Betting On My Family - Cover

Betting On My Family

Copyright© 2016 by Bartleby T

Chapter 4: Lights, Camera, Action

Coming of Age Sex Story: Chapter 4: Lights, Camera, Action - 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 scrambled to throw on something presentable, and ended up coming downstairs in a nice polo shirt that went well with my new straight-leg jeans and Doc Martens. I checked my appearance in a rush and thought I looked good, but still very fifteen.

My parents were watching TV as I made my way to the door, but I pre-empted their questions by saying I was going to Drew's house. My dad had always been lenient with my freedom as long as I didn't screw up, so he simply said "Have fun" before unpausing their show. He had been very accommodating since I got the job. It felt good to know that he trusted me.

Which is why I felt a little guilty walking to the end of the street and loitering at the local Wawa, instead of going to Drew's, wherever he happened to live. After a moment, I remembered what Katie mentioned about her new heartthrob and deigned to peek inside, but a monstrous black SUV swung to a stop near where I sat just as I was getting to my feet. The passenger-side window rolled down an inch and I heard a voice from within.

"Benjamin?" A feminine voice called.

"It's just Ben," I answered.

"Ms. Ordon sent me. Please take a seat." I opened the passenger-side door and sat down next to a slim blonde woman wearing a black business suit with a short black skirt. Her strawberry blonde hair was pinned up high and she wore horn-rimmed glasses that gave her the severe appearance of a librarian or professor. She smiled at me cutely as I pulled the door closed and fastened my seat belt. "Clients usually sit in the back," she said.

I glanced at the backseat. "Oh, I'm not a client," I said, "at least I don't think so." I didn't know what I was at the moment. "Is it OK if I sit up here with you?" She was pretty and I liked being near pretty. "Nice to meet you," I added, holding out my hand.

She shook my hand, grinning at me like I was an idiot. "Suit yourself," she said, and pulled back onto the street. She told me that her name was Riley and that she was Ms. Ordon's personal assistant. She was the one who met weekly with Drew and Derek and spoke of them in a friendly tone.

"I usually don't function as her chauffeur, either," she said, obviously thinking it beneath her, " ... except in situations like this where discretion is important." And what the hell is this situation? I felt like a dirty little secret.

I would like to say that I was filled with excitement as we drove, but the feelings in my gut were more akin to anxiety and dread. I had no idea what Dana was going to say to me. I knew what I wanted her to say, that Derek was wrong and it was totally fine to fuck my neighbors for money, but I couldn't actually see that going down. It was more likely that she wanted to scold me and swear me into secrecy about everything to cover her ass. Whatever the reason, it quickly became clear to me that we were venturing off the beaten path.

I had envisioned Dana as ruling from a giant office in a skyscraper somewhere, but instead, we drove through the woods on a dirt road heading into the hills. Despite Riley's amiable chatter, I was starting to get scared. It was a very unusual situation for me and movies had taught me that places in the woods are where people get whacked. But after another turn in the road, a clearing opened up centered on a low grey set of buildings surrounded by parking spaces and ringed by a chain-link fence topped with concertina wire. She opened a sliding gate using a keycard and drove into the complex. Closer, I could see that the buildings were actually storage containers, like garages with rolling doors all stacked next to one another.

"Where the hell are we?" I asked.

"Just a little side operation Ms. Ordon uses from time to time," she answered. "She stores a lot of props and such here, as well as sets for her films."

"Bob & Grind Films?" I asked, remembering the company Triss had mentioned to Derek.

"Well look at you," she said. "You're not as clueless as Derek made you out to be."

"What'd he say?" I asked, but Riley shook her head.

"Forget I said anything," she said. "We try not to talk about employees with other employees. It's bad business. Besides, we're here." She pressed a button on the garage opener above her head and the rolling door on the right began to open. It was dark inside and I couldn't make out any details within.

"Where is here?" I asked.

She answered with a wink. "Your interview," she said. and pulled the SUV inside, turning off the ignition. The storage container was a large one. You probably could have parked 4 SUV's in there, if one side hadn't been set up to look like an office. The side of the room where we parked was bare, but the other half had a computer desk and across from it, a white leather couch. It was carpeted and well-lit from four freestanding construction lights. I counted five different cameras, all trained on the couch from different angles. At the desk sat Dana Ordon, tapping away on a laptop.

"What the fuck is this?" I asked, shrinking in my seat. The rolling door behind us started to close, and I felt a sneaking sensation of claustrophobia creep over me.

"It's just an interview," Riley said.

"It doesn't look like just an interview," I said. "What's with all the cameras?"

"Insurance," she replied calmly, "But you really should just ask Ms. Ordon yourself." She gestured toward the couch. Dana was still seated, typing on her notebook. She hadn't even looked up yet. "Go," Riley urged, laughing. "You look terrified but it will be fine, you'll see." I stared out the window at the harsh lights and waiting cameras. I didn't want to get out.

"Aren't you coming with me?"

"In a minute. Now go." She unbuckled her seat belt and reached across my lap to pop open my door. Her suit tightened with the stretch and I could tell that she had an alluring figure underneath it. She also smelled like heaven. "Go." She gave me a playful shove and I stumbled out the door.

Dana finally looked up. "Hello Ben," she said softly. "I trust the drive was pleasant?" Her face was lean and perfect, all straight lines and sharp edges. Her eyebrows were dark and precise, her lips red and voluptuous. She wore a dark jacket over a dark blouse, every button buttoned, every stray thread long since eradicated. It must have taken her forever to get ready in the morning.

She pointed to the couch. "Please have a seat." I didn't know what to think so I found myself doing exactly what she said. I walked closer and stepped inside the circle of lights. Before, I had been concerned, but right then, I was frightened. Every muscle in my body was vibrating with fight-or-flight, and I felt an urge to bolt for the door.

However, I was also curious, and just beginning to get a glimpse inside this secret, nefarious, adult world, and neither Dana nor Riley appeared immediately threatening. I knew I was in way over my head, but there was no imminent danger, so I approached and sat down on the couch.

I could barely see Dana behind the spotlights blinding me. "I apologize for the brightness," she said. "Most people don't realize how much illumination is required to obtain a clear picture. Let's begin."

"Why are you filming me?" I asked. "What is this?"

"I'll ask the questions," she said. "For the record, what is your full name?"

"Benjamin Rutherford Fairchild."

"And your current employer?"

"Saul," I said, "err ... Sunnyside Pool Cleaning."

"Your sexual orientation?"

"I ... what?" The question caught me off-guard.

"Do you like boys or girls?"

"I'm heterosexual," I said.

"And your age?"

"Fifteen."

"Do you know what age is required in the United States to legally give consent?"

"Eighteen."

"Perfect," she said. "Moving right along." She asked me the names of my parents and then my address and then the names of my sisters before I refused.

"Why are you asking me this?"

She stared at her computer screen. "Your stepmother is Babette Franklin, and your stepsisters, from youngest to oldest, are Alexis, Bridget, and Sylvia. Your real sister is named Kaitlyn, and your mother left when you were ten." The mention of my mother stirred me up inside but I said nothing and made my face impassive like Derek's.

"I already know the answers to these questions, Ben. I'm simply recording your responses." Her eyes flashed from the computer to me. "I'm a very careful woman, Ben. I like to be sure about the people who work for me."

"But why? I clean pools."

"Wise up, Ben. Do you really think I'd be going through all this trouble if I wanted you to clean pools?"

"I ... I thought you were angry with me, or you wanted to explain about Derek or something."

"Forget about Derek," she said. "This is about you, and you alone." She turned back to her computer. "And I'm not angry with you. Not yet, anyway. Just answer the questions."

She continued drilling me for another ten minutes and I had less and less of an idea what to think. She asked me where I'd lived in the past, the names of dead pets, my favorite color and music, what qualities I admired in others, names of previous friends, teachers, and schools, information pertaining to my academics and athletics, and even whether I preferred blondes or brunettes. And then she started to question me about sex.

How old were you when you first watched porn? How old were you when you first had an erection? Does oral sex interest you? Does anal sex interest you? And, of course, are you a virgin?

The questions she asked were incredibly personal, but I inexplicably found myself answering each and every one to the best of my ability. Something about the lights and the cameras made me want to tell the truth, and I even found myself rambling a few times after starting down some tangent to her queries. Strangely, after a few minutes, I started to feel better for admitting to things for which I might otherwise be ashamed - finding my sisters attractive, for example. I almost felt like I was talking to a therapist instead of a ... whatever the fuck Dana was. When the virgin question finally came, I didn't even feel self-conscious, and answered truthfully.

"You've never had vaginal sex?"

"No."

"How about oral or otherwise?"

"No." I had liked a lot of girls from my past school but I never had the time or the guts to ask them out.

"Good," she said, and for the first time, she smiled. A radio sat on the table next to her and she raised it to her face and held the button. "Riley. You can come out now."

The car door opened, the sound surprising me. With all the questions and cameras, I'd forgotten she was still in the room, but I guessed that was the point. She strolled across the room on her stiletto heels and stopped in front of Dana's desk. She clasped her hands in front of her and looked at the ground.

"Do you find my assistant attractive, Ben?" My heart started pounding. I wasn't sure where this was going but I felt as though I'd reached a precipice of sorts, and everything was about to change. I dodged the subject.

"What does that have to do with anything?" Dana sighed and took off her glasses, placing them on the desk. In the dark, her eyes shone as brightly as the spotlights.

"Ben, listen to me. I know I'm asking a lot of personal questions, and I know being honest is often difficult. However, honestly is absolutely essential from those I hire. I'm not your enemy and I'm not your friend. What I am is a woman who is interested in perhaps making you a lucrative offer."

She glanced at Riley who still stood, hands together, eyes on the ground. "I'm offering you more money, Ben. Lots more. I'm also offering sex. There are a number of wealthy women nearby who'd put up a small fortune for an afternoon with a handsome young man like you."

"But why?"

"I don't know," she said. "People are funny. Maybe because you're so young, or maybe because it's naughty. Regardless, I don't ask. I just facilitate. If you'd like this opportunity though, I need something from you first."

"What?"

"Trust. That's all. The questions are almost over but I need to ensure that you are physically able to perform this job. So trust me, and answer the question. Do you think Riley is attractive?"

"Yes," I said quickly. I may have been confused or unsure about other questions, but of this I was certain. She still stared at the ground but a hint of an upward curl appeared at the edges of her lips. "She's beautiful," I admitted. I felt myself blushing but I couldn't help it, anymore than I could help the hardness growing in my jeans.

I didn't trust Dana. Despite her words and assurances, being around her made my fur stand on end. Something deep and instinctual warned me to be wary around her. At the same time, I was getting a very different feeling from Riley. I had found her lovely before Dana had objectified her, and as I ogled her curves, I felt more and more like my libido was usurping control over my decisions.

"Alright," Dana said. "Stand up." I did and Dana stood as well. She walked around the desk and started to examine me as if I was a prize dog. She told me to spin around and I did, feeling ridiculous.

"Take off your shirt," she said. I stammered in response and froze up.

"My shirt?"

"Ninety percent of this job is looking good, Ben. I need to make sure your body is up to par." She looked at me expectantly and I fidgeted, locked in anxiety. "For crying out loud, Ben. It's just a shirt. Tell you what I'll do. For everything you take off, I'll have Riley remove something as well. Would that speed things up?" Riley stepped forward to stand at Dana's flank and raised her eyes to me, mouthing the word "relax."

Relax, I thought. Got it. I shook my hands loose and pulled my shirt over my head before holding it out in front of me. Dana took it and tossed it onto the couch behind me.

"Good," she said, reaching out and squeezing my bicep. Her fingers gave me goosebumps. "It looks like you already work out. Keep that up." She moved me forward a few paces by prodding, and then walked around to inspect my backside. "Yes," she said. "This will do." Then, "Fair is fair, Riley. Remove your blouse."

Obediently, Riley shrugged out of her jacket and folded it before laying it across the desk. I was unbelievably nervous, but Dana's idea was effective. As Riley slowly unbuttoned her blouse and coyly smiled at me, I was entirely focused on her and not at all upon my own timidity. I felt Dana's fingers tickling my shoulder blades as Riley's chest came into view button by button.

Her breasts were larger than I had thought. They hadn't made a large swell under her jacket, but as the buttons came undone, they revealed full heavy breasts encased in a white lacy bra. I knew by then that girls had ugly bras and nice expensive bras and this was definitely the latter. Damn, she looked good.

The unbuttoning complete, she tugged the shirt tails out from her skirt and slid it off of her shoulders, laying it to rest beside her jacket. She paced back to me, purposely landing heavily on her heels to jiggle her breasts for me. I was barely conscious of the long swollen cock throbbing against my pant leg or of Dana, who stood beside me staring directly at it.

"So I know you've probably measured it," Dana said. "So. How big are you?" I could barely hear her. Faced with Riley's overpowering tits, I felt as if I was underwater. My eyes were fixed upon the lacy white contours of the bra, and at the plump soft flesh sequestered within. It wasn't that the bra was revealing - Triss's bikini actually displayed more - it was because it was a bra, a feminine mystery only glimpsed by men under certain intimate conditions, most of them sexual. It was forbidden for a boy my age to see an adult woman in this state, and that only made it hotter.

Dana snapped her fingers in my face, shattering my dreams. "Focus," she scolded. "Your cock, Ben. How big is your cock?" She was right; I had measured it. Every guy has.

"Seven and three quarters inches," I answered. Riley giggled and even Dana smiled at the response.

"Very precise," she teased. "Go ahead and take off your pants." I nodded. I knew it was coming. I reached for my belt buckle only to suddenly realize, with horror, that in my rush to get out of the house, I'd neglected to put on briefs.

"Umm, I'm not wearing any underwear," I admitted.

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