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“Hey, a package came for you earlier,” Stiles says as soon as Derek’s through the door and he blinks, looking up where the other boy is laying with Isaac, the two of them tangled together on the mattress. “Over there,” he mumbles and points to the bed across the room.
Sure enough, there’s a small box sitting on the middle of his mattress and Derek stares at it, thinking that Laura sent him something from home, like she always does. He isn’t too concerned with it, not for the moment, so he drops his bag onto the floor in front of his bed and shrugs out of his jacket, tossing it onto the mattress.
“Aren’t you going to ask who it’s from?” This time Isaac is talking and Derek rolls a shoulder, bending to untie his boots before yanking them off, throwing them to the floor. “It’s from Jackson Whittemore.”
Hearing that name makes Derek pause and he glances at his friends, his eyebrows pulled together. “Jackson?”
“He brought it by, like, an hour ago,” Stiles answers and shrugs, turning over onto his side, his back pressed against Isaac’s arm. “Actually interrupted our fun time.”
“I don’t need to know that,” Derek mumbles and turns, looking at the box with a frown, his stomach twisting into knots. “Did he say anything when he dropped it off?”
There’s a moment of silence, then the sound of bed springs squeaking, and Derek turns just in time to watch Isaac wrap his arms around Stiles, shaking his head slowly. “Just said to give it to you when you got back.”
“There was something jingling around in there.” Stiles grins and Derek scowls at him before sitting on the edge of the bed. “You’re going to open it now? In front of us?”
“Why not?” Derek pulls the box onto his lap and starts to peel the tape off, looking up when Stiles snorts. “What’s your problem?”
Stiles just grins and shakes his head. “There could be something really kinky in there, you know, and you don’t want to corrupt our innocence,” he mumbles and Derek can tell he’s trying hard to keep a straight face.
“Says the guy who was wearing a nurse’s outfit three weeks ago.”
“Hey!” Stiles protests, blinking at Derek. “It’s not my fault you decided to walk in when Isaac and I were playing nurse and patient.”
Making a face, Derek shakes his head and looks down, tearing the tape off of the box before sticking it to the side. He takes a deep breath and pushes the flaps open, staring at the contents in horror.
There, nestled in the bottom of the cardboard box, is a leather dog collar and a leash. A sheet of paper is tucked underneath it and Derek suddenly hates Stiles and Isaac for pushing him into pledging the Alpha frat with them. Especially now that he’s the only one of the three still in the running for a spot in the house.
“What’s in the box?” Isaac asks and if Derek didn’t know any better, he’d say that the other boy is actually interested.
A beat after Isaac says that, Stiles breaks out his “what’s in the box?!” impersonation from the movie Seven and Derek growls. He shakes his head and decides to just show them what’s inside, instead of telling them, feeling a little embarrassed by the thought of saying “a dog collar and a leash”.
Derek lifts the collar out and holds it out before throwing it over onto the other bed, listening to the buckle jingle. He takes the leash out next and his stomach twists uneasily as he throws that over to the other boys. They go silent, the items making little clinking noises as they’re moved around, and Derek takes the note out of the bottom.
“Dude,” Stiles laughs, “this is some kinky shit.”
When the other boy speaks, Derek doesn’t look up or respond to him, just unfolds the note, swallowing thickly. There are only a few lines on the paper and they read: “Tonight, you’re my pet. Wear these, a coat, a pair of boxers, and nothing else. Come to the house at 8 PM.”
Derek sighs and lifts his free hand, pinching the bridge of his nose. “This is some sick shit,” he grumbles and drops the note back into the box before moving it off of his lap.
“What? Why?” Stiles asks, his eyebrows shooting up as he turns to look at Derek, who narrows his eyes at him. “It’s just a dog collar and a leash, what’s the worst that can happen?”
“Oh, I don’t know, Stiles — maybe Jackson’s going to turn me into his personal pet for the night,” Derek answers, his voice borderline angry, and he glares at the other two, who are still playing with the leash and the collar. “Oh and he wants me to come to the house in nothing but a coat, my boxers, and those — those damn things.”
The look on Stiles’ face goes from glee to confusion to something that not even Derek can put his finger on. “Oh,” he breathes and turns, looking at the ring of leather in his hands. “Could be worse.”
“How? Please, Stiles, enlighten me: how could it be worse than that?”
“He could be walking you around campus,” Isaac answers before his boyfriend can and he looks at Derek with a smirk. “Just hope he doesn’t decide to do that.”
A frustrated sigh leaves Derek’s throat and he looks at the clock. He has three hours to come up with a way to get out of being Jackson’s pet and his mind is blanking on an excuse. Derek is torn from his thoughts when Stiles throws the collar and leash back onto his bed, the objects jingling together.
“I’m glad we dropped out,” he mumbles and Isaac murmurs an agreement before they laugh. Derek just closes his eyes and lifts his hands, scrubbing them down his face with a sigh.
Tonight is going to be the worst night of his life, he thinks, and he eventually gets off the bed before grabbing a towel off the rack. When Stiles asks where he’s going, Derek says he’s going to take a shower and leaves the room quickly, the door slamming behind him.
Derek takes the longest, hottest shower he can stand before deciding that he can’t hide out in the bathroom forever. He wraps a towel around his waist after getting out and goes back to the dorm room, still thinking of ways he can get out of what’s going to happen to him later.
Isaac and Stiles are gone when Derek gets back but there’s a note on his desk that says good luck. At the bottom someone — Derek knows that it’s Isaac, from the handwriting — scrawled “be safe” and “wear a condom” along with a smiley face. The thought that Jackson may want to fuck him makes Derek’s stomach flutter.
For the next two hours, Derek lays on the middle of his bed in just a pair of boxers, running a finger along the width of the collar. It could be worse, he guesses, and he prays to every god he knows the name of that Jackson isn’t planning on parading him around campus.
When seven thirty rolls around, Derek gets out of bed and goes over to the small closet he shares with Stiles. He rummages through their things before picking out a trench coat that must undoubtedly be his roommate’s. After trying it on to make sure that it fits, Derek grabs the collar and puts it on, his fingers shaking as he buckles it.
Derek pulls on his boots, laces them, and grabs his cellphone before shoving it into one of the pockets of the coat. He picks the leash up and wraps the leather around his fist a few times as he goes to look at himself in the mirror: the coat is unbuttoned and the black from his boxers and the collar contrast against his skin. It makes him shudder and he rolls his lower lip between his teeth before leaving.
On his way out of the dorm, Derek buttons the coat up and hooks the leash through the silver hoop on the collar, tucking it into his jacket as he walks. The night air is cold and he shivers, pulling the collar of the jacket up, shoving his hands under his armpits as he walks across campus.
The walk to the frat house takes Derek twenty minutes and he’s a shivering mess by the time he gets there. His teeth are chattering in his head and he’s almost certain that he can’t feel his toes, but that doesn’t stop him from going up the porch steps. It doesn’t deter him from ringing the doorbell and, even when he hears the chime echo through the house, Derek stays rooted to the porch, waiting for someone to answer.
Jackson comes to the door a minute later and he opens it, looking as smug as ever. He’s grinning from ear to ear and, for once, not wearing what Derek, Isaac, and Stiles deemed his “douche outfit,” but a pair of loose-fitting jeans, a gray t-shirt, and his varsity jacket.
“Good to see you didn’t chicken out, Hale,” he says and motions for the other boy to come in and Derek’s more than a little thankful when he steps into the house. The place is warm and he revels in it for a moment, his tremors fading slowly.
“What do you want me to do?” Derek asks, his voice shaking slightly as he turns to look at Jackson, licking is lips quickly.
The senior shakes his head and clicks his tongue. “That’s not how you talk to me, now is it?”
“No.”
“No what?” Jackson asks, looking at Derek expectantly.
Derek grits his teeth together and says, “No sir.”
“Good boy!” With that, Jackson lifts a hand up and ruffles Derek’s hair, even going so far to scratch behind his ears. “Who’s my good boy?”
Nothing.
“Answer me, Hale.”
“I am, sir,” Derek grits out, clenching his jaw when he feels Jackson’s hand in his hair, fingers behind his ear.
For the first time, Derek notices that the house is quiet and he wonders if they’re the only ones there or if the rest of the brothers are watching them from the shadows. He decides that he doesn’t care and that he just wants to get the night over with.
“Take the coat and boots off,” Jackson says and he steps back, hands shoved into the pockets of his jacket. “Then get on your knees and follow me upstairs.”
A comment rises up from Derek’s throat but he lets the words die on his tongue, not seeing the point in arguing. He unbuttons the coat and peels it away from his body, turning to hang it up on the rack. Next, he bends and unties his boots, dropping them onto the floor in a pile with the others.
Derek hesitates for a moment and then turns around, sinking to his hands and knees in front of Jackson, the leash laying on the floor underneath him. The senior bends and grabs it, looping his hand through the handle before whistling.
Then they’re walking up the stairs and Derek bites back curses when his knees knock against the edge of the steps. He walks diligently behind Jackson and breathes a sigh of relief when they finally get to the top of the staircase.
Jackson’s room is at the end of the hall and Derek’s knees are aching by the time they get there and he really hopes the senior doesn’t keep him on the floor for much longer. When the door is open, they walk into the room and Derek’s knees scrape against the carpet and he whimpers.
“Aw, what’s that?” Jackson asks and stops, squatting in front of Derek as he lifts his free hand, cupping the other’s chin. “What’s the matter boy?”
When Derek opens his mouth to answer, Jackson tugs the leash roughly and mumbles, “No talking. When you’re in this room, you’re not allowed to talk unless I tell you to. Do you understand? Just nod or shake your head.”
Derek nods and swallows thickly.
“Good boy,” the other boy murmurs and he smiles “Now, what’s the matter? Is it your knees?” Derek nods and whimpers again. “I’ll remedy that later but, for now, you’ll have to stay on them.”
Great, Derek thinks as he watches Jackson. His eyes never leave the other boy, not even when he’s standing up, and when Jackson tells him to sit, Derek shuffles back so he’s sitting on his heels.
A smirk stretches across Jackson’s face and he moves a hand to Derek’s hair, ruffling it before going to his ear. He scratches it again and, despite his better judgement, Derek actually tilts into the touch.
Jackson grips the leash tightly and he tugs Derek forward, causing him to fall back onto the ground and he laughs. “Come closer, pup,” he says and Derek hates him so much in that moment. But, he listens, and shuffles forward on his knees, settling back on his heels.
Once Derek is closer, Jackson drops the leash and pulls his jacket off, throwing it onto the floor somewhere. He tugs his shirt over his head next and lets it fall to the carpet beside them, dropping his hands down to undo his jeans.
Derek’s eyes widen as he watches Jackson and he swallows hard, his stomach twisting with nausea. His gaze follows the path of the senior’s jeans as they slip down his legs and he grits his teeth together. Okay, so, things may have just taken a turn for the worse and Derek whimpers quietly.
“What’s wrong?” Jackson asks, kicking his jeans away before hooking his thumbs underneath the waistband of his boxers. “What did you think was going to happen tonight? Answer.”
After a moment of hesitation and biting his lower lip, Derek finally answers: “I thought you were going to make me do shit for you, not be your sex slave or some shit like that.”
“A — you’re not going to be my sex slave, alright? I want you to want this as much as I do because, I may be an asshole, but I’m not the kind to do anything without someone’s consent,” the senior answers, tugging his underwear down before letting it slide to the floor. “And B — I’m going to make you do other things for me but this is high on my list.”
With his heart in his throat, Derek nods and keeps his eyes on Jackson’s face for as long as he can. He doesn’t want to look down, doesn’t want to make the older boy think he’s actually curious, and he swallows, his throat working around the collar.
Jackson comes forward and puts his hands on either side of Derek’s face, gently swiping his thumbs over the other’s cheekbones. “Now,” he says and breathes deeply through his nose before continuing, “suck my cock as well as you can. Then maybe I’ll give you a treat. You want that, don’t you?”
For a second, Derek wants to shake his head but all he can do is nod, bile rising in his throat as he thinks about having Jackson’s dick in his mouth. He swallows it back and finally looks down at the other boy, biting back a gasp.
“You can touch me,” Jackson says and Derek looks up at him through his lashes, suppressing a snort. The senior is looking at him impatiently, his eyebrows moving as if to say ‘what are you waiting for’ and Derek sighs.
Lifting a shaky hand, Derek wraps it around Jackson’s cock and strokes him slowly, feeling the other boy get hard. He swallows and tries to think of things that are unappealing: walking in on his uncle Peter having sex with his English teacher in twelfth grade; the lunch ladies that worked in his elementary school; the health pictures he saw in Laura’s medical books.
But nothing works. All Derek can focus on is how heavy and hot Jackson feels in his hand now and his mouth is watering. He looks back up at the other boy, smirking when he sees that his eyes are closed, and moves forward, licking across the head of Jackson’s cock.
“Fuck.” The word comes out in a breath and Derek feels smug, smirking a little more before taking the head in his mouth. He sucks slowly, stroking the length languidly, moving his free hand along the outside of Jackson’s thigh.
A hand moves to the back of his head and, taking that as encouragement, Derek opens his mouth to take more of Jackson. He gets half of the senior’s length between his lips and starts sucking slowly, hollowing his cheeks as he pulls off. As he does this, Derek wonders, in the back of his mind, if Jackson thinks he’s never done this before and he laughs.
Jackson’s fingers are tightening in Derek’s hair and he decides to take the plunge. He opens his mouth, relaxes, and takes Jackson into his mouth completely, gagging a little when he feels the head of his cock hit the back of his throat.
That’s when Jackson makes a strangled noise and Derek shudders when he hears it, sucking the other boy nice and slow. He pulls off, leaving just the head between his lips, and strokes the shaft quickly. The noises he pulls from Jackson’s throat actually make Derek’s cock harden in his boxers and he tries to ignore what this is doing to him.
“How — where’d you learn to do that?” Jackson asks, breathless, and Derek rolls a shoulder before sinking down again, taking the other to the root. He swallows around him and works his tongue along the underside before pulling off. Derek looks up at Jackson and licks his lips, stroking him harder, thumbing across the head on every upstroke.
After giving himself a moment to breathe, Derek moves back in and sucks Jackson’s cock even harder. He bobs his head up and down, running his tongue along the head and around the crown before sucking the entire length back down.
From the way Jackson is moaning and bucking his hips, Derek knows that he’s getting close and he swallows around the senior again, holding him in his throat before he has to pull off. His own breathing is wrecked and he coughs a little, his hand slicking up and down Jackson’s shaft.
Jackson gasps and opens his eyes, looking down at Derek. “Fuck,” he breathes and gives a crooked smile before reaching a shaky hand down to grab the leash. “On your feet.” As he speaks, Jackson gives the leather a tug and Derek holds onto the senior’s legs to keep himself from falling forward.
It takes Derek a moment to push himself to his feet and he licks his swollen lips, grinning at Jackson. Before he knows it, the other boy is leaning in and kissing him, his lips moving roughly against Derek’s. The kiss throws him for a loop but soon Derek is responding, kissing Jackson back just as eagerly, his hands curled at his sides.
When they ease apart, Jackson bites Derek’s lower lip and tugs him over to the bed before shoving him down onto the mattress. He throws the leash beside him, the leather half laying across his chest, and he moves his hands to Derek’s boxers. Jackson tugs the fabric down and throws it somewhere behind him before stepping back.
“Turn around on the bed and get on your knees, facing the headboard.”
Derek bites the edge of his lip and moves like Jackson told him, his body trembling as he dips his chest toward the bed. He watches the other boy move around the bedroom and shivers with anticipation, letting out a small whimpering noise.
A few minutes later, Jackson comes back to the bed and climbs onto the mattress behind Derek, moving a hand along the back of his thigh. He pops the top on something and a moment later, a slick finger is pressing against Derek’s entrance, causing him to yelp. Even though he saw this coming and he knows what’s going to happen, Derek’s body goes rigid and he holds his breath.
The tip of Jackson’s finger pushes inside of him and Derek curses. Which gains him a sharp smack on the ass and he whimpers, chewing on his lower lip to keep himself quiet.
“You ever done this before, Hale?” Jackson asks and Derek thinks for a moment, shrugging his shoulders. “What’s that supposed to mean? Answer.”
Blowing out a breath, Derek turns to look at Jackson over his shoulder. “I have fingered myself before but no one’s ever fucked me,” he answers.
“And why not?”
“Because I’m more of a top,” Derek says and growls, feeling the entire length of Jackson’s finger slip inside of him. “Son of a bitch!”
Jackson grins and works his finger in and out slowly. “You can go back to not talking now. Unless it’s a curse, my name, or something you’re begging for, I want you to keep your mouth shut,” he says and pulls the first digit out, only to add a second. “Understand?”
Derek nods his head and clenches his eyes shut, sucking in a deep breath when he feels Jackson’s fingers slide into him. A familiar burning ache flares up and Derek grinds his teeth together, breathing deeply through his nose. He curses again, feeling the digits press into him all the way, and moans when Jackson starts scissoring them.
“I’ve thought about fucking you since night one,” Jackson murmurs, moving his free hand along Derek’s leg. “And the other brothers were making their pledges do something like this, so I figured it would be a perfect opportunity to fuck you.”
A shudder passes through Derek’s body and he starts pushing back against Jackson’s hand, silently asking for more. His wish is granted when the other boy presses three fingers against his rim and he lets out a loud curse, feeling them sink in quickly.
Grinning, Jackson strokes Derek’s flank and mumbles, “You’re going to love being fucked. Can’t believe no one’s ever done it.”
“Jackson,” Derek moans and gasps, the fingers inside of him crooking as Jackson pulls them out slowly. “Fuck, oh — oh god, Jackson.”
“What did I say, pup? Answer.”
A gasp escapes and Derek drops his head between his shoulders. “I’m not supposed to — ah — talk but how in the fuck do you expect me to.. to be quiet?”
“You’re right, I don’t expect you to. So we’ll change the rules,” Jackson replies, slamming his fingers into Derek quickly. “You talk, I smack your ass once for every word you say. How does that sound?”
“Good,” Derek answers, almost too quickly, and he sucks in a sharp breath, feeling Jackson’s hand come down on his skin. His cock is throbbing between his legs and he wants Jackson to fuck him already. “Will you fuck me already?”
Five blows.
Derek groans and grits his teeth together, reveling in the painful burn that spreads across his ass. He whines in disappointment when Jackson pulls his fingers out and he’s left with an empty feeling.
A long moment passes before Derek feels the head of Jackson’s cock against his entrance and he whimpers desperately. He stays still, though, and doesn’t move until he feels half of the other boy’s length inside of him. Then he starts to push back, tries to get Jackson to push in all the way, and nearly screams when the senior slams into him.
Jackson’s hands rest on his hips and he starts thrusting in and out quickly, not giving Derek time to adjust to his cock. Pain comes along but it isn’t anything he can’t deal with, so Derek just bites his lip and moans around it, his hands fisted into the sheets.
“God,” the senior groans, “you’re so tight.”
If Derek wasn’t currently being fucked relentlessly, he would have laughed but all he can do is moan in agreement. He drops his head onto the bed, laying it just under his forearms, and he arches his back, pushing against Jackson.
The thrusts slow down and Derek whimpers, gasping when he feels Jackson’s cock drag out of him before sliding back in slowly. A hand moves down to his ass and Derek yelps at the smack Jackson gives him.
Keeping one hand on Derek’s ass, Jackson moves the other underneath him, grabbing the leash. He pulls it around and lets the leather settle on the other boy’s back, the handle wrapped around his hand a few times.
“Derek,” Jackson gasps as he pulls out and slams back in, giving the leash a sharp tug. He can feel the other boy tightening around him and bites down on his lower lip, slapping his ass quickly. “You feel so — so good.”
A strangled moan escapes Derek’s throat and he lets out a broken laugh before mumbling, “So do you.”
Three more blows come down on his ass and Derek yelps after each one, his ass burning from the smacks and from how hard Jackson is fucking him. He loves it, though, and pushes back, whimpering whenever he feels the leash being tugged.
When he feels himself getting closer to coming, Jackson pulls out of Derek and takes the condom off, throwing it somewhere over the edge of the bed. He strokes himself and moves his hand down, sinking three fingers into the other boy.
Jackson strokes himself and fingers Derek at the same pace, leaning down to press kisses against the small of his back. “Stroke your cock for me,” he mumbles, separating his fingers as wide as he can.
“Fuck!” Derek moans and moves a hand down, wrapping his fingers around his cock before giving it a tug. He’s so hard and there’s already precome beading on the head, his thumb swiping through it as he strokes up.
The fingers inside of him keep moving and Jackson crooks them, pressing the tips against Derek’s prostate. That makes his entire body shudder and he gasps, gripping his cock tightly before stroking himself again, his pace erratic.
Behind him, Jackson is panting and gasping, sweat dripping across his skin as he strokes his own cock and continues to finger Derek. It’s hard to keep up with both of them but he manages, sometimes stilling his fingers inside of the other boy in favor of stroking his cock harder.
“Gonna…” Derek starts and gasps
“Gonna what, pup?” Jackson asks, his voice breathless.
Derek doesn’t get to answer before he comes, gasping Jackson’s name loudly and panting. He comes on the sheets underneath them and his body trembles, a thin sheen of sweat covering his back.
Feeling Derek’s muscles tighten around his fingers and listening to his breathing and noises, Jackson bites his lip and keeps stroking. After a handful of strokes, he comes and points his cock so he shoots on the other boy’s back.
Jackson gasps and moans, whimpering as his hips stutter and his orgasm subsides. He looks down at Derek’s back and swallows, licking across his dry lips.
“Dude…”
“Hmm?” The senior hums, smirking lazily.
“Did you come on me?” Derek asks in a broken voice and all Jackson can do is laugh in response as he moves a finger through the come on Derek’s skin. “That’s fucking gross.”
Another laugh bubbles up and Jackson falls onto the mattress beside Derek, shaking his head. “Had to come somewhere,” he breathes.
“Not on me.” Despite the words, Derek isn’t angry or disgusted and he actually smiles as he tries to catch his breath. He lays on the edge of the bed on his side, facing Jackson, and licks his lips. “Was that really a hazing ritual — or were you just trying to get into my pants?”
“Trying?” Jackson snorts and rolls his eyes. “I succeeded, Hale. And it was a hazing ritual… just gone a little too far.”
Derek inhales deeply and shakes his head. “So do I still have to do more shit for you or was letting you fuck me enough?”
Nothing.
“Jackson?”
“What?”
“Answer me,” Derek mumbles.
Huffing, Jackson shrugs and runs his dry hand down his face. “You still have to do some stuff for me. My room needs to be cleaned, my Porsche washed, and my laundry needs to be done,” he answers.
“I”m not doing any of that shit.”
“You will if you wanna be an Alpha,” Jackson points out with a grin and he sighs, sitting up before moving off of the bed. He grabs a towel from the hamper and comes back to clean the come off of Derek’s back. “You can start by washing those sheets.”
A groan escapes Derek’s lips and he snorts before rolling off the mattress. He strips the bed of the dirty sheets and rolls them up into a ball before throwing them onto the floor. Once that’s done, Derek turns to look at Jackson, his eyebrows lifted.
“What?” Jackson asks, narrowing his eyes.
“Does this mean I’m in the frat or are you going to make me get to the end of the pledge period before telling me I’m not a good fit?”
Jackson licks his lips and shrugs. “You’d be a good fit for us but I’m afraid I’d fuck you every night and that would distract me from my schoolwork and partying,” he mumbles and winks, grinning.
“Fuck you.” Derek laughs and unhooks the leash from his collar, throwing it onto the bed. He bends to pick his boxers up and tugs them on, wincing as he moves, pain flaring up along his backside. “God, don’t fuck me that hard ever again.”
“So… there’s going to be a next time?” Jackson quirks a brow and grins, looking so hopeful that it actually makes Derek laugh.
Shrugging, Derek grabs the dirty sheets and moves to the door, looking back with a smirk. “Maybe,” is all he says before leaving the room and going down the hall, wincing as he makes his way down the stairs.
There are worse things that could happen, Derek thinks as he shoves Jackson’s sheets into the washing machine, and he can only imagine what the frat brothers are going to make them do next. Maybe pledging wasn’t such a bad idea and if he makes it into the frat, he’ll definitely thank Stiles and Isaac.
Even if he doesn’t, Derek thinks he’s going to thank them either way because he sees something happening between him and Jackson. It might not be a relationship or even a friendship but he can see them fucking each other on a regular basis.
And that is enough to make Derek keep going with the pledge process.