If you can get viable female flowers to be produced on an originally male plant (A.K.A. a reverse hermaphrodite) and continue to selectively do that to any male offspring; then sure. Within the first few generation you should get some males that pass on their male chromosomes and form a YY male seed. I can't see any reasonable way of making that happen though. Plus, it could also turn out to be some sort of mutant plant; as all males should have both an X and Y chromosome. If it did grow and produce pollen, it could never produce a female seed; as it would always pass along it's Y chromosome. The best you could hope for was another male hermaphrodite.