Billionaire's Sissy Maid

“How can I be of service, Mistress?” I asked my master as my nerves starting shaking from the strange way everyone was looking at me.
Sandra grinned at me. “It’s not me who you will be servicing, maid. It’s our guests.”

After truly accepting his new role as sissy maid for Sandra Owens, one of the world’s wealthiest women, Derek begins experiencing new desires and urges. Lucky for him, his mistress has new sissy training prepared for him. She has plans for him to both learn how to feel and look more like a woman.

What Derek doesn’t realize, however, is that as with everything Sandra does, this new training has a purpose. But when she announces an event to be held at her mansion in the coming week, a gathering of several other powerful individuals, realization starts to creep into his mind.

Soon he’s faced with a new dilemma. Obey his mistress and put his new training to good use or disobey and face her wrath.

“To earn your reward you will have to completely forget that you’re a man. You will need to believe that you’re a woman. That you are a sexy and sexual creature ready to serve me and do my naughty bidding. Do you think you can do that? Do you think you can earn your reward?”

Derek’s job as the billionaire Sandra’s sissy maid continues as she tightens her grip around him. Through training and domination she trains him to be her perfect obedient maid and servant.

On one fateful day when Derek does an exceptionally pleasing job, Sandra has a change of heart. She decides that after five long weeks of obedience and good behavior, Derek has finally earned a reward. But in order to earn it, he must pass one final test.

Sandra will put him through a trial that will show him what it means to be a true sissy. A trial that will change his life. Forever.

Suddenly shaving my legs didn’t sound so bad. Suddenly dressing as a maid seemed enticing. I could have everything I ever wanted and all I had to do was surrender my manhood to this billionaire.

Dressed as a maid with shaved legs and a chastity cage, Derek awaits the return of Sandra, the billionaire who was forced him into the position of servitude in her remote hillside mansion. Hoping it means the end of his tenure as her house keeper, Derek makes sure to be on his best behavior.

But his performance as her maid has piqued Sandra’s interests and she’s not ready to give him up yet. With promises of a better life, Sandra offers him the permanent job as her maid. She can give him everything he ever wanted; all he has to do is continue being her sissy maid.

And do everything she says.

The black dress, the white trim, the little apron, and the white petticoat. All together they made up a French maid’s outfit. It suddenly became so clear. She was calling me her housekeeper, but she really meant her maid. She meant to control me through humiliation.

Derek’s life was as comfortable as it could be for a college student without a permanent residence. This was thanks to his job as a house sitter which helped him both pay for tuition and provide a roof over his head. But when he gets a new job at a secluded hillside mansion, his easy job suddenly takes a turn for the worse after he breaks all of the home owner’s rules.

Soon Derek is scrambling to please the house’s billionaire owner, Sandra, who gives him two options: commit to doing everything she commands or face the consequences of his actions. Things quickly escalate as she pushes him to prove his devotion and obedience to her.

In order to keep his job and livelihood, Derek will have to push himself beyond his comfort zones in order to keep his livelihood.