Movie Night with My Sister's Bestie

Naomi's familiar touch stirs me from sleep, her fresh hand sliding under the waistband of my shorts.

"Mimi," I murmur with a lazy grin as she wraps her fingers around my rapidly hardening cock. "Trying to get me in the mood?"

Blinking away the haze, reality hits me like a punch to the gut.

This isn't my bed. This isn't Naomi. She dumped me a month ago. I'm on the lumpy old sofa in my parents' summer lakehouse.

And the blonde woman with her hand down my pants? It is none other than Maddie--my little sister's best friend--kneeling on the floor next to the couch in just a T-shirt and panties.

The same Maddie who's been testing my resolve for the past two days. And judging by how I'm reacting to her touch, I'm failing miserably.

"Mimi," she echoes, lifting her eyes from my crotch with a curious smile. "No one calls me that. But it's cute. I can be your Mimi if you want."

I cringe at the notion. More familiarity between me and Maddie is the last thing I want. Also, it would just be plain weird to use my ex's diminutive with her.

"What are you doing," I hiss, quickly scanning the room to make sure we're not getting busted in this compromising situation.

But the sun is barely up. To Maddie's credit, she's probably the only person awake in the house right now. Except for me, I guess. And my cock.

"You think you've got it bad on the couch? Try sharing a bed with Paige," she murmurs, her hand working my shaft through my shorts with unnerving ease. "I needed to get off, and I figured you wouldn't mind lending a hand."

I groan. "And your only solution is to start jerking me off in the middle of the living room? Seriously, Maddie?"

She grins, pulling me free from my shorts with zero hesitation.

"So what? You ate me out on the beach yesterday." Maddie says as if that one crazy moment justifies this one. "Would you rather I get myself off next to your sister? I mean, she can sleep through anything, but still..."

I try to come up with something. Anything to tell her off, really.

But I'm too stunned by the awe that paints itself on Maddie's face. She's brought me to full length and is holding my cock upright, barely able to take her eyes off it. Her hand is down her panties.

Then, without warning, she leans in and drags her tongue from the base to the tip in one slow, torturous lick.

"Fuck," she says, pulling away to sit on her heels. "You taste good."

Just like that, she crawls to my bag and starts rummaging through it under my astounded gaze.

"Where are your condoms?" She asks after a moment.

"What condoms?"

"Come on," she says with a chuckle. "I'm young but not that young. Even I know guys always bring condoms with them."

"Why would I bring condoms on a family vacation? With my parents and my sister?" I retort, managing to cut myself off before mentioning my sister's annoying friend. "Besides, you're the one who's been conspiring to fuck me. You should've thought of that."

She opens her mouth to answer when the door to my parents' bedroom creaks open. I barely have time to stuff myself back into my boxers before Dad emerges.

"Hey, kiddo," he grumbles in his hoarse morning voice. "Gotta take a leak. Damn prostate." He shoots me a warm smile before noticing Maddie sitting on the floor, wearing next to nothing. "Uh, hello, Maddie. What're you doing up so early?"

I'm not sure whether I'm imagining the hint of suspicion in his tone.

"Morning, Mr. Miller," she answers without flinching. "I thought Roman might've grabbed my charger by mistake on the way here." She points at my bag. "My phone's dead."

"Sure," he nods and moves out to the bathroom, satisfied with her excuse.

As soon as the door closes behind him, I blow up at Maddie.

"That was way too close," I chide her. "You can't be that reckless."

She does look subdued for a moment. But then she gets up to her feet and saunters to the staircase.

"Well, I guess it's back to jilling in bed for poor little Maddie," she taunts before sticking her tongue out at me and dashing up the steps, leaving me hard and frustrated on the couch.

The next few hours crawl by as I stare up at the ceiling, doing my best not to think about what she might be doing in the room she shares with my sister. I lose track of time until the familiar sound of footsteps signals the start of another day. Soon enough, we're all gathered around the kitchen table.

Paige, Dad, and I have never been morning people. Mom, on the other hand, is always bright and chipper, and she's especially thrilled whenever Maddie is around. It gives her someone to chat with.

I try to focus on my coffee, but my mind drifts to the gentle pressure against my leg under the table. Somehow, Maddie always manages to find exactly the right spot to rub her foot against me without accidentally creeping out any other unfortunate family member.

But my thoughts are cut short as her next question to my Mom catches my attention.

"Mrs. Miller, I was wondering if you could drive me into town. I need to stop by the drugstore," she asks in her most innocent voice.

"What do you need? We might have it lying around the house somewhere?" Mom perks up, always attentive to my little sister's best friend's needs.

"Uhm, it's really embarrassing..." she says, her cheeks tinged with an expertly faked blush. How does she do that on command? "You know, girl stuff..."

"Oh, of course, sweetheart," Mom rushes to reassure her, clearly distressed that she's made Maddie feel awkward in front of me and Dad. Not that Dad even notices--he only has eyes for his bowl of cereal. "It's one of those months, huh?"

"Yeah, I feel like I'll need all the protection I can get."

Mom coos, and Paige lays her head on her friend's shoulder to comfort her. Both of them do not catch the subtle slyness in her words or the way her foot reaches up to press into my crotch.

I almost spit out my coffee. If Mom stumbles upon Maddie buying condoms, I'm a dead man.

"I'll give you a ride," I propose hurriedly. "I've not been to the harbor in ages."

Maddie looks pleased with herself. She gives another nudge of her heel into my rapidly hardening cock.

Paige and I walk down the street after dropping Maddie off at the drugstore.

We don't come here often during our stays at the lakehouse. The small town sits on the shore of a different lake, and its atmosphere is noticeably more touristy compared to the quiet, scattered cabins and summer homes we're used to. It's also quite a drive to get here.

There's a little marina with a wooden quay surrounded by stores and restaurants. The boats here have seen better days, but the sun washing over the harbor gives it a really cozy atmosphere.

Paige grabs my elbow, nodding toward a stall.

"Ice cream?" she asks, her voice tinged with a hopeful kind of hesitation.

I pause, caught off guard by how unsure she sounds. Have I really been such a crappy big brother that something as simple as getting ice cream feels like a stretch? Yeah, probably.

"Sure," I shrug, pushing down the guilt.

"I'm buying," Paige calls over her shoulder as she darts to the counter.

We both get a cone and find a bench overlooking the water to sit down. I put my arm on the backrest behind her.

"Glad I joined the family vacation. It's been a while," I say. She looks at me with big eyes from my admission. "Too bad it took a breakup to realize that."

She chuckles. "Yeah..." A pause, and then her tone shifts more serious. "I was really sorry when I heard about you and Naomi ending things. You guys seemed good together."

I appreciate my sister pretending that it was mutual, that Naomi hadn't dumped me three months before our wedding date.

"But seriously," she continues, nudging my side gently, "we're all really happy to have you here for once. I'm surprised. You and Maddie seem to get along too."

My breath catches in my throat before I realize that there is no double entendre in Paige's words.

I smirk, eager to deflect. "What can I say? I'm just that pleasant to be around."

Paige arches an eyebrow. "Aha." She's not buying it. "Seriously, though, I was a little worried when you agreed to give her a ride to the lakehouse. Quite the road trip."

I wince, thinking back to the hours spent stuck behind a pile-up, the night spent on a motel couch while Maddie strutted around the bedroom wearing a thin T-shirt and panties. And, of course, the road head she gave me on the final leg of the journey.

"What do you mean? We've known each other forever," I say, keeping my voice light.

"Exactly," Paige replies as if it's the most obvious thing in the world. "You used to avoid us like the plague. You and Maddie have lived in the same city for a year, and you never met up with her."

I go for my usual excuse. "I was really busy." Before she can call me out, I tap my cone against her nose, leaving a smear of melting ice cream. She giggles, swatting my hand away.

"Sure," she says, wiping her face with a grin. "But you get what I mean. Maddie was too nervous to ask if she could ride with you. That's why I had to do it for her."

I'm thrown off for a moment. Maddie, nervous? The same girl who's been relentlessly trying to seduce me? It's hard to imagine her having to go through someone else to ask me for a favor.

Thankfully, I don't have to consider this paradox for much longer. I can already see Maddie skipping toward us, a satisfied grin plastered on her face and a crumpled drugstore paper bag swinging in her hand.

I still feel a little guilty about Paige's revelation. So I don't complain when Maddie takes a long, exaggerated lick from my ice cream cone, her eyes locking with mine.

I step out of the bathroom and head into the living room, spotting Maddie crouched in front of the TV cabinet, rifling through its contents. She looks up at the sound of my footsteps, her lips curving into a bright smile.

Though we've only arrived at the lakehouse yesterday, she's already taken full advantage of the beach. Her skin glows with a warm golden hue, and faint freckles now highlight her blue eyes.

I push away the thought of just how few tan lines she must have, thanks to her new habit of sunning topless.

"You're staring," she says, sounding pleased with herself.

I snap out of it. "Like you care," I answer, just a little too fast to pull off the detached tone I'm going for. Her smile only widens. "What're you up to?"

"Paige and I were thinking of watching a movie," Maddie turns back to the cabinet, and her tongue peeks out as she stretches to reach something buried deep in the back. With a small groan of effort, she finally pulls it free, holding it up victoriously.

"Look what I found!" she says proudly, sticking our old Princess Bride VHS under my nose.

"Does the player even work anymore?" I ask.

"Only one way to find out!"

Mom and Dad have already retired for the night, and there's not much else to do around here. So I sink into the couch, watching with a mix of amusement and nostalgia as Maddie crouches in front of the ancient VCR. She mutters under her breath, fiddling with the buttons in a collection of plastic clanks. She must have been nine the last time we used it, and it shows. But eventually, I hear the familiar sound of a cassette being swallowed.

Maddie rushes to join me with a triumphant "Aha!". To my surprise, and maybe just a touch of disappointment, she sits on my right side, leaving a respectable distance. Still, her shoulder, bared by her tank top, rubs against the skin of my arm.

She fiddles with the remote, and the TV turns on, displaying Fred Savage's face. What a blast from the past.

"Did you guys choose a movie?" Paige calls out, emerging from the kitchen. She's got a large bowl of popcorn, still steaming. "Oh, great choice."

"I know, right?" Maddie smirks, holding her arms out, inviting Paige to join her on the couch.

But Paige stops to my left instead, nudging her head toward me. "Scootch over," she says, shifting her weight as I reluctantly comply.

The next thing I know, I'm sandwiched between them--Paige leaning into my left side with the bowl of popcorn resting precariously on her lap and Maddie on my right, who now takes the full opportunity to press herself into me.

Without a word, Maddie reaches down and grabs the blanket I folded under a cushion earlier that morning. She drapes it across all three of us.

"It gets chilly at night," she says innocently when I glance at her sideways, though the sparkle in her eyes says otherwise.

"Shush," Paige scolds us as the movie starts, her gaze glued to the screen.

For a while, we snack on popcorn in silence, the VHS's grainy audio struggling to drown out the noise of our chewing. But then the worst happens.

Paige and Maddie, unable to resist, start reciting entire scenes word for word. I know the movie by heart, too, but it's been years since I last watched it, and I'd actually like to enjoy it. This is just so annoying.

"Alright, I'm going to bed," I sigh, beginning to extricate myself from the tangle of limbs on the couch.

"What bed?" Paige asks, her voice full of genuine confusion.

I freeze. How could I forget? I'm sleeping on the couch for the week.

"Crap."

Maddie breaks into an amused giggle.

"You're stuck watching the movie with us, airhead," my sister continues.

"You fell victim to one of the classic blunders!" Maddie exclaims, laughing so hard she has to clutch the blanket. What a dork.

I grunt but sink back into the cushion, resigning myself to my fate. In the blink of an eye, Maddie presses herself against my side again, her shoulder snug against mine. The sweet, floral scent of her shampoo drifts up, softening my annoyance. The hand she slides under the blanket and her fingers brushing my thigh do far more to distract me.

"You should see the bright side of things," she says in a teasing tone. "Now you can brag to your friend that you had two girls in your bed..."

"Maddie..." Paige and I groan in unison.

My sister leans over me to meet Maddie's eyes, whose head is tucked smugly into the crook of my neck.

"You're such a weirdo," she says in an affectionate tone, gently flicking her forehead, causing her to whimper weakly.

We resume watching the movie, but I have a hard time keeping up with the familiar story. Maddie's hand is now taking full advantage of the blanket's cover. She doesn't have to work really hard to bring me to a full erection, what with her chest pressing directly into my arm and her soft hair all over my neck and chest.

I'm stuck drifting back and forth between the feeling of immense pleasure at her touch and the dread from the possibility of Paige catching on to our games. Granted, she's been far too happy to see Maddie and me getting along reasonably well to suspect anything so far, but you never know.

I steal a glance at her, but she's leaning forward, engrossed in the screen, munching on popcorn and reacting to every scene.

Maddie puts a short lick on the corner of my jaw, pulling my eyes back on her. I can't help but smile when I see the look of indignation on her face. The message is clear, my attention belongs to her. Her stroking under the cover becomes slower but tighter, making it impossible for me to focus on anything else.

"Hey Paige," she pipes up. "Remember how Roman always wanted to skip the romantic scenes in this movie when we were kids?"

Paige snorts. "Of course. He only cared about the sword fights. Boys and their swords."

"Oh, I don't know," Maddie answers in a low voice. "I think quite a few girls love playing with boys' swords too." She squeezes my cock, making me stifle a moan.

"God, Maddie," Paige says, exasperated. ""Stop being such a tease. You're going to make Roman uncomfortable."

I have a thousand comebacks swirling in my head, but I think better of saying anything in my current predicament.

"How dare you?" Maddie gasps, feigning outrage. "I would never!"

They both burst into laughter and for a brief moment, I think I'm safe. But then Paige shifts, pulling herself out from under the covers. My relief is short-lived as she leans back against the armrest and swings her legs over Maddie's and my lap.

My heart nearly stops. Her legs settle just inches from Maddie's hand, which is still very much working on me under the blanket. The close call sends a surge of panic through me, every nerve on high alert.

This is too much. I can feel myself softening in Maddie's frustrated grasp. She tries to coax me back, her fingers stroking with slow, deliberate pressure, but Paige's new position forces her to be far more discreet. It's a losing battle, and Maddie knows it.

Things go back to normal, well as normal as they can be, with your little sister's nineteen-year-old best friend resting her fingers on your soft cock. I think Maddie has given up.

Then I feel her hand slide away, gliding over my thigh as she withdraws from under the blanket. I sneak a glance in her direction, expecting her to sit back and focus on the movie. Instead, Maddie raises her hand to her nose, her eyes closing as she inhales deeply.

I nearly lose my composure.

What the hell is it with her and the smell of my cock? My chest tightens, a mixture of disbelief and something baser growing inside as I watch her savor the scent. The sight is so brazen, so completely Maddie, that I almost snap out.

Almost.

Instead, I force myself to look over at Paige, a knot in my gut as I assess her reaction to Maddie's shameless display. But to my surprise, her head is tilted against the armrest, a cushion clutched to her chest. Her eyes are closed, and her breathing is slow and even.

"Paige?" I call out gently.

No response. My pulse quickens as I study her face, searching for any sign of movement. After a full afternoon of swimming around the lake, it makes sense she'd be tired. She's not in as good shape as Maddie or me.

"Paige?" I repeat, slightly louder this time. Still nothing.

That's all I need. Without giving Maddie time to react, I slide my hand beneath the blanket, pushing it between her thighs.

Her gasp is sharp but quiet, her body jolting slightly against mine. For a moment, I think she'll resist, but instead, she spreads herself, her legs shifting hungrily to offer me better access. My fingers trail down her stomach, her soft skin warm and writhing under my touch.

The air beneath the blanket is hot, but inside her panties, it's practically burning. Her little patch of blonde hair is already slick, matted to her skin with need.

I deliberately avoid Maddie's clit, skimming just close enough to make her hips twitch in frustration. I can feel the tension building in her body, her legs trembling slightly, but she needs to learn a little patience. Just like her thighs, her folds offer no resistance, welcoming my touch as I trace her wet heat.

Her eyes are glued to me while I look at the TV, feigning indifference. Her arms snake around my torso to anchor herself to my body as if she is afraid I could get up and leave her unsatisfied.

I tease her pussy with just one finger, running it along her lips, making sure to leave her needy nub ignored. Then, gently, I press the pad of my index finger to her entrance, slowly and carefully slipping inside.

Her breath hitches as she kisses my neck.

"Please, Rom..." She whimpers.

I pay her no mind. She's teased enough. My turn now.

I pull out completely under Maddie's horrified gaze, my soaked hand feeling cold in the open air. But I don't give her the time to complain. I bring my fingers to her face and brush them against her lips.

"Open up," I murmur, keeping my tone even and calm. "You're not ready for me. I need you to help."