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♡ Let me be your first high ♡

Summary:

Prompt - First Time

Sigma loses his virginity to the most annoying man in the world.

Notes:

(See the end of the work for notes.)

Work Text:

Sigma felt like his head was about to explode.

It had been about 2 weeks since he joined the ADA and moved in with Dazai, and everything had been going smoothly. He was actually a better housemate than Sigma had expected, keeping his space relatively tidy and never making too much noise. Not to mention the warm welcome he had received from the ADA– honestly, Sigma had never felt more happy in his life. The problem with this new living arrangement wasn't Dazai, surprisingly, and definitely not anyone from the ADA...

The problem was that Sigma was needy. He knew that it was normal to have these feelings, especially since Dazai was constantly flirting with him and they had even made out a few times. But this was something entirely new, something more powerful and intimidating than the butterflies he had been slowly getting used to when Dazai was around. No, this was an entire lifetime (so like 4 years for him) of pent up sexual frustration that was now being forced to rise to the surface by his ridiculously attractive roommate. God, Sigma was going to go insane.

It was obvious that Dazai knew what was going on. The way he would teasingly brush a hand against the small of his waist as he walked past, smirking to himself as he went. The way he would bend the most innocent conversations into outright flirting, then act as if he had no idea what had made Sigma so flustered. God, the way he would lounge around shirtless whenever Sigma was home just to see the way his face turned red in response. Yeah, Dazai was a fucking tease.

As expected, when Sigma got home from work that evening, Dazai was laying on the couch without a shirt on. Only this time he had decided to forego pants aswell, leaving him lying around in broad daylight in nothing but his boxers. Sigma felt his heartbeat jump into his throat at the sight– then, when he noticed the half hard bulge in Dazai's boxers, that heartbeat managed to travel down to his dick.

"D-Dazai! God, if you want to be indecent all the time you might as well hang out in a strip club..." Sigma grumbled under his breath, stepping conveniently behind the kitchen counter to hide just how affected he was by Dazai's lack of shame. The bandaged man leaned his head back and laughed, and Sigma's eyes tracked the way his adams apple bobbed with the movement. He swallowed. God he was so fucking hard.

"Aw, don't pout Sigma!" He teased. "Don't you like what you see?" Dazai wiggled his eyebrows suggestively and Sigma choked on the water he had been sipping at the implication.

"I- *cough* Thats-" He spluttered, and Dazai stood up from the sofa and walked over to the kitchen where the other man was standing. Like this he was on full display, and Sigma could see the way his lithe muscles moved beneath his tanned skin. He cleared his throat as Dazai placed his elbows on the kitchen counter and leaned over so that his face was only inches from Sigma's. Sigma was grateful he couldn't properly see the way Dazai's back was arching behind the counter; if he could, it would probably have given him a brain aneurysm.

"You like me." Dazai stated, not even bothering to suppress the smugness in his expression. Sigma kept his face straight and held his gaze, but couldn't stop the way the tips of his ears turned pink. That, and the way his dick twitched behind the counter.

"So?" He challenged. "Why does it matter?"

Dazai laughed, the tips of his white fangs catching Sigma's eyes as he grinned. When he had composed himself, he leaned forward to whisper in Sigma's ear, his cool breath against the sensitive skin making him shudder. "Why, you ask?" His eyes narrowed devilishly. "Because I think you want to have sex with me."

Sigma felt part of his brain short circuit. His mouth fell open dumbly and Dazai laughed again, only this time Sigma wasn't concentrating. Was Dazai disgusted? Surely if he was then he would've kicked him out already right? Oh, but if he isn't disgusted, does that mean...

"Sigma honey, stop overthinking." Dazai snaked his fingers beneath Sigma's jaw and forced him to meet his gaze. "I want you too."

Yeah, Sigma's brain was definitely experiencing some kind of system overload. Regardless, he blinked, registering the deft fingers that were on his chin. Some of them were brushed up against his neck, he realised... Although he wasn't sure why that made his stomach heat up the way it did.

"Sigma." Dazai said, an uncharacteristically serious look on his face. "Do you want me to be your first time?"

Sigma flushed even pinker and stammered "How do you know its my fi-"

"Shh, honey, it's obvious." Dazai smiled. "Now, do you want me or not?"

Sigma's eyes trailed downwards. He took in the sight of Dazai's chest leaning over the counter, his smooth brown nipples that were hard from the cool apartment air, his slim waist and toned abs, his long fingers that were still holding his chin...

"Yes." He murmured.

...

They started off slowly, passionately kissing and grinding against the bed. Sigma was already insanely turned on, his long hair splayed out against the pillows as Dazai held him by the waist and pressed their hips together. This way Sigma could feel Dazai's hardness against him, and felt a wave of nerves overwhelm him. He seemed big, he realised. What if Sigma disappointed him?

"Sigma." Dazai nipped underneath the other man's jaw and he shuddered, his dick leaking in his underwear. "Stop overthinking. If you have concerns, say them out loud."

Sigma swallowed. He certainly wasn't going to admit that he was worried about Dazai's dick being bigger than his, so he voiced another thought. "How are we gonna do this? We have to choose who's on top right?"

Dazai hummed affirmatively against his neck, the slow circular motions of his hips never stopping. "Unless you really want to, I wouldn't recommend bottoming for your first time." He explained. "That's the sort of thing that you have to experiment with a couple times before you go all the way."

Sigma nodded slowly as Dazai's kisses trailed down his chest, his breath hitching as his lips came to wrap around a sensitive nipple. "H-how do I do it?" He stammered. "And what happens if I do something wrong?"

Dazai stopped kissing his chest and instead leaned down on his elbows, his deep brown eyes burning into Sigma's violet ones. He looked so pretty like this, his freckled cheeks dusted pink and his lips slightly kiss swollen. Sigma's heart pounded so hard he was afraid the other man would hear it, and he swallowed nervously.

"Don't worry." Dazai said with a warm smile. "I'll talk you through it. If you do something I don't like, I'll tell you. And if you do something I really like, I'll tell you that too. Sound good?"

Sigma felt as if he was in a bit of a daze, but he nodded nonetheless. He almost couldn't believe it; he was about to have sex with Osamu Dazai, and he was about to spend the night with someone other than his fist. He shuddered as Dazai brushed his lips over his pulse point and up to his earlobe, and nothing could've prepared him for the way he whispered in his ear next.

"Strip" He murmured. Sigma felt his entire body tense from the simple command, and he had to choke back a full on whimper. God, this was going to be more embarrassing than he thought, wasn't it?

Despite his initial shock, it didn't take him long to get rid of most of his clothes other than his boxers– he wasn't mentally ready for that yet. Dazai helped him fold the clothes and place them beside the bed, and when he saw that Sigma hadn't taken off his boxers yet, he decided not to comment. After all, he didn't want to push him too much and scare him off.

"Is it okay if I take these off?" Dazai motioned towards his own boxers, checking that Sigma was still comfortable with them being undressed together. He went pink and mumbled a soft "mhm", his eyes locked onto Dazai as he slowly but surely revealed himself... Sigma swore he forgot how to breathe for a moment. Even though he had never seen another man's erection before, he could tell that Dazai's was gorgeous. He took a moment to stare and take it all in, the way his dick curved beautifully towards his stomach, the way his pink tip was already glistening with precum, the way he could see a vein tracing its way up from the base... Sigma had to actually swallow to stop himself from drooling.

"Like what you see~" Dazai teased, and Sigma internally cursed him for ruining the heavenly experience he was having staring down Dazai's cock like he was studying it. Still, he averted his eyes and steeled his resolve.

"... How do we start?"

God, he hoped that he didn't sound as desperate as he felt.

"Cmere." Dazai said, laying himself down on the bed and motioning for Sigma to lean over him. He obeyed, bracing his arms either side of Dazai's head, letting his long hair cascade down over his shoulders. Dazai thought he looked like an angel, and his stomach swooped in anticipation for what was to come. He didn't want to admit that he was smitten just yet... But damn, did Sigma look good.

"Can you take your boxers off for me baby?" Dazai asked cautiously, testing the waters with a new petname. Sigma didn't reply, but the way his ears burned red as he silently obeyed told Dazai everything he needed to know. Once they were both (finally) fully nude, Dazai hiked his legs up around Sigma's hips and pulled their pelvises together.

"Mmgh!" Sigma stifled a moan as Dazai brought there hips into contact, forcing their dicks to slide against eachother sinfully as Sigma fought to catch his breath. Dazai smirked.

"Come on now, don't tell me you can't handle this much?~" He teased, and Sigma bristled slightly at the insult.

"I-" His voice broke as Dazai thrusted his hips up slightly to increase the pressure. "I can take it."

Half of Dazai felt all warm and fuzzy at the determined expression on Sigma's face... And the other half couldn't wait to make that resolve crack.

"Thats what I like to hear." With one swift movement, Dazai flipped the two of them around so that he was straddling Sigma against the bed. The other man yelped in surprise but quickly regained his composure, his shocked expression turning to a curious one once he realised what Dazai was up to.

"What are you doing?"

"Preparing." The other man replied with a devilish smirk, as he poured a small amount of lube onto his fingers. "This makes the slide easier, so that it isn't painful when I stretch myself out." He reached behind himself and slid one finger smoothly into his hole, his brows furrowing ever so slightly. Sigma's eyes were flitting between his facial expression, his twitching dick and the curve of his wrist right before his hand disappeared from view. He wanted to see, he wanted to know how Dazai was pleasuring himself... He wanted to learn how he could be the one to do it next.

"C-can I?..." The words felt like syrup in his mouth, it felt so wrong to ask yet so impossible to ignore the urge. Dazai, being the genius asshole that he was, seemed to catch on immediately.

"Do you want to try stretching me out?" He asked, his tone taking a flirtatious tone. "You wanna learn how to make me feel good on your fingers?"

Sigma was as red as a tomato. He had no idea how Dazai could say such lewd things with a straight face... But he was right, after all.

"Yes." Sigma said quietly. "I'd like that."

Dazai laid down on his back and pulled his knees up towards his shoulders, presenting his slick, pink hole for Sigma. He marvelled at the way Dazai's thin yet strong body bent into the position, and slowly, tentatively, he pressed his finger inside where Dazai's had been earlier.

Dazai's breath hitched pleasurably. Even though he had been doing this to himself moments prior, Sigma's fingers felt different. They were shorter but thicker, and the angle he was thrusting at made Dazai painfully aware of how close he was to his prostate.

"S-sigma-" He panted, tense with need. "You can add another one. Use your ring finger."

Sigma complied, sliding in his ring finger in beside his middle. Dazai moaned blissfully at the light stretch, the noise hitching up into a whine as the fingers inside him instinctively curled upwards. Just a little bit further, only a little...

"Curl- mmfgh- curl them like that again" He fought the urge to angle his hips against Sigma's fingers, wanting him to find the spot on his own. And sure enough, after a couple curls of his fingers, a shockwave of pleasure was sent shooting up Dazai's spine.

"H-haAh! That's it, that's the spot, keep touching me there... mmfgh..." Dazai tilted his head back into the pillows as Sigma kept on working his fingers over that spot. He noticed that it felt different to the touch, and made sure to keep his attention on that one area. He also noticed that Dazai reacted differently to different tempos; faster would make him breathy and whiny, whilst slower would make him moan and grind his hips down for more. He was enthralled, soaking in every second of the experience as Dazai arched down onto his hand, his fingers buried all the way past the second knuckle.

"F-fuck! Sigma, stop!" Dazai yelped out, and Sigma yanked his fingers (a little too harshly) in a panic. Sweat was beading at Dazai's forehead and chest, and his hair was mussed from where he had been pulling at it whilst Sigma was pleasuring him. He had a slightly glossy look in his eyes, and Sigma's first instinct was to be afraid.

"I'm sorry! Did I do something wrong?!" He said frantically, scanning Dazai's expression for any signs of anger or hurt.

"N-no, of course not, you were doing great, you almost made me cum too fast." Dazai explained with a lazy grin as he caught his breath back. Sigma flushed from the tips of his ears down to his neck. He, almost made Dazai, cum. The knowledge made him throb dangerously against Dazai's thigh, which his hips were still pushed up against. He felt dizzy with arousal, and Dazai could see it in his blissed out expression.

"Sigma." He said, cupping the other man's cheek with his clean hand. "You okay?"

Sigma nodded, almost wanting to cry with how overwhelmed he felt. He hadn't even been touched yet, and he felt as if he could cum from a light gust of wind against his cock. Truly, this was all too good to be true.

"Do you want to stop?" Dazai asked, but Sigma immediately shook his head harshly, not trusting himself to speak. After all, he didn't want to sound too needy...

"Alright. Can you lay down for me?" Dazai asked, helping guide Sigma back onto the bed as he fumbled to comply. When his back was flat against the sheets, Dazai swung a leg over his hips and straddled him. Confusion flashed over Sigma's face; he thought he was supposed to be on top?

"W-what are you-"

"Shh, don't panic, I'm gonna ride you." He explained, and Sigma's expression relaxed a little. However, the tension was quickly back in the form of a clenched jaw as Sigma felt Dazai line himself up with his cock. It took everything in his power not to moan out loud and cum on the spot as Dazai began to lower down, that deliciously tight heat enveloping him in a way he had never even imagined before. He knew sex was meant to be good, but-

"F-FUCK!" His hands flew from his sides to Dazai's hips as he slowly bottomed out, his nails digging into the flesh there as white hot pleasure shot up his spine. Dazai shivered pleasantly as Sigma's tip brushed against his prostate, and ignored the other man's squirming as he began to rock back and forth.

"Hmmfgh..." Sigma moaned unintelligibly with his fist in his mouth, stars dancing infront of his eyes as he watched Dazai rock his hips in small circles againt him. He wasn't even properly moving up and down yet but he was still so close, he could taste that delicious edge creeping up on him, all he needed was for Dazai to go a little bit faster and-

"O-Osamu! Ffuckkk-k-" Sigma choked on his own yelp as Dazai squeezed down hard, hurtling him into the most violent yet thrilling climax he had ever experienced. Dazai's thumbs traces the skin of his shaking thighs and he rode out his orgasm, emptying himself inside Dazai as the other man gently undulated his hips as if he were trying to milk him dry. Sigma slumped back with a shudder, sharp pricks of overstimulation sparking within his senses whenever he felt Dazai move. He was mostly still, barely circling his hips at this point, as he waited for Sigma to recover. Inbetween them, his dick was still hard and dripping with precum.

"You alright honey?" He asked, a teasing edge to his voice. Sigma didn't even have the energy to fight back against the blatant mockery, so he simply whined. This, of course, made Dazai ecstatic.

"Aw, poor baby. Are you already spent?"

Sigma scrunched up his nose in protest and attempted to sit back up, but he found that his core strength had somehow dissipated. Dazai laughed and ground his hips back down, making Sigma twitch.

"It's okay hon, I'll do I'll the work from now on. You just lay there and look pretty while I make you feel good."

Sigma couldn't deny that the condescending tone behind Dazai's words turned him on a little more than he wanted to admit to himself. Still, he gave in easily, falling limp against the sheets before Dazai began to build up a rhythm, making his hips twitch and his back arch off the bed. Dazai was using his thighs to pull himself up and down now, and Sigma, despite doing nothing himself, felt as if he was running a marathon. The pleasure that coursed through him was white hot, overstimulation singeing his nerves in the best way possible, leaving his head empty of everything except the need for "more, more, more-"

"I'll give you more" Dazai panted, planting his hands on Sigma's chest so that he could slam their hips together with more leverage. "I'll give you everything, fuck, you're so pretty, being so good for me-"

"HaAh... 'm gonna cum again, 's-samu!" Sigma whimpered, his hips thrusting haphazardly up into Dazai. The brunette looked heavenly, sweat dripping from his face, skin bare of bandages, white scars for the world to see. Sigma thought that if he wasn't practically the picture of sin incarnate, he would compare him to an angel. Searing pleasure left his limbs useless, and he leaned his head back against the pillows and let one final guttural moan tear itself from his ruined throat before he came, slamming his hips harshly up into Dazai's as the other man convulsed around him, his cock spurting between their chests.

"Shit..." Dazai whined, his thighs trembling ever so slightly where they bracketed Sigma's body. The long haired man felt strangely light, like a weight had been lifted off of his body even though Dazai was currently slumped over him. He shifted uncomfortably, the sensation of cum and sweat cooling on his skin leaving him feeling a little bit gross. He nudged Dazai, who groaned weakly in response like he was about to fall asleep.

"Cmon Osamu, I want to shower." Sigma attempted to wiggle his way out from underneath Dazai, his soft dick accidentally moving against his sensitive insides as he did so, making both of them hiss in painful pleasure. This seemed to wake Dazai up out of his trance, and he sluggishly lifted himself off Sigma's lap, wincing at the feeling of cooling cum dripping between his thighs. With a little bit of effort they managed to get to the bathroom without making any more mess, Dazai waddling awkwardly to keep the cum inside him whilst Sigma laughed at him from the doorway. The pout he got in response made his stomach flip with affection, and he felt a warm flush returning to his cheeks as Dazai giggled back at him.

"We are definitely using a condom next time..." Dazai complained. Sigma was facing the wall at Dazai's request, the hot shower spray tickling him as the other man cleaned himself out. He had refused when Sigma offered to help, a rare flush of embarrassment overwhelming his cocky expression. Sigma thought it was adorable.

"Next time?" He said with a smirk. "How presumptuous. Will you at least take me out to dinner first instead of jumping me the second I get home?"

Instead of laughing, or responding in his usual playful tone, Dazai hummed thoughtfully. "Yeah." He said quietly, and Sigma could hear the shy smile in his voice. "I would like that.".

Notes:

I didn't realise that I forgot to write a condom into this one shot until I was editing it to be posted... It's there in spirit okay be safe guys 😭 Let me know what you think of this oneshot!

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