If you’ve had something up your arse before, you will know what pleasure and what pain can be derived from dildo training. It is a combination of both. But what I can guarantee is that you will always want more. You will want bigger and better things in there.
Deriving pleasure from your arse is such a turn on because you don’t even need a hard on, just a good Mistress who knows what’s she’s doing with a dildo or strap-on. Starting you off with fingers, then moving onto butt plugs, dildos, then hopefully a good fisting.
My first guy who wanted some dildo training was very submissive, he would let me do anything to him, and within a month I was having him double dildo-ed. He was able to take two at once, such a horny sight, especially as I had it on video. He would call me throughout the week and we would have phone sex him sat on a nice big dildo with a sucker on the end pulling his cock, and me instructing him if and when he could cum. Is this the sort of thing that would appeal to you?