Chapter TWENTY-ONE
(Charlotte)
From our weird phone call on out, everything about the Ascend Red trip had accelerated at a dizzying pace.
First of all, the email from Matt’s assistant had been…
Eye-opening.
Sure, Matt had warned me that I might be shocked, but I’d had no idea how frank it would be. There was a questionnaire with sections about blood play, water sports—not the kind with boats involved—, various types of bondage, electrical stimulation, even some things I had to look up.
For the most part, I was down for anything not involving bathroom activities. I’d carefully ticked off the correct boxes and sent it back with copies of my driver’s license, passport, most recent STD screening results…
This place was thorough.
Ascend Red had been described both in the email and by Matt as an invitation-only sex island, whereas the other Ascend properties were more like laid-back all-inclusive swingers resorts. I’d taken the exclusivity of Ascend Red with a grain of salt. As a marketing gimmick.
It most certainly was not. The list of “member conduct” had all the things I’d hoped it would have regarding consent, but the privacy policy was serious business. It flat out mentioned blackmail and criminal penalties. In other words, the people who came to Ascend Red were the kind of people who had something to lose.
Getting to the island itself had been an exercise in unbelievable luxury; first-class to Montego Bay, limo to the marina, then a yacht out to the open sea. I'd even been escorted through customs in a priority line.
A speedboat took me from the yacht to the docks at Ascend Red. As soon as I stepped onto the concrete pier, my giddiness at the luxury accommodations plunged into a slap of reality. Matt owned all of this. The dock, the boat, the castle that gleamed on the small island's highest peak. It all belonged to one man, and he was the one who'd sent for me.
Matt very much stopped being my brother's best friend in that moment, and became someone else in my mind, someone mysterious and powerful. Maybe that was the point of the yacht and the boat and even the freaking castle: to flaunt his total control over this tiny kingdom of debauchery and establish himself as an island of his own.
A slender woman in a surprisingly conservative gray suit met me dockside, smiling warmly. "Charlotte?"
"That's me," I said, looking behind me instinctively to pick up my carry-on, but like every other step of the way, someone magically whisked it away for me.
"I'm Miranda," the woman said. Her deep blue lipstick and sleek, slicked down ponytail should have been out of place with the rest of her outfit, but somehow it all worked. She tapped something on the tablet she carried like a clipboard, her eyes darting from mine only briefly to complete the action. "Mr. Ashe has been informed of your arrival."
"Cool, so he's..." I looked past her, as if I would see him stride across the beach toward us. But there wasn't anyone on the beach. The only people currently on the pier were guys moving luggage and tending to boats. Whatever else happened here on this island, it was happening behind the tall, forbidding stone wall ahead of us.
"You'll be taken to his private residence after check-in." Miranda reached into her bag and retrieved a phone. "I'll need any of your devices with recording abilities. While you're here, feel free to take and make calls from this satellite phone, in unrestricted areas, of course. But all recording devices are strictly forbidden inside the compound."
"Right." I'd known about that from the documents I'd received before my trip. I slipped my phone from my back pocket and reluctantly—but only because I was addicted to it—turned it completely off. It was a small price to pay for what I knew was about to be an unforgettable week. And I understood the need for privacy. Not only were some of the island's clients rich and powerful, but even the most anonymous person on the planet wouldn't be able to truly let go if they knew there might be a lasting record of their deeds.
"There is a red icon on the lock screen that will instantly summon resort security to your location. If you press it by accident, don't worry. Sometimes it happens and they're used to it, but they do have to respond in person." She tapped her tablet again. "And we did receive your NDA and signed acknowledgement of receipt and review of the handbook..."
I nodded along, but her inventory was clearly for herself.
"All right, it looks like everything is in order. We can go inside." Miranda made an "after you" gesture, and I walked ahead of her down the pier.
The transition to land was a gentle slope onto a wide terrace of polished concrete, embellished with the occasional impression of a seashell or a fossil or... I squinted down as I stepped over one. A belt buckle. The stone fence was a lot taller than it had looked from the boat; it was easily twenty feet high. The bronze torches bracketed to the stone weren't quite medieval, but the theme was starting to come together in my mind.
At the moment, that theme was "Pier One Imports does a Renaissance Fair."
I wasn't hating it.
A gothic arch with carved figures loomed over the much more sensibly sized double doors at the entrance. As we got closer, I noted that the bas relief scenes depicted wouldn't have been appropriate on a cathedral. There were certainly scenes of torment and flagellation, but the wrong kind for salvation purposes.
I didn't know what I'd expected; who knows what to expect from a sex resort? But aside from the uniformed staff working on the pier and the two stoic security officers standing beside the doors, the place seemed deserted. I'd expected tits and ass and people being walked on leashes the second I stepped off the boat.
Miranda nodded to the two men, who nodded back and opened the doors for us.
And that was where all the people were. I stood rooted to the concrete, my greedy eyes taking in more naked flesh than I'd ever seen in one place before. Bodies of all types, from lithe to generous, gleamed in the tropical sun, relaxing around a huge, circular pool with an enormous fountain in the middle. Some guests reclined on lounges while resort staff fanned them with palm fronds. Others cavorted in the water, some playfully, some carnally; an incongruously innocent splash fight was happening about two feet from someone getting their pussy eaten by someone else getting fucked from behind. People were sipping drinks and relaxing to the usual poolside sounds mingled with moans and grunts, as if it were the most normal place to be.
Oh, and there was the person being walked on a leash. Right on time.
"Welcome to Ascend Red," Miranda said, swinging her sleek ponytail. This moment of shock was obviously a favorite part of the job.
"I..." My jeans and t-shirt felt immediately stifling in the heat once the presence of a pool had been introduced. "I'm overdressed."
"Not to worry," Miranda assured me. "We'll get that taken care of at check-in. If you would follow the red line?"
I looked down. Red glass tiles embedded in the concrete formed a border around the textured floor of the pool area and widened into a curved path like a satanic yellow-brick road. I followed it, looking back to make sure Miranda was still with me. I'd thought coming as a guest of the owner would have meant I could skip the front desk.
The red path diverged into a fork at the other side of the fountain and Miranda directed me to the left, past a potted palm currently being used for balance by a couple engaging in some vigorous standing intercourse.
"Is it rude to stare?" I asked Miranda, lowering my voice. Not that the couple would have overheard me, anyway. They were both practically screaming.
"If something is happening in a public area or a voyeur zone? No," she answered.
Voyeur zone. I recognized the term from the handbook. There were "private" spaces that could be used by people who either wanted to be seen or simply didn't care, but which could only be viewed from peepholes or other hidden vantage points.
It had been one of the first things I'd added to my to-do list.
"Private rooms, however, are strictly controlled by our consent policy," she continued.
"Thanks," I said, relieved but also a little embarrassed that she added that last part. "I did read the handbook, I promise."
"There was a lot of information in there," she said with an understanding smile. "If you have any questions, there is always someone on staff who can help. Although, I'm sure Mr. Ashe can answer those questions, too."
"Yeah, where is he?" The open-air fuck-and-suck fest had been a hot welcome, but I'd come to the island for Matt.
"He arranged a special check-in procedure for you," Miranda explained. "So, you won't see him until you're finished at the spa."
A spa appointment? The man certainly knew how to woo me.
In fact, the spa was the destination Miranda led me to, not a hotel lobby. The red path ended in a loop around another, non-swimmable fountain, through a pointed stone arch and into a peaceful, deserted courtyard, where a gray stone building butted up to the perimeter wall. Over the glass doors, the words "Eros Spa" were engraved in a brushed-steel plate.
The name was shockingly familiar. Did Matthew frequent the same section of Literotica.com that I did?
I hoped the inside was as good as the story.
Before we even reached the doors, two staff members appeared to greet us. One was a stereotypically Nordic-looking guy with huge shoulders and bulging biceps that threatened to burst the sleeves of his pristine white polo. The other was a petite woman with ivory skin and mousey brown hair pulled back in a no-nonsense French braid and a similar uniform to her giant Viking counterpart.
"Welcome, Charlotte," they said in unison, and I decided that I was out of there at the first sign of a flower crown.
I was not about to get Midsommered at a sex resort.
Luckily, they dropped the creepy vibe instantly. The guy introduced himself as Canson, which had to be a fake name, but the woman looked like the Beth she claimed to be. I supposed if I worked at a private island sex retreat, I probably wouldn't give my real name to guests, either.
"I'll leave you in their good hands," Miranda said, adding, "Mr. Ashe would like you to know that he'll be viewing parts of the process."
That was a big clue that my "special check-in procedure" was going to be filthy as hell.
Inside the disappointingly futuristic-fucking-machine-free spa—not everything could be like internet erotica, I guessed—Beth led me to a changing room outfitted with a luxurious multi-head shower and all the toiletries and tools one might require to make themselves presentable to the world again after their facials and massages. Totally standard; I'd spent enough of my parents' money on pampering over the years to have seen similar set-ups. I stripped down and took advantage of a quick shower, then put on the fluffy, pre-warmed robe Beth provided.
For the most part, everything was normal. Mimosas and a pedicure, an offer of waxing that I declined having taken care of my business at home, and then it was off to my massage, where I met up with Canson once more.
"Enjoying your day so far?" he asked cheerfully as we entered another fairly standard spa room. The lights were low, essential oil scenting the air from a warmer, and a crisp white sheet draped over the massage table.
Beth entered, carrying a foam wedge under her arm. "All right, Charlotte. Why don't you get rid of that robe and hop up on the table?"
Whenever I'd had massages in the past, the therapist had always left the room so I could disrobe and cover myself with a provided top sheet. Canson and Beth waited expectantly.
"If you're feeling self-conscious, I can take this off," Beth said, gesturing to her own clothes.
"So can I," Canson offered.
My eyes were probably wide enough they could both see my brain. "No, you're fine," I said breezily, as if strangers offered to get nude for my comfort all the time. I shrugged out of the robe, too aware of the way my nipples tightened at the first touch of the air on my skin.
Beth took the robe and Canson patted the table. "On your stomach please," he instructed.
I laid down and wriggled into a comfortable position, settling my face into the headrest. Beth patted my thigh. "Could you lift your hips, please?"
Okay...
She slid the wedge beneath me, raising and tilting my pelvis at an angle that fully exposed my pussy to both of them.
I assumed this would be the part that Matt watched from wherever he was.
"Comfortable?" Canson asked, his huge hand resting on the curve of my calf.
I somehow squeaked out a "Yes," and forced myself to slow my suddenly erratic breathing.
"Relax," Beth reassured me, and I heard her slicking her hands with oil. "We're here to relieve all of your tension."
Heat flooded straight to my vulva. I took a long, deep breath and prepared for them to touch me.
They did, but not in the way I expected. Beth started at my shoulders and neck, and she put in the work easing the knots caused by a long day of travel. Canson started at my feet, doing a more thorough—almost painful—foot rub than I'd received during the pedicure. They were good at their jobs, so good that they lulled me nearly to sleep as they tended every muscle between my head and feet.
While I drifted off into half-slumbering bliss, some part of my brain noted that Canson's hands were getting awfully close to my upraised vulva. So close, his liberally oiled fingertips accidentally brushed my folds. And when Beth reached my ass, I couldn't help but notice how often her strokes parted my cheeks. A drizzle of something warm and wet between them shocked me back to full awareness.
Wordlessly, Canson and Beth stood on either side of me. His thick, powerful fingers moved in surprisingly delicate strokes over my labia, trapping each fold between his fingertips and massaging them, too, working the hot oil into every crevice. The only area he avoided was my clit, which pulsed with longing every time he came near it.
"You're very tense here," Beth said, her tone taking on a teasing note as she pushed her slender finger against my anus. "Mr. Ashe made it clear that we were to provide thorough relaxation and preparation."
I made a strangled noise.
This is what you're here for, isn't it? The horniest part of my brain shouted at me. To experience new things?
"I'm going to use my thumb to try to get some of this tightness out," she told me, and pressed firmly around the rim of my asshole.
"You look a little stiff here," Canson said, sliding a finger on either side of my clit.
I moaned aloud.
"Let me see what we can do about that." He squeezed the knuckles of those fingers slightly together and gently rocked his hand. "Now, it's important that you don't tense up."
That would have been a lot easier if my body wasn't weeping for release already. And I meant weeping; the fluid dripping from my clutching cunt wasn't the massage oil.
Beth's thumb pressed forward. I fought my body's immediate response and kept my muscles relaxed like Canson had instructed. There was pressure and resistance, but no pain when she breached my hole, and I gasped as the oiled digit penetrated me all the way to her hand.
"You're tensing," Canson said.
"There's a lot of internal tightness," Beth noted. Their clinical speech patterns were driving me almost as wild as their hands. Because there was nothing sexual about their words, the pleasure I felt seemed out of place. Like I was doing something wrong, like I shouldn't be thinking of or wanting an orgasm. That this was a massage and I shouldn't be getting off on it, despite the fact they were clearly going to get me off.
"Maybe you can give me a hand?" Beth suggested to Canson, who slipped a finger from his other hand in my cunt.
I gripped the sides of the table.
"Like that," Beth told him, pressing her thumb down in firm circles that he repeated from below. Their fingers touched, separated only by the wall between my intimate passages, and I moaned.
"You're tensing up," Canson warned, his knuckles alternating the pressure on my clit.
Relaxing made my impending orgasm seem too far away, and I gasped in frustration.
"I do tense up when I come," I told them. "Don't most people?"
"They do," Beth agreed. "But our job isn't to bring you to orgasm."
"Then you're doing a terrible job," I laughed in dismay.
"Mr. Ashe has strictly instructed us not to let you come, I'm afraid," Canson said, withdrawing his finger a little to access my g-spot. "Which is exactly why you need to relax."
"I think you're ready for the final part of your treatment," Beth said, withdrawing her finger. I groaned in frustration as Canson removed his hand, as well.
I lifted my head to see Beth take something from a small wicker cabinet. "What's the final part of the treatment? You show me an ice cream sundae and say I can't have it while putting the spoon to my mouth?"
Canson chuckled at that.
"No, silly," Beth said with a laugh. She turned and held up a spool of wide red satin ribbon in one hand and a small steel butt plug in the other. "You've got to be giftwrapped for Mr. Ashe's birthday."