I haven't had anal in a while, I know it will hurt , so I am avoiding it but the longer I wait the worst it gets

Break in is gonna be uncomfortable at first, do remember to push out on it and it’ll go in better. If your luck is like mine has been the guy will have a wide cock and hurt even more than usual.

Relax and enjoy it

Once was enough for my wife in college. Never again.

Pretend this is your first time having anal and start from the beginning — fingers, small toys, lots of lube, the whole nine yards. Spend as much time as you need stretching yourself out until it's comfortable.

Or just skip it. "Yeah, that used to be nice, but I've moved on"

Practice with a toy and some lube. No, a little more lube. A little more… and a little bit more just to be safe.

Use plenty of lube and tell him to start slow you got this

start soft, and work it up to hard

Well I looked for this comment but nobody else went there so I will; keep avoiding it, for the rest of your life.

Practice? 🤷‍♂

Use a toy or a smaller guy?

Grit your teeth.

Asstroglide

Practice with butt plug and lotsa lube

Practice with a suction cup dildo