Warning: Um, I guess this is NSFW even though there's no smut. You've been warned. I'm a virgin so sorry for any inaccurancies, I guess.
Dean
Dean's gentle. He likes to make sure that you don't get hurt in the process and that you get pleasure as well. But don't get it wrong. It's not always sweet sex. Most of the time it ends with you screaming his name.
Sam
Sam likes it rough. And so do you. There's lots of lust involved. You don't take it slow and there's alot of biting and hair pulling.
Castiel
You were surprised when you first has sex with Cas. After making sure that you really wanted it and were okay with it, he became dominant. He's top most of the times and really likes to be in control to make sure you get what you need.
Gabriel
Fun is the word that comes to find when you think of sex with Gabriel. There's lot of teasing, games, and toys involved. His sweet tooth influences what you wear, resulting in you wearing edible underwear at times.
Lucifer
With Lucifer, you're never sure what you're going to get. At times, he's sweet and soft with you. Next, he's rough. Then, he's top. Later, he's bottom. There's lot of diversity which makes the bedroom (when you do it in the bedroom) a very interesting experience.
Crowley
Crowley's the king in hell, but he gets so turned on when you take control. This ends in him being a sub. Which leads to BDSM.
Balthazar
Sex with Balthazar always has passion. He never has sex with you because he's angry or is trying to get his mind off something. Balthazar has sex with you because he loves you and wants you. His angel powers are sometimes added to the mix of things and end with both of you really happy.