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The Frilly Sissy In Training

The frilly sissy in training is a favorite sissy type for me. I mean who doesn’t LOVE sissy dress up time? Today I had the pleasure of playing sissy dress up with a sissy in training. I love the colors of black and pink together, so sissy found the cutest outfit. I was a very pleased Mistress!

Shopping With Ms. Delia

Sissy Dress Up Mistress

The Dress Up Outfit

First came frilly pink panties with the cutest hold for the sissy stick. Next came a cute black bra that was rather plain. I must say again that the art of being a sissy is all about accessorizing!

The next item for frilly sissy dress up was a pink and black tutu all frilly and ruffled in a hot pink and black color scheme. Pink glitter shoes were next and added that sexy sissy bling.


Sissy Accessories

The final accessories were a lovely pink and black posture collar and matching writs cuffs, and sexy black clothes pins for the nipples. A pretty pink, curly wig topped off this sexy frilly sissy. She really was a sight to be seen. A true vision in pink and black.

Sissy Sent Me a Reflection

After my phone session Miss Delia asked me to stay dressed and reflect upon my thoughts. I was wearing a wig upon my head, wrist collars, a posture collar, a bra, panties, a tutu and heels, all in pink and black. My thoughts were that I was comfortable yet easily reminded that while moving about was a reminder of my predicament. I was left thinking I look forward to serving Miss Delia!

Do you love sissy dress up? Are you a humiliated sissy when dressed up? What is your favorite outfit?

9 comments to The Frilly Sissy In Training

  • Peter

    I’d love to play dress up with you and the other mistresses. My favorite is women’s leggings with knee high boots. That’s so hot and sexy that I bought women’s legging and 2 pair of women’s knee high boots. The girls at my salon wear them and I get hard when I see that. I feel weak when women wear the knee high boots. Also wearing bras/panties/slip with pumps and lipstick. Ms Audrey had me wearing this and she put white tip press on nails on me also. If we play dress I’d like it to be corced feminization where you trick/tease me into you & other mistresses dressing me up as a girl. It’s time I start back up calling you as one of my mistresses in the feminization circuit.

  • I love a frilly sissy the outfits that we get to dress them up in are adorable and so UN manly that they make me giggle, I love to have a frilly sissy prance about in her puffy dresses and tutu’s now tell me do you enjoy seeing them twirl for you hehehehe

  • Delia

    Oh Ms. Constance

    YES! This frilly sissy knows how to twirl and dance!! 🙂

  • Ms Delia ~ I do not think I will ever get over how much I love to play dress up. I just do! Each and every time is so much fun. Whether is it sexy, slutty, pretty, for just fun it just thrills me. As you know, black is my favorite and I just adore the black and pink theme together. Oh all those accessories! So much fun and your sissy enjoyed it so much. Thank you for sharing it with us.

  • Delia

    Agreed, Ms Kay Marie!! Sissy dress up is the best!


  • Peter

    Would the 2 of you play dress up with me as part of my feminization circuit? With the 2 of you dressing me up I couldn’t escape. I think dressing me up would be punishment for spying on the 2 of you especially with me holding bra in my hands as well as wearing yoga pants/leggings with girlish turtleneck sweater wearing heels/boots.

  • Delia

    I guess we Mistresses will decide and coordinate that when you are ready for the circuit training. But anything is possible!

  • Peter

    I understand and respect that! Just need to find head mistress as well as day/time to start calling. I’m thinking tomorrow to begin feminization circuit. I want to do 15 mistresses.

  • sissipig heather

    Love the “Humiliated Sissy” link in this post to a superbly written intelligent essay on what being a humiliation loving sissy is like and more. I always enjoy the psychological aspect of the scene from the perspective of both the sissy and the Domme. Thank You for this Ms. Delia!

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