Betting On My Family - Cover

Betting On My Family

Copyright© 2016 by Bartleby T

Chapter 1: Won't You Be My Neighbor?

Coming of Age Sex Story: Chapter 1: Won't You Be My Neighbor? - Ben is out of sorts after moving to idyllic Orange County with his family and is coerced into the illegal and dangerous sex trade. As a crisis at home ensues and difficulties at work intensify, Ben’s family and a motley crew of co-workers are forced to make difficult choices before their new fairy-tale existence comes crashing down around them.

Caution: This Coming of Age Sex Story contains strong sexual content, including mt/ft   mt/Fa   ft/ft   Mult   Teenagers   Blackmail   Coercion   Drunk/Drugged   BiSexual   Heterosexual   Fiction   Humor   Incest   Group Sex   Anal Sex   Double Penetration   First   Oral Sex   Prostitution  

"Mmm, that feels so good," she said. "You've really got a knack for this. You have no idea what you're doing to me."

"Thanks," I said, for lack of a better response. To be honest, I really didn't have any idea what I was doing to her. I'd simply squirted some of the coconut-smelling cream into my palms and massaged it into the tanned flesh of her shoulders. I'd even been about to ask her if I was doing it right when her moans convinced me that I was, and I became even more sure when she murmured "That's nice, now go a little lower."

It was the summer of 2015. I was fifteen years old and hard as a rock.

I allowed my lotion-covered fingers to drift farther down her back, brushing against the spaghetti strap of her bikini top. "Derek wasn't lying," she said. "You really do have have magic fingers." Magic fingers? The lie was so ludicrous that it made me smile, but I quickly corrected myself, remembering Derek's words. "Never smile," he said, "it makes you look like a clown. A serious expression makes you seem dangerous, and women like to fuck dangerous."

But maybe my fingers were magic. Who knows? I had no other way to explain how I was doing so well. I'd never helped a woman apply suntan lotion, let alone given a massage, and Derek knew that. I moved my hands lower and started working the oil into her tanned lower back. I spread my magic fingers wide and swept upward, starting from the arch of her butt and kneading my way upwards until my fingertips again grazed the strap of her top.

"Here," she said. "Let me help you. She reached backward to grasp one of the ends and gave it a tug, the knot unspooling. The straps fell down her sides as Derek's words came to me again. "It's important not to rush things but these women know why you're here and it's not to clean their fucking pool. If she gives you a signal, seize it."

The only problem was that I was only fifteen and had no idea what constituted a signal. I was glad that she lay face down and so couldn't see the indecision cross my face. Was this a signal? Should I do something or just keep oiling her back? Derek's words: "It's 90% confidence, kid. Never hesitate." I took my chances. A woman untying her bikini sent me a pretty strong signal whether she had intended to or not. I seized the opportunity, or rather, I seized them.

I slid my hands down her sides and underneath the cups of her top. She stiffened as she felt my inexperienced hands clasp around her very lovely very fake tits and then I heard the most ego-damaging sound a young lover will ever hear - a giggle. She was laughing at me. "Slow down there, Casanova," she said. "You young men are always so eager." Her hands found mine and she gently pulled them away before coming to her elbows and looking over her shoulder to me. She smiled kindly through her sunglasses but I didn't detect any sign of the raging sexual inferno that I'd hoped to be inspiring in her.

She tilted her shades down with a finger and I saw her eyes go wide noticing how much my cargo shorts were tented out. The raging sexual inferno in me was very evident and pointed right at her. "So eager," she repeated before laying back down. She arched her back and stuck her butt up in the air.

"Take this off," she commanded, and I dutifully peeled the slim triangle of fabric over the bronzed humps of her ass and down her thighs. She lifted her knees so I could complete her undressing. "Now finish what you started." Slowly, so as not to appear too eager, I settled my hands on the back of her waist before moving lower and rounding the curves. Eager doesn't begin to describe how I felt on the inside, and my heart was beating so fast that I was becoming light-headed. I firmly gripped a handful of butt flesh, squeezing and pulling the cheeks apart so that her glistening sex peeked out at me.

I wanted to mount her right there. I wanted to straddle her waist and sink every last inch of me into that slick hotness. I wanted to push her against the towel and hold her there while I pounded her senseless. I wanted to make her body mine, and to make it ache, and then I wanted to fill her up with my cum so as to claim my property. It sounds barbaric - and it is - but if you ever see a fifteen year old boy staring at a woman and wonder what he was thinking, it is this, more or less. We're animals.

I would never act on any of these urges, of course. I was still trying to understand them. I had only ever kissed a few girls before, let alone mounted them, and while the thought of doing so filled me with desire, it also filled me with anxiety. I wasn't completely without a clue, but sex was still a big mystery to me. It was a mystery that I wanted to pursue, of course, but still a mystery.

I was trying to learn though, and so took her advice. "Not so eager." I massaged past her bottom and reoiled my palms to begin on her thighs. She moaned appreciatively. "Once you're done with my back, I'll flip over. Then you can oil my front." My heart, impossibly, started beating even faster. "And once I'm all oiled up, we'll see if your dick is as magic as your fingers." I grinned and didn't care if she noticed.

"It is," I assured her, and she laughed again, only instead of bruising my ego, this time she stoked it.

"Well then get to it, young stud. I have a lot of tension to deal with before my 3 o'clock. You've got a lot of work ahead of you."

"Yes ma'am," I replied and put my hands to purpose. This was turning out to be the best job ever.


If I was to examine all the years of my life up to now and choose the best one of all, the one in which I had experienced the most unadulterated joy, I would not choose the year I met my wife, or even the year we had our beautiful twin girls. These were pinnacles in my life, incredible moments that I cherish and will never forget, But I would still have to say that 2015 was the winner. That summer was like a perfect storm of good fortune for me.

Three big things happened that year. The first is that my father, my sister, and I moved from the suburbs around Pittsburgh to a sunny and affluent neighborhood in Orange County, California. My father, a mild-mannered IT director for our school district had started a software company with his old college buddies in the hopes of striking it rich in the apps market. Their first creation "Gadzooks!" - a relatively mundane indie space sim - ended up bombing commercially, but an astute investor noticed that the physics engine they designed for the game was incredibly robust, revolutionary even. It was the result of talented passion, focused effectively. Only a year after founding his company, he and his co-owners sold it to a larger game manufacturer for seven figures and a job. His new offices were in California, so we moved out there as soon as school was out. Naturally, as a fifteen-year-old, I was pissed. I bitched considerably:

"What's so fucking important in California? All my friends are here! They don't even have seasons in SoCal! I'm a Steelers fan, damn it!" All arguments considered, that was the gist of it. Unfortunately for me, all of my complaints were all of the juvenile high school variety, and the fact that southern California doesn't have seasons could not dissuade my father from accepting the life-changing offer of employment.

The second event of 2015 was that my family got a little bit bigger. In early May, before the move, my father Clarence Fairchild married Babette Franklin, his long-time girlfriend. They married quickly because of the sudden unexpected job offer, but both my twin sister Kaitlyn and I knew it was coming. They were adorable together, and Mr. Fairchild was simply a better man when she was around. Katie and I liked her.

Like my father, Babs was a divorcee and had three children of her own. Sylvia, her eldest, was already in her freshman year at Stanford, but the other two girls -- Lexi and Bridget -- would both be moving into our new house in California with us, which I was assured would be big enough for the entire newly-extended family.

The third major development in 2015 was that I finally got lucky, in spectacular fashion. I know that ranking the loss of my virginity on par with these life-changers may seem a little prurient, but I was fifteen and sex was and is a big deal to me.

Now, the loss of one's virginity is usually a disappointing affair. One or both participants have no idea what goes where, how to act, how to move; things of that nature. It can be awkward or even painful sometimes, and guys tend to last all of two minutes before they're finished. In comparison, my experience was fucking awesome and the long sweaty months that followed were so momentous as to inspire this account, and turn 2015 into the best year of my life.

To be fair, this story isn't all sugarplums and bubblegum. I wasn't drowning in ass right off the bat, sad to say. There were more than a few obstacles to get around and plenty of hoops to jump through like any other time in my life, but a chance encounter at a welcoming party shortly after our arrival in Cali brought into motion a chain of events that would drop into my lap all the sex that I could handle, and I was fifteen; we're talking a lot of sex, here.

It all started with a summer job.


"You know Katie, I know you don't want to hear this, but our sisters are kinda hot."

"You're right. I don't want to hear this."

"I mean, I kinda thought so before the wedding too, but tonight, they look amazing."

"You're not allowed to think they're hot anymore. It's gross. For Christ's sake Ben, they're your sisters!" My twin Katie and I stood with our backs against the wall of The Hilton's ballroom. My dad's new employers was having a celebratory meet and greet in honor of his arrival and the acquisition of his company. It was quite the swanky event and the whole family, all seven of us minus Sylvia - who was summering at school - had to unpack our best duds and get our hair did so Reckless Games could see what an upstanding WASPy family my father had. Five minutes into hors d'oeuvres saw Katie and I against the wall with little plates of nibbles doing what we liked to do best: people-watching.

"I can't stop thinking they're hot just because dad decided to put a ring on it. I mean damn, are you seeing this dress Lexi is wearing?"

"Shut up, you're disgusting." I knew talking about our new sisters irritated Katie and that's part of why I did it. The other part was that Lexie was sporting a sprayed-on backless cocktail dress that accentuated her already impressive cleavage and full creamy thighs. Lexi had lately become my greatest source of boner inspiration, and billions upon billions of little Bens were sacrificed in her honor almost every night. I couldn't stop fantasizing about her, but then again, I couldn't stop fantasizing about anyone. You would never guess by looking at her that she was only 16. Many of the suits casting her lascivious looks from across the room would check themselves if they did.

"You're just jealous," I said. Her eyes narrowed at me but her smile was amused.

"Jealous? Why should I care which skanks you find attractive?"

"It's OK, Katie." I grinned at her and sipped my punch. "I think you're pretty too."

"Oh Jesus. Just shut up, Ben. SHUT UP!" She stomped off in a huff towards the open bar and I couldn't help but stare as I watched her leave.Though she was my twin, and though I felt super creepy admitting it, Katie was turning into quite the fox herself. She didn't have the curves to match Lexi due to her athletic Tom-boy nature, but long hours on the stair-climber and three years of track had graced her with an ass that deserved to be cast into bronze. But, she's my sister, so just ... eww.

There's something nasty and morally repugnant about considering a blood relative in that way, but there was power in that ass. I had once gotten hard just watching her do lunges, and I'd wanted to throw up afterwards from the guilt. Sometimes, I wished she grow an extra head or gain a hundred pounds so I could stop feeling lustful towards her, but I knew she wouldn't. She was a natural athlete, just like dad, and just like me.

"Hey Ben! Come over here for a second. I'd like you to meet someone." My dad was gesturing to me from across the room. I walked over and stood at his side as he finished explaining his future projects. He rapped me on the shoulders as he turned the conversation to me. "Ben, I want you to meet Dana Ordon. She's an investor and was one of the deciding votes in acquiring my engine. I extended my hand and was surprised when she greeted me with a strong brisk handshake.

From her appearance, I had expected a more dainty response. She was wearing a deep scarlet dress that matched both her auburn hair and crimson lips, in addition to her spiky heels that made her appear only a few inches shorter than my 6'3". She was tall but had a thin delicate nature to her, like she could be blown away by a sharp breeze.

"Hello Ben," she said, and then "Wow. You're a lot bigger than I thought you'd be."

"I get that a lot," I said, because it was true. Puberty had struck me later than usual but with the force of a thousand suns. Over the past year and a half, I'd been growing so freakishly fast that my bones ached. My voice had lowered almost overnight into a deep uneven timbre, I started growing hair in really weird places, and I crested six feet by my fifteenth birthday. I was still growing, too.

I had been weight-training since I was twelve, and playing sports since before I can remember, and I'd ended up gaining over eighty pounds in less than two years. In baggy clothing, I could almost pass for a man grown, and only my boyish face with it's peach fuzz and high dimples betrayed my true age. She looked me up and down with a clinical eye.

"I certainly don't remember boys your size when I was fifteen," she said.

"Yeah," my dad replied, beaming with pride. "He takes after his old man." Clarence had played football for Notre Dame, is 6'5", and must be one of only a few programmers in the country that can bench-press over 450 lbs. Dude's a beast. He's not your typical code monkey, unless your typical code monkey likes to unwind from a hard coding session with a round of power cleans.

"Dana might be able to help you with a job, Ben."

"Oh..." I said, caught off guard. "That's ... that's great." Only, it wasn't. My dad had a thing about hard work, due diligence, competition, and excellence, but I didn't share his commitment wholeheartedly. My sister and I had strict rules about study time, homework time, chores time, and fitness time, and I barely had time for friends as it was, with all my extra-curriculars. My sister and I sometimes felt like we were being raised like race-horses instead of real people. But still, dad felt it was important for me to hold down a part-time job so I could learn the plight of the working man, despite the fact that I wasn't even old enough to work in most states.

"I guess I could use the money," I added. Even though dad had scored some cash from selling his company, Orange County was expensive as shit and the house he found for us cost him so much that he refused to tell us exactly how much. Besides, he was tight-fisted when it came to allowances as it was. Dana smiled at that, and then looked me up and down again. It struck me as odd that she was inspecting me like a commodity. "What's the job?"

"I own a number of commercial entities around the area," she explained, "but with the economy the way it is, there is only one position I can offer to a boy of fifteen." My father was nodding attentively, more interested than I was. " ... but I actually think you'll be perfect for it. Tell me, do you know anything about cleaning pools?" And that was how I landed the best job of my life.


It didn't strike me as all that great from the start, though. The majority of the work was outdoors and Southern California is a pretty hot place to work outdoors. It also seemed to me a form of torture to endlessly work around clean pools of cool refreshing water without ever being afforded the chance to jump in and cool off. During the interview, the manager also seemed intent on frightening me by telling me how difficult the job was. "You gotta be here by 8 o'clock sharp," he would say, "and you gotta make sure the store-front is clean and the chemicals are stocked before you head to your first house, and you have to make it there by 9!" Everything he mentioned sounded ridiculously easy, so I wondered what the difficult part was.

"This job is cake," one of the other stockboys assured me. "Plus, you'll get to roll around with Derek and Drew. They're cool peoples."

I was to report for work at 8am the following Monday and I hadn't even been in California a whole week yet. I didn't have a driver's license yet, but the place was only a few miles away so I could walk or jog there without issue. It was while I was walking home that first day, in fact, that I first met Diana, the lady from across the street.

Like most other afternoons, I had women on my mind, and walking through the suburbs of Orange County was not helping matters. People dressed differently here. I was used to a jeans and T-shirt crowd but women here wore practically nothing at all. Because it was an upscale neighborhood, there were legions of joggers, and most were clad in varying amounts of Spandex accentuated by tight sports bras.

Dudes were running around wearing nothing but shorts. Girls would be seen playing in the streets wearing tank tops and bikini bottoms and glimpses into backyards revealed pool after pool after pool, many ringed with bronzed skinned goddesses worshipping the sun in skimpy swimwear. Everywhere I looked was flesh and sex, and my already giant libido grew with each jiggling breast I saw bounce down the road.

I was just about to turn into my driveway when a shiny black Lexus swerved into the driveway opposite mine. It was moving way too fast to make the turn and the front bumper smacked off the curb as the tires squealed and it came to a stop. It wasn't a cool maneuver. It was just shitty driving. Still, it made me pause for a moment, curious.

The car door opened and two girls spilled out of the front seats, big goofy movie-star sunglasses screening their eyes. They were both wearing short black dresses and heels, and because it was Saturday morning in the suburbs and not happy hour, I figured they must have been dressed from the night before. They stumbled drunkenly toward the trunk of the car, laughing hysterically.

Watching the spectacle, I could see that they were both total hotties, and hotties of similar proportions. Long tanned legs led to tight perky butts, then to slim figures adorned with unnaturally firm-looking breasts the size and shape of grapefruits. Even their hair was similar, both having shoulder length straight locks tied back into pony tails. Their only difference lie in the color: One had hair the color of dark chocolate while the other was platinum pornstar blonde.

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