Area: Entrance
Year: 1944

Scootaloo, Jonathan, and Charlotte return to the castle and go to talk to Wind/Eric Lecarde and Rainbow Dash. "Goodness Scoots, what happened to the artifical wings?!" RD asked out of the blue.

"Ugh, thanks for reminding me of my situation..." Scootaloo said in annoyence as she looked towards Wind, "Wind, I need to ask... does the name 'Loretta' ring any bells?" she asked getting Wind's undevided attention.

"Yes, she was my daughter along side her sister Stella... why do you ask?" Wind asked in a state of confusion.

"She's a vampire and thinks this 'Brauner' person is her father." Scootaloo explained which did cause Wind's eyes to go wide.

"I... I knew my daughters were here but..." Wind started saying in concern.

"Squirt, how the hell did you know that?"

"After me, Jonathan, and Charlotte beat Dullahan, who could for some reason transform into a unicorn, we met Loretta and she basically said 'Fuck you, you only weakened us a bit as my father has more of these sons of bitches' more or less."

"Sums it up well," Jonthan said slightly annoyed at being reminded, "Especially since I couldn't use the whip on her... well, I can't use it anyways but I meant that I couldn't use it at this weak ass state on her."

"The whip itself stopped you, a Morris can only use the full power of the Vampire Killer through the help of a member of the Lecarde family but even that has a cost. A Morris using the whip loses part of their soul, your Father, my friend, John Morris, didn't teach you to use the whip because he wanted you to learn to not rely on it," Wind explained.

"Told you he probably had a good reason, Jonathan, since I'm pretty sure you like having a soul," Scootaloo said.

"Seems that Eric knows a lot about that whip... wait a moment... did John know of the consquences before using the whip?" RD asked, eager to learn which was odd for Scootaloo as Rainbow usually doesn't. Wind shook his head however.

"No, the only reason we knew this information was because after we beat Elizabeth Bartley, we used magic in the hospital to look at John's inner health," Wind explained.

"I noticed something interesting I didn't notice before, if both of you are ghosts then how are you not on the castle's side?" Charlotte asked.

"Twilight magically boosted me before I came here."

"I used magic to bind myself to the castle and cast a barrier on this room to defend from the castle, including mentally," Wind explained making Rainbow look like a fool.

"Regardless, we have paintings to find and monsters to defeat," Scootaloo explained as she left the room to explore more of the castle, leaving Jonathan, Charlotte, Eric, and RD alone.

Jonathan and Charlotte went to catch up with Scootaloo to find that she got stuck in front of a boss door again, "Curse this damn castle and curse it reminding me of Castlemania," she said in clear distain. Jonathan and Charlotte both realized that they now have to open the door with Scootaloo or themselves. What Scootaloo failed to notice was that she had an entrance at the lower level as when Jonathan and Charlotte opened the door they were immediately pulled in, leaving Scootaloo outside the boss door.

"... well shit."

Scootaloo heard stomping below her, she went down and found the Behemoth stomping back into the arena and Scootaloo followed it with a dash attack which dealt massive damage to the Behemoth. "Did Brauner expect me to be locked out? Laughable, very laughable," Scootaloo mentioned as she tossed a vial of holy water down using the last of her hearts, "Ugh, shit. I'm out of hearts now."

The Behemoth opened his mouth and several fleshy tendrils flew from it's mouth in an effort to attack Charlotte who just back dashed to avoid it while Joanthan attacked with his leather whip. Scootaloo grabbed Fatal Wind and used one last dash attack causing the beast to screech in pain as it fell down and died. "Was I the only one expecting that to be harder?" Jonathan asked as both Scootaloo and Charlotte nodded.

Moving forward, Scootaloo realized just how much faster she was growing compared to her first adventure, at about the same point in her first adventure, she was still consistently having death memories and now? They aren't even really needing to save to be safe. That goes to show how experienced she was and fast she was growing.

Scootaloo found a wall that she could break and entered, finding very little to worry about. "Did you find anything?" Charlotte asked but Scootaloo just shook her head.
The group continued going downwards until they found a doorway that seemed... different in nature to the other area doorways encountered until now.

"This is door is enchanted with both Chaos' magic and Equestrian magic... why? I've felt no Equestrian magic until now so... why is this door the first case of Equestrian magic in this castle?" Scootaloo asked as she trotted through the door.

Area: Buried Chamber
Year: 1944

Scootaloo looked around the Buried Chamber before turning to Jonathan and Charlotte who were now ponies. Specifically, Jonathan was a red pegasus and Charlotte was a blue unicorn, "Woah, this is weird, how do you feel Charlotte?" Jonathan asked turning towards Charlotte, revealing his Cutie Mark to be a whip and sword overlapping to form a cross shape.

"I'd probably be better if: 1) there was an explanation for this and 2) I knew why I was a filly," Charlotte said, letting Scootaloo get a look at her Cutie Mark, which was a book with a pentagram on the cover.

"I can give you an explanation alright... the door was enchanted with a special transformation magic to transform humans like you into ponies so you can better fit in, which should
even stay true if you use a transfomative spell and then undo that."

"Soooo... we're ponies in this section with the same abilities as the ponies of your world, am I getting that right?"

"... yes. In laymans terms, yes."

"Doesn't explain why I'm the size of a filly."

"Guess the transformative magic saw you for who you are, a filly." Scootaloo said as she trotted forward...before realizing that Jonathan and Charlotte faceplanted in their lack of knowledge of how to walk... this was already a bad start.

Half an hour later...

Scootaloo had taken the time to slowly, and it was a very slow process, teach Charlotte and Jonathan how to trot/walk. Finally.

Now they could finally start going forward. Going forward, the group encounter spinning platforms that really didn't seem to like them on it. And it wasn't long before they saw why this area's entrance was enchanted. A deep purple unicorn who was known by many as the Silent Night and was suspected of being Silent Void's daughter or granddaughter due to how little she spoke, and this time was no different. Silent Night said nothing as she trotted forward.

"She's creepy... who even is that?"

"Silent Night, a pony the Princesses and the ponies of Ponyville had kept an eye on. She doesn't speak much causing her to be suspected to be related to the infamous Silent Void but other than that no evidence linking her to the dark minions Sweetie Belle's amassing,"

"Uuuuhhh... okay, so she might be a threat but we're not sure, got it."

Exploring the Buried Chamber didn't do much but allow them to find a door out of the strange area and into...

Area: Great Stairway
Year: 1944

Entering the new area had Jonathan and Charlotte back in their human forms and finding both the repaired Artifical Wings but also another cube which was the Stone of Flight. Scootaloo found she could just double jump with her wings currently as she'd have to work back up to full flight.

Not long after they entered the area, they find Death in a room alone. "So you three have arrived," he said, correcting his pin.

"Death! So you've allied yourself with Brauner then!" Jonathan said aloud but Death shook his head.

"No, I'm waiting for the opportunity to deal with Brauner so I can open the way for my master to return, I will say that I underestimated how long you'd survive, Scootaloo."

"Heh, goes to show you shouldn't get in over your head if you know what's good for you and messing with me and my belongings is a sign of someone getting in over their head."

"But then what is your plan? If you wish to defeat Brauner, you must have a plan to do so." Charlotte told Death.

"You'll find out... hahahahaha..." Death's laughter continued as he vanished.

"Let's find a place to recuperate before we continue exploring, just to be safe, you know?" Scootaloo said as Charlotte and Jonthan nodded and they went to a nearby save room.

Author's Note

Bosses beaten: Behemoth

Relics Acquired: Artifical Wings(Allows Scootaloo to Multi jump), Stone of Flight(Allows Jonathan and Charlotte to double jump)

Shorter chapter, what is going on with the Portrait Arc. Simple. The previous arcs, due to the fact that there isn't a "time limit" in the story since Castlevania and Caslemania make the surrounding area have enternal night, I was like "Let's do the action" but for Portrait I figured I'd focus a bit more on character development since, at least I feel so, it seems the earlier arcs were super lacking in them, sure there was character development, but it doesn't feel right to me, ya know.

Maybe I'm rambling to hide the actuality of me being lazy... tell me what you think of the more "Character-Relationshop" focused stuff versus the "Battle" focused ones since the battles are pretty much cakewalks anyways.

Also, tip, the side quests Wind gives are technically canon for this but... not all of them. The only canon ones are the ones that give new skills and weapons(Exclusively Whips and Tomes) while RD has some extra stuff for Scootaloo to do that only gives her higher max stats.