How Long Did It Take From When Pegging Was First Brought Up To When You Actually Did It?

Too long!

he's indifferent well reluctant about it

Naive one here, Never

I recall that I told my wife that I wanted to try it and talked her into giving it a go. I found a harness from Aslan that was simple and not too expensive (no buckles for her to be intimidated by, easy to adjust). Once it arrived, along with several other toys, it sat unused for several months. For whatever reason neither of us found the right time to try it. Then, we went on a vacation and I packed it up with the rest of our toys. She surprised me one rainy afternoon by coming out of the bathroom wearing a sexy black negligee, the harness with a red and black Mistress dildo protruding and a huge smile. The rest is history as they say.

After a few drinks, and some interesting foreplay....discovered some of my toys could now be called our toys. Reverse role play came a few weeks after that.