Although I have never considered sexual interaction with another male, I have fucked my ass with a (big) wooden dildo, and know that the prostate massage (with a little help sometimes) will cause me to ejaculate.
A gay guy named Fred bought a house next door to where my wife and I have lived for several years, and he really is "pretty" but also masculine.
I suspect he would be up for interactions because he has flirted with me on occasion, but never any overt suggestion.
I came up with a device I thought would allow me to "ease into" gay sex without really having gay sex. I took an old pair of shorts, and cut open part of the bottom, starting just in front of my asshole. I stitched together a "sheath" about 18" long, and big enough around to easily allow my wooden dildo (2.5") and had a sort of "vulva" area- the fabric was felted waterproof.
I stitched this so that the vulva area showed between my legs, and the sheath would pass between my testicles and up along the shaft of my penis (inside the shorts). I lubed the whole thing up with KY jelly, bent over and slid my wooden dildo into it. It seemed to work great, and I added some strings to hold it in place, especially so my cock would get rubbed instead of moving away.
After removing the dildo, I put rubber bands around the sheath, all the way down to the vulva area, and (wearing these shorts) went over to neighbor Fred's house.
I knocked on the door and nobody answered, but the door was open slightly so I went on in. Fred is a sort of strange guy, and had always claimed to have found an alien lifeform in the desert and that he took it in as a pet and fed it algae. I probably should have been more interested, but I had actually refused Fred's offer to SEE this alien life form, which Fred said was unlike anything on Earth and had 6 short legs that also worked as arms.