Her Brother’s Billionaire Best Friend (Her Billionaire #1)

Chapter TWENTY-FOUR

(Matthew)

“Yes, the resort is staffed with sex workers,” I explained—again—to Charlotte as I navigated our golf cart around a particularly tricky curve in the path. It wasn’t that she hadn’t read the handbook, she’d had a difficult time grasping the concept of everyone being available for anything on the island.

“Right, but it said staff members could indulge or decline guests’ advances,” she said, a point she’d brought up twice already.

“Like I said, why would the consent rules not apply to the staff?” Violating the rules meant losing your job or your membership, depending on which side of the guest/staff relationship they were on.

“They clearly should. I think it’s… I don’t know. It’s difficult to imagine a place like this and wrap your head around it. Sometimes you fantasize about taking a hot waiter home, you know?”

“I do know,” I answered her rhetorical question.

She went on. “But you know you shouldn’t even suggest it because they’re at work and they have to be nice to you and you’d be a creep. It feels like if everyone who works here is paid to have sex with me, it’s a license to be a creep.”

“These are professionals.” It was the only ethical way to run a resort like this. “Professionals who understand the fantasy and kink elements that go into the Ascend Red experience.” I cringed. “Yikes, that sounded very brochure of me.”

“I’m worried,” she admitted as I pulled us into a space behind the castle. “What if I’m not free spirited enough to appreciate things here?”

She’d been eaten out and roughly fucked during breakfast. “I don’t think you have anything to worry about.”

But I understood where she was coming from. I turned off the cart and put an arm around her shoulders. She’d worn a fluorescent green bikini that pushed her tits up, and all I wanted to do was rip the straps right off—

I cleared my throat and collected my thoughts. “The concept of Ascend Red—how it runs, the sexual freedom from the moment you arrive here to the moment you leave—baffles a lot of people. It can be overwhelming. When you return to the world outside, that’s when you appreciate it the most.”

“Is that what people tell you?” she asked. “Or is it part of the ‘Ascend Red experience?’”

“Can we pretend I never used that wording?” I shook my head with a reluctant laugh. “But really. It’s something I felt the first few times I came here.”

“But you’re the one who designed it,” she said, narrowing her eyes.

“I designed it. But I hadn’t realized what it would feel like to be here, in a space where truly, anything goes, and you can have whatever you want.” I paused. “I’m mindful of the fact that I own this place, though. I only play around with staff members I can trust to be honest with me, and who won’t feel pressured to do things they don’t want to do because I’m their employer.”

She relaxed. “I’m glad to hear you say that. I guess it’s what I was worried about, in the first place. That nobody here could consent because you’re their boss.”

“I’m never involved in hiring or firing situations,” I added. “I’m not anyone’s boss. I’m just the most important guest. Hence, my caution.”

“That makes sense.” Seemingly satisfied with my answers, she turned and swung her legs down, the lacy shawl tied as a makeshift skirt around her waist parting to reveal one long, slender leg.

I grabbed my cane and hopped out; it was a good day. Maybe having Charlotte with me was some kind of painkiller. Still, I didn’t want to chance a fall, so I’d brought the cane as an insurance policy. I reached for the other set of keys in the pocket of my shorts, and she groaned in dismay.

“You wear dad shorts.” She scoffed dramatically. “You’re old enough to be my father and you’re wearing dad shorts.”

I could take some gentle ribbing about our age difference, but that was a low blow. “I am not old enough to be your father. I would have had to have been in high school.”

“People get people pregnant in high school. I don’t know what to tell you,” she sing-songed, following beside me to the private entrance to the castle.

“If you want to call me Daddy, say so,” I huffed in half-pretend annoyance. “But you’d better be into spanking.”

“Oh, I am!” she assured me as the door opened. Then, her voice cut off abruptly.

The private entrance led immediately into my box high above the “theater.” Though the room was empty of people at the moment, it was impressive enough on its own. Decorated like a scaled-down eighteenth-century opera house, the theater was equipped to host any number of performances.

For example, the go-go cages on either side of the stage could be occupied while someone was flogged, fucked, or otherwise exhibited. The floor could be filled with seats for an audience or cleared away for something more interesting to watch from the mezzanine. There were blue tarps and a huge inflatable pool set up.

“I believe tonight is the lube orgy,” I said, pointing to the waist-high pool. “That will be filled up, and they put in small ones there and there—”

“That sounds amazing!” Charlotte clapped her hands excitedly. “Can we do that?”

“You can do that while I watch.” It took way too long to shower that stuff off, once you’d dipped yourself in it.

“Okay.” She sounded a little disappointed. “I don’t want to do whatever I want while you sit around and watch. I want to fuck you too.”

“Do you think I’m letting you leave here without doing me more than you do anyone else?” I gestured to the second door in the box. This one locked from the inside. “After you.”

We walked the short way from my box to the theater lobby and out the doors. The snack bar area didn’t serve popcorn, but was set up to sell vibrators, dildos, beads, anything someone might need to enjoy themselves at a show in this particular venue.

The theater lobby opened onto the lower level of the castle’s main entrance. The checkerboard floor and hardwood contributed to the overall Clue atmosphere of the building. To the left, a corner led to a locker room. To the right, the entrance to the more hard-core of the castle’s dungeons.

“Anything with water sports, needle play, knife play, all of that happens in there,” I said, pointing to the doors. “If you’re interested in that, I would be happy to set you up with a suitable partner for it, but—”

“Now who didn’t do their assigned reading?” she mock scolded me with a cluck of her tongue. “I said no to all that stuff. No judgment. It just isn’t for me.”

“That’s exactly where I stand on things,” I said. “Though we’re one of the few resorts who allow any of that. So, people love to come here to meet up with like minds.”

“I like that about this place,” she said, running her hand along in the polished banister as we climbed the stairs to the upper lobby. “Nobody seems ashamed of anything. Am I going to have a hard time remembering to put clothes on when I go back to the real world?”

“You seemed to have difficulty with that before you came here,” I teased her.

The expansive upper lobby was paneled in the same dark wood as downstairs. Natural light streamed through diamond-patterned leaded glass in the windows high above. Like the theater, the lobby was completely empty.

“The castle opens every night at eight,” I explained, leading her toward the main-floor group dungeon. “It’s usually packed, though right now there aren’t as many people on the island as during the busy seasons.”

“I’m dying to know what the busy season is for a sex resort,” she remarked idly.

“The weekend of any religious holiday,” I answered confidently. People loved sin and blasphemy. I opened the door and clicked on the light switch, revealing the sprawling ballroom that ended in the tall glass bubbles of a half-conservatory. “This is a group BDSM dungeon. You can watch people, you can join in. Usual club rules apply, but don’t be surprised if someone offers you their sub to play with.”

Next, I showed her the strictly swingers room on the other side of the lobby. “No whips or chains here. Group sex on every surface.”

And there were plenty of them, in all kinds of shapes. Padded benches, wedges, bolsters, big square mattresses covered in washable faux-leather, even handles on the walls could assist in any number of positions.

I’d been in plenty of them, myself.

Next on the tour was the second floor, which housed the private rooms and the casino.

“The roulette wheel is my favorite,” I told her, almost giddy as I led her down the two plush carpeted steps onto the main floor.

She walked around the table to the padded bench beside the wheel and lifted one of the manacles. “I’m guessing the prize isn’t money?”

“Not the most important one,” I said with a slow shake of my head. “I want to strap you down there and let the lucky winners fuck you.”

She dipped her head, almost bashfully. “Like the dragon and the knights?”

“Exactly, princess. What do you say?”

She giggled. “Yeah. I think I’d be okay with that.”

Then, she shimmied her bikini bottoms down and hopped onto the seat. “Why don’t we practice?”

I drummed my fingers on the padded ledge of the betting area and cursed myself. “I didn’t bring a condom.”

“And there aren’t any here?” she asked, looking around the room doubtfully.

“There will be, tonight, when hospitality has been in to stock the place.” How could I have been so foolish as to think I could give Charlotte a tour of the resort and not get unbearably horny in the process?

She tilted her head. “You really didn’t do the reading.”

“Hmm?” I’d looked at her answers to the preliminary questionnaire. I couldn’t remember all those answers with the blood running from my brain to fill up my dick.

She spread her legs, the shawl skirt falling open around her splayed thighs,, and beckoned me closer. Closer. Until she could grab my T-shirt and pull me down to whisper in my ear, “I cleared all the requirements to go bareback down here.”

I lifted my head to look her in the eye, a shock jolting through me. “But last night—”

“If you hadn’t left me gagged, I could have reminded you.” She petted her vulva and bit her bottom lip. “So, are we going to—”

“Not here.” I picked up her bikini bottoms and handed them to her. “That’s going to be a little treat for later.”

She scowled in disappointment and put her bottoms back on.

“Let’s head over to the machine room,” I suggested. “You can see if there’s anything you’d like to try out.”

Who was I kidding? She would probably try out the whole damn room. She practically skipped there.

“Can I use stuff right now?” she wheedled as I unlocked the door with my master key. Most of the doors in the castle didn’t lock at all, but the toys inside this room were expensive to maintain and required knowledge of how they worked. I had that knowledge, but when the castle was open, staff members assisted guests in here.

“It would be a wasted trip if you didn’t,” I said, clicking on the light switch.

The way she gasped at the sight before her made my ego swell to alarming proportions. I liked to show off to people; it was a personality flaw I reluctantly accepted. With Charlotte, though, it seemed somehow more important. I wasn’t showing off my wealth, I was proving my worth.

“Okay, some of this is…” She wandered slowly into the room, which looked like a gym with much different equipment. Tonight, the mirrors on the walls would reflect a number of straining, sweating bodies, with mechanical sounds and screams of pleasure drowning out the music. Now, though, it was a large space full of industrial machinery.

“Is ‘intimidating’ the word you’re searching for?” I suggested.

She nodded, struck speechless. Which was out of character in the extreme for her. She trailed her fingertips along the gleaming metal arm of one machine. “What does this one do?”

Rather than describe it, I flipped the switch. The shining chrome rod slowly began to pump forward and back, and when it came up to a gentle speed, I twisted the dial all the way up. Her eyes widened as the arm jackhammered the empty air.

“Whatever dildo is being used goes on this end.” I pointed to the end of the driving shaft. “And there are plenty of options. There’s even a fist-shaped one, if you were so inclined.”

Her eyebrows were nearly to her hairline.

She moved on to another, a steel cage with a saddle atop it. “And this?”

“Strictly for the penis-havers, I’m afraid,” I explained, turning the other machine off and moving to her side. “See?”

She tilted her head to examine the hole at the raised front of the saddle. When in use, a disposable rubber sheath would attach to the built-in pump, while the optional thrusting mechanism allowed the user to be penetrated from the back. I took her hand and put her fingers in the hole then turned on the pump.

Her protracted, “Oh…” of understanding made me chuckle.

“So, have you used it?” she asked.

“Many times.” But usually in the privacy of my own accommodations. Which reminded me. “If you don’t feel like putting yourself on display, we can always have any of this brought to the house.”

She snorted. “Yeah, I’d hate to have anyone see me doing wild stuff like this. I’m shy.”

“Fair enough.”

Turning away from the machine, she pointed to the saddle-style vibrator in the corner. “Is that what I think it is?”

“It is.” That was the one that excited our guests the most, probably due to the overwhelming amount of porn that had bolstered the toy’s reputation. It was stunningly simple: a high-powered vibrator with optional attachments for rotating internal stimulation. As uncomplicated as it was, it yielded impressive results. Because the units themselves were so short, we’d elevated them slightly on platforms to keep our guests from having to kneel on the floor.

“Can I use this?” Charlotte’s eyes gleamed. “One tiny little orgasm? To tide me over until tonight?”

I grinned. “How could I refuse my princess?”

I flipped through my key ring and headed to the cabinet to get the attachments. We kept plenty, so they could be easily swapped out for sanitizing without putting the whole machine out of use for too long.

There tended to be a line.

“What do you think?” I asked, holding out a large option and a small one.

She grabbed the larger of the two. That’s my girl.

I got us a bottle of lube too, though she balked at that. “Trust me, I’m ready to go.”

“Trust me, there’s friction to think about,” I warned her. “With all of these machines. So don’t come in here expecting you won’t need some lubrication, or you’ll have a bad time.”

“Nobody wants rug burn on their pussy,” she conceded, untying her shawl and wiggling her bottoms down while I set up the machine.

With the well-lubed dildo jutting up from its cradle, Charlotte climbed on and sank down with a happy sigh. “Okay. I’m ready.”

I put the control box in her hands.

She frowned. “You’re not going to do this?”

I shook my head. “No. I’m going to watch.”

“And jack off?”

“No.” I was only human; I needed to be able to perform later. “I love to see you come. I love to listen to you. I’m going to do that now, with no distraction. And you’re going to be aware the entire time that you’re being watched.”

She shivered.

I sat on the edge of the platform beside hers and nodded to the controls in her hand. “Whenever you’re ready.”

She swallowed hard and switched it on.