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I would start with something like this beaded toy because it starts very small and gradually gets larger. (Butt plugs are used to keep an already open hole, to stay open.) Go slow and use plenty of lubricant. While silicone lube feels the best, it dissolves silicone toys and leaves stains everywhere. So I would go for a water-based lube like Gun oil. There are better ones, but I'm trying to keep it reasonably cheap for you to start. Once you feel comfortable with your toy, you can try a vibrator.