Naked Wednesday

"Sure thing. Uh, I'm free after second block?"

"Sounds good, bro. See you then!" He clicked off, my phone landing forgotten on my pillow as I finally let Kim up.

"Jesus," she whined. "You came too quick, you asshole! I wanted to fuck again."

"Oh, sorry, Kim," I soothed, pulling her up. My parents were watching TV down the hall and she could have a tendency to get a little loud. "I'll make it up to you next time you come over, okay?"

"Inconsiderate prick," she groused, sliding back up to finish her cuddle right where she'd started. I sighed and thought again about Ms Dubinsky and her laugh.

* * *

"Wait. What?" Ms Dubinsky was clearly busy, a brief wrinkle of annoyance crossing her forehead as she looked up from her grading. "Who did you say you were, sweetie?"

"I'm Trevor Bray." Trev was good with teachers. He had a nice manner about him. It wasn't until he had blackmail material that they saw his snaky side. "I never had you for bio, but my sister speaks really highly of you. Ashlee Bray?"

"Oh!" She brightened, the wrinkle whisked away like a sponged spill. "Oh. Ashlee's great." She eyed Trev more carefully, then examined me. "And you are? I think your last name is Vargas..."

"Brian. Brian Vargas." I wanted to drown in those massive eyes of hers. "Hi! I'm dating Ashlee."

"That's right! You used to sort of do Student Government." She arched an eyebrow, a deep pair of dimples making an appearance. "While underdressed."

My dick lurched, my smile ingratiating. "Well. We all make mistakes, Ms Dubinsky."

"Oh." She flickered her gaze back and forth between us. "And you're dating his sister? Quite the little inbred family you two have, then. Well, sit down. What's all this again?"

Trev hiked himself up on the corner of a lab table like he owned the place. "We're swimmers. Coach needs us to find a tutor because, like, science isn't really either of our strong suits?"

"Go figure," she deadpanned. "Star athletes who suck at STEM. I'm shocked."

He chose to ignore her tone. "Would you please work with us, Ms D? Just for a few weeks?"

"Sure." She yawned, her neck stretching out, and I forced my eye not to wander down her throat into the simple orange button-up she was wearing. I could catch a glimpse of a purple bra strap peeping out through her loose neckline, something that always drives me insane. I swallowed. "Meet me Wednesdays after practice. That's the tutoring day."

We swapped a glance. "Like, is Thursday available? Or Tuesday?"

"Why?" she asked swiftly. "Do you two losers have some sort of date or something on Wednesdays?"

I brightened. "Actually, that's sort of how it is, Ms D."

She blinked. "What, every Wednesday?"

I nodded happily. "Pretty much."

Her head swiveled toward Trev. "And you, Ken Doll? Also a date?"

"Oh, totally," Trev assured her. "It's important for our social development."

She shrugged; I looked surreptitiously for tit-bob, but her bra must have been working hard that day. Nipples for days... "Well, if it's that important, you two can tell your girlfriends you're available to go out with them. On Thursdays." She smiled sweetly. "That's, if you want me to sign off on your paperwork for Coach."

We both sighed, defeated.

* * *

"Babe, it'll only be a few weeks." I don't think Lily was all that upset that Naked Wednesdays were going on hiatus, per se; I think she was just annoyed that we both found science so difficult. "Maybe more like six?"

"I mean, fuck, it's only physics," she scoffed. Lily had earned an A in AP physics. As a sophomore. "Not like Dubinsky knows much about that shit, anyway. You should have picked a teacher who could meet on like Tuesday," she frumped as she stepped calmly out of her pants. I nodded approvingly at her underwear choice.

"Fuck, baby." Trev was oddly hushed. "Your ass in those panties..."

"Whatever." She was already kicking them across the room. "My folks are going up to the Lake next month. We'll just do Naked Saturday instead, and then, what. You guys are only in Homework Jail for like a month, right?"

"Something like that." Trevor was already nude on her bed, picking lint out of his belly button. "Until we get our grades up. I'm at a 67% right now. Bri?"

"I'm at 66%." I smiled as my boxers fell to the floor, my balls full today. "Looking to go for a 69," I joked with an exaggerated wink at Lily. She rolled her eyes.

"Nice try, Romeo." She was already crawling up her bed, her firm tits grazing those cumstained sheets, headed for her boyfriend's dick. "You don't get to play with my pussy, Brian," she declared, though at least she had the grace to blush; I'd played with it plenty, just not that Trev knew of. "You can probably find some diseased bitch to give up her twat when you need it."

"Yeah," Trev echoed, "just keep it out of my sister." He guffawed as Lily engulfed his dick. She was obsessive about keeping us hard, and she took it seriously, but it never really took me all that long. Just staring at her naked ass, like I was now, was enough to get my balls wobbly. Trevor watched me as I peered between her legs, seeing her sweet little pussy framed by her strong toned thighs, and he laughed again. "Dude. You totally want my girlfriend's cunt."

Lily picked her head indignantly up, her hand gripping his shaft. "I've told you, asshole, I hate that word!" She glared at him a moment before peering around curiously at me. "Is that true, Bri? Are you staring at my pussy?"

"Yeah," I shrugged, sprawling in her desk chair. She had Babyshambles playing on her little Bluetooth setup.

"He totally wants to fuck you," Trev snickered.

"Well, shit. Why not?" I shrugged, making unreadable eye contact with Lily. She was curling up in a ball between Trevor's legs, jacking him casually while eyeballing my stiffening hard-on. "She knows she's hot. Of course I want to fuck her."

"Hello!" Lily was smiling now, a little cunningly. "I'm right here, dude. You don't have to talk about me in the third person."

"I bet," Trevor went on, warming to his theme, "you couldn't control yourself in there." His hand clutched greedily at Lily's butt. "I bet you'd get inside her and just lose it."

"Yeah, Brian," Lily challenged. "Just how long do you think you could fuck me before I made you fall apart like some little bitch?"

I found her eyes again and held them as steadily as I could, my dick steel-hard. I loved Naked Wednesdays. "Lily," I drawled, "you have no idea who you're talking to. I'm renowned for my control." I winked. "Just ask Julie." I'd fucked her older sister a few times recently, which Lily didn't like being reminded of. Her eyes narrowed.

"That fat cow," she spat. "Just because you can last more than ten minutes in her sloppy bitch-pussy doesn't mean shit, Bri." She was looking at my dick again, though, a little speculatively, her eyes heavy like they'd been that one time. When we'd been waiting for Trevor to get off work. When she'd let me eat her out.

When she'd looked up at me just like that as I knelt between her thighs... when I'd had that split-second thought about just dipping my hips down and thrusting inside her...

I stretched, leaning back in her chair, my cock on full display. She loved it like this, all straight and symmetrical like a weather vane. Trev's curved to the right. "Guess we'll never know, will we?" I sighed. "Too bad."

"Man, fuck that shit." Trevor had that cruel smirk he usually got when he had a Bad Idea. "Dude. This is a special occasion, our last Naked Wednesday. I think we should celebrate with a dare."

"A dare?" Lily cocked her head. "I'm game."

"Maybe not," he snickered. "Here's the deal." Trevor was sitting up now, pushing his girlfriend up off him. "I bet you can't stop yourself from fucking her, if given the chance."

Lily giggled as she sat up Indian-style, cupping her breasts mockingly at me. "No way could he stop himself," she nodded. Her bare pussy winked at me, already juiced. She loved this kind of shit, the kinky little whore. She grinned at me when she saw where I was looking. "Could you, Bri?"

"Of course I could." I arched an eyebrow at Trevor. "What'd you have in mind, bro? What's your dare?"

"You," Trev went on seriously, "should put it in her vag. Just your head, like the first inch. Then I'll start a clock, say sixty seconds. I dare you not to stick it all the way in."

"Ooh." Lily licked her lips. "This sounds like fun."

"Really?" My cock gave a little jump at the thought, and we all laughed. "Well, obviously it's not going to be much of a challenge," I taunted, looking back at Lily's reddening pussy. "I can stay in there all day and not fuck you."

"Bullshit," Lily muttered, her eyelids lowering. She was already fighting to keep herself still, to avoid sticking her finger inside herself. "No way. You're going to shove it right in there, you little creep." She had to clear her throat. "Balls deep, man."

"Nah." I yawned. "This'll be a piece of cake. What do I get if I win?"

"Prestige," Trev said loftily. "Respect. The love and regard of all good people."

"If you can do it," Lily growled, her lip curling competitively, "I'll let you fuck me in the ass. Just once."

My eyebrows flew up, and so did Trevor's. "Wait. What?" I'd never seriously thought about it, but all of a sudden it was all I wanted. "Jesus. Did I hear you right?"

"Fuck yeah." She tossed her hair back. "No biggie. I'm not worried. Again, you're going to get your tip in, and you won't even stop," she taunted. "Big talker."

Trevor was beside himself with glee. "Let's do this shit, guys!" he crowed. He was maneuvering on the bed, getting out of the way, his fat hard-on bobbing dangerously. "How you want to do this, Lil?"

She was already in motion, her eyes bold on mine. "Just follow my lead, dipshit," she murmured at me. Her chest was flushed deep scarlet, her pussy lips swollen and red. She was totally into this. "Just a walk in the park with that cute little cock of yours," she tittered. She arranged herself on the edge of her high mattress, her legs hanging over and her arms outstretched.

Every part of her, completely exposed. I felt my mouth water.

"Come on, Brian," she husked, her voice strangely low. "Unless you want to back out..."

"At which point," Trev cut in, wanking himself shamelessly from the far side of the bed, "I'll fuck her myself. 'Cause my bitch is ripe." He leaned suddenly over, his lithe body sleek and hairless. "Give 'im hell, babe." They kissed hard, tongues dueling, as I got to my feet with my dick wobbling well above the horizontal, the tip glimmering with precum as I looked down at her, all spread for me. Her lips and chin were still shiny with Trevor's spit when I stepped up between her thighs and looked down.

And dear lord, but can there be anything better than looking down past your dick at a waiting pussy?

Lily propped herself up on her elbows, red-faced, to watch me enter her; I smiled with what I hoped looked like confidence as I bent my knees, aimed, and used my hand to line my head up between her labia.

Heat. That was the overriding sensation as I eased forward, just a teasing little bit, just enough that my eager head popped into the flaming saucepan her pussy had become. I saw goosebumps ripple along her thighs, a tremble in her hips, and then she and I shared a secret look: both of us knew she'd had to stop herself from scooting down to suck me in. She was staring wide-eyed at me now, the bed rocking when Trevor got to his feet on the far side.

"Holy shit," he gloated, peering down to see where I was just barely entering her. My cockhead felt like it had been dipped into a thick soup. "Dude. You're doing it."

"Start the clock." That was Lily, speaking through gritted teeth. I was impressed at how hard her nipples looked; I didn't need to look to know how wet she was. Indeed, I was being careful not to look down there, not to see the unforgettable sight of my penis splitting Lily open. Because she'd been right to taunt me earlier: I was itching to shove in the rest of the way.

Dimly, it occurred to me how humiliating it would be if I came from this. Like, just from this. From barely being inside her.

She was licking her lips, her eyes glued to her pussy. That was the only place we were touching; vaguely I was aware that grabbing her, anywhere else, wouldn't really be in bounds.

"That's fifteen seconds." Trev sounded almost euphoric. "This is fucking hot. How's about it, Bri? You having any trouble?"

Lily gave a tiny gasp as my dick twitched, then giggled. "Yeah," she breathed. "He's having a lot of trouble."

"Just go ahead and shove it in, bud," he urged me from close behind, low, his breath stinking of Gatorade. "Come on. I know you want to."

I mastered myself slowly, forcing a nonchalance I didn't feel as I turned to look at him. "Not as much as I want her ass later, bro."

"Fuck." The low curse sounded like it had been ripped from the girl on the bed, and when I glanced back at her I saw her chest heaving. She dragged her eyes up to her boyfriend. "And you think this is hot?" Sweat was sprouting in her cleavage. "Trev, you going to cum when Brian takes me in the shitter?"

"You two are unreal." Trevor was licking his lips now, staring down at my dick while he tugged fiercely at his own. He looked back at his phone. "That's only 25 seconds. He'll never fucking make it."

"No way," Lily agreed, and I bit my lip. They were probably right. Her pussy felt like it needed me, familiar and perfect and greedy. "Go on, Bri," she gasped up at me. "Ass or pussy, you're going to stuff that dick in me either way. Might as well get it overwith."

"Fuck off." I pulled back out, just slightly, needing to change the sensation. Needing less of her. "What's that, Trev, more than thirty?"

"Not by much," he gloated. "Fuck her, man. I know how good that cunt feels. Imagine it all around you, dude." His voice was a low, fierce mutter in my ear, and I could feel the heat off his body. "Do it."

"No." I swallowed.

"Do it!"

"No."

"Jesus fucking Christ!" spat the girl on the bed, her head falling back, "this is killing me! Fuck me already!"

"Forty seconds." I thought I could hear a rush of nerves in Trev's voice now. The kid was petrified Lily would have to make good on his dare. He emphatically did not want to have to watch me assfuck her, and I guess I could understand that. I felt an ache in my jaw where I was forcing my mouth closed, my whole body tensed like a coiled spring. "Dude, you better get in there."

"No." I could do this. I knew I could, and Lily's mouth opened in a wide, wicked smile as our eyes met: the girl loved this, her competitive side surging. She wanted to stick it to Trevor as much as I wanted to stick it into her ass, and the two of us nodded, in synch, while the clock ticked on.

And that's when Trevor shoved his finger in my butthole.

"Shit!" I yelped, driving forward away from him, and Lily gave a sudden choked, breathy gasp as I sank into her all the way, my balls smacking her taint.

"Yeah," she grunted quietly, nodding at me. All at once I was enveloped in a red, lusty haze, the feel of her tight pussy firing my mind, and before I knew it I was reaching down, my hands on her perfect thighs as I reared back for another hard thrust. Then a third. "Fuck, that feels good!" Lily groaned.

"You motherfucker," I snarled over my shoulder at Trevor, who was doubled over in laughter. "Sick freak."

"Dude." He controlled himself with an effort, then laid a comradely hand on my shoulder as Lily writhed beneath us. "Seriously. Quit fucking my girlfriend, or I'll kick your ass." I hesitated, stopping my thrusts.

"Goddamn!" Lily was wailing now. "What the fuck are you two doing? I'm right there!"

"Get out of her!" Trev, his own eyes filled with lust, shoved me rudely to the side, the game no longer any fun for him. He was all about power plays, all about mindfucks, but watching me rail his bitch was too much for him. I stumbled away, my confused dick still mindlessly twitching as I tried to keep from falling to Lily's carpet, as without any further hesitation Trevor stepped up and pushed straight into her. "Cum, baby," he urged, her feet rising off the floor to curl up behind his ass as he pummeled her.

I wasn't in the mood to wait, my questing dick needing release, the overheated atmosphere getting to all of us; Lily, her face desperate, turned hopeless eyes up to mine as I knelt on the bed beside her perfect body with my hand furious around my shaft. She was already in the middle of her orgasm, her eyes locked on mine when I let go. My white spurts roped across her chest and neck, the two of us cumming hard. I leaned over her, gasping, with Trevor still plunging doggedly into her, finally roaring out his own climax as I collapsed beside her head.

Quite a thing, those Naked Wednesdays.

* * *

"You've got someplace else to be, sweetie?"

I stirred, working hard at a velocity problem, glancing for the eightieth or ninetieth time at Ms Dubinsky's gorgeous face. This was our first tutoring session with her, an hour after practice, and I could read Trev's mind: he was wondering desperately whether there'd be time for us to get over to Lily's house. He'd told me when I'd arrived outside Ms D's classroom that he'd be surprised if she kept us the whole hour, but that certainly seemed like her intent.

Trevor, his eyes glued to the classroom clock, slouched at the lab table. He looked over at Dubinsky, then shrugged. "Honestly, Ms D, yeah."

She smiled, her whole face lighting up, and I felt my balls twinge. "You've already finished swim practice."

Trevor laughed easily. He was in loose jeans that left most of his underwear exposed when he leaned forward. "There's more to life than schoolwork and swim practice, Ms Dubinsky."

"This is true." She'd spent most of the tutoring session grading bio labs, after telling us she'd be happy to help if we needed it. I'm a bio teacher, but I took plenty of physics. And I'm definitely smarter than you two, she'd pointed out. She was still smiling; Dubinsky had a reputation as a chatterbox. "But seriously. Where else do you have to be? If it's interesting, I might let you go early..."

I picked my own head up at that. "You have no idea, Ms Dubinsky," I blurted, and Trev looked back at me with a soft chuckle. "I'm not sure how you'd define 'interesting,' though."

"Yeah," Trevor put in. "I'll bet when you say 'interesting,' you mean something like 'educational.'"

She laughed along with us, her curly hair whipping as she shook her head. "No, no guys. If I'd meant educational, I'd have said educational." She glanced up at the clock, showing ten minutes left. "Come on. Spill. What's your plan, Trevor?" My buddy looked back at me then, that long, calculating Trevor Bray glance I'd seen from him many times. Usually, it led to trouble, or at least mischief. So I did what I usually did when I saw that glance, what I'd done so often since I'd met him in the third grade.

I nodded.

This was how we got ourselves into trouble. Trevor was the idea man, I was the one who egged him on. And then we both kept going way, way past the point of common sense. Trevor turned slowly back toward Ms Dubinsky. "There's this thing that Bri and I usually do on Wednesdays, for the last couple months. Just to keep us busy."

"Thing is," I added, my cock inching up just at the thought of talking to her about this, "it's sort of weird. Probably a little hard to understand."

"Just, you know, the kind of stuff kids do when they're bored. And when they'll get kicked off the swim team if they drink," he finished with a self-deprecating laugh, and that was true enough. He never drank in season. Dubinky's eyebrows rose.