This one was originally done for my Darktober in 2024 (I took prompts from goretober, horrortober and kinktober for my prompt list because I wanted more freedom to choose what I wanted to do depending on the day.
I don't think I'm ever not going to be proud of just how far Simon's design has come since I did these initial artworks of him almost 2 years ago now. Most of these were initially on my blog after I finished drawing them, but a few of these have never seen the light of the tumblr dashboard.
Fun fact: Simon only exists because of my friends and I doing a bunch of Yandere VN demo read-throughs together in which we kept making our MC/YN Simp. The original design was just meant to be the visual representation of this delusional little guy who's head over heels for characters who are walking red flags.
He has since evolved into his own little multidimensional chaos gremlin self that has grown into something more than just a one note joke character.
This was my first attempt at a full illustration, and honestly I'm really proud of how this turned out!
[As always, reblogs are encouraged as they help my posts reach more of an audience! Comments are also appreciated, I love having conversations with people in shared fandom spaces!]
A few little doodles of Simon I did back when I was working on updating his design to be more expressive and distinct from James since my art style was very samey around when my big YBG hyperfixation was hitting again.
Another piece I did of Simon that I'm unsure of having ever shared to tumblr, though it definitely saw the light of day on my now defunct Twitter page (fuck Elon Musk and his bullshit pro AI TOS that actively shaft artists)
Warnings for: Blood, Distorted Visuals and potential Eyestrain under the cut.
Summary: Your name is Simon, Simon Vesper and you've lost your mind. You don't know exactly when it happened, but you think back on the events that caused it as you drift through the endless void of the multiverse.
Story under the cut.
As Simon drifted through the boundless expanse of the multiverse, he reflected on the countless lives he had lived and the choices he had made. Each star he touched offered a new story, a fresh canvas for his whims and desires. In some worlds, he was a hero, celebrated and loved; in others, a villain, feared and loathed. The thrill of possibility and endless choices had kept him going for what felt like an eternity.
His favorites, however, were the worlds that introduced him to men who stalked and obsessed over him. It was a dark, twisted game that he played, relishing in the power dynamics and the unpredictability of their madness. These men, with their varying degrees of depravity, became a source of endless fascination to him. At first he feared the unpredictability, resisting their advances and getting himself hurt on multiple occasions. In time he learned he could manipulate, challenge and outwit them, all the while knowing that no matter how dangerous things became that he could reset and start over.
Simon smiled as he floated, recalling each unique and delicate dance of manipulation and desire. His skin tingled with the lines of electricity that washed over him, he reveled in the freedom his unique existence granted him. Unlike the characters in the stories he inhabited, he was untethered by the constraints of their worlds, disconnected from the fabrics of time. Death was but a temporary inconvenience, a reset button that allowed him to explore new possibilities and outcomes.
The endless void of the multiverse was his playground, and he had no intention of leaving it anytime soon. The men he encountered in these worlds became his muses, their obsessions fueling his own dark desires. Each world he visited left a mark on him, a subtle change in his psyche that he both feared and embraced.
As Simon continued to drift, he wondered if there was an end to his journey. Was there a final destination, a world where he would finally find peace? Or was he destined to forever wander, a lost soul in the infinite expanse? The thought both intrigued and terrified him, adding another layer to the complex web of his existence.
For now, Simon was content to float, to explore, to manipulate and be manipulated. The multiverse was vast, and there were still countless worlds left to discover. And as long as there were stories to be told, Simon Love would be there, lost in the endless void, forever searching for the next thrilling chapter.
As he drifted, Simon allowed himself to be lulled into a deep sleep, rest occupied by beautiful paintings of endless possibility. His desires to bend and break the fabrics of reality for his own twisted amusement intertwined with his desire to no longer be alone in an endless expanse. Even in his dreams, the multiverse beckoned, each star whispering promises of new adventures, new obsessions, and new stories waiting to be written.
Maybe someday he could free his loves from the bonds of their stories, bring them together in the stunning chaos of a new story, a new timeline where none of them would be left alone or forgotten. He imagined a world where his most cherished obsessions, the men who had both fascinated and corrupted him, could coexist. In this imagined reality, their combined madness and passion would create a symphony of chaos and desire, a tapestry of intertwined fates that only he could weave.
The thought was both exhilarating and terrifying. To merge the fragments of his fractured experiences into a cohesive whole would be the ultimate act of creation and destruction. It would be a challenge unlike any other, a new game with higher stakes and greater rewards. Simon's heart raced at the prospect, his mind already concocting scenarios and plotting outcomes.
For now, though, Simon floated in the serene void, his dreams filled with visions of what could be. The stars whispered their secrets, and he listened, ever eager for the next story, the next obsession, the next love to captivate his wandering soul. In the vast expanse of the multiverse, Simon Love drifted on, forever searching, forever dreaming, and forever lost in the endless possibilities.
