Best Way to Get Comfortable with Bigger Sizes?

Anal play is amazing, but rushing into bigger sizes too fast is a guaranteed way to make things uncomfortable (or worse, painful). I found that warming up with a small plug for at least 15-20 minutes before moving up makes a huge difference, letting everything relax naturally instead of forcing it. Plus, using a thick, long-lasting lube like silicone-based makes everything so much smoother. What’s been the best trick that helped you get more comfortable with stretching?