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Y/n had moved into his college dorm around six months ago, where he met his roommate, Wilbur.
Wilbur was.. odd, to say the least. He was the loner, 'sits at his computer playing Runescape and Minecraft all day' kind of nerd. The only food he knew to make was instant ramen, so Y/n had to cook most of the food they ate. Even as a college student, Y/n was doing fairly well financially through support of his family.
Y/n was also a nerd, but he had his little circle of friends that he loved dearly. He didn't know if Wilbur really had.. anyone, besides his family that he'd left behind to study filmmaking and editing. He spent most of his day at the flat, watching Smosh, playing video games and chatting to strange women on MNS.
But even with their differences, Y/n and Wilbur got along swimmingly, to the point where they had considered each other close friends. Y/n could tell that Wilbur was happy to have a friend, and he was willing to provide.
As guys do, they would sometimes talk about the topic of sex and relationships. Y/n had his fair share of experience with both men and women in his life, but Wilbur seemed to not have tried anything at all.
"Are you not interested in sex? Like, are you an asexual?" Y/n asked his roommate curiously, tilting his head slightly to the side.
"Wh- no, I'm definitely not asexual or anything-" He turned his head away, but the other could still see the bright red blush burning on his face. He could tell that he was trying to find the words to express what he wanted to say, so the h/c boy just stayed silent.
"I.." Wilbur trailed off for a moment, "I just never got close enough, I guess?"
Y/n smiled at the brunette softly before getting up, "You'll find someone to pop ya' cherry soon enough, and when it happens, you'll need to tell me aaaalll about the girl, alright?" He chuckled at he stood in the door frame. Wilbur looked down, not meeting his flatmate's gaze.
"Yeah.. girl." He muttered to himself more than to the man before him. Y/n just smirked.
"Or guy" He said teasingly, "You never know"
Y/n caught a single glimpse of his friend's shocked and red tinted face before he turned back around and walked to his room.
"I'm gonna take a shower, so If you need a piss, go now" He yelled, and only heard Wilbur shuffle behind him, which was answer enough.
Y/n gathered a shirt, hoodie, socks, pants and...
"Where the hell are my Calvin Klein boxers?" He muttered to himself and dug around his underwear drawer for a little longer before he eventually picked a different pair and made his way over to the shower. He set his clothes down along with a towel and hopped in the shower. The hot water loosening knots in his muscles and easing his body felt good, and he let out a little involuntary groan. After around ten minutes, he turned the shower off in a swift motion and grabbed his towel, drying him off tho the best of his abilities before putting his clothes back on and throwing his used towel into the laundry bin.
He walked out of the bathroom, and Wilbur wasn't in the living room anymore. Y/n didn't think much of this, that's what usually happened, but this time he needed to disturb his friend's peace and go to his room to ask what he wanted for dinner.
Y/n walked up and opened his door, only to be met with very interesting sights.
There was a gay porn magazine on the floor by his bed and several others scattered across his room, accompanied by a shoebox of sex toys. Y/n wasn't surprised. What interested him more is several articles of clothing all around the room, all of which he could identify as his missing clothes, mostly underwear. Now he was surprised, but the thing that got him most was the person who inhabited this room.
Wilbur was bright red, hunched over a pillow which had what he could only assume to be some sort of fleshlight taped into it, because one of Will's pant legs was at his knee while the other was still mid-thigh. His casual button up that he always seemed to wear was almost entirely open, only two or three buttons holding the fabric together. Wilbur pushed the pillow onto himself as he tried to hide his red and leaking dick. Y/n noticed he was holding something in his hand, the white and grey fabric he quickly recognised to be his missing Calvin Klein boxers. Will could instantly read the expression on his face.
"I-it's not what it l-looks like-" he tried to explain himself and somehow save himself, but he couldn't find the words. The overwhelming part for Y/n wasn't that Wilbur was obviously getting off to some freak fantasy of him; It's the fact that he liked it.
In fact, he liked it so much that he felt his erection quickly start to grow. Wilbur winced out as his cock jumped and tightly pressed against the inside of the toy. Y/n immediately knew that Wilbur was just as into getting caught as he was into catching him.
"Keep going." Y/n demanded with a stern but lustful voice.
"W-what?" Wilbur tried not to moan out at the sudden change in tension.
"You're into this aren't you?" Y/n took a step closer to the bed, "I mean, who jerks off with their door unlocked?" He chuckled and stared Will down, "You wanted me to catch you, didn't you?"
Will audibly gupled, not speaking or even moving, he just tried his best to hold eye contact before he found the courage to simply nod. Y/n bent down and swiftly swooped up the shoebox that was filled to the brim with different toys- Fleshlights, Dildos, Cockrings, Vibrators, you name it. Y/n looked through the box.
"Well then... how am I going to punish you?" He said seductively, Wilbur wincing yet again as his throbbing cock pressed against the inside of his toy. Y/n saw a remote controlled vibrator in the box and made a mental note of it. Finally, he took a step closer, his knees now almost hitting the edge of the bed where Wilbur was still cowering. Y/n finally pulled out a cockring and a tiny pink remote with it.
"How close are you?" He asked, inspecting the toy and not looking at his roommate.
"V-very." Wilbur admitted.
"Well then you're in for a ride," Y/n put the box down on the nightstand and finally climbed onto the bed, pushing Wilbur down and freeing his deep red cock from the fleshlight. It smacked up on his stomach, making him groan out at the sudden sensation.
"You're gonna enjoy this.." Y/n cooed before finally looking down at Wilbur's impressive size. You know what they say about skinny tall men? They're right.
Y/n gently rolled the cockring onto Will's shaft, making sure not to actually touch his dick just yet. Wilbur let out a long and strained moan as it went all the way down to his balls.
"You like that?" Y/n lowly asked, and Wilbur quickly nodded, almost pleading to be touched.
"Y-yes! G-god fuck yes, I-I need m-m-ore." Wilbur's mind seemed to cloud with the feeling of pleasure. His hands going up to find Y/n's back or shoulders, but the shorter was quicker and pinned both of his wrists together over his head.
"More already?" Y/n smirked, "If I give you more right now," He leaned down and whispered into his ear, "I wont get to do all these fun things with you." Wilbur shuddered at this and bucked his hips up in desperate need of friction. Y/n grabbed the remote with his free hand and pressed the lowest vibration setting, number 1.
"O-Oh!" Wilbur almost yelled as he felt the vibrations go through his most sensitive spots. Loud moans filled the room, and it was like music to Y/n's ears.
"I bet you want me to call you a slut." Y/n's hooded eyes stared at Wilbur, who wasn't able to look back at him. Instead he got another louder moan and a "Y-yes, oh please". Wilbur's whines were the most beautiful thing in the world.
"You fucking slut." Y/n growled, "You went into my room and stole my underwear to jerk off too? That needs punishing."
"P-please," Is all Wilbur managed to muster before I turned the setting to 2/5. He whined out at the rhythmic vibrations, bucking his hips up until Y/n pushed them down onto the mattress.
"Fuck- Y/n- I'm so close-!" Before Wilbur could properly finish his sentence, Y/n turned off the vibrations completely. Wilbur cried out at the loss of pleasure.
"You can cum when I give you permission." His eyes filled with lust and darkness. Wilbur so desperately wanted to finally cum, but he didn't want to disobey Y/n and end this early. "Am I clear?" Wilbur nodded hastily, before he felt the cold sensation of lube on the tip of his sensitive cock. Y/n smeared a little bit of lube onto his right hand, his left still holding Will's hands up. He finally glided his hand down on his flatmate's dick, gaining breathing, strained and lustful moans from him. Wilbur bucked his hips up in an attempt to fuck into Y/n's fist, but the other pulled away.
"I can do two things." He said, "I can give you the longest orgasm you'll ever have, or I can abuse your prostate and punish you if you cum early. It's your pick." While being railed sounded delightful to Will, he wanted to be able to normally sit and walk the next day.
"I-I'll behave." He breathed out.
"Good boy." Y/n praised before he went back to massaging the other's dick, "If you act up again, you'll get punished." he stated. Wilbur only managed to moan out a "mhm!" before the lust and pleasure consumed him. His mind dazed, he moved his hips yet again, and before he knew it, Y/n pulled his hand away. Wilbur only came back to his senses when Y/n grabbed his legs and put one on top of his shoulder, pulling down his own pants and smearing his cock with lube.
He propped himself up at Wilbur's hole and smirked at his thirsting expression. He leaned down to his face and gently bit his neck.
"You're the definition of a whore, aren't you? All spread out for your roommate..." He cooed, "And whores get treated as such." he said as he pushed his member slowly into Wilbur, making sure to not wreck him completely since it was his first.
Nonetheless, Wilbur was screaming by the time Y/n was half way in. He stopped himself to let the bottom adjust.
"F-FUCK." Will yelled, "Is it all the way?" Y/n smiled before mercilessly slamming the rest of his length into the boy and remaining in said position for a few moments. Wilbur screamed out Y/n's name in pleasure. He must've hit his prostate. Wilbur's leg slipped away from Y/n's shoulder, so he leaned down and peppered the bottom's neck in kisses, bites and hickeys.
"Y/n.." he moaned, "Please- please move-" he pleaded.
"Hm? What's that?" Y/n teased.
"Please- f-fuck, please fuck me, use me, abuse me, destroy me, I don't care as long as you fuck me stupid." Wilbur was begging at this point, and Y/n was tired of edging himself, so he slowly pulled out of Will before mercilessly slamming into him again and again and again, hitting his prostate with every push. Y/n groaned at the loudness and the tight feeling of Wilbur's virgin hole around his dick. He knew he was getting close too. With every slam, Y/n neared his high more and more.
"Y/N!" Wilbur suddenly screamed out, "I-I'M SO FUCKING CLOSE, PLEASE MASTER, LET ME CUM, PLEASE- I BEG" He screamed out. Y/n grabbed a fist full of his head as he kept fucking him.
"Go ahead and cum all over yourself, you dirty fucking whore."
Wilbur didn't take another second before his semen shot up against his stomach up to his chin.
"Fuck-" Y/n panted, "Can I cum inside?" He asked with a strained voice, to which Wilbur shouted back a whiney "YES!"
Y/n pushed only a few more times until he came with a loud moan, emptying everything out in Wilbur's not-so-virgin hole.
They took a few minutes of panting to recover. Y/n looked up at Wilbur's tired expression and his overstimulated, still hard cock before pulling out.
"Fuck..." Wilbur muttered before completely collapsing. Y/n grabbed a polaroid camera off of Will's desk and snapped a quick picture of the fucked out boy.
"Did you just take a photo of me?" He asked tiredly.
"Yep, so you can see this tomorrow morning and realise it wasnt just a dream." He winked before putting his underwear back on.
"Stay with me tonight?" Will asked, almost passed out.
"Of course," Y/n replied "but lets get you cleaned up first, wouldnt want your whole bed covered in cum."
"Most of my stuff is covered in cum." He confessed with a light chuckle.
"You do other things than play Runescape and Minecraft?" Y/n asked jokingly.
"Runescape has always been my cover up for porn." They shared a laugh before they cleaned themselves up and layed down in Y/n's room, since it was way cleaner.
"I never took you to be this kinky." Y/n said honestly.
"I never thought you'd go along with it. I thought I'd have to move out and leave your underwear with dried cum here." He chuckled, the other just laughed- They held the conversation a little longer until they eventually dozed off to sleep.