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Ever since Richie matured into his looks, and hit 5’11, he’s become a bit of a slut. It happened during the summer between junior and senior year.
He’d accidentally revealed how he wanted to “suck a dick so fuckin’ bad” one drunken night in the clubhouse, and when none of his friends looked at him in horror or disgust, he thought fuck it - and went out the next weekend in search of a dick to suck.
Richie discovered quite quickly that finding guys to fuck is a lot easier than he thought it would be. All he had to do was drive down to Portland, go in the first gay bar he saw, and within ten minutes there were men practically pilling up on top of him, buying him drinks and begging to take him home with them.
His first experience was… alright. He’d been pretty drunk after downing every single free drink sent his way, and a good looking guy in his late twenties-early thirties started hitting on him. Richie doesn’t really remember what happened in between, but he ended up in the passenger seat of that guys car with his pants around his ankles and his cock down his throat. While his goal had originally been to get a cock in his mouth, he was quite satisfied with putting his cock in some other guys mouth too.
Richie kept that same routine up for the rest of the summer. Every weekend he’d hit the gay bar, fool around with an older man in their car or a motel or sometimes even their house if they didn’t have a wife and kids at home, then be back in bed before the sun rose.
Eventually, though, he started getting tired of the old guys. They were very skilled, don’t get him wrong, but he wanted guys his age, guys he was actually attracted to.
So once school started up again, Richie made a long drive up to UMaine in Orono. He figured there must be at least a couple gay guys on campus willing to fuck. And oh boy, there definitely were.
- March 23rd, 1994
Ben’s mom is out of town for the weekend visiting her sister, so of course everyone invited themselves over to his house to get drunk and spend the night.
Bill and Beverly snuck away to the master bedroom over an hour ago, hand-in-hand and tripping over their own feet on the way up the stairs. Mike and Ben are making a pizza in the kitchen, engaged in a heated discussion about whether Parker Posey or Joey Lauren Adams is hotter in Dazed and Confused. Stanley is passed out on the bathroom floor, his mouth hanging open to let out the ocasional snore.
Meanwhile, Eddie is sitting on the loveseat in the living room, watching A Nightmare On Elm Street on cable and jolting at every jump scare. He’s fairly inebriated, he did take two shots and drank one and a half whole beers, but he’s definitely not as drunk as Richie… who is currently taking what has to be at least his seventh shot of the night.
Eddie watches with amusement, and slight concern, as Richie lets out a loud burp before stumbling over and plopping down next to him.
“Hooooly moly, that’s good stuff,” Richie slurs, draping one arm over the back of the couch and spreading his legs until their thighs press together. His hand finds Eddie’s shoulder and rests on it casually, the other pushing his glasses up with one finger, “what’re we watchin’ again? Oh shit, Johnny Depp in a crop top… Nice.”
Eddie rolls his eyes, scoffing out a chuckle. Ever since Richie came out - well, he didn’t come out so much as just announce that he had sex with a man one day - his sexual comments have gotten a lot more frequent. It doesn’t bother any one of course, they don’t care that Richie’s gay, and he’s always been a pretty lewd guy anyway.
Lately, though, Eddie’s found himself feeling weird whenever Richie jokes about sex or guys, more specifically, having sex with guys. At first, he thought he might be homophobic. But that couldn’t be it, because Bill told him homophobic people hate gay people, and Eddie obviously doesn’t hate Richie. Richie’s his best friend! He loves Richie! So, to say he’s confused about things right now is an understatement.
He hasn’t brought it up to the others, but every time Richie mentions one of his hookups, Eddie gets this strange, tight feeling in his chest. Almost like he’s having an anxiety attack or something. He figures he’s probably just worried Richie’s going to catch some horrible venereal disease and die a painful tragic death, like in that movie about AIDS with Matthew Modine. He does worry about that a lot, if he’s being honest. He gets anxious every time Richie goes to UMaine to meet up with a guy, even though he knows he’s just being stupid, and there’s no reason he should be tossing and turning in bed at night thinking about Richie in some hot college boys dorm room-
“Richie?” he finds himself speaking before he even realizes it, keeping his eyes focused on the tv so he doesn’t accident look at Richie and get nervous.
“Wassaaap.”
“What’s it like to.. you know… do it with a guy?”
“…you wanna find out?”
Eddie swears his heart stops beating for a second. His whole face immediately turns red without his permission, and he’s about to open his mouth to respond when Richie speaks again.
“Hah! Jus’ kidding. But yeah, it’s prettyyyyy great. Well, if you’re into dick. If you’re not then it’d probably be like, super lame.”
“Right,” Eddie responds slowly, his heart pounding rapidly from his brief moment of fluster, “but... I mean, how do you know who, like, does it to who?”
“You mean how d’ya know who takes it up the ass? Great question, Eds. Some guys have a preference, but most are down for anything. You jus’ gotta ask.”
“So, um… do you have one?”
“A preference? Ooooh yeah. I’m a natural born giver, baby,” Richie winks with a lopsided, drunken grin, his hand unconsciously squeezing Eddie’s shoulder, “but hey, if the dudes hot enough, I’ll do anything. And I mean anything. I’m jus’ versatile like that.”
Eddie swallows hard, his fingers fidgeting with the strings of his hoodie. His mouth feels immensely dry all of a sudden. The mental image of Richie in some hot college boys dorm room doing - “anything” - is starting to play on loop in his head. He still has so many questions he wants to ask, but he’s getting that nervous feeling in his stomach again and it’s making him all twitchy. That might just be the alcohol, though.
“Why d’ya ask, spagheds? Been having some gay thoughts lately?”
“No!” Eddie blurts out so quickly it actually makes Richie’s eyebrows raise in surprise, his grin slowly fading into an impish smirk, “I-I mean, no… I’m just… curious, I guess.”
“Uh huh. Just curious.” Richie repeats knowingly, feeling like he’s just been enlightened by God himself. He’s been waiting for this exact moment forever, believe it or not.
He lets his hand squeeze Eddie’s shoulder again, consciously this time, his thumb brushing back and forth along the fabric of his hoodie.
“Well, if you need someone to help you through these strange and confusing feelings you seem to be having, all you gotta do is ask. Like I said, m’down for anything.”
Eddie’s whole body tenses. Does that… mean what he thinks it means? Is Richie… offering to do it with him? No, he can’t be. He’s just drunk and teasing him. Right?
He looks over at Richie hesitantly, and finds himself incredibly grateful the lights are off so he won’t be able to see how red his face surely is. He opens his mouth to respond, but then their eyes meet and he can’t seem to get the words out. Richie’s gaze slowly flits down to his lips, then back up to his big, nervous eyes - and he sees something in them he’s never seen before.
Richie lets his hand move from Eddie’s shoulder to the back of his neck, gripping it ever so gently and turning his head a little. He doesn’t really think about what he’s doing as he starts learning towards him.
“Eds,” he murmurs softly, his face a mere inch from Eddie’s, “you kinda turned me on with all those cute questions about gay sex, so I’m gonna kiss you now. Just hit me or something if you want me to stop.”
Eddie blinks mutely.
Suddenly Richie’s lips are on his, and just like that his brain stops working. His eyes stay wide open, just staring at Richie’s own closed ones in shock. His lips don’t really move, just purse and un-purse awkwardly, but Richie doesn’t seem to mind. Richie just kisses him like- like- well, Eddie doesn’t really have anything to compare it to, considering he’s never been kissed before, but it does feel… nice. He figures Richie must have had a lot of practice, because it seems like he knows what he’s doing.
Eddie gets the tight feeling in his chest at that thought, but it quickly fades when Richie’s hands move to grab his hips and tug him onto his lap. Eddie lets out a tiny gasp into his mouth, his thighs ending up splayed on either side of Richie’s hips and his own hands flying to press against his chest. He pulls back a little and Richie’s lips chase him, crashing their mouths back together in a borderline urgent manner.
Pulling back again, Eddie light slaps at Richie’s cheek to get him to stop, his heart fluttering rapidly and his chest heaving with quick breaths. Richie’s big hands gripping his hips like this have his head dizzy and his mind foggy, barely able to make sense of his own thoughts. He vaguely registers something hard pressing against his thigh.
“Wait, waitwait, Richie.. Richie you’re- you’re really drunk.”
“Not too drunk to fuck you.”
Eddie’s eyes go so wide it’s almost comical - and Richie immediately corrects himself.
“Oops. Sorry. Heh, got too excited,” he clears his throat, one hand slipping up the side of Eddie’s hoodie to rest on the bare skin of his waist, “I meant, not too drunk to… to give you the best head of your life? Is that better or still too gay?”
Eddie just stares down at him in a state of total disbelief, horror, and mortification… and arousal so intense he feels like he might cum in his pants right here and now. Richie, Richie Tozier, is really just- just offering to blow him right now? Like it’s the most casual thing in the world? Eddie doesn’t even know how to react. Or how to respond. Or how to even think, apparently, because the only thing currently running through his mind is ohmygodohmygodhessohotohmygod-
“Eds? Is- did I freak you out? Are you like, totally freaking out right now?” Richie asks sheepishly after a moment of prolonged silence from the boy on his lap, “sorry. Shit, I’m sorry, I’m such a fuckin’ fag. I just, you’re like- I don’t know, you just look really cute right now and I really want to- just- like, hear what you sound like when you cum and I know that’s like so weird and fucked up of me-“
“Richie.”
“Yeah?” Richie looks at him eagerly, his hand still caressing along Eddie’s waist without even realizing.
“…okay.”
“Okay? Okay what? What- okay to what? What does okay mean?”
“Okay to… to- I don’t know, whatever,” Eddie stammers shyly, having to look away from Richie’s intense, lustful gaze to get his words out, “you can… touch me, if you want… or do, you know, whatever… I mean, a-as long as it doesn’t… hurt..”
Richie blinks rapidly, trying to get his severely inebriated brain to clear for a second so he can decipher if Eddie’s being serious or not. This could just be some sexy hallucination his horny drunk mind conjured up, after all. But he feels the weight of Eddie’s body on his lap, he feels Eddie’s soft skin beneath his fingertips, he hears the soft spoken words leaving Eddie’s mouth, and he sees Eddie looking down at him with that cute, shy expression, waiting for him to make a move.
“You really want me to?” Richie forces himself to ask, despite every bone in his body screaming at him to just throw Eddie down right here and now and rip his pants off. He knows Eddie took a few shots earlier. He doesn’t want him to regret this in the morning, that’s the last thing he wants. But… a little voice in the back of his head is telling him this is his only chance. His only opportunity to touch Eddie in all the ways he’s ever wanted to… to hear what noises he makes when he feels good…
Eddie nods, without hesitation this time, his fingers lightly brushing back and forth along Richie’s throat.
“…I wanna know what it feels like.”
Less than two minutes later, Eddie is lying flat on his back in the middle of Ben’s bed. It’s a miracle Richie even managed to carry him upstairs without tumbling down and breaking both their necks. The sheer amount of lust coursing through his body must have given him the strength to make it all the way.
“Wh-what if Ben gets mad we-“
“Don’t care,” Richie murmurs through the sloppy, open mouthed kisses he’s pressing along Eddie’s neck, already pulling his hoodie up. Eddie finds his arms raising on instinct, lifting himself a little to make it easier for Richie to take off.
He watches as Richie hastily shoves his shirt up to his chest, starting to get a little shy from all the attention… and the way Richie looks like a man possessed. No one’s ever touched him like this before. No one’s even seen him naked before! Well, besides his mom and his doctor, but they don’t count. What if Richie thinks he’s too skinny or- or has a weird looking dick or something? What if he does have a weird looking dick?! He knows Richie’s been with tons of guys… guys that are probably way hotter than him and have six pack abs and big dicks and lots of experience-
The unfamiliar feeling of lips wrapping around his left nipple jolts Eddie out of his anxious thoughts, a squeak of surprise escaping his throat and his hands rushing up to grab at Richie’s hair.
“Ah! Ah- Richie that’s- that’s s-sensitive!”
“I know baby,” Richie slurs out in a tone Eddie’s never heard from him before, suckling at one nipple while his thumb and pointer finger gently tweak and roll the other. Eddie whimpers softly at the filthy wet sound paired with the unexpected pet name, his stomach flooding with arousal and his cock growing in his jeans. Richie’s never called him that before. At least, not like that. His back arches on its own as Richie switches, lips latching onto his right nipple now and his fingers delicately playing with the left.
“Fuck, Eds… you sound just how I thought you would,” Richie groans, leaning up to press a quick kiss to Eddie’s lips before moving back to his chest and slowly trailing down his torso. Eddie warms all over, squirming underneath Richie’s hold and accidentally giggling when he kisses his belly button. He hadn’t even realized he was making noises. Is he supposed to make noises? He has no idea. At least it seems like Richie enjoys them.
Richie settles between Eddie’s legs and unbuttons his jeans, his fingers struggling a little with the zipper from how much they’re shaking. It’s only when he grabs the hem and starts to pull that Eddie reaches out and grabs his wrist, looking up at him with the cutest, most nervous expression Richie’s ever seen in his entire life.
“Wait, wait I um- I haven’t showered since this morn-“
“Don’t care. Didn’t ask.”
“But- but should I just go w-wash really qui-“
“Nope. I like my spaghetti au naturel,” Richie teases cheekily as he tugs Eddie’s jeans and underwear down, shimmying them off his legs and throwing them to the floor carelessly. Eddie whines softly with embarrassment, his hands shooting down to cover his achingly hard cock. He doesn’t know why he’s trying to hide it, obviously Richie has to see his dick if he’s going to put it in his mouth, but it feels so weird to have it just out in the open like this. Especially while Richie’s still fully clothed and he’s lying here in just his shirt and socks with all his private bits on display.
Richie only smiles affectionately, gently grasping Eddie’s slender wrists and moving them away.
“You’re so cute,” he murmurs as he looks down between Eddie’s thighs, taking in a deep breath at the sight of his tiny cock twitching with anticipation, “so cute ‘n little just like the rest of you. You shave down here Eds?”
“Shut up! It’s not that little,” Eddie grumbles, Richie’s body preventing him from squishing his thighs together, “and no! I just trim it… it feels dirty when it gets too long.”
“Adorable.”
Richie doesn’t waste another second. He plops down on his stomach between Eddie’s legs and presses slow, wet kisses up his inner thighs, keeping his wrists pinned to the mattress as he does. Eddie can’t help but squirm, his heart rate speeding up the closer Richie gets to his dick. He lets out a needy whine watching Richie kiss everywhere except where he wants it, wiggling his hips a little and flushing at the way his cock swings around.
“Getting impatient?”
“Fuck you! Just- just do it alr- AH!” Eddie gasps at the sudden sensation of a warm, wet mouth engulfing him for the first time, the pleasure so foreign and intense that he tries to jerk away from it, “oh god- ohmygodohmygod, ah! Richie, s-shitRich-AAH!”
Richie has the nerve to chuckle with his mouth full of cock, his hands letting go of Eddie’s wrists to grab onto his hips instead, holding them firmly to the mattress to stop him from wiggling too much. He’s able to take the whole length down his throat with ease, mostly because it’s only about four inches, but also because of all the practice he’s had recently. It feels like all those old man dicks he sucked in the back of a car were just training for this perfect, most important one.
He bobs his head with ease, swirling his tongue and moaning at the simple fact that he has Eddie’s cock in his mouth right now. He can barely believe it. He’s honestly still wondering if this is actually a dream and he’s really just blacked out on the living room floor - then Eddie moans his name so prettily and tugs at his hair so desperately, and just like that he’s brought back to reality.
It’s obvious when Eddie’s about to cum, because his legs start to tremble and he lets out these high pitched gasps and moans and bucks his hips like a little bunny rabbit - so Richie knows exactly when to stop. He pulls off Eddie’s cock with a sinful squelch, and grins at the confused whimper of betrayal he gets in return.
“Waitwai-! nononooo! Wh- Richieee! Why’d you stop?” Eddie whines pitifully, the desperate sound of it enough to make Richie’s cock throb in his sweatpants. His hand immediately reaches for his dick, so close to orgasm that he can’t help but try to touch himself, but Richie’s quick to swat it away.
“Patience, my sweet little virgin. I’m not done with you yet,” Richie says calmly, sitting up on his knees and slowly rubbing his hands up and down Eddie’s quivering thighs to soothe him. Eddie only whines petulantly in response, not used to the sensation of being so close to orgasm and not reaching it.
“But that’s not fair! You- you can’t j-just stop right when- when-“ Eddie stammers out in protest but finds himself too overwhelmed to finish his sentence, his brain all hazy and his body so hot and sensitive. Richie just smiles down at him, so endeared by the shy display. He leans down to press a soft kiss on Eddie’s pouty lips, barely able to restrain himself from saying all the filthy things he’s thinking right now.
“Oh, but I can. And I did,” he murmurs, peppering gentle kisses to Eddie’s cheeks and forehead, “now roll over sweet cheeks.”
“Whyyy?” Eddie whines in delirious confusion, his chest heaving with heavy breaths and his cock pulsing with the need to orgasm. He still doesn’t understand why Richie stopped. He’s never wanted to cum so bad in his life.
“Because I’m telling you to.”
Eddie swallows nervously, his whines getting stuck in his throat at the sudden dominance coming from Richie’s voice. He’s not used to Richie sounding like that. So authoritative. Usually Eddie hates when Richie tells him what to do, but right now it’s making him feel strangely meek.
He lets out a little huff of indignation before turning over onto his stomach and smushing his face in Ben’s pillow dramatically.
“Good boy,” Richie praises with a satisfied smirk, ruffling Eddie’s hair before quickly sliding one arm under his hips and raising them up. Eddie can hardly process what’s happening as Richie shoves a pillow beneath his hips and gently maneuvers his cock out from under him, making it jut downwards for easy access.
But once Eddie realizes the humiliatingly exposed position he’s in, with his ass propped up and his dick hanging down between his thighs, he flushes bright red and instantly tries to get up.
“Woah woah woahhh! Down boy,” Richie cajoles quickly, imitating a cowboy soothing a horse, one hand shooting out to press down on Eddie’s lower back and the other grabbing his balls to make sure he doesn’t move. Eddie reluctantly stops his escape and huffs into the pillow, his fingers clenching in the sheets helplessly.
“Richieee,” he whines, too embarrassed to even lift his head from the pillow, “do I have to stay like this? This is so embarrassing…”
“It’s just me, Eds. No need to be so shy.”
“But… hmph…” his words die on his tongue when he feels Richie grabbing his ass, gently kneading the plump flesh like dough. He wiggles at the touch, his thighs trying to clench together to hide his dick. Richie easily slips a hand between them and spreads them back apart, lightly dragging the pad of his finger down the shaft of Eddie cock and earning a needy whimper.
“Are you gonna… what’re you gonna d- AH!” Eddie squeals in horror at the sudden sensation of a wet tongue on his literal asshole, his whole body jolting in shock, “WHAT THE HELL ARE YOU DOING?!”
Richie tightens his grip on Eddie’s hip, giving his ass a light smack for trying to squirm away again. Eddie squeaks and goes limp, but his cheeks clench together in fear. He’s never even touched his own asshole before outside of cleaning it in the shower, and now Richie’s putting his tongue on it?! It’s disgusting!
“I’m trying to eat your ass, so stop clenching,” Richie says matter of factly, spreading Eddie’s cheeks apart again to get a good look at his cute fluttering hole. Eddie lets out another whine of mortification, feeling so exposed and vulnerable and overwhelmed and… hopelessly turned on.
“N-No! I- That’s- Richie, that’s so gross! Do you even know how unhygienic- I mean- ew! You can’t- y-you’re probably gonna get a disea-!” Eddie’s protests get cut off by a moan as Richie’s tongue dives in again, swiping slowly from his taint up to his hole. He unconsciously arches his back, unsure if he’s trying to get away from the touch or push himself into it. It’s definitely a… strange sensation. He has no idea why Richie would even want to do this. It can’t possibly be enjoyable for him. Who would want to- to eat an ass?!
“Richie- R-Richie wait, that feels so weird,” Eddie whimpers, absolutely mortified by the feeling of his asshole fluttering uncontrollably.
“Good weird though, right?” Richie pauses for clarification, pressing a kiss to his rim as one single finger strokes along Eddie’s leaking cock, teasingly circling the head. Eddie’s toes curl and hips jerk at the faint touch, all these new and unfamiliar sensations overstimulating his inebriated brain.
“I- I-I dunno…” he murmurs shyly, “I feel dirty.”
“Actually, this might be the cleanest ass I’ve ever had the pleasure of eating Eds. Seriously, you’ve got like no hair down here either. I’m honestly impressed.”
Eddie gets suspiciously quiet at the comment. He’d momentarily forgotten how many people Richie’s been with. But now he’s picturing Richie eating some other boys ass and it’s giving him that uncomfortably tight feeling in his chest. He doesn’t really wanna know… but the question comes out anyway.
“…how many have you… eaten?”
“Not important. What’s important is you shutting that anxious little brain of yours off and letting me make you feel good without all this whining and wiggling, capiche?”
“…okay,” Eddie mumbles meekly into the pillow, a certain submissiveness coming over him as Richie squeezes his ass like he owns it. In this moment, it kinda feels like he does.
Richie smiles to himself at the muffled sound of Eddie’s sweet, docile voice. Eddie’s a sassy little brat normally, but Richie always knew he’d turn into a shy submissive mess in bed when faced with the smallest bit of authority. He just had a hunch. It’s the daddy issues… and mommy issues. He presses a sloppy kiss to Eddie’s hole before dragging the flat of his tongue over it, groaning with arousal when it flutters so responsively.
Eddie tries his absolute best to stop wiggling and whining like Richie told him, he really does, but it’s so hard not to when someone’s literally french kissing your asshole and stroking your cock. He grabs Ben’s pillow with both hands and buries his face in it to conceal his whimpers, his hips starting to thrust down into Richie’s fist as his orgasm approaches again.
But just like earlier, right when he feels himself about to tip over the edge - Richie stops. He lets out a whiny cry of frustration, pushing his ass back and kicking his legs so wildly that Richie has to hold his knees down.
“Nono- Richieeee! Why- why do you keep doing that?!” Eddie lifts his head to pout back at him over his shoulder. The needy, throbbing sensation in his belly from having his orgasm withheld for the second time is making his eyes all teary and his mind foggy.
“Awhh, Eds, you’re so adorable… are you gonna cry?” Richie coos teasingly, bringing the tip of his index finger to Eddie’s hole and circling it ever so gently, “it’s okay. You can cry if you need to. I promise it’ll feel sooo good when I finally do let you. You just have to be patient a little longer.”
“I- no! M’not gonna cry,” Eddie mumbles indignantly, wiping at his eyes with the back of his hand, “and- n’ I am being patient! You-You’re jus’ being mean…”
“I’m not being mean baby,” Richie murmurs back softly, the sight of Eddie’s pouty lips and teary eyes giving him pause. He doesn’t want to overwhelm him too badly, this is his first time after all. He slips the pillow out from beneath his hips and carefully maneuvers him onto his back again. He wants to see his pretty face for this next part, “I’m just making you last longer. It’s no fun when you cum in two minutes, is it?”
“…n-no..”
“That’s right. Now, do you want me to keep touching you?”
“…yes.”
“Yes what?”
“…yes please…”
“Good boy. You’re being such a good boy for me, Eds. I knew you would be.”
Eddie huffs at the praise, simultaneously embarrassed and turned on by the way Richie’s talking to him right now. He turns his head to the side when Richie tries to kiss him, grossed out by the thought of those lips just being on his asshole - but Richie just grabs his chin and tilts his head back, kissing him anyway. Eddie gasps into it, his fingers grabbing at Richie’s shirt when he feels something lightly pressing at his hole.
“Ah- R-Richie…” he whimpers nervously, hips twitching away from the potential intruder that is Richie’s index finger, “wait.. is- is it gonna hurt?”
“It’s not gonna hurt, I promise,” Richie reassures completely earnestly, pulling back a bit to look down into Eddie’s wide eyes, “just relax, okay? I’ve got you.”
He reaches over to grab the jar of Vaseline sitting on Ben’s bedside table, hastily popping it open and scooping some out with his index and middle finger. Normally he’d just use spit as lube in his run of the mill, back of the car hookups, but Eddie deserves better than that. Eddie deserves to be treated delicately, gently. Like the precious treasure he is.
Richie brings his fingers back down, lightly rubbing at Eddie’s rim in slow circles, getting it slick and ready for him.
“That’s it… relax for me baby…”
“…are you talking to me or my asshole?”
“Both,” Richie smirks, pressing an affectionate kiss to Eddie’s forehead, “mostly your asshole though. It’s almost as tightly wound as you are.”
“M’not ti- ah! Oh.. oh- ah…” Eddie’s words end in a sharp gasp as Richie’s finger slides inside him for the first time, his hands flying up to grasp at his biceps. It doesn’t hurt like he thought it would, but it’s not exactly a pleasurable feeling either. It’s more of a tight stretching sensation, his ass clenching up around it on its own, as if trying to push it out.
“Don’t clench. Let it in, there you go,” Richie murmurs, his eyes locked on Eddie’s, wanting to remember every expression that crosses his face. He pushes in slowly, pauses, pulls out, then sinks back in again, “Holy shit, Eds… you’re so fucking pretty. Wanted to do this for so long.”
Eddie whimpers, cheeks flushing red at how earnest the words sound coming from Richie’s low voice. He always knew Richie had a soft spot for him, it’s kinda obvious with all the flirtatious teasing and lingering glances and borderline lecherous touching Richie only reserves for him. But that’s all Eddie thought it was, teasing. He didn’t think Richie actually… wanted him.
“..what, finger me?” he tries to say sarcastically, and immediately shivers with embarrassment at how vulnerable he sounds. He can’t believe he’s let Richie reduce him to a flustered, docile mess within the span of twenty minutes.
“Yeah,” Richie grins, kissing him again as he gently moves his finger in and out, “I knew you’d turn into the sweetest little angel for me once I got something up your ass.”
“Sh-Shut up!” Eddie sputters, trying to glare up at him and only managing a small, embarrassed pout, “I- it doesn’t even feel thaaAH! Oh- ohmygodohmygod-!”
The first brush of Richie’s finger against his prostate is so intense it has Eddie’s whole body jolting backwards in shock, his hands racing down to grab Richie’s wrist as a startled moan leaves his lips. He clenches up hard, his thighs squeezing together around Richie’s forearm and his hips tilting away, much too overwhelmed by the pleasure that just shot through him.
“Richie-! Richie wha- ah, wait, that- oh god, that felt- t-too much,” he hurriedly mumbles out, his chest heaving with shallow breaths and his cock twitching where it lies on his belly. Richie has to hold back a chuckle at the adorable reaction, momentarily pausing the movement of his finger.
“Hmm? What’s that? Am I making you feel sooo good you just can’t handle it?” Richie teases with that same cocky grin on his face. It’s taking every ounce of self-control he has not to hold Eddie’s hips down and start finger fucking him so hard he cries. He doesn’t think Eddie would appreciate that very much right now.
“No! I just- I wasn’t expecting it to feel s-so- to be that… intense,” Eddie trails off, seeing Richie’s ego inflate in real time right before his eyes. His grip on his wrist is still tight, almost like he’s scared Richie will just start pounding into him with abandon if he lets go. And it’s not an unreasonable fear.
“Yeah? You think you can take another then?”
“Another what?”
Eddie flinches at the touch of Richie’s middle finger lightly brushing along his stretched rim, his hole fluttering around his index. Oh… another. He wiggles nervously, feeling overwhelmed by just one already, but so fucking desperate for Richie to make him cum that he can barely even think.
“I can make you cum with just the one if it’s too much, so don’t worry,” Richie reassures playfully after the prolonged silence, as if he could read Eddie’s thoughts, letting his index finger slowly slide in and out as he does.
“Um.. I think I- y-yeah, two’s okay,” Eddie finds himself saying without even realizing, his grip on Richie’s wrist remaining, but getting significantly looser.
He bites his lip to stifle a whine when Richie’s middle finger pushes in along the other, the stretch tighter this time.
“Still okay?” Richie asks attentively, keeping his fingers still while he waits for confirmation. Eddie’s a lot tighter than all the other guys he’s fingered in the past, which shouldn’t be a surprise, considering he’s a virgin who’s probably never even fingered himself before. The thought makes Richie’s cock throb. He can’t believe he’s the first person to ever touch Eddie like this, to be inside him, to hear those pretty noises of his… it’s like he won the fucking lottery.
Eddie nods up at him after taking in a shaky breath. His thighs splay back open.
Richie treats him delicately, working his fingers in and out with care, scissoring them apart and wiggling, just gently opening him up. Once Eddie stops clenching and starts taking them without any hint of discomfort, Richie lets the real fun begin.
He adjusts his position, a smirk on his face as his free hand moves down to wrap around Eddie’s cock. At the same time, he lets his fingers drift upwards, firmly rubbing against that wrinkled bundle of nerves deep inside. Eddie moans so loud he’s sure Bill and Bev must’ve heard from down the hall.
“Oh-! oh fuck, Richie, oohmygod!” Eddie whimpers out, his hips frantically bucking up and down all on their own, simultaneously trying to get away from the overpowering sensation and get more of it, “don- don’t stop, don’t stopdon’tstop-!”
“Stop?”
“No! Nono please! Don’t stop, please don- please, pleasepleasedon’tstop-!“ Eddie begs wantonly, grasping Richie’s wrist so tightly now he can barely continue moving his hand.
“Ohh, don’t stop, gotcha,” Richie teases with a grin. His hand is cramping but there’s no way he’s stopping now. Not with the way Eddie’s begging so sweetly. Not with how cute he looks. Gazing up at him at him with big, shocked eyes, letting out these high-pitched gasps and moans, like he just can’t believe Richie’s making him feel this good. He wishes he could take a picture.
“Please- ohpleasepleaseRichie- donstop-!” Eddie practically squeals through his orgasm, shaking and twitching all over from the intensity of having both his cock and prostate stimulated at the same time. His toes curl in his socks, his nails digging into the skin of Richie’s wrist as his cock spurts all over Richie’s hand and his own stomach.
“Nngh.. ah- ah.. R-Richieee…” Richie’s so fucking captivated by the beautiful sight he nearly forgets to stop until Eddie starts whimpering from overstimulation and tilting his hips away, his shaky hands tapping at his arm. He massages for a few seconds more before reluctantly slipping his fingers out of Eddie’s hole, groaning at the way it clenches up from the loss.
“Holy fuck. Holy shit, Eds, that was literally the hottest thing I’ve ever seen in my entire fucking life,” Richie says completely seriously, almost breathing as heavily as Eddie is, “you’re so- oh my god, you look so fucking cute right now.”
Eddie just whines softly, feeling immensely shy and embarrassed all of a sudden. He can’t believe he just begged like that, totally unprompted… and he can’t believe Richie just made him cum that hard. He turns his head to the side and closes his eyes, finding it too hard to look up at Richie’s own blushing face.
“Stop looking at me,” he mumbles into the pillow, feeling Richie’s gaze on him even with his eyes shut. His cock is still pulsing lightly where it rests on his belly, his hole fluttering and sore. Most unappreciated of all, his legs can’t seem to stop trembling.
“Okay,” Richie just grins, pressing a quick kiss to his forehead before hopping up off the bed, “don’t move. I’ll be right back.”
Eddie looks up to see Richie hurrying out of the bedroom in a flash. He pouts in confusion, then hastily pulls a blanket over his half naked body because stupid Richie left the door wide open. Thankfully, though, he reappears only about a minute later with a package of baby wipes.
“Awh, Eds, don’t get all shy on me now,” Richie teases as he locks the door and comes back over to sit on the bed. He peels the blanket back, nearly cooing at the sight of Eddie’s cute soft cock and cum covered tummy. Eddie, still out of it from his orgasm, doesn’t realize what Richie’s doing until he feels a wet wipe gently swiping over his stomach.
“What’re you-! Richieee, stop it,” he whines sheepishly, pulling his knees up to his chest in embarrassment, “you- you don’t have to clean me up… I’m not a baby.”
“No, you’re not a baby. You’re a sweet, innocent little virgin boy who just experienced the joys of a prostate orgasm for the first time and can’t stop shaking, so I’m gonna clean you up,” Richie says without missing a beat, gently pushing Eddie’s legs back down and continuing to wipe the cum off his belly. Eddie opens his mouth to protest, but all that comes out is an indignant huff.
He settles for smushing Ben’s pillow over his face. It somehow feels less embarrassing when he can’t see what’s happening. He can just tell Richie has the biggest, shit eating grin on his face right now.
A muffled squeak sounds from beneath the pillow as Richie delicately picks up Eddie’s soft shaft and swipes the wet wipe over the head of his cock. Eddie instinctively squishes his thighs together, hips pulling away from the oversensitivity.
“Awh. So sensitive,” Richie coos, resisting the urge to tease more as he gently wipes down Eddie’s sticky shaft. Eddie grumbles something unintelligible into the pillow. Probably something bratty, of course. Richie figures he must be back to his normal, sassy self by now. Unfortunately for him.
Richie carefully spreads Eddie’s legs and lifts one to reach his ass, taking a fresh wipe and swiping it down between his cheeks to gather the remaining Vaseline. Eddie feels like he could literally die from embarrassment. If he wasn’t so sleepy and shaky, he definitely would have kicked Richie in the face and ran out of the room by now. He supposes it is… sweet of him, though. Cleaning him up after- what just happened. Oh god, what just happened?!
Richie carelessly tosses the wipes on the floor and recovers Eddie with the blanket before lying down on the bed beside him with a satisfied sigh. He plucks the pillow off Eddie’s face and wraps an arm around his shoulders, pulling him closer to cuddle. He’s a cuddle after sex kind of guy, what can he say? Probably because he’s never gotten to before.
“Now, what do we say?”
“Fuck off,” Eddie grumbles indignantly, but can’t resist snuggling up to Richie’s side and nuzzling his face in his neck. He drapes an arm over Richie’s torso and bunches his fingers in the fabric of his shirt, his heart still pounding and his legs still quivering. He hopes Richie can’t tell.
“Close! Was actually looking for oh my god, Richie, thank you so much for exploring my body so tenderly and giving me the best orgasm of my life, you’re so very talented with your-“
“Sh-Shut up! You better not tell anyone about this…”
“Okay baby. I don’t mind being your dirty little secret.”