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There have always been a few fics around that eroticise a more weighty Jensen or Dean, in a similar vein to those that find an ageing Dean, Sam, Jared or Jensen a turn on.

In 2007, partly inspired by news that Supernatural staff were reading LiveJournal, a short piece of crack by memphis86 mentioned the attraction of Jensen carrying a few extra pounds. A number of posters revealed their attraction for pudgy!Jensen or Dean. Katjad wrote a Future Fic Alligator Alley (Sam/Dean, PG-13), which featured a thrity-five year old Dean who had gained some weight, much to Sam's approval.

From there the community JubJubFest (now deleted) was spawned which stated it’s mission as:

It's... hard to explain. A while ago there was this post which kind of caused an EXPLOSION of Chubby!Jensen love and even some Chubby!Dean thrown in for good measure. This post followed and it became clear to me what had to happen. November has been dedicated in loving support of Jensen Ackles and his tendency to be a little soft around the edges. And thefact that we LOVE him for it.

People posted fic to the community, and also photos which caught Jensen (or Dean) with a double chin, or a rounded belly.

There was a negative backlash to the posters, with some fans feeling this was disrespectful of Jensen, and a heated exchange occurred across fandom.

In the 2009 Big Bang challenge, a story by mediaville Lost and Found, was an AU story of an overweight Jensen who joins an obesity research program and falls for his trainer - Jared Padalecki. It was alternately lauded as an insightful look at the complex issues of self-image and self esteem, and condemned as a narrative implying happiness was linked to losing weight.