Stiles shook his keys out into his hand from his jacket pocket, hunching his shoulders against the cool breeze tickling the back of his neck. It was mid-winter and the breeze had taken on a certain bite when it was able to find available skin. It was nearing three a.m. and he’d been finishing up some paper organization in his office at the university’s library. The job had been bigger than expected and he was surprised to see the time when he’d finally found an allowable stopping place in his work. His body was sore from being bent over the keyboard and his eyes tired from the bright overhead lighting. All Stiles wanted to do was find himself upstairs in his bed, wrapped up in his blankets and sheets, sleeping like a baby.
These thoughts warmed him as he pulled off his outmost layers of clothing to hang on the back of the couch. His feet trudged upstairs as his brain kept imagining how good the mattress would feel as he sunk into it and how soft his pillow would be against his cheek. He pushed open the door to his bedroom only to stop in surprise. There was already someone else enjoying the plushness of his pillow and the soft luxury of his mattress. That someone was more than welcome to it, of course, but this was the first time in their six months of dating that he’d actually taken the liberty of sleeping there or being in Stiles’ apartment before they’d seen each other in the day. It was a complete surprise for Stiles to find Derek Hale sleeping in his bed when he hadn’t been the one to tuck him in there.
His thoughts stalled out momentarily as he took in the scene in front of him. Derek was sleeping on his stomach, as he was want to do, one knee hitched up over a pillow and the other straight. One arm curled under another pillow that was beneath his head while the other was curled around Stiles’ pillow which was being half smooshed under his muscular chest. Derek was a pillow hog and left to his own devices would be completely surrounded by pillows. Stiles let his tired eyes trace down the rippled planes of Derek’s back and down the valley of his spine. He loved Derek’s back, loved when Derek was on top of him and he could push his fingers into the meat of his muscles to hold on or pull himself tighter. He loved when Derek was under him and he could drape himself against Derek’s expansive shoulders, his arms snaking under Derek’s to feel the fur on his chest and then up to grasp his shoulders as he pulled Derek’s body back into him while he gave sharp upward thrusts.
Those memories were definitely perking the interest of a specific part of his lower body which had not been worked to the bone today. Stiles eyes traveled farther south to appreciate Derek’s fine, fine ass when he felt every ounce of blood north of his belt suddenly start rushing into his cock. Derek was wearing girl panties. They definitely were not men’s briefs as Stiles mind has originally surmised and they were not the erotic, lace underwear Stiles and Derek had previously discussed wearing for one another…. These were girl panties. They were white cotton with the miniature scalloped edging next to the elastic of the legs and waist. They had little pink and grey foxes printed on them. They were the kind of panties you’d find on someone a hell of a lot more innocent than Derek Hale, but Stiles’ physical reaction to them was undeniable.
Practically purring, Stiles knelt on the bed and crawled into the space between Derek’s legs. He smoothed his hands up the toned, hairy legs as he felt Derek start to shift into wakefulness. Lowering his head, Stiles rubbed his cheek against the soft cotton of the underwear, turning his head to bite the flesh through the material, worrying at it for a moment before letting go. A groan from somewhere near the head of the bed graced his ears about the same time he felt Derek’s fingers comb through his hair, even as Stiles smoothed his hands under the leg bands to kneed Derek’s cheeks.
“So I take it you like them?” He heard Derek ask, voice breathy and gruff with sleep and arousal. Stiles hummed a sound of approval as he sat back on his heels to begin shucking off his clothes.
“Where did you get them?” Stiles asked. Derek rolled over onto his back and ghosted his hand down his torso, smirking as Stiles eyes tracked the movement even as he unbuttoned his shirt. Stiles swallowed thickly at the sight of Derek’s swollen length straining the cotton fabric. Derek just rubbed his fingers over the head while he watched Stiles undress, licking his lips when Stiles started in on the button and fly of his pants.
“Maybe I borrowed them from Malia…” Derek smirked. Stiles scowled down at him playfully, throwing his pants at Derek’s face. He caught them and laughed, throwing them over the side of the bed.
“Ugh, don’t talk about your cousin in bed. You’re going to make my dick sad.” Stiles leaned forward to kiss his boyfriend, who decided to stop playing with himself and to start playing with Stiles instead. The feel of Derek’s large, warm hands tugging up and over his quickly hardening prick made Stiles want to swoon.
“Well I guess I’ll have to do something then to make him happy.” Derek whispered against Stiles’ lips as he pulled Stiles up by his hips until he was straddling his chest. Stiles watched as he bent and gave open mouthed kisses to the crown of his cock before sucking in the first few inches. Stiles hips smoothly rolled forward of their own volition, thrusting slowly in and out between Derek’s lips. He kept his thrusts shallow, and Derek rewarded him by playing with his slit and along the ridge of the head with his tongue liberally.
“Well…” Stiles started breathlessly, having to pause as Derek wrapped one hand around the length he didn’t have in his mouth and began to jack him slowly in a tight grip. “That definitely makes him happy. Fuck.”
Derek only hummed, pulling Stiles closer and deeper into his mouth.
“FUCK!” Stiles started in surprise, throwing out his hands to catch the headboard so he didn’t tip over and kill his boyfriend. Derek just swallowed around him, rubbing his hands up Stiles thighs. Stiles felt himself being tipped closer and closer to the edge, his orgasm building low, behind his balls, drawing him tight.
“No, no, no wait!” Stiles squeaked, pulling back from Derek’s mouth and grabbing himself around his base to stop from coming. He huffed out a few breaths, still hovering over Derek’s chest and holding onto the headboard for support.
“What? What?” Derek asked, alarmed.
“I want to…” he started, pausing to drag in another breath. “I want to mess up your panties and I know I won’t be coming twice tonight.”
“Oh” Derek replied, smiling and rubbing his hands up Stiles thighs and stomach. “So what do you want to do to me?”
Stiles moved down so he was laying on top of Derek, their erections sliding against one another as he kissed into Derek’s mouth.
“I want to rim you til you blow your load all in the front of these ridiculously ridiculous, sexy, little, panties….” He paused to grind hard against Derek’s cloth covered cock, biting Derek’s bottom lip as he did so. He was rewarded with a gasp, followed quickly by a groan. “…then I want to fuck you while you’re wearing them.”
“Yes, why aren’t you already doing that?” Derek panted into Stiles mouth, writhing underneath him.
“Just wanted to let you know the game plan, babe.” Stiles responded, sliding sideways off Derek’s chest. “Turn over and get on your knees.”
Derek complied quickly, resting his head on his folded arms even as he stuck his ass in the air. Stiles situated himself once more between Derek’s legs and gazed. Fuck, those panties were so dirty to him for some reason. Smoothing his hands over Derek’s cloth covered ass cheeks, he bent his head closer. His tongue left a wet spot, saturating the cotton easily with his saliva, as he rubbed the flat of his tongue over Derek’s hole through the underwear. He heard Derek’s breath hitch above him as he worked over the rim lightly with his tongue through the underwear. Drawing back, he gazed at the wet spot that was slightly transparent, rubbing his thumb over the material while he looked and playing with the furl. His own cock was throbbing the longer he stared at the wet spot he’d made, and he smoothed his hands back up to drag the underwear down enough to expose Derek’s hole.
Stiles bent back in, fingers splaying over Derek’s cheeks to pull him wide while Stiles pointed his tongue and circled the tightened flesh. He teased with filthy, sucking kisses around the rim and then soothed with wet, broad strokes over the hole, over and over. He started pushing in the point of his tongue slowly, letting go of one of Derek’s cheeks to reach around and palm Derek’s hard-on through the front of the panties. He loved that Derek’s leaking cock had made a wet spot over the cotton soaked head. It took all this control not to flip Derek over and suck the material into his mouth to taste it.
Derek was making small desperate grunts, his hips starting to shove backwards towards Stiles face as he thrust his tongue as deep as it would go. He made his hand slide only once more over Derek’s erection before bringing it back. He gently pressed in one finger, his tongue sliding in beside it to help loosen the wring of muscle. One his finger was firmly encased in the velvet, hot hole, he bent it and began a slow thrust in and out as he sought Derek’s prostate.
“Oh FUCK!” Derek shouted, followed by a hard thrust backwards was Stiles best signal when he found the magic spot. He pulled his finger back and pushed in another, making sure to hit the same spot while he licked and sucked the muscles around his fingers. As he scissored his fingers to tap alternately against Derek’s prostate, he sat back to watch as Derek fell apart in front of him.
Stiles’ cock was dark red at the tip, leaking precome profusely. He used his hand to smear the sticky liquid around his head and then around his shaft as he played with himself. Derek’s cries were getting much more frantic and Stiles could see his toes starting to curl into the bedsheets as his hips pushed themselves harder against Stiles hand.
“You gunna come for me, big guy? Gunna mess up the front of your panties for me?” Stiles asked, making sure to hammer both his fingers against Derek’s prostate even as he teased himself.
“Oh God, Stiles. Fuck, fuck, fuuu----“ Derek’s body curled into itself, the muscles in his ass fluttering around Stiles fingers even as he kept rubbing over the magic muscle. Derek was keening and when Stiles withdrew his fingers and snaked them around to the front of Derek’s groin he was rewarded with the warm, sticky feeling of come coating sliding around the inside of Derek’s panties.
“Mmmm Derek, you did so good for me.” Derek could only groan out an acknowledgement. Stiles was leaning over him and reaching into the bedside drawer so retrieve the lube. He slicked up his cock and with some and then smeared the excess over and inside of Derek’s loosened asshole.
“I’m gunna fuck you now, Derek.” Stiles warned, lining his head up and pressing in slowly. Derek’s ass swallowed the head and when Derek bore down, Stiles felt watched himself sink in further. His breath hissed between his teeth at the exquisite feeling of Derek’s tight ass around his cock.
“Fuck, baby, I’m not sure I’m going to last that long.” Stiles grunted out, starting to pull out and push back in at a slow steady pace. Derek hummed beneath him and moaned when Stiles worked himself particularly deep. “You like it when I’m in you deep, Der?”
“Yeah, yes. I fucking love it” Derek answered, his body rocking back into Stiles, his hips working to grind Stiles cock into ever part of him.
“Fuck. Then come here.” Stiles grunted out, laying himself over Derek’s back and then pulling them back so that Derek was sitting in his lap. From this position, Stiles could grind upwards in short, stabbing thrusts and Derek could keep him deep. Derek rolled his hips over him, riding him even as Stiles worked him over. Stiles teeth bit into the meat of his shoulder and back, his hands scratching down his chest and pinching his nipples. His hand even strayed down into the soggy mess of Derek’s panties, palming Derek’s half hard cock.
“Goddamn, you in these panties. Fuck Derek. Ung… You always fucking know what I want. You’re so good to me. Fuck, I can’t wait to mess up your little girl panties. You did such a good job on the front, I’m going to finish the work on the back. I’m so fuckin’ close. Do you want me to come in your panties, Derek? Do you want to get your asshole all messy with my spunk and then rub your good girl panties in it?” Stiles was babbling, but he could feel his balls tightening and his orgasm building quickly as he pushed himself in and out Derek quickly.
“Yeah, fuck em up, Stiles. Ruin them.” Derek moaned, leaning away from Stiles body to bend over with his ass in the air again, weight resting on his shoulders as his hands came back to hold his cheeks open in invitation for Stiles. Stiles gasped and pulled out, hand stripping his cock quickly, his eyes trained on Derek’s empty, fluttering hole. The first spirts of come landed inside the quickly closing sphincter, but the rest striped over Derek’s taint and cheeks. When Stiles had milked himself though, he brought a hand out and began smearing his come over Derek’s exposed backside. When he was finished, he pulled the panties up and pressed them in place, noting the wet spots that seeped through.
“You like?” Derek asked, voice sounded wrecked as he let his knees slide back so he could lay on the bed.
“I love. God, you’re amazing” Stiles answered, moving his body so he could lay beside his boyfriend. He cuddled close, kissing Derek’s shoulders even as his hand rubbed over the damp cotton of Derek’s underwear.
“I’m going to go get cleaned up” Derek sighed, turning to give Stiles a thorough, lingering kiss before scooting off the bed and heading towards the bathroom. Stiles grinned and moved into the warm spot where Derek had been laying, thinking that he had the best boyfriend in the entire world.