The Wilfree Ch. 01: Clover Pool

It was the quiet season. I was standing naked in front of the glass balcony doors of my 2nd floor suite of the Wilfree Estate, the center of life, culture, and expression for this small private island.

I curiously watched the staff tidy up the courtyard and the pool area below as the bright sun began its daily descent behind the deep green ocean out in the distance.

There were still a few clients around, soaking up the warm rays of the sun. Most were gathering up their clothes and accouterment and heading in to get ready for the evening's affairs. The staff was patiently working around them.

Over by the bar, it looks like a contract or special request was taking place. A sexy-looking Latin lady was laid back over the bar with her legs spread wide, getting pounded by one of the staff while the bartender and a hostess held her hands above her head. They both caressed her big bouncing tits while they watched the staffer's shaft forcefully disappear deep into her willing pussy. I would rate it as a decent variation on a common request for this place.

It felt good to relax for a minute and let the warm light from the window touch my naked skin. I could feel the heat settling on my cock. It brought my focus back from the goings-on at the bar. I had my own contract later today. I needed to start getting prepared. So, I reached down and casually started fondling and stroking my warm member.

This was a straightforward contract, one with a long-time regular. She flies in later today. We don't see each other much beyond our long-standing contractual agreement, part of which includes the arrangement that I am the first person to greet her when she arrives on the island. She should be texting in a few hours. It does feel good to think about her while I rub my semi-stiff cock.

I stroll through the glass doors onto the balcony facing the courtyard. The heat falling on my body increases while I gently stroke my cock and balls. I return to surveying the grounds. The Latin lady is lying on her stomach now, satisfied. Her tanned, relaxed, and freshly fucked body is leisurely stretched out on the bar while she is sipping on a mixed drink and chatting it up with the bartender. He seems cheery and rather animated telling some story. She has a nice round voluptuous ass. He keeps resting his hand on the ass cheek closest to him, caressing and playfully spanking her while they talk. He will have an entertaining and busy few days, it looks like.

I hear one woman's voice call out my name, "Jack! Hey Jack!"

I look down into the courtyard. It's Lana. She is somewhat new to the staff and was working in the courtyard today. She came on board last season as a lobby host and fit in well from the beginning. It takes a particular type of person with no inhibitions and a truly high-level sex drive to work here for any extended length of time. Most people, men, and women, both burn out or can't handle the emotional baggage this place will deliver to you. I've been here for ten years. I've seen a lot, and it still fucks me up.

"Jack, Hi! How have you been? I haven't seen you in a couple of months."

"Pretty good. I've just been swamped. Had a few long excursions and such." I answer while standing on the balcony, fondling my now fully erect dick.

Lana replies, "I'm pretty much done out here for now. Come down and give me a proper hug."

There were still a few clients milling about and a couple of workers serving them or tidying up. I could hear distant orgasmic moaning coming from the other side of the pool. A client was on all fours, doggystyle, with a big bubble booty high in the air. A hostess was rhythmically sliding a colorful glass dildo in and out of her asshole while three fingers on her other hand vigorously massaged deep inside her wet dripping pussy.

The suite I'm staying in has a stone staircase leading down to the courtyard, so I wander over and make my way down. The afternoon sunlight has become hot on my flesh. My cock, without the attention, starts to make its way back to its flaccid state.

As I step off the stairs, I feel the cool, perfectly manicured green grass under my bare feet. Lana strolls towards me with the casual, eager stride of a long unseen friend, extending her arms big and wide, yearning for the hug she requested.

She is shorter than I am and has a delightful smile and warm inviting eyes. Her hair is sexy, easy, and a wavy brunette. Today, while she is working outside, she has it bundled up in a hair clip. She has an athletic yet curvy build and always has a great outlook on life.

When she got close, she hopped up on the tip of her toes and flung her arms around my neck and her body against mine. My naked hips and bare cock could feel the slight coarseness of her uniform's pleated skirt. As she slid off her toes, I could feel the coarseness teasing my body with a little hint of pain.

She said cheerily, "It's so good to see you! We've missed you around here. It's never the same when you're gone."

"I'm glad to be back."

We turned and started strolling towards the area where she was working. As we turned, I put my arm around her shoulder, and she slid hers around my waist, and we pulled each other close. Before she could even finish her first sentence, her hand slid down onto my ass cheek. she was rubbing it in a big giant circular motion and grabbed a handful of my flexing glute as we took steps. I could feel her nails sinking into my flesh a little and it felt good.

Lana quipped, "I've missed seeing your ass around here. While jiggling that handful she was gripping."

We both chuckled and kept walking. It wasn't anything unusual for folks to be in different states of dress, including fully nude, aroused, or sexually engaged. This estate and, in fact, the entire economy on this island was founded on the principle of freedom of human expression and openness of self. It is the reason I came here, the reason I now work here. White Veil Island and the Wilfree Estate is a wholly unique, one-of-a-kind, and truly hidden gem of the world.

She said, "So are you working right now, or are you just having a little public "me" time? We were all ogling over you stroking your sexy cock up on the balcony."

"I'm just getting ready for work. Probably in the next hour or two." I said matter of factly.

Lana quickly responded, "Let me guess! Either you have a Cum-Wine-With-Me-dinner...or...Ms. Tally Hersh?"

I smirked at her insightfulness, "It's Ms. Hersh. She arrives in a little while. I've just been edging today to get ready."

Then I proceeded to grab my cock and start massaging it again while we walked. I should stiffen up a few more times before she arrives.

Lana responded, "I should've known it was her. You are the only 'Casanova' I've seen stroking around here today. Not talking shit about you but it takes more than one cock full of hot cum to fill up those wine cups for all those kinky cum drinkers...and damn, do those ladies love you all.

I love watching you guys magically make all those women drip between the thighs without even touching them. And watching you all dance on that big, long dinner table above them with your big dicks swinging in their faces...watching them suck you all until you're hard...then fucking their faces as the appetizer!

It's not my kink, but serving in the dining room while the show is going on is one of my favorite assignments. And the best part is watching those women get flushed and yearning for your explosion into each of their glasses so they can raise them up for the traditional "white wine" toast before gulpng down your fresh juice. And then...the ravenous moaning and begging for more loads to fill those emptied and clean-licked cups. Fuck it's so intense."

My cock started getting a little firm listening to my friend recount the Cum-Wine-With-Me dinners. I keep stroking while reminiscing about those crazy parties. We reached the lounge chairs she had straightened previously.

"Damn, I'm a little wet thinking about it...look." she said excitedly.

She proceeded to plop herself down and throw herself back on one of the chairs, pulled her knees up and open to reveal the wet spot on her perfectly white thong panties she was wearing. She rubbed two fingers over the spot and then circled her hidden clit as she let out a tiny exasperated sensual moan.

She looked up at me, raised her hand, and held it out for mine. I took it, and she pulled me down, wanting me to sit on the end of the lounge chair with her.

I hesitated because I was fully nude and had nothing to put down or sit on the lounge chair. It is a standard hygiene practice not to sit on the furniture without a seat cover of some type. I know it's silly considering what we all do here, but it's a courtesy practiced universally on this island and elsewhere.

She noticed the hesitation and immediately realized why. I was butt naked and had nothing but a semi-hard cock in my hand.

She glanced around quickly and determined that there was nothing to use.

So, in a typical Lana improvisation, she pulled her little monogrammed uniform tank top off and spread it out on the end of the lounge. This awareness is why clients adore her, I thought.

She wasn't wearing a bra, which is not unusual. Most women didn't wear them on the island unless it was sexy lingerie or some functional bra for excessive physical work or something.

Anyway, she stripped off her top, revealing her nice pair of tanned and perky tits. She had dark round nipples neatly topping each full and soft breast. The day was warm, and she had little glistening sweat droplets scattered up and down the crevasse between them. She was a beautiful, generous friend, happy to be of service to me and clients alike.

Now, she gave a quick little pat on the new place to sit on the lounge and leaned back, taking in the fresh air on her newly freed chest. She put one arm behind her head, spread her legs, and gave her wet spot and her hidden clit another couple of strokes, the same as before.

I got comfortable on the chair with Lana. I let one leg fall off the lounge and opened up my other leg facing her. I propped myself up with one hand behind me and took my semi-stiff cock in the other. I slowly gazed up and down her sexy, hot body. Her exposed tits and that little blue pleated skirt pushed up on her waist, and that tight, now transparent white, wet little strip covering her aching slit was electrifying.

"Holy shit...reminiscing about you boys, the cum drinking ladies, and you stroking right in front of me makes me so hot! I wish you could rip these soaked panties off and shove that thing deep down inside my aching sex. Fuck!"

With that said, she raised her chin, rolled her head back, and arched her back while both hands squeezed her wet lips together. She was amazing to watch. My cock was fully erect and throbbing.

Almost instantly, after what seemed like a hint of an orgasmic shutter through her legs and belly, she sat up, crossed her legs, and leaned forward onto her elbows with her hands under her chin. She was just inches from my hot, stiff cock.

"I see you're a little excited, too," she said with lustful eyes and a sly little smirk.

"Of course, you're sexy as hell," I said.

Lana, "Thank you. And, I know the rule... '-- Among staff while working on site, everything is permissible EXCEPT penetration. Section 1.8'"

"Yes, that's the damn rule," I say with a little disappointed grin, a mask for my ravenous desire.

After a moment of shared frustration, she says, "Well then, let me help you with that."

She quickly pushes herself up with one hand and craftily slides her other hand under my hot hanging sack. I feel her wrap her fingers around my balls and give them a gentle squeeze and tug. The surprise touch sends a shock from my jewels up the shaft of my pressure-filled cock. And just like that, Lana is massaging my rock-solid, hot, throbbing manhood.

She adds, "I know what your contract is for today. I promise Ms. Hersh will get everything she wants after I work on you for a little while."

I feign misery and jokingly retort, "This is torture, you know."

With a sweet, devilish tone, she replied, "Nope, just work, and my momentary guilty pleasure. Just lay back, relax, and focus on not cumming even though I'm taking you there."

So I did. We continued to chat casually and catch up on the gossip and latest rumors in town. She continued to intermittently stroke, massage, and squeeze my manhood where and when appropriate.

She was masterful at multitasking and was paying attention to all the physical cues of my body and the manifestations of my suppressed sexual releases. I could no longer bear looking at those sumptuous tits freely dangling in front of me with erect tanned nipples ready for stimulation.

She was good, honestly perfect, and all I could think about was grabbing her hot, sweaty body and throwing her back down on the lounge. Then, taking a bite of one of those tasty areolas while flicking that hard nipple around my mouth with the tip of my tongue. All in the seconds before grabbing her knees, forcing them out, and sinking my rock-hard, overstimulated...

Lana, "Oh...Hey Tricia!"

And just like that, my brain and my savagery were sucked back into my body. My mind reconnected to reality.

The reality was that Lana was still meticulously stroking my engorged cock, which made me unaware Tricia was meandering by with a couple I can only guess were new clients who, at first glance, seem nice enough. They looked curious, excited, anxious, and unsure all at once.

And Tricia...She had a nice "fun-sexy" look going on today. Her dark skin was sumptuous under the bright white of the Wilfree uniform top she was wearing. She had on the women's button-down shirt, unbuttoned. The top was splayed open, exposing the insides of her naturally robust boobs, and neatly knotted above her naval. It matched some fashionable, mostly white sneakers and knee-high white cotton socks with little red and blue stripes at the top that perfectly contrasted her chocolatey dark, long, and powerful thighs. Where her legs left off, a pair of sheer red booty shorts began. They were stretched over a curvy, voluptuous ass that I have had the pleasure of watching devour my cock during contract for a client. She wasn't wearing anything under them, and I was in admiration of the glistening lips of her fully shaved vulva pressing against the thin red mesh.

The couple was wearing friendly, standard summer fare, she in a sundress and he in a comfortable white linen shirt and pair of yuppie khaki man capris that cuff above the ankle. He was trying to play it cool. His hands were in his pockets; he was standing slightly behind Tricia and the blonde in the sundress. He looked apprehensive, like a duck out of water. Her eyes were big, blue, and bright and locked on the attention Lana was giving to my groin.

Tricia cheerfully responded, "Hi Lana! Looks like you two are enjoying the sunshine today."

Lana smiled big, "We are. Jack and I are just catching up. Haven't seen each other in a couple months..."

One hand was cupping and fondling my balls, the other pulling a teasingly slow, firmly-gripped stroke of my shaft.

She added, "...so I volunteered to get reacquainted with one of my favorite tools on the grounds and help Jack prepare for his contract."

She was managing my intense sexual desire and working the crowd all in the same moment--a wonderment of skill and composure.

The blonde woman looked flush in the cheeks now, and it was creeping down onto her chest. She had blonde, wavy, shoulder-length hair and a reasonably small chest. Although I'm guessing her tits were perky behind the somewhat loose-fitting sundress top. Her gaze was that of an antsy child waiting for her turn to get a sweet treat from an old-time candy store.

The conversation had pulled my attention away from my dick. It was an unwelcome moment but certainly necessary if I was going to contain my energy for Ms. Hersh's arrival.

Noticing the falling state of my cock Lana coyly asked the blonde, "Wanna have a touch? Jack doesn't mind. Looks like I could use some help to perk things back up."

Tricia promptly interrupted, "Well...Mr. and Mrs. Kenning haven't signed on the dotted line yet, so we don't have their Consent Profile just yet. They were just taking the eye-candy tour."

Disappointment took over the blonde's face. She turned and looked at her husband and Tricia with some big, sad puppy dog eyes.

She spoke with a bit of a spoiled tone, "Oh come on!?...just a little bit. Please? We are definitely joining, so what is it gonna matter."

All three continued chattering about the details.

Lana got back to work on my body. She was rubbing and massaging all the tender skin and muscles around my groin and up my waist. While I was preoccupied watching the couple and Tricia negotiate a silly impromptu sexual plea deal, I felt her hot wet mouth slide over the head of my cock, sucking all the blood up to the tip of my dick.

My eyes went out of focus. I heard myself mutter, "Holy shit..."

I looked down. At the same time, the blonde, the man, and Tricia all stopped talking and jerked their heads around and locked in on Lana as well.

She had changed positions and was now on her knees. Her fucking sexy, round mounds of ass cheeks pointed skyward, beaming with the glow of the sunlight. The white strip of her thong lay perfectly straight in the valley between them. Her skirt was still tangled high around her waist. She was on her knees and elbows looking up at them. She was grinning but with her mouth wide open. My dick, with a newly bright red, engorged head, was resting on her wet, outstretched tongue. She flicked it around and traced the curvature of the rim.

Mr. Kenning muttered, "Um...I don't...I mean, we...I guess..."

Tricia said, "OK then."

The blonde slowly turned, got down on her knees, and placed her hands on the lounge. She watched Lana devour my cock one more time and slowly pull her vacuum of a mouth ever so slowly up my firmly erect cock again.

Lana let out a long "Mmmmm..." while her mouth was full.

This teasing is beginning to be too much. I'm starting to think I won't be able to contain myself until my appointment. I'm feeling the uncontrollable, primal energy coursing through my veins, and I'm about to have an excited, eager novice feeling herself around my body. I love the energy of fresh faces, anxious beginnings, and exciting discoveries made by new clients at the Wilfree.

I grabbed Lana's head with both hands. I pulled her up to me. Her bare breasts raked over my throbbing cock. I glanced into those deep, dark eyes, lifted her chin, and gave her a genuine, caring, and sensual kiss.

I heard a faint gasp and an exhilarated, soft exhale escape from the opened, smiling mouth of Mrs. Kenning. I felt her hand slide over my leg and slowly start feeling her way up the inside of my thigh.

At this point, there is no contract with this couple, so I have no idea what they are into, what the expectations are, or what limitations they have.

With the title of "Casanova" and the most senior staffer of the Wilfree in this little random group, I figured I better control this situation for them and for me.

I looked up at the husband and spoke directly and succinctly, "Sir, what's your name?"

"Bill...and this is Marie."

I replied, "Do you consent to your wife having casual, sexual contact within this small group standing right here?"

He hesitantly confirmed, "Yes?"

I asked Marie, "Ma'am, do you consent to your husband having the same among us?"

She quickly and excitedly replied, "Absolutely! Can I touch your cock now?"

"No."

I told Tricia, "Go tell one of the other hostesses to report this as an SVC, then hurry back."

With that and the firm rejection I just gave her, Mrs. Kenning stood up and stepped back beside her husband. She was slightly embarrassed. The nervousness returned to their faces.