How Roleplay Builds Confidence

Roleplay Into Reality

I know the braver you get as a woman, the more you want to try new things. Sometimes those things are scary: going out dressed as a woman, finding a person to date, going out shopping for makeup even dressed conservatively. I’ve found that engaging in some roleplay about those and other situations often build confidence.

Makeup Shopping

Imagine wanting to go to the makeup counter at your favorite store. You have done lots of reading and research online, but once faced with the infinite possibilities it can become overwhelming. So many options you hadn’t even considered! New bright sparkly fancy colors! I know what kind of makeup I prefer and I get pulled in by lip stains! So, if you want to practice shopping for makeup and facing the clerk, this is the place to be!

Conversational Roleplay

If you are nervous about going to a bar or club dressed up, give us a call and we can talk through possible scenarios you may encounter during your night out. Practicing the conversations through a vivid roleplay can give you the tools to hold your own in multiple conversational possibilities.

Flirting Rehearsal

Worried about what to do if you are approached by someone you aren’t interested in? We can rehearse your response options through a roleplay session! Nervous about what to do if someone you are interested in tries to flirt with you? Practice your reactions with an LDW Mistress.


  1. MissRachel March 5, 2019

    Excellent advice, Miss Stephanie! Many sissies think of roleplay with Mistress as a *substitute* for experiences out in the world, and if that’s the extent of what their situations allow, well, wonderful! But as We well know, many sissies are looking for ways to take their sissy selves to the mall, the spa, the shoe store, and everywhere else, and they’re simply in need of encouragement, such as you supply here, through roleplaying through their nerves!

  2. Paulina June 12, 2019

    I’ve gone makeup shopping before. I was nervous as I had on women’s slacks ankle boots/women’s turtleneck sweaters along with panties/bra underneath. I had list of what I wanted. Cute salesgirl asked if I needed help and said yes. She asked who makeup/lipstick was for and I told her me. She smiled/picked out lipstick/makeup for my skin then asked if I wanted to sit in chair which I did. She said to relax and put makeup samples/lipstick on me. Her hands were so soft as she touched my shoulder she noticed bra strap underneath and giggled. I let her have her way with me and didn’t care who noticed. It was rush and thrill. I thanked her and she told me to stop again. I’m really her cream puff girl. I haven’t been back since as too many people know me and I need to and will take day to myself and go dressed and out of town to do this again.

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