Playing to Win

Kelly just loved erect cocks. She unabashedly loved their phallic shape, the way they rose up to rigidity, and most of all, their potential for pleasure. She was drawn to even the idea of dicks, to their sweet juxtaposition of degenerate vulgarity and masculine magnificence. As the night pressed on, so did her craving for one, that carnal desire to get brutally fucked by one; really reamed, the kind of violent sex that had her legs quaking and filled the inside of her head with flashes of red light.

And Brian has a hard-on, right now. It wasn’t obvious. He was more clever than most in how he hid it. Even glancing toward him now, her eyes discreetly searching across his entire form with her peripheral vision, there was no obvious tell anymore, no bulge or tent pitched in his pants. But now she knew.

He must’ve been tucking his cockhead up into the elastic of his boxers, or pressing it down into his pant-leg… or something. And I’d have been none the wiser if he hadn’t gotten COCKY and dared Steph’s feelings out into the open, she thought, slightly smirking.

She’d fully intended to give the stubborn geek an erection all night. Had began to worry, even, that despite his good looks and skilled hands, he was somehow still too socially and sexually primitive to raise a rocket in this situation. She’d been very pleased to discover he’d been concealing the towering shape of a pretty impressive space-flight rocket all this time, packed with thousands of pounds of thrust and undoubtedly with all the force he needed to achieve escape velocity.

That hidden hard-on was a thrilling representation to Kelly, a manifestation of all the effort she’d put in planning her questions and guiding these geeks on the right course. Despite Brian’s attempts at seeming disinterested in taking things further, at staying detached and psychological... he was really getting involved, now. He was being drawn into the game deeper and deeper, emotionally and physically, and every turn he continued playing he was becoming further invested. Her provocations tonight hadn’t been in vain; she finally, finally had a healthy response. Of course, she wasn’t going to be satisfied with just that.

“Kell? Kelly?” Brian’s voice startled her out of her reverie.

“Hmm?” Kelly answered, realizing herself and fighting to keep her eyes from dancing down his naked chest towards his crotch.

“She’s askin’ you,” Brian said, nodding towards Stephanie.

“Truth or dare?” Stephanie asked Kelly.

“Dare, of course,” Kelly said, stretching her arms out. “I feel lucky.”

The blonde-and-pink-haired girl hesitated, frowning, before something she wanted to ask occurred to her.

“I dare you… to tell me a secret,” Stephanie finally decided.

“That’s kinda daring to tell a truth again, isn’t it?” Kelly complained, looking towards Brian for a verdict. Besides, where to even begin? Should I tell her that Brian got wood ‘cause of the way she was sittin’ on him?

“Well… it’s a little different. She’s not asking you for any specific truth, so it’s hard to call it a truth question. She’s daring you to tell her a secret, but leaving it up to you what you decide to tell her. You could reveal some shocking thing from your past, or you could end up telling her you don’t actually like mayonnaise, something trivial like that. It’s clever, a good psychological question, I like it.”

“Fine, whatever,” Kelly shrugged, rising out of the easy chair to bounce her bottom onto the bed directly next to Stephanie. “Are you ready?”

Stephanie nodded seriously, leaning in so that Kelly could whisper her secret.

“This weekend, one night or another… the three of us are all going to fuck,” Kelly confided.

“Th-that’s—!” Stephanie exclaimed, blushing. “That isn’t, that’s not a secret!”

“Oh?” Kelly responded in surprise. “It’s not? You mean, you already knew…?”

“N-no! I mean, it’s not a secret, because it won’t happ—because it’s not going to happen. If it’s not real, I don’t think it can count.”

“Oh, it’s definitely going to happen. But don’t tell Brian yet. I want him to be surprised, okay? Surprised by our little secret.”

“I—I could never tell him that,” Stephanie replied, horrified. “I mean, I-I couldn’t even if I wanted to.”

“That’s fine,” Kelly chuckled. “Secrets lose their value, their power, when more people know them, you know? Stretched between three or four people, a secret becomes gossip. Spread thin between ten or twenty, it’s just baseless rumor, right? My turn asking Brian now? Truth or dare, Brian?”

“...Dare,” He decided. “I don’t get to know the secret?”

“By the time you find out, it’ll be too late,” Kelly said cryptically, pausing a moment to deliberate her question for him. There were any number of dares she could use that fit her objectives, but the hornier she got, the harder it was not to simply choose the rather direct ones.

“Okay, whatever. I dare you, kiss me,” she challenged, looking quite pleased with herself. “This isn’t a psychological question for you—I don’t want to see what you’ll do given a choice. I don’t want you to be a gentleman, and I don’t want you to give me some dainty little kiss on the hand. Kiss me, on the lips, open-mouthed, really kiss me.”

“That’s… uh, well that’s a pretty big dare,” Brian said uneasily, glancing towards Stephanie.

“Uh, no, not really?” Kelly said. “It’s actually like, probably the most commonly dared thing in the history of the game, ever? How about it, Steph? Acting as our impartial judge here, is this dare… unfair?” It IS a psychological question, but not for Brian. How do you feel about me swapping spit with your little beloved on a dare, Stephanie girl?

Kelly shifted on the bed, bouncing over closer to Brian now. He was wearing an interesting, difficult-to-read expression. He didn’t really look pleased, but nor did he look particularly reluctant. Maybe a little nervous? Perfect.

“Uhm, h-how long, uh, how long would the kiss be?” Stephanie asked weakly. That’s so cute. She’s not gonna just okay it, but she isn’t brave enough to voice opposition to it yet, either. Am I still not pushing her enough?

“Just long enough, I guess,” Kelly answered, tapping her lip thoughtfully. “Longer than a little peck… and shorter than us starting to date, excluding you from our lives, and bullying you in middle school.”

“Th-that’s not funny,” Stephanie stammered, shocked.

“But that’s what you were worried about, isn’t it? I’m just tryin’ to have fun tonight, I’m not trying to leave you out of anything, Stephanie. Tell you what, I’ll even compromise this time. How ‘bout a double-dare; why don’t we all have a three-way kiss?”

“A three-way… kiss?” Stephanie asked, dumbfounded.

“Interested?” Kelly prompted, “I mean, they’re not really as intense as one-on-ones, ‘cause there’s no room to tilt our heads and get into it. But at the same time, three-way kisses have a certain intensity of their own, you know?”

“Do I get a say in any of this?” Brian asked, giving them a dubious look and being ignored.

“Or would you prefer to just watch us kiss this time, Steph?” Kelly asked, her eyes glimmering with excitement. “Last time it was Brian watching you while I made you feel good, now the tables’d be turned. Have you ever really seen people making out close-up, in person? It can be pretty hot. Or are you the type of girl who politely looks away when others are intimate? Do you... want to see? Or, do you want to join? Take your pick.”

“...I’ll watch,” Stephanie decided after some difficulty.

“Suit yourself,” Kelly said flippantly, and traced her fingers along the straps of Brian’s shoulder holster rig before gripping him by the shoulders.

“Come at me whenever you’re ready,” Kelly invited, glancing meaningfully across his broad shoulders and then down his bare chest. Then she closed her eyes, slightly pursed her lips, and waited. For a long moment there was nothing, just a silence of anticipation and expectation, a serene void.

Ohhhh. Ohh, here he is. Ahh..ohh?! When she felt his lips, she responded, eagerly latching onto him as though he was her lifeline. To her surprise and dismay, she quickly realized that despite all of her confidence and posturing… she was not in control of this kiss. That dizzying, falling sensation had returned, and her innate sense of superiority to these hopeless geeks wavered and then finally began to plummet.

Won’t you please just... fuck me already? She began to beg through their kiss, coiling around him and trying to suck his tongue into her mouth. She wouldn’t be some higher, celestial being that casually enticed the simple mortals beneath for much longer, she was descending. Shedding her facades and pretenses, her every nerve desperately screaming down through this geek’s atmosphere for more. More sensation, more release, more freedom, an overwhelming, aching need to accelerate and advance this destructive crash of their mouths into more than just a kiss.

Please, just... please?! Kelly was mashing her lips anxiously against his now, frenching him rough and hard. A kiss hurtling with a primordial, insatiable need, more sloppy and impatient than she’d been even when she was a horny teenager. I’m… I’m a GOOD kisser, why am I…? Kelly tried to think, but she was close, so close to this intense impact, that she couldn’t stop herself.

Scorching lust was burning away at her body and her mind was shrieking with red light. Down towards Brian, closer, closer—a trembling shiver rocked her body as she kissed him, tongue sliding across his in a trail of molten red fire. Close, so close…! That urgent, imminent feeling, the building anticipation for a sudden and breathtaking collision within her had her writhing uncontrollably—

And then Brian pushed her away, gasping for breath, and Kelly’s mind was sent tumbling, disoriented. Her red-hot meteor of desire had been subverted, mere moments before crashing down in a world-changing detonation, and Kelly felt like her mind was slingshotting all the way back into orbit.

“Wh-why?” Kelly panted, realizing her chin was damp with drool. “Why’d you stop?” I was so close! In the dim light of just the tableside lamp they were all seeing by, no one noticed the three vibrant locks of bright red now streaking through Kelly’s black hair, just behind her right ear.

“You were ‘bout to suck the life outta me,” Brian explained. “I mean, damn. If we didn’t stop there, we would’ve… well, things would’ve definitely, uh, exceeded the dare, that’s for sure.”

“So?” Kelly pouted, running a fingertip over her lips. “Dares are like, guidelines, not hard rules. Once the deed is done, it doesn’t mean we can’t keep goin’.”

“I’m sure Steph doesn’t want to see that,” Brian said.

“She might? What do you say, Stephanie?”

“It’s, ah, it’s not my turn, I don’t have to answer,” Stephanie giggled, looking flushed, and she inched back from them. Was she that close to us when we started kissing? Well, she doesn’t even seem jealous. “Whether or not you keep going is up to Brian, isn’t it? It’s his turn to ask you, now.”

“Whew, I’d almost forgotten. Dare,” Kelly decided, not even giving him an opportunity to ask. “C’mon, gimme a really good one.”

“Well… I have one that’s not all that great now, but could be really good tomorrow,” he offered.

“Oh?” Kelly asked, quirking an eyebrow. “Alright, well... sold. What’re you daring me to do?”

Brian stood up, stepping closer, bent down… and retrieved the shipping box Kelly had been interested in earlier, placing it in her lap.

“Wear this at the convention tomorrow.”

“Are you serious?” Kelly lit up, holding the box as excitedly as a Christmas morning present. “Isn’t it all... super fuckin’ expensive?”

“Well, no one’s gonna want to buy it from me if they can’t see what it looks like, right? You’d be doing me a favor by modelling it for me. If anyone compliments you or ask about it, just mention that it’s for sale, see if you can get a good offer for it, or at least like, three hundred.”

“I mean I guess, but… are you really sure? Aren’t you afraid I’m gonna like, run off with it for myself or something?” With this, with the convention pass, and the room… aren’t you a little too generous and naive, Brian?

“By all means, run off with it, then,” Brian countered. “If a pricey dress means more to you than a friend, well, then I’ll know exactly what to think, right?”

Kelly felt her mouth go dry. Before today, she would have still considered him a sucker for trusting her so blindly. Now that she was within his gravitational pull, that invisible mass shadow that seemed to draw her full attention towards him, she understood his intentions more completely.

The dare isn’t about the dress, Kelly thoughts, realizations coming together like a constellation pattern in her mind. He knew I’d wear it. It’s a gamble, a test. The dress is just collateral, and he’s wagering on… on ME. Even though I could bail on him tomorrow, take this expensive outfit for free, and laugh at him for it all I want. Yesterday, I would have.

Fuck, Kelly thought, frowning. What changed? Why is everything all so different now, getting so complicated...

“Um, uh, what is it it?” Stephanie asked, crawling across the bed so she could get a closer look.

“It’s... a costume that he’d bought for his ex,” Kelly explained, carefully passing her the box.

“It was gonna be a surprise for her, it’s a gothic lolita dress,” Brian clarified, wincing. “But obviously…”

“That’s so cool,” Stephanie said, reading the invoice. “Kelly… you’re going to look amazing. You’ll wear it tomorrow? I can’t wait to see how it looks.”

“I… yeah,” Kelly confirmed, her guilty expression fading away. “I’ll take it… the dare, I mean. For sure. Thanks, Brian. Really... thank you.”

“Hey, no guarantees that it’ll be comfy or anything. You’re Chloe’s height, but you’re a bit more, uh, well-proportioned, than her, and I don’t know if the fitting’ll be as simple as just unbuttoning part of the bust or something. Ah, anyways, it’s your turn to ask Stephanie,” he said, gesturing.

“I, um, I think I’m ready,” Stephanie said, facing Kelly and appearing to muster her courage. “For a dare this time.”

I dare you to fuck him, Kelly thought immediately. No, wait. Dare you to put your fingers somewhere inside of me, is that fuckin’ PSYCHOLOGICAL enough? Dare you to pull Brian’s cock out and give him a sloppy blowjob. To finger yourself. Talk dirty to us and moan. Threesome, right now. The thoughts careening around her head were a helplessly wheeling red starscape and for a moment Kelly felt like she was spinning adrift.

Okay, no. No, Kelly decided. She needed to calm down, Brian had been right earlier. If she gambled too big, she risked having Stephanie fold, or put her on guard and only pick truths. There has to be a proper progression here, that puts us all in JUST the right position for what needs to happen…

“Alright then, come here,” Kelly said, leaning forward in excitement and motioning Stephanie forward. “I’ve gotta whisper it to you, we don’t want Brian to know just yet.”

“Is it another secret, is that, uh, is that the dare…?” Stephanie asked hopefully.

“Just c’mere,” Kelly laughed, realizing she was still sitting directly between Stephanie and Brian. “And Brian, you shoo away further, go on.”

Stephanie crept forward in trepidation and crouched upon the bedspread, and Kelly leaned in close, cupping both hands to the shy girl’s ear.

“I dare you... to go into the bathroom and take off your panties,” Kelly whispered, as quietly as she could. “You’re not allowed to put anything else on. Ball ‘em up in your hand, come back out, and… give them to Brian to keep.”

Bewildered, Stephanie slowly turned to regard her, eyes wide with shock.

“Hey now,” Brian interrupted. “I get that you want to be all secretive and whatnot, but how can I decide if your dare’s unfair or not unless I hear it?”

“You hush,” Kelly muttered, grinning wickedly. “Well, Stephanie? It’s unfair, but is it really too unfair?”

“Um,” Stephanie swallowed. “It’s just… I don’t know, uh, if I can do it.”

Cupping her hands back around Stephanie’s ear, Kelly began to whisper again. “I know you can do it. It’s nothing but this token gesture, you know? Maidens in waiting giving their gallant knights favors before a battle, and all that. It’s like a tradition, an act of courtship.” Seeing that Stephanie was still unconvinced, wavering with uncertainty, Kelly pressed on.

“And, you know, he’ll love it,” Kelly whispered, “To you, they’re just underwear, but to him they’d symbolize, like, your sexuality. Your trust, and your affection for him. Of course, I guess you don’t have to do it if your unmentionables right now are some fifty-dollar frilly lingerie or something. I don’t know what you’re wearin’, after all. Just remember, it’s one thing to be stingy with giving away expensive undergarments, and entirely another to be stingy with your feelings… right?”

With that Kelly stopped whispering and leaned back, giving Stephanie a look of expectation. “Well? That’s the dare. Is it too much for you to handle?”

“That…” Stephanie hesitated. “Is that okay, though, I mean, I’m just wearing a nightshirt…?”

“What’s the dare?” Brian asked, curiosity eating away at him.

“You’ll see,” Kelly said. “Probably. Or, maybe this is it, and our little Stephanie’s going to disappoint you.”

“Disappoint me?”

“I... don’t know if I can do it,” Stephanie admitted, appearing to steel her nerves as she stood up. Her entire face was red she was blushing so furiously. “B-but, but I’m going to—I’m going to try.”

That’s my girl, Kelly thought, nodding in approval as Stephanie entered the bathroom and closed the door.

“What’re you having her do?”

“You’ll see,” Kelly said brightly. “Dunno how long she’ll take, though. Make-out intermission? Or hey, maybe a massage?”

“Kelly, look… it’s pretty clear what you’re trying to do here.”

“Yeah? So?” Can you even complain about it?

“I really don’t want Stephanie pushed into everything this fast,” Brian said.

“She might end up regretting it.”

“That’s up to her,” Kelly said, not relenting in the slightest. “She can stop and quit this game anytime she wants. Kiddie gloves off, remember? Besides, regretting a mistake can teach you a lot of different things in life, in a lot of ways. Regretting a missed opportunity, though, that only ever teaches you one thing.”

“You know, you’re really—” Brian gave her a playful scowl, but left the sentence unfinished, running a hand through his downy hair and glancing at the tableside clock. “What a night. Can’t believe how long we’ve actually been playing, it’s way past midnight already. We need to wind this game down soon, so we can—”

Before he could finish, the bathroom door opened and Stephanie stepped out. She stepped forward strangely, using a halting, awkward gait. One hand seemed to be nervously clutching the bottom edge of her nightshirt, holding it in place against her thigh. Fuck me, she really did it. Atta girl!

She stopped when she reached Brian, holding out her other hand in front of him. It was trembling, and he looked at her in perplexed confusion for a moment before realizing she was trying to give him something.

He opened up his hands, and she dropped a folded bit of cloth, still warm, into them. He stared at them, dumbfounded for a moment, before looking back up at Stephanie.

“They’re my panties,” She explained, clamping her free hand over her mouth then in embarrassment. “The—the ones I was wearing. Th-they’re for you to keep.”

“...Seriously?” He unfolded the panties in astonishment, unable to keep his eyes from flicking to her other hand nervously smoothing her nightshirt against her leg. They were cute, bikini-style dark gray panties, with a solid black waistband, and Kelly watched with interest as Brian plucked his fingers at the tiny decorative bow on the front of the band.

“Thank you, really… uh, damn. To keep? Thank you. But you didn’t have to go this far for me, Kelly’s pushing too—”

“I know,” Stephanie interrupted, sitting on the bed with exaggerated care. “I made my own decision, I... wanted to, I want you to have them.”

“And that’s how it is!” Kelly sang out triumphantly. “Stephanie’s turn to ask Brian now, I can’t wait to see what’ll happen.”

“Truth or dare, Brian?” Stephanie asked, apprehensively fretting with the hem of her nightshirt. The garment barely seemed to cover her thighs.

“Dare,” he answered, looking from Kelly to Stephanie uneasily.

“Okay. I dare you...” Stephanie said, visibly gathering her courage, “...to go down on me.”

“You dare me to... what?” Brian choked in surprise and disbelief. “Sounded like you just dared me to...”

“What the fuck did she just say?!” Kelly burst out, eyes wide.

“I, um... I dare you,” Stephanie mumbled, confused. “Today at the convention you said, that, uh, if I ever wanted you to g-go down on me, all I had to do was ask?”

“Christ, you said that?” Kelly snapped her attention back to Brian, baffled. “The fuck happened to all the blah blah we need to take things slow?”

“I, uh,” Brian said quickly, bewildered. “That was… Stephanie, you’re daring me to go down on you?”

“It’s okay if you can’t, can’t um, do it for real,” Stephanie added in a reassuring tone, seeming alarmed by their reactions. “I just th-thought, that maybe, since you offered, may-maybe I should ask...? To see what you would do?”

“Oh, he can definitely do it for real,” Kelly exclaimed excitedly. “This is the kinda dare I’ve been wanting all night. Awesome, Steph!” She enthusiastically gave the muddled shy girl a high-five.

“What do you mean?” Stephanie asked, looking at the girl strangely.

“You’re really going to allow this dare?” Brian asked, shooting Kelly a meaningful look. “Come on, that’s… she doesn’t really... it’s obviously going way too far.”

“Well I’m not gonna be the one to shoot her down—hell, I’m proud of her. Are you gonna back out now, after she worked up the courage all night to ask you that? I mean, can you imagine how that’d make her feel…?” Kelly couldn’t contain her exhilaration at the turn of the events and immediately situated herself beside Stephanie. This girl just saved me so much time tonight…

“Let’s just get this out of the way then, okay?” Kelly cooed, grasping the edge of Stephanie’s nightshirt and lifting it up to expose luscious pale thighs.

“W-wait! What are, you’re, uh?! What are you do-doing?!” Stephanie exclaimed in surprise, stopping the girl’s hands.

“Okay, c’mon, Kelly,” Brian said, waving his hands. “She doesn’t really, you know… realize what she asked, what it really means. There’s no way.”

The scene girl seemed to pause, quirking her lip as if just now considering that possibility. Gee, do ya think? I’m not as dense as you weebs.

“Hmmm... give us a minute?” Kelly relented, sighing loudly. “I’ll check with her, and really make sure she understands, okay?”

“Okay... yeah,” Brian said, crossing the room and giving them a bit of distance.

“Here, sit with me like this,” Kelly instructed in a hushed tone, glancing over her shoulder to make sure Brian wasn’t looking. The scene girl sat back against the bed’s headboard and opened her legs, helping Stephanie sit cradled between them. “Okay, now lean back and put your knees up and together in front of you like this…”

“But, uh?!” Stephanie protested, fearfully trying to flatten the nightshirt against her thick thighs. It was futile; with her knees raised in front of her, even though her calves hid her naughty bits from view, there was plenty of naked thigh and butt to be seen.

“It’s fine, don’t worry ‘bout it,” Kelly comforted her, adjusting until they were both comfortable. Damn, I could just start kissing and biting her neck again like this.

“...Kelly?” Stephanie whispered nervously. “Brian uh, well, guys can… actually ‘go down’ on girls?”

Hiding her cheshire grin by burying her face into the pink-streaked blonde tufts of Stephanie’s hair, Kelly composed her wickedly gleaming red thoughts and squeezed the other girl’s shoulders.

“Someone told me today,” Kelly said slowly into Stephanie’s ear. “That luck... is when preparation meets opportunity. Does it really matter whether you knew what you asked or not? We’ve been preparing you for it all night long. And now, you’ve opened up this amazing... opportunity.”

“Do you wanna get lucky?”