Betting Night
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Betting On My FamilyChapter 3: What Women Want free porn video
The restaurant was only minutes away so there was a minimum of awkward silence before we arrived. Derek was his usual charming self as he requested a table for two, but once the waiter left to get our drinks, he pulled a small key ring out of his pocket and tossed it onto the table. I recognized it immediately because it was mine. “Found this in the upstairs hallway,” he said. It must have slipped from my pocket while I was crawling around. “What did you see?” I tried to read his face but there was nothing there. He betrayed no emotion.
“I tried to call you,” I said. “You left your phone outside and I just...”
“What did you see?” he repeated.
“I heard a noise, and thought it was you...” I continued, struggling to find the right words that would somehow make my actions justified. “You were having sex with some woman.”
“Ms. Mathews. Go on.”
“Well, that’s pretty much it. I heard you guys talking a little. I heard you say that your uhh ... finishing costs extra.” Derek blushed ever so slightly and I shrugged. “That’s pretty much it.”
Derek nodded. “Alright,” he said. “No huge deal. Kinda always figured you’d wise up, eventually. Surprised it took two weeks, honest.” He sipped his lemon tea before looking at me intently. “You freaked out?”
“I’m cool,” I lied, not wanting to piss off one of the few friends I had. He smiled very lightly and waited for me to be honest. “Alright man, I’m a little freaked out. What was that?”
“That...” he said, tearing open an Equal packet, “ ... was sweet sweet lovin’.” He stirred the powder into his tea. “And that...” he paused, “ ... is my job.”
“Uh huh,” I said, incredulous. I guessed it was at least possible. It was another one of those situations that would never have occurred in Pennsylvania, but here, I could almost believe it. “Really?”
“It’s like this,” he began. “The three of us work for Saul, the manager of the pool company. He pays our wages and in return, we clean some pools, although not as many as other vans. But Saul has a manager too, the lady who owns his company and a bunch of others.
“Dana Ordon?” I asked. His eyes widened.
“How do you know that name?”
“She basically hired me,” I admitted. “She has something to do with my dad’s company. I met her at some party.”
“No shit? I thought Saul hired you.” I told him that I had interviewed with Saul but that my dad had gotten me the gig through Dana. “Well,” he said after I finished. “That changes things.”
“Changes what?”
“Look, Dana owns a male escort service, which is very lucrative and very off-the-books. She caters to women with particular tastes.”
“What kind of tastes?”
“Look at me,” he replied. He leaned back into his chair and opened his arms for inspection. “Can you guess what tastes I satisfy?”
I looked him up and down. “I don’t know,” I admitted. “I mean, you’re kind of good-looking I guess.”
“Fuck you,” he said, grinning. “I’m ridiculously good-looking and you know it. I’m like Derek fucking Zoolander. But this...” he leaned forward and cupped his chin with one hand, “ ... is why I have this job. Dana’s clients like to be serviced by beautiful young studs. The fact that I look like I’m your age turns these cougars on.”
“But you’re 21.”
“But I don’t look 21, and that’s what matters.” I hadn’t thought about it before but he was right. He did look my age. He dressed better, usually preferring jeans or khaki shorts over cargos and it was rare to find him in anything non-name-brand, but he still carried himself like a younger man - more care-free, I guess - and from his face alone, it was likely that he’d still get carded for R-rated movies.
“Dana’s not stupid,” he continued. “She knows that she’d face a lot of jail time if she was caught actually whoring out 15 or 16 year old boys. So she looks for men of legal age like me, who look young but actually aren’t.” He simply stared at me for a moment. “Which is why Dana hiring you is so bizarre.”
“Maybe she wants to whore me out,” I said, hoping for the opportunity. Even having never had sex, I was 100% positive that it would be much more fun than cleaning pools.
“More likely, she was just doing a favor for your dad, and figured you could help us clean pools. No offense,” he said, “but kids your age are a liability. You’re inexperienced, irresponsible, untrustworthy, and worst of all - you can’t keep your mouths shut.”
“Oh come on,” I said, getting defensive. “I might be some of those, but I know how to keep a secret. Who would I tell anyway? You and Drew are the only people I know.”
“Precisely,” he said, “Dana probably took the fact that you just moved here into consideration. But still, some of this isn’t exactly legal.” He explained that all financial transactions between clients and escorts was on a cash-only basis, and that he and Drew met up with Dana’s secretary weekly to settle. “ ... part of the reason why all this works is total anonymity. Miss Mathews isn’t Miss Mathews. Only Dana knows her real name. But if anything comes back to her or her address, or if you tell anyone anything...”
“Dude, relax,” I said. “I’m cool.”
He held up a finger. “Don’t tell me to relax, Ben. I remember being fifteen, and I was a stupid arrogant asshole. You seem OK so far, but this is a big deal. I have no idea why Dana got you involved in this.” He frowned at me. “I might have to move you to another van.”
“Aww no man, please don’t move me.” I heard the desperation in my voice and how truly young I sounded and was. “I’ll be...” I happened to glance across the room and saw three women being seated nearby. “Oh fuck me.” It was the Franklin women.
Derek followed my eyes. “What is it? You know them?”
I rested my head on my hands and deadpanned “Sure do.”
“Ben? Ben! Hi, hon!” I groaned as the ever-chipper Babette strolled to the table. She gave Derek a once over on the way before fixing me with her penetrating stare. She had large blue eyes the color of robins’ eggs and they were so light as to be almost transparent, giving her an ethereal and almost supernatural intensity. It was difficult to break eye-contact when talking to her. In my opinion, she missed her calling as a police interrogator.
“Why aren’t you at work?” she asked. “Who’s your friend?”
“Hi, Babs,” I said. “This is Derek, my team leader. Derek, this is Babs, my step-mom.” She stared back at Derek, batting her eyelashes at him as I spoke. She held out her hand palm down, fingers dangling, almost like she wanted him to kiss her royal rings. Derek was amused by it and clasped her hand in his. It’s strange to see an adult, your step-mom even, find your friend attractive. “It’s a pleasure to finally meet you,” he said. “Ben talks about you all the time.” Sure I do. Aside from telling him that I did, in fact, have a step-mom, I’d never mentioned her before.
“Really?” she said. “That’s sweet. He never tells us anything about the people he works with.”
Derek turned to me in mock alarm. “That so?” He shook his head side-to-side and feigned disappointment. “ ... and after all we’ve been through.”
“We were stopping for lunch,” I said, eager to move the conversation along. I had seen how women reacted to Derek before, and the last thing I needed was for one of my step-sisters to come over and...
“Hi Ben!” Lexi walked over to join the conversation, and placed a hand on my shoulder in a kind, caring manner very unlike her. I couldn’t remember her ever touching me before, and she was trying to play it off like we were pals. I turned to acknowledge her and found my face only inches from her 34DD’s. They were spectacular and at least appeared to be all natural. When my infatuation with Lexi began, I started snooping around her underwear, because I’m a pervert, so I knew their size, and they became my gold standard: the tits by which all further tits were judged. I managed to tear my eyes away after a split second but just being this close to them left me stunned. God, she smelled pretty.
She tapped a finger on my shoulder, waiting for an introduction. “Lexi, Derek. Derek, Lexi.” Then she was done with me, removing her hand. She only had eyes for dreamy hunky Derek.
“Hello,” she said beaming, leaning slightly forward to bring her prized assets to bear. “Are you with that pool company too?”
“I do some work for them,” he said. “But I’m an independent contractor. I provide a number of services to various local businesses.” He produced two business cards from his shirt pocket and handed one to each. I’d never seen them before and was curious what they said. Derek had never mentioned working for other businesses before.
“Maintenance and Landscaping,” Babs read from the card. “Good person to know. Maybe we’ll give you a call once we finish settling in. Yard’s a little rough.”
“Always looking for more clients,” he said. “Any friend of Ben is a friend of mine.” Babs and Lexi both fawned over him for a minute, telling us that they’d been shopping all morning. Bridget also popped over for a second before excusing herself to the lady’s room. I noted that Katie wasn’t with them and I quietly simmered.
I hated to see the Franklins exclude my sister from their little shopping excursions. I had little interest in spending time with them myself, but I’d seen Katie try to get to know them and they usually politely ignored her for the most part. Babs at least sometimes tried to bring the girls together, but Bridget was distant, and Lexi was often cold and cruel. I hated the fact that I was so attracted to someone so unkind. “Where’s Katie?” I asked pointedly.
“Said she was busy,” Lexi answered, fixing her golden eyes on me. Their color was enhanced by her contact lenses and she had a vivid mystical look about her. I knew she was lying, but I didn’t say anything. I couldn’t prove anything so what was the point?
“Well we should get going,” Babs finally admitted. “I’ll see you at home, Ben. Have fun at work! Pleasure to meet you Derek.”
“Likewise,” he nodded, and they finally left for their own table. I breathed a sigh of relief.
“Oh, I almost forgot,” Babs said, scampering quickly back to the table. “One of the neighbors stopped by, Ben. A woman named Diane or Diana?” My heart leapt like a trout. I hadn’t seen either her or Triss since that awkward first day, but they had never been far from my thoughts. I often thought about them vigorously in my bed at night to be honest. “She said you spoke to her about getting her pool cleaned? Anyway, I said that you’d stop over and talk to her after work.”
“You did what?” I said, alarmed. I hadn’t explicitly avoided running into Triss or Diana, but I feared seeing them again in a very teenage, very stupid way. What would I say? How would I act? I had a huge crush on both of them.
“Well, what a coincidence,” Derek chimed in, grinning. “We had a cancellation this afternoon. We can stop over and see what the lady requires.” Babs thanked him, gushing the whole time, and Derek chuckled as soon as she was out of earshot again. “Benjamin Fairchild,” he said. “You’ve been holding out on us.”
“What?”
“You have a beautiful family, Ben.”
“Step-family,” I corrected him. “I like my real one better.”
“Regardless,” he said. “Drew and I had no idea you had such ... smart-looking sisters.” Oh no. It was as I feared. Visions passed through my mind of Derek and Drew mercilessly taunting me and asking questions about my sisters; asking me for dates, asking me for numbers. Such is always the fate of any hot girl’s brother. And Lexi, at least to me, was really really hot.
“Don’t worry,” he said, reading my face. “I’m only playin’. Family and exes are off-limits. Too young anyway.” I was about to object, but then realized that I would rather have him thinking her off-limits. “But tell me about this neighbor,” he said smiling, “ ... and tell me why your face lit up like a Christmas tree when your mom mentioned her.” I needed to learn how to conceal my emotions like he did so well.
“Step-mom,” I corrected him again, and after further urging, he convinced me to spill the beans about Diana and Triss. I told him about running into them the other day, and about their pool. I did not tell him what their business was, or about the scandalous incident with Triss. I could barely believe that happened myself.
“So I’m going to go ahead and guess that Diana is attractive?”
“Moderately,” I lied. Derek waited. It was starting to bug me that he could tell whenever I was lying or withholding information. “She’s gorgeous,” I finally admitted.
“Fun,” Derek said. “Let’s go say ‘hello’.”
We did have some work to do beforehand. Even though Derek was obviously much more than just a pool guy, we still had appointments to keep. Derek explained that while the pool guy act was a front, it also allowed Dana to have a more-or-less legitimate reason for extra revenue. “We’re not the only van that does this,” he told me, “and pool cleaning isn’t the only business she uses, but she compartmentalizes everything for the sake of security.” I didn’t understand what he meant, but nodded along.
“What I mean is that I only know a few other guys that do this, and those I’ve met has been by chance. All of her people report only to her secretary and that is our one and only contact. That way if any legal issues do arise, nothing comes back to Dana or to any other part of her business. The less an employee knows, the less of a liability they can become.” It made sense. Afterwards, Derek disappeared into the Tomlin household, emerging 30 minutes later to help me load the car. “Jesus Christ,” he said, pretending to limp, “That woman sure got her money’s worth.” I smiled, secretly jealous that I wasn’t getting to service randy housewives. “Let’s go talk to your neighbor. I need a break.”
I told him the way to her house but afterwards fell silent, trying to process all of the new information. I was worried mostly, because Derek had threatened to move me to another van. I hoped that he could realize that I was trustworthy. I understood that he and Drew occasionally banged the clients, and though envious, I was comfortable being the guy that did most of the pool cleaning. I didn’t see any reason to change anything. Derek, with his omnipotent awareness, noticed my silence and guessed what I was thinking.
“I’m going to call Dana tonight,” he said. “I just want to make sure she knows your age. If she’s alright with you knowing what you know, then I’ll try to make sure you stay with us.” Relief washed over me. I didn’t want to start over with strangers, especially now that I knew about the sex stuff.
“Thank you,” I said sincerely.
He nodded. “No problem,” he said. “What are friends for?”
We turned onto my street and I pointed out my house before telling him to park at the one across the street. “Hope she’s home,” I said, actually wishing the opposite. I wasn’t ready to see her again, but hoped it would be easier with Derek along. We rang the doorbell and waited.
“Nice place,” he noted. “Do you know what she does for a living?”
“Actress,” I said quickly. He gave me a knowing look.
“This is Orange County,” he said. “so when you say “actress,” do you mean actress or do you mean...” The door opened, cutting him off but effectively answering his question. Triss was there, holding the door open wearing only a tiny white bikini, looking for all the world like every teenager’s sexual fantasy. Yes Derek, my neighbors are pornstars.
“Well hellooo,” she said sultrily, standing back from the door. Her hips were thrust forward while she leaned back, examining first Derek and then me. For the first time ever, I saw Derek hesitate. I, on the other hand, was struck speechless, entirely absorbed by the sight of that little triangle of white material, the only barrier that separated me from my heart’s - and penis’s - desires. To his credit, Derek recovered quickly.
“Umm, hello,” he said, stating the name of our company. “Diana, I presume?”
“Hi Ben,” she said, ignoring him. I quickly looked up from her crotch and met her eyes. As before, they were full of mischief.
“Hello,” I murmured. I was mildly paralyzed by her hotness, but could at least sputter out simple words. “Diana stopped by?”
Triss nodded. “Pool’s out back boys. Go around the side. Door’s open.”
“Actually,” Derek began, “We were hoping to first discuss...” Again, he was interrupted as Triss closed the door in his face. “ ... or we can talk details afterwards...” He turned to me. “That wasn’t Diana? Who’s Diana?”
“Her equally hot partner,” I said. “She an “actress” too.”
Derek smiled wide as we turned to head toward the side gate. “Incredible,” he said, clapping me on the shoulder. “You really have been holding out on us.”
“I told you I could keep a secret.” We both laughed.
The backyard had a wooden fence, but it was barely noticeable through all of the brush, bushes, and manicured trees liberally sprinkled around the interior. Stepping through the gate almost felt like entering some private Eden, the sounds of a bubbling rock waterfall in the pool mixing pleasantly with the warbling of songbirds. I half expected small furry woodland creatures to emerge and start eating from my hands as nightingales perched on my outstretched arms, such was the tranquility of the place.
The paths around the large in-ground pool were red and black brick instead of lifeless concrete, and multitudinous flower beds were all mulched, edged, and beautified to perfection. Whoever the latest gardener was, he certainly knew what he was doing.
“Wow,” I said. “Business must be good.”
Derek shook his head. “Pornstars can make big money, but this big?” We walked around the pool toward the patio doors. “I’ll bet somebody has a rich daddy.” The sliding doors opened and Triss appeared, the early afternoon sun shining upon her buttery skin. Behind the security of my sunglasses, I examined every inch of her, from her midnight blue toenails to her silvery belly-button clasp to her obviously-fake-but-really-fun-looking tits to her own pair of sunglasses.
Even with her eyes hidden, I could feel the weight of her gaze. I’d never been the focus of attention before around Derek and it felt almost wrong, like it was breaking some unspoken rule. She moved to sit at the nearest patio table and gestured to the other two seats. We all took refuge under the yellow deck umbrella and removed our shades. “As I was saying...” Derek began but Triss kept her eyes on me and spoke over him like he wasn’t even there.
Trisha
- 03.08.2020
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