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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Summary
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.
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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Summary
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- 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.
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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Summary
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.
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