In my last post, My Take on the Sissy Pageant (The Photo Judging), I talked about how glorious it was to see the photos the girls submitted to the crew of Mistresses.

Once the girls were finished with their photo shoots, we moved on to the second part of the pageant; the questions.

4 Questions for Sissy Pageant Contestants

• • What is your biggest Sissy or crossdressing challenge? What parts of being feminine are most tricky for you to handle?
  • If you could travel back in time and give yourself any advice about your sissification and feminization journey, what would it be?
  • Crossdressing is great, but how do you maintain that Feminine feeling when you’re not all dressed up? Think in terms of Undercover or Stealth Femme tricks, your little daily Sissy Rituals, and Sissy Attitude!
  • Sissies, crossdressers, and trans women often have an idea in mind about what their perfect Ideal Femme Self Image might look like. Describe your vision of who you would like to be!

How I Judged the Words Written by the Ladies

This is where things got really difficult.

I’ve talked to thousands of sissies, cross dressers, transwomen, drag queens, and everyone inbetween in my lifetime. Both on the phone and in real life. I’ve taken on sissies as a project before. I know a lot about what goes on in the mind of a sissy.

However, the answers to the above questions were simply fascinating and eye opening even for me. We Mistresses have been given permission to use some of what the girls said, so when I quote something, there is absolute permission to do so. I would never betray anyone’s trust.

Amazing Quotes from Amazing Women

…clothes don’t make the style, it’s the attitude.

I would tell myself to not be scared and just be yourself. I would also tell myself to enjoy being a sissy and dress how you want because you will have so much more fun…

…this is not a light switch you turn on and off. it is in my being to want this.

I’ve established a weekly Sissy Ritual, where I shave my legs and my body after I shower and I also have an affirmation about being feminine and a sissy. I tell myself: “It’s great to feel like a gurl and it feels great to be feminine.

It’s acceptable and it’s natural. “I’ve established a weekly Sissy Ritual, where I shave my legs and my body after I shower and I also have an affirmation about being feminine and a sissy. I tell myself: “It’s great to feel like a gurl and it feels great to be feminine. It’s acceptable and it’s natural.”

It would be to wake-up and smell the coffee at an earlier age for real. If I would have paid more attention and understood my feminine nature at the start I believe (know) I would be further along on my sissification path as well as happier with the result.

Painful Quotes These Wondrous Sissy Pageant Women Shared

I would go back and tell my past self to be careful with strangers online, especially when I wasn’t 18 yet.

Just because you feel that it’s wrong, that doesn’t mean that it is. You are just scared and very deep in the closet and once you come out and truly embrace it, you can be the princess you always wanted to be.

I found myself getting carried away, and ended up with may more than I could ever wear – a lot of the pieces I was buying did not fit well, either. This led to a lot of shame on the amount of money I was “wasting”. Since then, I have found ways to manage my collection (without purging), but I feel if I had been more in control of my shopping/spending early on, I could have avoided so much shame and negative feelings.

It’s often a battle of shame and guilt, betraying the real man my GF thinks I am to indulge being a pathetic sissy instead. But it’s also so much fun to just give in to all the insecurities and thoughts of not being ‘man enough’ and embrace being a total fucking sissy. I hope I’ve got the right balance in my life.

You Girls Are Sooooo Not Alone!

What does reading these statements, thoughts, even confessions, do for your heart? Does it swell the way mine does? Do you feel more a part of a club who understands you? Gosh, I hope so because that is exactly what I feel. I so hope these comments (and I will share more soon) are able to soothe your soul that you have companions along your journey.

My being involved in the kink and fetish world for almost 30 years has taught me a lot. I’ve heard my share of confessions, but they have never been written down so that I could read, re-read, and ponder their meaning and feelings. I’m telling you folks, sissies and non-sissies alike, if you are not journaling somewhere, somehow, you have to find a safe place to do so. Your words are quite profound!

I want to thank allll the participants of the Sissy Pageant for their trust and belief in the Mistresses to hold your secrets with respect and understanding. We Mistresses are privileged to know all of you… whether you were in the Sissy Pageant or not.

Let me know your thoughts in the comments.

Sissy Pageant contestants or anyone else who is
moved by these precious words.