Stiles’ whole life is an example of being contradictory. Major events in his life are marked by one particular sentence:
So in a way it was only natural that it was a similar exchange to that which made him start thinking about the possibility of boys as attractive to him.
“You’re not gay.” “I could be .”
He didn’t tell his Dad for months, years even, that it was that particular exchange that made him first consider it as an option. That made him think that boys were just as attractive to him as girls were. It was kind of fortuitous -- okay, his Dad would call it a misfortune probably -- that the conversation and subsequent self-exploration happened at a time when Derek Hale was around. Derek “I work out at all hours of the day” “my abs have abs” “tall, dark, broody, and inexplicably fascinating” Hale, who had no idea at the time how much he contributed to Stiles’ discoveries about his sexuality. It was all theoretical at first, nothing but Stiles looking and thinking about whether men had the same effect on him as Lydia.
It didn’t take long to realize that he got just as hard at the image of his long-term red-haired crush as he did at the glimpse of Derek’s shirtless torso. With his sexuality confirmed as bi the moment he first took his dick in hand with the thoughts of Derek’s body against his -- the memory firmly cemented in his brain after the hours in the pool -- Stiles began wondering about his romantic orientation too. Because it was one thing to find the male form interesting and arousing, and a whole other to have feelings for someone.
By the time he turned eighteen, Stiles had woken up from a dream about a stubbled jaw and rough fingers enough times to know that men turned him on as much as women did. He’d grown closer to Derek as time went on -- he’d even consider them friends now -- and he dated here and there. He even had hookups now that he was legal and wasn’t afraid of his father’s threats to arrest his potential partners for statutory rape. There was no one that he fell for, not the way he used to be obsessed with Lydia for sure, nor any other way since he realized that that hadn’t been love at all. So he still wasn’t sure if he could find a guy romantically attractive.
The ongoing exploration of his feelings didn’t stop him from figuring out what did and didn’t turn him on, though, and Stiles -- being as thorough with it as with any other research -- dove into porn, online articles, and whatever other sources of information on bisexuality he could think of. At the end, though, what proved most illuminating and confirming of his preferences was his own imagination.
It became habit for him to think of being pressed into his pillows by a warm and muscled body, of stubble scraping against his skin, of a hand slightly bigger than his own wrapping around his cock and stroking it with firm and practiced moves. Not that Stiles admitted it even to himself, but the man he was imagining had a striking resemblance to a certain grouchy werewolf. He tried to keep quiet -- something he had practice with since he discovered the art of jerking off -- and it allowed him to ignore the voice in his head speaking the name of his imagined companion.
Once he started dating, after the pack became more solid and the town was no longer monster central, Stiles added some of those experiences to the little folder in his brain labeled “turn-ons” and some to the “nope” one. None of them were all that different from what he did alone, not yet. They only happened to involve another person’s presence, and another pair of hands on body parts he already knew were sensitive to touch.
He liked the obvious: kissing, having his nipples touched, hands on his skin, and thanks to one particular trip to Jungle, he knew that someone else’s hand on his dick felt a lot different -- a lot better -- than his own. Sure, he was still not quite done with third base, but the first two so far proved that he was indeed bisexual.
There were things he didn’t want to jump into with a complete stranger, though, and despite his success at attracting attention in Jungle there weren’t any guys -- or girls -- whom he’d trust enough. The ones he’d pick weren’t, as far as Stiles was aware, options for his experimentation. So after he’d binged on porn and researched everything in theory, he figured that he’d just need to do it alone.
He was still living at home, which restricted his self-love sessions to times when his Dad was at work. The downside to Stiles’ insistence that John start taking it easy was that those times became fewer, at least the ones not coinciding with school hours. He couldn’t really be blamed for checking his Dad’s schedule so that he’d know when the house would be empty,
“Is Scott coming over?”
John was pulling on his jacket as he asked, barely glancing at Stiles, who was stretched out on the couch.
“No, he’s out with Kira tonight,” Stiles replied, trying to sound casual.
“You heading out then? Should I have someone swing by Jungle through the night in case you need a save?”
“ Dad! ” Stiles squeaked.
It happened before, when Stiles’ back-up -- he was still on friendly terms with the regulars in there -- didn’t manage to swoop him into safety from unwanted attention. He still seemed to be appealing to guys that reminded him all too much of Peter Hale’s creepy ways. More than once, Parrish’s presence kept Stiles from trouble of the non-supernatural and entirely “humans suck in ways that aren’t even a little good” kind. Nevertheless, Stiles cringed every time John brought it up, because no matter how open-minded his Dad was, he was still Stiles’ Dad and therefore any and all conversations related to sex were bound to be awkward.
“Okay, okay,” John said and raised his hands in surrender. “I’m just making sure.”
Stiles threw a small cushion in John’s direction to show his displeasure with the teasing. It ended up hitting the wall next to the hallway door, and Stiles grumbled as he got up to retrieve it, since John escaped the hit by rushing out to work. It took another few minutes after the sound of the cruiser’s engine disappeared for Stiles to feel like he finally had the privacy that he was looking forward to. He was in his bedroom not ten minutes later, T-shirt and shorts scattered in the space between his room’s door and his bed.
He wondered at first if he should play some of the porn he knew that he’d found appealing, but then he decided against it -- his imagination and memory supplied the necessary images, and he didn’t want to be too distracted. He’d already almost gotten derailed earlier during his shower by just thinking of what he had planned for the evening. There were things to try out and preferences to confirm.
“No new worlds to discover,” he mumbled to himself as he stretched out on the bed and tugged the drawer of his nightstand open.
He covered his fingers in lube and pushed his boxers down to his knees with his clean hand, then he kicked them off the rest of the way. Meanwhile, the lube -- the special occasion kind -- warmed up as he spread it over his cock, already hard in anticipation. When the last piece of clothing fell off the bed, Stiles took a deep breath before he spread his legs and lifted his knees. He’d read several things about the most comfortable position for anal sex, whether with or without a partner, but he didn’t find a definitive answer, so he figured being on his back was as good an option as any.
At the first touch of his lubed -- and warmer than usual thanks to that lube -- finger slipping past his balls and over his hole, Stiles tensed. It was a combination of anticipation and worry that made him pause, but then he moved his hand again, determined to continue with his “research.” As his finger slowly circled his hole and he tried to press past the muscle, it became clear that his hand wouldn’t help much with that exploration, because it was awkward and the angle was all wrong.
Instead of twisting his wrist in increasingly aching ways, he turned a little and ended up on his side. One hand back to stroking his cock firmly, the other reaching behind and spreading the lube over his asshole -- not breaching inside though -- he jerked off with the knowledge that it was a very good possibility that he was into being fucked. When he came, his finger slipped past the muscles as they spasmed along with the rest of his body, and it added a new layer to the strength of his orgasm.
“Definitely my thing,” he whispered to himself as he tried to catch his breath.
Since he knew that he wasn’t going to be able to fix the issue of his arms’ length and the awkward angles, Stiles came to the conclusion that any further progress would require help. Because there was no one to ask, Stiles bit the bullet and found a time the next day to head just outside the town boundaries, to a sex shop that he had been aware of for years.
It was a small, inconspicuous house. Stiles knew it was for the customers’ privacy as much as it was to avoid trouble. There was no sign, nothing on the outside to give away what lay inside the walls, and Stiles only knew he was in the right place because he didn’t miss the tasteful -- but at closer look quite explicit -- nude statues in the front yard. He walked in without hesitation, partly also because being seen had the potential to invite questions he wasn’t prepared to face.
Inside were a few rooms converted into what looked less like a seedy and questionable shop and more like a presentation of more choices that Stiles knew what to do with. He’d had a plan when he decided to come in: find something for people new to anal sex, maybe ask about the best ways to prep himself beyond the cleaning and his own fingers that he already knew about. The shelves in the shop made him stop and think about what else was there that he could experiment with.
At first, he cautiously eyed and picked up plugs and small vibrators, putting aside a few that he thought would be good for the start. Then he got lost in the selection of lubes -- some familiar, some new to him -- and when he left those, he wandered into the section with DVDs.
But then a display caught his eye. It was in the corner of one of the rooms, not hidden but also not something that the owners considered to be good sellers. When Stiles walked closer, it became very clear why. The shelves held dildos that made Stiles cringe a little because of the size, especially since they beat even the most adventurous porn that he managed to find during his research. Then, just as he was about to walk back to the plug set and lube he’d set aside near the counter, he spotted the one box with a drawing resembling a wolf a little too closely.
He picked it up and chuckled quietly when he realized that the dildo inside not only flared out at the very bottom the way the regular ones did but also had a part just above the base that was a lot thicker than any others.
When he glanced towards the counter and spotted Danny, Stiles didn’t hesitate, and he started walking over, the box with the dildo still in his hand. He’d known that Danny sometimes worked in the shop -- it was how Stiles found out about it in the first place -- and there was no better person to ask the questions that inevitably started nagging at Stiles’ brain.
But before he reached the counter, someone ran into him -- literally -- from behind a row of shelves that Stiles was walking past.
Stiles looked up sharply when he recognized the voice. His eyes slid over the henley he knew all too well and up to the face that was quickly switching between expressions of surprise, being apologetic for the run-in, confusion, and a hint of amusement. The last one was strengthened by the way the corner of Derek’s lips pulled up into a smirk when he noticed what Stiles was holding.
“What?” Stiles said, mild panic rushing through his body. “That’s absolutely not what you think it is. Unless…,” he paused and narrowed his eyes at Derek, whose ears were turning suspiciously dark. “Unless it is a thing? I mean, I was going to ask Danny, because I figured he’d know after his relationship with Ethan. Not that I have exhausted all other such activities that I’d need to go to extremes. I mean, I’m not even sure if I like getting fucked, though I’m pretty sure I will.”
As Stiles talked -- more to avoid the awkwardness that silence would bring -- Derek’s eyes widened, and he seemed to be processing all the information. Including when Stiles mentioned how far he got with his exploration and why he was in the shop.
“I don’t know if it’s a thing,” Derek finally said when Stiles took a breath and was about to drop everything to make his escape.
“Knotting. I don’t know if it’s a ‘thing’. Never happened to me, at least,” Derek explained.
They were both startled when Danny walked up and cleared his throat to get their attention.
“It can happen, it just depends on the relationship,” Danny said when he spotted the dildo in Stiles’ hands. “It can be pretty amazing too, in case you wanted to know.”
“Not particularly,” Derek said just as Stiles blurted: “Wow, nice.”
Derek’s eyes flashed a little in a way that would have been dangerous had Stiles still been afraid of him. And awkward if they were anywhere but in the presence of Danny, who was maybe not really pack but was still in the know about the supernatural.
“It’s not just Alphas either,” Danny said with a smirk, and he walked back to the front counter, leaving Derek growling in irritation and Stiles staring at Derek in a way that was only partly surprise.
The other part was one that he wasn’t going to be able to deny this time. He was curious, now more so than ever before, about everything from the fact that knotting apparently was real all the way to whether Derek would…
“No,” Derek spat out, a low growl accompanying the unprompted word.
“I didn’t even say anything,” Stiles immediately protested, because, well, he didn’t, for a change, voice his thoughts. At least he didn’t think he did.
“I can smell you ,” Derek said more quietly, and from a lot closer to Stiles’ ear than he was before. “I can imagine what you’re thinking without you saying the words.”
“Maybe I was thinking about Danny,” Stiles attempted to defend himself, but even he knew that it wasn’t going to work.
“You weren’t,” Derek told him, and when Stiles turned to get a better look at Derek’s face, he didn’t miss that it was different than usual.
It wasn’t closed off, or angry, or distant as Derek still had a habit of being when something that was happening wasn’t to his liking.
“Okay,” Stiles nodded. “Is that a general, all-encompassing no? Or like ‘not in front of Danny’ kind of a no, or ‘not you ’ kind of a no?”
“Maybe,” Derek said, leaning closer for a second, just enough that Stiles’ response ended up being just a ramble of sounds.
Derek only replied with a smirk, and he threw Stiles off completely when he reached for the box and marched to Danny. Stiles was still frozen in his spot after Derek made his purchase and walked out of the shop with a quick glance at Stiles, the smirk still on his lips.
“What the fuck just happened?” Stiles asked in the sudden silence, and then frowned when he heard Danny chuckle.
“That was as close to an engraved invitation as you’re ever going to get,” Danny told him a moment later, when Stiles managed to get through the shop again and then to the front with a few of his earlier discoveries.
“He didn’t buy that for himself,” Danny told Stiles, and both of them paused for a moment to consider that thought.
There was a definite twinkle in Danny’s eye when they both went back to normal thoughts. Stiles couldn’t say that it wasn’t an intriguing possibility, but it wasn’t what his mind was occupied with. He grabbed his purchases once he paid for them, and his drive home was spent mulling over his new toys and what Derek intended by buying the dildo. Stiles most definitely knew what he wanted the intention to be, he just didn’t dare let himself hope.
He didn’t get the answer to his musings immediately. The night that he got home with his purchases, his Dad was already there, so Stiles just shoved the bag into the back of his sock drawer. By the time John left the house again it was the next morning, and Stiles also had to go out, and he was glad of the distraction from those thoughts because Scott never failed to comment on Stiles’ scent.
Stiles stumbled back into his room later that day, not drunk but exhausted from a run that Scott and Isaac talked him into after breakfast. He knew he’d need a shower immediately, but as he dug into his drawers for clean clothes, his fingers bumped into the paper bag containing the plugs and the one small vibe he had ended up buying. Despite his tiredness, he -- and his dick -- perked up at the thought, his brain reminding him that his Dad was out and the house was empty.
In the shower, Stiles recalled all the details that his research mentioned about cleaning and prep for any sort of play that he was looking forward to. His shower took a little longer than necessary, and he was rock hard by the time he was done, even though the angle at which he had to twist made his arms a little achy. Once he was in his bed, all that was forgotten when he put his purchases on the nightstand, along with the new bottle of lube he got since his visit to the sex shop.
“Okay, Stiles, let’s do this,” he mumbled to himself.
It took a little shuffling and figuring out the best position, then jumping out of bed to check that he locked the door and that his window was closed. Not that he’d expected anyone to barge in, but even though he was eager to try out at the very least the smallest of the plugs, he was still cautious.
The lube was cold against the ring of his ass when he finally settled on being on his knees, ass up, his cheek pressed into the pillow. The angle was still not that comfortable, but his fingers breached the muscle ring like they did earlier in the shower, and once the lube warmed up at the contact to his body, Stiles was sure that he was most definitely enjoying the sensation of something inside him. He reached for the smallest plug, the tip of it barely thicker than his finger, and he coated it with some more lube, remembering the “never enough lubrication” suggestions he found online.
He gasped in surprise when the plug slid past the rim, easier than he expected it to go. Sure, he knew he got the tips of two of his fingers in earlier in the shower, but even with the extra lube he expected resistance of the muscle. With the ease that the penetration took, Stiles relaxed a little, and the plug slipped in a little further, making him let out another quick gasp. It wasn’t long, so another press further made it slide in completely, all the way to the grip at the end. Sure that it would be okay to let go, he brought his hand back to his front and his fingers came in contact with his dick, which was softening a little. He was still turned on, though, and it only took a few strokes for him to get fully hard again, which in turn made his ass contract around the plug.
With the new sensation of the plug along with the familiar sensation of jerking off like he used to, he came only a few minutes later. The aftershocks took longer than they would’ve been usually, though, thanks to the plug still inside him. When he finally came down again enough to pull it out, he whimpered at the sensation of the plastic rubbing against his rim and then the feeling of emptiness as his ass contracted around nothing.
“Wow,” he breathed out, and he rolled to his side.
Settling down took a while, and Stiles’ brain occupied itself with thinking over what this part of his exploration meant while his body recovered. He knew now that he very much enjoyed what little he knew about anal play, he was pretty sure that he’d just as much enjoy getting fucked. He was still wary of anything bigger than the smallest plug inside him, but with the other two in the set, he was looking forward to getting to the point of a dick inside him. His own cock twitched despite the recent orgasm and the slight oversensitivity when his thoughts drifted to whose dick he wanted to get closely acquainted with besides his own.
The next few weeks were filled with more experimentation, with his fingers -- he was getting more flexible than he gave himself credit for -- and with the plugs. When he used the vibe for the first time after he was comfortable with the middle plug, he came seconds after his fingers accidentally turned on the vibration setting. By coincidence, that was also when he discovered his prostate, when the vibe brushed against it as he was pulling it out.
“Oh, okay,” he told himself when he caught his breath again.
With his new discoveries, his infrequent encounters with Derek, most of them to Stiles’ relief brief and less awkward than he was afraid of, were getting more and more charged with tension that he was beginning to recognise as sexual. He was growing in confidence, and that gave him the push to try a little flirting. Stiles knew how to smile the right way, how to ‘accidentally’ brush his hand against Derek’s when they were close enough.
At first, and despite their encounter in the sex shop that had to have clued Derek in on Stiles’ attraction, it didn’t seem to work. Derek didn’t show any reactions besides the usual, considerably more friendly than when they first met, friendly even. Still, Stiles was beginning to wonder if he stood any sort of a chance, even if his recollection of their one encounter in the sex shop was firmly lodged in his brain.
“I haven’t seen you back,” Danny said one day out of the blue at lunch.
Stiles blushed as he realized what Danny was referring to.
“Didn’t have the need,” Stiles replied a few beats later. “Only needed lube.”
“I would’ve thought you’d need an upgrade from what you got the last time,” Danny said in a teasing tone.
“You remember all customers’ purchases?”
“Just the ones that are intriguing,” Danny said easily. “Gotta say, you didn’t ping my radar at first, but I can see it.”
He gave Stiles a once-over, enough for Stiles to recall an old conversation -- and the invitation that it involved.
“Before you ask,” Danny said, smirking, “yes, you are attractive to gay guys.”
Chuckling easily at that flashback to another old memory, Stiles shrugged.
“Yeah, I kind of got that in Jungle, thanks,” he said, and pointedly ignored Danny’s raised eyebrow.
“It’s a specific guy you’re after though, isn’t it? One we’re both well acquainted with,” Danny said.
“That begs the question: how well are you acquainted with him?” Stiles asked, not even trying to pretend he didn’t know who Danny was referring to.
“Not as well as plenty of gay and bi guys in town would like to be,” Danny said. “Don’t wait too long, or someone else will go for it.”
Stiles sighed. He was well aware of how attractive Derek was, but it wasn’t like he had ideas on how to do more than what he was already doing. The bell saved Stiles from further discussion, and he and Danny headed off in different directions.
A few days later, the whole pack gathered at Stiles’ house for a meeting, mostly to check in with each other and discuss what they’d been talking about as graduation was approaching. Some of them were heading to college out of town, and that caused multiple conversations about how the pack would work with the distance between them. Once again, Derek reassured them that as long as there was a core pack still in the territory, and as long as they kept coming back for holidays or breaks, none of them would either need to relinquish their place in the pack or find a new one to avoid being Omegas.
“It’s easier for humans, isn’t it?” Stiles asked when people began leaving to go home.
Derek didn’t turn away from the book he was reading, an old journal he was sent from an allied pack that had mentions of his family.
“Leaving, being away from the pack,” Stiles said as he sat down next to Derek.
“As hard as leaving for college would be without a pack. Maybe a little harder,” Derek said, putting the journal on the coffee table. “I only saw one older cousin away from their packs. He just said he missed home.”
“How is it for wolves?” Stiles asked, part curious and part worried about the werewolf members of the pack.
“Jackson could tell you better,” Derek said, and he smirked when Stiles grimaced. “It helped him to be away from here.”
“That’s probably Beacon Hills, though, and not the pack.” Stiles shrugged. “Back then, there wasn’t much of a pack to hang around for. Not like now.”
“True, the pack is stronger. We’re all closer. Jackson, surprisingly, included.”
“You all lost the clique part that you had going when we first met.”
“Yeah well, almost dying and being in danger brings people together, I guess.”
Stiles narrowed his eyes at Derek, and he tried to figure out if the question was genuine, or if there was something behind it that Derek didn’t want to say or ask.
“Hey kid, I’m heading in for an all-nighter,” John interrupted the moment. “We’re a deputy short tonight.”
“Dad, don’t you have minions to do that for you?” Stiles asked, and he grumbled about his Dad’s health under his breath.
“Not tonight. Please don’t hold a party or break the house,” John said, and he walked away before Stiles could respond.
“Like I’d even manage to get anyone here on such short notice,” Stiles muttered under his breath.
His head snapped up when he heard Derek chuckle, because that was still not such a common thing to happen.
“There’s enough of the pack around that I’m sure you’d get a party going,” Derek told him, all laughter from his tone gone. “You’re not the outcast anymore, Stiles.”
“Maybe,” Stiles said, and he shrugged. “I guess I have a few friends in the pack.”
“They’d all show up, if not for anything else, then for the booze.”
“Which I couldn’t get, now that Dad has finally cleared the cupboards out and gotten rid of the whiskey,” Stiles grumbled, and then he looked at Derek with a questioning expression. “Unless you’re friend enough to show up.” He paused, and tried to suppress the insecurity and curiosity in his voice before he asked, “Would you be friend enough to show up to a party held by me?”
Derek was quiet for a few beats, just long enough that Stiles got close to telling him to forget he asked.
“Not for a party, no,” Derek said just as Stiles’ mouth opened.
“Oh? What would you show up for?”
“I’m here already, aren’t I?”
Derek smiled, and Stiles’ breath hitched at the implications and at the way Derek’s face looked with the genuine expression.
“For the meeting,” Stiles whispered, not willing to get his hopes up too high.
“It’s finished, and everyone else is gone,” Derek said. “And yet I’m still here.”
“And my Dad is out for the night,” Stiles said, all chances of keeping his hopes up for where their conversation was going flying out of the window with each word.
“If you wanted a party, you could get them all back,” Derek spoke slowly, like he was letting Stiles mull over the words. “Except for your Dad, of course. Or…”
“Or what?” Stiles felt his heart pounding.
“Or I could stay. For the night.”
Another few beats later, punctuated with Stiles’ rabbiting heart, Derek raised an eyebrow, looking for a response to his suggestion.
“Yeah,” Stiles nodded, almost too eagerly. “Yeah, I’d like that.”
“Got any ideas what we could do with the house to ourselves?” Derek asked, sounding more than a little amused, with a hint of relief.
“One or two, yeah,” Stiles said, unable to hide his blush anymore, because his mind filled with multiple possibilities, all involving his sex shop purchases and very little clothing. And maybe more.
“I’ll be right back,” Derek said then, and before Stiles got a chance to ask or say anything, the front door was slamming open as Derek rushed to his car in the driveway.
He was back before Stiles’ mind reeled back from the fantasies that it dived into. The box in Derek’s hands only brought them back though, and Stiles stood up and nodded towards the staircase. Derek nodded back and followed Stiles upstairs.
“So…” Stiles said when they were in his room, and he sat down on the edge of his bed.
“I’ve thought about it, you know,” Derek said, making Stiles frown at the lack of specifics. “I wondered if you bought anything that day and if this was just your usual curiosity and need to know every detail.”
“I did,” Stiles blurted out. “I did buy something. Not… not what you did, but…”
“Show me?” Derek asked, his pupils wide but the rest of his body seemingly relaxed.
Stiles tried to restrain himself from diving towards the drawer where he kept his toys, but he knew he failed. He heard another chuckle when a pair of socks flew out as he tugged at a box in the back of the drawer. He’d kept his toys there, safe in the knowledge that his Dad was back to trusting him enough to not rummage through his stuff. Now, with Derek’s eyes on him, it still felt like revealing deeper secrets than Stiles ever did but a lot less embarrassing than if he’d ever had to explain them to his Dad.
“Did you…?” Derek started asking, his eyes wide when Stiles opened the lid to reveal the plugs and the vibrator neatly stashed inside.
“Yeah,” Stiles nodded, his cheeks warm and tingling. “Yeah, all of them.”
That confession earned him a choked off gasp from Derek, and when he looked up from the box, he saw that Derek’s eyes were wide open, his irises almost black with the exception of a tiny sliver that was flashing blue.
“I…” Derek started, his voice rough like he was holding himself back.
“I didn’t… you weren’t interested,” Stiles said, processing Derek’s reaction, since it finally hit him. “I mean, I tried to… you never said anything.”
Derek looked down to the floor, and Stiles didn’t miss the dark tint to his cheeks and ears, nor the way his fists clenched.
“You were seventeen.”
Stiles’ jaw dropped, and his brain felt like it was rebooting as he took in that bit of information. His statement was about the time since they ran into each other in the sex shop, and the weeks since. Derek, however, was obviously referring to a period of time a lot longer than that.
“Oh,” Stiles said finally, when the silence dragged on a few moments too long. “My birthday was a few months ago, though.”
“I know,” Derek said, barely louder than a whisper. “I wasn’t sure you were… I saw you at Jungle once, with a guy. But I thought you were figuring things out.”
“I was. I did.”
Derek looked up, and his eyes strayed to the box in Stiles’ hands, almost like there was a question that he didn’t dare ask out loud. Stiles glanced down, and he didn’t bother holding back the smirk.
“That helped, with some things,” he said, and then he looked up at Derek. “I knew I was into guys for a while now, though. Thanks for that, by the way.”
Derek’s eyes widened again, and then he frowned.
“Kinda tough to ignore that all that,” Stiles said with a wave at Derek’s body and face, “was making me feel things. Want things.” He looked back down at the plugs and vibe in the box. “This was more a technical issue.”
Derek raised an eyebrow. “ Technical issue,” he said in a deadpan tone.
“Yeah, preferences and all,” Stiles said, shrugging. “There were things I wanted to know if I was into.”
“And are you?”
“Considering I got all the way up to this one,” Stiles said, reaching for the biggest of the three plugs, “I think I can safely say that I am. Into that, I mean.”
Derek took a step closer, and he tossed the box in his hand on the bed next to Stiles. Then, still in complete silence, he reached for the plug in Stiles’ hand and took it, his thumb rubbing over the surface as his fingers wrapped around it.
“I wondered if you would,” he told Stiles, looking down at the toy instead of meeting Stiles’ eyes. “I thought you might, after the shop.”
“I could,” Stiles started saying, and then he paused to take a breath and brace himself for what he was about to offer. “I could show you? I mean, I’ve never done any of it with… or for anyone. But I could…”
Derek was nodding before Stiles finished his offer, and his fingers squeezed harder around the toy, his knuckles white.
“Please,” he whispered, and it was all the invitation and opening that Stiles needed to hear.
He praised the fact that summer was getting closer, and there were fewer layers that he needed to get rid of. Normally, he’d still be struggling with his hoodie or shirt, but now he had his T-shirt off and flying across the room in moments. His jeans didn’t come off that easily, and Stiles cursed under his breath when he realized that he should’ve taken his shoes off first. Once he was only in his boxers, he paused and looked up at Derek.
“How should I… do you want to....”
Stiles didn’t know what he was asking exactly, but Derek seemed to understand anyway. His own shirt flew in the same direction as Stiles’ had, and when he sat down on the bed, Stiles couldn’t help but stare.
“Yeah, definitely appreciative of the male body,” he whispered, taking in the -- maybe slightly less defined as in the past but still very attractive -- body in front of him. He shook his head then, trying to bring his mind back to what he was supposed to be doing. “Okay,” he said, catching his breath. “How do you want me to do this?”
“Like you do when you’re alone,” Derek said, and his hand moved to Stiles’ thigh.
The contact was electrifying, and yet another reminder of how much Derek was turning him on.
“Can I... “ Stiles said, breaking the moment of silence that followed Derek’s touch. “Is… can kissing be a part of this?”
Derek nodded, and he leaned forward in a flash, his lips warm against Stiles’. It wasn’t a deep kiss, or an urgent one, not like Stiles knew from his short encounters with other guys. There was tenderness to it that threw him off for a moment, but he went with it, realizing and relieved that he wasn’t the only one looking for more than just a quick something .
He did start getting distracted though, so he pulled away. Derek followed first, but then leaned back and watched as Stiles shuffled up on the bed.
“So, uh, I guess I should lose these,” he said, and he tugged on the elastic around his waist.
“If you don’t want to, we can just… you don’t have to,” Derek told him, offering a way out that Stiles really really didn’t want to take.
“No,” he said, shaking his head. “No, I want to. But no one has seen me naked yet; it’s a little unnerving.”
“I’d offer to turn around,” Derek said, and he was smiling again, the tension of the moment breaking. “But then I’d miss the show.”
“Oh, I’m putting a show on now? Is that what it is? Should I start charging?” Stiles joked, his shoulders slumping a little as the nervousness seeped away.
“I’m hoping there are ways that I can repay you,” Derek said.
“You’ll figure it out. Okay, here goes nothing,” Stiles ended in a mumble, and he lay down to pull the boxers off.
Derek didn’t show a sign of surprise when he saw that Stiles’ dick was hard, which Stiles knew was because he could probably smell the arousal from before they even came to the bedroom. What surprised Stiles was that Derek didn’t reach out to touch, but also that he didn’t feel the need to touch himself either.
“I tried like this,” Stiles said, eager to break the silence that was making him nervous more than the situation itself. “But it’s not a good angle, even with the plugs. So I’m normally,” he moved to his front, and pulled his knees in. “Like this,” he finished.
There was the sound of a gulp and a deep breath, but Stiles closed his eyes so he could pay attention to things other than Derek watching him. He pressed his forehead into the arm bent in front of him and fumbled for the bottle of lube that he had on the nightstand. It was cold when he reached back and his fingers brushed against his ass first, which made him shiver a little.
He could feel the way the bed shifted as Derek moved closer, and then he almost jumped when Derek’s warm hand landed on the back of his leg, just below his knee.
“It’s just cold,” Stiles said, his voice a little muffled. “No, keep it,” he added when Derek started moving his hand away.
Besides the tingling sensation caused by being watched, the touch of Derek’s palm added another layer of arousal to the moment. Stiles took a deep breath then and ignored the fact that the lube had only warmed up a little so far. He knew that the first breach of his finger past the rim of his ass was always a little surprising, even though it was his own hand, and he knew what was happening. This time, his own small gasp was echoed from behind him where Derek sat, and Stiles’ hips instinctively moved towards the intrusion. His finger was in to the second knuckle straight away, and he gave himself a second to catch his breath.
He felt Derek’s hand tense and grip a little tighter around his leg, and it was just the incentive that Stiles needed to start moving. Only a few strokes later, he added a second finger, already craving to be filled by more. They slid in easily, partly thanks to the lube on and around them and partly because Stiles had done just this the night before, opening himself up like he made a habit since he got up to the biggest plug. When he paused and pulled his fingers out to reach for the small plug, he realized that it was already against his skin, sliding up the back of his thigh thanks to Derek.
“Can I?” Derek asked, and Stiles slumped a little forward, his ass sticking out a little more with the motion.
“Yeah,” he mumbled, bringing the hand he was using to finger himself forward, and he dropped his head on his forearms when he crossed them against the pillow. “ Please .”
The sensation was different when the plug wasn’t guided in by his own hand. The angle was so much better, the slide in smoother, and when Derek’s knuckles brushed against Stiles’ skin, it brought home to Stiles that he wasn’t alone. He pushed his ass back against Derek’s hand, and his cock twitched when the plug’s widest part popped in easily.
“Oh fuck,” he managed to say before Derek started moving the small plug, in and out and then twisting it a little against Stiles’ rim. It helped the stretch, and it didn’t take long before Stiles started craving more again, knowing that he could take any of the plugs quite easily now.
“Skip the middle one,” he said to Derek in a moment when Derek paused the plug’s movement.
“ Stiles ,” Derek groaned out, but then he pulled the small plug out and ran his fingers over Stiles’ hole. “Are you sure?”
“Yeah, I can… I want you to,” Stiles said, and he moaned when Derek pressed two and then three fingers inside him. “Der, please.”
“You really do like this, don’t you?” Derek was saying while Stiles listened to the cap of the lube bottle click open and then closed. “You want something inside you.”
“Mhm,” Stiles nodded against his arms, and he gasped when the big plug breached past his rim. He could feel the stretch, could feel his muscles clench and relax as the plastic pushed in, and he almost reached down to wrap his fingers around the base of his cock to hold off coming.
He did manage to reel in the orgasm though when he focused on the plug’s movement instead. It didn’t burn, he just felt full, the added sensation of Derek’s finger tracing the stretched rim sending shivers down Stiles’ spine.
“So good,” he said quietly. “Move, please,” he added when Derek stopped pushing the plug in just short of the widest part slipping inside.
“You look so good.” Derek pushed the plug in as he said the words. “I want it to be me, though, inside you.”
“ Yes ,” Stiles whimpered at the thought.
He wasn’t sure, because he had no visual evidence, but he guesses that Derek’s cock was a little thicker than the plug that was inside his ass right now. The thought of being stretched more made him squeeze the ring of muscle in his ass, and he heard Derek’s quiet gasp.
“I want you to do that when it’s me in you, I bet it’ll feel amazing.”
“Der,” Stiles managed to say, and then Derek began moving the plug again, tiny motions in and out, and then the circling and twisting ones that rubbed against Stiles’ walls and brushed the tip of the plug against his prostate.
The way Derek was using the plug to fuck him, Stiles knew he wouldn’t last too long. Not with the added new sensation of another person doing what he only knew from his own experimenting and later jerking off sessions. Having Derek there, feeling eyes on his body, all while his rim was being stretched and his prostate stimulated, was bringing him close to the edge faster than he expected. He was just trying to bring himself to say something, felt his body tense with the imminent orgasm, when Derek stopped and slowly slid the plug out.
“Stiles, babe,” Derek whispered, and he leaned against Stiles’ side to bring his lips closer to his ear. “Can I?”
“Please,” Stiles replied, not needing the full question. “I want you. Please, fuck me.”
Derek let out a small sound that could only be classified as a whimper, but he didn’t hesitate. There was the sound of a foil packet opening, which made Stiles’ mind briefly stop to wonder when and where Derek had a condom, but then he heard the zipper and the rustle of Derek’s jeans coming off. That alone was enough to short-circuit his brain, and he wanted to look . He twisted his head just in time to see Derek rolling the condom over his cock, and Stiles almost drooled at the sight.
“Next time, I want my mouth on you,” he mumbled.
“ Fuck , Stiles, don’t…” Derek said, and he wrapped his fingers around the base of his cock that visibly twitched at Stiles’ words. “I’d say now , but I really want to be inside you. Next time, though…”
Stiles nodded, and then his eyes darted over to the knotting dildo that was still on the bed beside them.
“More things to try next time ,” he said breathlessly, and Derek let out another whimper.
“You’re gonna be the death of me,” Derek said a beat later. “But for now…”
He didn’t finish the sentence, but he moved between Stiles’ knees and brought his hand to Stiles’ ass, sliding two and then three fingers inside his hole.
Stiles shook his head, but didn’t need to say anything, because when he turned his head back to his arms, he felt the blunt tip of Derek’s cock against his rim. Derek moved his hips slowly, his cock slowly pushing inside, past the muscles that Stiles couldn’t help but clench a little at the brand new sensation. It felt different from the tapered plug, the thickness of Derek’s cock the same at the tip as it was at the base. He felt more full immediately, his rim stretched but not uncomfortable.
“Derek,” he mumbled, knowing that Derek could hear the words even though they were muffled. “Don’t tease.”
“Don’t want to hurt you,” Derek told him, and the words sounded like he was biting them back, like he was tense all over from the effort that it took to hold himself from just thrusting forward.
Stiles’ impatience won over, and he put weight on his arms before he thrust his hips back, basically impaling himself on Derek’s cock. They both gasped, and Stiles moved forward just enough to feel the rub against the walls of his ass, then pushed back again, further this time.
“You’re a menace,” Derek said, and he put his hands on Stiles’ hips, at first to hold him still. “Couldn’t wait, could you?”
“We’ve waited long enough,” Stiles said with a gasp. “C’mon.”
Derek chuckled, but didn’t disagree. His hands gripped Stiles’ hips more firmly, and he pulled them closer until his own hips were pressed against Stiles’ ass.
“Is this full enough for you?” Derek asked, and Stiles retaliated to the amused tone in Derek’s voice by clenching his ass.
It sent a shudder down his spine and Derek cursed under his breath, shaking a little in response to the slight vibration.
“Move, please ,” Stiles whispered when Derek stayed still for a beat too long for Stiles’ liking.
“Okay,” was the only response Stiles got before he felt the rub of Derek’s cock against his rim.
They found a rhythm moments later, Stiles pushing his ass back a little just as Derek moved his hips forward. There were no sounds for a while besides their skin meeting at each thrust and cut off gasps from both of them either when Stiles’ ass clenched around Derek’s dick or when Derek pulled out a little more and brushed the tip of his cock against Stiles’ prostate on the slide back in.
It was Derek’s hand moving that tipped Stiles over the edge. Derek’s fingers wrapped around Stiles’ cock and squeezed gently once before moving in a rhythm matching the thrusts of their hips. Stiles came hard, his eyes squeezing shut as his cock pulsed and come fell in streaks against the comforter. He barely registered that Derek stopped moving, but the sudden stillness brought him back to reality sooner than he would’ve had Derek continued fucking him through the orgasm.
“Der, you okay?” Stiles asked, his voice breathless, and his body still shivering from the climax.
“Yeah, I... “ Derek said, but he sounded like he was forcing the words out through clenched teeth. “I’m just gonna…” he started, and he started pulling out.
“No, why, don’t,” Stiles blurted, pretty sure -- despite having lost a moment or two to his orgasm -- that Derek hadn’t come yet.
“The thing ,” Derek bit off, but he stopped moving. “I didn’t think… it never happened before.”
It took a moment for Stiles’ brain to be online enough to put the words together and fill in the blanks. Of course, with that realization came a beat of almost blacking out just at the idea.
“You can?” Stiles asked, fighting the urge to just grind his hips on Derek’s cock.
“Apparently,” Derek still sounded on edge, and not in the way he should be with his dick inside Stiles.
Another beat, and Stiles stopped fighting his own body’s urge. He pushed his hips back against Derek and clenched his ass.
“Do it,” he said, relaxing and then squeezing his muscles again.
Derek growled, but he stopped holding back, and thrust his hips forward again. It only took twice more, and then Derek stilled completely. Stiles gasped when he started feeling the knot form, the width pressing against the walls of his ass in ways he hadn’t even imagined before. He couldn’t feel Derek come inside, but he didn’t miss the full body shudders as Derek leaned forward and against Stiles’ back. The movement changed the angle between them, and Derek’s cock brushed Stiles’ prostate then.
“I can’t… fuck, you’re gonna make my dick want to come again ,” Stiles blurted out, and Derek chuckled, increasing the vibrations of their bodies and making Stiles whimper. His cock was spent, but that didn’t stop it from twitching like it wanted to get hard all over again.
“Here,” Derek tugged on Stiles’ shoulder and rolled them to their sides, out of the damp spot of Stiles’ come.
They both shuddered again, each movement a little too much for their spent and sensitive bodies. Derek muttered an apology into Stiles’ ear, but Stiles shook his head.
“Don’t be sorry,” he said. “That was out of this world.”
Derek didn’t reply at first, but his arms tightened around Stiles’ waist.
“I thought it wouldn’t happen, because it never did before,” Derek spoke after a while of them catching their breaths. “Even when Danny said it did, I thought it wouldn’t. That’s kind of why…”
Stiles frowned, but then his lips tugged up in a small smile.
“DId you buy a knotting dildo for me , Derek?” He asked, and then chuckled.
“Maybe,” Derek muttered against Stiles’ shoulder. “I thought, if it turned out that you’re into that, and I couldn’t…”
“You’re something else,” Stiles said, and he tried to twist his neck enough to at least somewhat face Derek, since they were still locked together by the knot. “You know what the research said about knotting?”
“Obviously not,” Derek said with a huff.
He shifted his hips a little, and Stiles shuddered, muttering ‘asshole’ into the pillow that he pulled closer.
“Do you want to know?”
“It would be nice if you told me,” Derek said, and he nuzzled into the crook of Stiles’ neck.
“There was a ton of stuff online, of course,” Stiles started saying, and he chuckled and shuddered a little at the memories. “Some, you definitely do not want to know,” he continued, ignoring Derek’s reactions to every little movement. “But there was that one book that Deaton was sent, and that had more reliable information. It seems that there have to be feelings involved for a knot to happen. Feelings on both sides. Or three and more, if one was into that. Basically, there have to be feelings from each participant for the other or others.”
“Oh,” Derek said, and his arms tightened around Stiles again.
“So, knowing that, I guess it’s confession time?” Stiles asked, trying to turn his head around again.
“You know,” Derek said, his lips brushing against the back of Stiles’ neck with each word. “I would kind of like to not have my cock inside you when I tell you that I’ve been in love with you since before it was legal.”
He chuckled when Stiles tried to bat at him and failed because of their position.
“You’re such an asshole,” Stiles said loudly, but he wasn’t angry at all. “I can’t believe I love you.”
Derek, instead of retaliating with words, moved just enough to reach Stiles’ lips when they finally managed to turn the right way. Still, the kiss was short and quick, and Derek’s “I love you, too” was whispered into it.
“So,” Stiles said when they got more comfortable again. “How long do you think we’re going to be here?”
“Do you have somewhere to be?” Derek asked, and then he sighed, holding Stiles tight.
A few beats later, Stiles put his own hands on top of Derek’s.
“No,” he said, relaxing fully. “No, I’m good.”