I have tried this a few times with no success with my finger, not had a really long go with my finger but didn't feel much and wondering if the toys made a big diference as they are shaped to get to he right places? Never orgasmed via prostate milking but hear it great?
I find it's best to put your hand between your legs and after insertion do a come hither motion with your finger. If you're in far enough you should be able to a feel small blob for want of a better word. Never tried toys so can't give a comparison.
I can't hit my own prostate with my finger and I have a good sized hand on me. Have a screwdriver handle that works just right. Can't cum that way but it's a great enhancer for Jerking Off and climaxing. Love fingering an other guy and feeling his prostate getting harder and harder as his organism gets closer to the end. When it's rock hard, he's shooting his load. Sweet !