I rode bareback as a kid all the time. Mostly because I had a fat, wide pony that was like sitting on a comfy couch. On cold winter days I used to ride him bareback on top of his blankets.
My current mare has sneakily pointy withers and a backbone that will go right up your butt. Maybe with the right bareback pad she’d be okay but just plain it’s awful even at the walk. I tried a few trot steps once and yeah…ow. A few weeks ago when it was miserably cold out, I decided to relive my youth and hop on her on top of her blankets and ride her around. Turns out that two blankets are still not enough padding to make trotting a good idea. I am far too old for that nonsense!