Dare

"If I'm going to do your butt-crack, you have to turn around. If you get up on the arms, I can get at everything," Amy explained.

Remember the video of Jessica's waxing, and that she had posed similarly to get up and under, I didn't fight her request.

"Okay. You're the boss," I said, dutifully scaling the chair.

The suggested pose felt ridiculous and completely submissive, but it did provide the access required.

"Have you ever stuck your finger in a girl's butt before?" Amy asked, as she applied some more shaving cream.

Enjoying the pleasant feeling of Amy's fingers across my own opening, I answered, "Once, with Paula."

"Did you she let you put anything else in there?" she asked casually, picking up the razor again.

"Paula was kind of okay with a finger, but she told me there was no way I was putting my dick in her ass," I replied, remembering Paula's words as if they were said yesterday.

Amy didn't comment on my answer other than a non-committal grunt.

A brief silence followed before Amy asked, "Did Paula put a finger in yours?"

"Paula wouldn't go there...but I would've liked to try it," I replied, surprised that I had admitted my secret desire.

Wanting to shift the spotlight off me, I asked, "Have you let a guy put his dick in your butt?"

"Not yet," Amy replied, running the razor one last time deftly between my cheeks.

"And, you're done. Hold on a sec. I want to put some cream to help stop irritation and ingrown hairs," she said.

Smoothing on the cream was deliciously sensual, the cool contact teasing my newly exposed skin.

"Ames, you are evil. Do you know how hard you are making this?" I questioned, trying to hold my iPhone steady.

"About as hard as you made my back rub, I hope," Amy replied, taking the phone.

"Oh, look at your cute butthole. Makes me want to put a finger in it," she teased.

"Maybe some other time. So, let's have a look," I said.

Climbing back down sent a cool flood of air between my thighs, accenting the skin's amplified sensitivity.

"H'oh. That feels nice. And so smooth! It's really sensitive. This rocks!" I exclaimed.

"You're welcome," Amy said, capturing a few last frames before pressing stop.

Dividing the clean up, Amy headed to the bathroom, while I dropped the wet towels and face washer in the laundry.

"Thanks for letting me shave you. It was so much fun. Didn't imagine ever doing that to a guy. Least of all you," Amy said.

"Yeah, didn't see that one coming. Strange, but I'm okay with it," I admitted.

"Me too. Come on. Let's download the videos and have a look," Amy suggested fighting back a yawn.

"Okay, but I'm seriously tired. You must be wiped?" I said.

"I could stay up a little longer," Amy smiled, holding a fist over her mouth, trying to swallow another yawn.

"You're toast and I'm not much better. Let's do the videos in the morning," I suggested.

"Oh, alright. I guess I can wait. Just don't wake me up this time, okay?" Amy warned.

"I'm working from home, so I don't have to get up either. And that was your alarm," I defended.

Giving each other playfully rueful glares, we each collected our clothes and headed for bed.

~~~~

Contrary to my expectations, I had little trouble falling in to a peaceful slumber.

The sounds of kitchenware hitting the stove top rudely snapped me awake.

Even half asleep, my subconscious sent a hand down my pants to do an assessment of my wellbeing after yesterday's thrashing.

"Game on," I smirked sleepily, throwing the covers aside.

Padding my way to the kitchen, I marveled at how different being shaved made everything feel.

"Hi Matty! Did I wake you? Sorry about that. How did you sleep? I slept like a log," Amy bubbled, her eyes suggesting it was no accident I was awake.

"Morning. Yeah, me too," I replied, her spritely greeting bringing me out of my sleepy stupor.

Opening the fridge, I pawed around in the pizza box for the breakfast of college students.

Dragging two slices out on to a plate, I took my usual spot at the kitchen bench.

"What time did you get up?" I asked.

"About an hour ago. I've been waiting for you. I have a surprise," Amy said.

Looking mischievous, she produced both of our iPhones and pushed them in to middle of the bench.

"What is this?" I asked slowly.

"Well, I had an idea. You don't want Jessica to see your dare, because you don't want her to see you naked, right?" Amy stated.

I nodded.

"What if you saw her naked first? Would you let me send it to her then?" she asked, looking slightly anxious.

"I guess that would change things. But, I'm also worried she would show it round," I said tentatively, fighting to mask my excitement.

"What if I told you that Jessica sent me a video of her naked, for you to watch first, and that I guarantee she will not show anyone else," Amy said, using bold hand gestures to sell her pitch.

"I'd say, okay," I answered.

"Hit play," she said simply.

Finishing the crust of the first piece of pizza, I wiped my hands on my pajama pants and then picked up Amy's phone.

"Go ahead," Amy reassured me.

Feeling my skin tingle, I raised a finger to the iPhone's screen and tapped.

"Hi Matty. How are YOU this morning? Amy said you guys had an interesting evening...but I can't see," Jessica said, putting on a sad face.

"So, Amy came up with the idea to dare me to take a shower with my iPhone," Jessica said playfully.

The image jerked about for a moment and then steadied showing Jessica, clutching a towel about her breasts, and holding her iPhone in the reflection of a large bathroom mirror.

"We thought we would call this dare the "Shower-cam Dare"," Jessica said proudly.

"The plan is I'm going to put my phone in a zip-lock bag and tape it to the shower wall. It was Amy's idea. Your sister is really clever," Jessica grinned.

"But, just in case you can't see, here's a sneak peek," she said winking.

Opening her hand Jessica let the towel fall away leaving her standing there naked.

"Ta-da!" Jessica exclaimed.

"She sent you a copy too. So, what do you say?" Amy asked, standing on tiptoes, holding her breath.

Watching Jessica climb in to the shower and play up to the camera soaping up her breasts, I nodded smiling.

"I knew it! I knew I could convince you," she whooped.

Picking up my own phone and entering the password, I found two emails waiting for me. There was one from Amy and one from Jessica.

Not bothering to open their emails, I sent an email to both girls with the "Porn-star Haircut" file attached.

Moments later, Amy's iPhone chirped and buzzed the email's arrival.

"Thanks Matty," Amy said happily.

"You're welcome," I replied.

"Well, I better get started on some work. I'm sure you and Jessica will have a lot to talk about," I said.

"You have no idea," she answered.

IPhones in hand, Amy and I walked together down the hallway before I peeled off to enter my bedroom.

~~~~

After a quick shower and a fresh set of clothes, I sat staring at my computer perplexed by a firmware bug.

A surprisingly loud growl from within, alerted me to the fact that nearly three hours had passed.

While trying to remember what might be on offer to quell my hunger, Amy materialized at my door.

"Hello Ames. What can I do for you?" I asked.

"Hi Matty. I'm going to head out for a little and guess what? I need to borrow some money," Amy replied.

"Really? How much this time?" I asked, turning to give her my full attention.

"Just sixty dollars," Amy replied, smiling demurely.

"I thought this might happen, so I thought of a dare for you if you asked again," I said.

The sexual tension between the two of us sky-rocketed instantly.

"What do you want? I'll do anything," Amy repeated the answer she gave just hours ago, verbatim.

"I have a few things to do first, but I'll be ready by the time you get back," I said.

Pulling three twenty dollar notes from my wallet, I placed them in her open palm.

"Works for me. I'll see you later," Amy said.

"Oh, Ames. I found this. I think it's yours," I said.

Opening my desk draw, I scooped up Amy's favorite hairbrush and tossed it to her.

"Don't know what it was doing in there," I said innocently.

Catching the brush, I could see her debating whether to pursue the subject, or leave a sleeping dog.

"Hey, thanks. I've been looking for this. It's my favorite. I love the handle," Amy said.

"It looks like great brush," I said.

"It is. You should try it. Maybe I could use it on you later?" Amy suggested.

"Maybe. Anyway, you should get going," I advised.

"Yeah, I should. See ya later, Matty," Amy smirked.

"Bye Ames," I grinned back.

Convinced she had left I picked up my iPhone and began constructing the foundation of my dare.

~~~

Hearing Amy pull in to the driveway, I felt confident that my preparations were complete.

"Hi Matty. I'm home," Amy called out.

"Hi Ames. I'm in the kitchen. What have you been up to?" I asked.

"Wouldn't you like to know? Nah, I'll tell you. I picked up a few groceries and...something for me," she said.

"What's in the bag?" I asked.

"Just some stuff for a salad. Tomatoes, lettuce, cucumber and carrots," Amy replied nonchalantly.

Amy innocently bent at the waist to restock the crisper draws, but from my angle, it seemed like she was taunting me.

"So, are you going to tell me what the dare is?" she asked.

"Yes, I am. It's pretty simple. I'm calling it, the "Phone Call" dare," I said.

"Next time you get a call from Jess, while you are on the phone, you have to let me do anything I want to you. You can't hang up until she does and you have to try to keep her talking for as long as possible. Sound okay?" I asked.

"Oh, and you can't tell Jessica what the dare is unless she asks," I added.

"Okay. But, we don't usually talk on the phone," Amy said, wearing a quietly, excited smile.

"I think Jess might call. I have a feeling," I replied.

"I see. Do I have time for a shower?" she asked with controlled excitement.

"I think so," I answered.

"Good, because that's what I'm going to do," Amy said.

Whirling on the spot, she looked back one last time and then casually walked off toward her bedroom.

Watching the clock, I firmly believed the only reason Amy's shower ended was due to a lack of hot water.

Estimating that Amy would now be dry and dressed, I dispatched the message I had been waiting to send all day.

"Ames. Could you come to my room please?" I asked, from her bedroom doorway.

"Okay. Should I bring my iPhone?" she countered, grinning with nervous excitement.

"I think you should," I replied, grinning back.

Phone in hand, Amy escorted me to my bedroom.

"You've been busy," Amy said, looking around my room with wide eyes.

"Uh-huh. I hope you don't mind? I borrowed your iPad," I said.

While Amy had been out, I had converted my bedroom in to an amateur video studio.

The process had been relatively simple. Borrowing my parents' bedside lamps, I had managed to balance the room's lighting, trying to avoid the pitfall of shaded action that most amateur videos suffer.

Finding the cameras' locations and foci, to maximize the playback potential, was the most time consuming task. Eventually, I settled for my laptop angled off to one side of my bed, one iPad looking up the length of my bed on a chair and the second iPad hanging on the wall, looking down my bed.

"I don't mind at all, but don't you think you had enough already?" she asked smirking coyly, still looking around the room.

"We're meant to record the dare, right? I'm just making sure we don't miss anything," I answered.

Amy, hearing my explanation, just gave a casual, knowing smile. However, it was easy to sense her excitement just below the surface.

"Why don't we do an intro? You can use my iPhone. Just give me a sec," I suggested.

Making my way around the room, I set my laptop and the two iPads recording and then held my iPhone up at Amy.

"Are you ready?" I asked her.

"I'm ready," she replied.

"Okay. Go," I said.

"Hi. So, my brother Matty has dared me to let him do whatever he likes to me while I'm talking on the phone to Jessica," Amy explained wearing a grin.

"Also, I can't hang up or tell Jessica anything unless she asks specifically. Have I got that right Matty?" she asked playfully.

Amy had barely finished her question when her iPhone chimed.

"Hi Jessica. This is a surprise," she said sarcastically, putting the call to speaker phone.

"Hi Amy. Yeah, well, I was bored so I thought I'd give you a call," Jessica replied.

Positioning my iPhone on a shelf, I skirted behind Amy and paused nervously before slipping my arms about her waist, while the girls continue to talk.

Delicately relinquishing Amy of her phone, I placed it on my desk and then moved her so we were both well framed in the laptop's screen.

Amy struggled to stifle a giggle, as my hands cupped her breasts through her t-shirt for the first time.

"Did you forget your underwear?" I whispered in her ear.

"I didn't forget anything," Amy replied whispering back.

"What did you say Amy?" Jessica asked abruptly.

"Oh, nothing. Matty just asked me something," she replied.

"So, what's going on there? Matty sent me a message to call you and keep you talking. He said he had a surprise for you," Jessica asked.

Giving me an incredulous look, Amy answered, "Oh, he did did he?"

"Can I tell her now?" Amy asked, as I let my hand fall away.

"Tell me what? Tell me what?" Jessica pleaded.

I grinned and nodding replied, "Go ahead."

"It's a dare Jessica. Matty dared me to let him...wait a sec," Amy giggled as I pulled her t-shirt up.

Slipping the t-shirt over head, I spun Amy around to face the desk.

"As I was saying, Matty dared me to let him do whatever he wants while I'm on the phone to you and I can't hang up," she finished.

"I knew it! What's he done so far?" Jessica asked.

"Not much...but he just took my t-shirt off. I can't see what he's up to at the...oh, my God. He's naked. Jessica, his dick looks huge!" Amy replied.

"What are you wearing?" Jessica asked.

"Just a cute pair of shorts, but he's got his hands on my hips. Jessica, I can feel his dick in my butt-crack. Matty, you are so bad," Amy said, pushing firmly back to meet me.

With her hands on my desk, I tugged Amy's shorts to her ankles, letting her finish by kicking them aside.

Amy smelled like candy and with Jessica's inclusion, I abandoned my earlier restraint taking Amy's breasts in my hands.

"Oh, Jessica. He's pulling my nipples. His hands are so warm. Yes, Matty. Pinch them harder," Amy sighed, her hand finding my shaft.

"This is so hot! Amy you have to tell me everything," Jessica demanded.

"His dick's so smooth. It's like baby's skin. I love it! I can't believe I'm jerking Matty off!" Amy exclaimed.

Continuing to play with one breast, I trailed a hand down Amy's belly and then, with my heart thumping in my ears, on to her mound.

"Do you like it Matty? Feels nice, huh?" Amy whispered.

To my surprise, I felt no hair. Running my fingertips back and forth over her clean skin was intoxicating.

"I got everything waxed especially for you," she breathed.

"It's amazing. So, smooth and soft," I replied in to her ear.

"Uh-huh. I feel so sexy. I love it!" Amy exclaimed softly.

"Hey guys. Third party here. I'll hang up," Jessica threatened playfully.

"Chill Jessica. Matty just said he likes my freshly waxed pussy, that's all," Amy placated.

"I bet he does. You should thank me Matty. I dared her to do it," Jessica said proudly.

"Thank you Jess," I called out over Amy's shoulder.

Reaching lower, my fingers found Amy's inner thighs already slick and wet.

Discovering her clit made Amy tense, her grip tightening around my shaft, as she sighed loudly.

"I think I just found Ames' clit Jess," I announced.

"Sounds like it to me," Jessica replied.

"Oh, fuck Jessica. He's fingering me. He's fingering me. It feels so fucking good," Amy moaned, her face flushed and her breathing a little ragged.

With my nostrils filled with Amy's musk, I turned her round, wanting to take in her every expression. We both looked down each other's bodies hungrily.

Locking eyes, we grinned at each other knowingly, touching our foreheads together.

"What's happening? This sooo sucks. You guys have to let me see. Turn on the video," Jessica complained, as Amy's iPhone screen lit up with Jessica's animated face, bursting our little bubble.

Pressing the mute button on her phone, Amy and I burst out laughing. While Amy draped her arms around my neck, I ran my hands down her back until my hands each grasped a butt-cheek.

Pulling one cheek aside, I made a surprising discovery.

"Is that? Did you?" I stuttered, circling my finger around her anus.

There was no mistaking the frictionless, viscous nature of what Amy had done.

"Did I lube my butt up? Yes, I did Matty. You said anything, so I'm ready for anything," she smirked proudly.

My dick twitched against Amy's belly, leaving a snail trail of pre-cum.

"Guys? Are you there? Come on. I know. I dare you BOTH to let me watch," Jessica said triumphantly.

"Oops. Yeah, we're here. You know I won't say no. Matty?" Amy said, after hastily hitting the mute button to reinstate the audio.

"Would you owe me a no holds barred dare, Jess?" I asked.

"Of course, Matty," Jessica's image replied eagerly.

"Alright," I agreed and activated Amy's phone's video.

Jessica's look of desperation turned instantly to elation, her screen obviously displaying our current embrace.

"Thank you, thank you, thank you, thank you!" Jessica repeated.

"What do you want to do now Matty?" Amy asked smolderingly.

Without a word, I took Amy's hand and walked her over to the bed. Taking my lead, Amy climbed on to the bed and struck the very same wanton pose her drunken self had while I had filmed her.

Giving a slight shake of my head, Amy turned to lie on her back and raised an eyebrow, waiting for my approval.

Barely able to contain my excitement, I moved between Amy's legs, Amy parting them welcomingly.

Neither of us could stop smiling as I hovered tantalizingly short of what we both knew to be the point of no return.

"Don't tease me," Amy said playfully, writhing a little in anticipation.

Taking a silent breath, I nervously tilted my hips, looked in to Amy's eyes and eased forward.

"Ohhh," was all Amy quietly moaned, as she closed her eyes and thrust her hips out.

Everything seemed to tingle like I'd never experienced before. Perhaps my recent drought sex-wise had created the starving man effect; anything would taste fantastic. But, the root cause was more likely the fact that this was an extraordinary event.

Overwhelmed, I stupidly blurted, "Ames, we're having sex."

"I know," Amy replied, answering in the same awestruck manner.

Grinning wildly, we ground our way in to a deep thrusting rhythm. Amy ran her fingers through my hair, then down my back until they found my butt and groped hard.

Scooping up Amy's leg and pinning it back with my shoulder left my hand free to slip a finger in to her already slick rectum.

"Yes. Finger my ass," Amy cooed.

"Finger mine," I breathed back.

Stopping to smirk, she leaned a little to one side, enough to allow her fingertips to seek out my clenched opening and test its integrity.

"You lubed?" Amy gasped with delighted surprise.

"I wanted to be ready for anything too," I replied, grinning devilishly. Together, with fingers pumping in and out, we quickly built up ahead of steam.