• Member Since 24th Mar, 2019
  • offline last seen February 21st


Crossdressing Pony


born in Canterlot, Azure grew up in a high society life, his family wasn’t rich, but they had enough to be secure. As a Colt, Azure loved to dress up, ponies usually didn’t wear clothes, but in Canterlot, almost everypony wore something, whether it was simple day wear or elegant evening wear for events and parties. Azure’s love was mostly for suits and tuxes, but he also enjoyed the occasional costume. He loved pretending to be someone else for the day, he even wrote stories about his pretend alter egos.

One day, his older sister, Rose Diamond, was playing with Azure and his costumes when she thought of a way to tease him, she dared him to wear her old Princess costume. Not wanting to be seen as chicken, Azure accepted. When he slipped the costume on, his heart jumped a little, and when he saw his reflection, he blushed at how cute he looked, If he didn’t know any better, he wouldn’t have guessed he was a boy. He had more fun that day than ever before. Days past and he soon started trying on more of his sister’s dresses, then it grew to lingerie, then he bought himself a wig and tail extensions, and he even tried on makeup. He was amazed at how good he looked as a girl, in fact, his Unicorn magic gave his body a more feninin appearance, he was a perfect trap and he liked it, he would then answer to the Name Sapphire when he was a girl.

As a boy, his personality is that of gentle colt: he’s polite, well, mannered, though he can have fun like any other guy. But when he is feminized and becomes Sapphire, He’s more playful, bubbly, and very flirty. He’s not afraid to kiss another colt, in fact, he gets whatever chance he can to steal a kiss from someone he finds cute

That’s when the cutie mark came. a male symbol with the trappings of lady undergarments. The book on top represented his well-read nature and his love of writing and reading.

He kept this love of being a Filly to himself, his sister and to a lesser extent, his parents when he was growing up. He was often teased about how girly his cutie mark was but Azure explained that it represented his understanding of Stallions and Mares. This went on for some time until he was accepted into an exclusive school for unicorns. It was there he met his first real friends: a Gothic pony named Morgana and the more outgoing Night Archive. They were fascinating ponies to him, outsiders, like him. He was shy but their acceptance of him made him feel all kinds of good, so good that he felt these two would understand his real feelings.

As he got older, the desire to be Sapphire grew more and more, and he soon started to think of Colts in a romantic way. The feeling came so much so that he couldn’t stay in the closet forever, He started dressing outside, usually going to night clubs and, on occasion, after school. He told his friends and they were accepting: Morgana found that Sapphire was more Girly than most girls, and Happy gave him makeovers and the dresses she never wore anymore. Night Archive, who was bi-curious, had asked Sapphire out on a date, they went steady for some time until differences caused them to end their steadiness, but they remained friends to this day.

Comments ( 6 )
  • Viewing 2 - 6 of 6

Thanks for the follow! :yay:

I do, and it seams you found me. ^^

do you have a da account?

Thank you, she's quite popular with my Discord group heh. And if you need more background characters feel free to use her. If you've got any questions I'll be happy to answer them.

ooh, she looks very pretty

  • Viewing 2 - 6 of 6
Login or register to comment
Join our Patreon to remove these adverts!