[F4ApM] Pennywise/IT long term roleplay

NSFWRP

Hi! I'm going to throw out some prompt ideas that have been on my mind. We can use any of my prompts, combine them or plot something from scratch together.
Anyone I'm already writing with from my previous prompts, I'm not going anywhere. :)
So long as this prompt is up, it's open!

Disclaimer: This will be a dark roleplay. IT is a horror story, so while I'm leaving this open to other genres I still would like to maintain the horror element with Pennywise and my character. Also, my character is 21+.

Scenario ideas in no real order:

  1. Early 1700s, settlers ignored the Wabanaki's warning and ventured into the forest where It dwelt. Hundreds died. One fled deeper, trying desperately to survive. Used to enduring harsh conditions, she utilizes her experience to keep on the move. Trying to find her way out of the forest while her fear is being preyed upon by a hungry, otherworldly being. Maybe she's willing to feed it other settlers for her own survival?
  2. There's a small cult in Derry that has worshiped IT since before the town was built. Little pawns that breed and create new little pawns to grow and continue breathing life into the cult. She moved to Derry, intending to stay a while and learn about its odd history. But one step too close landed her in the hands of the cult just in time for IT to awaken again. (The cult could also just be a new that formed while IT slept.)
  3. A new counselor at the school has been having more and more children coming forward to express they are feeling scared. Those same students are going missing. So in her personal time, she begins to investigate their disappearances. This leads to a game of cat and mouse with the creature known as Pennywise.
  4. IT survived the Loser's Club just barely, dragging itself from the sewers after playing dead. Lucky for IT, it has come across a woman who constantly possesses an undercurrent of fear. IT needs to feed, but her fear and discomfort is useful to regain some strength in order to hunt. Maybe she is just Pennywise's 'home base' for now? Or maybe she is willing to help feed IT?
  5. A combination idea could be the woman from prompt #1 IT took a liking to her for whatever reason. It could use the Deadlights to put her into a stasis state when it sleeps, waking her up when IT does. Or we figure out a reason for IT to preserve her to remain alive and awake in Derry throughout time and be Pennywise's source. Maybe she is the counselor, forced to lure for IT? Or she is the one to save IT from death? Or maybe she is still fighting IT?
  6. Make our own, combine any elements of these, send me your ideas.

I'm open to any time period, combining them into skipping through time or selecting a new time period ourselves.

What I'm interested in exploring:

  • Main themes would be horror and the terror of intimacy. IT and my character would have a very clear understanding of one another. IT, because it can read others. My character, because she pays attention.
  • My character's greatest fear: fear of intimacy. Meaning at some point in her life she grew distant and disconnected from having relationships of any kind. Getting close to people, forming a mutual understanding, acceptance, caring for someone/being cared for, healthy communication, positive touches, all of that and more relates to her fear. This is both physical and psychological.
  • She will be scared in general of Pennywise/IT, but her core fear isn't something IT can shape shift into. Main fear is a long game, everything else (eating people in Derry, terrorizing her in other ways) is just to keep it sated. She sees a monster and so she expects that monster to do monstrous things. But that doesn't scare her as much as intimacy does. A monster's nature makes more sense than the unknowns that come with intimacy and letting someone into her life. How that manifests can range from petrified to defiant.
  • My character has 3 versions of her backstory. They range from very dark to semi-dark in themes but they all contribute equally to her fear of intimacy.
  • A long term roleplay with her being entangled with IT. Whether by force or by choice. Dissecting her fear physically and psychologically, forcing a connection with her to keep building up her fear. Making her feel connected to IT in return, which terrifies her all the more.
  • Preserving a lot of core elements in IT (book or adaptions). Having fun with its inhuman nature! Whether it's the physical shape shifting and other abilities, exploring ITs lore, exploring ITs mentality or a human trying to comprehend IT.

Technical stuff:

I have a pinned post with useful information but I'll speed-run the main things.
30+F. Literate roleplayer, about 20 years of it. Third person preference. Two paragraphs minimum up to novella writing length, but I usually just match my partners. I prefer my partners write at least two paragraphs.
I try to write consistently but real life comes first, so I will have slow days. I make an effort to communicate. I don't care if you take your time, too.
It doesn't matter to me if it's a slow burn or things move fast. I don't care about story to smut ratio, so long as the story and characters are developing.

If anything here interests you, DM me!

Posted Dec 11, 2025, 9:53 AM UTC

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