Obsessed with Miss Best of Breasts

And the viewer total climbed higher still, as a few of the girls had done promo spots earlier in the day, that had gone out on the internet. When a naked, statuesque blonde, with big tits, shakes those puppies at you and says you can see another hundred and ninety-eight more, just like hers, well... ten bucks just flies out of your pocket. It's a law of nature.

At last, the broadcast started, and I took my seat, awaiting the first group of twenty breasts... I mean, um, ten lovely ladies. Ah, there they are now.

You'd think after two weeks here, watching these women bounce, wiggle and jiggle around the island, I might have become desensitized to the effects of being around them. If that wasn't enough, then there was the twenty or so I'd had sex with. I should have been numb, and oblivious to their charms.

Not hardly.

As the girls came out, balancing on their high heels, my eyes were inexorably drawn to their contest qualifications, which were dancing along in front of them. They came out in a jiggling, wobbling, extremely arousing line, and hit their marks, stopping in front us, to be judged. They each wore a smile, and nothing else, of course, except their numbers, which gave them a sporty appearance.

On cue, they turned, showing us their delicious posteriors, then again into profile, so we could see the magnificent projection of their breasts. Every nipple was hard, and erect. I wondered if any women had ever been naked, live, in front of such a large simultaneous audience before. Not even Janet Jackson's infamous wardrobe malfunction could compete with this, and slow motion wasn't going to be required to see this skin.

Group A1 stepped aside, and opened the stage for B1. In this group was Annette, who made direct eye contact with me, and gave her boobs an extra little shake, smiling happily. Similar non-verbal greetings were exchanged with all the women I had, ahem, had. In most cases, they were deserving of the top votes for the group, and I gave them those ten points.

The long, naked parade continued, and continued, and continued. My dick was hard throughout most of it, which made me wonder a little about how the girls were feeling about the process. I had to assume they were all dripping wet, and excited beyond reason. As the long day went on, I saw proof of that arousal, as several of the ladies had obvious streaks of wetness on their inner thighs.

During the second break, I went for a little walk to stretch my legs, and wound up in the back-stage area. There I found confirmation from my conclusion about the contestants and their feelings.

It was a virtual orgy back there. Women were masturbating furiously in one area, and a few had their faces planted between a fellow contestant's thighs. Crew members were taking advantage of the horny, needy women, fucking them here and there. My cock was throbbing before I saw the spectacle. Now it was like stone.

I made eye contact with a buxom blonde, who was spearing her bald cunt with three fingers, while yanking on her nipples with the other hand. She was seated on a convenient piece of stage equipment, with legs lifted and splayed wide. She withdrew her fingers, dripping with juices, and gestured me over to her.

"Hi, I'm Charlotte. Fuck me, please?" she begged.

I didn't need to be asked twice. As soon as my cock hit the air, I plugged it into her gaping hole.

"Oh, fuck, yeah, that's better," she smiled, dropping her hands to my ass. "My fingers just weren't getting it done. Fuck my pussy nice and deep, please. I need to cum, or I'll lose my mind!"

I was nearly ready to lose mine, too, so I drilled into her juicy depths in a steady rhythm of hard strokes, crashing against her body and setting those delectable tits of hers wobbling crazily. I took note of the number on her thigh, and recalled seeing her several times already. If I was right, I think she was doing pretty well in the contest.

"Oh, yeah, fuck me!" she gasped, clearly feeling it. "Fuck me! Just like that, honey! You're gonna make me cum! Oh yeah! More! More! Mmmore! Oh y-yeah! I'm... I'm... Cum... Oh my GOD! YES! YES! FUCK YESSSS!"

Charlotte's body shook in my grasp, as she came. I was happy I could help her, but I had needs of my own to look after, too. I fucked her harder.

A buzzer sounded in the background.

"Hurry! I'm due onstage!" she giggled. "Fuck me! Cum inside me!"

"I'm a judge," I told her. "They'll wait until I get back to my table. Besides, I'm close."

I had hardly said the words before I felt the tingle. I found another gear, and thrashed her receptive cunt even harder. With one last thrust, I buried my shaft balls deep, and exploded inside her.

"Oh, thank you," she breathed in my ear. "I really needed that. Being naked all day... It really turned my crank."

"My pleasure, number 84," I winked, stuffing my wilting dick back into my pants. "See you onstage."

I quickly took my place out front, at the judges table, and the broadcast resumed, only a few seconds late. A new group of ten beauties came out, walking with elegant grace on their high heels. Charlotte / #84 was smiling, showing no effects of have just been ploughed furiously. She glided to a stop, only slightly unstable on her tall heels.

This was a tough group. Usually, it was pretty simple. I'd pick the busty body that excited me most, then the one that held the least appeal. The difficulty would be in the middle of the ranking. This group were all so pretty, and evenly matched in height and cup size. It was hard to pick a favourite. In the end, I gave Charlotte my top vote, partly because her nipples were standing tallest, and partly because my semen was trickling down her leg.

***

At last, the final group had been judged, and we were done. It was up to someone else to finish crunching the numbers, and determine who actually won what. I could relax.

Or at least, so I thought. There was one more job to do.

There was a tie, and we had to break it. The process was pretty simple; the two girls involved would come out, and free pose, before the judges. There was over ten thousand dollars on the line, so for the ladies, it was serious business.

Out came the two lovely ladies. They were both in the Enhanced class, and sported beautifully round, full breasts, that rode high on their chests and hovered as a unit while they walked. They both stopped, side by side, and struck the basic modelling pose, one leg extended, and hands on hips.

I could see why they had ended up tied in the contest. Same height, similar build, both brunettes, both pretty... and of course, both the owners of firm, honeydew-sized melons. I had met them both, but only had sex with August, as Brenda's charms had escaped me.

Free-posing began, with the girls trying to outdo each other in shaking their assets. Things began to get physical, as they each tried to block the other's moves. Elbows flew, and hip-checks were exchanged, until Brenda caught August flush with her hip, and sent her toppling off her heels.

To her credit, Brenda immediately paused, and knelt to check on her competition. August was okay, but surprised to find herself on the floor, and she accepted the offered assistance to get back on her feet. Brenda brushed her hand across August's supple ass, and the posing took a turn to the erotic.

The girls exchanged whispered words, and hugged each other, pressing their large breasts together, and caressing their opponent's body gently. They even kissed, and turned to face the judges, cuddled together, with a handful of each other's beautiful breasts. They had clearly given up trying to beat each other, and left it up to us.

It really was unfair to choose between the two, or rather four, as their breasts were supposed to be the deciding factor. They both had spectacular racks.

I looked at the other judges, and shrugged, getting a similar response from most of them. In the end, they both won, as we left the tie in place.

***

I woke up late. It was my last morning on the island, and there was no schedule to keep, other than my flight in the late afternoon. I was very relaxed.

Part of the reason for that relaxation was laying next to me. A shock of tousled red hair rested on the pillow beside mine. It was Kaitlyn, and she was snoring quietly.

She hadn't been the only woman to visit last night. What had started as an unofficial wrap party for some of the women I had become acquainted with, had quickly turned into something of an orgy.

Being the only penis in the room, I was passed around among the dozen or so ladies, providing the pleasure of penetration when tongues and fingers just weren't enough. The suite was full of writhing bodies, most of which would be leaving with considerably more cash than they arrived with.

What can I say? I have good taste, and most of my choices wound up winning, including Kaitlyn, who had won her category, and would have enough money now to pay for her law-school bills. She would soon become one of the best built lawyers on the East Coast.

For now, though, she was just the last one here. Everyone else had filtered out throughout the night, some to sleep, and some to pack for early departure. That just left us alone, and we had been active all during the evening and early morning, using each other up before we were forced apart. She stirred, and I looked at her, seeing an eye flutter open through the tangled strands.

"Hi, gorgeous," I smiled, reaching out to comb the errant hair away from her pretty blue eyes.

"Mmmmm. Morning," she moaned, stretching like a sexy kitten. "It is still morning, right?"

"Yeah, but just barely," I answered, checking my watch.

"I'd better go, or I'll miss my flight," she smiled, caressing my face softly. "Thanks for all the fun, the last two weeks."

She inched closer on her pillow, and kissed me, then slipped out of the bed. Gathering her clothes, she paused at the doorway to scribble something on a piece of paper.

"Thanks Cole. Come see me sometime, okay?"

A parting smile, and she was gone.

***

It didn't take me long to pack. I hadn't brought a lot of clothes, and there weren't a bunch of souvenirs to go home with, just some lifelong memories that future relationships would never understand.

There was one item I was happy to take with me. I assume, since Annette's name was at the top of the page, that she had started the list that was safely folded in my pocket. The list, of fifteen names and phone numbers; all women who volunteered their information in the hope that our paths might cross again. It was my prize, for two weeks in paradise.

I found myself on the dock, looking around one last time before boarding the seaplane for the short flight back to the mainland. My favourite hot pilot, Chrissy, had already tossed my bag aboard, and was waiting in her seat patiently for me to climb up and into the plane.

"Ready?" she asked, her eyes hidden behind her sunglasses. "Don't want to miss your connection."

"Yeah, I'm coming," I nodded, clambering up. "Just had a lot of fun here. Gonna miss it."

Chrissy smiled, and pushed the button to bring the engine to life. The prop began to spin, and we were pushed away from the dock, powering slowly out to sea. I found myself lost in thought, remembering the events since my arrival here, two weeks ago.

It occurred to me that we were not yet airborne, and I looked over at Chrissy.

"Are we flying, or just sailing?" I laughed.

"Neither," she smiled, taking off her sunglasses. She turned in her seat, and killed the engine. "Marla is a good friend of mine, and she told me that I shouldn't let you get away without giving you a try, myself. So..." she giggled, beginning to unbutton her blouse, "How about one for the road?"

I had never fucked a pilot before. I'd never fucked in a plane, either, nor had I fucked a pilot while floating in a plane.

I had a feeling all that was about to change, because Chrissy had her blouse off by now, and was kneeling in front of my seat, wrestling my belt open. Her large breasts shook in her sexy red bra as she struggled with my pants, but she would not be denied. I lifted my hips, and she yanked everything down.

"Well, I can see why Marla gave you such a glowing recommendation," she smiled, taking my semi-soft but still thick cock in hand. She stroked it, watching it harden and grow, while she tugged her bra down with the other hand, fully exposing her generous breasts and hard nipples. "Oh god, I just have to suck it. You don't mind, do you?"

I have a general policy in life; if a pretty woman offers to suck your cock, the answer is always 'yes'. I was about to explain that to her, but she had made the correct assumption, and already had her mouth full. Her blonde head bobbed slowly in my lap, and I caressed the golden locks softly, enjoying the delicious sensation on her lips and tongue, slathering my penis with saliva.

"Mmmmm. I rather like the service on this airline," I moaned.

"Oh, this is just the appetizer," she grinned, rising from her knees. She reached under her short skirt, and skinned off her tiny panties, then straddled me, hovering her vagina above my dick. With deliberate slowness, she lowered herself, sliding her slipper pussy down over my shaft, until she was fully impaled. Her blue eyes sparkled, as she put her arms around my neck. Her stiff nipples dug into my chest, pressed against me by the full volume of her breasts.

"There," she sighed. "Now, this is the full service. Marla was right. You are quite large, and long. You must have made so many women happy on the island."

No more so than made me so very happy, I thought, accepting the praise.

Chrissy rose and fell slowly, grinding her cunt over my cock with her supple hips. I captured one of her nipples with my teeth, and gently scraped the sensitive bud, eliciting a moan of pleasure from her. With her natural endowment, she could probably have done well in the pageant, as could Marla, but I suppose they had less need of extra money, already living in the idyllic resort.

So, the plane drifted, bobbing gently on the waves, while inside, we fucked with equal gentleness. Chrissy's pleasure began to build, and she picked up her pace, until I had to release my hold on her nipple. Her chest was simply bouncing too wildly to control, and I settled back to watch her big tits dance as she skewered herself desperately.

"Fuck! Your cock is so good!" she groaned, pounding her hips up and down furiously. "My little pussy likes it!

"At the risk of overstating the obvious," I laughed, enjoying both the show and the feeling of her snug crevice gripping my cock, "my dick likes it, too!"

"Well, don't enjoy it too much, okay?" she asked, tossing her head back. "I'm almost there! Oh fuck! Almost there! Gonna cum! Oh god, gonna cum! Gonna... AIEEEEEEEEEYEAH!"

No need to worry about privacy, way out here, hundreds of yards off the shore of the island. Chrissy could scream as loud as she wanted, and no one but the whales would hear her. Her body shook as the orgasm ripped through her, until she dropped her head on my shoulder, gasping for air.

"Oh... Boy, that was good," she sighed, resting in my embrace. Her breasts felt so wonderfully firm, squashed between us. I stroked her hair, and held her, until she recovered.

"Alright, I've had my fun, but we do have a schedule to keep. I assume you wish to cum?" she giggled, sitting back to make eye contact. "I'd like to avoid making a mess in the plane, but I'm happy to swallow, if that will help?"

"Certainly," I smiled. "I'd like to see those boobs bounce a little more. Please, continue, and I'll tell you when I'm close."

A little grin on her lips, she leaned back to arms-length, and started to ride my cock again, making sure to shake her tits at me. She made a show of it, but was clearly enjoying her own performance nearly as much as I was. Probably more, as her moans would confirm.

"Oh, fuck, your cock is gonna make me cum again!" she gasped, grinding her pussy firmly against the base of my shaft.

And your pussy is gonna make me squirt, I thought, but I can hold off until you have another orgasm. It would be rude to leave you hanging.

I gritted my teeth, and thought about ugly nuns playing baseball, while Chrissy rode me hard, bouncing her boobs in my face. When she came, she screamed again, and nearly fell off my lap, but I caught her.

"Anytime you're ready," I grunted, as the ugly nuns morphed into hot ones, took off their habits, and shook their huge tits in my imagination. It was a temporary delay.

Chrissy lifted off, and took her place, mouth open and willing to take my load. My hand instinctively did the rest, and within seconds, ropes of thick goo were landing with pinpoint accuracy inside the opening, splashing across her tongue and down her throat. Once I got things started, she leaned forward, clamped her lips around the head, and sucked the rest out of my balls, moaning softly.

"Mmmmm," she smiled, wiping her chin, and standing up as much as the plane would allow. She slipped her bra back into place, holstered her breasts, and eased her blouse back on over her shoulders. "Now, let's get you to the airport."

I nodded, which was about as eloquent as I could be at this point. A minute later, Chrissy had us airborne, and we looped past the island one last time, giving me a final look at the place that would forever be burned in my memory. We even buzzed Marla, out on her sailboat, and she waved at us as Chrissy rocked the wings.

I tucked everything back into my pants, and took the seat next to Chrissy for the duration of the flight, watching paradise get smaller, and the real world get bigger, as we went.

I said it before, and I'll say it again.

Best. Trip. Ever.

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This story was planned as a one-shot deal, but some of the characters might have a future.

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