Another Day at the Office

The next day, I couldn't stop thinking about Jack and what had happened on our date. I wanted to explore my desires further, but I didn't know how to tell Jack without feeling embarrassed or shameful. As I sat at my desk, lost in my thoughts, Jack approached me with his usual charming smile.

"Did you have a good time last night, David?" he asked, his voice low and seductive. I tried to compose myself, but the heat flushed through me at the sound of his voice.

"Yes, I did. Thank you for asking," I replied, trying not to sound too eager.

"David, I couldn't help but notice the way you were looking at me last night. There was something in your eyes that I couldn't quite put my finger on. Can I ask you something?" Jack said, his eyes fixed on mine. I took a deep breath, trying to quell the butterflies in my stomach.

"Yes, of course," I said, my voice barely above a whisper.

Jack leaned in closer to me, his breath hot against my skin. "Do you have a secret desire, David?" he asked, a hint of a smile playing on his lips.

I didn't know how to respond, so I decided to steer the conversation in another direction. "Actually, Jack, there's something else that I've been feeling lately. I've been enjoying dressing as a woman. It's like a diversion from my usual self, and I find myself wanting to explore that aspect more," I said hesitantly.

Jack's expression changed to one of curiosity, and he leaned in closer to me. "Tell me more about that, David. What is it about dressing as a woman that appeals to you?" he asked, his voice low and seductive. I took a deep breath, feeling a sense of relief at being able to express my thoughts. "I don't know, Jack. It's like I'm able to let go of all my inhibitions and be someone else. It's liberating in a way that I've never experienced before," I explained.

Jack smiled, his eyes lighting up with excitement. "David, my dear. That's wonderful. I can help you explore that side of yourself and guide you through the journey. Together, we can discover the woman inside of you," he said, his hand taking mine.