Just as an update; This comment as well as everyone elses has been INCREDIBLY helpful. I still don't particularly like pegging, but I no longer dread it in the way I used to, and it doesn't feel as out-of-place to me anymore. I have evenbfound myself enjoying it a little at times. The blindfolding, as well as the discussion around roles and how the expectation that I will be "taking control" makes me uncomfortable really changed the game. We did end up investing in a pillow, and while it hasn't done a ton for me as I am still struggling a bit with height, it has done WONDERS for him. Thank you all, genuinely, so much for your help and advice.