Picking a toy for booty training and strap use. Halp!

[Lockhart <3]

So I'm looking for medium toy for both anal training and strapon use. My goal is to get to the point where I can easily take most strapons for pickup play. I'm not trying to train myself up to size queen levels.

So I've been looking and I think I've narrowed it down to 2 choices: Winston's tail, or Ika (both in medium size and medium firmness)

I was originally thinking Ika. I have a thing for tentacles and I used to own a medium tako in custom 2-tone mottled pink (think the hanns signature colors). Unfortunately it was stolen. But I got to looking and I think Winston's tail is super cute and quirky, not to mention reminding me of Tohru from Mrs. Kobayashi's dragon maid.

I've been over the details several times and looked over the dimensions and I really just can't decide.

Has anyone had a chance to compare these 2 for buttstuffs?

Also, how do they handle being used in strapons? Ika looks like a nice round base, but I'm afraid the bevel might make it not stay in the harness. Winston's shape makes me wonder if it will fit a round ring at all.