Dare

I scanned the following line and again the word "dare" was listed.

I reviewed the full title and it became apparent, that there was a directory folder named "Dare" and that the folder contained multiple video files with the word "carrot" in the file name.

My heart pounded and a grin lit my face.

I knew I couldn't open the files on Amy's laptop without leaving a digital footprint, but I could copy them off it.

My memory stick chimed its arrival through the laptop's speakers and prompted a new window showing the drive's location relative to the overall hierarchy.

It was a simple act of dragging the "Dare" folder over my rogue drive's location to start the download.

Satisfied that all was as it should be, a wave of calm released all the tension that I had pent up.

I had only expected the job to take a few minutes, but the status animation showed that the copying was nowhere near complete.

Patience regarding computers, and there intrinsic need to try people's, had come naturally to me. Rarely did I doubt my laptop's ability to win out if given time.

However, this was Amy's chew toy and I had little confidence as to its nature.

Ten minutes passed and admittedly the estimated time of the operation was nearing zero.

Relief washed over me when the status window abruptly disappeared.

Amy's laptop looked none the wiser for my illicit scavenging by the time I disconnected my drive.

"Let's see what we have here," I said, feeding the memory stick in to a waiting port in my own laptop.

"Holy shit," I breathed in awe.

Displayed on my screen were some thirty odd video files, each one with either "Amy" or "Jess" headlining the file names.

A quick glance down the list enlightened me as to the naming convention employed to the files.

Following the "Amy" or "Jess" component of the file name was a noun like, for instance "Carrot", but always the word "Dare" followed after.

A typical file name would be "Amy-Carrot Dare" or "Jess-Zucchini Dare".

If sorted alphabetically, the files starting with "Amy" equaled in number to the "Jess" ones.

If listed chronologically, it became obvious that the files were generated using a simple pattern. An "Amy" file, and then a "Jess" file repeating over and over.

The creation dates indicated that initially the files were generated in pairs spaced a week apart, but that the rhythm changed to just one file a week and finally to seemingly random intervals.

In the later files, I noticed the names more often than not had one of two endings, "Greek" or "Uncle".

An overwhelming sense of excitement had me buzzing on the edge of my seat.

Ready to dive in to the mix, a small pang of guilt halted me.

If I opened just one file, I would have to live with the fact that I had totally betrayed an unwritten law that Amy and I had forged over the years.

Suddenly, the thought of breaking that trust weighed heavily on my conscience, but an instant later that all changed.

"What the fuck?" I frowned.

There, in amongst the various titles was my name, not once, but four times.

My concern for maintaining my sibling integrity vanished as I targeted the file named "Amy-Matt-cam Dare" and opened it.

"Oh my God. I can't believe this," I heard Jessica say excitedly, as the picture panned savagely around Amy's bedroom before steadying on Amy.

"Hurry Amy," Jessica pleaded.

"If you'd shut up, I'd be done already," Amy replied.

"Okay, okay. Just go," Jessica's voice urged.

Framing Amy's face to the left of shot, Jessica was taking clean video of me sitting at my desk, naked, on Amy's laptop screen.

"Okay. This is the Matt-cam dare," Amy announced.

"Right now, my brother Matty is in his bedroom, jerking off to porn and we have a live Skype connection to my iPhone which Jessica dared me to put in Matty's room," she explained.

"I didn't think we'd catch him jacking off," Jessica exclaimed, moving what must have been her iPhone, closer to the screen.

"This is so awesome!" Amy declared.

"He's got a pretty big dick," Jessica said, pointing a finger at the screen.

"Yeah, but we thought it was last time we saw it," Amy stated knowingly.

"That was a fun dare too, but this one severely rocks," Jessica's voice bellowed as if over a PA.

I sat mortified. Last time they saw it.

Then I smiled.

Did I really care that my sister and her best friend witnessed me doing my favorite hobby? No, not really. The more I watched and listened to the girls' commentary, the more confident I felt.

Far from embarrassing, the experience was proving to be a bit of an ego boost.

"Wonder what he's looking at?" Jessica thought out loud.

"Well, it could be something from his anal collection. Or maybe the lesbian stuff," Amy offered.

"I bet it's the "other" folder. It feels like that sort of night," Jessica giggled.

Abruptly, Jessica's face flashed in to view.

"Oh, Matty. If you only knew how you inspired us. Well, your choice in porn did," she said theatrically as I heard Amy burst out laughing.

I was confused.

"How the fuck did they get to my porn?" I asked myself.

I prided myself on how well defended my laptop's contents were, so what I had just heard was a resounding slap in the face.

Terminating the playback, I found the file named "Amy-Matt's Porn" and clicked it to life.

Amy's face filled the screen.

"Go? Okay. So, the devious Jessica has just dared me to try and find my brother Matty's porn stash," Amy said.

"He's a guy so, he's going to have porn," she concluded, walking the hallway to my bedroom.

The next few minutes were of Amy doing a cursory search of my room, admitting that she doubted I would have any hardcopy.

"What's the plan now Sherlock?" I heard Jessica say.

"Well, Matty is paranoid about his precious laptop so, I'm not getting in there," Amy stated putting a grin on my face.

"Buuut...he doesn't lock his external drive away," she sang, in a mocking voice.

Even though I was viewing the past and the damage was done, my first impulse was to reach for the drive.

"It's already too late dingus," I reminded myself, feeling completely duped.

"Okay. Where to next?" I pondered, trying to shake off the fact that I'd been a joke for well over two months.

"I guess I'll start at the start. Let's see what "Amy-Chili Dare" is," I said clicking on the file.

The content was funny, but not what I thought it would be. As was customary, there was a brief intro featuring Amy, but the dare was just that Amy had to eat a hot chili. It was hilarious watching her face turn crimson and the desperate panic that ensued, but it was very vanilla.

"Let's try..."Jess-Wasabi Dare"," I said.

When the screen filled, it was Jessica's smiling face that popped up.

"Okay thrill-seekers. The lovely Amy has just dared me to eat this ball of wasabi that came with our Japanese take out," Jessica said, holding up a sizable ball of green Wasabi paste.

In less than a minute, tears streaked her cheeks and mucus ran freely from her nose. I laughed along with Amy while Jessica suffered.

The scene ended with Jessica mopping up the secretions from her puffy, flushed face, both girls laughing and chattering.

Thoroughly over my initial skepticism, I made a short visit to the kitchen and returned with snacks, prepared to continue the entertainment.

Taking a bite of my own signature sandwich, I queued up the next two files; "Amy-Banana Dare" and "Jess-Hot Dog Dare".

Viewing these two dares gave me an insight regarding both girls' abilities in the oral sex department.

Their attempts to deep throat the phallic stand-ins prompted me to do a mental comparison of my own experiences and I drew the conclusion that they had obviously had very happy boyfriends.

The light-hearted, relatively tame opening dares soon developed a more adult and definitely sexual flavor.

I spent two and a half hours watching Amy and Jessica trade dare after dare, Jessica exploiting Amy and then Amy commanding one better of Jessica.

I could see the brilliance of forethought to record their dares. They really made for great viewing.

I had also come to understand that there was an unwritten law that no dare would be repeated.

Having reached what I regarded as a milestone, namely the raid on my porn fortress, I took a moment to do mental review.

I now knew first hand that Amy had purposefully attended a gym wearing fully camel-toed tights, enjoyed having ice cubes stiffen her nipples and clit, had stuck half sucked Altoid mints in her ass and her puss because it had been in Cosmo , and was adept at shaving off every pubic hair below her waist.

I also knew that Jessica had gone dancing in a very short dress sans underwear, loved the sensation of hot wax dripping on her breast and butt, was able to cum with clothes pegs on her nipples, and had a Brazilian wax while being videoed.

"This is fucking awesome!" I laughed out loud.

The house phone rang out from the kitchen.

"Hello," I said, in to the handset having tracked it down.

"Hi Matthew," I heard my mother replied.

"Hi Mom. How's Aunt Lisa?" I asked dutifully.

"Oh, she's fine. How are you and Amy? I tried calling Amy, but she's not answering," she asked.

"Amy's at work. Do you want me to pass on a message?" I replied.

"I just wanted to tell you both that I'm going to stay a few more days," she informed me.

"Lisa could use a little help with the kids over the school break," mom explained.

"Okay Mom. I'll tell Amy when she gets home," I assured her.

"Call me if you need to otherwise, I'll see you Wednesday," she advised.

"Will do. Bye Mom," I replied.

"Bye sweetheart," mom said, before hanging up.

Pressing the off button, I left the phone on the kitchen bench and scrambled playfully back to my bedroom.

Dropping heavily in to my chair, I took a deep breath and stared hard at the next two files.

Ignoring the "Jess-Zucchini Dare", I hovered over the "Amy-Carrot Dare".

"Okay, "Amy-Carrot Dare". I hope you are what I think you are," I muttered under my breath.

The split second delay between mouse click and execution seemed abnormally long before the playback started.

"Are you ready?" I heard Amy ask, as the familiar shaky second or two of camerawork steadied.

"Yep," Jessica answered.

"Welcome to dare of the week. This week, the naughty Jessica has dared me to masturbate with the largest carrot we could find at the supermarket," Amy bubbled.

"So, this is what we found in the organic produce section," Amy said, holding up an unusually large carrot.

"Okay. Quick side note. The idea for this dare came from my brother Matty's porn collection," Amy added grinning.

"Yeah, thanks Matty!" Jessica called out off screen.

"I guess I had better get comfortable. Don't need these," Amy said, taking off her jeans and underwear.

"Should I take everything off?" Amy asked Jessica.

"Definitely," Jessica replied confidently.

"Alright. Okay. So, I'm pretty wet, but this orange guy's huge," Amy said, shedding her t-shirt and bra.

"We talked about this and I'm going to try without lube and use saliva," she surmised.

"Buuut... if things don't go so smoothly, we have a plan B. A tube of KY that got us some strange looks," Amy giggled, producing the tube from a plastic bag.

"Oh, we were so totally busted," Jessica chuckled.

"I think we are ready. I'll just get comfortable on my bed here and..." Amy paused.

With a pillow behind her back, Amy sat slouched against the wall and proceeded to dip the carrot tip gingerly in and out of her pussy.

"It's cold. I've got goose-bumps," she stopped and pointed to her arm.

"You've got a lot more to go," Jessica voice reminded.

"Wow. Pushy thing ain't cha? Want some?" Amy joked, holding the tip out towards the phone.

"After you," Jessica quipped back.

"I'm a little dry. Hold on," Amy said and promptly sucked on the carrot, leaving a trail of saliva.

Amy escalated her efforts, moving from an exploration to an assault, pushing the carrot deeper with each stroke.

"Who's a slut? Come on Amy. Only, like, five inches to go!" Jessica barracked, as the carrot disappeared.

"I need the lube," Amy said abruptly and flipped the cap open.

"Fuck. It's got that frigging silver thing," she swore, completely frustrated.

Jessica cackled in the background and then moved in closer.

"Fucking finally," Amy announced, throwing the seal away, looking more than flustered.

Holding the carrot skyward, Amy blanketed the tip with a long, spiraled slug of the clear gel.

Liberally slicking the colorful produce, Amy exposed her gaping entry and drove the carrot home.

"Fuck, that stuff's good," Amy gasped, unexpectedly burying over three quarters of it in.

"Holy shit! That's like eight inches! Can you take it all?" Jessica asked excitedly.

Amy didn't reply, instead she just pushed and pulled the carrot with deliberate strokes.

Wet, lip-smacking sounds, a by-product of Amy's faster, sloppier strokes, signaled her last, big push.

"Fuck...fuck.....I'm cumming....I'm cumming!" Amy wailed, then held her breath and shoved hard.

I came watching my sister's clenched eyes, waiting for her to return.

"Amy! Oh my God. You did it! You did it! Oh my fucking God. How do you feel?" Jessica blurted excitedly.

"Fucked," Amy answered, setting the carrot down, sweat beading her brow.

"I bet. I didn't think you could do it," Jessica remarked.

"Neither did I," Amy replied exhausted, but smiling.

"Spread your legs," Jessica directed.

"Whoa. You look like you sex with a donkey," Jessica chuckled.

"Jessica! That's disgusting. How could you even..." Amy laughed, screwing up her face.

"Turn that off," she demanded playfully and with that, Amy vanished.

I sat breathing heavily, noting that I too was covered in a film of sweat.

The video was off the charts hot, but it was not what was promised.

Deciding it was probably a good opportunity to freshen up, I headed for the shower.

Emerging clean and primed, I grabbed a snack and merrily returned to my desk.

For the next hour and a half, I witnessed a dual of sorts. Amy set Jessica a Corona bottle to conquer. Jessica retaliated with a cucumber for Amy to tackle.

"Jess-Matt Jr Dare" was my unveiling that girls had reference.

Jessica had been given the task by Amy, and had displayed great stealth in removing my duvet, leaving me naked. She had turned the heating up to encourage me to embrace its removal.

"That is just evil," I admired, grinning.

The following dare was definitely straight out of my porn play book.

Jessica had purchased ten sets of Japanese style chopsticks. The dare was for Amy to start by inserting one chopstick, tail-end first, and keep adding chopsticks until she could not.

By the mid-way point, Jessica had to help insert the chopsticks while Amy managed the bundle. After ten minutes, Jessica had no more chopsticks and Amy had them all.

The two endings "Greek" and "Uncle", denoted dares that involved inserting things in to their butt, or both vagina and butt, respectively.

Both girls, it seemed, were somewhat naturals to the world of anal, having applied proven techniques distilled from a mountain of internet research.

Unlike previous dares, Amy and Jessica had discovered that the "Greek" and "Uncle" dares were better tackled by assisting each other.

Quite ingeniously, the darer would sit on a chair or edge of a bed, and hold, for example, a carrot with their knees. Meanwhile, the daree would get down on all fours and back in to said carrot doggie style.

Using this method left the darer's hands free to shoot the actions and still able to lend a hand if needed.

Accomplishing the "Uncle" dares was both entertaining and unbelievably intense to watch.

Jessica had been the first one to try by taking on two carrots simultaneously. It seemed like working out just how to coordinate the whole thing was the hardest part. Once the girls had figured out how, Jessica's body had offered little resistance and within minutes, Amy had captured their first double penetration dare.

Amy's turn at an "Uncle" was much slower going. Jessica had chosen the combination of carrot and cucumber. The video had lasted over fifteen minutes and Amy looked completely spent, physically and emotionally, by the end.

The fourth video to feature my name was a revisit of the "Matt-cam" dare, but this time, Amy had dared Jessica and Jessica had taken it to a whole new level.

Instead of just one iPhone, she had placed both girls' phones in my bedroom, one above my desk and one below, both streaming video to Amy and Jessica's laptops, which were set up side by side on Amy's bed.

We had been given iPads for our birthday and it had been hers that they used to record the dare.

Playing back this file brought a tight feeling in the pit of my stomach. I knew what they had caught me doing.

"You are a genius Jessica. This is awesome," I heard Amy say.

"Does he ever not jerk off?" Jessica asked sarcastically.

"Aww, give him a break. He doesn't have a girlfriend at the moment," Amy defended.

"Why don't you have a go? You fantasize about him enough," Jessica baited.

"Shut up! Like you can talk! You're always talking about fucking him. Why don't you?" Amy chuckled.

"Hey, Amy. What's he got there? Is that a hairbrush?" Jessica asked.

A chill ran down my spine.

"That's my hairbrush! That shit! I've been looking for that for weeks," Amy exclaimed.

"Is it the one with the handle you like?" Jessica asked.

"Yeah. It's perfect for a quick fix. What's he doing with it...Oh, my God. Jessica, are you watching this?" I heard Amy gasp.

"He's sticking it in his butt! Oh, my God. You can see everything from my phone," Jessica said excitedly.

"Aww, my brush," Amy said, sounding dismayed.

"Amy, forget the brush. This is awesome. Your brother is fucking his ass with the handle of a brush," Jessica said, on my screen.

"Come on. You love watching Matty jerk off. Just chill and enjoy," Jessica reasoned.

"You're right, but I still want my brush back," Amy grumbled with a grin.

Knowing the ending, I stopped the playback.

"So much for that secret. Fuuuck!" I groaned slumping back.

"I'm such a chump. Owned completely," I sighed.

A thought crashed in to my head. Did Amy and Jessica show the videos to anyone else?

I never considered publicly displaying the girls' exploits. Would they have the same consideration for me?

My instincts told me to trust their discretion, but I couldn't help feeling a little vulnerable.

By the time six thirty rolled round, I was up to date.

The latest dares had Amy and Jessica trying to fist themselves, Amy through the front door and Jessica through the back.

They were their hottest performances of all, but I had nothing left in the tank and my equipment had taken all the abuse it could for one day.

Standing to stretch my out back, I jumped a little when my phone sprang to life. It was Amy calling.

"Hi Ames," I said.

"Hi Matty. Would you mind picking me up?" Amy asked tentatively.

"Sure. Meet you at the same spot?" I countered.

"You're a life-saver," she said, sounding exhausted.

"Be there soon," I replied, already walking towards the front door.

"Okay, bye," Amy said and then hung up.

Using my locals' knowledge, I cut across the peak-hour traffic and arrived to find Amy waiting.

"Thanks Matty. I've had a shit day. Nothing went right, but at least it's done," Amy said, flopping in to the passenger seat.

"Hey, I'm starving. Do you think we could get a pizza? I've only had a packet of M and M's all day," she asked hopeful.