Betting On My Family - Cover

Betting On My Family

Copyright© 2016 by Bartleby T

Chapter 20: All Bets Are Off

Coming of Age Sex Story: Chapter 20: All Bets Are Off - 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  

Greymonte was quiet. A pleasant breeze blew across the well-manicured lawns, causing a light rustling noise through the trees. Squirrels hopped merrily about, dreaming about busting a nut, while blue-birds and and robins chased each other through the branches. Aside from the small furry forest-creatures, there wasn’t a sound nor disturbance, and the complex looked as tranquil as a cemetery.

Except for those damn ninjas.

Derek regretted using them almost instantly. He’d chosen Juice and Drew because they were relatively smart and in excellent shape, but it seemed to him like they didn’t realize the spectacular danger they were in. Juice was lumbering through the woods like he was deliberately trying to step on everything loud and breakable, and Drew was worse. He was quickly darting from tree to tree, doing backflips and cartwheels because, as we all know, that’s what ninjas do.

Derek had intended to split the party to divert attention from security but his friends’ ineptitude convinced him a more stand-up approach might be necessary. They all ran across the yard, one-by-one, and stacked against the back kitchen door to the Roosevelt Building. Derek checked a window to make sure the room was empty, and then knelt and began picking the door lock. It took a little longer than he expected.

“Hurry up,” Dana said. “The guards are doing rounds. Did you not see the large angry dogs?”

“Not helping,” Derek said, trying a different pick.

“This is your plan?” Drew said, laughing. “I wasn’t expecting much, but just running up to the building and jimmying the lock? Damn, you must have been a shitty cop.” Derek glared at him.

“Managed to fool you for six months...”

“Yeah, only because the idea of a cop posing as a whore was too dumb to even consider.” Drew smiled. “Wouldn’t it have been easier to gain employment as a cameraman or something?”

“Well sure,” Juice said. “But nobody fucks the cameraman. I mean why bother infiltrating the porn network if you don’t intend to get a little nookie on the side?”

“Nookie wasn’t a factor,” Derek said. “Now please, I’m trying to concentrate.”

“You never told them how you started, did you?” Dana asked. She was bent over at a right angle staring through the window adjacent to the door. Her perfectly camouflaged ass was staring him right in the face. She turned her ninja-suited face toward them and laughed again. Lately, she’d been laughing and smiling far more than Derek would have preferred.

“I remember telling you to keep it to yourself but I never thought that you’d be able to,” she said. Derek looked at her apprehensively, but she just glanced at the other faces in attendance and shrugged. “Not much point in keeping it a secret now.”

“Secret?” At the mere mention of the word, Drew had begun to develop a curious boner. It wasn’t the kind of boner meant for women, but the kind that often spontaneously arose upon hearing truly damning shit that he wasn’t supposed to know. It was a “secret” boner. “Tell me.” No one responded. “Tell me, tell me, tell me, tell me.”

“Christ, you’re annoying.”

A shout sounded from somewhere on the other side of their building. It still sounded far off but it was accompanied by a frenzy of barking, likely the security team. Dana glanced around nervously. “Time’s not on our side, Derek.”

“Almost there,” he responded calmly, inserting another small sliver of metal into the lock. As he worked it in, the yells and barking intensified until they sounded as if they were nearly around the corner. But in the last instant, he twisted the two pieces together and was rewarded with the satisfying click of a deadbolt being slid aside.

He quickly rose and dashed through the entrance, his two ninjas and pet tiger just barely making it in before the sec team rounded the corner. They weren’t safe yet, however. No sooner had he bolted the door than the guards started banging on the opposite side, loudly ordering them to open up. “Fuck,” Derek grumbled.

He jumped to the opposite hallway thinking to escape, but when he peered through the door crack, he saw another man in a suit quickly approaching the kitchen from that direction. They had no choice and no time.

“Umm hide,” he said, looking around for any available space. There was a commercial walk-in fridge along with other industrial-sized kitchen machines. No pantries or cupboards were large enough. “Into the fridge,” he said. “Go.” They all scrambled inside as the knocking intensified.

“Hush!” a loud voice yelled. They listened with their heads pressed against the door as the well-dressed man stormed into the kitchen, followed immediately by the sound of the back door opening. “No, no, no!” The man yelled. “Mr. Georgio is NOT to be disturbed!” He had a thick underlying accent that Derek couldn’t place. He sounded like Agador Spartacus from The Birdcage. Guatemalan?

“Armand, let us in. We have reason to believe that there’s been a breach. Found some gay convertible parked near the ridge.” Barking and snarling sounds could be heard not far from the fridge door.

“Gay?” Drew whispered. “If those motherfuckers touch my car...”

“NO!” The man repeated. “Mr. Georgio told the boss himself. No disturbances! He demands absolute privacy.”

“Armand! There are infiltrators on the property!”

“Then go find them,” he replied succinctly. “No infiltrators here.” Then they heard the door slam.

Once more, the barking sounded, but they breathed a collective sigh of relief that hear that it was outside the building, the heavy steps of Armand being the only sound nearby. They all listened to those heavy steps as the man retreated back in the direction from which he’d come, and they all heard those heavy footsteps pause when they reached the fridge. Then they heard what sounded like a butler noticing something slightly amiss. “Hmm.”

Then, they all cursed as they heard him lock the fridge.

In the blackness, Drew turned toward Dana. “Tell me,” he said.


“How are your nuts not the size of beach balls by now?” Riley asked. “Did you forget to take those supplements I gave you? You should be so full of cum that it’d be spilling out your ears.”

“My balls were nice and full before Babs decided to empty them ten times,” I said to her. “You know, like you told her to? Had to drink both bags just to keep pace.” I didn’t know why I was feeling so salty. I was just sick of sex after getting out-fucked by a middle-aged woman who happened to be my own step-mother. Awesome, yes, but it was also kind of humiliating. Having Riley sitting astride me fondling my junk should have helped, but her dexterous fingers jerked me to no avail. I was still about as hard as a soggy noodle.

“What I told YOU to do was drink one bag last night and the other this morning,” she said. “If you’d followed directions, fatigue wouldn’t have set in until you finished the job.” She alternated between tugging on my flaccid shaft and rolling the meat between her fingers. Neither worked but neither felt too terrible either. She adjusted her seating. Her creamy thighs rested outside of mine on the armchair and I could see her small little slit peeking at me through her micro-skirt. It was enough to give a dead man an erection.

Riley looked like a million bucks. Even before the makeup girls had their say, she’d been​ tastefully appointed, darkish eyeliner making her appear mysterious and alluring, and just a hint of lip gloss to make me think about blowjobs. Yes, women. That’s what we’re thinking about when we see your shiny lips. After the makeup though, Riley turned into my porno dream girl.

Tania and Brie simply highlighted her already gorgeous features, underlining everything that was subtle, and then they made her striking eyes appear aggressive, hyper-alert, and dominant. Her hair had been pinned up artfully, after being volumized and conditioned, and her cheeks and eyes had a girlish dash of glitter to make them sparkle and pop. She was one third girl-next-door and two thirds fantasy stripper ballerina goddess ... thing. I’d never seen her look so good, and the same could be said about my sisters, the two that were there at least.

“I don’t get it,” Katie said. “After our night together, you woke up vertical, and you’ve never been able to even look at Lexi without getting hard. What’s happened?” Babs smiled softly across the room, but said nothing. Cockswallow happened...

The sisters had also been jazzed up in glorious fashion, but Victor was still perusing the scripts so they donned big fluffy robes until their outfits were decided. Babs was also wearing one, and was currently sitting in a parlor chair, letting Tania turn her into a pornstar. The whole situation had a “getting pretty real” feel to it and I was becoming nervy about being able to do my job.

“It’s because I’m not related to you, isn’t it?” Riley asked, smiling. “I’m sorry that we don’t share a chromosome,” she joked. “I can change.”

“Don’t be mean,” I told her. “I’m impartial when it comes to sexy.”

I was wearing a robe as well. A manservant had brought out four for all the ladies but I stole Riley’s before she could stop me. Dudes appreciate soft shit too, damnit, and I needed a garment that could be opened easily at the front. Riley just wore the little skirt she’d arrived in, the skirt and nothing else. Thus far her attempts to revitalize my penis had failed.

“I’d suck on it but it would smear my lipstick,” she said.

“Wouldn’t change anything.” I rested my hands on her thighs. “If this hasn’t, nothing will.”

There was a lithe young teenage vixen sitting on my lap pouting at me with dick-sucking lips and a smile so breathtaking it hurt. Didn’t matter. Two tits were inches from my face, two 100% natural boobs that were likely rated in the 99th percentile in terms of softness, visible appeal, and squeezability. Didn’t matter. If that wasn’t enough to get me hard, the volcanic kiss she planted on my lips should’ve sufficed, or the tongue wrestling that we engaged in afterwards, or the lewd moans she’d made into my mouth, or her hands around...

“How in God’s name are you still soft?” It wasn’t Riley who said it, but Lexi. “I mean good God, I’m just watching you two and getting horny.” Riley released my lips for a moment and gazed dreamily into my eyes. I felt her fingers squeeze my still flappy dong.

“I don’t get it either,” she said. “I enjoy a challenge as much as anyone, but this is really really hard ... err, tough ... difficult. This is difficult.” Riley was the only one allowed to assist me. Both my sisters and Babs had had been willing to make an attempt as well, but the booming voice had put a stop to that.

NO CONTACT TILL THE FILMING had been his capitalized imperative to my family, but because he already had Riley and I banging on film, he was fine with us messing around. It didn’t make too much sense to me but hey, perverts are fucking weird. I wasn’t about to argue with him or his hundred thousand dollars.

Riley’s cell phone started to buzz in her purse, and she acrobatically dismounted by leaning back into a handstand before letting her legs follow. It was incredibly hot, but all I could think was “neat.” She giggled and jumped over to her purse, fishing her phone out. Lexi and Katie, sitting across from me, giggled to see my tiny little friend dangling between my legs. The flaccid penis is the funniest joke God ever told.

“Your mom is a psycho,” I said. Lexi laughed.

Syl arrived shortly after, wearing shorts and a T-shirt championing the Stanford Tree. Like every college girl, she arrived sporting dark sunglasses and a clear cup of something Starbucks. Introductions were made, hugs were exchanged, and within a few moments she was seated next to Babs, getting her own rockstar treatment. She was so casual about everything that you’d never have guessed she was there to bang her little brother, but I was long past being surprised by the Franklin women. They were a sexy, curious, and unpredictable breed, but damned if they weren’t really cute. One was still yet to arrive.

“Where’d you say Bridget was again?” I remembered someone saying something about it earlier.

“I WOULD ALSO LIKE TO KNOW THIS,” the voice said. Everyone flinched. “THE SCRIPT IS FINALIZED. WE ARE READY TO PROCEED.” The cameraman entered the room carrying a stack of blue folders and began handing them out to everyone. Everyone ... except me. I watched him hand the last two to Katie and Riley and held up my hands in annoyance. Sid just shrugged at me. “YOUR LINES MUST BE IMPROVISED, BENJAMIN.”

“Improvised? So I guess they’re not really lines, are they?”

“JUST DO YOU.”

“Whatever,” I said. The way my dick was behaving, I wouldn’t have to improvise for very long. I sighed and rubbed my temples, praying for an erection.

“Oh Christ,” Riley said. She was staring down at her phone and shaking her head. “Of all the...” She looked up at me, and then to my sisters, growling with irritation. “Seriously...” She started stomping toward the door. “I’ll be right back.” She flung open the front door and slammed it behind her, leaving us all staring after her.

I turned to Lexi. “She must be having trouble getting a boner, too.” I offered.

Lexi just blinked a few times. “She realizes that she’s wearing nothing but a six inch skirt, right?”


“Do you remember the first time we met, Derek,” Dana asked. “I still do. Quite vividly, in fact.” Dana, Derek, Drew, and Juice all sat on boxes in the walk-in fridge while the single light above them flickered ominously. Because they’d all been foolish enough to wear spandex ninja-suits, they were simultaneously freezing their asses off. Only Dana seemed unaffected, but then unflappability had always been a trait of hers. Sociability was not. Derek hadn’t seen her so animated in years.

“How d-d-did you guys m-meet?” Drew asked. He was unashamedly snuggling against Juice for warmth and the Mexican didn’t mind. He was snuggling back. “Wasn’t it at an expo or something?”

“That was the cover story,” Dana said. “That I saw him at an expo and pulled him aside.” She turned to Derek and smiled again. “The truth, as always, is far more interesting.” Derek sat against the wall, his head between his knees. He looked up from his phone.

“She’s on her way,” he announced. “I told her to get Ben, but I think she’s coming herself.”

“Ssh-s-s-ssshhh.” Drew shushed as best he could through the shivers. “S-sorry Dana. Please continue.”

“We go back a ways,” she continued. “Back before Bump and Grind even took off. Seems so long ago...” She leaned back against the wall and turned to Derek. “Had to be about a decade now, huh? I can barely believe it’s been that long. How old were you? Sixteen, seventeen?

“Fifteen,” Derek said. “I was fifteen.” He glanced over at Drew and nodded. “Yes, Drew. That means I’m actually twenty-six.”

“Aww, f-f-fuck you, dude,” he replied. “Honestly. Have you ever told the truth?”

“I was also in the army. Fought in Iraq.”

“Oh go to hell!”

“I had just moved here from Florida,” Dana continued. “Things with Harry, or ... whatever he’s calling himself these days, had gone badly. He had custody of Riley because of some bad choices, and I knew the only way to get her back was to establish myself. I needed money, but I had other problems too.” She chuckled and Derek nearly gasped to see it. Seeing her this way brought him back. “As I recall, my pool was very very dirty.”

Derek smiled. “Absolutely filthy.”

“Coming from Florida, you’d think I’d know how to clean a pool but I had just moved into the place, was incredibly busy working for my colleague’s company, and had no idea where to start. I just kept putting it off until it got bad.”

“There was shit living in that thing,” Derek said. “You didn’t let it get bad. You let it get so bad that it supported life.”

“Regardless, it got bad. So one day, I just knocked on the neighbor’s door. They had a pool, like everyone else, and I’d figure they’d know what to do. Their son offered to help.” She looked at Derek. “Fifteen or twenty-six, you look exactly the same.” She brushed her red hair behind her ear. “Some people have all the luck.”

“Interesting,” Juice said, engaged as well. “Was this before or after you started Bump & Grind?”

“Before,” Dana said. “I was working for a mid-level producer whom I later bought out. Helped me get my start.”

“Anyone we’d know?”

“We’re sitting in his fridge,” she said. “Victor used to make legitimate porn. But he got bored with it, like he does with all his hobbies and friends. When he moved onto something else, I was in the right place to take the helm. Bump & Grind started in the mansion across the street.”

“THAT,” Derek said, “I didn’t know.” He creased his brow. “You two still close?”

“It’s always been strictly professional. He kinda weirds me out. Still calls me from time to time for special requests and odd favors, but I don’t have to tell you. I saw your latest picture.” She laughed again. “Come to think of it, his non-taboo films weren’t much better, but digital media was new at the time. People weren’t so spoiled about their porn.”

Derek was staring at her, wondering what had come over her. Dana hadn’t been this candid or talkative SINCE the time she was speaking about, and he wasn’t sure what had sparked the transformation. Surely not the husband being here...

“But what about the pool?” Drew asked. “So young strapping D-Derek came over to fix your pool and... ?”

“Well, what do you think happened?” she said. “I seduced him and made him my bitch, of course.” Drew and Juice both lit up like Christmas trees.

“The fuck you did,” Derek said. He turned to Drew. “It was a few days worth of work and my parents were away for the weekend. Dana kept wearing these little two-pieces and doing all her business work lounging in the sun. We had some drinks...”

“And then I seduced you and made you my bitch.” She scratched at her mask. “No reason to lie about it.”

“ ... and then Dana convinced me to take off my shirt, and then she started asking me if I had a little girlfriend, and ... asked me if I could oil her back...”

“And then what?” Dana asked. Derek sighed ... loudly ... The older woman exhaled. “For what it’s worth, you did remarkable work for a fifteen-year-old.” She shrugged. “That’s why I decided to keep you.”

“She totally seduced you and made you her bitch!” Drew started clapping before Juice reminded him to shut up. “Oh man. I have to tell someone. I have to tell everyone! I’m so excited to be a part of this.”

“That’s not even the end of the story,” Dana said. “You wouldn’t believe the things I made him do.”

“That’s enough,” Derek said. “You manipulated me and used me and you’re still doing it.”

“Please. After a hard day of high school, you got to blow your load into a sexy older woman. You should be thanking me.”

“Believe what you want,” he said, “ ... but all that time together messed me up. When you finally broke it off, I was...” He tried to find the words. “A young kid just has no chance against an older beautiful woman, especially when that woman’s a fucking predatory viper like you.” he could see her smile underneath her mask. “And just when I think it’s getting better, you suck another impressionable kid into your machine. You’re poisonous, Dana, you hear me? You’re fucking toxic.”

“All things you could have said instead of humping my leg like a puppy and telling me how much you loved me,” she replied. “You didn’t have to come back. No one forced you to come begging for pussy at my doorstep for three years.”

“THREE YEARS!” Drew started to shake. “Oh my God. Oh my God.” He held his hand out to Juice. “Dude, feel. I’ve got goosebumps.”

“Yes,” Dana said. “Ever wonder how he seems to know everything there is about pleasing a woman?” She shook her head. “He learned from the best. He was my thrall. I did everything but move to keep you away but you always came crawling back. Even after leaving for the army, you still came back. You even joined the LAPD,” she said. “And yet, here you are.”

“Here I am,” he said. “And it ends today.”

“So you say.”

“So I know, Dana. I’m through with you. I’m only here for...”

“ ... your sister that you loved so much, yes. I remember.” She turned to face him. “But we both know I built you brick-by-brick. I’m the mortar that holds you together. You could no more survive without me than a toddler without its mother.”

“Maybe not,” he said. “But Ben still can. His family still can.” He flexed his fingers and shook his head. “If you ever try to do to him what you did to me, I’ll...”

“Save it,” she said. She scratched underneath her mask before pulling it over her head, her auburn tresses spilling out about her shoulders. “As it happens, I’m done with you, too.” She shook her hair free and crossed her legs on her seat.

“All of you,” she clarified. “I’m over boys.”


Everyday, Orange County regulars are confronted by hosts of big, beautiful behinds stuffed into too-tight shorts, scores of huge, man-made jubblies bouncing braless behind low-cut tops, and more bare mid-riffs than many small nations could lay claim to. These are normal; expected. Like the sandy beaches, sparkling water, and endless sunshine, these lovely lewd sights are simply part of the scenery.

That being said, a teenager wearing nothing but a micro-skirt still draws attention.

Felipe and Hernandez glanced up from their gardening work and one even dropped his rake as the sassy young girl walked past them, her mouth a tight grim line. They’d seen some weird things while working for Victor but they usually had to spy through shuttered windows to see young naked girls. Felipe shrugged and Hernandez picked his rake back up.

As she continued her march across the property, a roving security guard stopped dead in his tracks, watching the sexy young thing walk straight up to him on the walkway, seemingly oblivious to her state of undress. Usually stoic, he became tongue-tied as the perky little minx walked directly to him, preceded by her perky pink nipples. “Roosevelt building,” she said flatly. “Where is it?” She reached out and gently lifted his lower jaw back into place.

He jerked his head, glad to have his mirror-tinted shades hiding what he was truly looking at. “That away,” he said. “Red brick building.” He usually wasn’t so candid to strangers on the property but they usually weren’t so cute and naked.

“Thank you,” Riley said, turning in that direction. The guard watched her walk away, the lower half of her award-winning buns clearly winking at him from underneath the practically non-existent hoop of cloth she called a skirt.

“No,” he said to himself. “Thank you.”

Riley stalked up to the front door of the Roosevelt building and tried the door. It was locked. She turned back to the guard on the curb. “Would you mind unlocking this for me?” The guard hesitated.

“Mr. Georgio left strict orders not to be disturbed,” he said.

“Then perhaps you’d like to explain that to my uncle Victor,” she said. “Or do you enjoy your job?”

That obstacle out of the way, Riley pushed through the front door. Derek had said they were locked in a freezer or something so she needed to find the kitchen. The first room she turned into, though, was obviously for something else.

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