This is a three part commission I did for DeviantArt
To say Michael's life was entangled with Sara's was an understatement. In the four years they had dated, they had not only got engaged but Michael had given up his rented condo to move in with his fiancee, and they even shared a bank account. So when their steamy relationship eventually blew cold, it was not as simple as moving out and starting over. Michael had nowhere to go.
Sara no longer loved her ex but she wasn't cruel. She allowed Michael to keep living in her basement until he found his own place, but there were conditions. Her sister Steph would be moving in immediately to take over Michael's share of the rent when he eventually left and to act as something of an umpire between the feuding former lovers, albeit one that was obviously biased in favour of one over the other. Steph's name quickly replaced his on the lease, and Michael found himself subletting from two women who held his shelter entirely at their mercy.
Steph made no secret of the fact she hated Michael. This was not a new thing. Right from the inception of his relationship with Sara, she had despised the way he looked down his nose at her as a divorcee. It was as if she was a broken toy, unwanted, a cast-off, and the moment she moved in with Sara, she made haste to settle the score for this and the way he had treated her sister. A week into her residency, she descended the steps to Michael's basement with a garbage bag in her hand.
“Right, listen up you worthless dork.” she scowled, tossing the bag at Michael's feet. “Sara might be a bleeding heart, but I sure as shit am not. You have two choices. You can either gather up all your crap, put it in that bag and leave right now, or you can stay, but what is in that bag there becomes your new identity for as long as you are still in this house.” She watched as Michael picked it up and spilled out its contents. Out fell a blonde wig, a cotton dress, patterned pantyhose, layered panties and a pair of platform Mary-Janes, and open fell Michael's mouth. Steph watched him try to process what she had just said then added. “If you don't choose one of these, I tell Sara you tried to grope me and she throws your ass out anyway!”
Michael didn't really have two choices. Having nowhere else to go and no access to his own money, his only option was to become Steph's plaything and she knew it. Over the next few hours she took her time transforming him, first ordering him to pull on the pantyhose and the underwear followed my the dress and shoes. Steph reserved the honour of placing the wig on his head for herself, thereby completing his new look. Michael caught his reflection in his floor to ceiling mirror and humiliation immediately washed over him. He looked ridiculous.
“Good,” Steph nodded, “now put your old clothes in the bag. This is what you will wear from now on. We'll start your training tomorrow!” With no choice but to comply, Michael began to gather his shirts and put them in the trash bag.
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