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Best Friends Share Everything, Right?

Summary:

Tommy’s best friend, Olivia, stops by to drop off some cupcakes for a party later, and winds up collaborating on more than party plans 👀

Notes:

You don’t *have to* be familiar with Olivia Chambers to ‘enjoy’ this smutty story. BUT why wouldn’t you want to be? I highly recommend exploring Olivia and all the other wonderful OCs in the rich universe of Harbor Station Stories that Anne // girlwonderwritesstuff has created 💜

I am grateful that she allowed me to borrow her beloved OC - hopefully she doesn’t regret it 😉

(See the end of the work for more notes.)

Work Text:

Olivia balanced the cupcake carrier precariously in one arm as she fumbled for her keyring with her other hand.

She still had plans to hit the gym and take care of a few errands before Tommy’s end-of-summer party.

If she had enough time - after the gym, and errands - she was thinking she might even drop by Eddie’s.. But only if she had time. She wasn’t prioritizing him, she told herself.

But, regardless, there was no way she was toting these cupcakes all over town. She had already invested way too much of her Saturday morning on those babies to let the icing melt as they incubated inside her car.

Her mind was in a thousand places at once, but she still managed to spare a thought to curse her workout clothes for having no pockets. She bit down on her phone to hold it lightly between her teeth as she finally located her keys in her gym bag.

Sure, she could have just knocked, or elbowed the doorbell - but deep in her subconscious she was kind of loving the challenge.

She wasn’t not a team player, but if she could accomplish something - even something as trivial as opening a door - without someone’s help, by god she was gonna do it!

She eased the key into the lock, heard the satisfying sound of it clicking open, and she let herself in. She sighed, very pleased with herself.

She thought to call out to the guys, but her mouth was still occupied by her phone, and she figured the first order of business should be setting the cupcakes down. If she fumbled them this close to the kitchen, this whole mission was pointless!

She set the cupcakes down on the kitchen island, feeling a little disappointed that there was no triumphant music or victorious glow about them.

“Multitasker extraordinaire,” she softly credited herself, putting her phone and keys in her gym bag and hitching it up over her shoulder.

She was about to announce herself when she heard.. something.

Someone.

Two someones.

“Ohh fuuck..” a moan drifted in from the next room.

Olivia clasped a hand over her jaw.

To silence her gasp, and also to catch her jaw and keep it from hitting the floor.

Evan!

She heard some indecipherable words being exchanged, and some super-wet kissing sounds coming from the next room. Those were not casual smooches. Those kisses were smoke that promised fire.

There was a small window in the wall of the kitchen that allowed her a view into the step-down living room area - where the sounds and voices were coming from.

Olivia’s heart was in her throat - not from fear, or nerves.. But she couldn’t deny that she was getting kind of a thrill from this unexpected encounter.

She swallowed the excited lump that had formed in her throat, and steeled her nerves. She was either going to look, or she wasn’t.

(There was no way she wasn’t looking.)

She slowly peeked around the periphery of the window, trying to find an angle that provided her with the most view, without sacrificing her own obscured visibility to them.

Holy shit..

Tommy’s voice didn’t carry as far as Evan’s did. But from what she could hear, Buckley was being very needy (she kept hearing something that sounded an awful lot like fuck me), and Tommy was trying to talk him down into being patient.

That freakin’ tracks, Olivia thought to herself. Having brief flashbacks to when she had wanted more from Tommy.. She had no doubt that Evan, unlike her former self, would eventually get everything that he was after from Tommy.. The question was, was Olivia really going to stick around? To still be standing there in Tommy’s kitchen when Tommy.. gave it to him?

She couldn’t tear her eyes away from the pair as Tommy pulled Evan’s shorts down until the elastic waistband sat just below the curve of Evan’s perfect, round buttcheeks. And Tommy sank to his knees in front of him.

Olivia was no longer breathing as she heard Evan moan, and she watched him rest his hands in Tommy’s hair. She watched Evan as he gently and rhythmically rocked into Tommy’s mouth.

Evan pulled back and Tommy gasped for air. There was some soft murmuring between them.

It had been intimate enough to see her best friend with a dick in his mouth.. But hearing the way he talked to him. With a soft, not-quite baby talk.. But there was certainly a lot of care and affection. It felt almost more of an intrusion to hear that soft banter than to observe the sex act itself.

Tommy opened his mouth for Evan, who slowly slid his cock back past Tommy’s lips, and over his tongue. Tommy groaned happily as Evan gagged him with it.

Olivia had to throw a hand over her mouth again to keep from reacting to the sounds. Wet, strangled sounds. She couldn’t tell from this angle if Evan was really that big, or if Tommy was just being generous with his noises and in letting Evan think that he was that big.

Olivia was well past the point of denying to herself how freakin hot this was. She felt a little light headed, and she was acutely aware of the places the blood might have rushed to to leave her feeling that way.

Her nipples were erect and sensitive beneath her sports bra. She was suddenly acutely aware of the roughness of the material, and made a mental note to buy some new activewear.

She typically didn’t wear underwear under her gym shorts. The built-in liner was enough to prevent chafing, and underwear just got bunched and restricted breathability. But right now it just left her hyper aware of how fucking wet she was.

She couldn’t just stand there and watch. She had to do.. something, or she felt like she would combust.

Olivia looked over to the dish rack, stacked with clean, drying pots and pans. She grit her teeth and spared herself one last thought of here goes nothing, before she flipped the handle of a pan and let it take down a couple others as it clattered to the kitchen floor.

It was less subtle than a simple clearing of her throat to get their attention, but Olivia was not exactly known for her subtlety.

She heard them scrambling in the living room, but didn’t give them time before calling out, “Don’t bother trying to be discreet now, guys. I’ve already seen what’s going on.”

She stepped around the corner and into the step down living room area to find Tommy using a couch pillow to cover himself, and Evan was simply using his cupped hands.

She gave them a smirk. “Nothing I haven’t seen before.”

“Oliva!” Tommy exclaimed. She couldn’t take her eyes off his wet, shining lips - as if she needed a reminder of what she’d just interrupted.

“What? Different dicks, different mouths.. but yeah. I’m familiar with the general concept-”

Tommy quickly interrupted, “What are you doing here?”

“Dropping off cupcakes?” she offered. “I didn’t realize you were..”

“Okay, L-Liv,” Evan said, more gently. “But you’re.. You’re still here.”

“Well, if I didn’t say something, who knows what I would have seen next?”

“I-I think that I know what you might’ve seen,” Evan said, grinning at Tommy.

Tommy rolled his eyes.

“I’m sorry,” she said, beginning to question this impulse. “I don’t know what I was expecting..”

“Wait,” Tommy said. “You were expecting something from all this?”

Tommy gave Evan a look that made Evan blush, which Olivia found fascinating - considering he hadn’t had the decency to blush and barely covered himself up when she walked in on him getting a blowjob from his boyfriend.

Olivia narrowed her eyes, “What does that look mean?”

“Uh..” Evan started.

“Evan has shared with me before that..” Tommy gave Evan another look, and only after Evan shrugged and nodded did he continue, “..that there was a time when you would have been exactly his type.”

“Really?” Olivia raised a curious eyebrow at Evan. “I’m sure Tommy has told you the whole story of how there was a time when he was exactly my type.”

Evan let one hand drop to his side. And the other went from less of a defensive covering to more of a holding.. warming.. almost stroking.

There was a thickness to Evan’s voice that Olivia hadn’t heard before, and that she very much enjoyed, as he said, “I, uh.. I-I’m really not sure how anyone is supposed to keep all those timelines straight a hundred percent of the time anyway.”

“And who’s to say,” Olivia continued, building on his implication, “that maybe they don’t overlap a little every once in a while?”

Olivia watched Evan’s eyes fix hungrily on her lips, which were parted slightly as she had begun to breathe a little faster as reality caught up with her:

This was happening.

Evan all but launched himself at her lips, devouring them in a way that he managed to make rough and soft at the same time.

Her heart was already thundering in her chest when she felt her shorts being slid down her legs from behind her..

Tommy..

“No panties, Chambers?” Tommy teased.

Olivia wanted to snap back at him that they were exercise shorts and there was a liner! But those clarifications didn’t seem very important as Evan continued to explore her mouth with soft sweeping motions of his tongue, and she sharply inhaled when she felt fingers teasing between her legs.

“This okay?” The question ghosted between their lips.

“Very,” she told him immediately. “Very okay.”

He covered her mouth with his again, and at the same time slid a digit between her wet lips between her legs.

She opened her eyes to peek when she felt Evan moan against her lips and saw Tommy kissing up and down his neck.

She took hold of Evan’s arm and gently moved his hand away. She brought it up to taste herself on his finger, briefly sucking on it suggestively before dropping to her knees.

She took hold of Evan’s hard cock and slipped it past her lips, immediately just.. going for it, and taking as much of him into her mouth as possible as she blindly grabbed for Tommy’s leg to encourage him to come stand beside Evan. She pulled off of Evan’s dick and didn’t even break the string of thick drool and pre-come before turning to take Tommy into her mouth. Trading back and forth between the two.

Olivia looked up to watch Evan swallow Tommy’s groans with a kiss.

They were both extremely.. vocal, and reactive.

And Olivia could tell: this was going to be fun.

“Why don’t we take this back to the bedroom?” Tommy suggested.

Olivia was pleased by how thick and lusty his voice sounded already.

And yes, she absolutely wanted to go to bed with these two.

“Lay down, baby,” Tommy told Evan.

Evan laid down on his back, sprawling across the bed horizontally with his head on the side that Tommy was standing on, and his legs stretched out over the side Olivia was on.

Tommy tapped Evan’s cheek and Evan obediently tilted his head back with his mouth wide open.

Olivia watched Tommy’s thick cock disappear into Evan’s mouth as she again kneeled down to wrap her lips around Evan’s cock.

Tommy moaned and praised Evan’s mouth, while Olivia received her own positive feedback through the way that Evan moaned around Tommy’s cock and the way that Evan’s thighs trembled as Olivia hovered over him bobbing her head artfully.

Evan tapped the bed a couple of times, like he was tapping out of a fight - and Tommy withdrew.

Olivia lifted her head slowly off of Evan, taking note of their wordless communication.

“I, uh.. I don-don’t wanna come too soon,” Evan said - irrationally shyly, considering the circumstances.

But it was sweet.

“Liv?” Evan asked, beckoning her to the mattress.

She crawled up onto the bed, and hovered over Evan.

“I.. have condoms in my gym bag,” she said.

Tommy cocked a questioning eyebrow at that fact, and Olivia just gave him a look that clearly communicated Oh, shut up without her having to say a thing.

“Good. Hey babe,” Evan called to Tommy. “Go get that?” Evan’s voice sounded slightly hoarse, raw from how he’d let Tommy fuck his throat.

“It’s in the kitchen,” she told him.

Evan suddenly flipped her over onto her back.

Fuck! he was strong.

And sweet..

She could definitely see what Tommy saw in him.

Olivia was overwhelmed with want.

Evan leaned over her and dipped his head down to kiss her deeply, and she moaned against his pillowy lips. He only pulled back when he heard Tommy return with Olivia’s gym bag.

“Here when you need it,” Tommy murmured as he stood behind Evan and pressed open mouthed kisses along his neck and down his back.

Evan stood at the side of the bed and looked down at Olivia. From this angle, they both loomed large over her in a way that made her toes curl.

“Why don’t you tell us what you want?” Evan growled softly.

She took a steadying breath, knowing - as she so often did - exactly what she wanted.

“ I want your mouth on me.”

Evan grinned, like that was the best news he’d heard all day.

“And!” she added, eyes looking past Evan to meet Tommy’s. “I want to watch you fuck him while he does it.”

“That’s a lot for you to focus on, Evan,” Tommy told him.

“I, uh.. I-I think I can manage,” Evan said eagerly.

Evan sank to his knees at the edge of the bed, and massaged her thighs, and Olivia tried to remain calm - even as inside her mind she was kicking and screaming that his mouth was not quite where she wanted it yet.

Evan looked up from his kneeling position to watch her as she subtly writhed into the mattress and ran her hands over her breasts.

She glanced down to see Evan’s arm move in a telltale motion letting her know that he was stroking himself just watching her.

He lowered his face between her legs to taste her with little quick teasing licks felt like lightning on her clit, and made her moan aloud and arch her back. She felt her knees begin to tremble, and tried to get her senses under control, as she knew that they were only just getting started.

She watched Tommy position himself behind Evan, saw - with mild frustration - how Evan’s focus drifted with the sensation of Tommy rubbing up against him.

Olivia fleetingly wondered if Evan had the attention span for this.

Tommy’s hands slid up and down Evan’s back, as Evan’s tongue moved with slow, calculated strokes.. sliding over Olivia, exploring her like a new favorite hiding spot, quickly finding all the most exciting places, humming with enthusiasm as he lost himself in her.

Tommy’s hands settled on Evan’s hips, lifting them so that Evan was up on all fours instead of kneeling.

Evan spread his knees apart slightly, a small gesture of opening himself to Tommy.

Olivia’s hand drifted down to land softly in Evan’s curls.

“You feel good,” she told him with a breathy moan.

And it was true. Evan had told Tommy that he could handle the.. multitasking. And Olivia could hear in Evan’s voice how much he wanted to be right about that. But Olivia thought that she might want it more.

Wanting more.. Next to her name in the dictionary.

Evan parted Olivia’s legs a little wider, and he teased her with some alternating warm and cool breaths and bursts of air that made her shiver and moan. He teased her lips with his fingertips, and she whined for him to press inside her with a low and honeyed voice.

Thick and sweet.

She heard Evan gasp with anticipation as Tommy began to spread Evan’s asscheeks, and swipe at him with his tongue.

Evan pressed his fingers slowly and deeply into Olivia.

Olivia hummed, teasing Evan a little. “Is that what you want Tommy to do for you? Bury his thick fingers inside of your tight little-”

Evan’s lips suckled at Olivia’s clit as he worked his fingers inside her, buried inside her soft, dripping wet pussy up to the knuckle of his hand.

His fingers were so big, she couldn’t stop her body from pulsing around them already, beginning the slow build up to something that she thought might melt her brain when it arrived.

Evan slowly withdrew his fingers, and looked at her in awe.

“So nice and pink and open for me,” he murmured. “Fuckin’ gorgeous..” he sighed reverently.

“You’re tongue makes pretty words, Buckley,” she told him. “But I wouldn’t say that’s the best way for you to use it right now.”

Evan lowered his head and slid his tongue inside her, the sensation making Olivia’s mouth fall slightly open and she held back the low moan that desperately wanted to escape.

It was all so fucking good, but she wasn’t ready to allow it to be good enough.

She felt Evan flinch for a moment and moan loudly as Tommy began to finger him, getting him ready for exactly what Olivia had asked.

Evan’s moans vibrated through Olivia, and she rocked against Evan’s face. His tongue was still deep inside her, and he moved his nose to rub against her clit.

“You’re being really good for me, Evan. Are you gonna let Tommy be really good to you?”

Evan nodded immediately, not taking his mouth off of her pussy.

“You ready, baby?” Tommy asked.

Evan hummed affirmatively, loud enough for Tommy to hear him. And Olivia’s body responded to the humming vibrations with a small shiver of pleasure.

Evan moaned deep in his chest as he experienced the dull pressure and warm stretch of Tommy’s cock pressing into his slicked up hole.

Evan had to stop to catch his breath. Which Olivia understood, even if she didn’t really appreciate it.

Evan was subconsciously bracing himself against Olivia’s thighs, gripping them so firmly that Olivia was sure he’d leave fingerprint bruises.

Evan’s jaw hung open dumbly as Tommy filled him, and Olivia - drunk on the sight of them like this - reached up to stick her finger into Evan’s mouth.

Evan gladly sucked on it for her as he grunted softly, getting used to the feeling of having Tommy inside him again.

Tommy put his large hand on the back of Evan’s head, and lowered it back down between Olivia’s legs, and told him, “I love to see my boyfriend and best friend playing so nicely together.. Make her happy for me, Evan?”

Evan didn’t need to be told twice as he resumed the skillful strokes and caresses of his tongue against her soft, slick body.

Then Tommy began to move.

He thrust his cock slowly in and out of Evan at first, working up a rhythm. Rocking his hips against Evan’s backside. Using the momentum to drive Evan’s face into Olivia’s pussy.

Olivia didn’t know what she wanted to watch more: Evan’s face as he tried to focus on her; or Tommy’s face as he fucked Evan.

They both looked so good, doing what they did so well..

Olivia reached down to hold Evan’s head against her as she ground her clit against his face, glistening with her wetness.

Evan slid his fingers inside of her and coaxed her closer to her climax.

“I’m gonna come,” Olivia conceded with a sigh. Almost not believing how quickly Evan had picked her locks.

Evan bucked his hips back against Tommy’s dick, and lapped enthusiastically over Olivia’s swollen, sensitive clit and just when Tommy was starting to pick up the pace, the pleasure boiled over and Olivia fell apart.

Her body was completely rocked by her orgasm, and she held Evan in place as she threw her head back and moaned.. riding the waves of pleasure as she rocked against his fingers and face.

When she let Evan up for air, his face shined as he panted and gasped, “Condom.. condom.. I need.. I-I.. Not done with you.”

Tommy thrust roughly from behind and Evan’s upper body collapsed onto the edge of the bed, and Olivia backed up a little, happy to watch this for a while as she idly rubbed herself.. drawing out every last bit of pleasure.

“Is he fucking you good?” she purred at Evan, his eyes looking absolutely dazed. “Hopefully, not too good. Wouldn’t want you to blow your load before you get to bury that poor, neglected cock of yours inside me.”

“Tommy..” Evan whined, as it seemed Olivia’s words had struck a chord. “Tommy.. I- You’re..”

Tommy lifted Evan up and turned them both around so that Tommy sat onto the bedside - with huge grunts and groans as they landed - with Evan in his lap.

Tommy laid back, and Olivia got a closer view of what Tommy looked like when he was borderline blissed out.

She studied his face, filing it away for later.. Because she would absolutely be thinking about that face during future.. masturbatory adventures.

Evan worked his thighs up and down, riding Tommy’s cock, and squeezing the base of his own dick, trying not to let things be over before they’d fully begun.

“Hey, Chambers,” Tommy husked. Nodding his head toward Evan. “Get fucked, would ya?”

Olivia mirrored his smirk as she walked toward the end of the bed.

Evan rolled the condom on, and gripped Olivia around the waist with one arm as he guided her toward his engorged and needy cock with the other hand.

She hoped he wouldn’t bust the second she got him inside of her. She wanted to go for a fuckin’ ride.

“Tommy, T-T-Tommy,” Evan whined. “Stop for a second. I need to..”

Tommy stilled his thrusting hips, and Evan eased Olivia onto his cock. They both groaned loudly as he filled her up.

“Fuuuuuuuck,” Olivia moaned, her nerves were still raw from her first orgasm and feeling Evan’s big cock inside of her was making her brain feel instantly staticky. “Goooddddddd, Buckley, you feel so fucking good.”

“Bounce on my dick,” Evan husked against her ear, holding her waist as she found footing between the box-spring and mattress, using the leverage to do exactly as he suggested.

Each time she let herself drop, his cock hit her just right, and there was no trace of dignity or self-awareness that was going to stop her from making the pornographic sounds that were falling out of her mouth.

Evan never had much of a filter outside the bedroom, but in the position he was in now - he’d lost it completely, and had descended into rambling babbles.

“Tommy! T-T.. Ohhhh fuck, D-Daddy.. Oh, shit.. sorry, Liv.”

“I don’t care what you say, Evan,” she gasped. “Just don’t fucking stop!”

“But I can’t.. I can’t last.. It’s so fucking much..”

“Then make me come!” Olivia cried out.

Evan and Tommy’s moans and grunts harmonized in her ears as she felt his fingers reach around to rub her clit until the steady pressure and deep dicking coordinated to make her cry out as she bore down against Evan.

She couldn’t even articulate her second climax, as she just breathlessly, silently cried out - putting her hand over Evan’s hand against her clit, holding it there as she continued to grind down against him, not being able to get enough of the feeling of him moving inside her as she pulsed around his thick cock.

“Come for me, Evan,” Tommy begged, and Olivia could only imagine how he was sweating beneath their combined weights.

With one last deep thrust, Evan came hard. His hot breath was on her back and she could feel his cock twitching inside of her.

She tried to stand on legs that felt like jelly.

Tommy sighed with the small relief of only having his boyfriend on top of him at this point.

He roughly flopped Evan over onto the mattress.

“My fucking legs are falling asleep under the weight of you two,” he complained, positioning Evan’s limp body with his ass up in the air and his face down into the mattress.

“You’re such a good boy, Evan. So good to our friend..”

Olivia wasn’t sure if she was supposed to hear all of this but she was holding onto every word as Tommy fucked Evan relentlessly, finally chasing his own orgasm - like a host that doesn’t get to sit down to their meal until the rest of the guests were satisfied. “I don’t mind sharing, baby.. As long as you remember who you belong to.”

Evan looked completely out of it, his lips moved lazily as he smiled into the mattress chanting, over and over, a simple litany, “Fuck me, Daddy.. Fuck me, Daddy..”

Until Tommy finished inside him, and collapsed on top of him with a grunt.

“Holy shit,” Tommy sighed.

“You’re heavy,” Evan whined.

Tommy considerately rolled off of him, but reminded him, “You should talk. I thought the two of you might shatter my pelvis.”

“God, that would be a travesty,” Evan sighed.

Tommy was being very.. sweet with Evan, and suddenly Olivia wasn’t sure exactly what her role here was as the endorphins began to settle.

They must have noticed the moment passing as well, because they quickly shimmied into their shorts. Evan jogged out to the living room - with a slight limp in his step - to retrieve Olivia’s gym clothes from the living room for her.

He handed them to her, and he kissed her cheek and thanked her.

“That was..” he considered what exactly a person was supposed to say after all that. “That was incredibly fun.”

“I mean, the pleasure was all mine.” But then she corrected herself. “I guess it’s more 33% mine?”

“Fifty-percent yours!” Tommy pointed out, “My man got you off twice.” He kissed Evan’s temple adoringly.

“Jealous?” she smirked.

“Not really the jealous type, actually,” Tommy smiled.

Having gotten dressed, Olivia slung her gym bag over her shoulder. “I can see that, Tommy.” She walked over to kiss his cheek. “Thanks for sharing.”

“Best friends share everything, right?” he said to her before turning to Evan. “I’m not calling you a ‘thing’, baby.”

Evan shrugged. “I’m.. I’m totally okay with being objectified by you two.” He sighed, like he was already reminiscing about something that had just happened only a matter of minutes ago.

“Cute,” Olivia coolly remarked. “So, I dropped the cupcakes off for the party later!?” She laughed.

“Thank you for that.”

“And I guess I’ll see you later then?”

“Not as much of us,” Evan quipped. “But you will see us, nonetheless.

“You’re such a dork,” Olivia could hear Tommy teasing Evan as she left the bedroom, her mind still buzzing.

Best friends share everything, right? Tommy had said.

Olivia’s thoughts couldn’t help but drift to Evan’s best friend.

Not from a place of guilt or anything. She and Eddie were hardly exclusive.

At least, that’s what she kept telling herself.

But she couldn’t help wondering if he played as well with others as Evan did.

And while what she’d just experienced was undeniably hot. Tommy.. was hot. And having the chance to watch him.. Well. Yeah. That was a choice experience.

But she couldn’t help wondering what it would be like with two men that were completely into her.

Again, Wanting more.. Next to her name in the dictionary.

Again, she thought of Eddie, and Evan.. And again she heard Tommy’s words in her mind, Best friends share everything, right?

Was that right?

God, she hoped so.

Notes:

Again, shout out to Anne for letting me play in her sandbox 💜

Please go read everything you can in her wonderful world!