My Sissy Outfit Humiliation

I love wearing my sissy outfit! My Feminization Mistress loves when I dress up for her. She insists that I be totally dressed in my best sissy clothes whenever she sees me. She goes shopping with me and helps me buy the pieces that look best on me.

We’ve been to fashion shows together and had all kinds of shopping experiences. My Mistress has owned me for several years and I trust that she knows what’s best for me. I wasn’t out when we first started. She taught me to love myself by making me face who I was and what I needed. I haven’t ever regretted a moment with her.

I Love Sissy Outfits, But a TuTu?

I have flown all over the world with her looking for the best sissy outfit clothes. She has taken me to the top designers and makeup artists in the world, so I know what looks best on me. We once went to London on a shopping trip and had the whole store to ourselves for an hour. I tried on shoes, dresses, bras and panties.

It was so much fun! Then we went to the ballet and all I could think about was how much I wanted to try on a tutu! I happened to mention it to my Mistress, and then I forgot all about it until it came time to do my duty as a slave at her next get together.

Sure enough, there was a little pink tutu laid out for me to wear instead of my usual sissy maid’s uniform. Wearing the tutu had just been a fantasy, so I was not sure if I liked the idea of one being my outfit for the evening.

Sissy Ballet Shoes

I dressed slowly, reluctantly. As I pulled on the pink hose, I wondered how my Mistress found Pointe shoes in my size. Then I remembered that men who dance in the ballet do wear them sometimes. I put the shoes on. They were stiff and not broken in at all and hurt my feet. But beauty has its price, or at least that is what I kept telling myself as I walked around the room, trying to break them in a little bit.

I decide that I will try to get my Mistress to reconsider her choice of outfits for me. Even as I think this, I know she won’t change her mind and if I whine too much about it, she will be mad and punish me for complaining.

But I thought I would give it a try. I quietly and respectfully asked her if I absolutely had to wear the tutu in front of her friends. She looked at me sternly and said that, yes, I had to wear it. She went on to say that, it had taken her a lot of time and money to find and purchase a pink tutu for me.

She told me that she was very disappointed in me and that I should not say anything at the party as punishment. I nodded and hung my head. My Mistress doesn’t stay mad for long, though. She then turns back to driving and says that I did a really good job with my makeup. I beam with pleasure.

Then she smiles and says, “Good makeup for a loser sissy.” My face falls and I sigh.