1 - 20 of 69 Works in Alternate Universe - Pennywise is Defeated in the First Battle (IT)
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It’s a miracle Eddie even has sex with him in the first place, it would be unfair of him to start demanding more. He doesn’t need more. Really, he doesn’t! Richie is completely fine with the whole friends-with-benefits thing they’ve got going on. He’s more than fine with it! He loves it! It’s great! Life has never been better!
At least, that’s what he’s been telling himself these past few months.
But now, he’s standing in a room full of drunk college students, red solo cup scrunched in his fist, pop rock blasting loudly in his ears, and every muscle in his entire body is locked up, frozen in dread - because Eddie is talking to a girl. More specifically, a girl is talking to Eddie. And she has her hand on his arm. And she’s hot. And he’s looking at her tits.
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Richie sees Eddie, his roommate/ bestfriend/ fuckbuddy, getting hit on and fails to react appropriately. Epically. Fails.
Series
- Part 3 of The Intricacies of Masturbation
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oh l’amour (what’s a boy in love supposed to do?) by yoitsjuli
Fandoms: IT - Stephen King, IT (Movies - Muschietti), IT (1990)
12 Dec 2025
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Something in that moment shifted for him, because now all he could think was, I wish you would kiss me.
It wasn’t even really the fact that he was gay that sent him into a full on crisis, it was the fact that it was Richie of all people.
You just had to go and get a crush on your best friend, huh? Nice going, dumbass. Richie, who was loud and obnoxious, who teased him non-stop, who made inappropriate jokes about fucking his mother, who ruffled his hair and kissed his cheek just to annoy him, who called him Eddie Spaghetti.
He fucking liked Richie Tozier.
This was dangerous. Richie was his best friend, and you weren’t supposed to get feelings for your best friend, especially if you’re both boys.
So no one could find out. This was a secret that would live and die with him, even if it meant being slowly eaten away until he withered down to bones.
That was, until Bill and Bev started dating.
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or in which Richie tries to send hints to Eddie, chasing him, while Eddie runs away, convinced there’s no way Richie could like him back. Naturally, this results in an excruciating amount of pining between two best friends who are both too afraid to mess it up.
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Can I Borrow Your Boyfriend? by lezzout
Fandoms: Stranger Things (TV 2016), IT - Stephen King
11 Dec 2025
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"Can I borrow your boyfriend?"
"What the fuck?"
"Will. Your boyfriend. Can I borrow him?"
"Beep beep, Rich. He's not my boyfriend."
"Oh, so I can just go ahead then?"
(Will and Richie fake date to make their crushes jealous)
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It’s just scary, giving up control like that. Letting someone put themself inside you. Even if that someone is your best friend in the whole world. So, logically, Eddie has decided he wants to fuck Richie first.
He figures if he can experience the act from the- enterers- point of view, it’ll be less overwhelming when he’s the- you know- the enteree. Less unfamiliar. He’s not sure he’s even going to like it. Putting his dick in an ass. Yeah, it is Richie’s ass, but it’s still an ass. And, as he’s recently discovered, he likes having his ass played with, not playing with other asses. But still, he wants to try.
And Richie is more than happy to do anything he wants to try.
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Home from college for the summer, friends-with-benefits Richie and Eddie have penetrative sex for the first time. It goes... about as well as can be expected.
Series
- Part 2 of The Intricacies of Masturbation
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The Intricacies of Masturbation by hermeticism
Fandoms: IT - Stephen King, IT (Movies - Muschietti)
11 Nov 2025
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As it turns out, living with Richie actually isn’t half bad. It’s only been one and a half semesters, but Eddie, shockingly enough, still has his sanity intact!
Yeah, Richie keeps him up at night with his nonsensical rambling, and is always stinking up their room with his bong and playing his music too loud, but for the most part - he’s a pretty good roommate.
Honestly, if Eddie’s really thinking about it, he doesn’t have one mention worthy problem with him as a roommate.
Oh yeah. Besides the jerking off.
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Richie and Eddie are college roommates. One is a chronic masturbator, the other can’t even touch his dick. Spending half a year listening to your best friend orgasm himself to sleep every night takes a toll on even the strongest of men... long story short, Eddie is not strong.
Series
- Part 1 of The Intricacies of Masturbation
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Andrew in Drag by brokenpromisesforbrokengirls
Fandoms: IT - Stephen King, IT (Movies - Muschietti)
27 Sep 2025
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“I love you, Richie.”
“I love you too, man.” Richie smiles a toothy smile and it’s like he hadn’t been crying not minutes before, but he’s misread Eddie’s love confession for bromance and that’s probably a sign he shouldn’t repeat it but-
“No, I love you.”
“Yes, I love you too, stupid.”
God’s practically screaming at him to shut his trap and accept his fate but his brain’s in Neverland and he’s letting his heart do the thinking instead of his brain and his heart’s so unfathomably stupid.
“Richie I love you like girlfriend and boyfriend love you.”
Richie gasps on his own saliva. He jerks back from Eddie touch and it’s a huge right hook to Eddie’s ego.
“That’s not fuckin’ funny Eddie.”
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“I'm in love with you.”
“Richie, that's so not funny. Why would you even-”
“I'm not joking. I mean it. I’m in love with you.”
“But. But…you have all those posters on your wall?”
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or Richie and Eddie decide to start datingSeries
- Part 1 of so high school
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i want to be with you (everywhere) by stanshika
Fandoms: IT - Stephen King, IT (Movies - Muschietti)
26 Feb 2025
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God, he missed Richie. They literally hadn’t even been apart for a day, and he missed him. The two of them hadn’t spent a day apart since the summer started, and Eddie hadn’t realized how used to it he’d gotten until now.
He dragged a hand over his face. If Richie knew what he was thinking right now, he’d never let it go. Why the fuck did his best friend have to be such a dumbass?
Eddie was going to have to sneak out to find Richie Tozier.
Or, Eddie realizes he’s in love with Richie Tozier and he’s sick of pretending they haven’t been dancing around it for ages now.
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“What’s going on Bill?” Stan asked as they reached the bumper cars, Bill avoiding looking the other teen in the eyes.
“W-what do you mean?”
“This was your idea, this fairground.” Stan recounted the facts of the day, ignoring how Richie joined the queue for the cars, pulling Bev with him, the pair of them eagerly making bets about who could knock who the most, “But you’ve barely spoken to any of us, and you’ve been stuttering again. What’s going on? And don’t lie to me.”
Series
- Part 1 of Poly Losers
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like brothers on a hotel bed by Thatmalu
Fandoms: IT - Stephen King, IT (Movies - Muschietti), IT (1990)
07 Aug 2024
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Just before high school graduation, Bill and Eddie abandon Derry for a little adventure.
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Richie didn't think in his twenty-eight years of existence to be attending therapy, but here he is. (Thanks Beverly.)
Richie Tozier goes to therapy and navigates through his identity and traumas. It's difficult when it's 2004 and you haven't spoken to your father in ten years. (And you have feelings for your lifelong best friend.)
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taxi cabs and busy streets (that never bring you back to me) by eddiekaspbrakirlsblog
Fandoms: IT - Stephen King, IT (Movies - Muschietti), IT (1990)
08 Mar 2024
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Richie’s career took off not long after he graduated, which Eddie was glad for, the idea of Richie performing in these pretty sketchy bars late at night did not fill him with hope, luckily just over a year in he’d been seen performing at a bar where he was a regular when he’d been seen by someone who had connections in the world of comedy and before long Richie had auditions for Saturday Night Live and there were meetings about him getting his own comedy special on Netflix. Eddie couldn’t be happier for him but this new life came with new things.
OR a long distance reddie au when richie goes on tour for the first time
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“Oh, I’m definitely up for it,” Richie says, raising his eyebrows for emphasis.
“Up for jerking each other off?”
“Yep!”
“Blowjobs?”
“Yes, sir!”
“Anal?”
“Well, you are kind of high-strung-”
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or Richie has an unexpected reaction to listening to the rain, and things get a little messy after thatSeries
- Part 2 of so high school
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How Can You Miss Someone You've Never Met? by the_sun_is_a_deadly_laser
Fandoms: IT - Stephen King, IT (Movies - Muschietti)
09 Feb 2023
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Richie didn't remember his childhood. He rarely thought about it, honestly. But when he did, he didn't mean to. He'd see someone in red running shorts or a colored polo, he felt something he didn't understand:
He felt a longing.
It wasn't sexual or anything. It was... sad. Like he was missing someone terribly. But it didn't make sense, so he tried to ignore it for as long as he could. It wasn't until he was getting sued for property damage, which he didn't do, thank you very much, and Steve, his agent, hired a risk assessor for some weird reason.
As soon as Richie sees him, the longing that he'd ignored for most of his life hit him harder than ever.
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Stanley and Richie have a secret, the love each other un a diferentes way of the other Losers, but in the momentos that they're alone they can show their love without shame.
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In the deadlights, Bev sees the future as it would have been, but seeing the future enables her to change it, and defeat It the first time.
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One person, two identities| Stranger things x IT by yokoneedsmoney
Fandoms: Stranger Things (TV 2016), IT - Stephen King
10 Sep 2022
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Living two identities and lives is already hard it is for Richie but what if people start to discover his secret? That very secret he had hid for years are about to be found.
Or
Richie Tozier/ Mike wheeler are the same person living two lives, shit happens and angst goes kaboom!!
Series
- Part 2 of Stranger things x IT
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Loud Like Love by Thatmalu
Fandoms: IT - Stephen King, IT (Movies - Muschietti), IT (1990)
26 Aug 2022
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Eddie thinks back on all of his previous worries, wishing Richie would have just rejected him and saved him all of this pain. This – what Eddie is feeling now – is far worse than anything he had ever feared.
All he’s been able to do is ruminate over the last seven months. Seven months that began so blissfully. Eddie sometimes wonders if it was all a dream. The visceral agony in his chest is reminding him otherwise. He couldn’t possibly feel this badly had something so wonderful not been taken from him.
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Incident 67-5918 by David_Ginsberg
Fandoms: Stranger Things (TV 2016), IT (Movies - Muschietti)
21 Jun 2022
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The Hawkins National Lab Critical Incident Response Team, informally known as 'The Party,' is tasked with investigating a mysterious set of disappearances in Derry, Maine, but a surprising connection between Special Agent Michael Wheeler and one of Derry's younger residents has the potential to complicate matters.
Series
- Part 2 of Hawkins National Lab
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Summary
college is coming to an end and everyone is going to have to scatter. ben doesn't like the sound of that.
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