The Crossdressing Discussion Thread

Nittany Discord
Roseluck - Had their OC in the 2023 Derpibooru Collab.
Elements of Harmony - Had an OC in the 2022 Community Collab
Non-Fungible Trixie -
Verified Pegasus - Show us your gorgeous wings!
Preenhub - We all know what you were up to this evening~
Twinkling Balloon - Took part in the 2021 community collab.
My Little Pony - 1992 Edition
Friendship, Art, and Magic (2020) - Took part in the 2020 Community Collab
Dream Come True! - Participated in the MLP 9th Anniversary Event
Economist -

Assistant
Dress Fanatic
@noobiestbrony  
I do love wearing things that hug my bits in a nice way and give me cute bulges like that. It’s fun to imagine my bits erect and pressed against my belly by something soft and snug.
Hippony

Just when I thought my crossdressing ideas were just a phase, I read your new posts and my desire to feel like a beautiful girl in lovely female attire goes back up and through the roof. Dangit, guys ! ;p
 
@Nittany Discord  
Crossdress bulges are very nice indeed :3
Nittany Discord
Roseluck - Had their OC in the 2023 Derpibooru Collab.
Elements of Harmony - Had an OC in the 2022 Community Collab
Non-Fungible Trixie -
Verified Pegasus - Show us your gorgeous wings!
Preenhub - We all know what you were up to this evening~
Twinkling Balloon - Took part in the 2021 community collab.
My Little Pony - 1992 Edition
Friendship, Art, and Magic (2020) - Took part in the 2020 Community Collab
Dream Come True! - Participated in the MLP 9th Anniversary Event
Economist -

Assistant
Dress Fanatic
@Hippony  
It happened to me around my early 20s. I thought my crossdressing phase has died out because crossdressing didn’t feel “good” anymore. However, it didn’t take long for me to start wanting to try on women’s clothing again, or to wear any gorgeous dress I saw and be happy in it.
Ciaran
ラ・ゼッタ - For supporting the site
Pixel Perfection - I still call her Lightning Bolt
Silly Pony - Celebrated the 13th anniversary of MLP:FIM, and 40 years of MLP!
Shimmering Smile - Celebrated the 10th anniversary of Equestria Girls!
Lunar Guardian - Earned a place among the ranks of the most loyal New Lunar Republic soldiers (April Fools 2023).
Crystal Roseluck - Had their OC in the 2023 Derpibooru Collab.
Flower Trio - Helped others get their OC into the 2023 Derpibooru Collab.
A Lovely Nightmare Night - Celebrated the 12th anniversary of MLP:FIM!
Princess of Love - Extra special version for those who participated in the Canterlot Wedding 10th anniversary event by contributing art.
Tree of Harmony - Drew someone's OC for the 2022 Community Collab

Senior Moderator
友情は魔法だ
@Background Pony #BA9A
Oh my god I love those. I’ve got two: one for logging and wood working, and the other for working in the garden.
They’re so nice I wish I could wear them for work. I might even get one for that - the one I’m wearing to work now is way too formal for T-Shirts.
Ciaran
ラ・ゼッタ - For supporting the site
Pixel Perfection - I still call her Lightning Bolt
Silly Pony - Celebrated the 13th anniversary of MLP:FIM, and 40 years of MLP!
Shimmering Smile - Celebrated the 10th anniversary of Equestria Girls!
Lunar Guardian - Earned a place among the ranks of the most loyal New Lunar Republic soldiers (April Fools 2023).
Crystal Roseluck - Had their OC in the 2023 Derpibooru Collab.
Flower Trio - Helped others get their OC into the 2023 Derpibooru Collab.
A Lovely Nightmare Night - Celebrated the 12th anniversary of MLP:FIM!
Princess of Love - Extra special version for those who participated in the Canterlot Wedding 10th anniversary event by contributing art.
Tree of Harmony - Drew someone's OC for the 2022 Community Collab

Senior Moderator
友情は魔法だ
@Nittany Discord
Everything from half a decade ago is potential cringe.
I was taking a class from Lea Hernandez and asked her how she deals with the horror of a blank piece of paper, or the cringe of seeing what you did in the past. And she said;

“Oh, honey - it only gets stronger. But you have to ask yourself; do you want to draw or not?”

If you are alive, and you are a creative, then there is a great chance that you will have an ‘internal editor’ who hates everything you do. They will never go away - they will only get stronger. But if you listen to them, you won’t be creative.
Steven Pressfield’s “The War Of Art” does an amazing job of talking about “Artist Resistance” and using that lurking dread and cringe to figure out what you should be working on, and what you should be giving to someone else or ignoring.
Interested in advertising on Derpibooru? Click here for information!
Techy Cutie Pony Collection!

Help fund the $15 daily operational cost of Derpibooru - support us financially!

Syntax quick reference: **bold** *italic* ||hide text|| `code` __underline__ ~~strike~~ ^sup^ %sub%

Detailed syntax guide