the problem is if they rape his ass in general population, he will love it.
Depends on what they use.
Unlikely ... creeps like this tend to be pitchers, not catchers. The problem with letting "Bubba" bugger him as a punishment is that "Bubba" is then being rewarded for HIS crimes. Prison should be a punishment, not a playground for violent perverts.
Give him a sledgehammer and a big pile of rocks. Tell him that he gets a special prize when he wears out the sledgehammer. (Special prize being a brand NEW sledgehammer ...)
or they just might find something it’s guaranteed not to like...
I was thinking of something much more drastic. Something he most definitely would not enjoy. Something that would make the kids around him safe if he ever got out.