I got the LELO Ella and the Climax Silicone EZ Bend Slick Shaft as my first toys.
Before that I had only tried some cheap fur-lined steel cuffs that were NOT comfy. I used them, like, twice with my ex. Now I have some nice comfy leather ones
The Silk Small. It was a fantastic first toy, and if I ever have to introduce a guy to anal play, it will probably be what I will use. Even the most resolute top wouldn't be scared off by my little Silky.