Dare

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NeverSmart
NeverSmart
154 Followers

"Yeah, I could do pizza, but you'll have to call it in. We'll pick it up or will take forever," I advised.

"I'll call now. Supreme good?" Amy asked, holding the phone to her ear.

"Whatever you want," I answered, earning an appreciative smile.

Thirty minutes later, a family pizza missing two large slices occupied the third seat on our family-room couch.

"I couldn't wait to get in to my pj's," Amy said with a mouthful of pizza.

"Do you have to work tomorrow?" I asked, stuffing the last of a pizza crust in my mouth.

"No, thank God. I can sleep in," she replied happily.

"What about you? Are you doing anything tomorrow?" Amy asked, biting in to a second slice.

"I have some consulting stuff to work on, but nothing urgent," I answered, considering a fourth slice.

"Oh, and an assignment for next semester too," I added, remembering the schematics I was designing.

On the coffee table, Amy's iPhone chirped once and then buzzed.

Wiping her hands on a serviette, Amy reached for her phone and scanned its screen.

Satisfied, I tossed the pizza box on the coffee table and then started searching for something to watch on tv.

Amy had been intently texting for ten minutes.

"Who is it?" I asked bored with what passed for entertainment.

"Jessica. She's at her grandma's place and she's bored," Amy answered, pulling her feet up under her and turning to face me.

"Why did she go?" I asked.

"They're only staying the night. They're all driving up to her aunt and uncle's tomorrow," Amy explained, with a look on her face that I couldn't quite interpret.

I continued to watch Amy as her phone chirp again.

"Cow," she muttered, after reading the message.

"What's wrong?" I asked intrigued.

"Nothing. Jessica's giving me hard time about something," she replied exasperated.

"What?" I pressed, having a good idea of what that something might be.

"Fuck," Amy muttered and looked up.

"Last night...I was ...naked in the bathroom, right?" Amy asked, looking straight at me causing my groin to stir.

"Yeees," I answered, failing to stop a smile.

"Well, I told Jessica about our arrangement. The fifty bucks and stuff...anyway, she dared me to do it," Amy said as if she had been sentenced to a jail term.

"So? I didn't expect you to do it," I confessed truthfully.

"So, here's the thing. When Jessica dares me to do something, I have to do it," she explained.

"Well, I did see you naked," I said, pretending to try and help Amy.

"That's what I've been saying, but Jessica says it doesn't count," Amy complained.

"So what? Just ignore her," I suggested, knowing Amy's predicament.

"I can't," she replied flatly.

"Why not? It's just a dare," I retorted.

Amy fell silent and stared hard at me, looking conflicted.

"Okay. So, it's like this. Jessica and I have been playing a sort of "Truth or Dare", without the truth part," she confessed.

"It would just be...wrong not to do a dare," Amy concluded, looking completely defeated.

"Okay. So, just tell her you did it. I'll say you did if she asks," I pledged, feeling as if I was slow playing a mark.

"Thanks, but there's one other thing. We always record our dares as proof," she said.

Checkmate.

"What are you going to do?" I asked, sharing a knowing grin with Amy.

Playfully pitching her iPhone at me, she asked sarcastically, "You had to ask to see me naked?"

"You know how it works. Tell me when you are ready to start recording," Amy said, throwing her hair back and then sitting up straight.

Smirking, I fished her phone out of my lap, set it to capture video and then nodded.

"Shut up! Just sit there," Amy said, trying not to laugh as I smiled wildly with glee.

"What? I didn't say anything. Okay. Go," I said laughing.

"Stop it. Okay. So, Jessica. I can't believe you dared me to do this. Last night, I borrowed fifty dollars from Matty, and Matty said I had to get naked if I wanted the money," she surmised.

"So, to make sure I didn't back out, you made it a dare. Thanks. I'm calling this dare the "Payback Matt" dare," Amy finished, grasping the hem of her t-shirt.

Rolling her eyes, she pulled the t-shirt up over her head and let it fall to the floor. A pastel pink bra followed, but unlike last night, the bra hook was at the front, which somehow seemed even sexier.

"Wanna give me a hand?" Amy asked, straightening her legs and lifting her hips.

"Sure!" I replied a little embarrassed at my eagerness for a moment.

Tugging gently at her knee, her pajama bottoms fell off her hips and down to her thighs.

Sitting back down and lifting her feet allowed me to pull Amy's pants the rest of the way off.

"Ta-da!" Amy giggled nervously, attempting to embrace the moment.

"Wow! You look hot!" I approved boisterously.

"Are you okay with this?" I asked hesitantly, suddenly feeling strangely awkward.

"It feels a little weird...but yeah, I'm good. The compliments help," she replied, sounding more confident.

"So, is that it?" I asked tentatively, panning the iPhone around to include the pile of clothing.

"If you're satisfied, then yeah, it's done," Amy answered, shrugging.

"What if I wanted to see your butt?" I asked coyly, my own comfort with the situation growing.

"Do you want to see my butt?" Amy countered, grinning.

"I would love to see your butt," I replied.

Without a word, Amy turned over and knelt on all fours, her hands gripping the couch arm.

"Satisfied?" she asked.

Amy looked back over her shoulder, reminding me of a scene from the early hours of the morning.

Tapping her iPhone's screen, I killed the recording and handed the phone back to the still naked Amy.

Amy took the phone and proceeded to tap its screen at speed.

"Okay. I just sent the video off to Jessica. That should shut her up," Amy said, satisfied.

"You know, I wouldn't have made you strip, right?" I grinned as Amy collected her clothes.

"I know. That's why I took the money," Amy smiled back.

"You don't have to pay me back the fifty. I think you earned it," I offered genuinely.

"Are you suggesting that I'm a prostitute?" she accused, tongue firmly pressed in cheek.

"A lap dancer at most," I quipped back.

Locking eyes, we tried to stare each other down only to burst out in a shared fit of laughter.

As our laughter subsided, I remembered mom's new itinerary.

"Hey, mom's not coming home 'til Wednesday," I said, taking a deep breath.

"In that case, I better take your offer. Who knows? I may have to borrow some more," Amy teased, giving me a wink and a lingering leer.

For the first time in a long time, Amy and I were sharing a moment and it seemed that neither of us cared that it was sexual.

An expectant chirp and shudder from her phone, inadvertently consummated the moment by causing Amy to fall off balance on to my lap, attempting to reach for it.

Jessica had answered Amy's post with a string of messages that made the phone sound like it was having a digital fit.

"Do you want any more?" I asked, helping her up.

"Sorry. What?" Amy asked distractedly, trying to right herself.

"I'm going to put this in the fridge. Do you want another slice?" I rephrased, picking up the box.

"No thanks. I'm good," she replied, patting her stomach.

Finding space in the fridge for tomorrow's breakfast, gave me valuable time to think consider the situation.

"Could you grab my pillow and a quilt Matty?" Amy yelled.

"Okay," I called back, heading for her room.

"I'm wrecked. Could you do me a big favor, please?" Amy asked sweetly, hearing me approach.

"Name it," I answered, handing her the requested items.

"Would you rub my back like you did last night? It felt so nice," she asked, wearing a shy, irresistible smile.

"I think I can manage that," I agreed, sitting back down.

Pillow nestled beside me, Amy spread out employing cat-like grace to presenting her back.

"Oh, yes," she breathed, contently soaking up my attention.

"So, what's the deal with the dare game you guys play?" I asked, wanting to keep Amy engaged.

"No one's meant to know, but... seeing as though you already know about it..." she rationalized lazily.

The game had been created as an excuse to use Jessica's new iPhone. However, they too had loved the short episodes and just kept on playing.

I had guessed correctly regarding the rules the only new rule was that a new dare could not begin until the current one was finished.

Listening to the excitement in Amy's voice combined with her bristling body language, crystallized a decision in my mind. I wanted to play.

"Have you guys ever included anyone else?" I asked.

"Nope. You're it Matty. It's a really big secret, so don't tell anyone. Especially not Greg," she pleaded, craning her neck to look up at me.

"Why would I tell anyone? Ames, you can trust me," I reassured her.

"Good," Amy said relaxing again.

"Besides, I'm hopin' you need to borrow some more money. I might get to see you again. You're kinda smokin' hot you know," I teased, giving her side a tickle.

"Matty! Nooo! I'm too broke and tired," she giggled.

Playfully swatting my leg, Amy readjusted her pillow and then settled back down.

"Do you really think that, or are you just saying it?" Amy asked quietly.

"What?" I countered distractedly.

"You know. That I'm...hot?" she asked hesitantly.

"I really meant it. If you weren't my sister...well, anyway," I replied, hoping my answer wasn't too much.

Although my sister remained mute, I could feel a little, excited tremor.

"Are you smiling?" I asked coyly, waiting motionless for her answer.

"Maybe. If I tell, will you keep rubbing my back?" she countered playfully.

"Maybe. It depends on the answer," I retorted, using exactly the same tone..

Drawing her hair back behind her ear, Amy revealed a beaming, toothy smile. Acknowledging Amy's confirmation with a toothy grin of my own, I resumed.

"Could you rub my lower back please? Right there. That feels so good," Amy sighed.

Another few minutes passed when she asked, "Matty, what part of my body is your favorite?"

"Well, I guess I'd say your butt. Why?" I asked, my heart pounding loudly.

"You didn't seem to want to look for very long before, that's all," Amy replied.

"I would have looked all day if you'd let me. I just thought you were...pissed off," I chuckled.

"I was...sort of. But, not at you. At Jessica. You know, if you want, I could let you look now? I don't mind. Really," she suggested, twisting round to look in my eyes.

Surveying my demeanor, Amy grinned and confidently wriggled out of her pajama bottoms.

The irony of this turn of events was only magnified by the ache radiating below my waist.

"Do you still want me to rub your back?" I asked, smiling my approval.

"What do you think?" Amy countered, settling back to her original position.

My hand traced orbits of her back, gently caressing skin and muscle through the fabric of her t-shirt.

"Matty, could you rub a little lower? Further down...lower...lower...there! Stop," Amy instructed.

Her directions had guided my hand to the small of her back.

"That's the spot. Just rub all around there please," she said.

"Pull your t-shirt up. It's getting in the way," I insisted, my hand continually catching the hem.

"Why don't I just take it off?" Amy offered.

"That would work too," I replied, nodding my approval.

Eyes sparkling, Amy peeled off her t-shirt and unhooked her bra without hesitation.

Giving me a naughty look, she flicked her hair forward, then over her head and settled back down on her belly.

"Okay. I'm ready. Remember where you were? Mmm-hmm, that's the spot," she sighed dreamily.

Amy and I remained silent, content to just enjoy our little arrangement for the next five minutes.

"So, is this still part of the dare?" I asked.

"Sort of. Do you really care?" she countered.

A single stroke brushing just shy of Amy's butt-crack brought about a subtle move of her hips closer.

"No. I'm just wondered if you have to tell Jessica?" I answered.

Smoothing my fingers down her spine, pressing their tips in to her the crease of her butt, produced a tremble from Amy.

"I don't think she needs to know," she replied, heaving a soft sigh.

Using the lightest touch, and obscured from view by the pillow, Amy drew tiny circles with her finger on my thigh.

Plying the relaxed muscles of Amy's butt, my middle finger's tip seemed to be finding itself deeper in the fleshy valley between.

"Matty. I've got an itch just by your finger. Could you scratch it for me?" Amy asked, sounding a little husky.

"I don't have any nails," I replied, a little husky myself.

"Could you just try rubbing it anyway? It's down a little more," she pleaded softly.

"You tell me when I'm on it," I replied.

Resting my hand on the small of her back, I draped my fingers over the rise of her cheeks.

"Okay. It's sort of...sort of in my butt-crack. Just rub along it. Yeah, just like that," Amy directed.

Massaging my middle finger in to her meaty groove, I felt little hip-flexes meeting my stroke.

"Matty, you're so close. Just a little more...a little more...oh...oh," she breathed.

My fingertip finding roughened skin continued forward seeking Amy's knotted opening.

Her hand had long ago discretely snaked beneath her hips to do her lustful bidding.

"Just a little more...please. You know what I...Yes! Yes! Matty, I'm..." Amy bit off abruptly, her orgasm ripping through her soul, as I gently played with her butthole.

Filled with an overwhelming sense of accomplishment, I consider how greatly reality overshadowed cinematic experience.

Amy rolled around holding on to my thigh giddy and breathless.

"I think I got it," I chuckled.

"I think you did too," she agreed, smiling before hiding her face in the pillow.

"I can't believe I just did that. I really need the bathroom," she said shaking her head.

"Technically, we did that," I corrected.

"Yes, we did," Amy agreed, kneeling on the couch and giving me a kiss on the cheek.

Adjourning to the bathroom flushed, Amy left me alone with my thoughts.

"Ames. Can I ask you a question?" I asked as she reappeared looking very happy.

"Okay. What?" Amy replied.

"Have you ever shaved your...down there?" I asked nodding at her downy mound.

"You mean my pussy? Yes, I have. I normally get it waxed off. I've been waiting until the hairs are long enough to get it done again. Oh, and when I have some money," she explained with a half laugh.

"I see," I said.

"Why? Do you like the little girl look?" Amy asked, sitting back down on the couch, feet tucked under her.

"I wouldn't call it that, but I do think it's sexy," I answered.

"Tell me, what do you think guys should do with their junk?" I asked.

"I like shaved and trimmed. Why? What do you do?" Amy countered very interested.

"I trim...but I'm thinking of going to town," I answered.

"You should do it...not that I'll see it," she encouraged.

Bouncing up to her knees with a wicked little smirk and widened eyes, Amy took an excited breath.

"I dare you to let me shave you," she said enthusiastically.

"I thought dares were you and Jess's thing? Besides, why would I trust you with a razor blade down there?" I challenged.

"Oh, come on Matty. It would be so much fun. You can trust me. I've shaved myself lots of times," Amy said in an effort to sway me.

"I don't know. You're pretty tired. What if you fell asleep? I could lose a few inches," I baited playfully.

"Come on. You can dare me to do something," she offered holding her breath.

Pretending that I had been persuaded by her brilliant negotiating skills, I replied, "Okay...but only if you send me a copy of that video you sent Jessica?"

"Only if I can record me shaving you," Amy countered.

"Will you show it to Jessica?" I asked.

"Only if you say I can," she replied after a moment of consideration.

"Deal," I agreed smiling.

"Yes! Yes! Yes! Yes! This is going to be awesome!" Amy yelped giving me another kiss on the cheek.

"Wait here, I'll take care of everything," she said.

Making a b-line for the bathroom, Amy hastily assembled a selection of essential items including my very expensive razor.

"My razor?" I asked.

"I always use your razor. It's really good," she replied knowing that fact would bite.

"Okay Matty. Strip," Amy said eyes sparkling.

Having anticipated this moment all evening, I confidently stood and first removed my t-shirt and then both my boxers and sweatpants together.

Knowing Amy was somewhat already impressed by my manhood helped calm my nerves but not quash them completely.

Kneeling on a cushion, Amy methodically laid a folded towel on the lounge chair, arranged a bowl of hot water, a face washer, a pair of scissors, shaving cream and my razor on another towel beside her.

"Okay Matty. Get your cute butt over here and sit," she instructed.

"Okay. I need you to spread your legs apart as wide as you can. That's good. Perfect," Amy said, as I splayed myself before her.

"Does it feel weird?" she giggled.

"Having my sister shave my balls? Of course not," I replied sarcastically.

"Well, I think your penis is beautiful. The rest of you isn't bad either," Amy said, trying to keep a straight face.

"Nice. I bet you say that to all the guys," I joked, a few nerves creeping in.

"No, just you. Let's get this party started," she giggled picking up the scissors.

"I think I should record this on my iPhone. We can swap later," I suggested.

"You don't trust me? That's fine. Don't blame me if I take a little off the top," Amy jested.

"Don't even joke about that," I replied ready with my phone.

"Okay. My sister Amy has just dared me to let her give me a haircut like a porn-star...down there," I said panning the phone to my genitals.

"So, I think I'm going to call this dare the "Porn Haircut". Okay Ames, game on," I announced in to iris.

Turning the phone around, I perfectly framed Amy as she went to work with the scissors.

I feared for my erection at first, trying to help keep it from harm's way only to have Amy shoo my hand away.

Clear-felling my forest seemed like a marathon at first, but Amy's diligence reaped surprising rewards. Dusting away the trimmings revealed a neat crew cut all over, ready for shaving.

A layer of foam slathered about my groin signaled the arrival of the razor.

Broad swathes of clean skin emerged as Amy systematically raked away the foam.

"You look bigger. Much bigger. Guess that's why guys do it," she remarked, concentrating intensely.

"I thought it was just the camera adding ten pounds," I quipped back.

"Don't make me laugh. I might circumcise you again," Amy warned chuckling.

I twitched at every touch, making the dare an exercise in both pleasure and pain.

Amy cunningly stroked my shaft whenever she had to move it aside, guaranteeing its rigidity.

"Please be gentle with my balls. They're really sore," I cautioned, anticipating her next area of interest.

"Matty. Playing a little one on one? Did I have anything to do with it?" she asked teasingly.

"No. I just got a little carried away," I lied.

"Aww, poor Matty. Well, I'll be gentle. Pity you won't be able to try out your new style tonight," she said sympathetically.

"Yeah, it is. But there's always tomorrow," I suggested, hoping Amy would bite.

Amy just shrugged and continued gingerly running the razor over my scrotum leaving it hairless. "Okay. You have to turn around and kneel up on the arm chair," she directed.

"What?" I exclaimed, completely taken aback.

NeverSmart
NeverSmart
154 Followers