Truth or Dare, Round Three

“Truth or dare, then.” Brian asked.

“Dare,” Kelly decided. “Gimme something good for once.”

“Something good, huh…” Brian said, thinking back to the better dares that had been thrown around back when he played in high school. He was surprised to realize he actually did want to get back at her a little bit. She’s been going a little overboard trying to stir things up between me and Stephanie.

“Okay, I’ve got one.” He rose from the corner of the bed and picked through his pile of stuff, eventually pulling out a slim box of wrapped cereal bars, his ‘emergency convention rations’. Returning to sit on the edge of the bed across from Kelly’s seat, he tore the wrapper off of one and placed it on his thigh.

“I dare you to eat it, without using your hands,” Brian said, a little proud of himself. Emily had clumsily eaten a cookie out of his lap on a dare back during their senior year, and he’d used the memory as fap fuel for months and months.

The sight of her cute pixie-cut hair bobbing enthusiastically down by his crotch, and her blushing, flustered face as she tried to catch the crumbs scattering across his jeans with her lips. The tiny wet spots of drool she left behind, that look of triumph on her face after she ate it all, seeing the motion of her throat as she swallowed, their other friends whooping and jeering...

“Oh, thank God,” Kelly said, dropping out of her seat and onto her knees in front of him without hesitation. “Didn’t wanna say anything ‘cause you’ve already done so much for me, but… I’m really starving.”

Damn, now I actually feel bad, I should’ve offered them both some—

With a devilish grin she then lowered her face down into his crotch and nuzzled the cereal bar closer to his—

“Hey, whoa,” Brian interjected quickly.

“You said no hands,” Kelly laughed, giving the cereal bar a dainty nudge further up his thigh and gently rubbing her cheek against him. She turned, dramatically flipping her hair, and smiling up at him, and then slowly rubbed her other cheek upon his opposite thigh, making little kissy motions.

“You’re, uh, not eating,” Brian muttered, trying to force himself not to jerk or spasm. The buoyant feeling of her incredible breasts squeezing up against him as she teased her chin across his crotch and then looked up at him innocently...

“Y’know what’d be epic?” Kelly asked, giving him a wide smile. “If you just, like, unzipped your fly and whipped your dick out right now, right in my face.” Before he could respond she had buried her face in his lap again, pushing deeper, towards...

Uh-oh. Her cheek had finally brushed against the shape of his dick, which had been at half-mast and was quickly rising fully to the friction of her motions across his pants. Damn. Maybe she won’t notice—

Before he could even finish the thought, her head snapped back up to face him, a look of mock astonishment plastered across it.

Wow, she mouthed to him silently, letting that astonished look melt into a sultry smile as she slowly lowered her head back down to his lap.

“Hey, that’s enou—” he began, and just as abruptly, she leaned back from him with the cereal bar caught in her mouth. She somehow even managed to look smug even as she chewed it into her mouth and winked at him.

Damn, so much for humiliating her, Brian thought. Maybe I should’ve gone with the other dare from back then and had her give herself a wedgie?

“You know, you’re lucky I’m actually hungry, I coulda really made you suffer. Well then, pick truth or dare, Stephanie,” Kelly instructed, wiping her mouth with the back of her hand. “And, uh… actually, you got any more of those, Brian?”

“Truth,” Stephanie decided quietly.

“Okay, there’s a lot of sexy questions I had for you that’d have you all sperging out, but I thought of one that might be even more important, so… ‘fess up. What happened, way back when, that gave you your social anxiety?”

“Hey, that’s kinda…” Brian interjected, giving Kelly a nervous glance as he handed her another cereal bar. “I mean, I know you can ask anything, but do you really have to—”

“It’s okay,” Stephanie interrupted, showing a small smile. “It happened so long ago, it’s not very impressive or amazing… it’s silly, really. I can tell the whole story if you both promise not to laugh.”

“We promise,” Kelly assured, and took a large bite out of the second snack bar.

“Okay,” Stephanie started slowly, pausing to take a deep breath. “It all began in the Sea of Cats—”

“Pffffftt!” Kelly laughed, slapping a hand over her mouth. “Sorry! I... look, sorry. Continue.”

“Go on, Stephanie,” Brian said, shooting Kelly an admonishing look.

“Okay,” Stephanie continued, smiling patiently, “I was young. Twelve, maybe. And I had two friends. Ben and Jess. Ah, well, Jessica, but we just called her Jess. We grew up together, and we all played make-believe together almost every day, just the three of us. Every day we had an adventure in the Sea of Cats.”

“...The Sea of Cats.” Kelly repeated incredulously.

“Y-yeah,” Stephanie said quietly, but Kelly could detect a current of excitement in the girl’s voice. “That’s what we called it. In our neighborhood there was a big field, empty lots where they hadn’t put in new homes yet. The grass was tall and wild like a sea, and there were cats everywhere!”

“They just kept multiplying. They didn’t really belong to anyone, but I think they were too well-fed and looked-after to be considered feral. We knew them all, we gave them all names. Sometimes you’d see them curled up together, sometimes they’d squabble and chase each other... there was always something going on. Ben and Jess and I, we had a big bag of dry food, and we’d take a handful each and play, go out exploring for hungry kittens. We would watch anime and play in that field, always playing out a different story, a different adventure.”

“Okay, that makes a bit more sense,” Kelly grudgingly admitted.

“We’d watch anime and go on little adventures together in the Sea of Cats... and then, one summer, my friends... they changed.” Stephanie sighed. “They started dating... uh, they started dating each other during middle school. They’d moved on to this... idea that they were a mature couple, young adults in a relationship. They stopped playing with me, and they became distant, but also... they started to talk about me, made fun of me in school. I don’t know if it was ever really even enough to consider it bullying, but coming from them, it really just... Devastated me.

“I know it seems silly, for such a small thing so long ago to have such an effect on me. They broke up in eighth grade, but it wasn’t like things could ever go back to the way they were. Everyone but me had put all of the past behind them and grown up. I loved them both so much, and I just wanted us all to be happy together, like we used to… I couldn’t handle it. I cried. I would cry by myself for days. It’s been half a lifetime since then, and sometimes I still feel like crying.”

“All throughout high school, I wasn’t really all there, I was just trying to make myself scarce so that people wouldn’t notice me. I’d go to school and do my assignments, go home and do my homework, wish that there was more homework, so that it could keep me occupied. And then go to bed in my tidy, boring little room. I wasn’t really... um, I’m not really happy.”

“I wanted things to go back to how they were, when we went on adventures and played games together, but it was impossible. I did keep watching anime by myself... and I still play Monster Battlers... with Megan, now. My only friend… if she’ll still have me after tonight. Before I knew it, high school flew by and I’m in college now, just... getting older and somehow still waiting for those fun days with my friends to come back somehow. I guess... that’s my whole life story?”

“So you just waited for your life to magically get better and go back to the way things were?” Kelly asked, agitated. “You didn’t, I dunno, do something about it? Find new friends? Get in a relationship like they did? Something? Anything?”

“I tried a-a lot of things, I, I did,” Stephanie stammered in protest. “But I wasn’t brave… I’m not brave. I couldn’t have adventures on my own, I almost drowned when I tried. I could never reach out to make new friends in high school on my own… I didn’t even have the guts to explain to Megan why I ran out on her tonight. I’m nothing—”

“Almost drowned?” Kelly asked.

“All of that’s in the past, though,” Brian interrupted. “I mean, you’re here now, with us. Your new friends?”

“I… yeah?” Stephanie asked, brightening.

“Yeah, friends,” Kelly chimed in. “Maybe even with friends with benefits?”

“Besides, I’ve seen what you can do when you’re brave,” he said, remembering that kiss she’d given him back at the convention, that kiss that felt like it was shattering the heavens and the earth. “And it’s pretty amazing. I think that before too long, you’ll forget you ever even had any anxiety.”

“I… yeah, I wish,” Stephanie said quietly, but she wore a small smile now.

“Well, it’s your turn to ask me next anyways, so let’s see how brave you can be?” Brian said.

“Ah, uh, right. Truth or dare?” Stephanie asked.

“Dare,” he replied.

“Um, okay,” Stephanie breathed, laughing, “It’s... it’s been on my mind, ever since you said earlier, uh, what you said earlier... about... um, how you wouldn’t tell me what you think about...”

“...About my butt,” she continued in a small, embarrassed voice. “So I dare you, I dare you to, ah, to tell me now, what you thought about my butt.”

“Nope,” Brian answered, his grin spreading wider.

“Y-you’re giving up?” Stephanie asked in surprise, looking crestfallen. “You really won’t tell me?”

“No, it’s just, you can’t dare me to tell the truth about something,” he clarified. “I didn’t pick ‘truth’, I picked ‘dare’. One is one thing, and the other’s the other.”

“Hey, he’s right,” Kelly realized, a wicked smile adorning her face. “You can’t dare a truth outta him, that’s cheating. “You’ve gotta dare him to do something. That’s what you get for tryin’ to plan out all your questions before he’s picked truth or dare.”

“I, ah, yeah,” Stephanie mumbled, blushing furiously, “S-sorry, forget that question. I’ll uh, I’ll think of something else.”

“If he said that it’s something he’s gotta show you, and he picked dare, why are you still tryin’ to get him to tell you what he meant?” Kelly chimed in, exasperated. “Are you afraid of a little fondling and spanking?”

“I, um, no, I’ll...I’ll think of another question,” Stephanie said, shaking her head in embarrassment.

“Yeah, besides, that’d be no way to train my Flamituff,” Brian said. “Spanking’d be for... well, if she was bad. You’ve been a good girl all this time, haven’t you?”

“Y-yes. Yes?” Stephanie stammered nervously.

“You know, she hasn’t been that good. Just a little bit ago in the shower she was—”

“Kelly!” Stephanie yelped, mortified all over again.

“Look here, little girl,” Kelly said. “I get it. There’s probably a ton of interesting things you really want to dare Brian, isn’t there? But you’re too afraid to ask any of them?”

Stephanie reluctantly nodded.

“Well, Brian picked dare ‘cause he wants you to ask him something... interesting. Not something boring like another single piece of clothing, either. Brian just said earlier that he’s seen you be brave, and that it amazed him. So what are you gonna do? Are you going bore him, or are you gonna amaze him?”

Stephanie didn’t answer, staring at the covers with her brow furrowed cutely in thought.

“Listen,” Kelly prompted again. “Imagine for a second that tonight is already over and you’re like, looking back at it. You picked a boring, ‘safe’ dare and he ended up taking off his shoulder holster or something lame for this turn. The night wound down and the game ended, and then tomorrow came, and the next day and the next because fuck, time moves on. Months from now you’ll remember back to this moment, this chance. What’s that one question you’ll regret not having asked the most?”

“Don’t worry about all of that,” Brian said, frowning. “You ask whatever you’re comfortable with, alright?”

“I... um.” Stephanie swallowed, and turned towards Brian, her eyes still downcast on the bedspread. “Okay, I... I dare you...”

“You dare me to...?”

“I dare—I dare you to remove one piece of clothing...” she blurted out, eyes flicking up at him as she fidgeted nervously.

Kelly sighed and looked away in disappointment, resting her cheek on her palm as she slumped back in the easy chair.

“...From me,” Stephanie finished, swallowing.

“From… what?” Brian asked, surprised.

“I dare you to remove one piece of the clothing… that I’m wearing,” Stephanie explained, too embarrassed to look at him again. “And, I, uh. I want you to be... a little forceful? I-I don’t want to get hurt, I just, um, if you could be a little rough, that would…”

“Now that’s more like it!” Kelly exclaimed in approval, slapping her fist into her palm. “Steph, I knew you could do it!”

“That’s... a pretty big dare,” Brian said, swallowing and giving Kelly a glance. “You’re allowing it?”

“Either you’re gonna do it or I’ll make you do it. Get on with it,” Kelly urged, gesturing him towards Stephanie.

Brian took Stephanie by the hand and helped her stand up on the bed. With the bed being a little over two feet up off the ground, this actually had her looking down at him for a change.

“Now, uh, it’s your dare,” he said, “So if you don’t like how it goes, just... you know, say so and we’ll stop, ‘kay?”

“Oh, uh, okay,” Stephanie nervously agreed.

“No way,” Kelly objected, “She dared you, now you have to do it, whether she ends up liking it or not.”

I spent too much time with Chloe, Brian thought, sending Kelly the slightest bitter smile. How long will it be before I stop trying to ask if every little thing is okay? Okay, one piece of clothing, huh?

Taking her by the waist, he spun her around so that she was facing in the other direction, eliciting a startled yelp from the girl. The oversized shirt was long enough to hang down over her rear, and he gingerly lifted it up. The pajama bottoms right in front of him were cotton, but Stephanie’s delicious proportions still distorted the simple printed pattern on the fabric. Sweet mother of…

“Hey, don’t forget; she wants you to be a little... rough.” Kelly reminded helpfully.

Feeling an undercurrent of excitement ripple through him, Brian let the nightshirt fall back down over his hands. Then he gripped Stephanie’s waistband beneath it and slid his fingers around the circumference of her wide hips, narrowly resisting the urge to pull her towards him. Letting out a startled gasp, Stephanie wriggled beneath his unexpected touch and Brian was grateful she’d worn a shirt big enough to hang down over the tight curves of her ass, or he really would end up showing her just what he thought of it.

With his arms wrapped around her and his fingertips teasing lightly across her shivering tummy, he shoved his thumbs roughly into the waistband of her pajama pants and twisted them down.

There we are, Brian thought in relief, separating two distinct pairs of waistbands carefully with his fingers, and he could feel a tiny decorative bow on one of them. He’d been honestly concerned—he had no way of knowing whether or not she wore panties beneath her pajamas, He didn’t want to leave her completely exposed and embarrassed on her own dare—or at least, only a part of him wanted that. In the low light of just the room’s tableside lamp he hadn’t been able to tell whether she had any camisole or bra on beneath the nightshirt.

Brian pulled her pajama pants down, trying to make it seem rough, and discovered immediate resistance—his thumbs hooking the front of her waistband had only made her pajamas catch up on the shapely dimensions of her rounded bottom. He could hear her sudden intake of breath, could feel her butt slightly jiggle. Hnnnngg, okay damn, stay focused...

As he aggressively shimmied them down further, his hands occasionally brushing against her impossibly soft skin, Stephanie nearly lost her balance on the padding of the mattress. She twisted awkwardly, her hand flashing out to land on the top of his head for balance.

“S-sorry,” she said quickly, exposing a wavering smile.

“S’cool,” letting his eyes wander over her incredible legs as he steadied her so that she could step out of the pant legs one at a time. Her nightshirt covers to her mid-thigh, but still, seeing these limber legs and knowing she’s bare now all the way up to her panties…

“That was, I dunno, not very rough,” Kelly judged, sounding disappointed. “You didn’t even slap anything.”

“Th-that’s okay,” Stephanie said. Sitting back down on the bed with exaggerated care, she looked quite a bit more vulnerable without her pajama pants, but wore an excited smile now instead. “...It was just fine.”

“So, uh, truth, Stephanie? Or dare?” Brian asked, adjusting his pants suspiciously and returning to his seat on the edge of the bed.

“Dare,” Stephanie said quickly. “I’ll, uh, you can dare me to do anyth—um, any dare that you choose, I’ll… try to do.”

“Okay then,” Brian said. “I dare you to show me... how you feel about me, without telling me. How you do it, or what you do, is up to you.”

“To… show you?” Stephanie asked, biting her lip. “Like daring me to… attack you?”

“Attack him?” Kelly echoed. “The hell kind of relationship do you two actually have?”

“Yeah, you have to show me. Like, for instance; I gave my buddy Emily this same dare when we were playing a few years back... So she strides up to me, turns and like, bumps her butt into mine, turns again and cuffs me on the shoulder with her fist, and then gives me the goofiest wink and thumbs up you’ve ever seen.” He flashed a dramatic thumbs up, snapping it in close to his chest and jutting his elbow out as he winked at Stephanie.

“Pfft,” Kelly snorted. “I really do want to meet her now.”

“It was hilarious, had us all in stitches. Was one of our inside-joke things to do for ages, ‘til Chloe put a stop to it.”

“I don’t think I can beat that,” Stephanie giggled, “But, okay, um, I can try…”

“Do you want me to stand up for this?” Brian asked, beginning to rise.

“No, no… you’re fine right there, just as you are,” she said, motioning him back down as she crawled across the bed towards him. “Okay, um, here goes.”

With a shaky exhalation, Stephanie paused beside him on the bed, still on her hands and knees. The look she was giving him was seductive, in a roughly-hewn, unpolished way. There was fascination and excitement dancing in her eyes as she earnestly admired his body, and as their gazes met the glow of her smile made his heart start racing. Wordlessly, she slid a long, bare leg over his lap and straddled him, settling her weight down atop his body. Before he could collect his thoughts or stifle his reaction, he felt his dick swelling insistently, pushing forward through the wrinkles of his pant-leg to blossom into a full-on erection. Thankfully, it wouldn’t be noticeable to Stephanie—yet, anyways.

Most guys became practiced at hiding hard-ons throughout their life, and Brian was no exception. With a subtle cant of his sitting posture, his penis was pressed into his inner thigh as it grew, inching its way turgidly towards his knee. Held in place by tactile tension alone, the tiniest movement would have it springing free and rising right up into Stephanie’s panties, and Brian froze completely still. I’m definitely in trouble.

All the while Stephanie, oblivious to the turmoil she was causing, squeezed Brian into a tight embrace, arching her back and smooshing her chest against him. These small shapes, no more than handfuls, hadn’t made much of an impression on him until this moment, but now he couldn’t stop thinking about them, about the sensation of those pert little peaks upon him. He realized, almost too late, that she was hesitating, her face just beside his neck, and he couldn’t help but gulp.

I’m in so much trouble. If she tries to start kissing me here, I’m gonna… He imagined himself grabbing her buttocks, hands indenting into that perfect ass, and grinding her forcefully against him in a press of half-naked bodies. Mashing her perky little tits against his chest, rubbing up against her through in a tremor of lust that would only lead to…

But the moment of danger passed and Stephanie leaned back, shifted herself carefully out of his lap, and stood.

“Uh, I... sorry,” Stephanie apologized, turning away and hiding her face. “I, was just uh, I went with my feelings. I don’t think it was quite as memorable, but… that’s kinda how I feel, a little bit.”

“No, no, that was great,” Brian protested. “It, um—”

“Yeah, looks like it was plenty memorable,” Kelly remarked, staring. Follow her line of sight, he realized immediately that a prominent bulge had defiantly appeared in the neat lines of his dress pants. He hurriedly tucked himself back down again, giving her a strained smile. Stephanie hadn’t noticed it, thankfully, but he’d almost rather that she had seen it rather than Kelly.

Big trouble...