Henry was always happier when he was dressed up and living his life as Sophie. For years he’d wondered how he could live as a woman full-time but it was always one step too far.
Then one night he bumped into a transvestite called Megan at a club who had made her kink, her living. Taking Sophie under her wing, she instinctively knew that deep down, a sissy prostitute was eager to break the shackles of a drab male life.
Megan had to be sure that Sophie was ready for such a drastic lifestyle change. So she decided to setup an extreme first night for Sophie to ensure her new partner could handle it. This story is all about her first night working and became her Initiation to the Game…
This 5,200 word story covers crossdressing, sissy and prostitution themes and is intended for adult audiences only.