Derek knew it was going to be awkward and insanely uncomfortable.
Stiles and Derek got along fine. They had never gotten in a serious argument and they had always wanted what was best for Talia, Derek's mom, and John, Stiles' dad. So naturally, they were thrilled when the two got married and never had a problem with their marriage.
Unfortunately, John passed away a couple years ago from a heartache, leaving just the three of them.
It got harder after that. Stiles loved Talia, but without John, things sometimes felt impossible. Talia pushed to have Derek be there for Stiles, to help him and be the big brother Stiles always wanted, but it wasn't easy.
Today was one of the days Talia expected Derek to be the good big brother. She'd been gone for a couple days on a business trip and saw that as the perfect opportunity to beg Derek to give Stiles the talk. Yeah, that talk.
Derek begged his mother not to, especially given the fact that Derek was eighteen, and Stiles was thirteen. The age difference was just too weird. Derek tried to assure him her probably knew everything already, but Talia wasn't hearing it. She wanted Derek to give Stiles advice man to man, and Derek loved his mother too much to say no.
Dragging his feet, Derek walked upstairs towards Stiles' room. He took a deep breath, before knocking on Stiles' door.
"Come in." Stiles' voice cracked. Another reminder of how young the kid was.
Derek opened the door and was already feeling embarrassed, even though Stiles had no clue what was about to happen.
"Hey. . ." Derek spoke, walking into the room. Stiles put down the controller to his game.
"So," Derek grabbed the chair to Stiles' desk and took a seat, while Stiles sat up straighter in his bed.
"Here's the thing. . . mom wanted me to talk to you about a couple things."
Stiles sighed. "I told her already I was going to ask Mrs. Ashbry about the math homework."
"Uh. . . no it wasn't about school."
"Oh. Well what's up?"
Derek scratched his stubble, looking away.
"Look kid, this is as awkward for me as it is for you, so let's just get this started. Mom wants me to give you the talk."
"Ah! Gross!" Stiles made a face, sticking his tongue out, and threw in a fake gag for good measure.
Derek rolled his eyes. He expected nothing less from Stiles.
“Dude, don’t even worry about it, dad beat you to it like five years ago.” Stiles made another face.
“Not the sex talk. Well, kinda I guess. I know you know penis plus vagina equals baby, that’s not what I’m talking about.”
“Dude if you start talking about little swimmers and eggs I’m gonna punch you.”
Derek rolled his eyes again. “I’d like to see you try. And no, again. Would you just let me talk?”
Derek waited patiently, surprised when Stiles didn’t talk again.
“This is more of a man to man talk. About. . . changes. Jesus fuck that’s cringey.” Talia has scolded Derek numerous times about using language around Stiles, but what she didn’t know is Stiles had a worse potty mouth than him.
“Dude. I get hairy and shit, I get it.”
“Stiles, just shut the fuck up and listen so I can stop wasting my time.”
“Geez. Fine. Hurry up then.” Stiles threw his hands in the air, waiting with a bored look on his face.
“Okay. You know about boners obviously, considering I’ve caught you sprouting morning wood.”
Stiles’ face and neck turned crimson.
“Wha-wait- wha!” He sputtered.
Derek smirked. “Assuming that you know about wood, you know how to jack off yeah?”
“What?” Derek shrugged, exaggerating the movement. “I’m supposed to tell you this!”
“Ugh! Mom told you to ask if I knew how to jack off? What the fu-“
“No, you little twat. She just told me to cover all the basics of teenage. . . stuff. So just shut up and let’s move on. I already told her you probably knew about all this stuff.”
Stiles turned red again.
“Alright besides your wet dreams and crusty underwear, I’m assuming you’ve watched your fair share of porn?”
Derek waited, but Stiles didn’t respond.
“People don’t actually watch that shit right?” Stiles finally spoke.
“Wait. Are you serious? You haven’t watched porn before? You? Of all people the most curious person ever, the one googled festering wounds because he saw it on TV, haven’t watched porn?”
“Well don’t make it sound like it’s a right of passage! I mean I know what boobs look like!”
“A right of passage? For a teenager with a dick? It is!” Derek said, exasperated.
“I didn’t think people really did that, I don’t know!”
“Well how do you think guys get off?”
Stiles reddened again, looking away and fiddling with his hands.
“Jesus.” Derek ran a hand through his hair. “Okay. Bro on bro here, I cannot let you wack one out again just using your twisted imagination, when it hasn’t even been corrupted.”
Derek wheeled his chair over to Stiles’ laptop and opened it up.
“First mistake, if you’re gonna be a teenage guy, you gotta get a password on all your stuff.” Derek said, opening up a tab.
He turned towards Stiles, who was still sitting on the bed, looking extremely uncomfortable.
“Well get over here!” Stiles scrambled out of bed and walked towards Derek, leaning over his shoulder.
“Alright, soon you’ll discover all kinds of crazy shit, and to each his own, but in just gonna show you the basics for now and you can figure out the rest later.”
Quickly, he typed in PornHub and a flood of images popped up. He could feel Stiles tense behind him. Quickly, Stiles moved and Derek thought he had run off, before he realized he just went and grabbed another chair, pulling it up besides Derek.
“Alright, there are millions of videos on here. They post some everyday, so you can look at the most popular ones or you can search for something it’s up to you. You can also search by category or by people.”
“Category?” Stiles asked, timid.
“Yeah. Like big tits, or gay or cream pie.”
Stiles made a face. “Cream pie?”
Derek shook his head. “I’m going to go ahead and let you figure that one out on your own. Anyways though, you’ll figure out what you like. Everyone likes something different.”
“Well what do you like?” Derek was stunned by the question, and this time he was the one to turn red.
“Uh. . .”
“Oh come on dude. If you get to sit here and embarrass the living shit out of me, I get to ask questions.”
“Well I expected questions about your dick, not my preferences.”
Stiles raised an eyebrow, crossing his arm.
Derek turned back to the computer.
“I don’t know. I like lots of different stuff.”
“Oh come on. You can’t just say that, give me the juicy stuff!”
There was no way in hell Derek was going to share his real kinks. That would be too weird, especially since Stiles seemed to fit a lot of the kinks.
“I don’t know. . . I like guy on guy, I like all natural girls, amateur. The usual I guess.” He shrugged. Stiles and his whole family already knew Derek was bisexual, so he was hoping Stiles wouldn’t ask too much about the guy on guy porn.
“Wait. Guy on guy. . . so. . . I mean how exactly does that work.”
“Jesus, Stiles.” Derek buried his face in his hands.
“Hey! I mean I know they like. . . stick it up the butt-“
“Okay, okay enough. They don’t. . . look there is some other stuff they can do or yeah they can. . . just don’t call it sticking it up the butt, what is wrong with you?”
“Well what do you call it? Taking it up the ass?”
“That’s better than what you said! But no, it’s just anal sex Stiles, Christ.”
Stiles paused. “Do you take it up the butt?”
“Stiles, fuck. Would you just?” Derek didn’t know what he was asking.
“Fine, fine. But what if they don’t like it up the butt? I mean anal sex?” Stiles made a face. “I mean that can’t feel good, just shoving something up there!”
“You don’t just shove it up there Stiles, there is prep.”
“Yeah. You use lube and your fingers to. . . you know what?” Derek turned back to the laptop and searched anal fingering gay porn.
He clicked on the first video, which read fingered and fucked, and sat back.
The video played for a few seconds and Derek was thanking God it didn’t have that cringey music in the background. The video immediately showed two guys naked, and Derek swallowed.
One male was a fit dark haired man, while the other was a smaller, lean twink.
Derek glanced at Stiles out of his peripheral and saw his mouth was agape.
The smaller guy leaned over the bed, while the other began to lean down.
Fuck. Derek didn’t realized the guy was going to rim him first. This would cause a lot of questions.
Derek waited for Stiles to scream or say something vulgar when the guy went in and started rimming the younger guy, making him moan, but Stiles stayed silent.
Derek turned his head to look at Stiles and saw his eyes locked on the screen.
“Woah.” He whispered, barely audible.
Derek cleared his throat. “Uh. . . this is called rimming. It. . . can also kinda help I. . . I guess.” He didn’t really know what to say, but Stiles didn’t ask any questions.
Within a few seconds, the larger man pulled back and poured lube on his fingers, before inserting one. As his finger curled, the bottom moaned in pleasure, sending a wave of heat to Derek’s groin.
“And that. . . feels good?” Stiles asked, timid.
“Yeah. It feels good.” Derek was thankful Stiles didn’t ask if he had been fingered. He wasn’t prepared to tell him of his sexual history.
“There’s a. . . spot in there that makes it feel really good for guys.”
The video played for a few minutes longer, while the man kept adding fingers, before he pulled back and lined himself up.
“Uh.” Derek moved to pause the video, when Stiles grabbed his hand.
“Wait. I wanna see.”
Derek’s face heated up again, but he didn’t pause the video.
They watched for a few moments more, and Derek could hear Stiles’ soft breathing, along with his own heartbeat.
He didn’t know why, but he glanced to his side, and saw Stiles was rock hard. He quickly looked away, back to the video, not wanting to be caught. He didn’t, however, have to look down to see he himself was sporting some significant wood.
A few more minutes went by, before the guy was pulling out and flipping the bottom onto his chest.
He cummed on the guys chest, making Stiles gasp, before he jacked off the other guy until their cum mixed on his chest.
The video went black, but Stiles nor Derek moved.
Derek cleared his throat and shifted in his seat.
“Yeah, so uh. . . that’s that. Um any questions?”
Stiles started to open his mouth, but before he could speak, Derek cut him off.
“Great. Have fun.” With that, he practically ran out of the room into the bathroom. He quickly started the shower. Though Stiles didn’t know much, Derek was sure he knew exactly why he was getting in the shower.
Climbing in, he rested his forehead on the tile and wrapped a hand around his member, tugging until he hit release.
How could a scenario like that go from awkward, to hot, to fucked up? Derek didn’t know. But he wanted it to happen again.