WELL, when i was six i had a stuffed bear big as me with a hard plastic velvet dust(?) coated nose. Ive gone through so many hair brushes.. And those jelly water filled slidey cylinder things from party stores (someone pleae remember what im talking about) First ever proper dildo was a rubber fleshy, vibrating stacked double penetrator. Peanut butter and a chihuahua will do in a pinch..
Ejaculated onto a lot of magazine and catalog pictures when I was younger, and on-line porn wasn't so available. Playboy, Penthouse, Hustler, Lingerie catalogs - all had some pages glued together. Masturbated into soft white socks when I didn't have anything else to catch it in and didn't want to mess up my underwear. Into/onto bras and nylon stockings (see some of my other content entries).
There's so many things I've came on and in over the years. Cum in nylons in high on my list along with my girlfriend's sisters pants.
Most of the time I just use rags or TP to make sure I don't make a mess. I have used shirts with celebrities on them as skeet blankets as well. Also magazines, and once a calendar.