His hooves may be a bit tender at first while the blood flows through, (sort of like when we get pins and needles after sitting awkwardly till the blood gets through again.
That will comes right fairly quickly - if you are talking tender to ride - yes he will be and that can take a couple of months as the hooves harden. You can get him hoof boots (Ezy Boots or similar) so that you can ride if you need to while this heals.
Still much better than having the shoes on. What happens with shoes is that the shoes stop the hooves ability to expand - a metal bar has no give.
Do please make sure that you get a proper barefoot trimmer - not just a farrier who trims as if he is going to fit a set of shoes Totally different trim needed to go barefoot
This is a great site about barefoot...
Iron Free Hoof