Caballeron and Derring-Do, known as Daring Do in her critically acclaimed novels, had a strange relationship as time had gone on. Through trials and tribulations of temples, dungeons, and traps, They had known each other as nothing more than nemeses, one chasing after the other in an endless circle for treasure and triumph. Though, as the years went on, the two would get older, face new challenges and find odd feelings within themselves, looking to their pasts along with their futures ahead.

Caballeron, as a young orphaned colt, had been making his way through life the only way he knew how, through odd jobs and stealing little things from vendors here and there. Without a family or nearly a bit to his name, he had found his way into a well known organized crime group know throughout Saddle Arabia. From there Caballeron would steal everything from food for the stallions and mares in the group to jewelry and jewels from the vendors for the group to sell. From there, Caballeron would find a love for those very same jewels and gems he would steal for the group, even going as far to appraise them for the higher ups as to if they were real, fake, well made, or even what price they may go for. Thus, Caballeron would find a love of gems, even getting his cutie mark for it. As time went on, Caballeron was picked up as a star pupil in the eyes of the Crime boss at the time, seeing as he had “great potential” in the eyes of said Crime boss.

As time went on, Caballeron feeling at home with the only family he seemed to have, it was only a matter of time that he would rise in the ranks, making peace or taking down he thought of as a threat within the group, gaining respect of those who had cared for him in the past. As the time of the Crime Boss Caballeron had known as his adoptive father came to an end, Caballeron was put in charge, making sure to continue where his boss had left off. With the crime group now under the lead of Caballeron, he found it to be a bit strange. He had served so long in this group, though he hadn’t truly felt… right in this group. Of course it had served him well as far as survival, and it certainly made him feel welcomed at first. But now?… where was he to lead from here.

That is where a certain golden coated mare would step in. As she saw her home lay to waste as Caballeron’s crime syndicate, she could no longer stand by and watch what she saw idly. So, with her knowledge of adventure by her side, Derring had made her way from her home to the rumored home base of Caballeron to challenge him face to face. Though, it wasn’t as simple as Derring once thought it would be. Once she was ambushed by the members of the gang, she had seemed to meet her match, having finally met the legend, Caballeron. warned to stay away, Derring hadn’t much of a clue what to do. So, once she had mapped out a way to finally stop Caballeron, she made haste. Making her way from temple to temple, taking gems and jewels away from the clutches of Caballeron and putting them safely away in the museum in her home town, ultimately bringing back the life she had once come to know when she was a filly.

Though, with a new rival, the two would face off against each other time and time again. A yin and yang toward each other as they tried to stop each other from succeeding. Caballeron found a new purpose that he hadn’t once seen before. He had someone to face off against time and time again. He felt… comfort in having this stability in his life, and surprisingly, Derring had felt the same towards the gruff Stallion. She hadn’t much realized it until she had put her words to paper, but she would eventually realize her thoughts towards the stallion were intriguing. He had been a gruff, stubborn, and… weirdly suave stallion in their interactions. Despite her hatred towards him at the beginning of their adventures, she found that he had made her life much more interesting, making her ever more interested in what witty thing he would say next in their interactions, only for it to be even more interesting to write down in her books.

Though, they would find that it wasn’t simply as black and white as they both once thought. After being stopped by the mysterious beast, Ahuizotl, they would come to realize that after all these years they hadn’t been simply in a bubble consisting of only themselves, but rather they were interrupting The natural order of which many ancient civilizations of equestria had been built. Civilizations in which the Ahuizotl and other mythic creatures where trusted to protect.

Once realizing their mistakes, in which many of the crime syndicate had not a care for, Caballeron had the hard decision of disbanding the crime unit. Making way for a different kind of life. He had found that same strange solidarity in the mare he had come to hate for so long, now. After an… awkward conversation, the two would find ever more things in common with one another. Turning from once despised enemies into… strange old friends that found the same cheesy mob stories so amazing to read for the hundredth time.

As years went on, it would only take time for the two to become a strange couple for onlookers. They had been the very definition of Enemies to lovers. Very stubborn lovers at that. Though, even with the company of Derring by his side, Caballeron had yearned for more. A family he hadn’t had oh so long ago. Though, despite his wants, how was he to ever get that fabled family? The two had grown so old compared to their younger years. Caballeron having nights where he had wished he had seeked a normal life, only for him to realize he had a normal life in this very moment, cuddling his wife even closer on those nights.

Though, by some miracle, the two would find they had a foal on the way. To the utter delight of the overly emotional buff stallion. He and Derring would welcome a very small, yet very intelligent filly into their lives. With the name Compass Rose to accent that intellect.

Compass Rose would become nothing short of a daddy’s girl. She cared for both her parents, obviously, but where she could talk artifacts and books with her mother, she could find a stallion that was wrapped around her wing in her father. Caballeron would try to spoil Compass Rotten only to be heart struck when she would say “All i need is you Papa! And a journal!” When she was a filly.

Compass is a very simple Mare, Finding comfort in the smaller things in life, like a studying and a good book. She’s one egg carton away from being an egghead. Though, despite her book worm behavior, and her… hesitations towards adventure, she does long for something more, and eventually finds it in the most unlikely of places. She is willing to go above and beyond for her folks and is humbled, and sometimes embarrassed by them. Then again, who isn’t?

Told y’all you weren’t ready.

Aaaaaanyway! Long post aside! I welcome the headcanon of Caballeron and Daring-Do to the stage! Along side the Next Gen of Compass Rose! Prooooobably shouldn’t have fit both a headcanon AND a nextgen in the same post but who needs that 2 hours of description writing back???? me? Nah.

Anyway!! If you got to this point after reading that MONSTER, you’re a beast and deserve all the respect!!! Thank you so much and i’ll most certainly cover Compass and The Do family in the future! Just you wait!