"Route 666" has the honour of being the first episode that includes a sex scene featuring one of the brothers. Apparently this was in response to network pressure to include more romance in the show. They were picky about how said romance should be depicted though.
The demand of the network to have more romance on the show produced a
strange kind of moral to be adhered to. Anthony Pinker, one of the editors, explains:
"The violence we don't get a lot of notes on." For the episode "Route 666" though,
"... The note I got from the network was 'The girl can't be on top.'"(cit.
S1Com, p. 77)
http://www.supernaturalwiki.com/1.13_Route_666#Minutiae Despite this insistent directive, the aired episode does show Cassie on top for a fair bit of the scene:
One can only assume Dean spent even more time on the bottom before the network demanded an edit, so show must have been pretty keen to depict him that way. Indeed, in the earlier seasons, Dean typically wound up on the bottom at some point during his sexual encounters:
S4 "Heaven and Hell"
S7 "Slice Girls"
It's almost like they were trying to make some point about him, or something 😜
Btw, the Dean/Cassie scene in "Route 666" originally aired with Bad Company's "She Brings Me Love" as the backing track. It was one of season one's great musical moments, imo. Unfortunately it was replaced by Sharif's "Paradise" for streaming purposes, which I feel is a pity as it seems to me to be completely out of tone with the scene.
.