Dean Winchester has control issues, because he has trust issues:
Dean, who won't let anyone drive Baby, much less with him riding shotgun. (Exception: Sam-- Trusting Sam is almost completely involuntary. Dean just does it, like running his hands through his hair, fiddling with his watch/rings when he's anxious, or breathing.) In trusting Sam, Dean is willing to give up his control, because he knows that Sam will treat the Impala like an extension of Dean himself, and is therefore unlikely to wreck her.
Dean, who, in the beginning, wouldn't let Cas zap him anywhere. Despite the fact that it would seriously decrease travel inconvenience, Dean would rather drive.
Dean, whose musical rules apply to even Sammy. "Driver picks the music, shotgun shuts his cake hole" basically boils down to "I don't want to give up control of the radio because I don't trust your taste in music".
Dean, who, even when he was literally dying of heart failure, refused to let Sam so much as help him out of the car. (You can argue this one is a fear of showing vulnerability, but I would argue that fear of showing vulnerability is rooted in the inability to trust that no one will laugh at and/or think less of you.)
Dean, who, when all of Heaven and Hell were telling him he had no choice but to say yes to Michael, stabbed Zak in his face and went on to help save the world without ever being Michael's meatsuit.
There is one time Dean craves giving up control, literally aches for it, and that's during sex. Sure, he's a switch, but when he goes for submissive it's because he needs it.
He needs the peace that giving up control allows him.
Dean has spent his entire life having to make split second, life or death decisions, and giving that power to someone else is an almost holy experience. He doesn't have to think, doesn't have to decide anything; he just gets to lay back and let someone else drive.
And it's easy to trust someone with his body, his pleasure, because those are simple things. There's nobody's life hanging in the balance over whether Dean tops or not. No one will die if Dean allows you to pin him down in the Imapala's backseat and ride him into the sunset. The world won't end if Dean lets you dress him in your panties and screw his brains out, or throw him down on a mattress and rim him 'til he cries.
Dean doesn't always want to bow to someone's will, but when he does, it's because he needs to.