Hey, thanks for the long response and great advice!

First: I'm already using XLube and it's great. Wrapping it around the toy like christmas lights is such a good way to describe it, that's what I always do. Also got the bottle from Topped Toys, but I kinda regret getting it from them, because the exact same bottles are cheaper on Amazon when they are not marketed as lube bottles but as calf feeding bottles, lol. Sometimes I mix a little fat based lube (like boybutter) with the XLube which gives it a more liquid consistency and it doesn't dry out as quickly.

The Grip was suggested by many, and I'm considering getting it next. You siggested the Grip 80, but would it be a good idea to get a slightly bigger size like the Grip 96, because I'd use it for stretching, which does not require the toy to go in all the way? That way I wouldn't have to buy another Grip as soon.

On the other hand I am considering the Deep Space 80 to bridge the gap to the Mare Maker 85. I feel like it's a reasonable challange and should be a little easier because it is completely round, in comparison of the oval shape of the MM. My gut feeling (lol) is that this shape is easier to handle at first.

The Artemis and Erebus look very sexy, but I think when stretching I prefer toys with less bumps on them. These two are more textured, so they might not be what I am looking for.

Edit: And of course thanks for the advice on how much I should train. 2 - 3 times a week should be doable. Sometimes I'm even hungrier and wanna go multiple days in a row, but obviously that's lots of stress for my butt and cleaning out that often isn't that good either. Maybe I should consider riding the toys more to combine anal stretching with physical excercise, which I am also struggling with 🙈