The Unlucky Prison Sissy
Mickey Flynn has a gambling problem, and he owes his bookie, Momma Johnson, big. Momma Johnson oversees the female annex of Fairfield Corrections, and Momma has her fingers in a lot of pies. Momma uses Mickey to keep her prisoners happy, and it turns out the prisoners like Mickey sissified, servile, and in chastity. Momma uses Mickey to satisfy her prisoners, no matter how much Mickey fights!