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i love riding bareback (on certain horses) when i used to lease, i'd bareback every chance i got, b/c the horse had a really comfy stride and being a warmblood he had a very comfy back :)
I like riding with a saddle better. My horse is a little bit difficult to ride bareback, she's too responsive and her quick turns are hard to sit for my liking.
Depends how I feel that day. I ride both, but its better to rise with saddle unless you know your horse is 100% bomb proof. If not just be on guard and ready for surprises.