He had no other choice

Jake took a good look at the pile of clothing and ponder his choice. He had chosen to come there to help Mia pay off the debts of her father and by doing so he accepted to wear woman's clothing and probably do some nasty things along the way, but all this had a way to excite him. He could already feel the subconscious training the organization put him through moving him on the path of slutiness. At that point, the other possibility was to refuse to wear the clothes and be dragged naked and ashamed through the facility to receive obedience training.

Jake took his courage thinking of Mia. When they will pay the debt they will be able to return to their normal life and all this will be an old nightmare to be forgotten. Jake was so naive at that point, but he will soon learns that the organization has something far more sinister for him and Mia.

First, Jake slowly put the panty on. To his surprise, they were soft and comfortable. His small bulge was barely visible. The next step was a bit more difficult, the bra. Jake struggled to hock the bra. He lost precious minutes there. As he zipped the skirt in places he heard the door opening.

"Are you ready miss? I have strict orders to bring you to the chosen training area or down in the dungeon if you don't comply." said a deep voice, but rather sheepishly. Right at that moment, Jake moved out of the bedroom wearing the outfit given to him. The bra was too big for his meager breasts and barely filled the lingerie.

"I am ready," said Jake and the man jump a little. His voice was still a man, but the person he saw could easily be mistaken for a woman. Without saying anything else, the man escorted Jake through the labyrinthic corridor of the establishment he was in.