With the 2024 Sissy Pageant officially wrapped and our Queen and Court crowned, it’s time to check in with our participants and learn their top crossdressing tips and advice! We had such a great turnout for the Pageant this year, and as part of the process we asked each individual vying for the crown a few questions, so we could judge them on their personalities and insights as well as their lovely outfits and poses. From those answers, a picture emerges: sissies and crossdressers have a shared experience and tons of great advice to give. If you feel like you’ve been all alone exploring your private desires, let these astoundingly brave people’s responses reassure you: you are not alone, and what you’re experiencing is actually really common!

Crossdessing Tips: A Shared Experience In Femme Clothes

Overwhelmingly, when asked what advice our Sissy Pageant participants might want to give to a younger version of themselves, the responses were “to embrace crossdressing and feminization without fear”!

“If I could travel back in time, I would tell myself not to think too much about what others will think and to let go of my fears. Focus on finding a supportive community that accepts and embraces my sissiness.” ~Tina

“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 and be able to wear amazing clothing.” ~Sissy Chrissy

“I would love to have the opportunity to travel back and tell a much younger me that wanting to be feminine is perfectly ok and to start accepting and enjoying it much sooner.” ~Daizee

Again and again in the responses the sissies, crossdressers, and other participants (however they may identify themselves!) told us in clear and cogent phrasing that they have a shared point of view on the world. The truth shines through that embracing yourself and your desires is absolutely key!

Find A Community

Another of the important crossdressing tips and major point shared by participants is the importance of finding a community of supportive and encouraging people to join. No one is an island, and for those who enjoy feminization and crossdressing, the isolation that fear of rejection creates is simply too terrible. Build for yourself, or find and join, a community in which who you are is welcomed and supported. The Enchantrix Empire is the social media site run by the Mistresses of LDW, and I can assure you that it is just the sort of community you would likely get a lot of positives from. But don’t take my word for it!

“If LDW had existed at the time, I probably would have visited. Because it would have given me the courage to start earlier. I’ve always been so ashamed of it. But it was a different time, it’s much better now. I even told myself at the time that it was a temporary condition and that I would be “normal” again…:) I would like to see things in those days with today’s eyes. On the other hand, I believe that things are as they should be.” ~Casandra

“I would say to myself: Don’t worry about what a lot of people think. They’re just jealous that you’ve decided to embrace your femininity when they don’t have a clue about what it really means to be that way. In fact, surround yourself with people who not only understand your choices, but also help to support and embrace the real you.” ~Sissy Regina

” I would tell myself to wait to use this new thing called the internet to search and find a woman that not just tolerates your sissy desires, but loves them and wants to help you with them!” ~Laci Sissy

Top Crossdressing Tips From the Pageant

It is important to accept yourself and find a community to support you, but there’s some good solid practical advice and crossdressing tips in the responses too! Regulating and controlling your shopping habits, making use of already existing groups online, including podcasts and sissy forums, and of course, the importance of being up front about your needs and desires.

“When I first started exploring my feminine side, shopping for clothing, lingerie, and panties was (and still is!!) so much fun. 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.” ~Emma

“If I could travel back in time and give myself advice about my sissification journey, I’d say, “There’s a treasure trove of podcasts! And buy Bitcoin early to fund your sissy wardrobe.” Just kidding! The real advice would be: “At the end of the day, it’s you who you have to lay your head down with at night. Who cares what anyone else thinks about you?”” ~Kendal

“Three words…”Don’t get caught!” LOL! I would have to go a loooong way back in time . Not even sure if Doc Brown’s Delorean could get me there! There must be enough pixie dust here in this forum to work it’s magic. Now remember…I am old…older! Back when I first stepped into a pair of moms undies? there was no colour TV at our house, no cable, phones were on the wall…(i know!) I’ve often quipped in blogs comments that i am ‘BI” and go on to add “Before Internet” Back then crossdressing was only portrayed as comedic farce, an embarrassment. And in places, illegal. Unfortunately i have been careless and discovered totally unintentionally. It has been very tough. My advice to a young me? Be upfront from the start with any relationship. If you need this in your life now you always will. I was wrong and now i see this. However this is not a light switch you turn on and off. it is in my being to want this. Don’t take that chance and hurt someone. Take the blows now as opposed to later.” ~Sissy Pageant Queen Little Peg

The Sissy Pageant Is Over For Now

The Sissy Pageant has ended for now, but will be back next year, so if you’re sad you missed out on all the fun, just consider that you now have a full year to brush up on your skills and get ready to shine on our catwalk! Soak up all these crossdressing tips and tricks and apply them for your debut on our stage. Head over to the Enchantrix Empire and join in on the community waiting for you there. We have groups for makeup tips and tricks, the Outfit Of The Day, and more! Share your pictures and ask all your questions of the sissies, crossdressers, and Mistresses! Our social network is inclusive, accepting, and welcoming to everyone (as long as they’re over 18). You can also listen to the live award show on demand: The Sissy Pageant 2024 Award Show is online.

Congrats To The Winners!

Congratulations to all our Sissy Pageant 2024 winners! Second Runner Up Lynn, First Runner Up Genie, and our Queen Little Peg! The participants also voted for their own Miss Congeniality, Casandra! All the participants are winners in my book, because it takes so much bravery and strength to enter a pageant in the first place. The clear vulnerability displayed in the responses to our questions, the fortitude it takes to put yourself out there and share pictures of yourself online, and the wonderful support and camaraderie on our social media site made this Pageant one to remember.

Click above to hear Ms. Harper.

Your Crossdressing Guide, Mistress Harper