Betting On My Family
Chapter 8: A Turning of Tables

Copyright© 2016 by Bartleby T

Coming of Age Sex Story: Chapter 8: A Turning of Tables - 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  

I woke up the next morning feeling very confused. Initially, I was jubilant, hazily recollecting Katie’s handjob abilities, but when I hazarded a look in her direction, she wasn’t there. Curious. It wasn’t entirely unusual, though; Katie was an early riser.

I stretched my back and pulled away the sheet, only to realize that I was once again wearing boxers. Huh. Curious and curiouser. I hadn’t remembered putting them back on after Katie caressed me down but I supposed that people did strange things in their sleep at times.

I sat up and wiped the drowsiness from my eyes, the waste bin catching my attention. It was empty. Hadn’t Katie tossed the tissues in there after she wiped herself off last night? What the hell was going on? Mystified, I started to feel up and down my torso but found only soft smooth skin, not the sticky mess I would’ve expected after Katie’s tongue bath. Da fuck? Was it all a dream?

“No fucking way,” I said aloud, just as the door to the attic flew open. Katie scrambled up the stairs as fast as her unbroken leg could carry her, hopping step-to-step, and threw a banana at me upon reaching the top.

“You slept in,” she said. I glanced at the clock and frowned. She was right. I was supposed to be at the store ten minutes ago.

“Damn it all,” I said, stumbling to my dresser. I quickly pulled on a pair of cargo shorts while nervously looking Katie’s way. Her eyes were on her phone as she took a seat at her desk. “Why didn’t you wake me up?”

“Sorry.” She shrugged. “Other things on my mind.” I quickly pulled on a T-shirt while I wondered how to proceed. What was I supposed to say? Thanks for the handy last night, it really hit the spot?

“Hey,” I chanced. She looked up from her phone. “What happened last night?”

She blinked. “How do you mean?” You know damned well how I mean. She looked genuinely curious, however. Was she messing with me? Before I could probe further, the doorbell rang downstairs. It had to be Derek wondering where I was. I really needed to stop leaving my phone on silent.

“I mean after we went to sleep. Do you remember what happened?”

She furrowed her brow at me. “What are you talking about?”

“Last night,” I said, louder. “Seriously? You don’t recall anything strange about last night?” The doorbell rang again. Katie stared at me like I’d lost my mind.

“That’s gotta be your friends, Ben. You should probably get the door.”

“Honestly?” I half-screamed. I scooped up my phone, keys, and wallet. Katie looked worried.

“What’s your deal?” she said. “Quit being weird and get the door.” Still barely awake, I relented and ran to the stairs. What was my deal? Either I was straight-up delusional or Katie was playing games. Regardless, I was late for work.


That morning, after Derek made me shave in the rear-view mirror, I had my first real client. Dana had been shopping my photos around to interested parties and a nice, 40’ish, buxom blonde named Vickie reserved an appointment.

The prospect of a normal job oddly made me nervous. Triss and Diana, porn stars though they may be, were much closer to my age and Riley was practically a peer. Miss Vicki, on the other hand, was twice divorced with two grown children, both older than I was. I had no idea what to expect. But I put aside my anxiety, squirted some suntan lotion into my hands and went to work with my “magic fingers.” Welcome back to the beginning of the story.

So there I was, a fifteen-year-old young man in the midst of his sexual awakening, meticulously oiling down the bubbly curves of a plump sexy cougar, sporting a rock-hard dick and an intention to break her in half with it. I had conquered two pornstars. I had conquered a nubile young sex-kitten who did it for a living. I had even kinda sorta perhaps conquered my sister ... maybe. I was young and ripped and well-endowed, and I had just taken one of Dana’s pills, designed to grant me potency and stamina. I was going to destroy this woman.

Massaging her butt had me panting like a dog within seconds and once I was finished, true to her words, she flipped over. “ ... so you can oil my front,” she had said, “ ... and then we’ll see if your dick is as magic as your fingers...”

I wasn’t certain what constituted magic as far as a penises went, but I was eager to make an attempt. It might not be able to walk on water or perform card tricks (sleight of dick?), but it did grow to over twice it’s normal size when properly motivated. That had to be worth something, right?

Hooking up with such an older women was strangely enticing to me. The nude beauty lying before me wasn’t young, nor thin, nor particularly striking about the face. But I was surprised to find her age appealing, and her extra weight was in all the right places, turning any bony angles into soft pleasing curves. And her face, though plain, lit up beautifully when she smiled to reveal laugh lines - the mark of the kind-hearted - and deep adorable dimples that spoke of the cute girl she had once been.

It was odd to think of someone older than I as “cute,” but that’s exactly what she was, and she seemed a good person, which made her more attractive. She was lovely enough to make me want to take her there and then, but I felt a strange compulsion to make sure she received her money’s worth. Was this responsibility, perhaps?

“Jesus,” I said, wiping my forehead with the back of my hand. “It’s a real scorcher, ain’t it?” She smiled at me cutely as I stood up at her feet. I leaned back and reached down to pull off my shirt but only raised it to my waist before looking to her for permission. “May I remove my shirt, mistress?” She fell out laughing, her generous mounds jiggling with glee.

“Oh fun,” She giggled. “Mistress. What a riot.” Derek had told me that some women loved to be addressed as a superior, like in role-play. It was uncanny how well he knew these types of women.

“Yes, boy,” she answered. “You may remove your shirt.” I made certain to squeeze my abs and chest as I pulled my shirt over my head, and I wore my shorts low on the hip, displaying my D’Angelo V in all it’s sexy glory. I could see her eyebrows arch above the rim of her sunglasses and she licked her lips before muttering “Where were you when I was fifteen?”

“I wouldn’t have been interested in you,” I lied, narrowing my eyes. “I only like older women.” She laughed again, a bright happy sound that made me smile too. I stepped to her side, making sure to swing my bulge past her gaze, and knelt down beside her on the blanket. “Now,” I said, returning my oily fingers to her tanned smooth hips, “ ... where were we?”

The next several moments were an exercise in restraint, but I forced myself to take my time, oiling down every inch of skin except the small strip of dark fur and the cleft beneath it. I massaged her, kneading her muscles until all tension dissolved, letting my fingers dance, press, and tickle in turns. She giggled playfully as I brushed across her belly and ribs, then fell into gasps as I moved to her breasts. They were large impossibly-firm tits, but fake or not, they were lovely, and her nipples hardened appreciatively when I gave them a light pinch.

I had to lean over to work on her shoulders, and as I did I felt a small curious hand go exploring around my crotch. It didn’t take long until she found what she wanted, and as her hand wrapped around my bulge, she whispered “wow,” arching her back to push her breasts into my hands. “ ... and where were you when I was fifteen?”

Her fingers started fiddling with the catch to my zipper, so I assumed she had enough foreplay. I lifted my right knee and pivoted onto her, kneeling astride her stomach. My shorts were tented overtop her breasts. With a sigh, I took hold of the zipper.

“Please mistress,” I said. “Allow me.” I pulled down the zipper. Gravity and my cock took care of the rest.

As hard as I was, it practically leapt from my shorts, and I squeezed my pelvic muscles along with the rest of my frontside, making me appear (I hoped) like a sweaty shredded God of Fucking. She breathed in sharply at the sight of my tight exterior, abs all pumped up, cock swollen to bursting, and she reached up to touch my sides and stomach, as if to make sure I was real. I was, as was the utter devastation I was about to unleash upon her pussy. But first, there was something that I’d been dying to try.

I took my dick in hand and angled it downward while kneeling lower until the thick shaft nestled into the cleft between her breasts. Then I seized her cleavage and pressed inward from the sides, sandwiching my pole between two slabs of warm oily tit. The fit was perfect, the feeling exquisite, and my pelvis seemed to thrust forward of it’s own accord as she swooned, “Yes, oh God, yes. Fuck em. Fuck my tits, pool boy.” I vigorously complied.

I smashed them titties like they were the last pair on Earth. I wanted to take it slow, but those tits were never meant to be treated gently. I squeezed my ass and pushed, and my rigid meat slid effortlessly through that love-tunnel of boobflesh, the big head firing back spasms of pleasure so intoxicating it made my toes curl.

On the second push, lovely miss Vicky made it even worse by leaning forward and planting a long wet kiss upon the bell. By the third, I had succumbed to animal impulse, and began to hump her chest maniacally like a chihuahua to a couch cushion. My fingers kept squeezing, twisting, and pinching like Derek had taught me, and my hips turned into a sloppy wet blur, slamming through her cleavage with enough force to shake her entire body.

Five minutes prior, she’d been scolding me about being too eager, but the gleam in her stare and the way she desperately licked at me with each penetration told me that she had just needed a little warm up. She was a slave to the moment now, just as I was.

I pumped those tits for a good several minutes but the pills Dana had given me worked like a charm. I felt all the pleasure inherent in sexing huge boobies and yet the absolute desperate need to cum was absent. I just wanted to keep fucking. Knowing that I had some time left before my first pop, I reached behind my back and went searching for her slit. She was a paying customer after all.

My fingers found her landing strip first and slid down further like a jet coming in to find an absolutely drenched pussy just dying for attention. The amount of heat it radiated was impressive. Careful to keep up my hip-gyrating tempo, I buried my pointer finger into her cunt all the way to the third knuckle. It wasn’t very subtle or suave, but I felt her tighten underneath me, and it was if her whole body vibrated.

“Oh my God,” she gasped, and pushed off my other hand to begin squeezing her tits together herself. Then she moaned as I slid my middle finger into her as well, both deep to the hilt. “More,” she panted. “More!”

And then I remembered my training, and started rubbing the pad of my thumb in tiny circles against the eensy-weensy little button at the crest of lips. First, she locked up. For a beat or two, her back arched violently and her stomach tightened. Then, she went absolutely apoplectic, jerking and twitching beneath me like she was receiving shock treatment. Ahh, the female orgasm; so elegant, so graceful.

“Holy fucking shit,” she said after returning to Earth. “Where did you learn to do that?” Poor girl. She must have been hard up if she thought a simple finger diddle was impressive. I answered her with only a grin, continuing to hump her chest, but the truth was that when Derek and Drew weren’t actively fucking their clients, they were bragging to each other about how well they could fuck said clients. I just listened to their “principles,” - they took themselves very seriously - and applied what I learned.

All it boiled down to was consistent pressure applied to the right areas. You stick something between the lips, stroke the little bud on top, and always remember to mind the nipples. They are the gatekeepers to happy town. It wasn’t exactly rocket science. I didn’t understand why some guys had so much trouble getting women off.

She was still wearing her shades, but she chose that moment to remove them with a flourish, staring up at me with smoky lust-drunk eyes. “Eat me, pool boy,” she commanded.

“Gladly, mistress,” I replied, and thus did Benjamin Fairchild begin his education in the celebrated art of muff-diving. My abilities would one day become the stuff of legends but I was still young then, and inexperienced. I made up for it with enthusiasm.

I loved everything about it. I loved the velvety feel of her lady lips upon my tongue, I loved the way she squeezed and fluttered her muscles against my ministrations, and I LOVED the way her tanned smooth thighs clamped down upon my skull when she came. Eating out Diana had been interesting, but with Vicky it turned into quite an enjoyable and thrilling experience.

I have since learned that diving for clams is more fun with more mature women. A crucial difference between girls and older women is that the latter tend to know what they want. As silly as it seems, they are more in tune with their lady parts and they know what does and doesn’t work for them. And they’re vocal about it. Because of self-esteem issues, anxiety, or simply lack of experience, many younger girls are unwilling or unable to communicate what they need to cum. And because every girl is a bit different, it can be difficult to hit that sweet spot to drive her wild.

Vickie knew exactly what she wanted, and my tongue was all too willing to comply. There was a profusion of “yes”s and a handful of “no”s, but most of her exclamations were the ever helpful ones: “lower,” “harder,” “faster,” and “keep doing that.” After a few moments, her instructions turned into a slurry of garbled syllables and wanton moaning, and that’s when I knew I was hitting her spot. I kept hitting it.

After wildly thrashing and bucking her box against my face for the fourth time, I had to have her. I helped her to her feet before scooping her up and throwing her over my shoulder like a sack of potatoes. She giggled and laughed the whole time as I carried her back into the house to her waiting king-sized bed.

By that time, my balls were beginning to ache for release, so I decided to give my tongue a rest. I tossed her onto the mattress and crawled on top of her. I leaned over her on my elbows, but then lowered my body onto hers, letting her feel my weight. I kissed her lips, her cheek, her neck as she moved and panted beneath me, staring up at me adoringly. She even blushed when I smiled at her, almost as if she was fifteen herself again, and the next thing I knew, I was inside of her.

That’s about all there is to say about Miss Vicky. While I do enjoy graphically describing each and every depraved detail, the sex we had was relatively tame. I just took her, hammering her in missionary for the next ten minutes. I pounded her through two more orgasms, kissing her everywhere like a lovesick puppy, until I finally came myself, exploding what I imagine was a massive load deep into her quivering embrace. Almost immediately, I remembered with horror that I forgot to use a condom, having never needed one yet, but she caught my expression and assured me that it was alright. She’d had her tubes tied the year before.

Bolstered by her assurances, I fucked her again ... and again.


After the hour was up and my balls were sufficiently emptied, we all went to In & Out Burger to refuel. The irony was not lost on us. Derek and Drew had me relay the morning’s events to them, even though they admitted to spying on me through the bushes when they were supposed to be cleaning the pool. “Not bad today,” Derek told me. “You’re starting to act cool and collected, and don’t seem like such a fidgeting dork all the time.”

“Dork? What are you, fifty?”

They each had some pointers to give, not the least of which was to remove my shorts BEFORE straddling a woman coated in tanning oils, but my irreparably stained cargoes had already conveyed that message clearly. I needed to buy some better clothes soon, anyways. I decided that I’d try to go shopping with Katie after my shift, and hopefully ascertain whether last night actually happened or not.

However, that shopping trip was not to be, for when I returned to the house, I found it curiously empty. I knocked on everyone’s doors to no avail, and thought I was alone at last, until I chanced a look out the window.

Lexi lay in one of the chaise lounges, looking damned fine in a strappy white two-piece that contrasted pleasantly with her dark sun-kissed skin. She was on her stomach and had the back of her top untied in that enticing way that girls often do when tanning.

It certainly was an enjoyable view, but seeing her reminded me that she still held my money hostage, so I ran to her room to rummage through her shit. My father had never believed in locks on bedroom doors, much to the girls’ dismay, and so had removed the deadbolts as soon as we moved in. Still, I wouldn’t put it past her to booby trap her things. I pushed open the door cautiously.

I surveyed the room and sighed, realizing that it was going to take longer to find my cash than I had thought. Stuff was everywhere. Teenage girls might be pretty to look at but they live like animals. There were panties, and jeans shorts, and balled up socks lying in piles across the floor, and her desk space was literally covered in various knick-knacks, electronic devices, and all the other unnecessary crap considered necessary by the American teenager.

I opened a drawer at random and found it stuffed with jewelry, charging cables, and a stack of pens. There was no order or rationality to anything, and the OCD side of me started to weep tears of unfathomable sadness. How do people live like this!?

I searched the rest of her desk, finding much and more of the same. Her dresser was likewise chaotic, but no money. The other options were her closet and the footlockers therein, and upon checking, I noticed that one of them had a little padlock on it. That crafty little minx.

Assured that my money was probably locked within, I changed tactics. If I couldn’t recover my property, I could at least even the scales by unearthing my own dirt on her. I sat down at her desk and fired up her ancient desktop. It was locked but it used to be the family computer before the move and I hoped she was too lazy to change the password. She was. People should really be more careful when they have a nosy brother around. I went snooping.

I checked browser history, but there was nothing interesting, not even porn. Maybe she really was as vapid and boring as she appeared. Recently opened files? Nothing. Cookies? Nothing. Almost as an afterthought, I opened the recycling bin, thinking no one was dumb enough to leave files in there, and lo and behold, pay dirt.

There were two video files deleted in the past week and a few dozen pictures. Most of them were aborted selfies taken with the webcam and several of them were ... well, well, it appeared that Lexi had an interesting side after all. The question I’d long pondered had finally been answered, and yes, her tits really were that spectacular when laid bare. I started to get hard just scrolling through them.

Most were the standard “staring at the phone in the bathroom mirror” variety, and many were blurry or dark; worthy of deletion. Some of them were actually well-done however, and a few were fairly tasteful. There was a silhouette of Lexi from the side, back arched so much she looked like the letter ‘C.’There was a shot of her sitting on the bed, taken from above, showing one curious bright eye peeking out through her long blonde tresses. There was Lexi cupping her breasts, lips curled into a bemused knowing smile.

And then there was Lexi sitting on the bed with her legs spread, two fingers deep inside herself. The expression of desire on her face seemed genuine, as did my resultant boner. I quickly zipped the lot of them and sent them to myself via her email with the subject line “some sexy nudes just for U! LOL, xoxo luvluv.” That ought to piss her off.

Then I checked the videos. The first scene opened to Lexi lying on her bed, frigging herself. Daaamn, son. It was likely the source from which the picture of her on the bed had been pulled. Lexi’s breaths were quick and desperate and her abs undulated erotically as she humped her fingers. I was forced to admit that she had a good screen presence. She kept up constant eye-contact with the camera and before I knew it, I was fully hard. Then she did something unexpected. She spoke.

“Circle the bed,” she said. “Get me from the other side.” And then, the camera shifted. Oh my God, I thought. Who’s holding that camera? “Now toss me that,” Lexi commanded, and a giant brown rubber dick flew through the air to land, quivering, on the bed beside her. My eyes widened as she produced a bottle of lube and began to stroke the enormous floppy thing.

Then she placed it at the entrance to her waxed pussy, and began to push. “It’s so big,” she giggled at the camera. “I can’t ... uhh...” She winced and her eyes rolled back in her head as the giant head atop the dong popped into her slit, another inch of slick rubber sliding in behind it. She collapsed onto her back, flashing “fuck me” eyes at the camera as she eased in some more.

 
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