Fantasy On Halloween Island

I awoke in a fog. Loose dirt clung to my face. I was drooling. Through the haze I could see a line of guys in "security" shirts blocking the way back to the island. Behind me was the ferry.

"Time to get up, man," grunted one of the oversized, testosterone filled oafs.

He pushed me towards the gate of the ferry. I frantically looked back over their shoulders to see if I could see a certain red head with the wonderful round hips and bouncy tits....or the thin blonde with the swimsuit model's body. I saw a pen in a clearing, there were naked women in it. I couldn't make out who, my eyes were still too unfocused. The gate closed, the ferry pulled away. I watched the island disappear in the distance.

{Six weeks earlier} Imagine my surprise when I got a call from my ex, Rebecca. It had been three years. She was trying to make small talk but she was still the same, I could tell when she was trying to get something out of me.

Finally, I just chuckled. "Okay, what is it you want, Rebecca?"

She sighed like she was caught. "Sorry, it's not easy bringing up this stuff, even if you are one of the few to understand it."

"Understand what?" I had an idea it was something kinky, though. That was one constant with her. The woman loved sex, especially submissive sex.

"Well, remember when you put me in a corn maze and made me have to please those guys?"

I laughed. "Yeah, kind of, rings a bell."

That had been just over four years ago, before we had broken up over....nothing really, at least to me. There was an age difference, she's just turned 38 and I'm now in my mid 50s. She's adventurous, to the point of going places and doing things far beyond her means. I was content to be together and enjoy each other, it wasn't enough for her. She met someone else more "suitable" and left, though she broke up with him soon after.

She's adventurous sexually as well. The corn maze thing was just one of the many things she and I did together. We were never exclusive, she had plenty of "friends with benefits" before, during and after our relationship. I knew there had been plenty of lucky recipients of her charms since we broke up, no doubt including some of her coworkers, friends and other fortunate guys. She's a sexual dynamo, she loves having cock in her mouth or pussy (and she's not averse to anal!). Unfortunately, I had not been one of the lucky ones since we broke up. Not that I didn't think about it.

Back to the call, she told me her oldest daughter, Parker, now 19, told her she heard about her mother's "adventures," which shouldn't have surprised anyone, she HAD been very sexually active before, during, and I suppose after we were together.

"That's not why I'm calling you though. Parker is.....how do I say this? Well, she's a bit of a slut now."

"What?" That was a shock, considering when we were together was 15. She was still just a kid then. I've seen her numerous times since, she's grown into a gorgeous young woman.

"Well, she's kind of a big slut," she laughed. "Kind of like me, sadly."

"Why sadly? There was absolutely nothing wrong with your sexuality. I loved every minute of it."

"Yeah, you were always good with it and honestly, as long as she knows what she's getting into I'm okay with it. But, that's the thing....."

"Here it comes," I thought.

"Parker is on some pretty....provocative websites. She found out about my corn maze thing on a chat thing on Redditt, I think. Anyway, her "research" led her to something.....big, sexually."

"What? Another corn maze thing?" I chuckled at the "big" thing as a typical man.

She laughed out loud, for real. "Ha, I wish it was something that simple."

She told me about a Halloween contest, the only information is online, by invitation. Parker had sent a request and some nudes (as payment) in order to read the details of the contest. The contest was bizarre and amazing. There was a billionaire, or perhaps a group of them, who own a private island off South Carolina. There were no names attached, of course. The contest was this. A woman could sign up for the contest. She had to submit nudes and answer a very detailed sexual questionnaire. Also, she had to write a detailed story about her sexiest adventure. It would all be evaluated by a "panel" for the contestant to be chosen for the adventure, which she still hadn't explained.

"So where does that put you...and Parker?" I asked with amazed interest.

"Well, being the wonderfully devious, smart and slutty person that she's become, she actually applied for it, and she used the story you wrote about my maze adventure as her submission for it."

"Wow. Glad to see someone getting the benefits of my writing," I joked. "But seriously, are you sure it's not a scam or something? I mean, it could be some pimply faced 18 year old dude who just wants nudes and stories to jerk off to."

"I know, that's what I said, too!" she said. "But, Parker looked into it. There was a subreddit about it from previous years....it gets pretty....hairy....but it looks real."

"You HAVE to tell me, what the hell is the adventure?"

She sighed and gathered her wits. "The contest is for $10,000 for any woman who makes it across the island before being....caught."

"Wow....wow wow wow. You mean caught like.....caught, sexually, right? Kind of like your other adventure?"

"Yes," she said exhaling sharply. "This is WAY more intense than that, though. We have to agree to all sorts of things, sign a bunch of waivers and agreements. But, the game is, they drop us off at one end of the island, which I think is a couple miles long. We might be nude or....restrained in some way. But if we make it before we are caught we each win 10k."

"Wait, WE?"

She sighed again. "Yes, Parker signed me up as well."

"What, why?"

"For one, there's NO way I'm letting her do that without someone with her. Second, she either has to be 21 or have an adult with her. Third, it sounds......kind of amazing, doesn't it?"

I recognized the lust in her voice. She was into the idea.

I had to know something. "Okay and wow about all this, but why me? Why tell me about it?"

"Safety, I trust you. But....I was also kind of hoping you'd.....you know....tag along."

"Tag along? Get chased, naked across an island by...god knows who? Not my thing," I joked.

"No, not as a contestant, as a .....guide/monitor thingy. It says in the rules that one person can "observe" but not participate."

Backing up here. Rebecca is a dream. She's got long red hair, curvy hips, beautiful firm and full tits and an ass from heaven. Parker is nothing like that, just a different kind of dream. She's got blonde hair, she's much taller than her mother. Her tits are small, pert and sexy, with amazingly hard nipples when erect (yes, I noticed, hard not to). She's got a lean, thin body like a swimmer. Everything on her is tight. They couldn't be more opposite but so damned sexy at the same time. If I could "monitor" either of them for any period of time, I was in.

"So we're taking a trip to South Carolina!" I kidded.

"Maybe," she warned. "We submitted our entry, it doesn't mean they'll accept it. I've heard all sorts of strippers, "B" actresses, famous athletes and such have applied and "run the course" before."

"Really?"

"Yes, and, it's rumored that some of the "hunters" are actually famous and rich people. Think about that, if I make it across I win the money, if I don't, I might be a sex slave for Brad Pitt or something!"

I laughed. "Or, you'll end up with some whack job like Ted Nugent or Howard Stern."

"Ew!" she sniffed.

"Wait....wait wait wait.....sex slave?"

"Uh, yeah. That's the penalty for not making it. If you get caught, you are the....let me read it here in the rules....."If caught you become the property of the hunter that catches you. You belong to him or her for the remainder of the weekend until the Monday ferry at 11am. This includes the rights for them to use you sexually in any way they choose, as often as they choose, when they choose. Violence is not allowed that is not agreed to by the hunters and the contestants."

"What the fuck. Are you kidding? A sex slave for a weekend to....god knows who?"

"That's the contest," she giggled.

"I can almost get it for you, you have quite the adventurous sexual appetite, but what happens if, god forbid, Parker gets caught?"

She sighed. "I know, I've thought about that since this started. I can't stop her, though. She told me she was doing it with or without me. It was her idea to start with. Now, I'm tortured with the idea of doing it....and not doing it. It works me the fuck up, I have to admit, yet I'm scared to death about it, too. She's much more fearless than me. She's like, "so? not like I haven't had sex before."

"Oh, and there's more in the rules...."hunters can sexually use their prey in front of whoever they wish. However, the use rule only applies to the hunter, not any voyeurs." So, they can watch us get used....that makes me.....gooey thinking about it."

"Hehe, ok, gross," I kidded. "When will you find out?"

"There are stages, apparently. First, our application has to be accepted. Stage two isn't revealed unless the entry "passes."

"What would cause an entry to pass, or fail for that matter?" I asked.

"Well, our looks definitely matter, which is why we had to send nudes. Then, there's the sex questionnaire Parker answered. She basically said she said "yes" to pretty much every question."

"Why?"

"She said, "mom, why would they take anyone NOT willing to do certain things?" I think she's right, they are looking for a certain "look" and a willingness."

A week later I got another call from Rebecca. "Guess what?! We're on to stage two!"

I heard the giddyness in her voice, for me there also was some dread or fear. I mean, still, did we know anything about any of this, really?

Her excitement continued, "we have a zoom call later this afternoon. The judges will talk to us and see if we pass this next step!"

"What's the next step?"

"I don't know!" she answered with excited frustration, "that's what the zoom call is for!"

"God, I know you are excited, but aren't you scared at all? What if these people are whackos or the whole thing is an internet scam?"

"From what Parker says, it's totally legitimate, there are many sites, not related to each other, that corraberate the story. But, if you want, why don't you come over before 4pm, you can sit it, not IN the zoom call, but you can watch, see for yourself."

"How are you uh....handling the anticipation, the excitement?" I asked, knowing her needs.

"Oh god, Parker made me SWEAR not to do anything with anyone until the contest is over!"

"What? Six weeks? That's an eternity for you! I don't remember you ever going a week without it without losing your mind," I joked.

"I know! God, all my FWB's are all on lockdown now. It's like we're all going through withdrawls. I can't LOOK at a guy's package now without wanting to jump him and the guys at work who enjoy my mouth frequently can't leave me alone about. I obviously can't tell them WHY I won't....we're all a bit edgy here," she giggled.

It was time for the call, I stood in their kitchen, out of sight of their pc while Parker and Rebecca took the video call. Per Parker's suggestion, they wore "classy" but sexy outfits. They both had sundresses which hightlighed their cleavages nicely.

"Good afternoon," came the low, husky voice on the other end. There was a "panel" of judges, all with hoods over their heads and black eye masks.

"Hi," Rebecca giggled nevously.

"Congratulations on passing stage one. This is stage two. This is for the purpose of checking the legitimacy of some of the items from stage one. Are you willing to answer questions, perform some tasks required to proove your worthiness?"

"Yes!" Parker said quickly. I kind of wished they'd asked what the tasks were beforehand.

"Good, good," said the man coolly. "Now, for starters, you must be Rebecca," he said, looking at her. "Now honestly, if you'd entered by yourself I don't think we'd have accepted you."

I saw the disappointment on her face.

"Not that you aren't a beautiful woman, it's just that we...tend to prefer younger women, no offense. However, since you entered as a duo, it piqued our interest. We've never...had that situation before, the mother/daughter entry."

I could hear the interest in his voice.

"I saw your pictures, Rebecca. Again, very beautiful woman, but, we've had many people send us phony pictures or ones from years ago. Can you verify these are recent?"

"Uh, yes. Parker took them last week."

"I mean proof," he smiled, his lip curled up to his mask.

"You want me to.....?"

"Strip, yes, if you please."

Rebecca hesitated, but on Parker's insistence she slid the sundress over her head, revealing her nakedness underneath. The man made her stand there while the other men put their faces in closer to their pc. We heard positive muttering.

"Turn around," the man urged. Rebecca obliged, showing them that magnificent ass of hers.

"Nice, very nice, you were true to your word. Admittedly, you are on the fence because of the age thing, but I think you may have gained a few points back," he smiled.

"Now you, young lady," he said, looking at Parker.

Her dress dropped to the floor and she was made to model her body for them in the same fashion.

"Yes, yes, the two of you together....definitely helps your entry. "Let's talk about the questionnaire."

I saw Rebecca gulp for air.

"It seems you two have very little restrictions, is this true?"

They both nodded nervously.

"I mean, some of this stuff is quite....intense. So you two are "no holes barred?" he asked nonchalantly as if asking basic demographic questions.

I saw Rebecca shoot Parker a nasty look but they both nodded to the affirmative.

"and the rest, including exhibition, public use, disciplining?"

I saw them both nod again.

"Good, good. We'll alert all the winners via the email on your entries. Winners get their trip paid for, airlines, hotel and transportation, as well as further rules and instructions. All instructions must be followed to the letter or may result in immediate disqualification. Do you have any questions?"

Rebecca started to open her mouth before he cut her off.

"NOT about the contest," he smiled.

"Well, we did have one question. What's the rule on the observer? We'd like to bring one for....at least SOME safety."

"Understood. You are allowed one observer, who must follow our observer protocol. He or she does NOT get travel paid for, that's on you. You'll receive more details in our contest packet at the hotel, should we accept your entry as final."

Another week went by. To say Rebecca was edgy was an understatement. I hadn't heard from her in three years, now, she was texting me every day, calling me, mostly for emotional support.

"Why haven't they emailed? What if we aren't sexy enough?" "Oh god, what if we get caught? I spend every night fighting the urge to get out my dildos or vibrators and just work myself over....but I don't. I seems spend half the day with wet panties, the other half doing laundry," she laughed.

I didn't hear from her again until a week before the trip.

"We...got the tickets," she whispered excitedly. She was at work. "You need to get your airline ticket." she gushed.

"Yes, I'll get one for Saturday, early, so we have time to meet up and discuss things."

"Good. We're on the 2pm flight. Our hotel is the Plaza East, it looks really fancy. I'll text you when we get the key and the room number. See you then, oh my god....this has been killing me. I can't wait!"

I was going to share their room, a thought which gave me my own "ideas." I sighed, though, I knew I wasn't going to get any action because of the contest. Still, to be around two such beauties? All worth it. I met them in the hotel lobby after they texted me upon their arrival.

"God, look at this place!" Parker gushed. "It's like totally for rich people!"

They were both giddy. They nearly raced up to our room. No sooner than they'd opened the door they both raced to one of the beds where a package lay. They ripped it open like kids at christmas. There was a letter with several pages.

Contestants: 1- you must retrieve your necessary items from the promenade room. Show them the I.D. tag. 2- you must sign all waivers and non disclosure agreements (NDA's). 3- you must report to the spa for prep. You are to follow their instructions, no exceptions. 4- you are allowed one observer. You must retrieve his/her items at the promenade. 5- read the rules of the contest carefully before you sign.

Parker read the rules to us as we stood there, mouths agape.

Rules of the contest:

The contestants must complete their prep before the contest.

Contestants will be ready for transportation the morning of Saturday, October 30th, 6am. If you are late, you are disqualified.

Contestants/observers will be ferried to the island and dropped off. Only items allowed/provisions will be supplied at the drop off (point A). It is strongly urged to wear a good pair of boots suitable for hiking in different conditions.

You will be given a map and provisions. You are to make it to "point B" on the map before being caught. There will be a red "finish line" to cross. If successful, you will be paid the agreed upon amount of $10,000 dollars. If you are unsuccessful and are caught, you are property of the hunter until the ferry arrives for final departure on Monday, November 1st, at 11am."

They both looked at each other wide eyed. I did NOT see reluctance as much as thrilled agony. They both wanted this...challenge. They raced down to the "promenade room." They were met in the hallway by a beautiful asian woman with an all knowing smile. I was not allowed to pass, since they had the I.D. badges and I did not. Rebecca called me later and told me the story, with Parker still busy with the prep.

"Li, the asian woman, did you see her? God, she's gorgeous, if the contestants are all like that how did we get chosen? Anyway, she took us into a private conference room, using a security key. Inside, there were already a handful of other contestants there picking up their stuff. God, they are all beautiful, and YOUNG! Most of them look like athletes, how are we going to compete against that? One of them looks like an amazon! She's got muscles all over and has pink hair and huge tits. She looks like she could break me in half!"

"We picked up our things. It was a very small backpack. It just has two water bottles and a first aid kit. Then, we all stood in line in front of a guy who was probably a lawyer. He made every one of us sign each page, explaining each in detail before having us sign. Do you know how embarrassing to have to "agree to anal intercourse? Or, do you prefer crops, belts, whips, or hand spanking?" in front of a group of women? Anyway, we both signed. We were then instructed to go to the private spa. Li led us there together."

Inside, they told us to strip. We were in a room with two tables, like for massage. I thought, "oh cool, we're getting free massages!" Instead, an older native american or Polynesian looking woman came in and gave us the eye."

"Table. You," she said, roughly pointing at me. I laid on my back, nude. She said, "no hair! Read rules!" I thought, "what the hell?"

"She pointed at my pubic hair. "Whew, I thought they wanted to shave my head."

"I asked for a razor, but she had one in her hand already. Without warning I felt her splash my pussy with warm, soapy water. Just as shocking, I felt her fingers massage in the soap, which included them sliding over my pussy lips. I'm sure I involuntarily sighed, you KNOW how long it's been since I had anyone touch me there," she chuckled with a blush."