Yes-Yes-Yes. A million times yes!

Especially if you are planning on "changing the holes," so to speak. Vagina and anal flora do not go along well, and you don't want any of the rear end bacteria there.

The same goes for sharing an anal toy with another person - you'd better not, but if you want, slip a condom on it, and then slip a new one before passing it on to your partner.

If you are just playing by yourself and do not plan on changing the orifice, the usage of condom depends on the type of the toy.

Typically, glass or metal toys are fine to go without condoms, just with a quick rinse before and thorough cleaning after. Silicone toys are more prone to getting dirty, but there is a trick since silicone toys do not go well with the lubricant that condoms are covered with. If you want to use a condom with a silicone toy, look for condoms with water-based lubes. Sex toys that absolutely need a condom are toys from porous materials, like TPR or Jelly - they can gather everything you don't want them to, and it won't be easy to clean.

Hope this helps