A Billionaire's Life Ch. 04

I pumped her for a couple of minutes before she began moaning, "Fuck me, Jonathan. Fuck me..."

Bracing my right hand against the desk, I reached around her body with my left hand. I pulled her blouse free of her skirt and then slid my arm inside the blouse, digging my fingers beneath her bra so that I could cup a round, swelling breast. Meanwhile, Cassandra slid her own hand down to diddle her clit, fighting to find a steady rhythm with my long thrusts jerking her body once every second.

At last, she came with a quiet, "Fuck meeeee..."

As I felt the spasms of her inner muscles, I slammed my hips forward twice more before holding myself in and then felt the unbelievably relaxing sensation as my dick began to spew out my pent-up load. I panted and wriggled my hips as I continued spunking inside her.

"Ohhh... Jonathan..." Cassandra sighed as she felt my jism splattering against her inner walls. And then we both went quiet so that there were no sounds but our heavy breathing.

I pulled out and then grabbed a tissue to wipe myself up before tucking my deflating penis away. Soon, I was zipped up and ready to go.

It took Cassandra another minute before she managed to push herself off my desk and get to her feet. She reached for the tissue box herself, but I reached out and stopped her arm. "No. I want you to feel me squishing inside you all day."

Cassandra shivered and her eyes fluttered. Then she husked a soft, "Yes, sir." With that, she pulled her panties over her crotch and I immediately saw the white fabric darkening as the material started to get wet. She fixed her skirt and then checked her appearance in the wall mirror.

"NOW we're late, Jonathan."

***

As it turned out, Taylor was even later than we were. So Cassandra and I slid into a booth and she squirmed a bit as she felt my cum still leaking out of her.

When Taylor did arrive, she had company.

"Hello John, Cassandra," Ashlyn nodded to us nervously, then slid in beside Taylor. Charlotte sat next to Cassandra.

"Ashlyn," I nodded politely but glanced at Taylor. My wife was still upset that her good friend stood by Martin Dean post-rape, and I wasn't aware they'd had any contact recently. Everyone at the table was distinctly aware Taylor had been avoiding her for a little while.

Taylor explained, "Ashlyn was in the area and asked to meet up with us. I didn't see any real reasons not to. I may not approve of her boyfriend, but she's still my friend."

Ashlyn smiled weakly while I glowered at her, still angry at Dean. But I bit my tongue and said, "Of course. Friends are friends."

Ashlyn shrugged. "I talked to Kate. She sounds much happier now. I wanted to thank you both for what you've done for her. I tried pressuring the agency into helping Kate out, but Taylor here is a LEGEND, and she's got a lot more clout than I do."

"Kate got the contract?" I asked.

"Yep. Just this morning." Ashlyn blushed and looked down. "And... she told me what you've done for her, John."

I couldn't help but smile at my own recent memories of Kate. "My pleasure," I said sincerely.

Ashlyn giggled. "Sometimes a girl just needs to get laid to be free of her doldrums."

"My man is DEFINITELY good for THAT," Taylor smiled and then leaned in to hug me. But when her face went to my neck, she went rigid.

I arched an eyebrow and looked down at her. Taylor didn't look upset at all, but more curious as she began to sniff me. "What?" I asked.

Taylor's nose kept twitching. "You smell like sex," she said with a sly grin on her face. And then she glanced over at Cassandra, who blushed and continued squirming in her seat.

With that wordless communication I STILL haven't figured out, something passed between Cassandra and Taylor and then my wife's eyebrows shot up. "Excuse me," Taylor said demurely and then before I realized it, she'd slipped underneath the table.

"Taylor. Taylor?" I asked hurriedly to the tabletop.

We all go the answer a moment later when Cassandra suddenly jerked in her seat and then sagged backwards, moaning softly. "Ohhh..."

I had no doubt my wife was under the table, slurping my cream out of Cassandra's twat. And just then, our waiter arrived to take our orders.

Ashlyn beamed at me. "You certainly lead an interesting life."

***

Eventually, Taylor crept back into her seat and Ashlyn slid over the extra Cosmo she'd ordered. But there was a droplet of my cum on Taylor's chin, and Ashlyn deftly scooped it up with her finger.

Then before anyone could react, Ashlyn popped it into her mouth and began sucking while fluttering her eyes at me. "Mmm..." she moaned.

I pushed her teasing from my head and we settled in for the usual gossip and conversation.

One subject that was tiptoed around was Ashlyn's boyfriend, Martin Dean. Taylor didn't even want to hear his name, and the few times our conversation turned in that direction, things became awkward.

Once such instance was when Ashlyn asked about how my business was going. I glanced at Cassandra and went quiet.

"Oh, sorry," Ashlyn apologized. "You and Marty are going head-to-head again, aren't you."

I nodded. "Your boyfriend is playing fast and loose with his money."

"Jealous?" Ashlyn couldn't resist getting in the dig. "He's doing quite well for himself."

"I know," I couldn't resist answering. "But he's taking a lot of risks."

"Johnny..." Taylor pleaded with a hurt voice.

"Sorry," both Ashlyn and I said at the same time. We switched subjects.

Eventually, our lunch wound down and it was time for everyone to head off. Ashlyn made Taylor promise to bring Kate along on their next shopping trip. The gorgeous redhead hadn't seen her best friend these past two weeks since she and Dean had flown off on an impromptu vacation to get out of town after the rape incident.

Taylor took it a step further and invited Ashlyn to come by the house whenever she wanted. Either way, they'd find a way to get Kate and Ashlyn to hang out again.

We all parted with platonic hugs and kisses, although when Ashlyn hugged me, she copped a feel of my butt and whispered, "I'm jealous of Kate."

And then we went our separate ways.

***

Upon returning home, I finished up some quick household decisions and paperwork with Cassandra and then went to my bedroom to change. Taylor had separated from us on arrival and I wanted to check in with her.

For all her confidence and poise, I knew Taylor had been suffering during the lunch with Ashlyn. The visible reminder of Dean had been making her uncomfortable, and I knew it took a lot of active focus on her part to think of her friendship with Ashlyn and lock away her anger at Dean.

But Taylor wasn't in our room nor our usual family area for relaxing. Rebecca and Mia were sunning themselves by the backyard pool, but Taylor wasn't with them either.

I was starting to muse on the practicality of embedded GPS tracking devices, something subdermal a requirement given how often my ladies were naked, when I rolled my eyes at my own stupidity and then headed for the Dungeon.

The Dungeon was a room in the basement, next to the wine cellar. Originally intended as an extra storage room, Taylor and Charlotte had instead outfitted it with an array of BDSM equipment immediately upon moving in. It wasn't the sort of thing they needed Mia's decorating expertise to do.

I walked quickly along the concrete floor and went to the heavy wooden door with the barred window (Taylor had custom-ordered the door from some Medieval props catalog). Tugging on the iron ring, I pulled the door open and went inside.

Sure enough, Charlotte was laying face up on a long platform. Her hands were cuffed and pulled back behind her head by steel chains wrapped around a wicked-looking winch. From the stretch in Charlotte's arms, I think Taylor had coiled the winch one notch further than usual.

Charlotte's nipples were clamped with alligator clips and attached to a string long enough for Taylor to grasp and tug on every now and again. She was blindfolded and moaned at the ceiling every few seconds, her voice echoing through the room.

At the other end of the platform, the pretty brunette's legs were clapped into a twisted version of gynecological stirrups, spreading her feet up and apart which gave Taylor free access to thrust the double-ended strap-on dildo into Charlotte's sodden pussy. Both women were fully naked, save for the strap-on harness.

And all the while, Taylor held a slender whip in hand, crisscrossing Charlotte's body with red welts. From the way the red puffiness was just starting to form, I imagined they'd only been going for a few minutes.

The heavy door was squeaking as I opened it, another nod to Medieval times, and Taylor turned her head around to me with flames in her eyes.

"Letting off some steam?" I asked.

"Yeah," she said unenthusiastically. "But it's hard to work up real anger when I know Charlotte wants this."

I glanced at Taylor's pretty assistant, whose entire body was flushed and sweating, a little smile on her face even as she panted for air. "Maybe you need someone you're not so sure wants to be abused."

"You volunteering?" Taylor arched an eyebrow at me.

I went stiff. "Oh, uh well, not really," I sputtered.

As I was saying that, the door creaked open again and Kate walked into the room. "Oh, my..." she breathed when she saw the scene before her.

"Hiii, Kate..." Taylor turned and husked, the other end of her strap-on still imbedded inside of Charlotte.

"Taylor..." Kate said warily. She was flushed pink, whether from embarrassment or excitement I wasn't sure. "I, uh, I heard you guys were back and I wanted to thank you for helping me get that contract."

Kate stared at the floor, which led me to believe she was embarrassed by what she saw in front of her. But she rubbed her thighs together, which made me think it was more than that. "Cassandra told me you were probably in this room. She, ah, didn't tell me what kind of room it was."

"That's okay," Taylor said and then turned to tug on the string connected to Charlotte's nipple clamps and then flicked her wrist to lash out with the whip. The brunette assistant moaned and then squirmed, trying to hump herself onto Taylor's fake cock despite being unable to stretch further. "You're not really interrupting," Taylor finished.

"Well..." Kate continued and then glanced up at me for a second. "I really wanted to thank you... thank you both... for the opportunities you've both given me."

I smiled warmly, reassuringly and said, "You're welcome."

But Kate continued. "And... I was hoping I could find a way to express that thanks," she said to the floor. She went quiet for a few seconds again, and I clearly saw her rubbing her thighs together once again.

"Uh, Taylor," Kate started hesitantly. "Did I overhear you saying something about a volunteer?"

Taylor flashed her eyes at me and then back to Kate. The platinum blonde stood there nervously, quivering either in fear or excitement. I still couldn't tell.

"Uh, well... you really don't OWE us anything, Kate. Remember?" Taylor began as I watched the flush of arousal turn my wife's skin pink as well. "But if you're interested, we can certainly show you how this game is played."

Kate smiled shyly and canted her head to the side, absently stroking her exposed neck. "With... with both of you?" she asked with a touch of excitement in her voice.

I shared another glance at Taylor. "Sure thing," I said.

"What do I need to do?"

Taylor slid out of Charlotte and saucily began to walk towards us, her fake cock dangling from her crotch obscenely. "Johnny, why don't you let Charlotte warm you up. I'll get Kate started."

I bowed to the wishes of the master and headed over to the table, stripping along the way. Behind me I heard Taylor say, "First, you need a safe word..."

Perhaps proving that I wasn't a true Dominant, I went to the winch first and relaxed Charlotte's bonds by a notch, but she moaned in annoyance and didn't stop until I re-stretched that extra notch.

After stripping myself naked, I fumbled around for the right lever, desperately hoping that I didn't hit the wrong button and pull Charlotte's arms out of their sockets. I wasn't used to the equipment, but eventually I found the catch that lowered the entire apparatus downwards. And once Charlotte's platform was practically on the floor, I kicked a leg over and straddled her chest, aiming my half-hard cock at Charlotte's blindfolded face.

Eventually, we managed to work it out, and Charlotte happily sucked on my shaft, using only her lips, tongue, and head-bobbing to work me up towards a good erection.

Once Charlotte got me hard, I slipped off of her and circled around back into Taylor's previous position between the brunette's outstretched legs. Fiddling with the vertical controls again, I pulled Charlotte's platform up until she was at a good height, and then I sank my cock into her sopping wet pussy.

Charlotte moaned when I began to thrust inside of her. She moaned even harder when I reached out for the string and began to tug her nipple clamps as well.

"Okay, Johnny," Taylor called. "Finish off Charlotte and then come over here."

While continuing to thrust into my wife's assistant, I turned my head to look. Kate was strung up naked with her hands strapped to a horizontal trapeze. Her ankles were cuffed just above the floor. And while Taylor had ditched the strap-on, she was walking around her holding a white wand that was a little over a foot long.

At first, I thought it was a strange kind of club or crop, as Taylor was lightly slapping it against Kate's ass and trailing it along the platinum blonde's thighs. But when Taylor moved it to Kate's crotch and held it, Kate started shaking and I realized the white wand was actually a very big vibrator.

With a little grin on my face, I turned my attention to Charlotte, reaching around her raised legs and getting a firm grasp on the tops of her thighs, very close to her crotch. Pinching down, I went ahead and gripped her as hard as I could, knowing the young woman wouldn't mind the pain, and I used the leverage to really launch my hips into her.

"Ohhh! Ohhh! UNGHH!!!" Charlotte moaned and came, her body jerking against her wrist chains as she reflexively tried to hump herself at me to no avail.

I rode out Charlotte's storm without cumming, and when she finally went still I pulled my hard erection out of her. Quickly, I moved around and hit the release on the winch, slackening the tension on Charlotte's handcuffs. Then as her arms reflexively curled in, I went around the platform and freed her legs.

Charlotte just rolled over onto her side and curled into a fetal position, panting heavily. Worried, I bent to her face, but she gave me a weak smile to let me know she was alright. Satisfied, I kissed her forehead and patted her butt before crossing the room to Kate and Taylor, my hard cock bobbing eagerly with every step.

I arrived just in time to see Kate and Taylor come together in a passionate kiss. Seeing my short, dark-haired goddess of a wife locking lips with the pretty, platinum blonde momentarily blew my mind, and it almost blew the top off my cock. But I squeezed my inner muscles and held off, relaxing a bit to watch as Taylor moved down Kate's body, kissing her way across the blonde's neck before reaching Kate's perky breasts.

As Taylor's tongue snaked out and wrapped around a nipple, she also brought up the white wand and pressed it into Kate's sex. The young blonde's eyes popped open and she groaned in pleasure, her hips jerking forward as a quick orgasm swept through her.

The bucking motion shoved an extra three inches of the wand into her twat, and then Kate began screaming as the climax rose up and crashed over her body.

Still not satisfied, Taylor bent onto all fours on the rubber mats beneath the apparatus. And then crawling forward, she leaned in to begin tonguing Kate's clit while pushing the white vibrator in and out of Kate in a slow stroking motion.

For a moment, I just stopped and stared at Taylor kneeling with her head wriggling in Kate's crotch. Watching your woman eating out a pretty girl has got to be towards the top of every man's fantasy list whenever they imagine a threesome. Fucking your wife while she eats out a pretty girl might just be THE top. And seeing my wife's perfect ass facing back at me was just too much of a sign. Taylor probably had intended for me to join her in titillating Kate, but when I saw Taylor's pussy lips glistening from behind, I just had to get in there.

My wife actually shrieked in surprise when I suddenly appeared behind her. And she had no time to react before I'd gripped her hips and slammed my cock into her pussy from behind, familiarity and experience assuring my aim would be true.

Kate was watching as I began pumping into my wife with manic intensity, smiling in the afterglow of her orgasm. It didn't hurt that Taylor still held the white vibrator six inches into the blonde's pussy.

Taylor began groaning, "Oh, SHIT. Fuck me! Fuck me, Johnny!"

And Kate started urging me on, "Fuck her! Fuck that slut!"

I was only too happy to comply. And with my wife's tight clenching pussy wrapped around my shaft and my own battered control after fucking Charlotte just recently, I soon reached my limits. Howling with glee, I rammed my cock into Taylor a few more times and then started blasting out gobs and gobs of cum into her.

Taylor herself was pretty primed after teasing both Charlotte and Kate, and the moment she felt my semen pulsing into her, she clamped down and came herself, groaning straight into Kate's crotch.

Taylor's arms began to wobble as I finished up shooting cum into her snatch. And when I pulled out, she collapsed face first. An idea came into my head, and I started looking around for certain objects.

By now, Charlotte had managed to right herself and stand up. I called out to her and pointing at Taylor, I ordered, "Suck that out of her and then feed it to her with your mouth."

"Yes, sir," Charlotte shivered and then moved to obey.

Meanwhile, I moved to the wall-mounted electronic controls for Kate's trapeze, lowering her until her feet touched the floor again and then lowering it further and moved it forwards a couple of feet. At first, Kate tried to maintain her balance, but once moved forward far enough with her ankles still chained, she fell to her knees and hunched forward with her arms still suspending her chest off the ground. Perfect.

I walked around in front of Kate and then raised an eyebrow to her when my crotch was in her face. "Lick me hard, slave."

"Yes, Master," Kate hummed and then reached her mouth forward to slurp me in.

I grinned at the word "Master". Maybe I *did* have a little Dominant in me. But just as I started to look around for whips and riding crops, Taylor opened her eyes and warned, "Don't leave any marks. She's got a modeling gig, remember?"

"Oh, right," I nodded and then smiled as Charlotte finished munching on Taylor's crotch and then lifted up to press her lips against my wife's and let out the deluge of semen.

Soon, the vision of Charlotte and Taylor kissing combined with Kate's excellent fellatio brought my cock back to life. An idea came into my head then, and after pulling out of Kate's mouth, I beckoned to my wife.

Taylor came and I leaned in to whisper my idea. She grinned and nodded. And then while my wife went and retrieved the necessary items, I circled behind Kate, held her ass in my hands, and then plunged my dick into her pussy.

"Ohhh... yes, John!" Kate moaned. "Oh, I LOVE your cock!"

I loved her pussy. And soon, I was also going to love her ass. But for now, I pistoned in and out of her twat, my hips meeting her ass with pleasantly meaty slapping noises.