I'm Back! Let me Regale You with the Tale of Spying on (M)y Best Friend's (S)ister. (20/18) | 2016

I think, in transit, there are a lot of moments in my life where one might observe the current circumstances in their life, and wonder if they’re an asshole. Shit, if art truly affects reality, this is definitely true; everyone loves a good redemption arc. Everyone pops for a face turn. And sometimes when we separate ourselves from the story, we can get some better perspective. So I think in hindsight, things are probably kosher with what went down a few summers ago. I’m still not going back.

The summer before my Junior year of college my best friend and I coordinated some much needed hangout time at home. We were separated pretty healthily distance wise at our respective colleges, but like all the best friendships in the world, we were back to making in jokes and almost finishing each other’s sentences in no time. I think this connection was one of the prime reasons I have such a conflict boner thinking about how things went down.

Anyway my friend, Jay, hosted most of our high school and break-from-school get-togethers at his parents’ place. They were both dentists, which in sleepy Midwestern towns meant some kinda royalty. An expansive driveway, three car garage, two story house, and a personal pool was our fucking playground.

Jay wasn’t the party type, and after a particularly toxic breakup bender at the end of my Sophomore year I wasn’t too interested in drinking, but we did have a few nights of pop, pizza, and video games, with our other high school friends. Boisterous laughter, the occasional vile turn of phrase, and back-pats and hand-slaps punctuated one of our first nights together…almost as much as Anna.

I know how certain fantasies are fantasies because of the implicit risk and taboo of the ideas in question, but I swear I didn’t see Anna coming (ha). Anna was Jay’s high school senior sister, and genuinely was always a fun person to be around. She carried the nerdiness of her brother, some latent girl next door sensibilities. But shit until that one summer night she was nothing more than a platonic connection.

A freshman when we were on our way out, Anna was lithe, nervous, and just starting to come into her own. The girl I saw that night was so much more. Heading into her senior year, she was filled out a bit more, keeping her thin form with muscle tightly packed on. She smirked from the stairwell, catching my eye for the briefest of moments, before tossing her light brown hair out of her eyes, and heading back up to her room. And fuck, I was smitten.

A few days later Jay and I were lackadaisically lounging in the pool, when Anna graced us with her presence again. Her bikini was a great combination of modesty and sexiness, blue and white stripes streaking across her small, pert tits, as well as her crotch and ass. Her hair was neatly pulled back into a ponytail, which she fiddled with every so slyly as I did my best to not stare too much. Especially with Jay paddling behind me. Thankfully, he was pretty dense.

But I was getting pretty hard as we made small talk and she splayed out on a pool chair. In a perfect…or should I say, classy porno…world we would have been alone, and she would have just let me put her sunscreen on for her, my hands would have roamed, and we would have had semi-public sex for some of the world to see. But hey, this was real life, and people just didn’t fuck their brains out all the time.

I needed a cold shower though. For suuure. I steeled my resolve, did a couple of more laps, and muttered some apology for leaving them alone. When I reached the second floor shower, I noticed something I hadn’t particularly taken account of in the past. There was enough of a thin window view from that particularly shower that stared down at the pool area. I guess there was this comfy idyllic atmosphere that Jay’s home provided me. There were never anyway coming of age boyhood frustrations let out on the wall underneath the window (I guess I can’t speak for Jay to that end), but as I felt the water warm my skin, all of that was starting to change.

Anna laid on her stomach, letting the sun kiss her light skin. The curves of her ass were simple, yet elegant, and I quickly let my mind run through images of me pressing against her from behind. I slid my hand gingerly down my stomach, wrapping a hand around my thickening cock, letting out the slightest of groans as I started to stroke. It had definitely been a while.

I felt my teeth absentmindedly carve into my lower lip as my hand methodically slid up and down my thick shaft, my palm skating over my sensitive cockhead every few strokes. I let my other hand fall to grab my heavy balls, groaning out as I narrowed my focus on Anna, who had turned over and focused her gaze on the sun above us through tinted sunglasses. Her breasts rose and fell in the heat, as she ran a finger over what I assumed were crawling lines of sweat, accentuating the exposed skin of her breasts. I wanted so badly to trace those lines with my tongue, and feel the softness of her sides as I slid her panties off of her.

Picking up speed, I pressed my forehead hard against the window, my eyes greedily travelling down her stomach, relishing the sight of the space between her legs. I wanted to trace those lines too. With my tongues and fingers…and everything else. I began bucking my hips with the rhythm of my strokes, pulling tightly on my balls as I increased my speed all around. With one last glance at the material covering her teenage pussy, I shut my eyes, biting my lip one last time and imaging pressing myself in between her legs, exploring her depths with my cock.

“MhmmAnna FUCK,” I groaned maybe to loud, spraying cum against the wall and slowing everything down. I breathed a sigh of exasperation, letting my eyes fall open before I aimed to slide back under the deluge of water.

Something was different. And to be honest, I should have expected screeching music and Norman Bates stabbing me, because there were two worlds in those moments. The world where my tunnel vision targeted Anna, and the world after I came, where she was fucking gone. My heart throbbed in my chest for a different reason as my cock wilted.

Y’know, maybe she was hot like I was. Maybe she had come in to cool off. I shampooed my hair, about to wash it out, when the bathroom curtain was yanked open. I guess I was right. She did have to cool off.

She steadied her gaze on me, smiling with spirit as I completely failed at covering up. Sweat shined so lightly on her skin, and her lips fell open as she breathed in front of me. Raising an eyebrow, she motioned to my crotch.

“Were you watching me out there?”

I bit my lip and shook my head, as she stepped closer. In a flash, she reached back and undid her bikini top, letting it fall to the floor. Her breasts were everything I ever dreamed of. Chestnut colored nipples capped off her white skin, hard in the tension filled air between us. My cock twitched…but only for a second. Anna reached out a small hand, her nails curling around my wrist, moving it out from in front of my soft cock.

Smirking, she focused her eyes on mine again, pulling my hand up towards her chest. Entranced, I let her press her chest into my grip. She moaned so slightly under my squeeze, giggling adorably as my cock only twitched for another brief moment.

“I fucking knew it!” she said louder than she had to, her hand covering mine and forcing me to squeeze her tit harder.

“Anna look-” I began.

“Shut up,” she said matter-of-factly, dropping my hand and dancing out of her bottoms. Her pussy was neatly trimmed as she stepped into the shower with me. I guess there was still a bit of a cognitive dissonance. She was still very much my best friend’s sister. As such, I bit my lip and just went with her flow. Anna smiled, curling a hand around my cheek before drifting the back of her fingers down my chin, neck, and chest. She flattened her palm out down my stomach, and teased the top of my happy trail before she shot both hands up into my hair, working with the dormant shampoo.

“Hold onto me?” she asked sweetly, stepping up on her tip toes, kissing the side of my head as she washed my hair. I felt her lips settle on my ear as I pulled her closer, my hands almost shaking on her hips.

“I used to watch you all the time from up here,” she licked her lips and smiled, digging nails into my scalp, “you were always Jay’s hottest friend. That smile…that tan skin…fuck,” she breathed, moving her hips against mine, pressing the top of her pubic bone against my cock. I gripped her hips tighter, holding her there as I felt my loins come to life again.

“I’d be up here, pressing my little forehead against the window, working these little tits…fucking my little cunt with my fingers as you shined in the pool. I’d try to time myself going deeper with times where you adjusted yourself,” she smiled as my cock breathed again, “did you think people would notice…that cock pressing against your board shorts?”

She pulled my hair a bit, tipping my head back and kissing my neck. There it was. My dick painfully swelled between us.

“Mhmm. Yes. That cock,” she giggled as she kissed down my neck and chest, dragging her nails down my sides as she knelt in front of me. My reviving cock leaked precum, growing just a bit more when Anna attacked it with her lips. She was eager as hell, and I loved that. Her soft lips pursed around my head, blazing a trail back and forth on my shaft. The girl’s hands traveled around to my ass, pulling my tightly into her wet mouth. She hummed as she bobbed up and down, and I groaned out as I shot a hand down to curl in her hair. All she did was nod before I picked up the inadvertent bucking of my hips.

I sank my throbbing member into her eager mouth, my balls softly working against her chin. She smiled as she slid a hand around to caress them, popping my cock out so she could jack me off with her other hand.

“Are you gonna cum for me?” she put an almost diabolical emphasis on that phrase, “are you gonna cum for me a second time?” I groaned out, my breath increasing as I steadied my eyes on her and nodded.

“Cum for me baby. Like I came for you in this shower so fucking much,” she moaned out before diving back onto my spurting dick. Anna moaned around the blasts of cum, digging her nails into my hip as she swallowed everything. When she pulled away, she cutely placed one last kiss on my softening head.

Raising up on her tiptoes one more time, she placed her lips on mine, biting as we finished our kiss.

“Now get out of my shower,” she smiled against my ear.