Scootaloo and Wind Sprint family in Shadowverse

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Scootaloo was the last crusader to get together with somepony and have kids, and as teenagers the three felt it might never happen, Scootaloo simply showed no interest in other ponies that way, or in having foals.

As Scootaloo grew up and saw both her crusader friends start having kids she felt a sort of alienation from them, she threw herself more into her aspirations, namely sports and her scootering, and spending time with Rainbow Dash when she could, though she was busy being a wonderbolt and also starting her own family.

Scootaloos wings never developed to the point of flight, she can use them to speed her up and slow her falls just like as a small filly, but getting in the air long enough to consider it flight just didn't happen for her. Scootaloo has a genetic condition that effected her wings, stunting the growth of the bones and muscles. Most fillies with this condition have sensitive wings, which are usually slower to flap or hang somewhat limply. Since Scootaloo had fairly strong flap power and perky wings, which she used to scooter faster, her condition went by fairly unnoticed and brushed off as a late bloomer thing, resulting in her getting no treatments as a filly to encourage her wing growth, leaving her with mostly flightless small wings.

This is something that has and always will bother her to an extent, but as shes grown she has become accustomed to how her wings are, and looks towards more grounded activities for herself. Maybe one day she will have a procedure done to get her natural wings replaced with something else, much like Rainbow Dash and her machanical wing, but such a surgery is very invasive and she hasn't had the time or bits to put real thought into it yet.
Her wings do work after all, just not for flight, and they don't give her any pain or discomfort.

As for getting to know Wind Sprint, well, Clear Sky and Quibble ended up staying together, and even have a foal together, and Rainbow Dash stays a good friend and support for Quibble, so the family would watch the wonderbolts events and visit Ponyville to spend time with Rainbow Dash, and of course this means RD's honorary sister enters the picture, meeting a young pegasus just as into sports as she is, and who has also grown a fondness for Rainbow Dash over time.

The two get along swimmingly, Wind Sprints talent is buckball so her and Scoots spent a lot of time on the field, playing with or against each other, Scoots playing the role an earth pony would usually fill. Scootaloo shows Wind her scooter and the old clubhouse, they visit the roller derby rink in ponyville, and just hang out together while their families are engrossed in each other. The two end up having such a good time together that they keep in contact, Wind ends up pestering her parents, for Quibble has officially adopted her a few years into his marriage with Clear Sky, to visit Ponyville more often.

The two were never openly 'lovey dovey' but it didn't take a genius for Scoots friends to see just how close she and Wind were getting, and no one was surprised when the two decided to announce their relationship.

Wind Sprint did become a professional buckball player, and plays for the ponyville team since she moved there to live with Scootaloo, but she had to put her career on hold for a bit to have their kids.
Scootaloo could have probably lived her whole life without kids and been just as happy, after all before Wind she assumed she would never have a pony to have them with, and she certainly wouldn't be having them anyway, the thought of going through pregnancy and birthing did not sit right with her at all.

But in Winds case, despite being a 'tomboy' of a filly, always wanted kids of her own one day. She had always had a good relationship with her mum growing up and always felt that kids would simply be part of her plan. Wind also always had a lot of strong female role models to look up to in sports ,and many of them had had children themselves and gotten right back into kicking flank on their respecive fields, so she Wind saw no reason she couldn't be just as awesome as those mothers.

So when the topic came up with Scootaloo Wind was more than willing to bear both of their children, so long as they both agreed they wanted kids.
Scootaloo agreed, and even agreed to be the kids main caretaker so that Wind could get back on the circuit as fast as possible, and they had their two babes.

Dare Devil : the eldest, she clearly gets her looks from Scoots side, and is as much of a risk taking filly as she was. She adores both of her mothers and aspires to be just as bold and amazing as them. She was a late bloomer flightwise, which worried Scootaloo and she had her checked by the ponyville physician regularly, in case she needs to take hormones to help her wings development, the kind that might have helped Scootaloo as a filly if her condition had been noticed, but she got off the ground eventually and her wing muscles are growing in nicely now.

Sunny Skies : their youngest, who came out bearing a strong resemblance to her grandmother Clear Sky, thus was named for her. She's not quite as daring as the rest of her family, but in relation to other ponies she's still practically fearless. She loves to cheer as loud as she can for her mothers or big sis. Sunny has yet to get off the ground, but after Devil's late bloom Scootaloo isn't quite as panicked about it, but she keeps up with their regular visits to the doctor to monitor her growth.