Derek Hales Casual Sexcapades or
the five times derek tries having a casual hookup and everything goes horribly wrong and the one time it doesnt (but except it kind of does)
[this isn't really fic but uhh dubcon warning regardless]
Wherein Derek was never a casual sex kind of guy but he figures his life is a little too messed up to really try dating anyone but he’s also getting tired of his solo a mano sex life so he heads to the nearest big city for a weekend to try to find someone to spend it with and everything is going great until he realizes post sex that he’s this person’s first and theyre totally chill about it you know - virginity is a social construct, after all - but derek just doesnt see it that way and he tries to keep in touch with them, asking for their number and they get really put off by him and leave and derek just is not happy about it.
And then its a few months later and derek decides to give it another shot so he finds someone older this time - has a couple drinks with an exec from some big company back east - and they head back to his hotel room but the morning after they start talking and the exec casually mentions their family and derek is just awash with guilt and he cant believe someone would do that to their spouse/that he HELPED someone do that to their spouse and he kicks them out and is just FURIOUS.
The third time derek tries casual sex is totally unplanned. He’s just roaming around town keeping an eye out for shady goings on but he finds himself outside of Jungle and he decides he might as well. So he’s had a couple of drinks (not that they do much for him) and he’s danced a couple of songs and hes been eyeing one guy in particular. So they do the whole ‘watching each other from across the dance floor’ thing, steadily getting closer as the song goes on and they end up outside in the side alley. Its quick and messy and afterwards derek feels dirty and unsatisfied. He decides that its the last time and for a long time it is.
The fourth time derek decides to have a casual hookup its with DANNY of all people. Its spring and the pack is mostly away for college, but dannys back because he has two weeks off for spring break and he’s going to spend one week at home and one week in puerto vallarta. By now dannys been filled in on everything, hes officially pack, and - just like the rest of the pack - the majority of his free time in beacon hills is spent at dereks house. They talk and danny sets up dereks new router and then as theyre sitting on the couch watching netflix danny asks if derek wants to have sex. Derek agrees because danny is handsome and fit and good natured and he wants to have a positive sex experience for once dammit.
Everything is going great - they both agreed that it was a one week only kind of deal and the week is nearly coming to a close and derek isnt feeling remorseful. He likes danny - i mean, who doesnt like danny - but he’s not feeling too attached. Everything is going perfectly until the last night before danny leaves where right as dannys about to come he moans out “miguel” and that just puts a damper on everything. Dannys super embarrrassed and tbh so is derek, but he says he understands and theres no hard feelings. They decide it will probably be best if they NEVER SPEAK OF THIS AGAIN so they dont.
The fifth time it happens is not too long after the whole thing with danny. it's nearly summer and dereks out and about in san francisco picking up some stuff for the summer. he's excited because everyone is coming back (coming home) and he's buying lots of useless junk that the pack will love when he catches someone watching him, giving him the look. derek's in such a good mood that he doesn't immediately disregard them the way he usually would and after he spots them at a couple more shops he decides why not? they find a cheap motel and do their thing but then derek catches a whiff of something not quite human from his partner. turns out derek just banged a succubus/incubus. he escapes back to beacon hills and eventually defeats them with the help of the pack.
"derek sucks at having casual sex" stiles says repeatedly for a week. derek corners him one night and offers to prove him wrong and stiles grins, willing to take that bet. "win/win" he mutters under his breath.
and then basically this happens, and at the end of the day stiles gets to keep on saying that derek sucks at having casual sex.
