Does Dean look different to you in this photo? The hunter gets turned into a vampire on the episode "Live Free or Twi-Hard."
Dean gets into a bit of trouble on the episode "Live Free or Twi-Hard." How so? He gets turned into a vampire.
Things get a little dicey on the episode "Live Free or Twi-hard." Vampires get involved with the brothers.

Supernatural Season 6 Episode 5 Quotes

Dean: Try uh, Lautner.
Sam: He's a werewolf. How do you even know who that is?
Dean: What are you kidding me? That kid is everywhere. It's a friggen nightmare.

Look at this. Watching her sleep, how is that not rape-y?