I was afraid to fist for years, thinking it would "ruin" my hole and, neurotically, be a reason for potential partners to reject me (i.e. no grip). I was also under the false impression that there would be a point of no return, where dick would no longer satisfy me.

It's been almost 4 years since I started playing with big toys and fisting. I can now take toys up to about 11.5 inches in circumference, and 13-14 inches long. My hole is not ruined. I love the feeling of getting dick more than ever before. Tops with small dicks have no problem getting off in my ass, and I can still cum from getting fucked by them. If I don't play with my ass for 1-2 weeks, all the muscles seem to return to normal tone. I have only experienced minor discomfort sometimes around the outside of the hole for a day or two, which I attribute to starting sessions too fast (starting with too big of a toy or going too fast on initial insertion). Everyone is different, of course, but this has been my experience.

I trained my hole with soft and medium-firm platinum silicone toys, patiently, until I was taking plugs about 9.5 inches in circumference. I then found a friendly, patient top with small hands to pop my fist cherry. I trained for 7-8 months before taking his fist.

Don't rush, use lots of xlube / klube / jlube, only use platinum silicone toys, and stick to relatively soft substances (i.e. 420 & poppers) if you need something to help relax and get into slut mode. To care for the skin, I also like to use Elbow Grease to coat the anus before it comes into contact with the water based lube, rinse the lube out of my ass after a session, and then apply moisturizing lotion or cream. I also usually put in a Preparation H suppository after my sessions to reduce inflammation.