As we grew up, my big sister and I would always make bets about stupid stuff all the time. She was two years older than me and always underestimated me, so I usually won the bets. But not always. Still, Sis had a tendency to overbet sometimes when she shouldn't.

And so it was that one day she bet me that I couldn't climb to the very top of a very tall tree that was growing outside a drugstore we'd just come out of. "You'll chicken out before you get that high," she insisted.

"No, I won't," I insisted back.

"No way you can do it," she said, smugly, "you'd never make it, not in a million years. If you climb that thing, we'll have to have the fire department come get you down!"

"Oh? Pretty sure of yourself," I said, beginning the usual banter, "aren't you?"

"No," she parried, "I'm pretty sure you're a wimp!"

"Well, if you're so confident, then what will you bet me that I can't do it? Hmm? What do I win if I do?"

"Hah... OK, if I win, you have to clean the kitchen after dinner every night for a week. And if you win, I'll..." She stood thinking for a moment. She knew in her heart that her brother could never make it to the top of that HUGE tree. There was no way! He really was too much of a wimp. And she did think it would be hilarious to film him with her cellphone getting rescued by the fire department. Just what every high school senior needs to ruin his reputation just before school is out, she thought evilly. But to seal the deal, she'd need a really good bet. Something that would throw him off. She knew just what to bet....

"If you win, I'll give you a blowjob!" She smiled smugly at him, raising an eyebrow to see if he would react. Then adding, "of course, I only bet such a thing knowing full well there's no way in hell I'll ever have to do it."

Now, I'm a skilled barterer. I know how to up the ante, and so I knew it was time to double down. "Hah! I thought you were confident," I said with a laugh, "you're betting me one blowjob to a whole week of work? I don't think you're as sure as you claim to be..."

"Fine," she said, "make it one every day for a week IF you win. Which there's no way you will."

"Well, if you're so sure of that, why not make it a year? Hmm? And I'll make it a year of kitchen duty if I lose," I said cockily. "So, what do you say? We got a bet?"

"Yeah," she said, "you're on. Now, go break your neck or something, idiot."

I just smiled and started climbing the tree—all the way to the top. Just like I'd done three nights before to try and get a glimpse of the hot girl from my school who lived in the apartments across the way, at just about that height, while she was changing or something like that. I climbed right up there, and right back down. Like it was nothing. Then I dropped to the concrete right in front of my sister and stood up with a victorious grin!

She stared at me with shock written all over her face. Her mouth hanging open, her pretty eyes open super wide. And then, without a word, she sighed deeply, turned, and began walking dejectedly into the drug store again.

"Hey, what're you doing," I asked as she started toward the store. I'd expected some accolades and the pleasure of having her admit that there was no way in hell she was gonna suck my cock even once, much less three hundred and sixty-five times. Instead, she was zombie-walking into the store again.

"I'll be right back," she said in a vacant tone, "I just need to stock up on toothpaste."

-~-~-

I stood staring at the door like I was a statue decorating the sidewalk until she emerged about twenty minutes later. And sure enough, carrying a bag with an unreasonable number of long, rectangular boxes in it.

"Let's go," she said flatly, looking past rather than at me. I couldn't tell if her attitude was dejection, anger, resignation, or... something else. Among her other strong attributes, she had a winning poker face, and I just couldn't discern what was going on in that pretty head of hers.

We walked in silence for a while towards our apartment building, when I decided to let her off the hook early. The whole toothpaste thing had thrown me off. I had intended to tease her and see how much I could disgust her and see how vehemently I could make her refuse to do it, even getting in a fun dick flash, perhaps. But now, jeez, it seemed too wrong.

"You know, there's no way I was going to do all the dishes for a whole year if I lost," I lied. "And I didn't think for a second you'd ever blow your own brother..." And with that, I'd let her half off the hook. But I couldn't leave it at that. I had won the damn bet, after all; I should get at least a little schadenfreude out of it. So, I smugly added, "so it looks like you wasted a fortune on toothpaste."

She kept her eyes straight ahead and absolutely nothing changed about her demeanor. Calmly, she said, "I. Never. Ever. Welsh." And then she turned to look at me, her flat expression turning to one that asked who I thought I was fooling, and added, "and neither have you, before."

My gears were spinning fast how to respond or react to that, when she grabbed my forearm and quickly changed direction, cutting in front of me and then dragging me into an alley. "This way! Quickly," she exclaimed.

"Hey! What the... Carrie! Carrie?"

We'd gotten just about a fifth of the way down the alley, to the point where the throng of people going by is still in sight and yet, in the way city people tune out their surroundings, completely invisible. Then she pushed me against the brick wall that was the outside of some store, beside a recycle bin. She reached into her purse and pulled out her cellphone, a pink brick decorated with stickers.

"Film this," she said in a short tone. And then she yanked her shirt and bra up to bare her firm, full breasts, revealing the pale skin inside her tan lines, contrasting against the golden flesh outside them, and her brown nipples, standing out more than I'd ever have suspected. And THAT flipped the switch inside my male brain, that primal instinct that made me just do as she said and not question it, because all indications were, I was about to get some action from a hot female. Which is all that the further that little peanut of a reptile brain thinks things like that through. And so quickly I swiped and tapped, until the vision of my sister, tits hanging out with the throng of people passing behind her in the background, as she dropped to her knees in front of me, came into focus, filling the screen.

With deft, nimble, feminine fingers topped with carefully shaped and painted nails, she undid my belt, button and zipper, and fished my rapidly stiffening penis out the slot in my boxers. She knee-walked a little closer to me as I watched her contemplate my growing cock before her eyes, held in her hand. She licked her lips a little to wet them, and then without hesitation or foreplay, swallowed me to my root. Immediately, she started a steady bobbing rhythm with her head in my lap, paired with a systematic sucking and licking that seemed more than a little practiced.

"Well, I'll be damned," I thought, "my sister is an expert cock sucker."

With my attention focused on the feelings rushing through me as she worked my now stiffer than ever before erection with her mouth and the screen I was watching her do it on, as I struggled to hold it steady, I too tuned out my surroundings. The throngs of humanity surging across the pavement in the bright sunlight, not so far from us in our spot in the shade, if not quite shadow, just faded away. And all the noises of the city blended into static, except the sucking and gagging noises my sister was making. Actually rather quiet, but not to my ears.

Then she pulled off my cock and took a deep breath before burying her face urgently in my ball sack, kissing and licking eagerly, seeming to savor my sweaty skin and musky male odors and flavors, leaving my spit-shined shaft standing out in plain sight just off the city street. One woman passing by, only one of many, took any notice, her head swiveling just a second to record the sight to memory, her lips barely twitching in a slight smile of thrilled recognition, before she scurried on past to whatever job a smartly dressed middle-aged woman in a power suit and tennis shoes walks to. And the men all were oblivious.

Then my cock was back in her throat, and I could feel her tongue working just past her lips to taste more of my balls for a moment. Then she resumed her rhythmic, coordinated bobbing, sucking, and licking technique.

I was lost! My head swam. My vision blurred. "How," I wondered, "how could this be happening?" For a brief moment, as I felt my knees weaken and my eruption growing nearer, I thought I had to stop this. I couldn't cum in my sister's mouth! Not my own sister!

But then, it was happening. I bit my lower lip so hard I was surprised I didn't draw blood to keep from crying out, knowing I didn't dare attract attention. And my balls drew up tight, and I began to shoot off forcefully.

Carrie made more noise than I did, slurping down every drop. She moaned; she groaned; she gagged and gurgled and gulped, mmming and hohhhing deep in her throat as I fired slimy glob after glob of guy goo down her gullet. Then she popped off me and snatched the camera from my shaking hand. Freeing me to slide to my ass and topple over to the pavement, looking up at her.

She turned the camera to face herself, being sure to pan across her bare tits. Then she framed her face in the center of the shot and winked. She opened her mouth to show the few streaks of my jism that she hadn't taken right down her throat clinging to her pink tongue, which she extended towards the camera to show it off. Then she retracted her tongue, her throat contracted as she swallowed, and she then stuck it back out again to show it cleaned off.

"I just sucked some guy off in an alley," she said, then broke into a lusty giggle. "What can I say? Just another day in the city."

Then she did some tapping and swiping and put it away in her purse, which had hung from her elbow the whole time. Then she put her tits away, adjusting the cups of her bra until they were situated right, and rose to her feet.

"For fucks sake, little brother," she said with a hint of amusement in her voice, "put that thing away. We're in public, for fuck's sake! As a matter of fact, just pretend you don't know me. I'll see you at home." She then turned and walked a few steps towards the sidewalk, before she stopped and turned back a minute. "Oh, and bro?"

"Yeah," I answered weakly.

"Three hundred and sixty-four more to go."

And with that, she was gone. In a moment, I rose to my feet, and with some embarrassment, zipped myself up and brushed the dirt off my clothes. I was about to head on my way home, a journey I had no doubt would be filled with swirling inner conflict, when I saw the plastic bag from the drug store at my feet, realizing she forgot it. Numbly, I bent, snatched it up from the ground, and trudged out of the shade into the brightly lit stream of people.

Riding up to our apartment in the elevator, I had a few minutes of boredom to fill in. It's amazing how fast we can go from life-changing moments of excitement to soul-crushing boredom in our modern lives. But if anything will do it, it's those moments spent dangling over a void in a box, trying not to think about the peril we were in. This is easy because it seems so innocuous, this wood-paneled box with the short, industrial carpet, where the soothing yet annoying muzak plays. Which always begs for a distraction.

So I looked in the bag. Yes, there was toothpaste. One box. There were four different boxes of sex lube and lotions. And a pregnancy test.

"What the fuck," I exclaimed. Then I apologized to the nice old lady headed a few floors above me, who still shook her head at me as I exited the dangling box on my floor.

Never had I been so confused. But when I got home, I found I was alone. So my questions would have to go unanswered for a while.

To be continued...