The Unlucky Prison Sissy (A Forced Feminization, Chastity, Spanking, Sissy Training, Forced Prostitution Tale)

Mickey Flynn has a gambling problem, and he owes his bookie, Momma Johnson, big money. Momma Johnson oversees the female annex of Fairfield Correction Facility, and Momma has her fingers in a lot of pies. Momma decides to use 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 it!

Over 37,000 words