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Winona and Master Fiendish: Prejudice of Messor by Mustache-Twirler Winona and Master Fiendish: Prejudice of Messor by Mustache-Twirler
I couldn’t help but write a crossover between Master Fiendish and nerdsman567’s character Winona, because of the similar tragic backstories between both characters being outcasts of discrimination and having lost something of great importance, despite having different backstories.

Winona Flat Colors;

Winona Shades;


In the darkness of her deceased mother’s attic, Winona takes refuge. Hesitating to fill her longing to explore the wonders of outside world. Heading her mother’s warnings of the fear the people out there would have over her half-human/half-arachnid anatomy.

Her mother was the only family she knew, and after her mother’s passing, the spiders who lived with her were her only companions. It seemed as though she may never be given the love she once had ever again, yet compared to the existence of certain other individuals, Winona has been living a fortunate life.

On one dark and foggy day, as Winona took care of her fellow spiders in the attic, she suddenly heard faint footsteps from outside her house, gradually becoming louder and louder! She peeks out the window to find a strange, black-haired, overgrown Leprechaun dashing straight towards her house!

Fearful of this potential approaching danger, Winona ducks from the window and quickly hides behind a corner and waits as the front door slams wide open from downstairs! This was then followed by the noises of furniture being pushed against the door as if to barricade it!

The footsteps now tap across the wooden floor as Winona hears the intruder starts mumbling to himself “Where to hide! Where to hide! Where to hide!-Ahah! The basement!” Rushing across the hallway, the sound of a clicking knob and the creaking of the basement door is heard, followed by “Dammit! Too dark to tell if there are any escape windows down there, I’ll be flushed out like a rat!... I’ll have to retreat to the attic!”

The footsteps grow louder and louder as the home invader rushes up the stairs, until the footsteps come to a halt and are replaced by the slight sounds of minor creaks. Winona pushes herself further back behind the corner as to not be spotted, and only takes a slight peak for a closer look as to who’s infesting her home.

As she looks, Winona discovers what appears to be a melodramatic figure wearing a strange green mix between a Victorian and 20s Gangster uniform. His face was round, his eyes were wide yet narrow dynamic and his mustache could almost be mistaken for upside down eyebrows, plus he had a curved and pointed beard. Despite his sinister looking appearance, the man appeared to be terrified out of his whits! Yet it was not because of the spiders, who he was carefully trying to avoid harming, as if he was playing a game of Ballet Limbo, while he tries to reach for one of the windows.

Winona thought to herself. Could someone be after his pot of gold, or his lucky charms, or does he have a phobia of being pinched due to wearing so much green, despite the day not being Saint Patrick’s? The man passes by Winona to look outside and check if he is still being followed. He then pulls from his pocket a small locket, decorated in Nephrite, Jadeite and Emerald. As he opens the locket, a small portrait of what appears to be a humble happy family of his is revealed inside.

Winona could see a trace of melancholy from the person’s face as he stares at the portrait for quite some time, she even started having memories of her mother upon seeing this and felt some sympathy. Certain that he is safe upon double checking from out the window, the man quickly turns around to proceed to find some more heavy furniture, only to stop right in his tracks upon spotting Winona, who was a bit too late to escape from his sight!

The two pause for a brief moment, with Winona fearing the worst of prejudices upon her arachnid appearance... Yet to her surprise, the man’s fears vanished upon seeing her. It wasn’t too long until the man broke the silence as he said “Interesting, I didn’t expect Driders in this universe, let alone co-exist with humans on this planet.”

Winona; “...You’re not afraid of me?”

“No. You seem to be a gentle soul, what’s your name.” Said the mustache-twirler to Winona’s disbelief.

Winona; “My name is Winona...Y-you actually think I’m a gentle soul and not a hideous, ugly monster?”

The stranger simply replied “I have seen so many horrible, hideous, ugly old freaks such as beasts, monsters, abominations and even a living ####ing mockery over all existence... Yet right now, I see none of those.”

He didn’t appear to be lying either, for he showed no signs of fear or disgust towards Winona. “Regardless of having the other half of a creature or not, I just see a timid young woman who wants love and respect.”

A tear ran down Winona’s cheek from her eyes as she heard what this person said.

Winona; “That has to be the kindest thing someone could say to me in a very long time! S...S-Since my mother... I miss her so much!”

Winona wraps her arms around herself being filled with such strong emotions of sadness as she begins to cry. Wanting to cheer her up, the man raised his hand over in a gesture of patting her on the shoulder. When Winona saw him do that however, she let him hug her instead despite being strangers. It took while for Winona to wipe away her tears, before the man asks her “Your mother?”

Winona; “My mother meant everything to me, ever since I was adopted by her. I wish she was still her with me! She kept me safe and warned me about people fearing me. But I never thought that anyone aside from her would be so caring and understanding of me before!... What’s your name?”

He answered “I’m Master Fiendish.”

Winona; “Fiendish!? Who would give such a kind person like you such a dreadful last name?”

Master Fiendish; “...I was named that against my will, and I have an uncontrollable urge to try and live up to that name, despite holding back from committing sin.”

Winona was puzzled by that statement, not understanding why this misnamed “Master Fiendish” actually wants to be like his namesake. Though now she begins to understand why he looks so malevolent on the outside.

Winona; “You want to be a villain?”

Master Fiendish; “I’m addicted to wanting to be one, or more precisely, the ones during the Industrial Revolution that want to kidnap maidens and tie them over railroads as a method of forcing them into marriage for whatever reason, mostly for profit on my part. Yet I’ve tried that method countless times and it never worked for me.”

Winona; “Was it because a big, strong, manly hero showed up and saved them from you?”

Master Fiendish; “No, the damsels kept saving themselves, they took advantage of me caving-in against my plots and traps by sending me on guilt trips. And the only “superhero” I came across was a some random murdering self-righteous psychopath. And then I ended up becoming what they call an “anti-hero” as I ended that idiot’s onslaught by throwing a shot of his own fist to his chops... The guy was a giant, he made gorillas look like gibbons.”

Winona; “That sounds very complicated. But then why are you being so nice to me?”

Master Fiendish; “I feel sympathy for those who’d be wrongfully discriminated... I can relate to that since the only reason I’m in your house is because I need to take refuge... Wait, shouldn’t you be upset that I barged into your home?”

Winona; “Yeah, I usually would be upset having strangers come uninvited, but when I saw your locket, I couldn’t help but relate to you a bit myself. It feels awful missing someone dear to you.”

Master Fiendish; “You mean of the family I could only dream of having?”

Winona; “Only dream of having?”

Master Fiendish opens his locket again and gives Winona a closer look. In the photo was what appeared to be a large family of a father, a mother, bothers and sisters, cousins, aunts, uncles, and grandparents. They each appeared to be portrayed as some sort of villain archetype, ranging from minions to Masterminds. Yet something felt unnatural about the photo for unexplainable reasons and Master Fiendish was missing in there.

Master Fiendish; “One day, if I could find such a family like the one in the locket, I’ll prove to them that I could meet their standards and be accepted with an actual purpose.”

Winona; “What do you mean find such a family like the one in your locket and prove your purpose? What of your actual family?”

Master Fiendish began to regain his fears, fears of what Winona is yet to discover as Fiendish tries to go off topic. For something cold and unnatural ran up his spine, as if he felt the prescience of some unseen threat.

Master Fiendish; “-Do you mind if I barricade the door to this attic?”

Winona; “...Sure, but if you don’t fear me, then what are you afraid of?”

As Fiendish pushes a piano over the attic door, a bright, neon light, flashes from out the window! Simultaneously, an unnatural, low pitched sound of something completely alien erupted, causing Winona’s house to tremble! This was followed by the deep, ominous voice of an elderly imperial goddess, speaking out threats “Whatever pocket of existence you cowardly crawl into, I will flush you out, LIKE A RAT!”

Winona begins to feel an uneasy chill upon the sensation of such an anomaly as she begins to realize Fiendish has a good reason to be afraid.

Master Fiendish; “I’m being targeted for termination from existence!”

Suddenly, the roof of the house begins to separate itself by an invisible force, as if it was being disassembled like a 4-dimensional jigsaw puzzle! Even the spiders and their webs were pushed out of the way as well. All of Master Fiendish’s efforts to fortify the place was rendered useless, for levitating right into the attic, was his executioner!

The very sight of this mysterious being shocked Winona out of her wits. The entity was huge, just from her foot to her knee alone was as tall as Winona herself! She was sharp and jagged all over, from her spiked shoulders to her raptorial talons, all of them blazing an infernal cyan white, contrasting the dark navy blue of the rest of her body. Yet it was her head that disturbed Winona the most, it was shaped like a corrupted yin, with a curved blade at the top back, a long hooked beak like protrusion at the front and jagged shark teeth, and above those were eyes of pure rage! To Winona, it was like looking at a giant anthropomorphic Hemipepsis!

Master Fiendish was even more terrified of this creature than Winona was as he hides behind her spider legs. Yet despite looking like Winona’s worst nightmares, the beast only gave her a brief, neutral, disinterested glance. Yet when the creature turned her attention over to Fiendish, she let out an infuriated glare, followed by the baring of her teeth! She then turned her attention back to Winona and spoke “I apologize for this infiltration into your personal life, yet as Avatar of Messor, the Destroyer Deity of the Yin, I request for you to stand out of the way of my mission.”

Winona was too afraid to respond and began to take a few steps back, yet Fiendish had to speak up.

Master Fiendish; “Look, I know you never wanted me to exist, but it’s not my fault!”

Messor; “I know that, it’s my brother’s fault you exist!”

With invisible powers, Messor lifts Winona in mid-air and, surprisingly, gently positions her a few meters from Fiendish and out of harm’s way. Then, Messor’s hovering descends into a march as she powers up her talons and advances towards Fiendish!

Master Fiendish; “Wait! Hold on for a moment and hear me out! Winona here has a phobia of others potentially hating on her over her appearance! If you complete your mission over your grudge of me for existing, you’re going to send her the wrong message!”

Messor; “If Winona was suffering an unnecessary pain from something she could ask of me to nullify, then I would turn my attention from de-creating you. Yet as long as the drider stays safely out of my path, her pain over the loss of her adoptive mother should not be of my concer!”

Messor suddenly launches her left talons straight for Fiendish, yet her victim quickly dodges the lethal claws!

Messor; “For I will not tamper with her cherished memories of a loved one, no matter how tragic!”

Messor swipes at Fiendish again with her right talons, yet Fiendish evades them with a backflip! Messor’s attacks intensifies as she hurtles her claws even faster at her target, yet Fiendish begins to keep up with the pace as he continues dodging! With each miss of Messor’s attacks, she disassembles anything that belongs to Winona and pushes aside any living creature out of the way of her obsidian sharp cyan-hot blades before reassembling them back again after each retract!

Fiendish then runs across the wall and tries to side step his attacker, and just barely escapes by the skin of his teeth! Just as Messor tries to clamp his face with her beak and even swings the bladed tip of her head at him, Fiendish continues to dodge!

Winona; “How do you know about my mom!?”

With Messor distracted by such questioning, Fiendish quickly retreats back behind Winona.

Messor; “I am an avatar of a deity who is cursed by even higher powers to feel the suffering of others, I know very well of yours. Yet this universe, let alone yourself, are not mine to judge, only that Hellspawn belongs to me! Now out of my way!”

Messor tries to levitate the drider out of the way again, yet this time Winona spun her spider silk onto the floor to anchor herself from being tossed aside again, allowing Fiendish to continue ducking in cover behind her.

Winona; “Why, why do you bare such a grudge with this man!?”

Messor; “Because I never asked for him to be spawned, I never wanted any offspring!”

Winona stares at Messor in disbelief before turning to Master Fiendish.

Winona; “SHE’S YOUR MOTHER!?!?!?”

Master Fiendish; “...Biologically, yes, unfortunately.”

Realizing that Winona will only demand more answers, Messor lowers her weapons and elaborates by letting Winona see directly the memories of Messor.

Messor; “In my domain, my job was to ensure the destruction of whatever is no longer necessary, and to ensure that what is shall be brought fourth from my brother, Provisor.”

As Winona sees through Messor’s mind, she can see Messor as a beautiful woman cleaning the extra-dimensions of the old and decaying, along with an elegant man by her side creating new extra-dimensions.

Messor; “However, our superior put us to the test by making us feel the suffering of everyone we held responsibility over. Provisor failed the test by going insane. He murdered a demon lord named Vice to steal his evil essence in the belief that Sadism and Masochism would cure him. He then ambushed me and ripped out part of my torso, and then along with his, he manifested a ####ing mockery over all existence he calls a Gary-Stu!”

Master Fiendish; “That’s the murdering self-righteous psychopath I mentioned earlier, Winona.”

Messor; “SHUT UP!... Provisor then salvaged the impurities that leaked out of my flesh and then used parts of Vice’s carcass to create the pestilence that is hiding behind you, just to be his torture toy!”

By now Winona had seen everything Messor had told her, the very thought of seeing how Master Fiendish was created by the hands of this cackling abomination, even more hideous than Messor herself, made Winona’s stomach churn in nausea.

Messor; “Yet I am going to stop at nothing to undo everything my failure of a bother had committed! Starting with the easiest atrocity he had made which I can dispatch!”

Messor’s left hand fuses her talons together into a large spearhead, she takes aim right at Fiendish around Winona, and launches her blade straight at her target! Master Fiendish once again dodges the attack and rolls over and managing to unbuckle his cape just in time as a diversion as Messor snatches it with her right talons!

Messor again prepares herself to strike down Master Fiendish again as her quarry ducks back behind Winona! However, despite her otherwise timid nature, Winona had now grown sick of Messor’s cold-hearted discrimination as Messor launches her spearhead yet again!

Just as Messor’s execution blade is passing Winona’s face by the distance of only a few centimeters apart, the drider quickly envelopes Messor’s arm in her spider’s webs! The spearhead just barely touches Master Fiendish’s beard as he backs himself to the wall! As Winona is pushed towards the wall, pulling back the Avatar assassin’s arm and her sharp arachnid legs scraping the wooden floor like cat claws, Messor is shocked and frustrated by such retaliation!

Messor; “I will ask you once more, Winona! Will you please move aside so that I can exterminate the putrid bug you are wasting your time in vain trying to protect!”

And to demonstrate to Winona on what she’ll do when she catches Master Fiendish, Messor uses her destructive powers to disintegrate Fiendish’s cape out of existence! Winona was outraged by this complete apathy from parent to child!

Winona; “You mean murder your own SON!? Never! You have to be the worst excuse for a mother I have ever heard of in my ENTIRE LIFE!!!”

Master Fiendish; “She has a point, mom!”

Further surprised by this opposition, Messor begins to back away, puzzled as to why Fiendish deserves to be protected.

Messor; “Why do you care about Master Fiendish so much!? What has this wannabe VILLAIN parasite done for you that had made you care so much for him!?”

Winona; “Not since my mother has anyone cared about me as much as Master Fiendish has! He doesn’t discriminate, he respects me for who I am, and he has empathy for me! He has a lot more in common with my mother in caring for others than you could possibly be as a mother to him, YOU MONSTER!!!”

Suddenly, a rush of all of Winona’s memories, from her birth, to her time under her mother’s love, to her mother’s passing, and finally to current events with Fiendish’s respect for Winona, flashed before Messor’s eyes as she reads the Drider’s mind! The destroyer deity abruptly became fearful of Winona, not due to fears of her appearance, but because of the risk of unintentionally harming Winona emotionally! This would hold the destroyer Avatar responsible for the Drider’s pain and grief!

Master Fiendish; “It’s over mom! I know you obligate yourself not to harm anyone that wasn’t created by the hands of your brother!”

Messor withdrawals from her assault and gives up the hunt!

Messor; “My mission is a failure!”

Messor ascends above the roof, reassembles Winona’s entire home back to the way it was, and retreats back from where she came. Though this did not cheer up Winona as she is still upset about Messor’s mistreatment towards Fiendish.

Winona; “My mission is a failure”? That’s all your mother has to say for my reasons to protect you!?”

Master Fiendish; “This is what discrimination is like at its peak for me. And trust me, my mom is not the worst family member I have... Speaking of the worst family member I have, I need to leave this universe, now!”

Winona; “Leave? But we only just got acquainted!”

Master Fiendish; “I know, but it has to do with Provisor, her twin brother and my uncle.”

Winona; “What do you mean?”

Master Fiendish; “You remind me of a friend of mine my uncle created as a means to an end for his amusement, just like he did with me. If Messor is the monster, then Provisor is the abomination! I don’t want him finding out about you.”

Winona; “I’m so sorry for all this!”

Master Fiendish; “It’s not your fault. Besides, I actually feel sorry for my mother for what she had to put up with, regardless of what she sees me as. Not to mention I can tell you would not want to take part in my quest to live up to my name.”

As Master Fiendish looks at the family portrait in his locket again and prepares to leave, Winona couldn’t help but give him words of encouragement.

Winona; “I may still not understand why you want to become a villain, but I wish you luck on your journey and I hope you’ll find a true family who’ll love you.”

Master Fiendish; “Thank you, I hope that some day, you’ll meet someone in this universe who will welcome you as a true friend, just like your mom.”

Master Fiendish and Winona hug each other good bye before Winona watches Fiendish set off on his journey across the infinite dimensions once again, in the hope that one day she’ll be able to explore her own world with friends.


Winona belongs to nerdsman567:iconnerdsman567:
Master Fiendish and Messor belong to Mustache-Twirler:iconmustache-twirler:
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Mustache-Twirler Featured By Owner Dec 17, 2018  Hobbyist Digital Artist
Lol! Great reference!
Mustache-Twirler Featured By Owner Aug 27, 2018  Hobbyist Digital Artist
Ah. I also forgot to mention that my first Master Fiendish story is now just a prototype, or “pilot” in a way. I’m still keeping its story, but I decided to reboot Fiendish since The Gary-Stu’s inception after realizing the first story I made had a bit too much in common with Star vs The Forces of Evil. Then again, I’m surprised this crossover story I wrote hasn’t been received comments saying “This reminds me of Cliffside!” Though I found out about that series after I posted this.
Mustache-Twirler Featured By Owner Edited Aug 27, 2018  Hobbyist Digital Artist
I’ve actually been imagining the motion of such with this as well. The avatar of Messor in this cenario has to be one of the weakest I made so far since she has to pay respect to the Universe she is entering, and so that Winona can put up a very effective resistance. And Messor’s devoted respect to even the inanimate makes things extremely difficult for her to destroy her target when someone not on her hit list keeps getting in her way, causing her to loose in frustration over the risk of harming the wrong target. Unlike Provisor who does the exact opposite in another universe and pays the price. And I am so glad to have captured the story in the image as I brainstormed as to how it would look to reflect such. Thank you so much!
Mustache-Twirler Featured By Owner Aug 9, 2018  Hobbyist Digital Artist
Thank you very much!
Mustache-Twirler Featured By Owner Aug 9, 2018  Hobbyist Digital Artist
Which quip? Messor seeing Fiendish as the bug or Fiendish telling Messor that Winona has a point? :XD:
Mustache-Twirler Featured By Owner Aug 9, 2018  Hobbyist Digital Artist
I was thinking it was that one.
Mustache-Twirler Featured By Owner Aug 9, 2018  Hobbyist Digital Artist
Thanks a lot, I needed to put the extra effort in when drawing the gift art. Just having them drawn flat like I usually do wouldn’t do justice for this one.
Mustache-Twirler Featured By Owner Edited Aug 9, 2018  Hobbyist Digital Artist
It was the most action-packed Winona got in the story, as I thought that the idea of a mother treating her child the way pest control treats spiders would cause Winona to aggressively take action against it. I had to learn a lot on perspective at my school and I’m still having to learn more from it. Yet I’m very glad you enjoy the way I drew Winona here since I felt you would enjoy the st.ash images of her alone. 

When I saw a lot of the Winona fanart, I realized that they were generally about her befriending other OCs, explaining to others her personal problems of being feared by arachnophobes, and being given gifts by others. But not a post of her confronting what she fears, plus the only pic of an angry Winona I could find was on your very first drawings of her (the Winona who wants the singing Winona to shut up). So I went for something different with her where she’s standing her ground against a threat. The concept of her facing a typical angry mob with torches and pitchforks sonded dull and boring to me, which was why I decided to have her fight a literal supernatural manifestation of discrimination, prejudice, and intolerance, even if such is not aimed directly towards her in the post.

Thank you so much! I drew this with my index finger in Tayasui Sketches in the iPad Pro. I had gotten rusty on my previous posts using that technique, so I’m glad the practice payed off here. And I am very glad to have surprised you with what I posted for you.
Mustache-Twirler Featured By Owner Aug 9, 2018  Hobbyist Digital Artist
Thank you! I wanted to draw how each character interacts between one onother while at the same time locked in a struggle. Glad you enjoyed it.
Mustache-Twirler Featured By Owner Aug 9, 2018  Hobbyist Digital Artist
Thank you very much! I just had to draw Nerdsman’s Winona, I was happy to do so.
Mustache-Twirler Featured By Owner Aug 11, 2018  Hobbyist Digital Artist
I should have answered this sooner, yet it may take a while for me to draw the post of Randy Tilian let alone write the crossover story because this coming week I’m going to the mountains, but hopefully I’ll be able to draw it.
Mustache-Twirler Featured By Owner Aug 16, 2018  Hobbyist Digital Artist
Ok, I finished the post itself, in the meantime, here is a sample of your gift art;
Randy Tilian and Nicole Honeydive by Mustache-Twirler
Mustache-Twirler Featured By Owner Aug 17, 2018  Hobbyist Digital Artist
Thank you!
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Submitted on
August 9, 2018
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