It was a beautiful Saturday morning.
"Here's twenty dollars," Rachel said as she took the majority of his cash and all of his credit cards out of his wallet then offered it back to him with the single twenty dollar bill in it. She dropped it a split second before his hand reached it and he had to bend down to pick it up off the ground. She took a moment to see if any of the other shoppers in the mall were watching.
He was almost fifty and fit (thanks to her) and this morning she made a big deal of dressing him for this outing. She picked out a nice dark brown Tommy button down shirt and Ralph Lauren denim pants. He almost balked at the shoes but instead squeezed his men's size eleven feet into the red four inch pumps without protest. She special ordered them for him the week before and they came with a matching red belt.
She had never submitted him to cross dressing before so his walk out to the car from the house and then from the car into the mall was the sum total of his experience in heels. He did not fall but he looked ridiculous. Having to bend over to get the wallet further amused her.
"Dude, what the fuck are those?" one out of a group of skater boys in their teens asked as they walked past while pointing at his shoes. The other's looked and laughed loudly while pointing and calling out insults. "Your dad's a dork!" one said to her and she giggled at how red his face turned.
"You aren't my dad, you're my bitch," she whispered to him. "Say it."
"I am your bitch Lady Rachel."
"Why?"
"Because I am not a woman as I have a cock. Yet I am also not a man because a real man, even the lowest example of the gender, would never look to raping an employee as an acceptable course of action, which is exactly what I did when I made advances toward you when you worked for me."
"That's exactly right!" she said with a smirk as two elderly women passed them while whispering to themselves. She made him memorize that response over the last two years and to this day made him repeat it at least twice a day.
"I gave you options remember?"
"Yes Lady Rachel."
"What were those options?"
"To turn myself into the police immediately and confess my crimes was my first option. To mutilate myself by removing my own testicles, which are the source of my perverse desires, was my second option. To submit to your will completely was my third option."
"And you chose?"
"The third option Lady Rachel."
"And what has that cost you?"
"Confession of adultery to, and consequential divorce, from my wife, estrangement from my children, surrender of my business, my house, my cars, my boat, and the lavish lifestyle to which I was accustomed."
"And who are you Monday thru Friday?"
"I am Ben Dillard; Maintenance Supervisor of Dillard properties."
"And on nights and weekends?"
"I am Ben the creepy douche, on call bitch boy to Lady Rachel, and slave to her every whim."
"That's right!" She chuckled. She was really hoping he would mess up but he obviously had his lines down by now.
"So how do you like it?"
"It is bliss." He knew to try to make this last line sincere and it made her giggle.
He kept his hands at his sides the entire time he spoke and never made eye contact with her. It was such a change from the cocksure executive who asked her to stay late and help him with a project when she was eighteen. It was probably tough to maintain the masculine swagger he used to have while wearing four inch heels and carrying the memories of all the humiliations she subjected him to.
Then he was a long time friend of the family and one of her father's golfing and fishing buddies. In a million years she never would have suspected he might betray the trust her family put in him. When he made the pass at her the violation was not to her sexual innocence, that was long gone already, it was to her faith in the adults in her life.
"Can you stay after hours and help me go over the Peterson contract?" he asked her. She almost rolled her eyes. He waited until everyone else was gone for the day and she was heading for the door. She was his newest and least qualified to go over any contracts employee. She reached into her phone and set it to record audio while pretending to send a text. She put the phone back in her purse. At that moment she figured, hoped, it was probably nothing.
She was shocked he was doing it and curious to know if he would actually go through with it. He did. They completed the project in less than an hour. Now they were alone in the office together and she hoped he would do the honorable thing and let her go. When it was done he invited her into his personal office instead. She brought her purse. He asked her about school, her grades, and what she wanted out of life as he poured himself a Scotch from his office mini bar. She answered dutifully, her curiosity did not allow her to encourage nor discourage his actions.
"How old are you?" he asked as he took his first sip and turned to face her.
