I've been to WDW seven times starting when I was 4 (I'm now 29):
1986 (4 y/o), 1990 (8 y/o), 1994 (12 y/o), 1996 (16 y/o -- ugh that awful birthday cake castle!). All these trips were with my parents and little sister.
Feb. 2009 (27 y/o) -- Offsite trip with DBF (27, his first trip to WDW).
Oct. 2010 (28 y/o) -- Offsite trip with DBF (28)
Oct. 2011 (29 y/o) -- Contemporary Resort with DBF (29)
And we have two more trips coming up:
March 2012 -- Windsor Hills with DBF, his mom, sister, brother-in-law and nephew.
Oct. 2012 -- Animal Kingdom Villas-Jambo with DBF.