A Billionaire's Life Ch. 05

Not that I could complain about their tardiness. Kaitlyn, Taylor, and Mia were still primping themselves as well. Plus, Natalie decided to make it up to me by launching into my arms and giving me a kiss that shook me down to my toes.

From that moment until the next morning, the relationships in our group went through a fundamental change. It was almost as if our trip to Vegas existed in a different universe from the real world. Taylor was no longer my wife. Kaitlyn was no longer Jeff's girlfriend. And we were all free to just enjoy ourselves and each other to the limits of happiness without boundaries or obligations.

We wound up splitting into three groups: Jeff took off with Mia and Rebecca on his arms, ready to party and paint the town while making every man around him jealous for having two gorgeous women doting on his every whim.

Taylor took off in a different direction, one-upping Jeff by having a trio of devoted followers in Charlotte, Denise, and Danny. Denise even seemed to be showing an interest in adopting some of Charlotte's submissive nature, something I hoped her boyfriend Danny would figure out.

And both Natalie and Kaitlyn got to find out what it might be like being my girlfriends for a day. I showered the both of them with affection and little gifts as we hopped from one exotic destination to the next. Natalie saw a sparkling necklace she started drooling over and went into absolute shock when I bought it for her. Then Kaitlyn found a sexy diamond-studded choker for me to get for her as well. The girls then proudly showed off their new jewelry for the rest of the night.

For a brief moment, I remembered the necklace I'd bought for Kate. Then, it had been a subconscious symbol of my affection for her. But here, in Vegas, it was just part of the "girlfriend" fantasy I was living out with Kaitlyn and Natalie. I knew things wouldn't go beyond that. And with the way my relationship with Kate had turned out, it was as if I had a compulsive NEED to playact at boyfriend-girlfriend just to get it out of my system.

Cassandra was with us as well, but she outright refused to let me buy her a necklace. At least she did settle for a passionate kiss.

I finally did stop by the Venus pool at Caesar's with my girls and spent a couple hours relaxing. I laid back and enjoyed being between two beautiful 20-year-olds wearing nothing but string bikini bottoms and the necklaces I'd just bought them. Cassandra was just on the other side of Kaitlyn, and with her huge, round naked melons, she had to fend off more than one flirtatious suitor, despite making it clear she was in my entourage.

For Natalie, sunning herself topless while wearing a few thousand dollars worth of diamonds around her neck proved an energizing experience for the relatively sheltered young girl. And when we got back into the limo, Natalie immediately stripped herself topless again and then fished out my cock, plunging her mouth around it and slurping me madly while Kaitlyn just laughed and patted the brunette's head while Cassandra smiled and looked on.

I'd been quite revved up myself from the pool time spent ogling various naked breasts, and in less than five minutes I was painting Natalie's tonsils with my cum, the last of which she shared with Kaitlyn in a soft kiss.

Dinner was at one of the finest restaurants in Vegas. Natalie couldn't believe we were able to bypass the hour-long wait and just get a prime table. We also got front-row seats for a magic act at the MGM and Kaitlyn was pulled on stage to be the gorgeous girl the magician would flirt with and drool over.

For Natalie, the luxurious limousines and first-class service were a fantasy come true. For Kaitlyn, the day was a brief excursion into our past affair while simultaneously being the first time she was really able to be out and about with me in public. Only Cassandra decided to stay exactly as she was in our real life, as my ever-loyal and loving personal assistant. It was the way she already liked to be, no fantasies needed.

In our separate groups, we entertained and fed ourselves and wound up at different nightclubs until the early hours of the morning. Only occasionally did the others call and check in with Cassandra, purely for safety's sake.

When my little foursome returned to the Sky Villa, Jeff, Mia, and Rebecca were still out, although Taylor's group had beaten us home.

We found Taylor's foursome both in and out of the massive rainfall shower. Denise was kneeling in the tub between Taylor's legs, driving her fingers in and out of the gorgeous supermodel while her boyfriend Danny had Charlotte bent in the other direction, thrusting powerfully into her snatch while his pelvic bones rhythmically slapped against her ass.

Natalie and Kaitlyn got wicked smiles as they pushed me into the bedroom and began to strip my clothes off on the bed. I laughed and wriggled as the two young women both tickled me and tugged at me until I was naked and helpless before them.

They looked at each other and grinned as they readied themselves to spring their next surprise on me, but it was Cassandra who surprised them when she crept up to Natalie and unexpectedly plunged two fingers into the young brunette's pussy from behind.

Kaitlyn had only another second to try and react before Cassandra similarly got up her skirt and past her panties to shove a couple fingers into the young blonde. But once teamed up together, Kaitlyn and Natalie turned the tables on Cassandra, grabbing her and tickling her as they threw her onto the bed beside me and started stripping the statuesque blonde.

But once they got Cassandra fully naked, I looked to my assistant and rolled my eyes towards our young captors. She got the hint and then Cassandra and I went on the offensive. Kaitlyn was nearest to me and after seizing her in my arms, I used my superior strength to flip her over and then begin undressing the young blonde.

Cassandra, similarly bigger and stronger than Nicole, did the same and soon my personal assistant and I loomed over two naked 20-year-olds who were writhing and whimpering for us to let them go.

"But I don't want to let you go," I husked to Kaitlyn.

"And did Nicole ever tell you she had sex with me?" Cassandra asked Natalie, who stopped struggling immediately. The surprise in her wide-open eyes was answer enough.

Cassandra leaned down and husked, "She was the best rug-muncher I've ever met. Period. Think you can top her?"

Natalie grinned at the challenge. Sisters always have a little competitive streak with each other. And with that, Cassandra crawled forward and lowered her trimmed-blonde crotch over Natalie's face.

Meanwhile, I got a positional idea in my head and moved to sit against the headboard, pulling some pillows around my lower back for comfort. Then I pulled Kaitlyn over to me, spinning her around so that she was facing away, and then I spread her legs and dropped her onto my cock.

The young blonde started moaning and riding me, closing her eyes to focus inwards on the sensations I was creating in her pussy. But while she still had her eyes closed, I motioned to Cassandra, who was able to bend forward and with a little shifting, my assistant was able to put her mouth between Kaitlyn's spread thighs and start licking at Kaitlyn's clit even while Natalie was still working on her.

We were a conga line of sex, accompanied not only by my groaning and Kaitlyn's moaning while I rubbed the blonde's tits, but also by the sounds of Taylor's crew screwing like bunnies in the next room.

I was using Kaitlyn's tits as handholds while she slowly rode up and down. Her own hands were busy holding Cassandra's head while the taller blonde ate her out. And further away I could see Natalie gripping Cassandra's ass as she working to try and bring off my assistant in record time.

I never found out if Cassandra considered Nicole or Natalie to be the better rug- muncher. But I did know that Cassandra came quickly and came HARD. When Natalie slid out from beneath the statuesque blonde's hips, her face was absolutely drenched in honey.

Kaitlyn wasn't far behind, the dual stimulation of a thick cock and an agile tongue more than enough to set her off. She chanted, "Yes! Yes! Yes!" before howling an extremely loud "Oh, FUCK!!!" and then came, shaking spasmodically before toppling forwards and off of me.

While Cassandra rolled Kaitlyn over into a sixty-nine, Natalie was quick to mount my recently vacated dick, and I soon got to enjoy the young brunette bouncing in my lap, something I hadn't really been expecting to see or feel again after this morning.

I decided that this little day-trip away from reality was certainly one of my better ideas.

Natalie rode me to her climax and then tapped out when Cassandra showed a deep hunger in her eyes for me. The two young girls had mostly monopolized my cock for the past 24-hours, and my loving assistant was craving some attention.

So while Natalie and Kaitlyn tumbled and groped at each other so much they actually rolled off the bed, Cassandra straddled my legs and then sank herself onto me, leaning forward to kiss me tenderly as I filled up her seemingly little- used pussy.

I felt the happy sigh leave her as we came together, and then she pulled away and buried my head in her enormous cleavage while she started to buck her body up and down.

"Fuck me, Jonathan..." she crooned. "Fuck me..."

I wrapped my arms around her thin waist and let my hands roam freely along her body. And my lips and tongue similarly began to roam freely around her breasts and nipples.

Cassandra was quite keyed up, which turned out to be a very good thing for me since being ridden by both Kaitlyn and Natalie had worn down my stamina. She came first, clawing at my back and whispering, "I love you, Jonathan," into my ear just before she began moaning at the height of her ecstasy.

And then my brain became awash in the knowledge that this was Cassandra, my Cassandra. She was perhaps the person I trusted most in this world, more than even myself or my wife. And she was a woman I could cum inside. After going more than a day without being able to spunk inside a hot pussy, I suddenly felt a powerful pressure in my balls and a desperate hunger to cum.

With a sudden burst of energy, I lifted Cassandra and rolled her over onto her back. She gasped in surprise but started laughing as I maniacally pried her legs apart and then rammed my dick into her once again.

"Fuck me, Jonathan," she crooned. "Fuck me, fuck me, fuck me."

And then my loving assistant held my face in her hands as I thrust wildly like a drunken rabbit, jackhammering as fast as I could until I felt that little tingle and started screaming as I poured out a diluvial torrent of jism straight into the depths of Cassandra's womb.

For a brief moment, I thought about my swimmers futilely searching for an egg that wasn't there. And as I thought about it, I realized I would feel nothing but happiness if somehow, Cassandra became pregnant. I could picture her with a baby bump, FINALLY taking some time away from her work and duties and just spending time with me as a lover. And at that pleasant thought, I felt an extra jump in my cock as I fired another blast, seemingly even stronger than the first one, spewing gobs of semen into Cassandra, so much that I already felt it leaking back out onto our thighs.

Kaitlyn and Natalie had noses for cum. Well, more likely they could hear the obvious audio cues that we were having our orgasms. But either way, the instant I finished shooting and started panting while Cassandra kissed my cheek, one of the girls was pulling my hips out of the way so that the other could shove her head in between Cassandra's thighs and start slurping up my spending.

When my brain returned to me and I was able to look over, Kaitlyn's head was wriggling at Cassandra's crotch and then a few seconds later, she pulled out and Natalie dove in.

There was so much cum and it took so much time for the girls to fish it out, Cassandra actually had another orgasm. And while Kaitlyn finished up with Cassandra, Natalie turned and pounced on my weary cock.

Well... not so weary. As powerful as that orgasm had been, it had only been one. And I hadn't only had one orgasm when around multiple women in a LONG time.

Besides, when the young girls started kissing me and nibbling on my ears, Kaitlyn whined that I hadn't fucked her ass for the entire trip. And then Natalie, drunk on cum and the thrill of a crazy Vegas vacation, shyly asked for me to be her first anal experience.

So then Cassandra took over nursing my erection with her hot mouth while Kaitlyn and Natalie rolled up into a sixty-nine again, this time with a bottle of Astroglide as they worked the lube into each other's ass while munching out each other's snatch.

And when everyone was deemed ready, Natalie eagerly stepped back to watch as I knelt behind Kaitlyn and eased my re-hardened cock up the blonde's back door.

Kaitlyn started moaning "Hurt me," while I buggered her, and Cassandra joined in to start spanking the prostrate blonde and pinch her nipples roughly while I sawed in and out of her asshole. And then I planted my hand against the back of her neck, pushing her down until her legs gave way and Kaitlyn wound up flat on the bed, face-down. While I reamed her out, the young girl was moaning constantly.

"Fuuuuck..." she groaned.

Kaitlyln started drooling and a few tears leaked from her eyes. She was almost completely helpless and unable to move as I had my way with her. And a minute later, her body tensed up with an orgasm, her sphincter clamping tightly onto my shaft. A few more thrusts and I was joining her, squirting my juices down into the darkest recesses of Kaitlyn's rectum.

When I finished spunking into the blonde 20-year-old's ass, I pulled back and arched my back to stretch myself out while Cassandra cleaned me off with a warm washcloth. Kaitlyn was a disheveled mess on the bed, but quite happy.

"Holy SHIT," Natalie gasped. "Is it always like that?"

I chuckled. "No, Kaitlyn just gets off on rough sex sometimes."

"Ohhh, baby..." Kaitlyn crooned into the mattress with a little grin. Meanwhile, Cassandra finished cleaning me up and bent down to start sucking me back to life for Natalie's turn.

"Are you... going to do it like that?" Natalie asked me nervously.

"Oh, no. Not unless you want me to," I told her.

Cassandra popped her head off me and smiled. "I know just how to help." And with that, my assistant crawled onto the bed and lay back. She directed Natalie to move over into roughly a sixty-nine position, although with Cassandra's height and Natalie's relative shortness, the younger girl couldn't quite reach Cassandra's crotch.

Not that it mattered. The point was that Cassandra could reach Natalie's crotch, and as my assistant's tongue began to work its way into Natalie's sodden pussy, the young brunette visibly began to relax.

As they moved into their positions, Kaitlyn managed to crawl over and take over sucking duties on my cock. And a few minutes later, Natalie was suitably relaxed and my dick was suitably re-energized.

I got up and moved to kneel behind the 20-year-old little sister of my ex-girlfriend. And as I hunched forward, Cassandra reached around and spread Natalie's cheeks. I could see the trail of lube that Kaitlyn had already worked inside of her, but I lubed myself up again just to be on the safe side. And with careful aim, I nudged the head of my cock against Natalie's puckered rosebud.

She tensed up at my first touch, but I husked a soft, "Relax..." and Cassandra wrapped her tongue around the brunette's clit.

Her sphincter opened up just a little more and as I pushed, Kaitlyn rolled over and said, "Exhale, Nat. It gets easier."

Natalie exhaled on command and as she loosened, I suddenly was able to push forward. The crown just popped through before Natalie startled at the sensation and clamped down, but I was in. And with a little more pressure, I glided forward until I was balls deep up the 20-year-old's asshole.

"So fucking FULL..." Natalie groaned.

"Wonderful, isn't it?" Kaitlyn swooned.

"Weird... it's good... but weird..." Natalie answered. But then she gasped as Cassandra continued eating her out and then I was pulling back on my cock to restart the pumping sequence.

"Oh... oh... oh..." Natalie started whimpering while Cassandra and I assaulted her body. We both kept our pace slow, but very quickly the pleasurable sensations started to overtake Natalie's "weird" sensations.

"So full... oh fuck me, John... fuck my ass..."

"I'm fucking your ass, Natalie... I'm fucking it," my eyelids half-closed and I started slipping into a trance of lust. After cumming once in Cassandra's vagina and once in Kaitlyn's ass, I knew I could last a good long while. So throwing any semblance of control to the winds, and with a firm grip on Natalie's hips, I started to drill her with more powerful strokes, increasing steadily until I was able to lunge without significant restraint, slamming myself forward until my pelvis crashed against Natalie's asscheeks.

"FUCK ME!" Natalie cried. "FUCK MY ASS!"

And so I did. And soon, perhaps more due to Cassandra's tongue on her clit, Natalie detonated. Her anal muscles clamped down on me so tightly that I couldn't even move. And she screamed loud enough to echo throughout the suite.

Humorously, at the same time I heard Rebecca scream, "FUCK MY ASS!!!" somewhere in the distance.

I chuckled and just kept going.

For a few minutes, Natalie was still lost to the aftershocks of her orgasm. She moaned and whimpered and her head just lolled around uncontrollably while I pistoned in and out of her now lewdly-stretched sphincter. Cassandra continued to munch on her and as I circled my hands around to cup the young brunette's tits, she started to become more alert.

"Oh, gawd. I can't believe you're still fucking my ass..."

"Believe it," I grunted and slammed her a little harder.

"Oh, fuck... oh, fuck... I think I'm gonna cum again," Natalie moaned.

"Cum, baby. Cum for daddy," I growled and Natalie actually jerked when I said that.

"Ooh, you like that? You like daddy skewering your tight ass, Natalie? I'm fucking it. I'm fucking your ass. I'm reaming you out, baby girl."

"Ohhh..." Natalie groaned and started ramming her hips back at me.

I finally started to feel the urge to cum. So pitching my voice lower and speeding up my thrusting, I crooned again, "Cum, baby. Cum for daddy."

"I'm gonna cum! I'm gonna cum with your dick up my little asshole! Arggghhhhh!"

Her anal muscles clamped down again as a second, more powerful climax ripped through Natalie's body. And this time, when she screamed, "FUCK MY ASS," it was loud enough to drown out any other sounds.

And then the trembling in Natalie's body and my own rapid thrusting set me off as well. And with a loud grunt, I slammed forward into Natalie's twitching asshole and let loose all the cum I had left in my balls.

Natalie's hips spasmed a few times as her orgasm ran its course, and then her torso collapsed flat on top of Cassandra, who just held her firmly. But I still held her hips in my hands as I spunked out the last few drops of jism into her bowels. Only when I released my grip did Natalie completely go limp.

Cassandra then took a final few slurps of Natalie's feminine nectar leaking out of her pussy. And once I pulled away, Kaitlyn crawled over and shoved her tongue between Natalie's asscheeks, licking up my male cream leaking from that hole.

We were all silent for a few minutes, just catching our breath. And then I moved around and sat by Natalie, patting her head. "You okay?"

"I'm going to be sore," she answered gingerly. "But I've no regrets."

I smiled and rubbed her cheek.