Help finding soft dildos for anal sex and good…

I usually go for a vibrator because I think the vibrations will get me off quicker, but I’m too tight for anything that rough, so I need a soft dildo that I can train myself with. Any recommendations? It would be even better if they came in sets so the looser I get the higher my level. As for butt plugs, they confuse me to be honest. I thought the purpose was to enlarge the hole, but looking at the designs of most of them, the part that touches the hole doesn’t seem to stretch very well. I know it can’t be the same size everywhere because then it wouldn’t stay in, but how do they help you stretch/train your hole?

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