, squishing his face as he sniveled.
"Did it feel good?"
"...Huh?" Shigaraki blinked, "Y-yeah..." You smiled tenderly at him, carefully pushing him onto his back before crawling on top of him.
"Do you want to do more?" You straddled his hips, his cock twitching back to life. Shigaraki shivered at the feeling of your sex pressed against his, he could feel your arousal.
"Yeah, I've just..." Never done this before. Never had anyone touch me. You hummed knowingly, gently rocking your hips against his, drawing a strangled moan from Shigaraki, his sensitivity shooting through the roof with each movement of your hips.
"I'll be your first then, if you'll let me." Shigaraki nodded fervently, hands splayed awkwardly by his sides as you leaned down to catch his lips in a kiss again, drinking up every sigh and moan from you. You pulled away, kissing the tip of his nose before sitting up, your hand running down his chest, over his stomach, down to the waistband of his stained shorts.
Your eyes flicked up to his, gauging his expression as your fingers hooked under his shorts, slowly tugging down. Shigaraki lifted his hips, silently giving you permission to strip him. His cock rested heavy against his stomach, covered in cum and already leaking more precum. His eyes were glued to you as you stood to match his state of undress, his mouth going dry as you situated yourself on his hips. He could feel just how turned on you were, your slick mixing with his as you ground down against him.
"Wait- I'm close-" Shigaraki croaked out, relieved as your hips slowed, only to be taken aback by his cock pushing into your hole. As soon as the tip sank in, he felt himself cumming again. He flung an arm over his face, closing his eyes and panting as he filled you with his cum. But your hips didn't stop until he was fully inside you, buried deep in your hole.
He could feel your walls fluttering around his aching cock, gentle hands pulling the arm covering his face to the side before pressing kisses all over his flushed cheeks. You were so hot and tight around his sensitive cock, each twitch of your hole made his back arch. Shigaraki felt as though he'd melt right into the bed once you began rocking your hips, fucking yourself onto his cock.
You leaned on your forearms, dipping your head down to his ear, every moan and gasp from you sending shocks of pleasure straight to Shigaraki's cock. Drool spilling from his mouth, his eyes rolled back as you bounced on his cock, shoving it deeper and deeper. The room was filled with slick noises of his cock sliding in and out of your cum-filled hole, mixed with both of your moans and Shigaraki's stuttering breath.
"You're doing so well, Tomu. So good for me." Something inside Shigaraki snapped, letting out strings of incoherent whimpers, begging for more. His arms flew around you, hugging you tight to his chest as you fucked yourself on him.
"Please- more- Praise me more." Too far gone to form full sentences, Shigaraki dug his blunt nails into your back carefully. Your voice was an aphrodisiac to him, every word and every moan making the haze filling his head more and more heavy.
"You feel so good inside me. God, I've wanted this for so long," your confession made his vision blurry with tears of joy and overstimulation. "You're so precious- Tomu-" Shigaraki felt your hole clamp down on him as you came around his cock, his voice escaping him in broken whimpers as he reached his limit again.
"C-cumming...!" Letting out a loud sob, his cock throbbed inside you, shooting his cum deep into your hole. He buried his face into your neck, hot tears and drool staining his cheeks as you peppered his face with kisses, letting him catch his breath underneath you.
His grip on you weakened, whining sharply as you slipped off of his sensitive cock, laying next to him and pulling him into your chest. Shigaraki lay there, panting and pressing open mouthed kisses to your chest as you rubbed his back soothingly.
"That's it, baby boy. You did so well for me," your voice rumbled through your chest, causing him to nuzzle closer to you. You pulled back enough to wipe the tears and drool from his face before pressing a kiss to the top of his head, his hair damp with sweat. "We can clean up in a bit, just lay here with me, okay? I'm not going anywhere."
Shigaraki let out a content noise and cuddled into you, wrapping an arm around your waist, a dazed smile on his face.