for #2 I can give you an idea, one that I discovered on my own, but found other forums where guys have posted they also had this idea....and it works for them as well.
Vac-u-loc strap-on dicks have a suction hole molded into the back to lock in place on the harness, this hole is about the size of your middle finger.
I got one to experiment with, i tossed the harness away, and grabbed my exact o knife.
I trimmed away and blended the opening until it would get a seal around my small member.
With lube to help with comfort, I now have a hard dick to jack off with, and damn it feels so right!
I also purchased a heavy duty harness that would help with support during intercourse when i play with someone else.
I safety caution is also warranted here: the suction is real, and your member can get hurt, so please play with care and attention.
I say it now guys, there is a full blown market here for designers and makers of toys, if they would only think like a FTM and get us products that`s made for us, not recycled ideas from their other lines for different peoples.