Definitely use butt plugs for training. Our boy pussies have a tendency to tighten up when we don't use them enough, and that can get painful if your lover is in a hurry.
I use one that is around 6" in circumference. After some practice, it fits fine now, and it's plenty. Hard dicks are still somewhat soft as squeezing is concerned.
As you get used to it, you should be able to use it in the shower before the "big date" to make sure you are sized properly, and you'll be good to go. I make sure it goes in and out past the widest part easily, and I let my sphincter rest on the widest part for a few minutes.
Also silicon lube is the best.
For pre-date clean out, I use an enema bag with the long women's nozzel and gently scrape round and round forcing the water out into the toilet so as to not have it go too high in side me and leave some liquid stranded that may come out accidentally and ruin the experience.
Then get an eye dropper or syringe and put in about 1/4 teaspoon of lube in your pussy. It's a bad idea to leave it all up to your partner. Once he's going for it, you cannot create your own lube. So lube your boy pussy yourself.
