When the remaining characters of our pen and paper role playing game group (the earthpony Graystan, the pegasus Windseeker, the unicorn Shockfire and the dragon Empyrea) got to Cloudsdale after the presumed loss of their compagnon Leafhelm (which occured the day before his birthday) they had the sad task to brek the news about Leafhelm to his family (his parents and his older sister).
I got to admit that I didn't do a good job in making my character's (Leafhelm's) parents or his sister (who I am going to upload soon) look like they were related to Leafhelm mane- or colorwise.
Leafhelm's father Thunderhooves is sometimes jokingly referred to as "the old general" by Leafhelm and his sister (Whistlewing). He served under Commander Hurricane (of first Hearth's warming eve fame (or notoriety)) and indeed rose through the ranks to become a voice to be heard in Cloudsdale society. And speaking of his voice, while he is rather calm most of the time he can let his voice boom in such a way that it is impossible for it not to be heard even from a far distance. Rather strong and sturdy for a pegasus the old general has also become a little fat in his well deserved retirement (and is touchy about the subject). His Cutie Mark is a horseshoe in front of a thundercloud with three lightnings.
Leafhelm's mother Featherflight is friendly, welcoming and calm and a casual aquaintance may not realize that her former job with the Pegasi's "surveillance service" translates to basically "badass secret agent and scout in unknown territory". Her former job turned her into a rather astude judge of pony (or griffon) nature so she will not easily be deceived about anypony's intentions. Her cutie mark is a Feather with a lightning for a shaft.
Both of them were born before the first Hearth's Warming Eve, raised in a society in which the three tribes were separated and saw some "action" in a past conflict with Griffons (which would play a role in the later course of the adventure). While they occasionally show some nostalgic sentiment about the "old days", they generally believe that it is not just necessary but also an improvement to "fly with the winds of change". In the council of Cloudsdale they both spoke up in favor of the recent opening of the town for "unwinged visitors".
Thanks and credit for the beautiful background in this image go to Isegrim87.