Background: Applejack, her older brother BigMacIntosh and her younger sister Applebloom, were born to Romeo and Juliet-inspired pair, Bright MacIntosh and Pear Butter, two children from two different families, which unfortunately hated each other. Young couple, despite their families, decided to date, get married and have children of their own. Their parents and other family members didn't really come along with it and went no-contact with newlywedds. Only one, who was in some contact with them, was mother of Bright MacIntosh, who we know as Granny Smith. Pair didn't get much of a life together, since both of them died, so Granny Smithed stepped in and raised the three children.

Big MacIntosh (Big Mac)
Of course, he got very soon married to his sweetheart, Sugar Belle and they had a son called Sugar Twist Apple. But marriage did not last much long, because one day a little colt appeared on doorstep of the Apple family home. The little one had some personal items with him and letter explaining, who this little stubborn guy is — affair baby from quick one night stand Big Mac had with Marble Pie long before he got married.
Marble Pie discovered her pregnancy too late and decided not to crush the wedding and instead raise the baby — little Strawberry Apple Pie. But years later, Marble Pie wanted to get married, but her son did not really approve and tried to break his mum with her fiance — Bulk Biceps. Marble Pie decided to send him to live with his father.
Strawberry was forced to live with his suprised new family, but suprise quickly changed into anger. Sugar Belle took her son and divorced Big Mac, who tried his best to keep the family together and accomodate everyone. The divorce was messy, but court decided for 50/50 custody agreement for their son Sugar Twist Apple, who hated his dad. Sugar Belle eventually got remarried to some Apple family member.
Big Mac was then raising his son alone, but never ever told him it's his fault, he really wanted to bond with him, but Strawberry was full of resetment, anger and sadness. He was problematic before, but now he was just worse — constantly running from home and being rude toward anyone.
His heart softened a little when his dad married his long time crush — Fluttershy, who ,at the time of the wedding, was already very sick. She gave birth to Big Mac's third and last child, the third son in a row, called Shy Blossom Apple. Since this traumatic experience, Fluttershy was mostly bedridden, but still loving and caring to both her son and stepson, who really bonded with her and showed her that he is not a bad horse, just acting up because of emotions bottled inside.
He sadly did not get to enjoy much of her love, because when his younger brother was quite little, he got lost in nearby forest and his mother, despite her sickness and weakness, tried to find him. Shy Blossom Apple was found and rescued, but his mother lost her life in the wildeneress. Strawberry was heartbroken, but loved his little brother even more, because he was just so happy that at least one of them turned up. Since this incident, Big Mac has been living alone with his sons as a widower.

Applejack
Applejack got married quite young to Trouble Shoes. Their marriage wasn't bad, but they were better off as friends and co-parents to their daughter Baked Potato, than lovers or romantic partners, so they got quickly divorced. Applejack tried to play it off as best as she could, but became an alcoholic and had one night stand after another, not caring who it was.
So it was no suprise, that she suddenly had one filly after another — first it was Soarin, the husband-to-be of her friend rainbow Dash. She made out with him on his own wedding and Rainbow Jack found out. She decided to forgive her husband, but made Applejack swore up and down not to ever speak to Dashie again. Applejack later gave birth to Spicy Apple, son of Soarin, who consented to short visitations, but colt lived most of the time with his mum.
Shortly after, she slept with Braeburn, her own cousin, and had a son again. This little fella got the name Peaches Apple, but since he was born from incest, he was allergic to apples since birth, but still went to live with his mom.
Applejack got into her deepest depths of alcoholism, which she doesn't remember much from. She one day discovered that she is expecting again, but she cannot remember who the father is. During her pregnancy, she tried to track down the baby daddy, but got lost just one step before uncovering his identity — it was either Flim or Flam. Later she gave birth to twins Berry and Terry Apple, who resented her for not knowing and sharing the name of their dad (or dads?).
Applejack, still an quite bad alcoholic, went on to sleep with Rainbow Blaze, brother of Rainbow Dash, which made Dashie even more angrier on her former friend and became bitter. From this one night stand was born very beautiful daughter, Sweet Carrot. Applejack did not tell her who her father was, but rumours got around because this little young lady was becoming more and more pretty day by day and her colourful maine was very unique for Apple family, but not for Pegasi, who tend to be much more colourful, especially from the Dash bloodline.
The last one night stand was Trenderhoof, who took advantage of Applejack's problem — she again was pregnant, but now she decided it needs to stop. She was violated, she had many kids, but no stable daddy, and she had another baby on the way. Before this, she was not a bad mum, just absent for some days. She decided to take Trenderhoof to the court, but the charges were mostly dropped. He only payed childsupport. Applejack would swear it's because he's a celebrity even today, years later. With Trenderhoof, she had a daughter, Applehoof.
Applejack recovered from her bad habits, became super mom and got married to Caramel and had her last baby — Honey Cinnamon Apple. She never regreted her past, because she had her kids from it and they were such a blessing for her, that she could never traded them for a clean past.

Applebloom
The youngest Apple daughter at the time tried her best to be, in her words, "better than her sister" and be in a stable relationship. But twice, she got into the Applejack and Troubleshoes kinda situation — good relationship, but without any love.
First one was Pipsquak, who matured into very handsome young stallion. Applebloom enetered relationship with him, but never marriage. She gave birth to their two sons — Scruby Nubs and Marble Sprinter, but shortly after, they separated and colts were with their parents 50/50.
Applebloom tried dating Snails too, but even before their daughter was born, he cheated and left her. Applebloom gave her daughter name Hazelbloom and worked a 50/50 custody with Snails.
Third time, she got luck and got married to her long time crush — Tender Taps, who just divorced Diamond Tiara. Shortly after wedding, their firstborn daughter Sugar Taps came to be. Not long after her, Applebloom gave birth to her last child — daughter Spring Bloom.

Program: Paint.NET
Technology: ASUS Vivobook Flip 14, Wacom Bamboo Ink (2. gen)
Based on characters from show My little pony (Hasbro and Lauren Faust).

Base by none other than X-Vintage—Owl-X herself.
Other than that….I guess that's all. It took me like a week to finish this one, because…yeah, such a big family. And there are not included other members, only 3 Apple sibs.