First time with Dazai
Dazai Osamu x Male Reader
CW: Day of Oda’s death, day of Dazai defecting from Mafia, both Dazai and reader are 18, might be ooc, mentions of Dazai’s usual antics, scars mentioned, extreme thinness mentioned, angst to fluffy smut, virginity loss
This night had been the worst of Dazai’s life.
He’d been shot before, beaten, went to sleep hungry and cold in a shipping container every night, and this was the worst of them all.
His best friend had died in his arms and now he needed to leave behind all he’d known for 6 years.
He was ready to do it at Oda’s request though. Just, not without one last thing.
You and Dazai had been dating for about 3 years. You hadn’t seen him today but it was common for him to disappear sometimes. You just hoped it wasn’t because he was doing some dangerous shit again.
It was when you got home to your quiet apartment that you almost whipped your gun out at the feeling of being hugged behind. Until you heard Dazai’s familiar “Hey..”
Your shoulders relaxed and your hand retracted from your gun holster. You turned to face him but he kept burying his face in your chest, refusing to look up at you.
“Hey.. what’s going on? What’re you doing here?” You tried to coax him out of his little hiding space like a stray cat, speaking softly as you tried to lift his face into your hands.
The second you lifted his face, though, he immediately pushed his lips onto yours. You were more focused on the fact that he no longer had his usual bandage wrappings around his right eye.
“Dazai-“ You kept trying to intercept, fighting to get a word out, but he won’t allow it. By now, you knew Dazai long enough to know he was avoiding something.
He pulled you along all the way to your bedroom, tossing himself back onto the mattress and dragging you over him. You caught yourself just over him, hands resting beside his head. “Dazai- wait-“ You had to hold him down by his shoulders to get him to stop. “What’s going on?”
Dazai pouted but not the usual playful way. It was more solemn, genuine disappointment at being pulled away. He sighed, looking away before speaking up again. “If I asked you to run away with me, would you? No matter how risky?”
Your face shifted in confusion. What the hell was he talking about? “Run away? From what, the mafia?” You almost laughed at the absurdity until registering just how serious he was about this. That’s when things went quiet.
“It’ll just be you and me. Sure, we’ll have to lay low but Ango has a plan-“ Dazai rambled “Wait- Ango? What does he have to do with all this? Are you serious?” You interrupted, moving off of Dazai to sit beside him.
“He’s gonna help me lay low after I leave-“ “After you leave? So this isn’t even a hypothetical? You’re leaving?” Now you were racing, confusion muddying your thoughts.
He grabbed your hands “Not without you. I don’t want to. So please? Say you’ll leave with me?” He pleaded, dark brown doe eyes tugging at your heartstrings.
“Why are you leaving? I don’t understand what’s going on with you. First, you were gone all day, now you’re skipping town?” “We’re skipping town! I just need you to say yes.” He cupped your cheeks, trying to smile at you in hopes it would convince you.
“I don’t even know what going on with you! How can I say yes when I’m left in the dark?” You argued a little harsher than you meant to but you were getting scared. You were standing over him now.
“Why can’t you just say yes? For me?” He pleaded, more than you’d ever seen in years of knowing one another. He clung onto your sides. Tugging you toward him by the jumbled fabric of your shirt.
“Dazai, this isn’t a game.”
“I don’t think it’s-“
“If you really mean this then be honest. What the hell is going on?”
“I-“
“And don’t avoid it anymore! I’m not letting this go-“
“Odasaku’s gone!” He called out loud enough to get your attention.
You froze in shock, confused but also perfectly aware of what that meant.
“He’s dead.. shot. I watched the life leave his eyes, his limbs so limp in my arms..” His voice broke near the end, head dropping as he pulled you closer again.
“Please.. don’t let me go alone. I can’t do this without you..” For the first time, you heard Dazai cry. The sound was outright heartbreaking. This was the worst night of your life.
With a deep breath you rested a hand on Dazai’s head “Ok.. ok, let’s do it.” He gasped, head lifting to look at you hopefully.
“Let’s run away together.” You finally agreed, causing Dazai to sigh in relief and rise from the bed to hug you. “Thank you- thank you-“ He rambled against your shoulder.
You stood there in each other’s arms for a while until he composed himself and spoke “Leave your phone and everything. Keep whatever packing you do down to what you can’t live without.. I’ll call Ango.” He kissed you before leaving the room to make the call. This was really happening.
In less than an hour Ango was at your place. He got both of you into a car, sent off with coordinates to a safe house outside the city. The drive was long and quiet but you made it by morning.
You let the car drive off into a nearby lake before settling in.
It was when the doors were all locked and you were finally safe that Dazai kissed you again, arms wrapped around your shoulders as he pulled you toward the only mattress in the safe house.
You both landed with a groan at the firmness, now knowing the mattress was more like a military cot, but beggars can’t be choosers.
Dazai chuckled before locking your lips once again, not wasting a second before climbing on top of you, sat on your abdomen.
“It’s.. something at least. We’re more alive than any other mafia defectors.” He shrugged, pecking your lips again.
“Life won’t be easy from here on. We’ll be in danger for years, maybe even forever.. so, I want to experience the best of our lives together for however long we can.” He whispered against your lips.
“We can’t get married, but I don’t see the harm in pretending this place is ours. Pretending it’s our wedding night..” He began undoing your tie from the work attire you still hadn’t gotten to change out of. You got the hint.
You moved your hands from his hips to his belt buckle, undoing it gently before slipping his belt out from its loops. He was already working on your vest, your tie discarded in a similar direction to his belt.
You used a free hand to pull him in for a kiss again. Your lips rarely separated as you both spent the next few minutes undressing one another. You didn’t fully pull away until you were both just in your boxers, Dazai’s skin covered by nothing but his bandages.
You held his waist as you looked him over, admiring him even with the bandages on. You were ok with Dazai keeping them on, they were part of him. At least a part that kept him comfortable.
You were shocked when he sat up and began loosening the bandages at his neck, tugging and unwrapping until his skin was bare. It had faded scars, likely friction from things you’d rather not think on.
It was when he removed the ones on his forearms that you realized you were holding your breath, and staring from the way Dazai began shyly closing in on himself.
You gently grabbed his wrists before he could shy away, sitting up a bit.
“You’re so beautiful..” Was all you muttered before kissing the scars at his wrists. You could’ve sworn you saw Dazai tearing up before he blinked it away, taking his wrists out from your hold before grabbing your face and kissing you again.
The kiss heated up quickly, both of you clearly a little impatient to get your hands on each other for real. Tongues danced eagerly, accompanied by the equally as eager grinding of Dazai’s hips down onto your own.
You moaned into each other’s mouths before hands began shifting toward both your boxers. You both stripped your final layers before Dazai pulled away, your lips chasing his own as he pulled you to sit higher up on the bed.
Getting right back onto your lap, he prodded his fingers at your lips, pushing past them to soak his ring and middle. It was your best bet with no.. intimate tools in the room. You couldn’t blame Ango for not thinking about that, though.
Once soaked, Dazai pulled his fingers from your mouth, lifting himself up a bit before moving his hand down between his thighs, fingers disappearing out of your view but his soft whimpers told you surely enough where they went.
While he prepped himself you pulled him back in for another kiss, distracting him from the stretch.
After a few more minutes he let out a sharper moan, having found a spot that made him see stars. He was wiggling his hips cutely by now, almost trying to get his fingers deeper. Whining when he couldn’t.
“C’mon.. I’m ready.” He pulled his fingers out, spitting in his hand a little before taking your length into his fist, coating it along with a few generous strokes.
He lifted his thighs, placing a hand behind himself to align your member to his entrance before finally, slowly sinking down onto it with a shuddering moan.
Your hands gripped onto his hips as he settled, helping him ease down at his own pace. By the time he fully sat you were both left breathing heavily.
He let himself lay on your chest for a moment, adjusting to the physical intrusion as well as the emotional weight of what was happening. You and him were finally having your first time together.
Numerous times, Dazai thought he’d have ended his own life or just died during a mission before he would ever get to have this level of intimacy with you. Despite what he says about wanting to die or asking you to join, he’s never been so thankful for life as he is in this moment. He found love.
You held him there, not in any hurry to begin. This was enough. Having him there, having this moment together. It was good enough for you.
You’d both gotten relatively close a few times but none of those times were anything like this. This was beyond lust or a fit of passion. This was love. You became the only person in the world the Dazai Osamu trusted his body with.
Soon enough he got his heart to slow down a bit, not getting over the emotional weight but able to handle it now. So, he readjusted your hands at his hips as a sign to get things going. He knew he’d need your help.
He began by rolling his hips experimentally, groaning softly to himself as he felt something other than fingers inside for once. He sped up the pace after a bit, groans turning into moans after a while.
Dazai had touched himself before (and occasionally got your help as well) but he’d never felt anything this good. Dazai always told himself he would be composed and sexy if he’d ever lived to do it with you, but right now, he couldn’t care less as his lips fell open unconsciously.
His moans weren’t loud, not yet, but they were pretty. So so pretty.
They were set lower, like his real voice when nobody was around to perform for. They were primal in the way they almost sounded forced from his chest.
When he realized how vulnerable he was being he did reel back a bit, falling into his habit of self preservation as he brought a hand over his mouth, muffling his moans into his palm.
You didn’t force him to share them, instead just using his shyness as motivation to make him forget all his fears.
You eventually helped him move on from grinding to actually bouncing. It wasn’t a lot, just cute bunny hops at most, but it took a lot out of Dazai who was now wrapping his free arm around your shoulder and hiding in your neck. You somehow got harder due to the sound of Dazai’s whimpers and muffled moans so close to your ear, allowing yourself to buck up into him now that he could take it.
That pushed a louder moan right through his fingers. You could feel him bury himself further out of embarrassment. So cute.
You could tell his legs were already growing weak, shaking with approaching fatigue. You kept helping him ride you for a while longer, but soon enough you eased him onto his back. You couldn’t possibly make him do all the work.
He was surprised at the sudden change, immediately flustered by the sight of you on top of him and bringing his hands over his face. He was so painfully cute. You were so blessed to see this side of the “demon prodigy” everyone was so afraid of.
You gently wrapped his legs around your hips before sliding your hands up onto his, slowly peeling them away from his face as you leaned in.
“Don’t hide from me, love. Ok? There’s no need. I’m not gonna judge you.” You whispered against his lips before softly kissing him to ease his pounding heart.
You then gradually got back to moving inside of him, taking the reins now so he could just relax and be pampered. He seemed to like it, moaning against your lips despite himself.
After a bit you felt his legs tighten and tremble around your waist, his voice pitching higher. “I-I… ah… Y/N… I think ‘m close…” he murmured against your lips, needing to warn you. You soon noticed you weren’t much better off, an apparent heat pooling in your abdomen.
“Me too… I’ll pull out soon, ok?” You kissed at his sweaty temple, hand gently pushing back his thick bangs so he wouldn’t overheat.
He whined a little at the idea of you pulling out but it was your first time, he wasn’t expecting you to cum in him when neither of you had protection on you. Even if you both were knowingly clean.
You knew he’d be spilling any second now when his back arched, making him break your kiss. He was so pretty with his head tilted back and his brows furrowed. You couldn’t help but look over his body one more time, admiring how beads of sweat rolled down his scarred skin, how the ends of his ribs pushed out from under his skin due to his slimness. He was so beautiful to you, even if he felt so flawed.
With just a few more thrusts, he cried out in a way you’d never heard before, thighs squeezing you as he came onto his own stomach.
His entrance was also squeezing you so deliciously, fluttering with stimulation. You couldn’t hold back much longer, only lasting a handful more thrusts before hurriedly pulling out, cumming onto his inner thighs last second. What a beautiful sight.
You both sat in silence for a good minute, panting from the physical exertion as well as emotional. You let yourself lay on his chest for a bit as you recovered, almost giving in to the comfort when you felt Dazai’s hands in your hair.
You looked over to him and smiled so affectionately. He was so beautiful with his face flushed like that. Even more beautiful when he smiled back.
He pulled you up by your face, bringing you into a kiss all over again.
This had been the worst day of his life, but you made it livable. Even for him of all people.
He would live on. He would stay by you as he became good. Good for Oda, and good for you.













