Woodwinger

Woodwinger is another non-player character from our MLP themed pen and paper role playing game. Our characters were introduced to him in a town called "one horse village" (yes, the name described the size of the tiny settlement) when we were on our way to attend the second ever summer sun celebration in Canterlot.
I consider him one of the most interesting non-player characters in our game especially because of the character development he took and a rather interesting relationship to my own character sketched out below.
Woodwinger worked as a scout to lead us through a part of the Everfree Forest that was on our way to Canterlot. We didn't know at the time that he was not just a member, but even a rather high ranking figure within a rather shady organization we were yet to encounter. That emblem on his collar (supposed to be a stylized tower with a wall surrounding it) later turned out to be a sign for that group.
Woodwinger wasn't a particularly talkative pony and often had an air of resigned cynism about him which at first our characters ascribed to his rather secluded life as a scout.
While crossing that part of Everfree we were attacked by some vines resembling those we saw in the opening episodes of season four. In a hilarious, turn of events our characters ended up saving an injured Woodwinger's life (a result of unexpectedly bad dice roll results for this character whom our game master had made so he could save us in case the dangers of Everfree should turn out too much for us).
At a later point Woodwinger gave my own character, Leafhelm, the cryptic advise to tell we were friends of him when "things get ugly".
By that time we had received several other strong hints that something "ugly" was in the making.
It took some time until we met Woodwinger again after he left us in Canterlot. When we did meet him again our characters had some fair idea about the kind of organization he belonged to. This encounter in a storehouse in Vanhoover's dockland area during a very stormy night was once again a rather hilarious affair of unexpectedly bad dice results. When Woodwinger fled, Leafhelm tried to follow him across the sea during the nightly storm. It turned out that he was going to escape by which time I decided to take a big risk to talk to him. I had my character pretend that he was falling in the storm, hoping that he would remember being saved by Leafhelm and the others (none of whom was out in the storm though) and therefore try to return the favor.
The pretended spin turned into a real one and Woodwinger indeed turned into a lifesaver for Leafhelm. There was a rather cool talk the morning after that storm (on a tiny island), after which our characters parted, respecting one another but knowing that they stood on different sides for the time being.
Next time we met was in "Finstersims" (roughly translates to "Dark Ledge"), a lair of our nemesis, the head of the organization who were the antagonists of our adventure. Leafhelm had sneaked in there (while the rest of the group had taken a more direct approach). Within the At that time Leafhelm had found definite evidence that Woodwinger was being deceived and exploited by the head of that organization. Risking that he would turn him over to that head, Leafhelm revealed his presence to Woodwinger and confronted him with the evidence finally convincing him to switch sides and help us.
We were to meet him again, but I cannot write anything more at this time lest the text includes spoilers for my fellow players

Thanks and credit for the beautiful background go to matty4z. Thank you very much for creating and offering backgrounds such as this one to other artists