Dean/Jess stories are much rarer than Sam/Jess for several likely reasons:
- Sam/Jess is canon
- Jess dies at the end of the pilot, having met Dean (canonically) one time, apparently only for a few minutes.
Since when have minor little details like that stopped fic writers, though?
The most frequent scenarios for Dean/Jess fiction include:
- Stanford-era fics, in which Jess and Dean meet on one of his trips to check up on his brother, usually before the start of Sam and Jess's relationship
- ghost!Jess fics, in which Dean somehow becomes sensitive to Jess's presence after her death
- AU fics; for example, fics in which Jess doesn't die