Two stories:
In Paradise Island, Michael, a young man facing unemployment, meets a mysterious woman on his last day at the restaurant where he has been working. She offers him a job at her exclusive sexual retreat. She has plans for him far beyond his imagination.
In A Position in The Family, Phillip, a young man raised by a single mother in feminine pursuits, including occasional crossdressing, is offered a job tutoring his cousin at the remote but luxurious estate of his Aunt's. Miss Terry, his cousin, is a dominating person and soon has him in dresses and lingerie and virtually serving as her maid.