What is the first thing you put up your bum?

[Crios]

Was in Vegas for COMDEX (kind of the precursor of ces). One afternoon during a lull in the programs, I walked a couple blocks west of The Strip to an adult bookstore. Once there I bought a porn mag and a 6inch pink dildo.
Walked back to my hotel (the old Desert Inn). Lubed up the fake dick with the lotion from the bathroom after first using the suction cup of the dick to attach it to the low makeup table. Stripped and lowered my hole to dildo and slowly dropped down. Was shocked at how quickly I opened up to take it to the hilt. Took just minutes to come.
My insides were all gushy the rest of the evening. Had to go to a reception at the hotel that evening. Felt deliciously naughty all night.

 

[BerryTangerine]

60's man here thinking of trying some anal play alone and with my wife, but other than fingers I'm not sure what to try. Jumping straight to a life-size dildo seems to much to start with, so was hoping to get some ideas of alternatives.

What did you start with and how do you progress to something bigger?

I put a toothbrush inside myself when I was like 13. The handle side. Hope that was obvious.