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The story is this was Derpy's first turn at the stick in her flight training. All of the T-38's were down for maintenance so her and Dash went up in a Tomcat (the only other 2 seater on the base). Things went good until the landing attempt. A strong crosswind + new pilot= problems. After several near collisions with stuff on the ground Dash was ready to pull the eject handle, but somehow Derpy landed it... as you see here.
Worse yet Luna was touring the base when this happened. However when she saw it, it was all she could do to keep from busting a gut laughing. She managed to get it back on it's wheels with her magic.
Next up: Bombing practice.
No other Derpy image would've worked as well for this (I think it's the best one).
RD's callsign is Viper.
If you don't recognize the plane behind RD, it's because it's a custom I made. And if you're wondering: All of my Tomcat models will stand on their tails like this, which is why I picked it. Sure it's impossible in real life, but this is a cartoon where the laws of physics don't seem to apply to some ponies , and magic is everywhere.
And of course as Sylvester the cat once said "anything is possible in a cartoon".