This one is a favourite of mine

A Good Man (http://www.fanfiction.net/s/6238132/1/A_Good_Man)
Sappy one shots from Lisa Braeden's mother's POV of Dean and his impact on Lisa and Ben.

You might like these too?
Role Model (http://www.fanfiction.net/s/6882085/1/bRole_b_bModel_b)
The James Dean Job (http://www.fanfiction.net/s/6529422/1/The_James_Dean_Job)

xxx

If you don't mind self-recs, I have 3 stories that are set during Dean's year with Lisa and Ben:

It's Enough: http://www.fanfiction.net/s/7644393/1/It-s-Enough

Broken: http://www.fanfiction.net/s/7752460/1/Broken

Fragments of Sorrow: http://www.fanfiction.net/s/8507327/1/Fragments-of-Sorrow

This is an AU take on Dean with his life with Lisa and Ben after Sam jumped into the pit...and what happened when Sam came back. Written after "Swan Song" and definitely Gambled once season six started.

Legacy (http://archiveofourown.org/works/1039785)

By staceycj:

- Introductions . Angst. Summary: Dean introduces Lisa to the only other Winchester left.
http://www.fanfiction.net/s/6302325/1/Introductions
- First Christmas . Angst. Summary: Dean's first Christmas with Lisa and Ben.
http://www.fanfiction.net/s/6209768/1/First-Christmas

By FaithDaria:

- Sour Cherry Pie Life . Criminal Minds crossover. AU. Summary: Dean has retired to the civilian life. Too bad no one told the serial killer currently stalking teenagers in Indiana.
http://www.fanfiction.net/s/7050961/1/Sour-Cherry-Pie-Life

Going Through The Motions (http://archiveofourown.org/works/788624)

This one's pretty angsty. Basically Dean wonders what the hell he's doing trying to live the apple pie life.