Tony to Tanya

"I thought you were already dressed up for me." I said, slightly confused.

"I am. These are for you." She clarified.

It dawned on me what she wanted me to do. I have no real negative views of dressing up as a girl, I just never thought I'd do it before. And I never knew that Sarah would want me to do it. I was shocked to have it being sprung on me so suddenly.

"You want me to-" I started.

"Dress in my old school uniform? Yes" she finished for me. "You don't mind do you? You said you'd try almost anything and this isn't one of those 'extreme' things that you ruled out of trying."

"True." I thought it over. "Since it's just between you and me, I'll do it but it's not something I'd ever thought of before."

"It'll be easy. This'll fit since we're the same size." She told me.

She wasn't wrong. I don't have the same figure as her, but I'm not muscular or anything. My body's toned and slim. Her old uniform would fit.

"I don't quite see where this is going." I said.

"You will." She assured me. "Let's do your make-up and then you can change in the bathroom while I prepare everything else. Wear this, as well." She finished, throwing me a black lace thong.

She did my make-up: a bit of eye-shadow, a small amount of blush and some pink lipstick. She brushed my hair as well, making me look like a very pretty girl when it was all done. I set off to the bathroom to change.

I stripped to my boxers, put the blouse on and buttoned it up. I couldn't believe I was going through with this. I then took my boxers off and pulled the thong on, I had to rearrange myself so I was comfy. I pulled the skirt and socks on with no difficulty and my nervousness was starting to disappear.

When I had the shoes on I stood up and looked in the full-length mirror. I was astounded. I looked immensely cute and shy, like the new girl in school. It was as if I wasn't looking at myself.