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Family picture! (just to clarify, I simply didn't include berry because they don't live in the same household, he's not any less part of the family, though he's indeed closer to his dad's side)

I'd like to say I chose to give Cheerilee a bit of a stronger and rougher earth pony build. She's fairly taller than the average mare, and is pretty strong for one. She needs to be ocasionally able to press a misbehaving stupid teenager or two to the ground when they refuse to go to detention lol.

On the other hand, Clear skies is petite~ Wind Sprint grows up to be a little taller than her because of her dad's genes.

Rosemary is a slight mix of Cheerilee's built and Clear Skies' small figure~

As a way of going deeper into her background story, I'll go a bit into how Rosie's mothers came to be <3

Clear Skies is probably from somewhere in manehatten, or at least used to live there for a couple of years. Clear's occupation revolves around cleaning, organizing and optimizing environments so ponies can make the best use of it, which was a job very frequently called for in the big city of manehatten. Everypony had their own rushed and busy schedules they didn't have time to organize their houses or working spaces, to the point that it would affect their productivity and quality of life. Clear was there to solve that problem.

It was a couple of years after her husband passed away that she considered dating someone again, tho she didn't really focus on it, and wanted to spend time with her daughter the most. Even so, a couple of relationships with one or another stallion would eventually come and go, but none of it really seemed to work out. Realising the big city wasn't really a friendly and enjoyable place for a single mom and a little kid to live, Clear Skies decided to move to ponyville with her daughter Wind Sprint. Ponyville was a very lively and peaceful small town that had a much bigger feeling of community. Much more contact with nature as well as better place for Wind to enjoy her passion for sports, also knowing ponyville was where one of the best teams of hoofball resided.

Since ponyville is a much more quiet and simpler place than the big city of manehatten, Clear Skies' former job wasn't really much requested. She'd often help out older ladies cleaning up their houses and give the grocery shopping employees a hand on organizing the shelves. But she was used to the rush of the big city, so she couldn't really spend much time sitting still. As a way of also focusing on her daughter and being around while she grows, Clear Skies decided to be a volunteer for the Ponyville's Schoolhouse. There she would meet Cheerilee, who she'd spent a lot of time with, since the teacher was responsible for overseeing all sorts of school events, specially for the youngeer fillies. Clear Skies would help with class organization, planning family meetings, events, and sports festivals. They would bond over their love for younger children, both being single moms (since at that time, little Mulberry was around the age of a little colt too). Eventually things just flowed naturally from there. Clear would grow closer and closer to the mare, not realizing her feelings for a while. Cheerilee was the first one to confess as she had realized her feelings first. Clear Skies was confused as she never really felt anything or had even considered a relationship with a mare. But they eventually sorted it out and live happily together now~

Now have some random family relationship notes!

- Wind Sprint was never a fan of her mother remarrying again, and is a bit of an ass about it, but I guess Miss 'Lee makes her mother happy so it should be fine.

- Clear Skies loves both her daughters deeply. She knew Wind always seemed to want a sibling back when her dad was still around, but she tends to put Wind Sprint's happiness first and sometimes wonders if remarrying and having a child was the best for her daugher, rather than considering her own happiness too.

- Clear Skies realizes her relationship with her daughter was never truly the same after her husband passed away. Wind had a very close bond with her dad, and feared every guy her mom had dated after him would end up being a replacement for him. They both love eachother a lot, but have lost a bit of communication over time.

- After both Wind Sprint and Rosemary grew up, Clear Skies felt a bit nostalgic and somewhat empty inside. She missed the feeling of caring and tending for a little one, their warmth, the feeling of being needed by someone and give them attention. So she eventually took over the Day Care Division on ponyville's school district, as well as also helps at the nursery sometimes.

- Cheerilee is very patient with Wind Sprint regarding their relationship. She knows she's not a fan of her and neither sees her as a parent figure, but tries to be of some guidance to her, even if it's just as a superior from school, and hopes she'll come to her for advice. She won't force a relationship on her. Wind Sprint is the sort of kid that went "I'm not calling you mom" ever since Cheerilee and Clear Skies started dating. She learned to be less bratty about it and reffers to Cheerilee simply as Miss 'Lee, as she would also do withing school grounds.

- Cheerilee has a very close bond with Rosie, she just sort of frowns upon her daughter's lack of commitment and academic perfomance, but at least she seems to be doing ok.

- Clear Skies is the parent Rosie seems to be closest, specially because they both spend a lot of time together in the Daycare. Clear seems to be very fond of how Rosie grew up to be such a kind and upbeat pony. It gives her such a peaceful and nostalgic feeling as it reminds her of her late husband.

- As much as Wind Sprint did want a sibling back then when her dad was still alive, she was still very immature and very reluctant about her mother's relationship when she was younger, so back in a lovely spring morning, when her mother and Cheerilee presentend little newborn Rosemary to her at the hospital room, her first reaction was "I don't want it. Give it back to where it came from", which probably left her mom speechless and pretty embarassed in front of the doctor. But even so, ever since that moment when young Wind Sprint stared angrily at clueless baby Rosie, she seemed to have imprinted on her. And Rosie came to grow very attached of her sister, and has been barging in in her life every since.

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Also, just to clarify, the Ponyville Schoolhouse Cheerilee used to work in has been upgraded over the years and have become a much bigger educational facility. Cheerilee's performance over the years has earned her lifelong dream of being nominated school principal~

Anyway hope you like it! Don't worry there's still more to come

Upvotes at import: 54 | Stars at import: 33
Posted previously at: 2020-04-27T13:27:42 | Posted previously by: Mildgyth