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Softer toys are going to be easier to take than stiff toys. Siff toys sometimes feel better to me but will leave you way more beat up and way more soreness the next day. Every anal enthusiast needs a few different sized butt plugs. I plug before i play. This helps get u loosened up enough for easier entry. Big toys are very expensive and one of the ones i started with is the Jet Annihilator Dildo. E bay is the best site to find that one for around 60$. My nicer big toys are all in the hundreds of dollars range, Mr Hankeys and Nothosaur toys. If you want to get something really big go with a softer or regular firmness. If u go really big and supper stiff u will hurt yourself. Be careful, take it slow and listen to your body. J lube is a decent lube to use and can be mixed to different thicknesses its also decently priced. Also coconut oil and olive oil is very health for your anus. And as always do your own research on everything when it comes to health and your body.