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How would she do that? I was thinking they'd be living together in Fluttershy's cottage. It'd be easier for Fluttershy to suggest it to Dash or kinda force it on her in some way.
Well with Rainbow Dash and Fluttershy, Rainbow Dash would be wearing diapers for Fluttershy for whatever reason suits your fancy. I do love to play a sub Rainbow Dash.
With Scootaloo, either Dash or Fluttershy would have taken her in from the orphanage. They'd have lived together for awhile and Scootaloo starts having a few accidents and her mama decides it's best to go back to diapers for the time being. That would include a bit of babying as things progressed, such as a pacifier when she sleeps or a bottle before bed.
Heres a random Omake if Harry in Wizard and the lonely princess or what we could do in our rp if Harry started a trading business with Equestria
Omake name Melons;
"Okay, here are the rest of them," Twilight Sparkle called as she entered Harry's tower. Her magic had the fruit she was carrying bouncing slightly in the air as it followed her. She barely got through the entryway before being scared out of her life.
"RAWR!" Venus shrieked as she pounced at the newest Princess of Equestria. Twilight Sparkle screamed like a filly and dropped to the ground. Her magic disrupted, the fruit fell towards the ground. The Alicorn twitched as Moonshine and Nightlight followed Venus. There were sounds of a scuffle, and what sounded like one of the males getting kicked in the face. As Twilight poked her head up she could hear slurping noises and the occasional crunch.
Nightlight was laying on his back, his wings and legs outstretched. A hoof-shaped bruise was forming on the end of his muzzle. Twilight tried not to wince as she saw his eyes swirling slowly in their sockets. Venus was wrapped tightly around one of the melons. Her hooves and wings held it close to the mare's chest. Venus's fangs were buried deep into the large, green fruit. Her eyes blazed with unholy glee as she slurped away at her treasure. Moonshine had managed to snag a smaller, green and tan melon. He was glaring at Venus while he sucked the fruit dry.
"What the hayis going on here?" Twilight demanded.
"Well, we learned two things," Harry answered with a sigh.
"And those are?" Twilight snapped angrily.
"Uh, first Equestria doesn't have anything like a watermelon."
".. and second?"
"Well, judging by how fast those three got violent over them, I don't think I need to worry about profit margins for importing this stuff."
And that's how Harry Potter became Equestria's first legalized drug dealer.. since it was rapidly discovered that watermelons were addictive for Bat Ponies.