John Billionaire Ch. 02

After dropping the phone into the seat next to me, I lay my head back and sank another two inches down. Me and my stupid heart. First it wouldn't let me let go of my pain stemming from Nicole shutting me out. Then it wouldn't let me fly away and have wild sex for a week straight. I was feeling thoroughly depressed.

The minibar then caught my attention, and I reached out to grab a tumbler and select an appropriate mind-number. Hell, no sense having a minibar in your car if you're not going to use it. And I wanted to drink so much I would forget my own name. Forget the name, forget my life, just forget everything for a little while.

"Driver, I don't want to go home just yet. Let's go for a ride."

***

Cassandra was waiting for me when I got in the door. "Jonathan!" She stood up from the living room sofa and immediately walked over to me.

Earlier in the day I was feeling depressed. Now, I was feeling depressed AND drunk. I guess I looked so pitiful that she didn't bother with a 'how are you doing?' or a 'what's wrong?' She simply reached out and hugged me in the middle of my foyer.

She'd never hugged me before, but I wasn't about to comment on the non- professional action. Automatically, I felt myself sag into her embrace, a relief pouring over me that some other human being might understand what I was going through. She had to fight just a little to keep me upright in her grasp. I sagged just a little too much and after pounding several shots of toxic waste in the car, I was already rather trashed.

After a minute or two of feeling her warm hug, she directed me back towards my private quarters. I staggered along, supported by Cassandra with my arm over her shoulders. She was surprisingly strong for such a slender woman. Finally, she got me onto my comfy couch in front of the big TV and I just let my head loll against the backrest.

Somewhere off the side I heard her say, "Coffee... and make it strong" followed by the click of the intercom turning off. And then Cassandra was by my side once again.

She had already cleaned herself up for bed. It made sense since it was past 11pm and I'd been 'riding' around New York for hours. She was clad in a satin silver pajama set, with long pants and a button-down blouse. But I don't think there was much underneath there as the blouse contoured against her very full breasts with the hint of her nipples. Her blonde hair was pulled back into a ponytail, her makeup gone and she smelled of shampoo and soap. It was a very pleasant smell, especially after the rancid taste of alcohol had been the last thing filling my nostrils. To top off the ensemble, a delicate pair of thin-frame glasses were perched on her nose.

Like a concerned mother, she leaned over me and rubbed the top of my head while I half-focused on her face and half-drifted in drunken stupor. No words were spoken for a few minutes; none were needed. She was just there for me.

Then Dorothy came in with a tray: small pot of coffee, little silver pouring cups for milk, cream, and sugar. Cassandra fixed it up for me and then held my back as I leaned over to start drinking.

I managed a nod of approval, and then Dorothy left silently, closing the door behind her. I simply closed my eyes and returned to my coffee, holding it with both hands and letting the warm vapor steal their way into my nostrils.

Once the caffeine started to percolate inside me, I managed to awake. At that point I realized that Cassandra was still with me, quietly supportive with eyes attentively watching.

As if seeing her for the very first time, I managed a weak "Hey..."

"Hey..." she murmured back, still stroking my back.

Instinctively, I leaned towards her as if to kiss her. It just felt so comfortable being around her like this, as if she'd been a part of my life for many years. And then I realized what I was doing and pulled back suddenly. Even in my drunken state, I knew it wouldn't be proper.

There was a flicker of disappointment in her eyes as she similarly backed away and sat up straight. At least I wanted to think it was disappointment.

After a moment of just looking into my eyes, she fixed me with a concerned expression and said, "So I'm guessing things didn't go so well with Nicole?"

"You would be guessing correctly."

"I'm sorry..." And she really meant it.

I saw in her eyes total acceptance. No judgment, just understanding and sympathy. And somehow, someway, I felt safe with her. That's when the waterworks opened up.

I was crying, and the next thing I knew my head was buried against her shoulder as I sobbed without restraint. She just hugged my head against her, quietly cooing and whispering words I couldn't comprehend and yet understood.

Cassandra held me patiently, waiting for me to let it all out. The warmth of her body was a soothing salve for the pain, and her arms cocooned me to shield the world away. I wasn't feeling happy, but I did feel better.

She felt so comfortable that I actually started drifting off to sleep. When she noticed I'd been still for some time, she turned and whispered, "Let's get you to bed."

She helped me up and I walked unsteadily towards the bedroom. But on the way, I tasted my own alcoholic breath mixed with the coffee. I detoured to the bathroom before realizing that she was still following me.

"Thank you, Cassandra. For everything. But I'll be fine. You don't have to wait for me."

She folded her arms beneath her breasts and leaned against the wall. "As long as you don't mind, Jonathan, I'd rather stay and make sure you get to sleep."

I managed a smile and then turned to the sink. There was no self-consciousness as I brushed my teeth and washed my face. A full shower, however, would have to wait. I was just too damn tired.

Cassandra held my hand as I staggered into the bedroom, shedding my clothes down to my boxer shorts as I went. She even pulled back the covers as I slid inside and promptly collapsed into an awkward sleeping position. And when she sat down on the mattress beside me, one hand on my head, I felt a calm peace wash over me. I had a guardian angel.

The last thing I remembered, before sleep blanked out my consciousness, was rolling over and holding Cassandra's waist in my arms as my head pillowed against her side. And then I was off to enjoy my dreams.

***

***SUNDAY***

I blinked and felt totally at peace. There was a dull ache in my head, familiar as the remnants of a mild hangover. But besides that thick cloud, I felt great. There was a happy energy flowing through every inch of my body.

No wonder, I had a warm body snuggled up to me. Actually, I was spooned around behind her, my left arm snaking beneath her neck and clutching her tightly against me. Long, blonde hair smelled wonderful in my face, and the tight ass rubbing against my crotch felt even more wonderful.

My right arm was wrapped over the top of her, and somehow my hand had slipped beneath the hem of her pajama top and I had a very full naked breast palmed into my hand. I felt a smile cross my lips as my fingers cupped at the round firmness, a nipple being teased to erection by the soft rubbing of my hand.

It felt like the wonderful bliss of a happy morning after passionate lovemaking. Only... I couldn't remember the lovemaking part. Actually, I wasn't sure where I was or who I was with.

Glancing around, the bedroom looked half-familiar. But I didn't know where I was. Whose place was this?

The woman with me stirred a bit in her sleep, and my hand slipped out of her top while I turned to try and get my bearings, a momentary surge of panic welling up inside me. But then her head turned and I saw sweet Cassandra's face. And everything came back to me.

For the first few days I had known Miss Cooper, my personal assistant, there had been nothing but cool, professional detachment between us. A part of me even resented her as a symbol of the radical changes that had been forced upon my life. But there had been a warm affection buried underneath that evidenced by the blush that came into her cheeks every time she called me 'Jonathan'. And now as I looked at her face, all I could see was Cassandra, a friend.

Well, a gorgeous friend... a gorgeous friend with great tits that I'd just been fondling. And she was gorgeous friend who was now turning around, turning until her head was pillowed on my left shoulder, her face just inches from mine as she smiled in her half-awareness. Her left arm wrapped around my torso while her left leg came up and stretched across my hips. The position felt so intimate and comfortable.

I couldn't help it. More to the point, I didn't want to stop myself. I leaned my head down and kissed her forehead. She just hummed and hugged herself closer to me.

A moment later, her eyes slowly blinked their way open. And when she was able to focus, she found me looking right back at her. I could sense her feelings through those eyes. They were grey when she was serious and a light blue when she was happy. Those eyes were light blue now.

Her lips met mine halfway as I experienced one of the softest kisses of my entire life. And when I let my neck rest as my head fell back against the pillow, she followed me down before snaking her tongue into my mouth.

We lay in bed for the next ten minutes, just cuddling and kissing. It felt so natural and unhurried. My hands found their way underneath her pajama top once again as I stroked the sleek track of her spine, reveling in the sensations of her naked skin beneath my fingertips.

The heat of our kisses started to increase, the flicker of passion stoking higher and higher until it had become a roaring fire. Cassandra gasped as I suddenly rolled us over until she was flat on her back and I was leaning over her, devouring her mouth with my own.

We were suddenly both in a hurry, moving especially fast after the languid pace of our kissing had been. She was tugging at her own pajama pants, jerking them and her panties down while I similarly tried to get my shorts off. She got caught up for a moment around her knees when I couldn't get out of the way and my shorts got snagged on my feet. But then we finally flung the offending garments away and dove back into each other's arms.

We were both naked from the waist down as I settled my hips between her legs. My elbows were planted on either side of her while I gazed right down into her eyes. No words had yet been spoken. None were needed.

Her hand was wrapped around my erection and she tugged it forward, guiding me into place until the crown was nestled in her moist folds. And when she removed her hands to place them against my biceps, I pressed forward, both of us moaning as the shaft slowly burrowed its way deeply into her wet tunnel.

Cassandra's long, lithe legs wrapped around my lower back, crossing her ankles and pulling me into her while her mouth gaped erotically into a silent scream. And after a minute, I had fully buried myself into her.

We stayed there, just savoring the first moments of being so intimately joined to another person. Now that we'd achieved penetration, the slow, languid pace came back to us, urgency melting away like so much stress after a long day. And then our lips found each other once again.

Now we were kissing like we'd done when we first woke up, only I was inside of her. And after a long bout of tongue wrestling, we broke for air and I backed up my head and backed up my rod simultaneously.

She groaned as my body took up the familiar rhythm of lovemaking. In and out steadily, unrushed. Her hands came up and held my cheeks in wonder, watching the expressions contort my face. A wide smile spread across her face, in part because of the pleasurable sensations coursing through her body, but also partly from seeing the pleasurable sensations running through MY body. There was a laugh in her irises now as we enjoyed this physical intimacy and slowly screwed the morning away to our hearts content.

Cassandra was still holding my head when the first waves of orgasm began to crest up and down her spine. Her eyes tightened and she arched her back off the bed, a truncated wail suddenly bursting forth as if she had not been expecting it.

Expected or not, the reaction from her nether regions was immediate, her pussy muscles clamping down on me as she flooded our union with a heavy dose of girlcum to add additional lubrication to the mix. She looked so devastatingly sexy at that moment, and I had to see more.

This whole time, her pajama blouse had remained buttoned up. Now as she panted in the aftermath of her first orgasm with me, I paused to slip the catches on every single button. I forced myself to slow down and perform methodically, lest I get frustrated and start ripping it off her. But at last every button was undone and I flung the blouse open, baring her perfect tits to my gaze for the very first time.

They were volcanic mounds, large and firm and round and I felt my cock get even harder at the mere sight of them. Cassandra giggled as she felt my reaction vibrate within her. I couldn't help it. She really was a blonde bombshell who was absolutely stacked. And I was making love to her.

Well, I had been making love to her. But now as my hormones kicked into overdrive, I began fucking her.

Cassandra let out a full-blown laugh now as my body surged up into motion, thrusting and pummeling her with brute force. She held onto my arms again and pulled my body into her with her legs on every thrust, fucking back at me as much as I was fucking her.

"Fuck me, Jonathan!" she cried. "Fuck me, Jonathan! Oh, Jonathan! It's sooo good! Oh, fuck, fuck, fuck.... Fuck me, Jonathan!" They were the first words either of us had spoken all morning.

I was more than happy to oblige her, ramming my cock to the hilt on every stroke. I paused only to duck my head down and smother my face into her cleavage, my lips nipping and sucking at those wonderful globes of heaven. And after a couple more minutes of pounding away at each other, Cassandra's body began spasming out of control.

She lost the rhythm, and then I lost the rhythm, but neither of us cared as our hips automatically knew the dance as we both crescendoed towards the climax of our morning. I dropped my head to the pillow next to hers, my lips rubbing at her neck as she clutched my chest against her own, crushing her tits into me.

"Fuck me, Jonathan! Fuck me, Jonathan! Don't ever stop fucking me!"

My hips kept up their own thrusting as did hers, and then suddenly she had driven her hips up into the air, holding them there as she cried out and bit down on my shoulder, squealing in ecstasy as she came.

"Fuuuuuck! Oh, I'm cumming. I'm cumming! Cum with me! Cum inside me! CUUUUUM!"

And I was cumming. My crotch crashed into hers and held there as I unloaded both barrels of sperm, blasting what felt like gallons of cum straight into the back of her womb. Load after load of creamy goodness poured out of me and filled my sexy assistant's pussy, so much that I could feel it leaking out from around our joining.

And when we were both finished, our bodies crashed back down to the mattress in a weighted thump, no more sounds except for heavy breathing as we tried to catch our breaths. Off to the side, I thought I heard another moan. But then Cassandra's sweet voice brought my attention back.

"Wow, Jonathan... you were fantastic..." Cassandra complimented me.

"Thank you," I groaned. "You were quite amazing yourself..." And I couldn't help myself from diving my face back down into the valley of her amazing cleavage. So big, so full, so round, so utterly intoxicating.

"You seem to like my tits," she laughed.

"Oh yes..." I breathed. "But these are so much more than just tits. These are works of art."

She laughed again and then wrapped her legs around me, not letting my cock exit from her. She held my cheeks in her hands once again, pulling me so she could look right into my face above her. "Good morning, Jonathan." From her expression she looked like she had another orgasm just saying my name.

"Good morning, Cassandra," I replied with warmth in my voice.

"You have no idea what long-term fantasies you fulfilled for me this morning." And she meant it. She was positively glowing.

"Oh, really?" I thought back for a moment as our bodies relaxed and I finally slipped out of her. "Did any of them have to do with my name? I noticed you were screaming my name quite a bit. Did you know a Jonathan in some other life?"

"Actually... yes." Her blush was back. Not the blush of a woman in heat, but the shy, nervous blush she'd first shown me when I asked her call me 'Jonathan' for the first time. "It's kind of a long story."

"You know I want to hear it." Even though we were no longer joined, I moved up on the bed and cuddled close to her until I was sitting half-upright, with Cassandra's head pillowed on my chest.

She let her fingers come up and touch my skin in front of her face while she began her story. "What you don't know about me is that my mother was also a personal assistant. We were from Australia of course. But soon after I turned 5 years old she got the job in America on the recommendation of a family friend. I stayed with my grandparents another few years but when the job started looking permanent, she brought me here to be with her. My mother was very good at her job and she also lived on-site. So I literally had my childhood from eight years old growing up in the main residence of my mother's employer. From the time I arrived, I was doing little things to help her out and learning all the little details that occupy the lives of... well... you rich people."

She laughed as she said that, spurred on when I tickled her over that last comment. Then she continued on.

"When I turned fifteen, I was hired officially as a junior assistant. I was my mother's 'backup'. Now there's no such thing as 'part-time' for a job like this, but I had fewer responsibilities to allow me time for my education. After graduating college, I went out and worked for a wealthy banker on Wall Street for a few years. I actually left that position to come work for you. I had a very... personal reason."

There was a knot in my stomach as I started to realize where this was going.

"You see, Jonathan, my mother's employer was the late Jonathan Kendall, your father. I grew up in his house. I grew up working for him. And he was the only father figure I had in my life. After he died, I was uniquely suited to working for you. Despite my age, I am quite experienced with the portfolio; businesswise, I know everything that's going on. My mom chose to retire rather than take another position."

There was a nervous worry in the back of my head as I thought things through. "That explains some history behind you and Jonathan Kendall. But it doesn't explain your fantasy."

"Well..." her blush was back. "My mother was sleeping with Mr. Kendall. Their affair lasted many, many years. Though he had various other girlfriends and high-profile celebrities, she was always there. I remember sneaking around the house and listening to my mom screaming 'Fuck me, Jonathan!' And when you first asked me to call you 'Jonathan', the first thing that came into my mind was hearing her voice screaming that name. He was a handsome man, and as a young teenager I had quite the crush on him."

She paused and looked up into my eyes while rubbing at my chest. "I used to imagine it was ME screaming 'Fuck me, Jonathan'. You've sort of fulfilled a long- time 'daddy' fantasy if you will."

I felt a new stirring of arousal in me and a smile stole across my lips as I let Cassandra's fantasy sink into my brain. Her mother and my father! We were just continuing the family tradition!

But then I realized how sex and biology lead to procreation. Cassandra's mother was sleeping with Mr. Kendall. And he was the only father she ever knew. The knot in my stomach tightened and the worry in the back of my head turned to full- blown panic. "Wait, if Jonathan Kendall is MY father and he was the one sleeping with YOUR mom, then that makes you my-"