A Billionaire's Life Ch. 05

Between that sight and Karen's surprisingly decent blowing, I was back in action. With the girlish excitement that made Kaitlyn so familiar, my blonde kitten sat up and pushed me onto my back before straddling my hips. Her eyes fluttered as she slowly sank down onto my upright dick, and I moaned softly while I felt myself being enveloped by her warm tightness.

Kaitlyn then smiled at Karen and said, "I want to ride him for a bit while you sit on his face. Then we can keep swapping back and forth until we jerk him off all over our faces. Okay?"

Karen quickly got to her knees and slid herself over me while facing back towards Kaitlyn so the girls could paw at each other. "Sounds like fun."

***

As typical for this vacation, I woke up in the early afternoon. Consciousness seeped into my brain slowly, and through my still-closed eyelids I could see the red haze of sunlight. And as various nerve endings awoke along my body, I felt a familiar sensation.

Someone was sucking on my dick.

Before the sandy crust would allow my eyelids to open, I smiled and reached up a hand to touch her head. And under my fingers, I felt the tight locks of her braids as they ran past her scalp and longer towards her shoulders.

The braids were a dead giveaway. Without opening my eyes, I let myself smile in recognition before I cracked my eyelids open and the afternoon light blinded me for a few moments. Eventually I was able to focus on the blonde braids and lower down see Kaitlyn's smiling face stretched wide by my cock in her mouth. I frowned to see her wearing one of the hotel bathrobes instead of having an unfettered view of her nubile body.

The sound of a toilet flushing momentarily distracted me and I turned to see Karen, wearing another one of the hotel bathrobes, come out of the adjacent bathroom and wash her hands. Then she stood and leaned against the wall, folding her arms over her chest as she watched the blonde head rising and falling in my lap.

"Morning," I cheered.

"Morning," she smiled. I was hit with that half-recognition once again. I was CERTAIN I knew this girl from somewhere.

But then Kaitlyn gave me quite the good lick along the underside of my rod, and all higher brain functions abandoned me. I tilted my head back and groaned at the pleasure, stroking Kaitlyn's head as she fellated me.

Karen decided to join in, crossing the room and then sliding stomach-down onto the bed beside her new friend. Obligingly, Kaitlyn popped off and offered my cock over.

Happily, Karen took it in hand and then swallowed the first three inches of me before slowly working the rest into her mouth. Honestly, Karen't technique wasn't very good. But the thrill of being blown by a fresh, cute brunette I'd never had before last night was more than enough to keep me happy.

The two 20-year-olds passed me back and forth for a few minutes, building me to my climax slowly until Kaitlyn's expertise finally brought me to the edge. Her green eyes swiveled over to the brunette, flicking at my cock quickly and Karen smiled greedily.

Just when I was about to blow, Kaitlyn handed me off and started jerking my shaft, pulling me over the edge just as Karen surrounded me with her mouth.

A knock sounded at the door just as I started cumming. I was too lost in the delirium of orgasm to react and Karen was busy swallowing the copious amount of semen I was flooding into her mouth. Kaitlyn might have said something, but she was intently focused on stroking my shaft and telling Karen to save some for her.

The last few shots flew out of me and then Karen pulled off while holding a hand in front of her mouth as she tried not to lose the pool of cum she was holding in. Kaitlyn quickly sealed off Karen's mouth and then the two of them were exchanging a very sloppy kiss, globs of jizz leaking out while they sparred with their tongues together.

At that point the knocker just decided to open the door. Danny, fully dressed, poked his head in and saw the situation, his eyes going wide. "Oh, sorry guys. Didn't mean to interrupt."

Karen turned around and shrugged. If she felt embarrassed to be seen swapping my cum with another girl, she didn't show it.

Kaitlyn just verbalized, "No problem."

"Uh, Nat," Danny started. "Denise and I were just wondering if you wanted to get going. Taylor offered to get us breakfast but I was thinking we should check in with the others before they start worrying."

Nat. Something triggered in my memory and automatically I started scanning through my memory again. Nat? Nat... OHMIGOD!

My eyes flew open and I sat up quickly. "Natalie?!" I exclaimed in shock, staring straight at 'Karen'.

The young brunette's eyes flew open and she turned to her friend. "Danny!" she complained shrilly.

Hungover, he looked confused for a moment before realizing his slip. "Oh, uh, sorry."

I sharpened my focus on the pretty girl. I'd only met her once, and was unsure of my memory, but I was pretty sure it was her. "Natalie Gellar?"

Natalie blushed and reached up with a finger to scoop a glob of my cum off her lower lip. "Hi, John."

Kaitlyn just looked back and forth between us a few times. In confusion, she asked, "Do you two know each other?"

Natalie said "Not exactly" at the same time I said "We met once."

We both paused to let the other speak, and then Natalie started up again. "I'm Nicole's sister."

"Oh," Kaitlyn said automatically, as if that explained everything. A second later, *then* it hit her. "**OHHH...** That Nicole."

Danny was still confused. "I don't get it."

Natalie turned to her friend. "John used to date my sister Nicole. We met just one time, briefly. But I didn't want him to recognize me so I asked you guys to call me Karen."

"Why? What's the big deal?" Danny asked.

Already I was half-recoiling from Natalie. I felt... dirty... somehow. The one time I'd met Natalie had been when Nicole asked me to pay for her mother's experimental surgery. She'd only been 17 at the time and my girlfriend Nicole had expressly told me to back off. My mind automatically went into that mode and I felt quite guilty for having just boned Nicole's little sister.

"That's the big deal," Natalie pointed at me shrinking away from her. "He wouldn't have touched me last night if he'd known."

"Nicole is going to FLIP when she finds out," I said with honest worry in my eyes.

"Yeah, she probably will," the young brunette nodded. "But it was MY choice. And I don't regret it."

Natalie's statement didn't do much to reassure me Nicole wouldn't be mad at ME, though. "What are you doing here?" I asked with mild trepidation.

"I told you, it's just a little vacation with friends. I never expected to run into you last night."

I was starting to get over my mild shock. "Wow..." The coincidence seemed amazing, but then I suppose you always find the world is smaller than you think. "You've grown up," I said while trying not to ogle her and remember what she looked like naked.

"And you're still much cuter in person," she gave me a dazzling smile.

I realized then that the other two in the room were staring at the two of us rather intently. Turning to Kaitlyn, I asked, "Can you guys give us a minute?"

"Sure," Kaitlyn pulled her bathrobe tighter and cinched the belt. Then she stood and shooed Danny out the door before closing it.

"So... Natalie... how's your mom?" I started, pulling the sheets around my waist to hide my nakedness.

She frowned at me doing that, but sighed and shrugged. "She's doing well. Her cancer is in remission and shows no signs of coming back."

"That's good to hear." There was a long pause before I got up the gumption to ask my next question. I still felt some guilt over what had happened. "And... how's Nicole?"

"She's good, she's good." Natalie glanced away and fidgeted for a second, seemingly debating whether or not to go into further detail. "She's engaged, actually."

"Really?"

Natalie smirked. "Yeah. He's an urologist. The guy looks at penises all day instead of gorgeous naked women, like you."

I blushed. "Good for her."

"Yeah..." Natalie sighed and reclined back onto one elbow. "She used to talk about you all the time, what you could have been together. But not anymore. She thinks everything worked out for the best."

"That's good. I'm happy she's moving on."

We went into an awkward silence, unsure of how to proceed. If she had just been 'Karen', just another pretty girl, I would have been able to act with confidence and certainty of what I wanted to do next. She would have been just a fun stranger, to be seen once and never worried about again.

But Natalie, she was someone loosely connected to my past. I couldn't just act without consequence anymore. Fishing for something to say, I finally just asked, "How about you? Anything I can do for you?"

"No," she laughed. "You've already done enough for my family, for all three of us."

"All three?" What had I done for Natalie? I'd only met her the one time before.

Natalie blushed and started playing with her hair. "You never knew this, but I had SUCH a crush on you way back when."

"Really?"

She nodded. "You were very cute, rich, and you were making my sister really happy. I was sooo jealous of her. You kept taking her off on those exotic vacations and living the lifestyle of the rich and famous. A couple of times I asked her if you two would bring me along, but she flat out refused. I used to lay in bed dreaming of what it would be like to be your girlfriend."

"I don't know. It didn't turn out so well with me and her."

"Wasn't really your fault."

"I DID cheat on her."

"Nah, that's not even what really bothered her. She talked about you a lot: great guy caught up in an extraordinary situation. She thought you actually handled things pretty well. But she just realized she didn't want to be a part of the media circus and your over-the-top lifestyle."

Natalie lay on her side and propped her head on one hand, relaxing more now that she was able to talk it out. "So don't worry about her. She's doing great now, living her quiet life with the nice house in the suburbs and her fiancé is a sweet guy."

I sighed and felt some of my lingering guilt over Nicole wash away. "I'm happy for her."

"Yeah, me too."

I looked more sharply at Natalie. "And what about you? You KNEW who I was last night."

"Yep."

"And you still... well... came upstairs with us?"

Natalie grinned, her hazel eyes sparkling. She started rubbing her fingers along the inseam of her robe, pulling the fabric away slowly while revealing just the beginning swells of her breast. "I told you, I had the biggest crush on you... When you didn't recognize me immediately, I thought it was a great opportunity to find out what it might have been like."

"You might have just told me who you were."

Natalie frowned at me. "I saw how you reacted when you found out who I was just now."

"Sorry, residual guilt for... well... having sex with my ex-girlfriend's little sister. We both know Nicole's not going to be happy about it."

Nicole got a sharp look in her eyes. "She's my sister, not my mom. I'm a big girl able to make my own choices."

"That wouldn't stop her from getting upset with ME if she knew."

"I suppose," Natalie exhaled and then rolled onto her back, staring at the ceiling. "Well... I will admit... you satisfied my expectations."

My ego puffed a bit, "Glad to hear that."

She rolled her head to me, her eyes hot with fresh lust. "So now that you know who I am, does that mean we can't do it anymore?" Natalie pulled her bathrobe aside again, revealing a dark nipple and kept pulling it open down to her crotch.

"Well," I gulped.

"I mean, it's not like you haven't already had sex with me before. But I really want to know what it's like, for you to make love to Natalie and not to Karen."

"Natalie..." I started. It probably wasn't a good idea. "Your sister might forgive me for sleeping with 'Karen'. But knowing full well who you are..."

"It's not her decision. It's mine, remember? Please?"

It wasn't like I hadn't already slept with her. And more to the point, Nicole wasn't my girlfriend anymore. The 20-year-old brunette had already turned to all fours and started crawling towards me. The bathrobe hung open so that I could see her perky breasts hanging down and swaying gently with her movements. And I had to admit, now that I knew who she was, the illicit notion of boinking Nicole's little sister had a naughty appeal to it.

Natalie seemed to read the acquiescence in my eyes, and as she got to me she reached down and tugged the sheet away from my legs. My half-hard cock became exposed to the air and she wrapped her dainty fingers around it as she leaned in and pressed her lips to mine.

I was kissing Natalie. I was kissing Nicole's little sister. The last time I'd seen her she'd been a very cute 17-year-old. Now she was still young and cute, but with stronger cheekbones and a more womanly face and body. And she was kissing me with nearly three years of built-up passion.

Natalie shrugged the bathrobe off her shoulders, and then I helped her pull it off her arms and then toss it to the side. She then moaned into my mouth as my hands reached up and began to caress her spine, my fingertips trailing lower until I was able to palm both her firm asscheeks in my hands.

She started kissing me harder as I tugged her crotch over my cock. I groaned as I felt my rod end up trapped between her labia and Natalie start gliding herself along it, smoothly lubricated with her own arousal.

There were no sounds but the hot panting and gasps of breath as we practically devoured each other's face, and despite my desire to get buried inside her tight pussy, Natalie seemed more than happy to continue grinding her crotch against my prick.

Her breathing sped up and her hips began to spasm randomly. But just when I thought she was going to blow, Natalie shifted her hips and reached down to grasp my dick. Elevating it quickly, she spread her legs and then impaled herself on my shaft, screaming in ecstasy as she sank down on my cock. Her orgasm was brief, but powerful, and for a long while after it passed she simply remained sitting on my lap, my cock fully embedded inside her while she leaned her forehead against my shoulder and panted for breath.

When she finally lifted her head to look at me, there were little tears in her eyes and she smiled weakly. "That was SUCH a good cum," she whispered. And then she pulled my head to hers in another fierce kiss.

After another few minutes of tongue wars and little internal squeezes against my cock inside of her, Natalie pulled away and started to lift herself off me. She moved up just a few inches and then sank back down before repeating the lift, pumping her body slowly along my shaft.

"Fuck me, John. Fuck me, please."

I started rolling my hips to meet her thrusts, and with my hands still on her tight ass I guided her movements as we picked up speed.

"Fuck me, John. Fuck me, John."

"I'm fucking you, Natalie. I'm fucking you," I groaned, only half-believing it was true. No matter what else, I would always know in the back of my head that this was Nicole's baby sister.

Natalie's face scrunched up as she began to feel the overwhelming sensation of another orgasm building inside of her. She was gasping again as she rode me athletically, driving herself with her legs on every stroke.

"Will... you... cum... in me?" she pleaded while pumping herself up and down.

"I can't," I moaned.

She rode me harder for a few more strokes, frowning but shutting her eyes against the pleasure still increasing.

"Then... cum in my mouth again. I want to taste you all day."

"Soon..." I breathed. I was close...

... but not too close. I managed to hold out until Natalie clutched my shoulders and started quaking, her legs still driving her body as she rode me through her orgasm and dumped another load of honey into my lap. I had to bite down on my lower lip to keep from spurting in the middle of it, and twice I shifted my hands beneath her ass in case I needed to lift her body away at the last second.

But I held on, and just when Natalie opened her eyes again and looked into my face with a serene gaze of intense satisfaction, I grunted. "I'm gonna cum."

Natalie just smiled and rode me even harder.

"Natalie!" I pleaded, but for a few more strokes she just seemed intent on getting me off inside her for the sheer pleasure of it.

But when I started tugging on the bottom of her ass, she nodded in understanding and dismounted me, quickly sliding over so that she could duck her head and wrap her lips around my glistening wet cock.

She only had to suck twice before I blew, and I heard the sounds of her gulping as she began to swallow down the spunk I was feeding her. Her hand started milking the rest out of me, and this time with a slightly reduced load, Natalie was able to drink all of me down.

***

When we emerged, Natalie was wearing her skimpy dress from the previous night and the bathrobe on top of that. I was in more casual clothes.

Room service had brought us a brunch buffet, and pretty much everyone was eating in the main room as we came out.

"Natalie!" Denise quickly came over and hugged her friend. She, too, was wearing her clubbing dress with a bathrobe. "Have a good time?"

The pretty brunette turned and looked at me with mixed happiness and sadness. "Yeah. I kinda don't want to leave."

"I KNOW," Denise looked around the suite. "Isn't this place amazing?" The two girls then started chatting animatedly as they moved over to a couch.

Meanwhile, Taylor came up and slung her arm around me. We smiled at each other, communicating everything without words. I also caught the attention of Cassandra, who just smiled and nodded to me.

Off to my left, I saw that Jeff was still sandwiched between Mia and Rebecca, who were taking turns feeding him grapes. I chuckled at that and then saw Kaitlyn just casually talking to Charlotte, seemingly unmindful of her boyfriend for now.

And right by my side, I caught Taylor winking at Danny, who was trying to look invisible while still staring unabashedly at my wife. And a sudden thought came to me. "Hey Natalie."

"Hmm?" Natalie broke off their conversation and turned to me.

"When do you leave?"

Natalie looked at Denise for a second and then seemed to think back over what day it was today. "Uh, tomorrow morning."

"Well I was just thinking," I began and pointedly looked at Natalie, Denise, and then Danny. "Would you three like to stay with us today?"

I caught Denise's quick glance at Danny before she locked onto Taylor. Natalie similarly started to smile.

"We don't have any major plans," I waved. "We'll cruise around the town, maybe a show later in the evening, or maybe just decide what to do as we go along. But we seem to all be enjoying each other's company and..."

Natalie wasn't looking at me anymore. She'd grabbed both of Denise's hands and looked at her insistently. From the eagerness in Natalie's eyes, I think she would have stayed with us even if her friends didn't come along for support. But to Natalie's relief, Denise got a nod from Danny and nodded in agreement.

"Great!" Natalie beamed. "Uh, we WILL need to check in with our friends and change."

"No problem," I waved. "What do you say we meet back here..." I checked my watch. "...at three?"

Our young new friends quickly looked at each other and nodded. The day was going to be a fun adventure.

***

It was actually closer to 3:30pm when the trio returned. Natalie apologized for being late, explaining that their friends were grilling them about where they'd been all night. And then when they planned to spend another full day with us, the questioning had only gotten more intense.