Erotic Story: Tom Billionaire Ch. 02


Tom Billionaire Ch. 02

-- CHAPTER 2: Montauk --

****

*-- SEPTEMBER (10 MONTHS AGO), MONTAUK, NEW YORK --*

I grinned, looking down at the giggling infant who was rolling on his back with all four limbs in the air. Jonathan Kwong, Junior (or "JJ" as we all called him) was not quite 11 months old, and not quite able to walk on his own. He certainly kept trying, standing himself up against the couch and then bravely launching himself outwards. But he could only manage a step or two before collapsing to the lushly-padded carpet. For some reason, falling in this manner amused him to no end, hence the delightful giggling.

From my spot on the couch, I bent forward and hooked my son beneath his armpits to lift him upright. Once in the air, his little legs flailed around, trying to locate the ground. But when I held him up in front of his mother, his legs quieted as he broke into a goofy grin, accompanied by a pleased, "Muhh..."

Taylor sighed happily. "I know I've said this a million times, but he's sooo cute."

I put my own face next to JJ's, smirking at my wife. "That's because he looks like his _father_."

"We've been over this." Taylor raised an eyebrow at me, brushing back a long bang of her son's nearly black hair. "He has your eyes, but the nose and mouth are all mine."

Actually, it was true. JJ's eyes had the trademark almond shape from his quarter-Chinese ancestry, and they were the same blue as mine. But amidst the chubby cheeks and recessed baby-chin, JJ's nose was a bit smaller and pointier than mine. And his mouth was shaped with a distinctive curve like Taylor's. I looked over at my wife, having previously committed the perfection of her face to memory, and I smiled, thanking my lucky stars for letting me be married to such a gorgeous creature.

Even at 32, Taylor was just as beautiful as she'd been when I first met her in college. Time and pregnancy had added a couple of pounds to her slender frame and filled out her cheekbones just a bit, but her dark blue eyes were just as hypnotic as ever. And extensive work with our personal trainer, Rebecca, had gotten her body right back to pre-baby fitness. Taylor had even walked in the Victoria's Secret Fashion Show last December, just two months after giving birth to JJ.

"Face it," I stated proudly. "You know he's the most handsome boy in the world because he resembles ME."

My wife rolled her eyes. "I still think *you're* cute because YOU remind me of HIM!"

The two of us laughed, which got JJ to start laughing again. And moving in, I nuzzled my son's cheek from one side while his mother nuzzled him from the other. This, of course, provoked more squeals and giggles. And I already knew I would never get sick of the sound.

Eventually, we let JJ go to crawl after an empty water bottle that had become his favorite toy. He retrieved it, and then after seating himself upright, he promptly began chewing on the plastic cap.

A new voice broke in behind us. "Heeere's Joey!"

I turned my head to look over. I have to admit, my eyes first went straight to the glorious pair of tits hanging forward. It wasn't my fault; Ashlyn was bending over and she was wearing a scoop-necked top, putting those big melons on full display. But no matter how sex-addled my brain could be, my gaze was immediately drawn even lower, for the reason Ashlyn was bent over was because she was setting our daughter down on the floor.

"Dah... Dah!" Her hair in dark brown pigtails pointing up and to the sides, Josephine "Joey" Scott was a few weeks past her first birthday. With arms outstretched, she waddled forward on unsteady legs.

I opened my left arm in invitation, and my daughter picked up speed as she neared me. But as she sped up, she also lost her balance. And about three feet away she tripped and suddenly pitched forward.

I was expecting this, and smoothly I leaned forward to catch her against my chest. Laughing as if she'd meant to trip all along, knowing full well that I would catch her, Joey stood up against me and started patting my arm with what seemed like a spastic penguin flap. "Dah!" she repeated.

"Joey!" I greeted pleasantly, tapping the little toddler on her forehead. And then I tapped myself on the forehead, stating, "Dada."

"Dah! Dah!" she cheered.

"See! She's got it!" I exclaimed enthusiastically, looking up at my girlfriend.

She leaned over us, still giving me an eyeful of those big tits. The copper redhead still wore her hair long, although it was pulled back into a single ponytail, and thus did not obstruct my view. And what a view.

Ashlyn Scott, at 26, was in the prime of her beauty, and that wasn't just my opinion. Despite giving birth just over a year ago, she was never more in demand than she was now, modeling for top designers like Christian Dior and Chanel, among many others. And her recent motherhood had made her the Number One ranked MILF in the world according to Maxim Magazine, even ahead of Angelina Jolie. Unlike Taylor, she'd skipped last year's Victoria's Secret Fashion Show. But this year, she was on the cover of their latest catalog and expected to headline the new show in a few months. From alluring face to bodacious rack to freakishly long legs, she had the kind of body that made men drool, made women buy lingerie to MAKE their men drool, and she practically had me drooling now.

From the smirk tugging at the corners of her lips, I was sure my girlfriend knew EXACTLY what she was doing. And when I looked up at her face, she gave her chest a little extra jiggle for my benefit. But that smirk was up in her eyes, as well. "You wish Joey had it. I think you're just peeved that she'll clearly say 'mama' on cue."

"Mama!" Joey cheered, craning her face up and backwards to look at her mom upside-down.

"See." Ashlyn grinned, clapping at her daughter to positively reinforce the behavior.

"Dah!" Joey then turned back to me.

"She's got 'dada' down too!" I insisted.

"Not yet. That's just a plain 'dah'. She says 'dah' to everything, from her stuffed frog to the chair to the TV."

"Dah!"

"Taylor," I turned back to my wife, who was still rolling around the floor with JJ. "You heard Joey! Tell her!"

"Ashlyn's right," my wife replied without even looking over.

"Traitor," I muttered beneath my breath. Then putting on another wide smile for my daughter, I stared right into her big blue eyes and stated slowly, "Daa... Daa. Dada."

Joey went silent and just blinked at me, not saying a thing.

"Daa... daa," I repeated, tapping my thumb against my forehead in a motion that supposedly matched American Sign Language. "Daa... daa."

"Don't take it personally," Ashlyn said soothingly. "It's not like she doesn't recognize you."

"Daa... daa," I said one more time.

And to our utter and complete surprise, Joey straightened up and stated, "Dada!" Then she leaned forward into my arms, pressing her cheek against my chest.

"Hey!" I chirped, looking up at Ashlyn, who looked just as surprised as I felt. "Dada!" I cheered happily.

"Dada!" Joey squealed again, buoyed by my enthusiasm.

"She's got it!" I raved. This time, Ashlyn didn't contradict me.

And then out of the blue, JJ propped himself up against my opposite shoulder, having just climbed me as easily as he climbed up the side of the couch. And in a quietly serious voice, he stated, "Dada."

My eyebrows shot up and I looked straight at Taylor, who also now looked surprised as hell.

I couldn't be happier in the world. Hugging him with my other arm and beaming proudly, I stared my little boy in the face and repeated one more time, "Dada."

JJ just looked at me oddly, glanced back at his mom, and then one more time looked right into my eyes. His right hand came up... and slammed down on my nose.

"Oww!" I barked, backing my head away.

JJ just broke into a big grin, giggling. And looking back for his mom, he muttered, "Muh..."

****

I would have loved to stay in the family room and roll around the floor with my kids all day, but there was work to be done. And I told my family such.

"Work? What work?" Taylor complained. "Last I checked, you still had more money than we could spend in three lifetimes."

I shrugged. This was an old argument. "It's not about the money. Are you still modeling for the money?"

Taylor sighed. She continued doing it because she loved it, and because her friends were all in the modeling world. "Of course not. But it's not like you hang out with those guys socially."

I shrugged again. And thinking of the big Hollister acquisition we were close to completing, a predatory grin spread across my face. "Different thrills, honey. Different thrills." I kissed my kids on their cheeks, then kissed their mothers on their lips, and stood up to leave.

Ashlyn sighed and stood up as well. "I should go, too. Good time to catch a ride into town." The statuesque model stood up and looked over at me. "Give me ten minutes to freshen up?"

I nodded. "Sure. We've got time." While Montauk was technically on Long Island, it was at the most Eastern edge, a good two-and-a-half hour drive on the roads, not counting traffic. So when not in a big hurry, we often 'carpooled' in the helicopter rather than send it back and forth to Manhattan on multiple trips.

The two of us stepped away from the infants, who were now crawling around a set of soft rubber cubes together. We briefly watched Joey grab a purple block with the number 4 on one side, the letter D on another, and various other designs like 4 dots on the remaining sides. JJ promptly moved in and grabbed for the same block, but Joey held it back and started nibbling on an edge. Ashlyn and I beamed at each other and backed away.

"I got them, Mr. K," the last adult voice in the room chimed in. Jada Sharpley was 20 years old, blonde, hazel-eyed, and very pretty. She was also the daughter of my VP of Acquisitions, Robert Sharpley. And for the past few months, she'd been the kids' nanny.

Oh, we had another, more professional nanny. Evelyn Holbrook was a mid-fifties ex-Montessori teacher who had known Dorothy for years. But while we could easily afford a second nanny to watch over the two infants, that second spot had become something of a revolving door over the past year. One nanny just didn't get along with Evelyn as the two constantly fought over alpha status. Another didn't get along with _Taylor_. And our most recent one, despite rigorous screening by Cassandra's contacts, actually tried to steal some of my financial records.

We were almost at the point of just giving up trying to find a second, since the kids were getting older and easier to handle. And with Taylor scaling way back on her public appearances and modeling workload, her personal assistant Charlotte had a lot more time to spend with the babies as well. But just before we got that far, Jada Sharpley entered our lives.

I'd been bitching about these babysitting difficulties with some of my JKE execs back in June when Bob told me his daughter was looking for a job. Jada had dropped out of college, disillusioned with the whole "academic" thing. But supposedly she was a smart kid and had extensive babysitting experience throughout her teen years.

I had been skeptical. A 20-year-old college dropout didn't seem the type to be hardworking and dedicated to caring for my children. But Bob asked me for the personal favor just to get Jada in a stable environment with some basic responsibilities, and I agreed to at least let Cassandra interview her. If nothing else, we might be able to give her a job with fewer responsibilities, for a while at least.

But surprisingly, she passed Cassandra's interrogation with flying colors. The young girl had taken to JJ and Joey immediately, and they to her. And she'd been a live-in nanny ever since.

This morning, I watched Jada drop to the floor and slide over to the children. Joey looked up and saw that Ashlyn and I were leaving. The little toddler waved a short goodbye to us. And then smiling, she picked up a Sesame Street book and hopped right into the young nanny's lap.

"Have a good day," Jada waved before taking the book in her hands and beginning to read to Joey.

Smiling one last time at them, I turned to Ashlyn and confirmed, "Ten minutes?"

Ashlyn gave me a lopsided grin. "Ten minutes. I promise."

****

As Ashlyn headed upstairs to her room, I went to a wall panel and typed in the commands to call the helipad. I told my pilot to prep for departure, and then I headed off down the hallway toward The West Wing.

Cassandra sat behind the desk in my (her) office, her nimble fingers darting like lightning over the keyboard. A bluetooth headset with boom mike was perched over her right ear, and she jabbered something about debt ratios while continuing to type and also greet me with a nod of her head and a twinkle in her eyes.

Even though we had yet to go into the office, Cassandra was already "at work". Somehow, she ran my household, managed my personal affairs, and supervised my executives all at the same time. She did so with a smooth efficiency absent of significant error, somehow cramming a week's worth of work into a single day every single day of her life. In short, she was absolutely incredible. And she was so much more to me than just a personal assistant.

Moving myself behind the desk chair, I leaned down until my chin lightly rested on her shoulder. Peeking my eyes at the screen, I made sure it wasn't anything *too* important before reaching over and hitting the power button to turn the monitor off. I then grabbed the end of the boom mike, pulling it off Cassandra's ear and stated quite clearly, "This is Jonathan Kwong. She'll have to call you back." And I hit the END button on the desktop phone to hang up the line.

Cassandra chuckled. This kind of interruption was not uncommon for me. After briefly hugging her neck from behind and kissing my assistant's cheek, I pulled back and spun her chair around so that she would face me.

Batting her eyelashes, the bodacious blonde turned her sky blue eyes up to me and purred in that sultry Australian drawl, "Good morning, _sir_... How may I... _serve_... you?"

I grinned and took a single step forward.

Grinning, Cassandra reached to my belt, deftly opening it as well as my slacks. She pulled my hardening cock out, jacking me with her left hand as she let her tongue loll out to swirl around my mushroom head. And then she looked up at me again and asked, "How much time do we have?"

"Ashlyn's coming. She promised it would take her ten minutes to change."

My assistant grinned, showing off pearly white teeth while continuing to stroke my naked erection. "Thirty minutes it is!" she crowed. And then she ducked her head back down, suckling on my pole and not stopping her forward progress until her nose was pressed up against my crotch, humming to let her throat muscles massage my shaft.

Cassandra was good. She was *really* good. To be perfectly honest, Taylor initially was the more skilled cocksucker. But even though Taylor was my wife, I probably spent three times as many hours alone with Cassandra, going back and forth to work as well as my various business trips. In the four or so years she'd been my personal assistant, I could count on one hand the number of times she'd been away from me for any extended length. And of all the times I felt the need to unwind and blow off a wad in relaxation, Cassandra was by far the most likely to be ready and willing by my side.

In short, the statuesque blonde had already given me a thousand blowjobs in our time together, and that's not an exaggeration. That kind of practice could only lead to knowing _exactly_ how to make me happy, and that's just what Cassandra did.

"Holy _shit_..." I groaned, feeling my knees buckle.

Up until now, Cassandra had been sitting in the desk chair to perform her duties. Without missing a beat, she lifted up and yanked the chair around her with her right hand, continuing to stroke my shaft with her left. I felt the front edge of the seat hit the back of my calves, and with a gentle push, she sat me down. And then I was free to let my body relax and receive the oral ecstasy she was bestowing upon me.

Kneeling before me, Cassandra blew me to brink of eruption. But before I came, she pulled away and bit the inside of my thigh hard enough to leave a hickey. She'd told me a hundred times that she belonged to me, but this morning my assistant was marking me as HER property. And when I looked down at her, there was no mistaking the self-satisfied smirk on her pretty face.

I let her bask in that momentary position of power over me before I stood her up and roughly slammed her facedown over my desk. I dropped her panties down around her ankles, and without having to be asked, Cassandra stepped out of them. The wadded up silk would remain in my pocket for the rest of day. I then lifted the back of her neatly-ironed business skirt. And with deliberate aim, I sank my dick into her from behind.

"Fifteen minutes, sir," Cassandra grunted, turning her face to the side and letting the cool surface of the wood press against her cheek.

My hands gripped her hips, my thumbs stroking the fleshy thickness of her asscheeks. And with a self-satisfied smirk of my own, I thrust my way forward.

"Ughhhh..." she moaned.

"Ungh..." I grunted.

"Fuck me, Jonathan," Cassandra hummed. "Fuck me."

I fucked her. The clock on the desk had both analog and digital readouts. Watching the analog second hand gliding along urged me on, and every change of the minute display on the digital clock pushed me into another gear. I'd started off with slow, languid strokes, feeling the cushiness of Cassandra's ass meeting my pelvis over and again. But as the minutes counted down, my pace sped up.

"Five minutes, sir..." Cassandra groaned at length. She was panting, her breath coming in heaving gasps, matching the rhythm of my thrusts. I felt her vaginal muscles quivering against me. Likely, she could have already cum a time or two by now. But like me, she was waiting for the final countdown.

"Four minutes, sir..."

My ab muscles burned. I was stroking at a rate of about a thrust every second, feeling Cassandra's cunt relaxing to allow my entry and then clamping down as I retreated.

"Three minutes..."

Cassandra's voice was weak. Sweat was dripping off her brow, and she'd pulled her arms back so that her palms were flat on top of the desk, pushing herself back at me with each lunge.

"Two... minutes..."

And two strokes a second. In-Out. In-Out. So. Fucking. Good. So. Fucking. Tight.

"One... one minute..." Cassandra's voice was a plaintive gasp. Her jaw hung slack, and her cheek was pressed against the desk again. Like a fish out of water, her jaw opened and closed slowly as if she didn't even realize she was doing it. And her eyes had started wobbling in their sockets as my three strokes a second pounding was shaking her entire body.

I watched her mouth open to try and count down the final seconds. She couldn't. Her voice was gone, she wasn't even moaning anymore. The only sounds coming from her were the audible squishes of her oversaturated pussy every time I pushed my rampant cock into her body. But in my own head, I felt the pressure inexorably build.

Five... four... three... two... one...

Liftoff.

"AAAAAAAAAUUUUUUGHHHHHH!"

Cassandra had no concept of time in that moment. Her eyes were vacant orbs staring off at nothing, not at the clock nor me nor the room around us. But she certainly *felt* the splatters of jism bursting deep inside her loins as *I* came inside her. And the instant that sensation filled her mind, she let go of her precious control and let herself just FEEL the pleasure.

"AAAAAAAAAUUUUUUGHHHHHH!" she screamed again as I gripped her hips even tighter, holding myself at maximum depth while my cock spat out wad after wad of spunk into her body. I imagined a million tiny tadpoles racing through her fallopian tubes, desperately searching out an egg. And the thought spurred my testicles to instantly manufacture more sperm on the spot to fill her with.