Obsessed with Miss Best of Breasts

"Thank you, thank you," she panted, then slid off, to rest beside me.

I pulled the sheet up around us, and we fell asleep.

***

Much like my night with Vanessa, sleep was a relative thing. We would wake up, shift positions, decide to fuck, then sleep again, repeating the cycle over and over. The only real difference was that, where Vanessa left me alone, Kaitlyn, stayed. We had a shower together, getting clean before getting dirty in there too. Then we both dressed, and went to have breakfast together.

We were sitting, eating quietly and talking back and forth, when Dannielle walked up.

"Well, well," she smiled at me, before sneering at Kaitlyn. "Look who's wearing the same clothes as last night? I don't have to guess what you two were doing, all night, do I?"

"Nope," Kaitlyn smiled. "We were having sex. Fucking. Doing the nasty. Getting it on. The horizontal mambo. Bumping uglies, although his cock is really quite beautiful; so long and thick."

"Thank you, Katy," I smiled. "Your pussy is quite lovely, as well. Nice and juicy, and very snug."

"If you're done with making me sick?" Dannielle snarled, aiming her disdain at Kaitlyn, before smiling at me. "I was hoping we might get together tonight?"

"Possibly," I replied. "I'll keep you in mind."

"Thank you, Cole," Dannielle breathed, bending to peck my cheek, while making sure I got a good look at her rack. She gave Kaitlyn a parting glare, then wiggled away.

"Persistent, isn't she?" Katy giggled.

"Yes. Gives a decent blowjob, but there's something about her that makes me leery of spending a whole night with her."

"Well, if I had a dick, I wouldn't," she smiled. "Come by my room? I want to change."

"Sure," I smiled back, and we walked out. Katy's room was on the ground floor, not too far away, and we were there in seconds.

Once inside, she wasted no time getting naked again, then made sure I was equally bare. Within seconds, we were going at it. I was on top, drilling her deep, while she hung on tight.

"Oh! I'm terribly sorry!" I heard, from the doorway.

This session had spontaneously combusted, and we hadn't put the 'do not disturb' sign out. As a result, the maid was standing in the open doorway, doorknob in hand, frozen in place. Her eyes were locked on us as we fucked furiously.

"Come... In! Close... the door!" Katy gasped. "Please. Watch!"

The maid paused, then stepped in, and locked the door behind her. She stood, a little uneasy, but clearly turned on.

"I love being watched," Katy hissed in my ear. "It gets me so hot!"

So, we did it, with an audience of one slightly older, but still attractive, woman. Her uniform tunic appeared to be well packed up top. I think her name tag said 'Maria', although from this range, and with my eyeballs bouncing as I fucked Katy hard, it was hard to say.

Katy was screaming, having one orgasm after another, after another. My attention was on her, when a sound made me look up.

The maid had unzipped her top, and her big tits were hanging out of her bra, while she jammed a hand under her stretchy uniform pants. She was enjoying herself greatly, and grunting through an orgasm of her own. It was all too exciting for me.

"F-U-U-U-U-U-C-C-C-K!" I roared, pulling out and kneeling over Katy's bountiful chest. I pumped my shaft a few times, and let loose a torrent of cum, streaking her boobs with white. Three or four strong jets leapt out, before the pressure lessened, and I shook the last drops on her nipples.

The maid groaned again, and shook, bracing herself against the wall, then the room fell silent. Only the tortured breathing of three satisfied people could be heard.

Maria was the first to move, gathering her balance, and tucking herself back into her bra, before zipping up.

"Thank you. I'll come back to clean, later," she smiled, and wobbled out the door.

"Is there some kind of story behind that?" I asked Kaitlyn, watching her play with her cum soaked tits.

"Um, yeah," she giggled. "My Mom caught me and my boyfriend once, not long after I turned eighteen. We were going at it fast and furious, and she opened the door suddenly, just before we were both about to cum. He didn't even slow down, just kept pounding me, while she stood there, watching him defile her little girl. It was soooooo hot! I had my biggest orgasm ever, right there, in front of my Mother. Ever since then, being watched, especially by an older woman, just sets me off like a firecracker! I know it's kinky, and a bit sick, but I feel like it's my Mom watching, all over again. And to have her get herself off, while watching? Oh, my god! I thought I was going to pass out! So... Fucking... Hot!" She looked at her gooey chest. "I need another shower now. Meet you on the beach later?"

"I'll be around somewhere," I told her. "After all, it's an island. Where can I go?"

***

As it turns out, there were more places to go than I thought, and not all of them were actually on the island. Every day, it seemed I discovered more fun things to do in this isolated paradise.

Yes, many of those fun things to 'do' were other contestants. My dick was having a great time, getting to explore so many beautiful women, and I was losing count of how many I had been with. The girls seemed to view daytime quickies as a marketing tool, much as they give out samples in a grocery store.

"If you like that," one girl purred, pausing mid-blowjob to make her case, "then you'll love what I can do to you for an entire night."

Before I knew it, it was swimsuit judging day. In actuality, the water is the last place these competition bikinis would be used. Covered with sequins and custom made for each body, they were obscenely expensive, but they did look good.

Tonight, the girls would be competing for double points. With each lady appearing on stage ten times, before eight judges, the maximum score for the evening gown competition was 800 points. Tonight, they were battling for 1600, and in the finale... the all nude extravaganza... that would be 2400.

It was a clear message; looking good in a sexy, long dress was important, but not as important as looking good in a little bikini. That too fell short of the importance of looking good naked.

Of course, all the judges had seen all the girls naked many times, since clothing appeared to have been deemed optional pretty much everywhere, but the pay-per-view customers hadn't had that benefit yet. The finale, and the guarantee of seeing one hundred naked women, all with really nice tits, is what had driven the financial success of the event.

So, I sat, pen in hand, as the groups of scantily clad women were paraded by me. An additional twist for this portion was the addition of mandatory poses, intended to show the viewers and judges the girls' bodies from all angles. I saw more and more faces I knew, and all had an extra smile for me. Vanessa, wearing a silver and black suit, looked like a Raiders cheerleader, with her huge boobs nearly spilling out of her top. Kaitlyn had on a blue and gold number, which went well with her hair and eyes, and I gave her several '10's, not because she slept with me, but because she was the prettiest girl in her group each time.

With the last group finally done, the ballots were collected. It occurred to me that, as much fun as I was having with these women, this was a serious business. Winning a sub-category... say, Best Natural Breasts, Amateur, under 5 foot 5 inches, B/C cup... carried a decent payday of five figures. Winning a category, was worth six. Classes went up from there, until you were left with only two women, as the best Natural, and best Enhanced. Each of those two took home one million, and the overall winner got a bonus of one more. For some, it was life changing money. For others, a nice bonus, and for the rest, a paid vacation where they got laid a few times, or a few dozen times, on an island resort few knew existed.

After the judging, I walked into the dining room, and sat at my table, waiting for the stampede of bikini clad ladies to enter. They had all been given cover-ups to wear, but most were merely carrying them, proudly displaying their bodies in their glittering swimsuits.

My table began to fill up. Louisa, Lynda, Barb and Annette were all seated on either side of me, looking decidedly organized. The rest of the table was made up of women I knew by sight and contestant number, but not by name. Even my stalker Dannielle was elsewhere tonight.

"I'm not sure if it's the air conditioning, or the company," Lynda, the petite blonde stripper with the massive chest giggled, "but my nipples are ready to cut glass, over here!"

"Mine too," Annette sighed, looking at me with her doe eyes. "I'm pretty sure it's the company."

The flirting and innuendo continued throughout dinner. Louisa leaned closer, and lowered her voice.

"A bunch of us are going out on a sailboat tomorrow," she smiled, silently reminding me that I hadn't actually had her yet. "I was wondering if you'd like to come with us?"

"Is that an invitation to sail with you, or to... Cum... with you?" I grinned.

"Both, of course, you silly man. The boat has a crew of two, so all we have to do is sit back, and enjoy the ride," she purred, rubbing my crotch with her hand. "It's time your dick met my pussy. Please say you'll join us?"

"Aye, aye, Captain!" I smiled.

"Good. Just to be sure you don't get lost on the way to the boat, Lynda and Barb are going to stay with you, tonight. Purely for security, you understand," she giggled. Lynda's hand replaced hers on my dick. I'd already had a very quick piece of Lynda on the beach, but it was something I'd love to experience again. A whole night with her, and the lovely Barb, was very appealing.

When dinner reached its conclusion, the crowd began to disperse. Here and there, a judge would leave with a woman, or two, in tow. Barb looked at me, and smiled.

"I hear the judges got suites? How big are those beds, anyway?" she asked.

"Big enough for, those, and these?" Lynda giggled, patting Barb's boobs, then her own enormous pair.

"I think so. We might have to cuddle pretty close, though," I suggested.

"Mmmmm. Cuddling close sounds like fun," Lynda smiled. "I'm done with dinner, and I'm hungry. Let's go get naked."

"You always want to get naked," Barb replied.

"Occupational hazard," Lynda nodded. "Force of habit."

"I think Lynda is right," I joined in. "Let's go get naked!" I stood up, and hooked arms with my two escorts. Louisa and Annette both pressed close, and kissed me.

"I'll be seeing you on the boat," Annette winked. "I'm looking forward to more of that dick!"

A few minutes later, Barb, Lynda and myself were just inside my door. Lynda wasted no time, and quickly unclipped her suit, letting it fall to the floor. Barb did the same, and both girls wandered naked around the room.

"I could get used to this," Barb nodded.

I had stripped my clothes off by now. Getting constantly caressed at dinner had started my cock going. Now, with two buxom beauties nude before my eyes, I was fully hard. Lynda turned, and smiled.

"I could get used to THAT, too," she giggled, moving quickly across the room, and pushing me over onto my back on the bed. For such a little thing, she was surprisingly strong, and once I was down, she pounced on me. Her mouth was on my cock in a second.

Barb just shook her head, and snuggled beside me, pressing her DDD's against my side, and her lips to mine. Her kiss was warm, soft and wonderful. In my imagination, I pictured her doing this, with her girlfriend.

"Mmmmm, thank you," I said softly. "You're sure that your girlfriend is alright with this, right? I don't want to get in the middle of a relationship."

"I appreciate that," she smiled, nodding her head thankfully. "Yes, she's good with it. We had a long talk about what was likely going to happen here, and we've both agreed that the potential benefit was worth the temporary danger. She knows how I feel about her, and that anything that happens on this island doesn't effect us at home."

"That's good," I smiled.

"Besides, you could just as easily ask her yourself," Barb giggled. "She's sucking your cock, right now!"

Huh? I looked down at Lynda's bobbing head. She paused, tilted to the side, and winked at me.

"I see," I groaned. "Doubling your chances to win."

"Well, why not? We work together, too. I serve the drinks, while she takes her clothes off and gets tips stuffed in her g-string. I told you I asked a friend about her implants? That's her," she explained.

That was true. She had told me that, on the beach. I just never thought she was talking about the woman sitting next to her, at the time. They were very good at keeping their feelings a secret.

"Okay, Barbie, honey," Lynda said happily, lifting her mouth off my dick. "I think he's ready. Do you need my tongue, or are you good?"

"I'm juicy, and ready to ride," Barb smiled, rolling into position. Lynda pointed my penis at her pussy, and Barb lowered herself onto it. "Mmmmm, you were right. It is quite nice, and thick. Thank you, darling."

Barb turned her head, and kissed Lynda, using her tongue quite visibly.

"Alright," Lynda grinned. "Now, whatever shall I do while you're fucking him? I know! I'll sit on his face, and suck your nipples!"

I wasn't stupid enough to argue, and Lynda swung her leg over me, facing her brunette lover. Her pussy was smooth, and her labia pouted open, dangling over my face. She was quite damp, and as she settled lower, I could smell her arousal. I reached up, and used the tip of my tongue to tickle her clit.

I heard her moan, and giggle, but no words. Perhaps she was already latched onto Barb's nipple, making further comments difficult. It was something I would like to have seen, but her pussy was now filling my field of view. Perhaps I could get them to put on a private performance for me later, but for now, I had a job to do, and Barb's pussy was sliding up and down my shaft. As long as that was happening, it was hard to complain.

Exactly how long we were positioned like this, I have no earthly idea. It was long enough that Barb's pussy became a swamp, dripping all over my balls, and Lynda neared that level of wetness as well. She was doing little figure eights with her lithe, dancer's hips, rubbing her juiciness on my chin, and the bridge of my nose. My tongue kept swirling around her clit, and I heard her moans get deeper.

The answer to the age-old question, about who came first? It wasn't the chicken, or the egg at all... It was Barbara. Her cunt clutched my cock tight, and I heard her groan, just seconds before Lynda gushed on my face, which was just seconds before I flooded Barb's vagina with my semen.

"Ohhhhhhhhhhhhhhh," we all sighed, in near unison, which made us all laugh as well.

"Stop!" Barb frowned, trying to regain control. "If I laugh, I'm gonna squeeze cum out all over the place!"

"Worry not, my pet," Lynda smiled. "Bring that pussy over here. I'll take care of it." She rolled off me, to the side, and laid on her back. Her huge tits pointed up like torpedoes, but it looked good on her.

Barb lifted off me, and spun around, planting her gooey, oozing muff right on her blonde lover's face. She then dipped her own head between Lynda's thighs, and the show began.

Like most guys, the prospect of two women getting it on before me was a recurring fantasy. I had seen it, several times, on video, and that was quite titillating, but this live performance left all that in the dust. It was made even more interesting by the fact that Lynda was busy sucking mycum out of Barb's pussy, not just her usual delicious juices. That made me more participant than spectator, in my book.

I laid there, watching the two ladies munch on each other, from close range. I must admit, seeing Lynda's tongue dipping into Barb's cum filled pussy was very exciting. Strings of my cum were being drawn out, to be slurped into Lynda's mouth. She was moaning softly, and making yummy noises, which I chose to credit to my contribution.

Both of them were clearly enjoying each other. I wondered how many nights in their year together had found them happily gorging on their partner's succulent pussy. I could imagine the two of them, working together, flirting with the mostly male patrons of the strip club, yet knowing that the evening would end in each-other's arms; Barb watching her luscious Lynda gyrate seductively on the stage, shedding clothing, and shaking her huge tits at the front row, encouraging maximum tips. Lynda would be observing Barb as well, watching her sexy ass wiggle in her tiny shorts around the bar, as she served drinks and hung her own spectacular pair in the faces of her customers.

Their moans were becoming synchronized, as Lynda moved beyond merely cleaning Barb's pussy, bringing her closer to another orgasm. When it happened, it was sudden, and both of them shuddered through the pleasure.

It had been a long day. The ladies were now relaxed, having burned off the stress of the judging by making each other cum. I was content to have them snuggling in bed with me, so we all curled up, and went to sleep.

***

Twice during the night, I was awakened by a hand caressing my erection.

The first to do so was Lynda, who rolled on her back and pulled me atop her, massive, cushioning chest. Her legs spread wide, and her small hand guided my hard shaft into her drooling vagina.

"Shhhhhhh," she smiled, as I pushed inside her fully. "Nice and slow, and gentle. Don't wake Barb up. This is just for us, okay?"

I was too sleepy to argue. Besides, my cock was already buried balls-deep in her very juicy snatch, and those huge tits were pressing their fullness against my chest. I nodded, and started to slowly ream her pussy.

This was very strange. It had never happened to me, but it seemed that if a woman was urging you to fuck her, alongside her sleeping significant other, that significant other would usually be an inattentive husband. Not an equally beautiful... and equally willing to participate... woman.

Still, this situation had been strange since I opened the letter at home, that offered me the chance to judge this extravaganza of boobs and sex.

Our difference in size was making this a little difficult, as I'm over six feet, and Lynda was a petite thing, barely five feet. I didn't want to be jamming my shoulder in her face, but it was happening on occasion.

"Oh, yes, that's nice," she whispered, her face against my chest. "Just like that. So deep. I love it deep like that. A little harder. Oh, fuck! Yeah! Oh, yeah."

She buried her face, muffling her sounds, and shook under me. Her little body clutched at my back and hips, while her pussy spasmed, grabbing my dick tighter.

A hand on my butt made me look over at Barb, who was facing us, head on her pillow, eyes wide open. She smiled, and held a finger to her lips, then went back to gently massaging her clit while she watched us.

"Oh, my god, that was good," Lynda moaned softly. "Don't stop. Please, don't stop. I need more."

So, I kept going. Lynda was blocked from seeing Barb by my body, so I just watched Barb get herself off, while my cock probed Lynda's depths repeatedly. It was fun. Barb's face was so expressive, as she came on her fingers in an equally gentle and silent fashion. I felt Lynda shudder under me on at least three more occasions, before I knew I was going to cum myself. Part of me wanted to let Barb suck me dry, but that would spoil the secret for Lynda.

"Lynda?" I whispered.

"Let me swallow," she smiled, sensing my impending climax.

I pulled out, and laid on my side. Lynda quickly shifted position, and locked her lips around the head of my cock, stroking the slippery shaft with her hand, until I spurted. While she sucked and gulped down my load, Barb silently caressed me, and whispered in my ear.