Planning for Progress

Planning for Progress- rough draft v1

After your conversation, you lead Nate into his room. It's a space you haven't spent much time in since you've moved in, but now it feels like an essential part of the new journey both of you have embarked upon.

"Nate," you begin, sitting on the edge of his bed. "If we're going to do this, I need you to show me everything. Your sissy, femboy, feminization items, any related media you have. Everything."

For a moment, Nate looks apprehensive. But then, his expression clears, replaced with determination. "Okay," he nods, rising from his seat. "I'll show you."

One by one, Nate brings out his collection. There's a range of clothing, all feminine - frilly skirts, stockings, lingerie, and high heels. He also has a few wigs and a makeup set, still in their packaging.

"I've tried on some of the clothes," Nate admits, a blush staining his cheeks as he looks down at the garments. "But...I didn't really know what I was doing. And I've never used the makeup or the wigs."

Your eyes sweep over the collection. It's clear that Nate has invested time and money into this. It's also clear that he's been lost on how to proceed. But that's where you come in.

"Alright, Nate," you say, standing up and clapping your hands together. "Let's make a plan."

Over the next few hours, you discuss his experiences so far, his preferences, and his limits. Nate reveals he loves the feeling of silk and lace against his skin, but is unsure about tight clothing. He's also nervous about practicing his female voice and is absolutely terrified of doing his own makeup.

The more you talk, the more you see how much Nate has been holding back due to his fears and insecurities. You assure him it's okay to feel this way, and together, you come up with a step-by-step plan.

"First, we'll work on getting you comfortable in the clothes. We can take it slow, try on different things, see what you like best," you outline, watching as Nate nods along. "Then, we can move on to makeup. I'll help you, we'll practice together. We can even have some fun with it."

Nate's eyes light up at that, a smile spreading across his face. "That...that sounds nice," he admits.

"And then, when you're ready, we can work on your voice," you conclude. "Does that sound good?"

Nate looks up at you, eyes shining with gratitude. "Yes," he says, his voice barely a whisper. "Yes, it does."