Picking Daisies

Bobby Gerry was a child of privilege. His family had money that started with railroads and horses back in the late 19th century and was grown by subsequent generations until the family fortune was now so large that it became meaningless, especially to Bobby. He was never denied anything in his life and combining that with some liberal ideas of parenting by his mother, which included letting the child find their own path to maturity, Bobby was spoiled to the point of obscenity. As such, his social skills were atrocious. But then he met his match. And her name was Mistress Lillith.

Lilith negotiated to get total control over Bobby's life and then the changes all began and a sissy baby began to appear.

From the great writing of Christine Kringle in the compendium: Bedtime Stories for Sissy babies (vol 3)