Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/ works/1203763. Rating: Explicit Archive Warning: Underage Category: M/M, Other Fandom: It's_Always_Sunny_in_Philadelphia Relationship: Charlie_Kelly/Mac_(IASIP) Character: Charlie_Kelly, Mac_(It's_Always_Sunny_in_Philadelphia) Additional Tags: First_Time, Trans_Character, trans_charlie, Underage_Sex, Underage Drinking, Substance_Abuse Stats: Published: 2014-02-18 Words: 1317 ****** Charlie and Mac Lose Their Virginity ****** by will_(pointedperception) Summary Mac and Charlie had a pact that they'd lose their virginity to each other if they were still virgins by the time they were sixteen. Spoiler alert: They're sixteen, and still virgins. But that's what best friends are for, right? Notes I wanted to write something for trans Charlie (because it's my favorite headcanon), but also Mac and Charlie's first time. I figured that there's no way that Mac's ego would let him remain a virgin throughout his teenage years, so naturally, he'd decide to bang Charlie. I wrote this while in a sleepy daze in the wee hours of the morning so it probably sucks, but whatever. Hopefully it's coherent and you can enjoy them fucking each other anyway!!! Mac and Charlie had a pact. They had made this pact when they were twelve, that if they both were still virgins by the time they were sixteen, they’d bang each other. That’s what best friends do, they help each other out on losing their virginity. Especially when one friend has a dick and the other has a pussy. At least that’s what Mac said. They were already each other’s first kiss – that had happened when they were ten, because they were both curious to know what it felt like. It was followed by several drunken make outs throughout their teens, including one time when Mac’s dad caught them and Mac freaked out for a week straight. His dad never cared, though, and Mac got over it, though they stopped making out so much. Mac tried dating girls, with little luck, and Charlie just hung out with Mac, because he didn’t really care about girls so much. High school wasn’t much different, except now they’d get high together in Mac’s room every Saturday, watch shitty movies, and pass out on each other. It was incredibly white trash, but it was what they loved. It was Mac and Charlie time. “Fuck, dude.” “What?” Charlie replied nonchalantly, taking another huff of rubber cement. Mac grabbed it from him, taking a deep huff before continuing. “We’re sixteen.” Charlie found this hilarious and starting laughing. “Yeah? Where have you been for the past four months?” Mac flicked his stomach, getting a slap in return. “Charlie! We’re both sixteen and virgins.” He continued laughing for a moment, then their eyes locked and they both went silent. Shit. The pact. “Y-Your point?” “We… have to bang each other, I guess.” “Right now?” “Well, when do you want to bang me, Charlie?!” Charlie blushed and pouted, purposefully not responding. “You know we can’t break the pact.” “…I know.” Charlie looked up at him sheepishly. “I-I just – I thought you wouldn’t be a virgin by now, so…” “Yeah, so did I,” Mac sighed, leaning back against his headboard. They were quiet for a couple of minutes, both staring at different walls. “Do you want to fuck me?” Charlie murmured, nearly a whisper, as if he was afraid to ask it. Mac swallowed hard, blushing, his mind racing. “I don’t think it would be too weird. Or gay. Especially if we were drunk.” “Yeah, we should probably get really drunk for this.” Mac nodded, hesitantly getting up to go downstairs and steal some of his dad’s liquor. He came back with a bottle of whiskey, taking a chug of it and handing it to Charlie. He was curled up on the foot of Mac’s bed, knees to his chest, stomach churning with nervousness. He drank about three shots at once, then set it on Mac’s dresser. Mac sat down beside him. “Could we, uh, kiss a little first?” Charlie asked. “…Yeah.” He pressed his lips against Charlie’s softly, feeling the warmth of the whiskey trail down to his stomach as he pushed his tongue into Charlie’s mouth. It had been a while and Mac had forgotten just how much he loved kissing Charlie; more than any of those girls, anyway. It felt like too much work with them, but with Charlie it was just… natural. Maybe because they were always plastered, but maybe it was just because he really liked Charlie. He liked getting high and drunk with him, and cuddling with him, and bashing rats with him, and pretty much everything he could think of; and all of this was pulsing through Mac’s brain as he pushed Charlie down onto the bed, kissing all over his mouth and neck. Charlie moaned quietly, wrapping his arms around Mac and pulling him closer. He’d never been with anyone but Mac, and hadn’t done much other than fingering himself with no satisfaction. He hated that he couldn’t just jerk off like the other guys, nor could he really just go out and date whomever he wanted. Nobody knew except for Mac, and Charlie wanted it to stay that way. Mac bit down on his neck, sucking it into a bruise, causing Charlie to yelp. “Careful, I don’t want my parents to hear!” “Then don’t bite me! It hurts!” Charlie pouted. Mac kissed his hickey and then his lips in apology, pressing his hips against Charlie’s. Charlie could feel how hard he was through his jeans; he was already wet himself, wanting to get on with this sex thing as soon as possible. He reached down, palming Mac through his pants, eliciting a groan from the other boy. “Fuck, Charlie!” He undid his pants, tossing them and his shirt onto the floor; Charlie followed suit so they were both just in their boxers. Mac trailed his fingers along the waistband of Charlie’s boxer briefs, tugging gently. “Is… this okay?” He asked, biting his lip. Charlie nodded. “Y-Yeah, just – touch me already.” He spread his legs and closed his eyes, feeling Mac yank down his boxers and press a hand between his thighs. Charlie brought a hand up to his mouth, biting on it to suppress a moan. “Dude, your pussy is really cute.” Charlie turned bright red and considered slapping Mac, but he was rubbing against his clit and it felt fucking amazing. “S-Shut up! Are you gonna fuck me now or what?” “Do you want me to eat you out first?” There was no way Charlie was saying no to that, so down Mac went, and oh God, he was sucking and licking at him in ways Charlie had never imagined were possible. He bucked his hips, whining softly, his body surging with pleasure. “M-Mac, stop,” he ordered, pulling his head up by his hair. Mac furrowed his brow. “What’s the matter? Did I do something wrong?” “N-No, just… I want your dick in me,” Charlie blushed. Mac nodded nervously, stripping out of his boxers and positioning himself in between Charlie’s legs, pausing for a moment. “Charlie.” He had his arm over his face, blocking his view. Mac reached up and moved it beside his head. “If you don’t want to do this, we don’t have to, okay?” “I want to!” “Then why won’t you look at me?” “Because! It’s embarrassing!” He tried to hide his face again, but Mac stopped him. “Dude, you know you’ll always be my best friend, okay? I won’t see you any differently. Okay, maybe a bit, but not like that. Yeah, you have a pussy, and it’s really fucking cute, but you’re still a guy to me. Got it?” Charlie nodded and Mac leaned down to kiss him again, his dick pressing against him. “God, just fuck me, Mac!” Mac pressed into him all at once, causing Charlie to nearly bite through his lip as he tried to suppress his moaning. He could feel Mac pulsing inside of him, filling him up completely. “Jesus, Charlie, you’re so fucking tight,” he groaned, thrusting slowly into him. Charlie clawed at Mac’s back, trying to push him deeper. “You okay?” “Y-Yes, just – oh, fuck, Mac!” Charlie groaned, throwing his head back as Mac hit his g-spot, his legs clenching around his waist. He thrust harder, trying his best to hit that spot again, egged on by Charlie’s whimpering. They went at it for a solid five minutes, filled with kisses and panting and pure pleasure, until Mac couldn’t hold out any longer. “I-I’m gonna come, f- fuck!” he cried, coming almost immediately inside of the smaller boy, who was clutching onto him. He collapsed on top of Charlie, lazily kissing his neck. “Shit, Mac.” “Hmm?” “That was – really good.” Mac made lazy sounds of agreement, too spent to think coherently right now. Charlie pushed him over onto his back, cuddling into his side. “I guess we aren’t virgins anymore, huh?” “Hell yeah, dude.” “Sweet,” Charlie replied, lightly kissing Mac’s lips before falling asleep in his arms. Please drop_by_the_archive_and_comment to let the author know if you enjoyed their work!