OOO boi I finally finished it! Also before you ask, "HeY wHErE iS flAM/!1/!?!?/" I was too lazy to add him, maybe I'll add him in the future.

(left to right)

1st Generation
Twilight Velvet — Mother of Twilight Sparkle and Shining Armor
Night Light — Father of Twilight Sparkle and Shining Armor

2nd Generation
Trixie and Twilight — Mother's of Magic Trick (Trixie got pregnant during a very, VERY drunk one night stand.Trixie carried the child while Twilight used a spell to have male gentles for 2 hours. The friendship was lost when they found out she was pregnant.)
Flim and Twilight — Mother and father of Red Thorn and adopted Dusk Star
Shining Armor and Princess Cadence — Mother and father of Flurry Heart, Snow Storm, and Crystal

3rd Generation
Magic Trick — Daughter of Trixie and Twilight
Red Thorn — Son of Flim and Twilight
Dusk Star — Adopted Son of Flim and Twilight
Flurry Heart — Daughter of Shining Armor and Princess Cadence
Snow Storm — Son of Shining Armor and Princess Cadence
Crystal — Daughter of Shining Armor and Princess Cadence

Welp hope you liked it.

Inspired from BlueberrysDrawings

Also thanks to kilalaaa for making the first next gen guides.

Also adorkable Twilight

Applejack version here