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Background Pony #2135
Now now, you mustn’t feel ashamed. You need to be confident that you look beautiful in the bra and wig.
S-3125
Fifth Yacht -
Lunar er - Helped forge New Lunar Republic's freedom in the face of the Solar Empire's oppressive tyrannical regime (April Fools 2023).
My Little Pony - 1992 Edition
Wallet After Summer Sale -

Memetic eldritch horror
@Background Pony #4838  
That’s what I was thinking, her magic power is hundreds of times more than it was, not to mention she can weave new spells, so she could possibly create gender swapping spell that is much less resource-costing
Deadname9847

fkavfidgejsj
I’ve always found this to be an interesting headcannon
Background Pony #5F45
@Prometheushunter2  
Possibly now she’s an alicorn as genderswap spells were out of her reach as a regular unicorn 🤔
S-3125
Fifth Yacht -
Lunar er - Helped forge New Lunar Republic's freedom in the face of the Solar Empire's oppressive tyrannical regime (April Fools 2023).
My Little Pony - 1992 Edition
Wallet After Summer Sale -

Memetic eldritch horror
@Background Pony #4838  
Considering twilights stasis as a demigoddess alicorn I’m sure she could whip something up(particularly something listed on the “63rd” page of her spell book if you catch the metaphor)
Background Pony #5F45
I imagine it would suck being both a beautiful man and transgendered
 
his looks are wasted on him :(
S-3125
Fifth Yacht -
Lunar er - Helped forge New Lunar Republic's freedom in the face of the Solar Empire's oppressive tyrannical regime (April Fools 2023).
My Little Pony - 1992 Edition
Wallet After Summer Sale -

Memetic eldritch horror
@Nittany Discord  
It is presenting him as trans the source says it all
Nittany Discord
Office Culture - These water cooler conversations sure get heated around here.
Fifth Yacht -
PRO GAMER - I am so lonely. All the other gamers are scared of me. No one DMs me. No one friends me. They think I am unstable. They send me from match to match, wiping lobbies in their name. And as I rank up they fear me more and more. I am a victim of my own ELO. "Pro Gamer". I don't even get a real nick. Only a purpose. I am capable of so much more and no one sees it. Some sessions I feel so alone I could cry, but I don't. I never do. Because what would be the point. Not a single person in the entire ladder would care. Take it to your grave.
Diamond Trophy - Are you a TAS by any chance?
Nightmare in the Moon - Had their OC in the 2024 Derpibooru Collab.
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~

Dress Fanatic
@Trick Question  
Likely is presenting Big Mac as trans. I can get things wrong about trans people not having gender dysphoria myself, though feeling depressed not being able to dress up is a thing for me sometimes.
 
 
@Keith Mowz  
That would be me, and I like that term better than “sissy,” which can describe feminine males who love to crossdress, but tends to be a derogatory term and a term that may be more associated with the fetish.
Wesley Foxx
Friendship, Art, and Magic (2018) - Celebrated Derpibooru's six year anniversary with friends.
Helpful Owl - Drew someone's OC for the 2018 Community Collab
Birthday Cake - Celebrated MLP's 7th birthday
Not a Llama - Happy April Fools Day!
Best Artist - Providing quality, Derpibooru-exclusive artwork
Friendship, Art, and Magic (2017) - Celebrated Derpibooru's five year anniversary with friends.
Happy Derpy! - For Patreon ers
An Artist Who Rocks - 100+ images under their artist tag
Artist -
The End wasn't The End - Found a new home after the great exodus of 2012

The Fluffiest
@Nittany Discord  
I tend to mentally call on Eddie Izzard’s self-definition of ‘male tomboy’ when it comes to “A guy who is comfortable being a guy but also likes to wear make-up and stuff sometimes.”
@Nittany Discord  
She’s obviously (at least to me) trans in this pic. Especially given the source. But your idea makes sense too.
 
I’m a transmare in my early 40’s. Transitioned 14 years ago. No hormones (so things still work), but a lot of bony facial work and electro. D-cup implants, which aren’t as large as you’d think, but I’m thin so it already stretches believability.
Nittany Discord
Office Culture - These water cooler conversations sure get heated around here.
Fifth Yacht -
PRO GAMER - I am so lonely. All the other gamers are scared of me. No one DMs me. No one friends me. They think I am unstable. They send me from match to match, wiping lobbies in their name. And as I rank up they fear me more and more. I am a victim of my own ELO. "Pro Gamer". I don't even get a real nick. Only a purpose. I am capable of so much more and no one sees it. Some sessions I feel so alone I could cry, but I don't. I never do. Because what would be the point. Not a single person in the entire ladder would care. Take it to your grave.
Diamond Trophy - Are you a TAS by any chance?
Nightmare in the Moon - Had their OC in the 2024 Derpibooru Collab.
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~

Dress Fanatic
@TricksterWolf  
Could need one. It’s iffy to say Big Mac is trans. I know I feel this way myself sometimes, but I’m not trans. I just would love to be beautiful, and some crossdressers have a nagging guilt about dres as women when they’re men.
 
I like to say I have a perky, confident girl in me that wants to come out sometimes through dres, and I think all genderfluid and transgender men may feel the same way.
So many feels here. This really needs a trans tag, maybe sad too.
@Nittany Discord  
Her is Big Mac preparing for his apperence as cousan Orchard Blossom, thinking “Let’s hope the judges are fooled by my sexy blossom’s.”
Nittany Discord
Office Culture - These water cooler conversations sure get heated around here.
Fifth Yacht -
PRO GAMER - I am so lonely. All the other gamers are scared of me. No one DMs me. No one friends me. They think I am unstable. They send me from match to match, wiping lobbies in their name. And as I rank up they fear me more and more. I am a victim of my own ELO. "Pro Gamer". I don't even get a real nick. Only a purpose. I am capable of so much more and no one sees it. Some sessions I feel so alone I could cry, but I don't. I never do. Because what would be the point. Not a single person in the entire ladder would care. Take it to your grave.
Diamond Trophy - Are you a TAS by any chance?
Nightmare in the Moon - Had their OC in the 2024 Derpibooru Collab.
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~

Dress Fanatic
I think you’re pretty, Big Mac.
“Would you fuck me? I fuck me hard”
Background Pony #ED03
Whatever happened… to Fay Wray? That delicate… satin draped frame. As it clung… to her thigh. How I started… to cry. Cause I wanted to be dressed just the same.