So you want to take a fist?
Fisting is an Olympic-level sexual activity that takes serious training over time and is best done on your own with BIG toys, allowing you to control the stretch and train more often. This means you’re very unlikely to take a fist the first time you try.

A large cock or dildo is maybe 2” in diameter, 6” circumference. You need to be able to take a toy about 3” diam, 9+“ circ, to be able to take a fist. My fist is about 10” circ and I have a medium-sized fist. It’s very rare someone who hasn’t taken a fist before can take mine.
Use toys and LOTS of lube. Avoid numbing creams. Learn the difference between a good stretch and going too far. A sharp pain means stop! Poppers can help relax your hole. Makers of high quality platinum silicone toys like ToppedToys.com and FriendlyToys.com make many series of dildos and buttplugs in sizes from beginner to pro, each just a little bigger than the last. This is how you slowly, safely train your hole to take bigger and bigger toys and work your way up to a fist.
Taking a man’s fist is one of the most intense, most intimate, most satisfying, most mind blowing sexual experiences you can have, often leading to anal orgasms that radiate through your entire body and can be repeated over and over one after another without a refractory period. Forget your cock and focus on your hole. Chastity goes well with fisting. Train like an athlete and you’ll probably get there in a few months or so. It’s absolutely worth putting in the work!