John Billionaire Ch. 04

"Oh, fuuuuuuck," Lindsay drawled as she felt each inch of my shaft parting her tight vagina and in the end she grunted as I bottomed out. "Why do I even bother fucking my boyfriend? He can't fill me the way you do."

"Oh, no you don't," I admonished her while I ducked my head to tongue at her conical nipples pointing straight up perkily. "I've got enough romantic complications as it is. Let's just have fun, shall we?"

Lindsay just grinned at me, her cute face awash with excitement. "Fuck the shit out of me, John."

"With pleasure." And then our hips were banging away.

Meanwhile, after bringing Kaitlyn to one orgasm with her fingers, Taylor had moved down the bed to bring her extremely talented tongue into play. And as my hips slapped against one teenaged nympho's pelvis, I heard the other teenaged nympho squeaking in wonderful agony as the best rug-muncher in New York ate her out.

Taylor glanced at me for just a moment, her violet eyes issuing a challenge. And from then on it was a race to see who could make their teen cum first. I had to admit, I was at something of a disadvantage. No matter what the skill of the lover, for speed orgasms direct access to the clit was something of a requirement. And no matter how well I drilled Lindsay, I would never be able to stimulate that love button the way Taylor could by licking at Kaitlyn.

After thirty seconds, I pulled out and quickly flipped Lindsay over doggy-style. And before she could catch her breath I had re-inserted myself from behind. My right hand reached around to our joining and found the skinny redhead's hard nub of a clit, prominently protruding conveniently for my wet fingers to find. My left hand wrapped around the underside of her left breast, tracing the sensitive nerves. The new position let me stimulate her directly, but the only thing that could let me win was my familiarity with Lindsay's pleasure spots.

Taylor, meanwhile, was quickly figuring out Kaitlyn's pleasure spots despite only meeting her this morning. And when I saw Taylor harshly shove three fingers into Kaitlyn's juicing cunt, I realized she had figured out Kaitlyn's penchant for rougher sex.

I was hammering myself against Lindsay's asscheeks, and she was wailing a constant "Fu-, fu-, fu-," unable to complete the word before my hips knocked the breath out of her. Her inner muscles tightened around me, and for the briefest moment I had hope.

But then Taylor popped a finger into Kaitlyn's anus, and the race was over. Kaitlyn's legs flew up and clamped around Taylor's head, squeezing tightly while her back arched so high her shoulders got airborne while she planted on her head. The scream that ripped its way out of Kaitlyn's throat was deafening, and carried on and on and on.

By the time Kaitlyn's legs fell limply to her sides, Taylor was gasping for air and her face was soaked. Kaitlyn just moaned "I think I'm in love," and then started giggling.

Her peals of laughter only got stronger as Taylor crawled up Kaitlyn's steaming hot body and blubbering playfully, she rubbed off her fluid-covered face into Kaitlyn's big, perky cleavage.

Meanwhile, watching and - more importantly - listening to Kaitlyn's climax had both Lindsay and I at the edge of our own orgasms. Once I lost the race it no longer became an issue about cumming faster, but about cumming better. I flipped over one of Lindsay's legs without exiting her, so that she was laying on her side while I straddled her lower leg and dug even deeper into her spasming channel. With one hand I held her upper leg against my chest while the other hand kept up its assault on her clit.

And at the moment I felt my own balls uncoiling and readying themselves to burst, I popped my own finger into Lindsay's ass, winking at Taylor, and as her body stiffened I felt my dick let go and begin to spew forth its offering into her clenching snatch.

Lindsay's eyes rolled up and her head twitched spasmodically as her climax spread through her body. She was almost oblivious to me pumping a gallon of cum inside of her. And when it eventually passed, she just closed her eyes and sagged against the mattress.

Kaitlyn and Taylor were cuddled together for the moment, rubbing noses while the blonde teen kept touching at the brunette model's face as if in disbelief while Taylor tried not to wince too hard at the gentle caresses. Kaitlyn's eyes were wide as she soaked in the experience, not knowing if it would ever happen again. I had to admit, Kaitlyn really did look like she was in love. At least, she never really looked at me that way.

I pulled out of Lindsay with a wet plopping noise, and then our mingled cream began to ooze out of her while she lay panting. Taylor looked over, and asked, "Do you want to switch?"

I honestly did. Variety is what keeps life interesting. But Kaitlyn looked so happy with Taylor for the moment. I would feel bad about taking her idol away.

"Stay there, Taylor," a new voice interrupted. "I've got it."

Cassandra leaned against the wall behind me, her blue-grey eyes simmering. Her gaze was locked in on the pearly fluids leaking out from Lindsay's pussy. She paused to remove her blouse first, leaving on the thin bra doing its best to restrain her bulging breasts. I moved out of the way, and then she stopped to kiss me before lowering her tongue to slurp out Lindsay's and my love cocktail.

The redheaded teen, already suffering from sensory overload, couldn't even get her limbs to function properly as she lay twitching on the bed, feeling Cassandra's expert tongue carving out her insides.

Meanwhile, I moved along to the other pairing. Taylor immediately took charge, seating me comfortably against the pillows and headboard. And then she directed Kaitlyn to bring me back to hardness

Kaitlyn's green eyes flashed before she sucked me into her mouth, and then Taylor's lips were in her ear, huskily whispering instructions as Kaitlyn bobbed her head up and down my rising member.

Kaitlyn was an apt pupil. After improving tremendously in the few weeks we'd known each other, now she was pleasuring my pleasure-stick in ways she'd never been able to accomplish before. And with careful directions and quick reactions, she not only brought me to full hardness in rapid time, but I felt the pangs of desire to ejaculate already building inside of me.

I was about to let Kaitlyn suck me to completion in her mouth. And yet, I wanted to fuck something. I lay here, with four unbelievably hot women writhing around my bedroom. I wasn't going to settle for anything less than at least two more orgasms. And I wanted them to count.

It was my turn to take charge and I moved Taylor until she was flat on her back. And then gently prying Kaitlyn off me, who didn't want to stop, I directed her to lie on top of Taylor and the blonde eagerly leapt into position, immediately capturing Taylor's mouth in a searing kiss as they pressed together, chest to chest. For a moment, they had a hard time getting their tongues into each other, their tits so firm and large it took a little Lego-like positioning to get comfortably close enough.

I settled in behind the girls, standing at the edge of the bed and looked down on the four holes, each seeming to wink at me and plead to be the first. I started by spreading Kaitlyn's asscheeks and rubbing the spongy head of my cock in the wet folds of her pussy.

"Ooh, fuck me, John," Kaitlyn pleaded. But just when she thought I was going to plunge into her, I lowered down and stuffed the first few inches of my cock in between Taylor's gaping vaginal lips.

Taylor stiffened at first, pressing Kaitlyn's body upwards while their tits crushed together, and then she relaxed to allow me to glide all the way in. I groaned happily at the wonderful feeling inside of her hot tunnel of paradise.

Kaitlyn spread her legs to the side and managed to grind her clit down against Taylor's pubic bone, whimpering in pleasure as she masturbated herself on Taylor's body. Meanwhile, the two of them continued tonguing and licking at various ears and necklines while I plugged away at Taylor, doing my best to hit her g-spot inside.

But just when Taylor's hips started bucking back at me, I pulled out, spread Kaitlyn once again, and burrowed my cock into the teenaged vixen's saturated pussy. She was so lubricated with orgasmic fluids that I slid right through her normally restrictive tightness and bottomed out in one thrust.

I split her so quickly that she instantly lifted her head and cried out a fresh climax, Taylor suckling at her throat as she screamed. I kept thrusting even through Kaitlyn's orgasm, driving her to higher and higher plateaus of pleasure while her pussy muscles clamped and squeezed in a riot of abuse around my shaft.

When her cries died out, I pulled out and pushed my way back into Taylor once again, filling her quickly and then rapidly pumping as she gasped and moaned while clutching the blonde nymphet to her neck.

I felt kind of bad. Kaitlyn had cum twice and Taylor had yet to get off. This had to be unfamiliar territory for the normally sex-crazed goddess. And so I worked extra hard to grind against Taylor's sensitive inner nerves while Kaitlyn was lavishing attention upon Taylor's breasts and face.

And in the end, I was rewarded with a wriggling climax out of Taylor as she vibrated and came, dumping a fresh load of girlcum into our union. This time, I was already moving on to the next part. I rotated my shaft around inside her while she writhed around the bed, and I found the nightstand was within my reach. Popping the drawer I pulled out the bottle of Astroglide.

I let my cock enjoy the aftershocks of Taylor's orgasm inside of her spasming pussy. Meanwhile, I applied a liberal amount of lube to Kaitlyn's anus in front of me. She just wiggled her butt cheeks in anticipation. And then I pulled out to squeeze several globs into Taylor's asshole and then coat my cock.

The short breather gave me enough time to let the sensations crawling up and down my dick subside. Now I knew I had enough stamina for a good, long fucking. Once again, I played around with both girls, teasing them to see which hole I violated first.

This time I went with the blonde teen, her asscheeks so firm I could barely dent them when I gripped them. And when my crown popped through her sphincter, she groaned and then reached back to spread her cheeks wider and allow me deep into her chute.

Kaitlyn gasped at my entry and then whimpered, "Ooh, John. Fuck my ass. Violate my little body."

Glancing to the side, I could see Cassandra and Lindsay had formed their own 69, fully naked. Lindsay was crawling all over Cassandra's longer and curvier body, exploring the huge tits and sweet snatch while trying to remain composed with the statuesque blonde's tongue buried inside of her.

I pulled out of Kaitlyn and then aimed lower. And now Taylor reached her hands down to hold herself open for me as my cock speared forward and into her ass. After thirty seconds I switched back, filling the little girl's ass and giving her a good pumping before pulling out again and re-entering Taylor. And then I was ramming the hot model while I watched Kaitlyn's dilated asshole trying to close back up slowly.

I waited and waited, watching the tight muscle contracting millimeters at a time while I plugged Taylor's backside. And just when it seemed like Kaitlyn's anus recovered enough to close, I pulled out and slammed my cock through Kaitlyn's anal gateway once again.

She screamed at the sudden penetration, and then I pulled a hand back to spank her cheeks while I continued reaming her out. Kaitlyn lost all ability to focus on Taylor and instead crouched on all fours, just trying to endure the pounding I was giving her ass as she cried out from the rapid thrusting through her overstretched nether passage.

Taylor wasn't exactly soothing her either. Her hands pulled roughly at Kaitlyn's nipples and her teeth left scoring marks across the delicate girl's neck. Taylor's nails even raised a few small welts on the teen's back. I could only imagine what was going through Kaitlyn's head as her primary male lover and her female idol ravaged her body together. And very quickly Kaitlyn was shrieking out her climax

I grinned seeing movement to the side and then Kaitlyn's shriek was muffled halfway as her eighteen-year-old best friend, Lindsay, leaned in and shoved her tongue down Kaitlyn's throat. This didn't dissuade the blonde completely, and her muzzled squalling continued to pour out as she was now being pawed at by three people at once, her orgasm building and building rather than subsiding.

Cassandra, meanwhile, lowered her head down to Taylor so they were upside- down relative to each other. And with her palms against Taylor's cheeks, my beautiful personal assistant planted a firm Spider-man kiss on the hot brunette.

Kaitlyn's orgasm finally gave out, and so did her limbs. The light teen collapsed onto Taylor's body, her anus spasming a few final times around my cock.

I couldn't handle much more. And so exiting Kaitlyn and letting her tumble off to the side, I buried my pecker into Taylor's ass and began thrusting away in my final sprint.

"Aw, fuck, fuck, fuck," Taylor chanted while I reamed her out.

Once Kaitlyn rolled off into Lindsay and the two teens nuzzled and cuddled with each other, I was able to focus all my attention on Taylor. She'd been pressed underneath the blonde teenager for so long that she needed to stretch her limbs out for a moment. And while I continued violating her asshole I pulled on her legs and hoisted them over my shoulders, pounding away and seeking nothing but my release. My hands roughly gripped her hips, still sore and bruised from last night, and Taylor yelped in fresh pain while simultaneously moaning in pleasure, the result a strangled cry directly into Cassandra's mouth.

Cassandra was already massaging Taylor's arms and breasts while they maintained their liplock, and even though I wasn't trying to induce orgasm, Taylor stiffened and came.

The sudden clamping of her ass was all I needed to spill over the edge, and with a roar of triumph I slammed as far as I could up into Taylor's bowels, and the head of my cock exploded as it blew wad after wad of cum deep inside of her trembling body.

"Fill me, baby!" she screamed while I fired over and over, ejaculating my heavy cum-bombs into her anal depths for the second time in just a few hours.

In the end, Taylor's head lolled to the side as she panted with exhaustion. She was in good shape, a must for any fashion model. But she wasn't used to supporting a blonde eighteen-year-old on her chest for that long, especially in her weary, injured state. Fortunately, her two biggest fans soon came over and soothed her. Lindsay wanted to get her share of kisses she'd been missing while tied up with me and Cassandra. And Kaitlyn wanted to get to the naughty cocktail of sperm oozing out of Taylor's ass.

Cassandra, meanwhile, dragged me off to the shower. "Let's get you cleaned up."

Even after all the fucking, once inside the shower I was still mesmerized by the huge wonderfulness of Cassandra's boobs. Once the hot water was spraying on them and giving them a warm glow, I couldn't keep my hands or my lips off of them.

She chuckled while I suckled, and her hands were busy soaping up my body and cleaning me up. Two minutes later, when she was satisfied with my cleanliness, Cassandra sank to her knees and held my prick up in her face.

"Miss Cooper, what do you think you're doing?"

"I'm getting you ready for my turn, sir," she purred. And then her face descended and I was once again in the warm paradise of a woman's mouth.

It had been days since I'd made love with Cassandra. And before that one Sunday, it had been much longer before that. I appreciated so much how she gave so much of herself into my life and asked for so little in return. And a burning desire, coming from deep in my gut more than the lust from my loins, had me desperate to join with her.

Cassandra's oral ministrations had me hard again in record time, considering I'd just had two wonderful ejaculations. And when I felt the surge of energy flowing through my body I pulled out of her mouth, lifted her to a standing position, and then pressed her back against the wall as I captured her lips with my own.

Cassandra half shrieked at the cold marble against her skin but also moaned into my kiss. And then I'd pinned her hands against the wall behind her as I smothered her with my affectionate lust and rubbed my chest against her tits. My cock nudged up against her belly, and with my hands still pinning her to the wall I tried to get my dick lined up to thrust inside of her. And then once I got into position, I suddenly seized her hips, lifted her up, and impaled her on my shaft.

"Aaaaah!" she wailed as pulled her crotch all the way down against mine so I was balls deep in Cassandra's wonderful pussy. But despite the temptation to stay and fuck her in the privacy of the shower. I shut off the water and then stepped outside. I had an orgy to return to.

Cassandra clutched my neck and back with her legs crossed behind my hips for support. I held her asscheeks in my palms and managed to grab an oversized, fluffy towel on the way out the door. I only had enough time and balance to fling the towel into something resembling a flat rectangle before I sank to my knees, planted Cassandra on the towel, and began rutting her into the rug.

We were on the floor next to my bed, and Taylor peeked her head over the edge to watch us while I drilled Cassandra. "There you are, baby! I was beginning to worry you'd forgotten about me," she pouted, her violet eyes dancing.

Cassandra blew her a kiss before closing her eyes to simply enjoy the feeling of physical pleasure shooting up and down her body.

Taylor, meanwhile, squeezed her eyes shut and moaned from something behind her. I could only imagine what she, Kaitlyn, and Lindsay were up to on that bed. And despite the wonderful feeling of making love to the goddess beneath me, my mind was already wandering to whatever other sexual combinations and positions I could take my pleasure from.

I guess Cassandra was right. My male, sex-controlled brain, told me to love what we were doing. And by extension that made me think I loved her... right? But inside my head, I could already hear her reminding me: "When you're fucking Taylor you think you love her. When you're fucking Nicole you think you love her. And I know when you're fucking me you think you love me. So understand that you love what we are doing. And that is enough for me."

Cassandra was so accepting and so wonderfully compatible with me. Despite the abundance of female flesh I found my world shrinking down until there was no orgy, there was no bedroom, there wasn't even a floor nor towel beneath her. There was only Cassandra and me, floating in empty air. And there was only the shared orgasm ripping through our bodies as we came together and I filled her body with the liquid expression of my love. And as her arms pulled me close to her, our sweaty bodies melding together while my cock perfectly molded itself inside of her pussy, spitting out jet after jet of hot cum to splash against her insides, I understood.

I would never get tired of making love to Cassandra. I knew without a doubt that as my dating relationships came and went, she would always be with me. There was a corner reserved in my heart for her. Maybe she would never have the whole thing, but neither could she ever lose that corner.

***

Kaitlyn and Lindsay had left. Cassandra occupied herself with some sort of work, primarily to leave me and Taylor alone.

Out of clean clothes and other personal items, Taylor now readied to take her leave. She'd been here longer than expected already.