My Sissy Outfit
My 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 Clothes, But a TuTu?
I have flown all over the world with her looking for the best 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. 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.
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Humiliated at the Party
We arrive at the party and I walk to the door with my feet dragging. I hang my head as the door opens. Standing at the door is one of the people I work with. Looking at me in the tutu makes him burst out laughing. I’m so shocked to see my co-worker that I am speechless. I peer into the doorway, unable to believe what I’m seeing. Oh my God, she’s invited all the people that I work with. I feel so humiliated that I think I might pass out. Unable to move on my own, I feel my Mistress take my arm and lead me into the kitchen. She commands not to cry and instructs me to start serving drinks to everyone. I take a deep breath, look down at my Pointe shoes and think that it’s only a few hours. Then I pick up a tray of champagne glasses and toss myself back in the living room.
I survived that night. Everyone I talked to laughed at me and called me a loser. The guys from the mailroom told me they wanted me to come to their favorite bar dress this way. The bitches from the secretarial pool wouldn’t say anything. They were laughing too hard. Even my boss was there! My God, what was going to happen on Monday back at work? See if I ever say anything about wearing a tutu ever again!
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