Sasha Honestly the biggest harm I see on the dating side are the inequality and the risk that this will promote relationships where partners have no trust in each other. If those factors are mitigated, that could be a viable future.
Penal chastity is probably best left to the realm of fantasy though. With a corrections officer holding the keys, chastity devices sure would fall into cruel and unusual territory quite quickly for many prisoners, and as much fun as that can be when the prisoner is fictional, I do not really buy into the whole "criminal scum deserves no better" stuff.