What is your experience with stretching toys?

My anal libido has reawakened with a vengeance! I've had lots of experience with insertion toys, now curious about stretching toys. For example, I'm looking at the Dino toy, from Square Peg. https://www.squarepegtoys.com/product/dino/

My questions are these: how is your experience with stretching toys? Do you use them frequently or only sometimes? Are they among your favorite toys?

Also, What material do you prefer and why? Up to now I've chosen firm silicone. Is there a benefit to a softer toy, in general, and specifically a stretching toy?

One other uncertainty I have is whether I'll run out of length to accommodate such a toy before I reach my maximum anal dilation. Decisions, decisions!!

When it comes to Anal stretching the best toys in my opinion would be the classic cone shaped Buttplugs, they're perfect for slowly advancing in Diameter until you master them and get them completely inside. The Dino toy you shared is also a good Idea but if you wanna reach your maximum diameter you should keep your eyes on short toys which rapidly increase in girth, since it can be very difficult to master a very long and thick toy, your second ring would be at its limits but your first isn't even close if you have already some experience in stretching. I personally prefer my toys a little firm, made from PVC (also way cheaper than silicone, which can be nice if you plan to size up in the near future and you already know the current toys are not gonna be needed anymore) but that makes the stretching a little harder, since you can't just sit on the toy and let gravity do its thing until it slips inside, you have to slowly let yourself sink onto it and at a certain point pull yourself down on a stool or something similar which can cause a sore Tailbone if you're rushing it a little to much. But the rewarding feeling of a fat, firm Plug popping into place is something I never want to miss in my life.