ENTER: Short stories of unexpected encounters

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The Tree House

The ride to the coast took forever.

I sat in the back seat of my parents’ BMW, as they spoke about their latest high stakes buy-out. Both were investment capitalists and they got a rise out of talking money.
We were off to a weekend company retreat where they would lock themselves in the board room to dive into how to gobble up their next vulnerable company. Their genius boss thought bringing their children along would be a winning act of multi-tasking. Idiots.
“... There’s a pool. There’s the lake. They have a hiking trail. And there will be other kids.” My mother was pitching. Sigh.
I looked out to the endless green and began playing with my hair. Had they left me back in the city, I was planning on throwing a party and fucking a couple of boys I had my eye on.
I learned early on that men found me sexually desirable. I inherited my mother’s classically beautiful features — jet black hair, blue eyes, plump lips. The year I turned eighteen, my breasts and hips blossomed. With my tiny waist and long legs, I was man-bait.
I discovered a voracious appetite for sex at sixteen, and I reveled in being desired.
“We’re here!” my father announced, breaking my reverie.
The massive property of the billionaire my parents worked for sat amid acres of lush flora. We parked the luxury sedan beside countless others that arrived ahead of us.
I was relieved to get out of my dad’s car and stretch my legs. While my folks scrambled to get our bags, still deep in talks about their hostile acquisition, I raised my arms and stretched, arching my back. My cropped sweater rose up my torso revealing the lower part of my breasts. I felt a little chill and my nipples hardened, as they peeked from under the heavy knitted fabric.
Mid-stretch, I saw two figures pressed against the window watching me, longing in their eyes. They were my age, maybe a little older. I pulled my shirt down and stared back. I licked my lips seductively and began walking behind my parents.
Maybe this weekend won’t be a total bore.
Everyone gathered for brunch at the mansion’s greenhouse. It was a cavernous glass structure around a heated pool, a jacuzzi, landscaped tropical plants, and enough space for a party of 500.
We were the last to arrive; and when we got to the long table, the hungry group cheered.
I had changed into a cardigan, plaid mini-skirt, a white button-down shirt, knee socks, and mary janes. My mom said I looked “cute”; but men at the table gawked ever so slightly at their schoolgirl fantasies in the flesh.
My parents’ boss stood for introductions and blah-blah-ed about the weekend game plan. I shut his voice out and scanned the table, through the protracted monologue.
Everyone else’s kids were under 11. The exception was the billionaire’s only son and his best friend — both home from college.
The meal was uneventful. The parents tried to engage us kids, but their conversations would go back to their pursuit of money. They eventually retreated to the house to talk business.
The children took off their clothes and jumped into the heated pool — a treat considering winter was creeping in.
“Wanna join the kiddie table?” The billionaire’s son asked and cocked his head towards the bar where his friend was waiting with a couple of beers.
I took his hand and slithered over. My desire to be laid flared with his touch.
“Jake.” “Rob.” “Vivian.” Introductions made.
I let Jake help me up the bar stool. They both stared at the hint of ass under my skirt when I crossed my legs.
They chatted about their major (business — big shocker) and their passion for social entrepreneurship. This was laughable to me, as our parents were about to aggressively take over a company that started as a small-town mom-and-pop.
“So, Jake, any good places to hang around here?” I glanced at the children splashing. “This Disney atmosphere isn’t doing it for me.”
“I have just the place.” He signaled a muscled man standing in the wings, his bodyguard. “Marco, we’re going to hang in the tree house, okay?”
I followed them out of the greenhouse and up a path to the “tree house” behind a patch of trees. Their bodies looked like A&F models’ from the back. The shape of their thighs under their jeans hinted to sculpted muscle. I resisted the urge to bite Rob’s Levi’s.
The path narrowed. I stretched out my arms and I could touch manicured shrubs on the tips of my fingers.
I was thankful to find a cabin at the end of the path, not some planks nailed together. The cabin was built around a tree — a rich boy’s tree house.
It was a one-room affair but was well appointed. A tree grew out of the floor and up through the skylights over the bed at the far end. A pool table was in the middle of the room. A 60-inch flatscreen TV and latest game consoles hung in front of lounge chairs in one corner. I headed for the wet bar and found it fully stocked with beer, soda, frozen meals, munchies, and candy.
Rob swiped on the console on the wall and club music began to blare. I watched them rack up the pool table, sharing a playful jest. “Care for a game?”
I squeezed my thighs together to relieve the pressure building up in my core. I wanted them both.
“I’m not good at this, but let’s give it a go.” I walked to the pool table and Rob handed me a cue stick.
Jake broke the rack, hitting the apex violently. The balls ricocheted all over the table. Rob went next and more balls fell into the pockets.
I positioned myself to play, bending over the table. Silence fell. I was showing Rob my unbridled breasts peeking out of my shirt and my ass beneath my mini-skirt to Jake who was behind me. The cue stick missed the white ball by a mile and it rolled slowly to a pocket.
My laugh broke the silence. “Teach me?” I pleaded playfully.
Jake and Rob took turns showing me how to hold the cue stick and guided my hand through each stroke. They would stand behind me and I could feel their erections bulging against my ass. I arched my back and pressed on them harder as the game progressed.
The room was quiet. I saw them low-five when they passed each other, as we circled the table for the last time.
It was my turn and I bent to take a shot at the corner of the table. I felt Jake throbbing behind me. I let him force his bulge between my ass cheeks.
“You’re getting the hang of it.” he praised softly, as he guided my shot — the last of the game.
I turned around to face Jake and pulled him to me. “Can we play something else now?” I kissed him roughly and his body responded excitedly.
I guided Jake’s hand to the spot between my legs which has been wet with desire since we walked up the path. My arms were around his neck, my hands playing with his hair. I was pushing my breasts toward him.
I moaned in satisfaction, giving the billionaire’s heir the confidence to probe deeper. He snapped my lace thong in half to give him better access to my wetness.
I could feel Rob watching us intently as he quietly lined up the balls in the triangle rack. I threw my hair over my shoulder and smiled at him, while Jake was busy undoing by buttons. I signaled Rob to come closer.
Jake began to feverishly suck my breast, biting, pinching, mumbling “Fuck. Fuck. Fuck.” between breaths. His fingers were still in me.
Rob tossed a strip of condoms on the billiard table. I smiled at the thought that this clubhouse wasn’t as wholesome as it appeared to be.
Rob kissed me deeply as Jake worked on my breasts and pussy. He was a good kisser, this one. His kiss was moist, not wet. His tongue was deliberate. I moaned as Jake gave me a mini-orgasm. I bit Rob’s lip playfully.
I pushed them both away dramatically as I let my shirt fall off my shoulders. “I want to fuck you and you. I want you to make me cum more than once.” I let my skirt fall, as I mimicked Jake’s dad, “Are we clear on the game plan?”
The two sounded off a high-five, smiling. While they may have bedded many virgins in college, they never met a high school senior with my sexual confidence.
Jake wasted little time. His shirt was off and his buckled undone by the time he slammed my bare ass on the pool table. I waited with my legs open, my fingers pinching my nipples and flicking my clit, as Jake slipped a condom on his girth.
Rob spun a lounge chair in our direction. His shirt was open revealing a six-pack, and his erection burst out from his open jeans. He sat on the chair and stroked himself, his eyes on Jake getting ready to pound me.
The first penetration was glorious! I slid down the edge of the table, so my core could connect better with his. I laid back on my elbows, closed my eyes, and moaned his name, “Jake, faster, harder.”
He obliged with the gusto of a sex-crazed frat boy that he is. He vibrated like a jackhammer for several minutes. The long, fast pumps of his ample shaft, lubricated by my wet, were bringing me to the brink. Without missing a beat, he scooped me by my back and devoured my breast, biting and sucking my flesh. I was screaming deliriously now, “Faster! Harder! More! More!”
“Fuck! I’m cumming!” Jake sounded off, as we climaxed together.
Rob was ready, as soon as Jake took his dick out of me. He took my hand and guided it up to his manhood.
Still breathless, I impatiently wanted to orgasm again!
I jumped off and pushed Rob over the green table. I sucked him eagerly. He was long. With the right breathing, I was able to suck him deep into my throat.
After minutes, the ridges around his cylinder made my lips sore. I can only imagine what those would feel like inside me.
“Damn, Viv.” I heard Rob say. He was almost there.
I took another condom and slipped it on his member. I climbed on the table and mounted him. Yes, his dick did feel good.
I felt Jake’s body behind me, his hand cupping my behind. “I am gonna fuck you in the ass.” I moaned a “Yes” wondering if I had enough room in me for Rob’s length and Jake’s girth.
Rob was sucking my breasts as Jake lubricated his dick. I was breathing deeply in anticipation.
Anal was not new to me, but this was the first time I was getting fucked at the same time. ‘Gotta love men who learn from porn.
Jake quarterbacked our rhythm — my ride on Rob and his thrusts into me. Our pace was slow at first but built up to something furious and deliciously painful. My frat boys were focused on pleasing me, and I let ecstasy flow. Minutes into the frenzied pumping, we all started to moan.
I tightened my pelvic floor muscles as my own climax neared. Rob and Jake felt it and we had a monster three-way orgasm.
We smelled like cum and lube. My ass and pussy were banged up. But I had no regrets.
I kissed Rob as I dismounted. Jake lifted me to him and kissed me, my perky breasts against his bare chest.
We were all far from being exhausted.
I smiled.
“Do you guys want to play another game?”











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