What Are Fun Things Crossdressers Like to Do?
Crossdressing is more than just clothing — it’s about expression, freedom, and joy. For many people, crossdressing opens up new avenues for creativity, self-discovery, and community connection. Whether someone dresses occasionally or regularly, the experience can be deeply affirming and, yes — fun!
So, what are some of the things crossdressers enjoy doing when they’re dressed up? Here’s a list of popular activities that blend style, self-expression, and a great time.
Photoshoots & Selfies
Whether in a studio, at home, or outdoors, dressing up and taking photos is one of the most popular things crossdressers love to do. It’s a way to capture the look, showcase fashion choices, and document personal growth. Social media platforms and private communities offer a safe space to share these moments and connect with others.
📸 Tip: Set up a DIY backdrop or use a tripod and timer to get creative angles. Even a bedroom mirror selfie can become a confidence boost!
Shopping (In-Person or Online)
Trying on clothes, testing new styles, or browsing online boutiques is a thrill for many crossdressers. Shopping offers the chance to explore feminine fashion, experiment with new looks, and build a personal wardrobe that feels affirming.
🛍️ Hot tip: Look for stores that are known to be LGBTQ+ friendly or shop online to access more sizes, styles, and privacy if needed.
Makeup Play & Tutorials
For those into glam, playing with makeup is both a fun activity and a creative outlet. From perfecting the cat eye to contouring like a pro, makeup allows for transformation and personal expression.
💄 YouTube is full of tutorials specifically for crossdressers, with tips on face shape, beard cover, and enhancing feminine features.
Going Out Dressed
One of the biggest confidence milestones is going out in public dressed. Whether it’s for dinner, dancing, a drag show, or even just a trip to the grocery store, being seen and feeling confident can be a huge rush.
🌆 Many crossdressers find joy in:
Going to LGBTQ+-friendly bars or clubs
Attending drag brunches or themed events
Exploring crossdresser meetups or social nights
Trying on Lingerie & Breast Forms
Many crossdressers enjoy trying on different types of lingerie, breast forms, and shapewear. It’s a personal and tactile way to feel feminine and explore body shapes. Realistic breast forms, in particular, can help create a more complete silhouette and boost confidence in how clothes fit.
✨ Tip: Look for forms that match your body frame and style — realistic silicone forms can make a huge difference in how an outfit feels.
Journaling or Vlogging About Their Journey
For some, crossdressing is part of a larger personal journey. Journaling, blogging, or even starting a private Instagram or YouTube channel can be a way to share thoughts, build confidence, and track self-expression over time.
📔 Prompts like “How did I feel today dressed?” or “What outfits make me feel most confident?” can lead to deep personal insights.
Roleplay & Character Exploration
Crossdressing sometimes ties into exploring alternate identities, characters, or fantasy roles. Some enjoy developing full personas with names, mannerisms, and outfits to match. Whether for fun, fashion, or fantasy, it’s all part of the creative process.
🎭 Think: vintage pin-up, office chic, goth glam, or even full-on cosplay characters.
Connecting in Online Communities
From Reddit threads and Facebook groups to private forums and Discord servers, there’s a thriving online world where crossdressers share photos, tips, stories, and support. These spaces offer encouragement and ideas without judgment.
🌐 Some popular spaces include:
/r/crossdressing (Reddit)
Crossdresser Heaven
Trans-friendly Facebook groups
Fetlife for kink/fantasy-based dressing
Attending Crossdressing or LGBTQ+ Events
Larger events, conventions, or themed weekends can offer unforgettable experiences. Think makeup classes, fashion shows, group dinners, and more — all in an environment built for fun, freedom, and friendship.
🎉 Examples include:
Keystone Conference (PA, USA)
Esprit Conference (WA, USA)
Diva Las Vegas
Local Pride events or drag festivals
Just Being Themselves
Sometimes the most fun thing to do while crossdressed is… nothing special at all. Watching a movie, cooking dinner, reading a book, or lounging at home in your favorite outfit can be just as meaningful as a night out.
🧘♀️ It’s about feeling good in your own skin — and that’s always worth celebrating.
Final Thoughts
Crossdressing is about joy, exploration, and authenticity. What’s fun is different for everyone — and that’s the beauty of it. Whether you’re stepping out for the first time or just enjoying an evening at home in your favorite outfit, the goal is to feel confident, empowered, and happy.
At Wear My Boobs, we’re proud to support self-expression of all kinds with realistic, handcrafted breast forms that help bring your look to life. No judgment. Just support.
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