dean getting hired as cas’ secretary, through some miracle interview (and maybe some fake references, but who’s checking?) and the first few weeks dean is intimidated by the guy. cas is always wearing a suit, always working - although technology seems to be his personal enemy - and always grumbling about his coworkers. dean learns quickly that cas takes his coffee black, likes his desk in immaculate order, and that he doesn’t really know what cas’ job actually is. dean assumes it’s a given position though, since sam fills him in one night over dinner that the company is owned and run by cas’ relatives. so one day, maybe a month and a half after being hired, when cas calls dean into his office and asks for coffee, dean tells him he should try a mocha instead and that gets cas’ eyes on him, startling dean with the blue of them. cas just nods and turns his eyes back to his computer. dean stumbles out of the office, giddy with the success of cas not yelling at him. 

so over the next week he tries his luck, makes little suggestions to cas while handing him reports or papers or messages, tells him he should wear the blue tie with his suit instead of a green one (cas always wears a blue one after that), he should try not yelling at the girl who delivers the mail, little things that he thinks of at a moment’s notice. cas does every one with a nod and sometimes a hint of a smile, eyes sparkling in a way that should not be making dean half-hard every time cas listens and follows the words to the letter. 

dean’s been at the office for three months now, cas has a huge deadline and dean is working overtime (it’s ten pm and he’s the only one in the building) because he wants everything to go right for cas, has this weird desperate want to do an amazing job for cas that he doesn’t fully understand but listens to anyways. when the last paper is printed and filed dean shuts down his computer, mentally going through the places that will be cheap and easy dinner to pick up on his drive home when he sees the lights on in cas’ office. frowning, dean makes his way over and sure enough, cas is sitting at his desk, hair even more crazy than usual, trenchcoat and suit jacket flung on the side of the desk, the white sleeves of his button-down rolled up to his elbows. quietly dean slips inside, locks the door behind him. cas doesn’t notice, doesn’t look away from his computer until dean drops his bag next to cas’ desk, taps him on the shoulder. there’s a crazed look in cas’ eyes when he meets dean’s, something that tells him that what he’s about to do won’t be too much. dean thinks briefly of all the times he told cas to do things over the past months, how well it’s been received, uses that to build up his courage when he tells cas to turn off his computer (cas does immediately), voice feeling rougher when he all but orders cas to stand up and take off his shirt and pants (cas’ cheeks flush but he does so with no hesitation), feels his mouth water at the sight of cas’ hard dick through boxer briefs. lowers himself into cas’ chair, feeling drunk and giddy and scared with this power cas is giving him, asks him to take off his underwear, tells cas to touch himself.