For the delightful Cindy Belle, who was a darling to me in a rough time. You are a real cutie =)
---
"Oh, it's you." I swear I almost caught a glimpse of Dana's cheer turn to ash as her suddenly annoyed face found mine opening the door instead of my sister's.
"June is making you guys snacks." I step aside and she steps in, setting a bottle of wine and a trendy-looking overnight bag on the table by the door. She shucks off her coat, revealing a rather unexpectedly stylish dress underneath, one that substantially accentuates her already very generous breasts. "In the kitchen."
"Girls' night!" Cindy bursts in the still-ajar door, as though she had been lurking just out of sight specifically so she could pop in without knocking, her cheer as perky as ever at seeing me.
"Hey," I smile at my cute fellow senior. She and my sister have always had an unusually close friendship despite their age gap. These days with June off at college most of the year, it seems like I hear more about her life indirectly through Cindy during English or math than from my sister herself. I'm probably more surprised that she's here than I ought to be.
"Dana! So cool to see you! I didn't know you were in town!" Cindy gives Dana an earnest but awkward hug, although to be fair, the awkward half was entirely Dana's. Cindy's infinite cheerfulness is as much a contrast to Dana's somber attitude as her jeans and t shirt seem when wrapped around that elegent dress.
"I, uh, just drove in." Dana picks up her bag and wine and nods toward the kitchen. "Shall we?"
"Let's!" Cindy grins, skirting past me, and I close the door, heading upstairs to leave the girls to their night.
---
I startle as the bedroom door bursts open, dropping my book on my chest.
"June says to quit beatin' yer meat and come play Monopoly with us!" Cindy bounds into the room, landing heavily on my bed beside me, jostling my book further, my place most assuredly lost now.
"Uh, where's your pants?" I pull myself upright, hesitatingly avoiding gripping Cindy's bare thigh as I do. I've known Cindy for years and I don't think she owns shorts. This is more skin up her legs than I've ever seen.
"Unlike everyone's favorite Stanford girl, I didn't actually think to bring, like, sleep clothes? But what's a sleepover without pjs!" Cindy grins. In the dim light, my eyes fall on the thin, forest green material of her t shirt, resting just snug enough against her chest to hint that her jeans aren't the only thing she takes off for bed.
She catches my eye and smacks my leg, "Be good, I'm having a nice night and I just wanna chill with my friend Frank. And besides, what are you doing up here, reading alone in your room on a Saturday night? You should hang out! Jump in! Like me!" She motions to her uncharacteristic attire. "So, I insist, you are going to put on some fun comfy pajamas too and come join us!" She smiles and I blink. What the hell, it would be nice to hang out with my sister. Cindy is right, we should just chill.
"Um, sure, I'll put something else on and be right down."
"I can wait here!" She smirks and stares and I stare back, both of us letting the other soak in the awkwardness of her strange proposal to watch me change.
"Uh, what?" I manage, standing up and helping my book find its way to my dresser. I open a drawer and pull out some fleece pajama pants. "No?" I shrug, shoving the drawer back closed.
"Darn, I was betting you slept in the nude..." Cindy laughs as she thrusts herself upright and staggers, landing back on the bed.
"Are you... drunk?"
"No, just, bad at standing..." She huffs a laugh and gets up successfully this time, slipping out the door.
I pull off my shirt and undo my jeans when her head pops right back in.
"Just to clarify, I mean, I usually do, but your sister wasn't into it. I think I'll win her over, though!"
"Drink?" I say, crossing to the door, one hand holding my jeans closed, the other reaching to lock her out.
"Nooooo, sleep nude..." She snorts at her own joke as I close and lock the door, slipping off my jeans and, after a pause, my boxers, and pulling on the pajama pants. I mean, she was right about one thing, these pajamas are really just for when I leave the room at night. She certainly seems to be jumping into it, I might as well be comfy too. Just having fun or whatever.
---
"Plane tickets are just so pricey..." June tsks at Dana as I come into the living room. She and Dana are sitting on the couch, and Cindy pats a pillow on the floor near her.
Dana, dress gone, is now in an oddly prim but seemingly as-stylish silky red pajama set, one that hugs her large breasts very complimentarily but still covers a lot of skin. And yet, as she and my sister sip their wine, it somehow seems to pair nicely with June's overly-risque-seeming lingerie. June's boy short bottoms hug as tight to her as the sheer buttoned crop top, but at least the bottoms seem fully opaque...
I have to admit, I'm pretty sure I've never actually seen my sister's breasts before, and it is hard not to try and imagine that top just a little more transparent at the moment. I can almost make out... pink? Are her nipples pink?
"Be good, dude!" Cindy smacks me with her characteristic snort. "Let's play!" She grabs her not-wine glass and tilts back a swig, coughing softly. She catches my eyes on her this time, and smirks, "Thirsty?"
"Thanks for coming down, I mean, I've missed my girls, but you've always been kind of a part of our lives, and I guess I've missed that too and..." June trails off into her wine glass, and Dana interjects.
"So! I'm sure Cindy has got you in on our little gamble?" Is Dana actually smiling at me? How much of that wine have they had?
"Gamble?" I look over at Cindy, who quite challantly sips her glass, looking up at the ceiling.
My sister chuckles. "Okay, this is a little silly, but, the idea is that the loser has to strip down and run two laps around the house." June purses her lips and likewise takes a very pointedly slow sip of wine to avoid any potential follow-up questions.
I consider this for a moment.
Probably on their second or third bottle, actually. And no way Cindy is drinking water.
But, three hot girls looking to lose at a board game and strip naked for me? I am genuinely having a little trouble physically hiding my interest... I shuffle my legs a bit, but apparently not terribly inconspicuously. Cindy chokes on her water again, and Dana tries very hard not to smile.
"Looks like a yes from here!" June does smile and finally Dana breaks, laughing.
"He's clearly excited just at the thought!" She adds through a chuckle, patting playfully at my sister's shoulder.
"Oh, oh, don't go too soft on us now!" Cindy giggles.
"Hey, maybe I'll get lucky and one of you will really suck." I gratuitously adjust myself, waggling my eyebrows at Cindy and her giggle escalates into a throaty laugh.
Just having some fun, I guess.
---
We're a few rounds in and I'm pulling ahead to an easy lead. I already have one monopoly and most of a second, and pretty much every one of the girls has split their potential monopolies between them.
I'm trying to "be good," but Cindy's t shirt slides up every time she moves, flashing these skimpy black panties that also seem to keep sliding up and she keeps needing to adjust and... It is very hard not to look, and she is not trying very hard to hide it. Not to mention how flattering my sister's outfit is when she leans over the table. Hell, I even caught myself trying to decide whether Dana has anything on under her pajamas at one point. I'm pretty certain no bra, but I can't quite discern a panty line.
I put up my first hotel and hand the dice over to Cindy, who promptly lands on it. It's a big chunk of her cash on hand, but she'll probably recover. She drums her fingers on the table for a second, then licks her lips and breathes in.
"Care to negotiate?" She flashes that smile at me, and I shrug.
"I mean, sure, I guess I'd be okay taking your railroad, or..."
"No, I mean..." She glances at my sister, who looks suspicious of her, then turns to me. "What if, like, instead of paying, I just..." She coughs, flashing her eyes at the other girls again, then back at me. "Showed-you-my-tits?" She blurts, instantly blushing.
Up to this point, it has almost all passed as maybe innocent. The pajamas, the game, adjusting her panties. The silly dare even could pass as just a goof. This is not just "jumping in."
I've been into Cindy for years. Years. I've imagined these tits as I sat next to her in math countless times.
And this look on her face? She knows it. Leverage.
"Uh..." I swallow, glancing at my sister who just shrugs her eyes and sips her wine. "Yes?"
Cindy licks her lips again, grabbing her shirt and almost shaking as she hesitates, swallows, and lifts it up.
Fuck, her tits are incredible. Gravity-defying. So much larger than they look from outside! God, I want to touch them... to lick those unexpectedly large, dark areolas... to...
"Okay, that's enough! All done!" Cindy shoves her shirt back in place, shaking still with nervousness, face flush as she settles back to her spot at the table. "Um... here you go, June, your turn." She sips her water, glancing at me. I catch her eyes scanning my lap, and at this point, I've pretty much stopped trying to hide my seemingly perpetual erection. She's clearly noticed, and is seemingly as clearly pleased about it.
Holy shit, though. Cindy's tits. Just, wow.
"Fuck." My sister picks up her cash, counting it. "Shit, fuck..." I barely glance up, still awe-struck.
"Just mortgage your..." Dana says. They're so perky!
