I started drawing this image as a cover for the recently (at last) created deviantart folder for art based on a pen and paper role play game adventure I have been playing with friends and fellow bronies since late summer 2016. Since I started drawing this I learned a couple of things about how to draw ponies and how to work with vectors. So there are a number of things I wouldn’t do the way I did in this picture anymore, but I didn’t want to start all over from scratch again either. The image shows the main player characters (some of whom have by now left the group, hence the slightly melancholic title) during the first adventure of the group in front of a background showing the location of the first adventures big showdown. From left to right (and top to bottom) the characters are:
 
Shockfire, a 16 year old unicorn who used to be a non-player character until our then game master liked her so much that he adopted her as his character once one of the other players took over the role of the game master. Shockfire (or Shocky for short) was one of the “Shutties” (the organization who provides most of the antagonists of our adventure) until we captured / liberated her in a memorable brawl in a storehouse in the harbor of Vanhoover. Shocky doesn’t remember her life before some three years ago, when she was picked up by her elder sister (who was in the organization) from an orphanage in Canterlot. Trying to bring back her memory and find out about which role she and her sister play in the schemes of the main antagonist has become one of the central plotpoints of our story. Shocky has pretty much been adopted by the group with Leafhelm in particular playing kind of a father role.
 
Elderberry, a unicorn from Canterlot who joined our group there when we were sent to explore an outpost (set up in secret by Commander Hurricane decades ago) in the far west of Equestria. Elderberry is a calm and levelheaded botanist. Unfortunately real life circumstances of his player (studies) forced him to take leave from the group after the conclusion of the first big adventure.
 
Windseeker, the blue coated and green maned pegasus Windseeker joined our group under somewhat confusing circumstances in the town of Vanhoover. Windseeker is an 18 year old physician with a somewhat harsh backstory. His parents were pegasi embassadors in Canterlot but brought… somewhere by Discord when Windseeker was still a foal. He was adopted by a unicorn family and makes a point of wanting to be a unicorn. Ocassionally Windseeker’s viewpoints have clashed with those of other characters (with Leafhelm’s in particular) and have led to many rather interesting and entertaining debates. Windseeker’s wings are somewhat oversized and since he rarely used them (other than for and I am not kidding!) sweeping the floor!) he is not much of a flyer.
 
Empyrea, it turns out Spike was not the only ever dragon to live among ponies. Empyrea had to flee from her original home after warning a tribe of zebras about an impending raid by her kin. Empyrea found refuge in Celestia’s Equestria and even got a job as Equestria’s first ever mail dragon. Of all the characters in the group Empyrea probably endorses the Element of laughter best. Obviously a dragon may cause some strong reactions in Equestria 1000 years ago. It would have been impossible to allow for a dragon character in this game (with the overpowered abilities not exactly suited for Equestrian style problem solving, such as breathing fire) but for her player being as far from a ruthless “power gamer” as can be. One poor decision about the use of her firebreath and a poorer diceroll still have led to one of the harshest situations in our adventure which however provided a lot of material for good storytelling.
 
Leafhelm, is the character I am playing myself. The original idea was for him to be an earthpony, but since we had one earthpony already but no pegasus at the time I gave him wings so we would have all tribes present in our original group. Leafhelms parents (who served under commander Hurricane) and his older sister are somewhat traditional pegasi working in the “military”, while Leafhelm never really fit into that role. The helmet he is wearing doesn’t have anything to do with his job. He is a mapmaker. Leafhelm was considered somewhat “unicornized” (Rainbow Dash would probably say “eggheaded”) by his fellow pegasi, even though he loves flying and embrasses being a pegasus. Leafhelm is very much of an idealist but can also be somewhat paranoid. It just so happened that he of all characters was given some insight (through a vision inducing brew of a zebra) into the sinister ends to which the actions of the adventure’s main antagonist would lead and ever since he has been trying to get this point across to the others in the group.
 
Graystan, is a strong and sturdy earthpony stonecutter. More down to earth in every respect of the word than any of the others in the group he is the last to condemn anypony for actions unless he sees them causing any harm. He is straightforward, easygoing (much of a live and let live attitude) and difficult to disconcert, but if he is threatened or sees others being threatened one is well advised not to get anywhere in his stonebreaking hooves’ way.
 
The fortified place with the dark tower beside the gap in the background was dubbed “Finstersims” (Dark Ledge) by our group. It used to be a small outpost secretly set up by Commander Hurricane on the western outskirts of Equestria in the early years of the reign of the royal sisters. Some eleven years prior to the events of our adventure the main antagonist got to the place (mostly abandoned and turning into ruins) and set it up as one of several operation bases for his schemes. It was at Finstersims that our first adventure had its big showdown. However, said showdown was far from a finale and the story goes ever on and on