Picking

He was excited, today was the day he and his wife started their "agreement", that he could wear female clothes on two conditions: she got to pick what he wore and he had to box up and put in the attic all his male underwear.

"Why do I have to box things up?" he'd asked her.

"Because if I'm letting you be feminine, it's you being feminine. It's not just a when you feel like it thing, it's an everyday thing."

"What...what about, I don't know, the doctor or things."

"I'll take that into account when I'm picking what you wear," she said, "not everything has to be frilly, but it's panties 24/7."

"Okay," he swallowed. 

"You ready?" she asked him, clearly excited.

"I...I suppose," he said.

"Let's go," she said, taking his hand, "time to play dress up Barbie."

He let her lead him to the bedroom, excited to see what his wife picked for him, excited to finally be allowed to be feminine around her. When he saw what was on the bed, his excitement increased; she'd picked a pretty pink and black slip, panties, nylons, heels, and even breast forms. 

"You like?" she asked.

"I...I love," he said, walking to the bed, stopping when he saw something else. "What..what's that?" he asked, staring at the object between the breast forms.

"What?" she asked. 

"T..that," he pointed.

"Oh, that," she smiled. "Sorry, I thought you meant the breast forms and knew you knew what those are. I assumed you knew what a chastity cage is, too."

"I...I know what it is," he said, taking a step back, "I mean why...what's that doing here?"

"It's part of your outfit," she said, "you agreed I got to pick what you wear."

"I...I can't wear that," he stammered. 

"The lingerie? I thought you'd like it..."

"The...that," he pointed to the cage.

She folded her arms, narrowed her eyes. "I thought you wanted to wear pretty things," she said.

"I...do," he said.

"And I thought I got to pick what you wear," she said.

"Lingerie," he stammered.

"No, everything," she said.

"But that...that locks," he said.

"Of course it locks," she said, "that's kind of the whole point. I'm not dressing you in pretty lingerie to have you jerking off all day. If you want to wear these, you wear that, too."

"For...for how long?" he asked.

She smiled, knew she won, shrugged. "Whenever you're wearing lingerie," she said.

"No, how...how long until...you know..."

"Sweetie, I'm not promising you anything, it's going to stay on until I think you've earned some free time."

"Like how many days?"

"Days?" she raised an eyebrow.

"Weeks? You want me to wear it for weeks?"

She smiled again, pleased. "I guess I was thinking in terms of months."