Work Text:
There was something weighing on Eddie’s mind. It had been on his mind for about a month, but the action in question that sparked the thoughts happened almost twice as long ago. Two, probably three, months ago Eddie couldn’t shake Bill off his shoulder. All the losers were pretty close, but it was obvious Bill was just trying to break off a piece. They all kind of did that, being in their early twenties and all. Eddie hadn’t done much in the bedroom, and he was nervous around new people. At first he didn’t care to hook up with Bill, but he kept flirting and would ask again every so often. Eventually Eddie relented, and he even went as far as to do more than he’s ever done before.
Eddie wasn’t exactly a virgin, but he wasn’t riding wild and free either. He was still pretty innocent, but not innocent enough to be completely clueless. “Fooling around” is what he would describe his level of experience until he hooked up with Bill. He’s given and received oral before, and he’s had handjobs exchanged with dates before. His main reluctance to actually have penetrative sex stemmed from feeling insecure and worried. Anal sex was rather messy from what he’s heard, and he didn’t want to be so vulnerable with a total stranger. It wasn’t like he was hooking up all the time so he felt no need to rush into it. Hooking up with Bill was almost comfortable. He explained to Eddie how to douche himself in the shower, and was very sweet about it. By the end of it, Eddie didn’t cum by penetration at all, but he was kind of glad he got that over with. Everything felt so stiff and uncomfortable, and he was almost waiting for Bill to just finish already so he could properly jerk off.
At the time he figured he just wasn’t into bottoming, and he went on without a second thought. He didn’t think about it again until a month later when he accidentally let it slip to Richie, his best friend and roommate, that he slept with Bill. Needless to say, Richie wasn’t exactly thrilled to hear that. He wasn’t rude about it, but Eddie could tell he didn’t like that information being hidden from him. In all honesty, Eddie didn’t like hiding things from Richie either. They’ve been through thick and thin together, and they both kind of had a similar attitude about keeping secrets from each other. So Eddie was upfront about it, and how it was just a one time hook up and how they’ve never tried anything like that ever since. Richie merely nodded a little bit and focused on whatever he was doing in the meantime.
What really triggered Eddie’s thoughts about his hook up with Bill was how much he realized he didn’t like it. It wasn’t like it was horrible, but Eddie couldn’t help but feel a little bit unsatisfied. He loved his friends more than anything, and Bill definitely made him feel safe during the whole thing. Still, he just couldn’t shake this feeling that he didn’t really get the full experience. It made him wonder what really good sex felt like, and if he could plausibly hook up with someone who could actually make him feel good and comfortable. He’s never put anything inside himself before or after that incident, but he was tempted to. Even though he knew, from what he remembered, that he didn’t like it. He was still curious if there was a way to make it feel good.
“Don’t think too hard. Your face will get stuck like that looking as funny as it does,” Richie said walking past Eddie to open the fridge. He snapped himself from his thoughts and continued stirring his tea.
“Sorry,” he sighed and pulled out the tea bag.
“No worries. What’s on your mind Eddie spaghetti?” Richie teased pulling out the milk.
“Nothing. Just…thinking,” he murmured and added his honey.
“Fair enough. Humans do that sometime,” Richie nodded and uncapped the milk to take a swig. Eddie once told him to buy his own jug of milk if he was going to continue doing that, and he immediately left to get some when Eddie said that. “But what are you thinking about?” Richie asked after wiping his mouth. Eddie shrugged and then stirred in his honey.
“Nothing important…just thinking about something that happened a while ago,” he admitted.
“Oh yeah? What’s up?” Richie asked. Eddie sighed and then turned to lean against the counter and face Richie. His roommate was leaning against the fridge taking another sip of milk.
“Just…thinking about that hook up I had with Bill forever ago. It’s so weird, I can’t stop thinking about it,” he murmured shyly. Richie’s demeanor seemed to drop, and he crossed his free arm over his chest.
“Yeah? What about it?” He asked looking down at the milk.
“Nothing special. I guess…I dunno. It didn’t really go the way I thought it would. I’ve never done anything like that before, so…I guess I’m just wondering why I feel so unsatisfied about it,” Eddie explained as best as he could. He really couldn’t deliver his thoughts very well with how long ago it was.
“Unsatisfied? Like how?” Richie asked.
“I dunno. I was thinking about asking Bev since I know they kinda dated in high school. I’m just wondering if sex is always like that,” Eddie said.
“Like what?” Richie questioned. Eddie blushed.
“Bad? I guess? I dunno. Something felt off,” he replied. It was barely there, but Eddie swore he caught Richie rolling his eyes.
“I mean, you slept with Bill of all people. He doesn’t have the best reputation in bed,” Richie pointed out. He took another swig and then opened the fridge to put the milk away.
“He doesn’t? I didn’t know that. All I know was that he was flirting with me and I trust him because he’s my friend. What do you mean he has a bad reputation?” Eddie asked. Richie shrugged, and then moved his hand in a weird slithering back and forth gesture.
“Directionally challenged,” he said and then closed the fridge. Eddie frowned.
“Directionally challenged? Wait, are you talking about like…when he’s moving his hips?”
“Look, Eds, if you’re really having a headache over this, you should go ask Bill. Y’know, since you trust him so much?” Richie said a little bluntly. It was now obvious that he was at least a little bit upset about something. He left Eddie in the kitchen with his jaw wide open, but Eddie stubbornly followed Richie to the living room.
“What’s that supposed to mean? What are you so butthurt over?” Eddie challenged. Richie huffed as he flopped down on the couch, and then looked over at Eddie with his arms crossed and his hip popped in a sassy stance.
“I’m not butthurt, okay? I’m just saying if you’re bothered about it you can always ask Bill what happened,” Richie replied.
“But if he’s just bad in bed he won’t know what happened. Didn’t you say he was directionally challenged or whatever? Do you honestly think he’d be able to take that and try to fix it. Even if he did, I have no clue what it means either, so I can’t help him with that,” Eddie argued. Richie sighed and stressfully ran his fingers through his hair.
“Geez, well what do you want me to do about it, Eds? Show you what good sex is supposed to feel like?” Richie questioned. Eddie blushed, but he wasn’t opposed. It was the same logic. Richie was his friend, his best friend actually. If he had his pick, Richie would’ve been the one he shared his first time with. Bill was just annoying and Eddie happened to be curious.
“I dunno. Maybe? Would you be willing to do that?” He replied. Richie blinked at him once and then furrowed his brows in confusion.
“What? Are you asking me to fuck you?” He asked. Eddie’s blush got even worse.
“I—No, I was just…isn’t that what you were offering? I just…y-you said—“
“Okay, chill before you have an aneurysm,” Richie interrupted. Eddie groaned in frustration and ran his fingers through his hair. Why was this so infuriation to talk about?
“Why do you say that like it’s a big deal? We all hook up all the time! I’m pretty sure we’ve all had sex with each other in one way or another! Bill sticks his dick in everything, and Mike has Stan wrapped around his finger. Bevvy and Ben are all over each other and shit. Like, why do you say it like it’s weird I’m insinuating that?” Eddie ranted. Richie laughed at that, and Eddie found himself completely lost.
“Eds, just…wow, it’s okay, alright? I was just surprised, okay? I wasn’t expecting innocent little Eddie spaghetti to ask me something so bold,” he said. Eddie’s blush had calmed down, but he was still flushed with embarrassment. He put his hands on his hips.
“I’m not as innocent anymore, okay? Just because I’m not hooking up all the time doesn’t mean I’m still a baby,” he pointed out. Richie chuckled.
“And yet you’re asking me to fuck you so you can tell what was so bad about last time? It was your first time too, right?” Richie pointed out. Eddie rolled his eyes and then moved to sit next to him on the couch.
“Maybe. Whatever. Forget I asked,” he grumbled.
“Aw, don’t be so grumpy. If you wanted a ride on the Tozier express you could’ve just said so, sweetheart. Although fair, warning. He’s like a bullet train. He’ll get you there fast, baby,” Richie said with a wink. Eddie looked at him with wide eyes.
“Wait, you’d do it?” He asked. Richie’s faced melted again for a moment, and he looked almost pained that Eddie took his joke seriously.
“I…look, I’m gonna have to think about it, okay? I just…like, we live together y’know? It’s one thing when you shack up with Bill because you don’t have to be around him all the time. You probably would’ve realized how bad it was sooner if you lived with him, and it would’ve been really awkward.”
“Do you think you’ll be bad?” Eddie questioned.
“That’s not what I’m saying.”
“Then what are you saying?” Eddie pushed. Richie sighed and rubbed his eyes.
“I’m saying we should think this through before doing something like that. Sex is fun, but it can make things complicated really quick,” Richie pointed out.
“But we’re best friends, Richie,” Eddie pointed out. Richie was silent to that point, and Eddie decided to pull out his ultimate weapon against him. His puppy dog eyes. “Rich…”
The subtle whine in Eddie’s voice captured Richie’s attention enough for him to turn his head. He almost whipped it away when he noticed this big round eyes, but he kept looking against his better judgement. Eddie blinked and pushed a little pout on his lips as he continued to look up at Richie and tilt his head ever so slightly. He touched Richie’s arm, and focused on trying to make his features look as soft as possible.
“Yeah?” Richie replied.
“Could you please show me how it’s done? I have no idea what went wrong,” he requested with Richie’s full attention on him. He shut his eyes in response, and turned his head to cover his mouth with his fist.
“Goddammit, Eds…” he sighed.
“I’ll do everything you ask, okay? I’ll make sure to be good for you too,” Eddie promised.
“Christ, Eds. Shut up before I pop a stuffy,” Richie grumbled. Eddie went as far as to nuzzle against Richie’s shoulder, and that was enough to capture his attention again.
“Please…” Eddie begged again after their eyes met again. Richie sighed and ran his fingers through Eddie’s hair.
“Why don’t you get ready for me then, okay? Go ahead and shower and get cleaned up. I’ll meet you in my room,” Richie said softly. Eddie’s eyes lit up with pride, and he nodded.
“Okay. I’ll be right back,” he said. Richie smiled and then kissed the tip of Eddie’s nose.
“Okay.”
Luckily, Eddie didn’t have much to clean out since they had woken up relatively recently. It was totally a coincidence that they both had the day off, and honestly it wasn’t a bad way to spend it. Richie was always the untouchable friend in the group to Eddie. Sure, he’s made his way around with a few of them just like the rest of the group, but for some reason Eddie felt like he was off limits. Well, less off limits and more like in his dreams. Richie was just so cool all the time. He was an absolute idiot, but he had a cool attitude to him. When they were kids he was always getting them in trouble and dragging Eddie into his dangerous games. It always stressed Eddie out, but he secretly wished he could be as brave as Richie. After a while he realized he also wished Richie would take him on other dangerous adventures of their own.
Since the last time Eddie ate was last night, he decided to use the plastic water bottle trick that Bill told him about. It was the first time he was executing it, but Bill gave him more than thorough details and instructions. Once he was all clean he found himself getting nervous like he did with Bill. The only difference was that he did actually care if Richie liked what they were doing. He wanted to please Richie, and he wanted him to feel good. It would be nice if he liked what he saw too, but Eddie didn’t want to push his luck and get his feelings involved. That’s why Richie was hesitant in the first place anyways. Regardless, he wanted Richie to have a good time so he wasn’t just putting in the work for Eddie’s own selfishness.
He honestly debated getting dressed again. A part of him was thinking it wasn’t worth it since they both knew what they were going to do, but another part of him couldn’t help but feel like it would be rude to just waltz in butt naked. So he decided to pull on a pair of shorts and a teeshirt, but otherwise went commando for the sake of ease. He trusted the pair of shorts he was wearing too, so he felt comfortable walking up to Richie’s open door and leaning against the door frame. Richie was busy checking the dates of his lube and his condoms, and then finally looked up when Eddie shyly knocked on the frame.
“Can I come in?” He requested.
Richie looked him up and down and then nodded when their eyes met. Eddie blushed and then closed the door behind him after he stepped in. Richie set the supplies onto the nightstand and crossed his arms as Eddie crawled onto the bed. Their height difference was already pretty substantial, but with Richie standing to the side of the bed and Eddie sitting on it everything felt even more tilted. He had to have his neck at a weird angle to look up at Richie, and the look he gave in return made Eddie feel a little be guilty for some reason.
“Alright. So, where exactly do you think he went wrong?” Richie asked. Eddie felt less like he was getting ready to be dicked down and more like he was being scolded by his principal.
“I mean…I dunno. I guess…all of it? He had been asking me every so often for a couple weeks, and I guess the only thing I liked about it was the fact that he’s my friend and that he was into me,” Eddie said. Richie nodded.
“Okay. That’s pretty much true in this context too, so there should be no problem with that,” Richie said. Eddie blinked up at him with owlish eyes, and Richie frowned. “Did I…assume wrong?” He asked. Eddie’s brows shot up and he shook his head.
“No! Sorry, I just…I didn’t realize you were…into me,” Eddie admitted shyly. Richie smirked at that.
“Of course I’m into you. Are you kidding me?” He scoffed. It was the first relief of tension since Eddie had walked in, and he couldn’t be more grateful for it.
“Okay…then yeah. I have no problem there,” Eddie agreed. Richie nodded.
“Great. So…how did you guys start?” He moved on. Eddie felt a little disappointment. He thought Richie would be doing more /doing/ then talking.
“Well…we were kissing for a while…and then we were grinding and shit…and then…we got naked. After that it really started to go down hill because no matter how long he was fingering me I couldn’t really relax. I…actually kinda lied and said I was ready when I really don’t think I was,” Eddie told him.
“Well, lucky for you I can actually tell when you’re lying,” Richie said as he stepped closer to the bed. “And I won’t move on until I’m absolutely certain you’re ready for it,” he continued. Eddie nodded obediently, and felt eager as Richie sat next to him finally.
“How can you tell?” Eddie asked. Richie smirked and touched his knee.
“Trust me. It’s pretty easy to tell,” he hummed. He then reached up to touch Eddie’s cheek instead, and looked at his lips. “How was the kissing?”
“It was…okay…” Eddie murmured. He was looking at Richie’s mouth as well, and wanted nothing more but for their lips to meet. He smirked.
“It’s okay. You can be honest,” Richie assured him.
“It…wasn’t that good,” he admitted. They both chuckled, and Richie came closer as they both settled.
“Yeah…Bill isn’t very talented with his mouth either,” Richie said.
“Are you?” Eddie asked. Richie grinned and looked him in the eyes again.
“They don’t call me trashmouth for nothing, baby,” he cooed. Eddie smiled at that.
“Then kiss me,” he tempted. Richie chuckled and then leaned forward.
Ever since Eddie understood what kissing was, he wanted to do it with Richie. He was always so tempted to ask him if he’s ever kissed someone when they were kids. His fantasy’s were almost exclusively lip locking with his best friend in the hammock they had in their clubhouse. Hours wasted just thinking about the texture of Richie’s lips, how sloppy he would be, and how inevitably sugary sweet he would be too. Because Richie really did have a sweet side to him, and in Eddie’s experience it showed the most when he was being affectionate. He happened to be rather affectionate a lot with Eddie already.
When their lips met for the first time, it was sweeter then Eddie could’ve imagined. It was the perfect amount of pressure and the perfect amount of warmth, and when he tilted their heads to fit better he didn’t feel overwhelmed by the wetness between their mouths. Instead he only wanted more, and when Richie pulled back he wanted to just crash back in. They stayed parted for a moment, but Richie looked like he wanted to say something in that moment. What ever it was he wanted to say was long forgotten by the time Eddie lost his patience and leaned back in for another kiss. Richie reciprocated, and let his lips work some more as he moved his hand from Eddie’s cheek down to his waist. The heat from his hand on his body felt amazing and Eddie instantly wanted more.
Doing this with Bill didn’t get Eddie as excited. When he spent the night with Bill they had to make out for nearly an hour before he felt this desperate for more. Richie didn’t even need a full minute to make Eddie want more from him. He reached for the hair on Richie’s nape, and gently curled his fingers into the soft strands as he purposefully kissed him harder. Richie hummed in approval, and then pulled Eddie closer by his hip. Butterflies erupted in his tummy from Richie moving his body so easily, and he weakly rested his hands on Richie’s chest. His shoulders were always so broad. Eddie has wanted to touch and feel them since they were in high school and Richie started to fit his body.
“Mmh…how’s that?” Richie murmured between their kisses. Eddie nodded and didn’t bother to remove his lips except to kiss Richie deeper. Unfortunately that only made the other man pull back completely as he waited for a verbal answer.
“‘T’s good…really good. I like it,” Eddie answered obediently. He’s never wanted to please someone so badly before, but Richie made his body feel so wiggly and hot. He couldn’t help but hope Richie felt the same way.
“That’s good. Are you turned on yet?” Richie asked with a flirtatious smile. Eddie couldn’t help but giggle and nod. He wasn’t used to being so transparent and physical with Richie, but he definitely liked it.
“A little bit…” Eddie murmured
“Yeah? Just from a couple kisses?” Richie teased. Eddie blushed and Richie seemed to enjoy that.
“You’re a good kisser. I’m sure you’ve already been told that,” Eddie said. Richie chuckled and pecked him on the lips.
“A couple times, yeah. It’s all about who you’re kissing though,” Richie replied.
“I guess you’re just really good at kissing me then,” Eddie whispered as their mouths stayed close from the little kiss Richie gave him.
“Yeah? Better than Bill?” Richie asked as he slid his hand down Eddie’s leg. He nodded in response and kissed Richie again out of desperation from how close they were. His friend indulged him, but eventually pulled away again to tilt his chin up and look up at him.
“Say it,” he demanded softly. Eddie blinked.
“You’re so much better than Bill, Richie,” he obeyed. Richie smirked and then granted him more kisses.
Eddie has had his fair share of kisses before, but there was something about kissing Richie that felt extraordinary. Maybe it was because of his hopeless childhood crush, or maybe it was because Richie was legitimately very good at it. Whatever it was, it made Eddie feel like jello and he only wanted more of it. He took a moment to gather himself before being bold. His hands spread across Richie’s chest before he settled them on his shoulders, and then he stood on his knees to crawl into Richie’s lap. The other man shifted his legs to accommodate, and guided Eddie on top of him with his hands all over his body. Each touch felt amazing, and Eddie just wanted Richie to rip his clothes off and touch him to his own desires. It was obvious Richie was into this too, and as their mouths reconnected it was even more obvious.
Heat kindled between them while Eddie got settled. He sat perfectly on Richie’s lap with his knees straddling his hips. Large hands drifted up his shirt, and Eddie wanted to cry out for the fingers touching the softest parts of his body. They eventually made their way up to Eddie’s nipples, and he moaned softly as Richie gently brushed his thumbs over them. Bill never bothered to experiment with this area, but Eddie knew from self exploration that they were a little sensitive. He tried to stay focused on the kissing, but lost his concentration when Richie circled his thumbs around the rose budded flesh. Then he gently pinched the peaks between his thumbs and his knuckles, and Eddie couldn’t do much with his mouth except whine and breath heavy.
“You like that, sweetheart?” Richie cooed. He continued rolling his nipples between his knuckles and thumbs, and Eddie nodded. His hips moved involuntarily as Richie pinched them a little harder, and he pouted for more. “Say it.”
“I like it…I like it a lot. Please, Richie. I want more,” Eddie requested.
Richie smirked and kissed him on the lips one more time. He removed his hands from where Eddie wanted them, but Eddie was appeased when they reached to pull up his shirt instead. Richie pulled up the fabric, and Eddie lifted his arms to let him fully remove it. As his shirt was tossed to the side, Richie ducked down to kiss over his neck and chest. His warm lips leading down his skin felt wonderful, and as they wrapped around his nipple he couldn’t help but gasp. He occupied Eddie’s other nipple with his hand, but focused mostly on the one in his mouth. Warm, wet sensations drove Eddie crazy, and he immediately gripped the hair at Richie’s nape as he licked and sucked on the pebbled skin. He moaned as he watched Richie’s mouth, and let his eyes close as his brows pinched in pleasure. Eventually he switched sides, and Eddie couldn’t stop his chest from heaving as Richie repeated with his mouth and flicked his other nipple easier with it wet from all his spit.
“Ahh…fuck, that feels so good,” Eddie murmured. His hips moved to their own accord again, and Richie used his free hand to encouraged that movement. Eddie’s head hung back at how good it all felt, and he whimpered as Richie lead kisses up his neck again.
“I didn’t realize you were so sensitive here, baby,” Richie hummed as both hands continued on Eddie’s chest. He huffed, but tried to keep his noises down. In all honesty he didn’t expect himself to be so responsive. He knew he was sensitive there, but Richie just made his whole body on edge from how badly he wanted him.
“Mmh…you’re just good at this,” Eddie decided. Richie chuckled, and Eddie wanted to melt in his lap.
“Yeah? Did Billy not do it how you like it?” Richie asked. Eddie shook his head.
“He—he didn’t even…he didn’t even touch me like this,” Eddie stammered as Richie sucked on his neck. He really shouldn’t have any hickeys because of his job, but he couldn’t help but want a dozen from Richie.
“What a shame. You’re so cute like this,” Richie teased. Eddie moaned impatiently.
“Richie, please. Touch me more,” he begged. Richie kissed him on the lips and returned his hands to his hips instead.
“Where do you want me to touch you, Eds?” He asked. Eddie rocked his hips again, and guided Richie’s hands down over his ass.
“I want you to touch me how you want to touch me,” Eddie whispered. Richie bit his lip before fully grabbing Eddie’s ass like he was prompted to. His hands dug into the soft flesh, and Eddie felt extra sexy remembering that he didn’t put on any underwear.
“Yeah? Is that what you what? You want me to touch you however I like?” Richie questioned. Eddie nodded with hazy eyes, and then gasped as Richie pulled him closer by his ass. “Is that how you want it?”
“Yes! Please,” Eddie nodded. Richie kissed him hard on the lips, and Eddie couldn’t help but whimper into his mouth in response. His hands grabbed and groped Eddie’s ass, and as they pushed up his shorts they seemed to be searching for something. Richie pulled back with furrowed brows when he couldn’t find what he was looking for, and then hooked his chin over Eddie’s shoulder to look down at where he was touching.
“Babe, where is your underwear?” He asked.
“I-I didn’t see a reason to put any on since…we’d be doing this,” Eddie said truthfully. Richie seemed to pause for a moment, and then lifted the elastic to Eddie’s shorts to see nothing but skin.
“Christ,” Richie sighed.
“Is that…is that okay?” Eddie asked shyly. Richie let go of the elastic and grabbed his cheeks again. That triggered a little sound Eddie didn’t mean to let go of, and he nuzzled Richie’s neck as he felt him up.
“That’s more than okay, baby. Fuck, you’re so sexy,” Richie murmured close to his ear. Eddie shivered hearing that, and then arched his back into Richie’s touch.
“Mm…I want you so bad, Richie,” Eddie confessed. Richie pulled a hand away to lick his fingers, and then reached down to pull his shorts out of the way. Wet fingers rubbed against Eddie’s clean hole, and he gasped at the contact.
“Yeah? Is this where you want me? You want my cock right here?” Richie continued. Eddie nodded and clung to Richie as he touched him to his own desire. “Say it,” he demanded.
“I want it! I want your cock inside of me so bad,” Eddie obliged.
Richie kissed the side of his face, and then pulled everything away to lay him down. He let Richie take off his shorts, and then gasped as he twisted his hips until Eddie was face down on the sheets. He grabbed at the blanket under him, but nothing could prepare himself for how good it would feel when Richie dragged his tongue up from his bridge over his hole. The entire sweep made him shiver from how hot his mouth was, and his jaw dropped as Richie relentlessly lapped at him and pulled his cheeks apart.
“Oh my god! Richie! Oh fuck!“ He whined. Richie kissed and sucked around his hole before returning and then pushing his tongue inside it.
The first time Bill pushed his finger inside of Eddie’s hole he wanted to turn his body inside out. Thankfully he was sufficiently lubed up, so it didn’t burn, but he was much too tense for it. With Richie he felt like he was already loose, but only just enough for it not to hurt. It was still a stretch, but an enjoyable one. Extremely enjoyable, and absolutely deliciously warm and melting hot. His entire body felt lit up from Richie’s touch, and his mouth was merciless as he spit on his hole and licked it up. Eddie moaned at that, so Richie spit on him again, and pushed his tongue back inside. The extra spit made it slide in so much easier, and it made Eddie’s toes curl in a good way this time. He fucked him a couple times with it before completely pulling off. Eddie twisted to look over his shoulder, and felt even hotter watching Richie slowly drop another wad of spit over his hole. The wetness met his skin, and he moaned in approval before Richie could lap it up again.
“Fuck…fuck, oh my god,” Eddie panted. Richie replaced his mouth with his thumb, and gently rocked it through the puddle of spit between Eddie’s cheeks.
“Yeah? You like that, baby?” Richie asked keeping his free hand on Eddie’s waist. He nodded.
“Yes! Of fucking course I do,” he heaved. Richie chuckled and then gently eased his thumb inside. Eddie whined, and loved the stiffness of Richie’s thumb compared to his soft tongue.
“Did Bill treat you this good?” He cooed, pushing as far as he could until the rest of his hand stopped him from going further. Eddie shook his head.
“No…no, he didn’t…mmh…he didn’t use his mouth like that,” Eddie confessed. Richie laughed, and it almost sounded bitter.
“Figures. It feels so good though, huh sweetheart?”
“Mhh…so good…fuck, Richie,” he mewled as Richie started moving his thumb in and out. He spit again to keep it smooth, but eventually just pulled out so he could grab the lube.
“I’m gonna finger you now. Is that okay, Eds?” Richie said. Eddie nodded and then moved to his side. He twisted his upper half to face his friend, and let Richie hold his legs to the side as he spread the warmed up lube between his cheeks. He shivered despite its warmth, and hummed in appreciation. Bill didn’t bother to warm up the product for him, so going in it was rather chilly. Richie took his time to warm it between his fingers and then tease and prepare his hole for another finger.
“How many do you want? One or two?” Richie asked. Eddie blinked up at him and then moved his top leg to make it easier.
“Two please,” he requested.
Richie bit his lip and then did as he was asked. He pushed in his middle and his ring finger, and made sure to rock them back and forth to keep it smooth. Eddie’s brows pinched at how good it felt, and let Richie lean over his legs and kiss him on the lips as he got used to the stretch. He let go of the sheets to touch Richie’s shoulders again, and was disappointment to meet fabric instead of skin. Instead of using his words, he clawed at the material over his back. It was hard to even think about speaking when Richie was making him feel so good.
The stretch was so warm and comfortable compared to the way Bill prepared him, and Richie just had an extra affectionate touch to him that made his heart feel full. He got Richie’s teeshirt bunched up under his armpits, and was happy when Richie leaned back to completely remove it. His fingers were gentle when they pulled out, and even more careful pushing back in. Eddie’s eyes instantly went to Richie’s newly revealed chest, and he didn’t hesitate to touch the endless amount of skin now at his disposal. He was distracted when Richie slowed the speed of his fingers, and then looked up to give the other man the attention he was so subtly asking for.
“How’s that, baby?” Richie cooed. Eddie huffed and returned to his ogling.
“Good…I can take another,” he answered. Richie hummed and leaned in to kiss him again. Eddie accepted it gratefully, and touched his naked chest for the first time.
“Yeah? You think you’re ready for it?” He questioned when they parted. Eddie nodded and pressed more kisses to Richie’s jaw and neck. “Say it.”
“Please, Richie. Please gimme another,” Eddie requested. Richie kissed the side of his head, and then eased in a third finger. Eddie’s brows pinched, and he whimpered into Richie’s neck as he nuzzled closer to him. There was more friction, and he was feeling less loose at the new heat rising between them. His arms fully wrapped around his neck, and Richie seemed to enjoy that.
“I gotcha. It’ll get easier as it goes, okay?” Richie assured him. He pulled back to grab the lube again. Eddie was reluctant to let him go, be decided the extra lube would be worth it. Richie pulled his fingers out so only the first knuckle was still inside, and then added a dollop of lube to his fingers. He pushed them back in a little quicker then before, and Eddie shouted from the speed. He let his head fall back, and his chest heaved as he craved more.
“Was that good, baby? Should I do it that fast again?” He asked.
Eddie nodded, and wanted to cry as Richie slowly pulled out to repeat the action. His body felt like it was being teased when Richie established a pace that was slow to retract and fast to shove back in. Those long fingers felt so good coming out, and so intense when they came crashing back. It was so drawn out and long to leave his body that it almost lost the memory of how nice it felt to be so full. Then it was such a rush when it came charging back in. Eddie was starting to doubt he even actually had sex with Bill last time because Bill never made him feel like this.
“Is that good enough for you, sweetheart? God, you’re so fucking precious. You sound so sexy when you moan like that,” Richie rambled and then kissed up his neck. Eddie moaned with each thrust, and then moaned extra loud when Richie talked about how much he liked that.
“Richie…oh fuck,” Eddie sighed. Richie started to speed up his thrusts, and Eddie could feel his guts winding up like a clock. The faster he finger fucked him, the tighter his insides felt. It was amazing, and Eddie had only been able to feel a build up like that from pleasuring himself.
“Yeah? You like it when I fuck you with my fingers like that? You like it when I make you feel good?” Richie hummed and continued kissing up and down his neck. Eddie nodded and whimpered as his fingers suddenly started to curl inside him. The heat inside him nearly erupted, but he wasn’t quite close to cumming yet. Although, the new little curl to his fingers definitely brought him closer to close. “Say it,” Richie demanded.
“Hahh! Yes! Yes, I really like it. I really like it, Richie. It feels so good. I’ve never felt so good before. Fuck,” Eddie whined. Richie rewarded him with a kiss on the lips, and then introduced their tongues as he continued the addicting friction from his fingers.
“Mm…do you think you’re ready for me soon, sweetheart?” Richie asked. Eddie nodded and reached up to touch his chest once more.
“Yes…yes, and I really feel ready this time. I wanna feel you inside me,” he whispered. Richie groaned and kissed him again.
“Anything you want, baby. I’m all yours,” Richie murmured sweetly. Eddie smiled at that and pressed their lips together as lovingly and as sweetly as he could.
“I want you now…please, I want more,” Eddie requested.
Richie nodded and pulled back to get started on his jeans. He had to wipe the lube off on the covers, and Eddie couldn’t help but wrinkle his nose in disgust to that. Thankfully he was distracted when Richie got up to jump out of and kick off his jeans. That made Eddie giggle as he sat up, and Richie smiled back at him before pulling down his boxers. It was probably rude, but Eddie couldn’t help but look directly at Richie’s dick. For one it was rock hard and hard to ignore, and for two it was probably the only part of Richie’s body Eddie hadn’t seen. He’s even seen his butt more then his penis, and he was quickly realized he had been underestimating just how big a big penis was. His eyes went wide at it, and he curled his legs closer in response to it. Richie chuckled, and that thankfully distracted him as he looked up at his best friend crawling back onto the bed.
“Cat got your tongue?” He asked touching Eddie’s legs again. He let Richie pull them out, and then shook his head.
“No. Sorry, I just…I didn’t think you’d be so…big,” he replied. Richie smirked and then moved Eddie’s legs some more to position him.
“I’ll go easy on you, okay? It’ll be easier if you’re on your tummy,” Richie suggested. Eddie nodded, and then moved with his strong hands.
Once he was situated, he was completely face down again with one leg completely straight and the other one hitched up to open his cheeks a little easier. He felt so vulnerable in that position, but with Richie’s warm hands running up and down his thighs he felt good. Especially when his touch wandered up to Eddie’s ass. His fingers sunk so easily into his flesh, and his palms covered him so easily it was like they were made for each other. He pinched Eddie’s cheeks a little to tease him, but Eddie only found himself liking it and enjoying the attention Richie was paying to his body. Everything that went wrong with Bill was becoming more and more apparent, and Eddie was so grateful to have Richie show him how good it can actually feel.
“I’m gonna put the condom on, okay? I’ll be right back,” Richie told him.
Eddie nodded, and then turned his head on his side to blink up at Richie as he got off the bed again to stand in front of his nightstand again. It was nice to take a breather. Everything had felt so intense, and he while he was eager for more it felt good to catch his breath. Richie rolled on the latex with ease, and then spread a generous amount of lube over his hard dick. He used much more lube then Bill did, but he also had a much bigger cock as well. It was strange how Eddie’s body craved Richie more when he was objectively twice as big as Bill. When Bill was inside him it felt like a knife in his stomach. Logically he couldn’t help but worry a little bit about how bad it would hurt since Richie was bigger, but his fears were soon smoothed away when he felt Richie rock his dick between his cheeks.
“You’re thinking too hard again,” Richie murmured. Eddie nodded in agreement. “What are you thinking about?”
“Just…just, how much it hurt with Bill. You’re…so much bigger than him. I’m kind of scared,” Eddie admitted. Richie rubbed his lower back in an attempt to comfort him, and it worked pretty well.
“That’s okay, sweetheart. I don’t think Bill took the time to actually warm you up, okay? I made sure you’re nice and loose before I asked if you were ready. If it hurts at all we can stop,” Richie assured him. Eddie nodded immediately, and trusted Richie’s words much more than Bill’s.
“Okay…okay, I’m ready,” he allowed. Richie leaned down to kiss him on the neck, and then lead up to Eddie’s mouth before speaking.
“I gotcha, baby,” he cooed. Eddie nodded again, and then curled his fingers into the sheets as Richie leaned back to rock his hips again. His slick cock rubbed directly on his hole, and the warmth and hardness felt so good against him. Eddie subtly pushed his ass out to show just how ready he was, and he bit his lip in anticipation.
“I’m gonna push in now. Is that okay?” He asked.
“Yeah…” Eddie answered.
Pressure bloomed against Eddie’s hole, and at first it felt really good. Then the head of Richie’s cock finally pushed past his tight ring of muscle, and it was suddenly very overwhelming. Eddie gasped at the initial push, and grabbed the sheets again but tighter. It took him a moment to get used to the stretch, and Richie helped by rubbing and massaging around his hole with his thumb. That definitely felt good, and he eventually relaxed into the sheets before he pushed in even further. The way Richie slid into him was smooth but tight. It definitely felt more good then bad, but the sheer size of him was definitely a lot to swallow down and get used to. Still, Eddie only wanted more, and whined with every inch Richie pushed in.
“How you doing? Think you can handle all of me, babe?” Richie asked. Eddie nodded despite his shivering body, and then moaned in encouragement. “Say it. Say you can take all of my cock, baby,” Richie prompted. Eddie struggled to find his tongue as Richie pushed in even more. Surely he was more than half way by now, right?
“I…I can take it. I can you it, Richie. I can take all of your cock,” Eddie rambled while arching his back even more to show his dedication. Richie groaned above him, and Eddie was happy to hear Richie enjoying himself too.
“How badly do you want it?” Richie asked next. He pushed in some more, and Eddie’s chest started to heave. The heavy fullness inside of him felt so good and comforting, and he didn’t understand how Richie felt so good while Bill felt like the biggest thing he’s ever taken. Richie was definitely big and overwhelming, but he felt so good.
“So bad…want you so bad,” Eddie confessed shyly. Richie’s thumb continued at his hole, and he then pushed the last little bit before they were completely flushed with each other. When he bottomed out Eddie was expecting for it to finally hurt, but he was definitely mistaken and instead couldn’t stop whimpering over how good it felt.
“Fuck, you’re so tight…so fucking warm,” Richie huffed. He bent over to kiss Eddie’s shoulders, and Eddie felt his body melting from the accidental pressure and friction Richie provided from moving his body.
“Mm…please…Richie, please…god, just fuck me. Please,” he begged. Richie chuckled against his nape, and then kissed under his ear.
“Yeah? You want me to fuck you?” He asked. Eddie nodded desperately. “Say it.”
“I want you to fuck me, Richie. I want you to fuck me so good,” Eddie obeyed.
Richie kissed down his spine, and then gently started moving his hips. He pulled out slower than he pushed in, much like when he was fingering Eddie, and that made Eddie go absolutely crazy. Bill only fucked him in missionary since he said it would probably be the most comfortable, but this just felt purely good. There was no weird numb spot when Richie pulled out, and there was no pinch when he pushed back in. He fit inside him so perfectly, and there wasn’t an inch of Eddie’s body that didn’t feel good in consequence of it. He panted heavily as Richie got started, and then gasped for breath as he started to speed up. Strong hands gripped his hips, and Eddie loved the feeling of Richie’s hands so firm on his body. It filled him with so much warmth, and he was already tempted to ask him for more.
“Christ, Eddie. It’s like you were made to take my cock, huh?” Richie murmured while he fucked him. Eddie nodded in agreement, and moaned with each quiet little slap of their hips. Richie then started to speed up again, and Eddie couldn’t help but bury his face in the sheets from how good it felt.
“Richie…Richie, oh my god…” he gasped.
“Yeah…yeah, did Bill fuck you like this, baby? Did he ever make you feel this good?” Richie asked. Eddie opened his mouth to answer, but cried out instead as Richie suddenly hammered his hips into him. The speed made everything so much hotter, and his grip got even tighter on Eddie’s hips as he fucked him harder.
“Fuck! N—no, he…he didn’t,” Eddie answered as best he could.
“Did he ever fuck you like this? Huh? Fast and hard? He ever make you take it? Fucked you so good you couldn’t think? Can Billy do this for you, baby?” Richie went on.
Eddie felt overwhelmed by the questions, and just wanted to shout about how good Richie felt inside him. He paused to pull up Eddie’s hips, and within minutes Eddie found himself ass up and face down. Before he could say something about it, Richie was pushing his cock back inside him and Eddie was crying out. The angle was so much more intense with his legs closer to his chest, and he could only really blubber into the sheets as Richie continued his harsh pace from before. From how loud their skin slapped against each other from each thrust Eddie felt like it should’ve hurt, but instead he felt mindless from the fire and the pressure building inside him.
“Answer me, baby. Did Bill ever give you dick this good? Did he do this when you guys hooked up? Did he fuck you so hard you were shaking like you are now?” Richie asked in a stern voice. It was shaky from the sex, but it was still deep and so so hot. Eddie shook his head. “Say it,” he demanded harshly. Eddie cried out and lifted his head to speak clearly.
“No! No, he never! Never fucked me this good! Never!” Eddie sobbed.
“Is that it, baby? He’s just not as good as me? You think anyone else could fuck you this good?” Richie pressed. Eddie shook his head and shoved his hips back against Richie’s thrusts. He got so much deeper like that, and Eddie felt himself drool as he moaned. “Say it,” he repeated.
“Mmh! N-no one! No one can fuck me as good as you, Richie! You fuck me so good! Your dick is so fucking good,” Eddie gasped and shouted.
“Say all of it. Tell me how Bill can’t make you feel as good as I can,” Richie cooed.
He slowed down his hips for him to say it, and Eddie needed a moment to catch his breath as Richie languidly rolled his hips into him. His impatience must’ve gotten the best of him, because before Eddie could even try to say something he was being pushed onto his back again. Richie had to pull out again to get him spun around, and Eddie let him crawl over him and pin his legs up so he was folded in half with his lower back lifted off the mattress. He took Eddie’s chin in his hand and tilted his head to look at him, and Eddie nearly fell in love with the wild hazy look in his eyes. Thankfully Richie spoke before he could pathetically confess his love, and he couldn’t be more turned on by what he said.
“Say. It. Now,” Richie hummed. Eddie hiccuped, and then nodded.
“Bill could never…h-he could never…he’s just not good at fucking me like you are. Bill did nothing compared to you. He‘s nothing,” Eddie replied.
Richie bit his lip, and then let go of his chin to guide his cock back inside of him. Eddie moaned at the push again, and happily welcomed the more steady pace. Their lips crashed together as Richie fucked him in their slightly complicated position. It was the closest to how Bill had Eddie before, and it was so much better with Richie holding him up and kissing him so desperately. His lips soft and sweet, yet so desperate and demanding at the same time. He cupped Eddie’s face and caressed his cheek, and that reminded Eddie of his own hands. So he reached up to wrap them around Richie’s neck, and held him closer as they slowly dissolved into a puddle of pleasure and warmth.
“Richie…mmh…so good…feels so good…” Eddie whimpered between kisses. Richie kissed him deeper, and then nuzzled against his neck as he drove his hips a little bit faster again.
“Fuck…oh my god, Eds…so hot and wet…you’re still so tight, feels so fucking good, baby,” Richie murmured. Eddie moaned mostly from his words, but also from the pace he was constantly reestablishing. It got him so close every time, and when he changed it he was building that pressure again from scratch. It made him more desperate to cum, and he was almost sick of not getting close enough.
“Richie…Rich, can I be on top next?” Eddie requested. Richie’s hips stuttered, and he quickly pulled out to grip the base of his cock. Eddie pouted at the emptiness, but noticed he did it because he was much closer to cumming than Eddie realized.
“Fuck…holy shit…” Richie huffed.
“Please? Bill said it wouldn’t feel good because it was too deep, but I really want that with you,” Eddie pleaded.
“Fucking Christ, Eds. God, that’s the hottest fucking thing I’ve ever heard,” he wheezed. Eddie giggled and then kissed the side of his head.
“C’mon. Let me on top, please,” he whispered sweetly.
Richie nodded and then slowly sat back to let Eddie down. They switched positions, and Eddie enjoyed the feeling of smiling down at Richie. He first indulged in a kiss on the lips, and then backed up to get in position. Richie helped hold his cock for Eddie to sit on, and then guided it inside him as Eddie lowered himself. At first it was fine, but as he got to the bottom again it felt much different. It reached much deeper inside him, and his entire body wanted to curl with satisfaction. This is what he wanted. This is what Bill couldn’t give him. His head fell back from the intensity, and he was very quick to start rocking his hips and grinding down to reach even further.
“Fuck, Eddie, your body is fucking beautiful,” Richie huffed. Eddie lifted his head back up and blinked down to see Richie’s eyes stuck on the way he moved his hips against his cock.
“Mmmhh…you…you think so?” Eddie asked shyly. Richie bit his lip and nodded before holding his hips and feeling them move instead of guiding them.
“Of course, baby. You’re the sexiest thing I’ve ever fucking seen before,” he cooed. Eddie blushed and leaned a little bit over on Richie’s stomach for better control of his grinding.
“Have you…have you always thought that?” He asked. Richie nodded instantly.
“Fuck yes. Especially when you were in track and you had those shorts. You still wear shorts like that all the time. God, I’ve wanted you for fucking ages,” Richie confessed. Eddie blushed.
“Y—you have?” He stuttered. Richie nodded and squeezed his hips to feel the softness of his skin.
“Of fucking course I have. I’ve wanted to fuck you the most out of the whole group. I only hooked up with anyone else because I though you weren’t interested,” Richie confessed. Eddie’s hips had slowly came to a stop, and he had to take a moment to collect his breath as he stayed still. Richie blinked up at him, and before he could ask what was going on Eddie spoke.
“Richie, I have like the biggest most pathetic crush on you,” he confessed. Richie’s eyes went wide, and Eddie gasped as he sat up and kissed him hard on the lips. “Richie! Mmh…”
“Fuck, are you serious? This isn’t a joke, is it?” Richie asked.
“No? Why would I joke about that?” Eddie asked while trying to get used to the new angle Richie made.
“I dunno. Whatever, that’s not important. You really like me?” Richie asked. Eddie nodded.
“I thought you didn’t want to sleep with me…so I didn’t want to bother you and ask,” Eddie said. Richie scoffed at that and then kissed him again.
“Baby, I want everything that you want. I want you so bad,” he promised. Eddie hummed with approval and pleasure, and held Richie’s face as their lips continued against each other.
“I want you…mh…I want you, Richie…” Eddie said.
Richie nodded, and grabbed his hips so they could grind against each other. Eddie mewled in response, and Richie accepted every hot moan against his lips with a kiss. Eventually he had Eddie on his back again, and Eddie was grateful that they could kiss a lot better in this position. He wanted to kiss Richie forever, but the pressure was building so quickly and his lungs were too busy gasping for air. Each thrust brought him closer and closer, and what finally pushed him over was the warm hand wrapping around his cock and stroking him to the rhythm of their bodies. He came across his chest, and cried out as Richie kissed down his neck again. His friend wasn’t too far behind him, and Eddie whined as Richie pressed their hips together while he came too.
“Fuck…” Richie huffed. Eddie pressed kisses all over the side of his face, and then his lips when he pulled back. Richie kissed him back, as he always would, and then gently pulled out so he could lay Eddie’s body down into a more comfortable position. He reconnected their lips once he had Eddie’s knees down, and then smiled as he rubbed his cheeks with his thumbs.
“Richie…” Eddie sighed.
“Did that give you the answer you were looking for?” Richie asked. Eddie nodded and then smiled back.
“Yeah…I think you might be a little bit jealous though,” Eddie teased. Richie furrowed his brows in confusion.
“Jealous? What?”
“Of Bill? Y’know…making me say that he was no good and that you’re so much better then him?” Eddie reminded him with a cheeky smile. Richie blushed and rolled his eyes.
“Sheesh, ever heard of dirty talk, babe?”
“Yeah, but it’s never been as jealous as that,” Eddie said.
“I’m not jealous, okay? Why would I be jealous? That happened months ago, and I’m the one who has you naked right now anyways,” Richie replied before leaning down to kiss him once more. Eddie accepted it, but kept his coy smile as he pulled back.
“You sounded pretty jealous when I first brought it up,” he continued. Richie sighed.
“Okay…maybe I was a little bit jealous, but it’s fine now because I have you all to myself. Huh, baby?” He replied. Eddie nodded and then kissed the corner of his mouth.
“Yeah. I’m all yours.”