For a guy who is used to prostate self-stimulation (with fingers), how different is prostate massage from an experienced domme?

It's roughly the same as the difference between masturbating and having someone else do it.

Same (or similar) physical sensations.  Completely different mentally.

better to have someone else Do it . good Vibrators ECT. Lori in boca

How well can you cut your own hair compared to having a hairstylist do it?

you've come to find that deep down, you know the answer.

When you're with a experienced partner angles are more accessible and the possibility for multiple non ejaculatory orgasms is high. It all depends on who you're playing with though, of course.

Self pleasuring, or a sexy companion to do all the naughty bits?

I love to play solo, but it tends to get boring & that is why I have returned to TER! lol Smile 4 me!