Derek wanted to let his head fall back, close his eyes, and drift off into an easy, brain-meltingly amazing orgasm.
But Stiles was knelt between his spread legs and was slurping on his cock, making the most indecent noises with his mouth as he sucked and rolled the head of Derek's dick like a lollipop. Derek couldn't look away even if he wanted to.
Stiles also had one hand wrapped up in Derek's tie, keeping him from raising his head while Stiles' other hand alternated between stretching himself open and jerking himself off. The hand with the tie didn't have a tight grip; Derek could easily reach up and pull it over his head, but the second Stiles told him to leave it on when they started stripping their clothes off Derek was half-hard.
He knew Stiles had a thing for Derek in a suit. Knew it from before they started this likely very ridiculous affair. Stiles would watch him as he walked around the office. Once he had to stop at Stiles' desk to ask a question and when Derek leaned in to speak Stiles' eyes followed his hand as it smoothed down his chest to flatten his tie.
Derek paired Stiles' gaze with his memories of Stiles biting his own lip when he concentrated, of his long fingers stroking his chin, of the fucking pens he destroyed with his mouth. Derek paired those images and imagined himself making Stiles respond those ways—what he'd say, how he'd react, the sounds he'd make...
The night they hooked up at Jungle wasn't planned, not by Derek. But that day was his breaking point because it found him frantically jerking off in his executive bathroom before a meeting with a very important client to his family's firm.
The bizarrely named Stiles Stilinski was in his head and now, apparently, in his cock and Derek needed to get off, in a way he couldn't remember feeling since his own college days. Finding Stilinski at the club, dancing so enthusiastically that his t-shirt stuck to his light musculature from sweat, and the colored lights bounced off the sheen on his skin making him look ethereal—it was a sign for Derek.
"I could ... do this... all night," Stiles mumbled around Derek's cock, looking up so Derek could see the shiny lines of spit all over Stiles' chin. Derek jumped against Stiles' cheek and he let out a jagged breath he didn't know he was holding. Stiles grinned and started to duck back down but Derek caught him lightly by the chin.
"As tempting as that really is, I need more of you," Derek told Stiles in a husky tone. Stiles grinned and gave Derek's dick one last lick that drew a strangled moan from Derek before slithering his way up Derek's body so their chests were pressed together.
He was straddling Derek and making little circles with his hips so Derek's cock was hot against Stiles' entrance and Stiles' dick was rubbing on Derek's abdomen.
"Y'know," Stiles panted. "I could get off like this, just my cock sliding across you. It's like you're fucking ribbed for my pleasure." Stiles groaned as he shifted on top of Derek faster.
Derek could feel his stomach being coated with Stiles' pre-come and his hips thrusted upward sharply. His body was unconsciously trying to push against Stiles, eager to sink in deeply and be lost in him.
"That can definitely be arranged but at the moment there are more... pressing matters," Derek replied, as evenly as possible while Stiles kept moving and his lips were seeking out Derek's sensitive earlobes.
"Ever the diplomatic professional, hmm Mr. Hale?" Stiles murmured against Derek's ear.
Derek shuddered and wrapped his hands around Stiles' lithe waist, feeling something break inside himself. "It's all I can do to not shove myself balls-deep into your ass, flip you over, and fuck you until you can't remember your name," he growled, closing his eyes with his face pressed into Stiles' neck. Derek breathed deeply and registered the tiny changes in Stiles' body as Derek's words washed over him.
Outwardly, though, Stiles barely reacted. A slow smile slid across his lips as he leaned back far enough to look Derek full in the face.
"Why didn't you say so?" Stiles asked quietly, smirk taunting Derek. Stiles spit in his hand, reached back and wrapped his long fingers around Derek's cock. Derek's hips surged again, trying to find shelter in Stiles.
Stiles didn't move, though. He stroked Derek while brushing the head of Derek's cock against his entrance, teasing with how open and slick he was. Derek could feel his blood heating in his veins and a roar in his head and he was sure he was going to come before he could be in Stiles but the little shit was ready for him.
Stiles fingers sank to the base of Derek's cock and held firmly, staving off his orgasm. Derek almost whimpered but he swallowed the sound back, catching Stiles' eye and silently challenging him.
Stiles must have been goddamn psychic because he kept Derek on an edge that kept soaring higher and higher with every escalation. Every time he'd grip the base of Derek's cock Stiles would also pull a little tighter on the tie around Derek's neck.
He was never going to be able to wear a tie again without getting an immediate and raging hard-on, he knew it.
Finally his outer shell cracked and he begged Stiles, "Please let me fuck you, let me come. Please."
"Of course, Mr. Hale. Right away," Stiles whispered and sank down on Derek quickly, bottoming out on the first try.
Stiles grunted but was drowned out by Derek's outburst, "Jesus fucking Christ, Stiles, so fucking hot!"
Stiles snorted because it was incredibly rare that Derek ever lost control in that way. He quickly returned to the more important matter at hand and rose up again, letting Derek slide out of him until just the tip was trapped inside, then dropped again.
Derek was ready and grasped Stiles' around the hips as he thrusted up at the same time, drawing a strangled moan out of Stiles; finally he was taken off guard. Together Stiles and Derek worked up to a punishing rhythm. Derek was careful not to hold Stiles too closely or he'd cause bruises, or worse, but he was also worried about Stiles hurting himself.
"Don't you dare slow down!" Stiles gasped, reading Derek's mind again. Stiles pulled Derek's tie from around his neck and let it drop between them, wrapping it around his cock that he was stroking quickly. "I'm gonna come all over your tie," Stiles explained. "I've seen you wear this one a lot so I'm betting it's your favorite. I hope it is so you get it dry cleaned. When you send it out to be cleaned I hope your cleaners know that you'd never accept less than perfection with your clothes and they work so hard to get that stain out. I hope you can wear it again as often as you do now, at least every two weeks."
Stiles' voice came out hitched every time their sweaty bodies slapped together, in a rush and all at once. Derek heard every single word as Stiles continued on.
"I want you to remember this moment and how deep your cock sank into my ass and feel me squeeze around you to keep you in me longer," Stiles gasped out as he illustrated his words and Derek let out another string of curse words.
"I want you to put on this tie, because it's your favorite one. Do it without thinking anything else about it. And then some time during the day... maybe you're answering email, or at dinner with a client, or in a meeting with the other owners. I want you to l-look down at this tie and know exactly the pattern of my come all over the s-silk and the t-taste of it when you lick it off." Stiles final words came out as a breathy sigh while their rhythm stuttered and Derek felt Stiles flutter around him.
Derek looked down as Stiles came, watched him wrap the tie around his dick to stroke himself through his orgasm and make a mess of it and their bodies. Stiles kept moving on Derek, although their pace had slowed considerably. Stiles redoubled his efforts as he gathered up the tie.
He wrapped the tie around Derek's head loosely like a gag, making sure Derek got a taste of his come on the silk. When he was done he clenched around Derek's cock and held his chin to look in his eyes.
"Now fuck me and come in my ass!" Stiles demanded and reached out to flick Derek's nipple.
Derek felt dazed from Stiles overload. His senses were flooded with the taste and scent of Stiles and his come; from the desperate feeling he was causing Derek physically and mentally; with the erotic sounds of their bodies moving together and against each other; most overwhelmingly from the sight of Stiles moving in front of him, arching up and experiencing full-body vibrations.
Derek wanted to commit as much of this moment to memory but Stiles wasn't waiting for him. Stiles started moving his hips up and down on Derek's dick, clenching at the tip when he rose up so far that they almost disconnected. Then he'd alternate between sinking down slowly on his shaky legs or letting himself fall back. Every time Stiles did the latter they both let out rough grunts.
Derek ran his tongue over the tie in his mouth, tasting Stiles—inhaling Stiles— and fought back his desire to throw Stiles onto his stomach and really pound into him in a way Derek's not sure he's ever had the pleasure of even entertaining in his own head. He knew Stiles could take it and he'd like it.
But there was a suspicious swelling of Derek's cock so he kissed Stiles hard while he dropped his hips back as much as much as he could. He also maneuvered Stiles so he had control of the pace and could control Stiles' thrusts.
"Gonna cum," Derek murmured into Stiles' mouth.
"Yeah, yeah," Stiles grunted, the sounds pushed out in time with their movements. "Come in me, please."
Derek let go, whether it was it was by his own volition or if Stiles' plea broke his last tattered shred of self-control. He held himself at the base of his cock so he wouldn't be tempted to bury himself in Stiles fully, and started coming. Stiles clutched at him around his neck and whined into Derek's neck as his come made him even hotter. Stiles wrapped a hand around his own cock, trying valiantly to swing back to full hardness, and stroked himself off to a weak orgasm as Derek petered out.
He thrust a few more times slowly, still battling back his inner voice that wanted nothing more than to knot Stiles, then eased them apart by rolling them together to their sides and stretching out in Derek's mess of a bed. He unwound the tie from his head and licked his lips to get any leftover Stiles. He put the tie on his bed-side table awkwardly, Stiles' words about it being forever linked to this moment already ringing true.
Stiles slung his left leg over Derek's hip and ran his fingers through Derek's' sweaty, come-y chest hair and looked the perfect picture of relaxation. Derek felt like his brain was off-line and while he tried to sort himself out he stared down at Stiles, unable to come up with anything to say.
"Is there anything else you needed, Mr. Hale?" Stiles asked quietly, looking up at Stiles from under his lashes.
Derek's knot throbbed from unclaimed potential and shook his head. "Not right now, Mr. Stilinski. Do you have any other questions about my tie?"
Stiles grinned but declined. Derek exhaled and started to close his eyes to enjoy the afterglow.
Stiles trailed his fingers over the skin of his left pec. "But the pocket squares you wear, on the other hand..."
Derek's eyes were wide open.