My Sister's Bestie the Bridesmaid

Writer's Note:

This chapter is a lot tamer than usual. If you're looking for quick sex skip this one or go check the previous installments if you've not already read them :)

I scan the line of people waiting at the airport's arrivals gate, expecting to find Maddie waiting for me, probably with a shitty cardboard joke sign. And a big happy smile, her texts have turned downright horny in the past few days of our week apart.

Instead, I clock a slightly taller blonde in aviators, chewing gum and dressed like a Florida weather warning. Sweatshirt, athletic shorts, flip-flops. No sign.

I've not seen Claudia, Maddie's older sister, in person for a few years. She waves me down, already grinning.

"Hey, handsome," she says, pulling me into a no-choice bear hug. "Long time no see, kiddo!"

"Claudia!" I manage once I can breathe again. "Wasn't expecting you here."

She's already filing out of the terminal, clearly trying to outrun the rest of my flight's passengers. I try my best to keep up, even with my suitcase clattering behind me as I sidestep a toddler licking the floor.

"Yeah, Maddie was supposed to grab you," she explains as we approach a sunbaked SUV. "But there was a massive change of plans. Hop in. I'll fill you in on the way."

The car smells like baby powder and is a general mess. Checks out for a mother of three in her early thirties.

I throw my bag in the back and slide into the passenger seat.

"So, what's the big emergency?" I ask as Claudia pulls into the traffic of the busy terminal.

"You really didn't hear, huh?" She snorts. "Paige got dumped by her boyfriend. Over text.

While

she was flying down there with your parents. She had a meltdown in the airport when Maddie came to pick them up, who is now on Paige-duty."

What?

"I didn't even know she had a boyfriend," I say, deadpan.

Then I remember what Maddie and I had agreed to. We said if Paige asked about us, we'd stop dodging. Be honest. Finally face the music.

I flick my phone out of airplane mode, already bracing myself.

Immediately, I'm hit with a barrage of texts.

Maddie: CHANGE OF PLANS

Maddie: WE ARE LYING TO PAIGE

Maddie: I REPEAT: WE ARE LYING OUR ASSES OFF

"Welcome to the 'older siblings kept in the dark' club," Claudia sighs beside me.

What the fuck does she mean by that?

"Anyway, I'm just glad all you Millers made the effort to come down here. I don't know how I'd survive this wedding without someone to gossip to," she goes on, oblivious to the panic crawling up the back of my neck.

She clicks her tongue, glancing out the window. "Daniel's new bride is a total bitch."

"That's no way to talk about your future sister-in-law," I joke, trying to cover the stress in my voice.

Claudia winces and mimics shooting herself in the head, popping her gum to make the noise.

"Are your kids at the hotel?" I've not met her youngest yet. That could be a fun distraction.

"Nope, they're back home with their dad. Thank God," she tugs her aviators down just enough to wink at me, her wicked grin curling wide. "Three whole days without changing a diaper? That's the dream."

I've never noticed how much she looks like Maddie. An older, somehow even more confident Maddie.

And I'm always a little disappointed she took out the septum ring she used to rock back when she was babysitting me.

"I plan to spend the weekend buzzed on sparkling wine," she says. "You're welcome to join. I can't wait to see what the neighbors' kid looks like drunk."

"I graduated like a year ago," I snicker. "I you try to keep up, you'll be the one blacked out under the table."

She laughs. "I don't need you unconscious. Just loose enough to pump some dirt on Maddie out of you."

I freeze.

"Come on," she says lightly. "You know what I mean. I wanna know about the mystery guy she's dating. The one she won't stop texting. You two live in the same city. You've gotta have some idea."

The breath I was holding leaves my body. It's a small miracle she needs to focus on a tricky intersection and doesn't notice my reaction.

I give a forced chuckle. "Yeah, right, because with my job and loan repayments, I have time to keep up with a college student's love life."

"Crap, you were my only lead. I was gonna ask Paige, but...well. Kinda gauche now, huh?"

I spend the rest of the drive to the hotel silently thanking my guardian angel.

===

I'm leaning against the hotel's wide stone terrace railing, overlooking the dark garden below. The rehearsal dinner dragged on for an eternity, and it's nice to finally breathe in the cooler air.

Despite her earlier cynicism, Claudia shed a few tears during Daniel's improvised speech. She did keep her promise to get buzzed, though. I practically had to carry her to the elevator.

I take a long sip of my gin and tonic. The open bar is the gift that keeps on giving.

"Hey, Roman," Daniel says softly, joining me with a whiskey in hand. "Today was so crazy, I didn't get a chance to thank you for coming."

Daniel Whitmore was my hero growing up. He was the cool teenage boy from the neighborhood who had a bunch of pirated games on his PS1 and a skateboard. I spent a decent chunk of my childhood just following him around like a stray.

Was I... his Maddie?

The thought makes my stomach flip. Jesus. No. Too weird. Never think that again.

I can still remember his first marriage to his high school girlfriend. He doesn't look that different; he is still tall and broad, but a little balder and softer around the middle.

"I should be the one thanking you," I say honestly. "This hotel's insane."

Daniel lands a firm hand on my shoulder. "I'm glad you're here. It's not often we get the whole family back together."

That's not nice to Claudia's husband and kids. Also, I want to insist that Maddie and I have no blood relation.

"Here," he adds, reaching into his blazer. He pulls out two thick cigars, holding them up with a grin. "Got a little something to celebrate."

We spend the next few minutes doing our best impression of a typical male friendship: shallow conversation, alcohol, and nasty-smelling cigars.

Thankfully, a feminine voice comes to our rescue.

"Evening, gentlemen," Maddie chirps, silhouetted in the soft terrace light.

She hops up onto the stone railing, legs crossed at the ankle. I hand her my drink on reflex. She sips without hesitation, her lipstick leaving a faint smudge on the rim before she passes it back. Daniel doesn't blink. Of course, he doesn't. He's Daniel. He's cool like that.

"Where'd you vanish to?" he asks.

"Ugh," she sighs. "Had to put Paige to bed. She's a mess."

"Yeah, I heard about the breakup," Daniel says gently. "That sucks. She's a sweet kid."

"Can I try your cigar?" Maddie cuts in, done with the subject.

"Knock yourself out," I answer with a straight face.

Just like I expect, she nearly gags on the first puff, then kills the taste with a long pull from my drink. Daniel doubles over, shoulders shaking with laughter.

"What's even the point of these?" she asks, wiping her mouth with the back of her hand.

"I dunno. I like them," I mutter.

Maddie leans against me, supposedly for balance. Her palm settles on my stomach and starts moving in slow, affectionate circles. Out of Daniel's line of sight, of course.

"Is that a pool?" I ask, pointing toward the glowing blue shape in the middle of the hotel grounds.

"Yup," Daniel nods. "Pretty nice one too."

"If only my cheapskate brother had sprung for a resort with a swim-up bar," Maddie whines. "We could've made some real memories at this wedding."

"I'll let you pay for my next one," he shoots back, straightening his back. "It's heated, so feel free to have a dip, Mads. But remember, my better half expects you bright and early tomorrow. Don't go crazy."

With that, he puts out his cigar and walks away. "I need my beauty sleep. See you guys tomorrow. Big day!"

Maddie watches him go, eyes following over my shoulder. The second he rounds the corner, she leans in and kisses me.

"Missed me?" I ask a little smugly when she pulls away, emboldened by the jasmine scent in her hair.

"You have no idea." She doesn't even pretend to be cool. "Bridezilla's been on my case the whole week. I need some loving."

I bring a hand to my heart, like she hasn't just spent the week on what's basically a paid-for Florida vacation.

"Poor little Maddie had to try on a bunch of princess dresses."

She giggles. "More like a million ugly ones. Not my fault the other bridesmaids are flat. Anything they picked, I looked so slutty in."

She always manages to get my attention. But I know a thing or two about her as well.

"Walk in the garden?" I offer. "We can make out on a bench without being bothered."

"Lead the way." She plants another quick kiss and hops down.

I'm kind of disappointed we didn't get a minute to explore the place during the day. Even at night, the winding paths and the strange plants curling over them have an unshakable charm.

The quiet atmosphere is more proof the Whitmore family is getting older. At any other wedding, kids would be running all around this maze.

Despite her earlier words, Maddie ends up guiding me through the artificial jungle. We tell each other about our weeks, what our friends are up to, and what's waiting for us when we get back to the city.

Somewhere along the way, I realize this is the longest we've gone without seeing each other since I moved out of my ex-fiancée's place. The domesticity of it all is a scary prospect.

I catch the smell of chlorine before the blue glow pierces through the greenery. Of course she brought us to the pool.

It's tucked away, surrounded by thick vegetation, with a few lonely chaise lounges scattered around the edge. We can't even see the hotel from here. The only sound is the soft trickle of a fake waterfall.

"You're so single-minded sometimes," I mutter, more amused than anything.

"Huh," Maddie says, turning toward me.

But I don't feel like explaining. I grab her by the waist and pull her down with me, onto one of the chaises.

She smiles against my lips as I go in for a kiss. Then her tongue darts out to meet mine. My hands slide into her hair, soaking up the softness, her weight on my lap, straddling me.

Crap, I think I've missed her too.

But it seems Maddie doesn't share my moment of emotional actualisation.

Instead, I feel her rocking on my thigh, mashing her crotch into me.

"Are you..." I start, a little shocked.

She silences me with a rough, urgent kiss.

"I'm so fucking horny," she whispers in my ear when she catches her breath. "Haven't touched myself since I got here. I kept it for you."

There she is. I'm actually a little surprised how long she managed to keep things wholesome. I let out a quiet chuckle and drop my arms, planting my hands on the chaise behind me to lean back without getting in the way of her masturbation.

Maddie is taken aback for a second, opening her eyes to give me a frustrated glance.

"What are you doing?" She asks, picking up the pace of her gyrations. "I could use some help over here."

"I think I'll just watch. You're a big girl. You can take care of yourself."

My words make her face light up. Nailed it. The idea feels more perverted than me fingering her. It's right up her alley.

A blush creeps across her face. Her eyes bounce between mine, the bulge in my pants, and the spot where her hips grind against my thigh.

Maddie goes to untuck her top from her skirt. But I bat her hands away.

I say nothing. Just tut, disapproving, driving her mad. Her face scrunches up, and she tilts her head back. It takes a lot from me not to reach out for her. Her body heat is burning into my leg. I already know I'll have a rash tomorrow from the fabric of her panties rubbing against my pants.

For a second, it looks like she's about to come. But she crumbles next to me on the chaise, letting out a guttural, frustrated groan.

"Fuck," she says in a dragged-out moan, somewhere between a curse and a laugh. "I can't cum like that. You're such an ass."

I chortle and lean to put a kiss on her neck before getting up to my feet.

For a moment, I really consider slinging Maddie over my shoulder and taking her back to my room. But that would probably not fly with the rest of our families.

I walk to the edge of the pool, roll up my sleeves, and splash some water on my face.

"Daniel was right, pool's really nice."

I lean and move my hand around the surface, silently envying the Florida weather. We're in early November.

The sound of fabric rubbing against skin makes me turn around, already expecting to find Maddie with a hand down her panties.

Once again, I underestimate her. Her top and bra are on the ground.

"Can you chill for just one minute?" I ask.

"Come on, you know what you're doing," she shoots back, almost needy. "Letting me edge then showing off your forearms like a clit tease."

Her skirt and panties are discarded in one swift motion. A very naked Maddie then crouches to undo her strappy shoes.

"Oh, the watew is weawwy wawm Maddie." Her voice is part baby-talk, part terrible impression of mine.

She flicks the shoes away and straightens up. The pool light dances across her body in ripples, sliding over every curve. And I'm the manipulative one?

"Now get off your clothes," she continues in a sharper tone.

I watch, fascinated, as she crosses the distance to the water and dives in headfirst, clean and quiet.

Maddie stays under for a few seconds before surfacing. Grabbing the edge of the pool, she hoists herself up just enough to expose her breasts. The "hair dripping down your face" look really suits her.

There's a shift in her I've gotten good at spotting.

I'm standing above her now, upright, dry, and fully clothed. Meanwhile, she's naked and soaked at my feet. The gears turn behind her eyes, the bratty energy melting away. I don't need to look to know her thighs are probably pressed together under the water.

"Do you need help with undressing?" she asks, sweet as can be.

"I'm not getting in."

"Don't be a buzzkill, we've done

way

worse."

The way she tilts her head brings back a flood of memories I should not be thinking about right now.

I crouch to meet her eyes.

"If you get caught skinny dipping, you're just the cute college girl being quirky," I explain, trying to contain my own disappointment. "If I get caught? I go on a list somewhere."

Maddie opens her mouth to try and argue. I pounce and shove her back under.

She surfaces, sputtering. "Asshole!" She giggles, then sends a huge splash my way.

Now a little wet myself, I watch her put some distance between us. She's usually a really strong swimmer, and the pool isn't that big. But the way she sticks her ass out of the water to lure me in doesn't really help her form.

While she's distracted, I pick up her clothes. Everything but her shoes.

There are a few towels, forgotten on the chaises. She'll be able to get somewhat modest before picking up her room keys at reception.

Or so I tell myself as I walk away, snickering like a kid pulling a prank.

===

Paige's heartbreak was decidedly short-lived. My bereaved little sister ended up seated next to a handsome cousin of the bride during the ceremony. The two have not stopped laughing and leaning into one another to share touchy whispers.

She does look stunning in the dress my ex-fiancée picked for the bridesmaids of our canceled wedding.

Maddie, on the other hand, is downright sinful among the bridal party. She wasn't exaggerating when she said she put the bride's sisters to shame. But she's spent the entire day running around and is now at the close family's table, leaving me to entertain my parents.

On the plus side, Paige keeping busy means that she can't ask me about Maddie. And Maddie keeping busy means that she can't berate me for stranding her naked in the pool last night.

My house of cards still stands.

Finally, it's time for the bride and groom to share the first dance. They step into the center of the room, in the space cleared between tables. Despite what Maddie and Claudia think of their new sister-in-law, Daniel looks genuinely happy as he twirls his new wife around.

The wedding party follows. I watch an unimpressed Maddie share a dance with a dull-looking groomsman. I'm probably not the only one watching. Her dress doesn't do much to contain things when she moves too fast. But I'm sure her eyes, bright against the teal fabric, only gleam that way when they meet mine.

I bide my time in silence, sipping wine.

Dad distracts me by pulling up our local football team's game on his phone. By the time I finally raise my head, a handful of guys have already lined up to try and nab a dance with Maddie.

"Are you dancing, handsome?"

I turn to find Claudia offering me her hand with a friendly smile.

"Sure," I shrug.

Hand in hand, I lead the wrong sister to the dance floor.

"Not too bummed out your husband can't be here tonight?" I ask.

"I would have spent the evening FaceTiming the sitter if he'd come," she says, grabbing my free hand and putting it on her waist in a very tame version of a Maddie move. "I can't imagine leaving a six-month-old with a stranger."

"Ugh, the joys of parenthood," I offer.

But instead of joining my commiserations, she winks. "Well, I get to dance with a handsome fella. It's not all bad."

"Look at you, flirting with the boy you used to babysit," I say in a fake offended tone.

"Relax, I'm harmless. Besides..." She nods behind me. "I'm a little surprised I even get to dance with you."

I follow her gaze to find Maddie, who manages to avoid our eyes just in time to keep a semblance of detachment.

A cold shiver runs down my spine.

"What do you mean?"

Claudia lowers her voice, suddenly conspiratorial. "You didn't hear it from me, but I think Maddie used to have a pretty serious crush on you. Back in the day."

She shrugs. "I figured she'd try to get some time with you tonight."

She has to be pulling my leg, right?

It is a little heartwarming to see her slightly drunk smugness at her big reveal. As if the entire neighborhood didn't know about Maddie's "secret" crush.

I don't even have to force a laugh this time. I turn back to glance over at Maddie for an instant. She'd love that situation. When I refocus on Claudia, she has a strange look in her eyes.

"What?" I ask.

"I know men," she says, probably emboldened by the wine. "I told you she used to have a crush, and now you're wondering if you find her hot or not. Anyway, seems she's pretty serious about her new boyfriend. She's leaving you alone."

If I die of a heart attack tonight, Claudia should go to jail. Mother of three or not.

I share the next dance with my Mom. The one after that with Paige, who I have to talk off the ledge: Yes, it's okay to hook up with a guy at a wedding. No, I won't think less of her. Yes, I think Tray (or was it Parker?) seems nice enough.

I end up being the designated partner for every lonely relative. Even Maddie's Mom, well into her sixties, borrows my hand for a little while.

The music shifts away from the older and slower stuff toward some livelier songs when Maddie manages to escape from her suitors.

"Kill me," she moans when I reach her. "Are men seriously incapable of going thirty seconds without staring at cleavage?"

I hope I manage to raise my eyes before she finishes rolling hers.

"We're not all pigs," I say, then remember I have her entire outfit from the day before stuffed in my bag upstairs. "Well, I am. But I hear some guys are pretty decent."

The laugh she gives me tells me everything I need to know. She wouldn't mind me looking.