Sissy Dressing up in Lingerie and Stockings for His Mistress

I caught my sissy dressing up for me.

A sissy dressing up is no new thing for me. But it is quite a fun little adventure, especially the first few times. See, my submissive boy toy recently discovered that he’s a sissy. He absolutely adores getting dolled up for me. The best part is that I caught all of this by surprise! He used to be another submissive pet for me to play with. I already used strap-ons and toys to peg him with. However, once I caught him trying on some of my lingerie… I knew he was a sissy femboy after all. He wasn’t just someone who loved to be submissive and get pegged. My sissy dressing up in my panties wanted the full show!

And, of course, I loved to go along with it. I love to make him take everything a step further. The day I first caught him being a sissy is still one of my favorite memories with him. Oh, he wanted to be such a good boy. We had been teasing and joking all day through text. I told him to be ready for me when I got home. Of course, I thought it would be like any other day. To warm up and be prepared for me, he would usually use a vibrating butt plug. ‘Cause it would be time to play with the big toys once I got home. I didn’t think that I would catch my sissy dressing up for me, though!

It was so exciting to see him dressed up.

When I stepped into the house, I made my way upstairs to find him in the bedroom. No surprise there until I saw what he was doing. I expected him to be playing with a toy, already naked or halfway there. Honestly, I didn’t expect to find him trying on my little pink thong! I knew it was mine because it was one that I had recently bought. It’s a little holiday panty, so it has red lace trim and tiny jingle bells on it. Very festive and sexy. And this little bitch got to wear them before I did! I couldn’t help but giggle as I saw my sexy sissy dressing up for me and checking himself out in the mirror.

He blushed bright red when he saw that I had caught him. And that made it all the more fun. “Oh, you’re my little sissy bitch now, huh?” I scolded him, my tone a little mean, but playful nonetheless. “You want to wear my brand new lingerie before I even get to break it in?!” I indulged in all the different ideas that came to mind. I could punish him with a little masochist play and use some ginger powder mixed in with his lube to make it really ‘spicy’ for his ass. Or, I could dress him up completely so that he could get the full experience. Oh, I felt wicked. Catching my sissy dressing up for me was turning on so many ideas.

My sissy dressing up for me was such a treat.

Now, I had plenty of new ideas to play with him. Before, he had just been a little submissive pet. I’d trained his ass well with my strap-ons and butt plugs. But now, he would do everything I commanded. And the first order of business was to complete the look. He couldn’t just wear panties. My sissy dressing up in the thong was just the first step. I ordered him to fish out a few more things from my dresser and closet. Within seconds, I matched the pretty panties with a set of fishnet stockings, black stiletto heels, and a matching pink and red lace bra… And to top it all off, pink liquid lipstick that I knew could survive the sloppiest of blowjobs.

Once he was all dolled up for me, it was time to strut his stuff. And, of course, I had to give him a new name to match. His name was now Daisy. Her name was now Daisy. What a wonderful day it was for Daisy. A brand new look, a brand new name, and the exciting experience of strutting around and walking in heels and stockings for me. That pink thong perched perfectly between her cheeks as she modeled it for me. And, of course, the show wasn’t complete without a good spanking. After the fun of my sissy dressing up, she needed her cheeks to be spanked bright pink to match the thong… Tell me, baby. What should I make you wear to match that thong?

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