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Four

Author: Jiji
last update publish date: 2026-02-24 14:34:36

Matthew

Who the fuck is this woman?

I could barely remember how to use the key card when we reached the door to the presidential suite. Which I now had to rename. It would probably up honeymoon bookings; nobody wanted to think of Woodrow Wilson on the most romantic trip of their lives.

The more immediate issue was that my best friend’s little sister was brutally hot and incredibly fun, and she was about to be in my hotel room.

The lights came on automatically when I opened the door, and Charlotte nodded with a grudging smile. “That’s pretty impressive.”

“Wait until you see the rest of the place.” I couldn’t keep my eyes off her as she walked in. “Hourglass figure” didn’t come close to describing what was going on under her tiny shorts and distractingly thin tank top.

The air-conditioning in the building enhanced the look.

And she was Scott’s sister. Regardless of Scott’s insistence that he was only worried for my fragile emotional state—which wasn’t the glass castle of pain he envisioned—I had a strong suspicion that he was attempting to protect Charlotte’s virtue. Which sounded like a full-time job.

Sure, it was presumptuous to think that Charlotte would have sex with me. But Scott seemed damn sure it was a possibility.

And within minutes of meeting her, I wanted it to be a possibility. I’d never experienced such an instant, electric attraction to anyone.

She tossed her ponytail and gestured over her shoulder at the great room. “This looks a lot like our villa. But we have private verandas.”

“Private balconies,” I countered.

“With soaking tubs?”

“Just one.” I pretended to concede to the luxury of her accommodations and let her be smug for a second before I hit her with, “And a shabby little rooftop pool.”

Her eyes widened.

“You wanna see it?” I offered.

“I kind of have to at this point.”

I led her past the kitchen to the spiral staircase up to the roof. A short landing hid the utility door—which I hated and had already put in an order to replace with something still up to fire and security code but less industrial—that opened onto the rooftop terrace. From certain vantage points, one could see the entire resort; thanks to artfully placed hedges and railings, the rest of the resort couldn’t see us. A small café-style table and chairs were grouped near the pool, with more seating in the form of sturdy but luxurious outdoor sofas and armchairs arranged beneath a permanent canopy. 

I went to the wet bar there and grabbed my stuff, and she followed me, plopping down on a love seat and kicking her sandals off before dropping her feet on the big square table. 

“Okay, you win,” she said, toying with the end of her ponytail. “There are advantages to the presidential suite.” 

“Thank you for conceding the win.” I took the armchair closest to her. Not sitting right next to her, but not so far from her I couldn’t pass a joint. Safe, respectable, not-creeping-on-my-best-friend’s-little-sister distance. 

“It won’t happen often. I’m very stubborn,” she informed me, fully unapologetic. “And I’m being nice and not pointing out that the private villas have direct access to the ocean.” 

“Pools don’t have sharks,” I immediately countered. 

“Is that really a plus, though?” she mused, squinting her luminous blue eyes slightly. “Sharks are cool.”

I couldn’t argue with that. “I actually swam with sharks once,” I said as I set about rolling up our joint. “In the Bahamas.” 

“At another one of your resorts?” she asked.

“That time? No. But I was in town to check out someone else’s resort.” My completely one-sided rivalry with Glynn properties had driven me to visit several of their resorts around the world. The Nassau one had nearly made me weep with envy. 

“So, you go around and scope out the competition?” She asked suspiciously. 

“It’s not that weird.” It was probably very weird. It’s not like I had a ton of fellow resort-chain-owning friends I could compare behaviors with. “And it would be chintzy of me to only take vacations at my resorts because they’re free to me.” 

With one notable exception that I wouldn’t discuss with her at the moment. Ascend properties were the destination swinger resorts and kink clubs worldwide. I needed to pay a visit to one, badly, and soon. But I hadn’t invited her up to my room to talk about kinky stuff. In fact, I was pretty sure Scott would kick my ass if I told her about the place. 

Unless she already knew about them, which seemed like a distinct possibility, if the cruise story hadn’t been exaggerated. 

“I would honestly live at a place like this. I know people do that all the time.” She motioned around us. “Live in hotels.”

“I’ve heard similar. But it seems like they do that… mostly in big cities…” I tried to split my concentration between the task in my hands and the task in my mind, and my hands were winning out.

“Tell me about the sharks.” She whipped from topic to topic at a speed I had a difficult time keeping up with now. What the hell would happen when I was stoned?

Since she’d offered me the chance to brag, though, I would take it. “Well, I was very brave, obviously. It was a guided scuba tour where they drop this big chunk of bait and you go and dive down and let them circle you. Watch them eat. Hope they don’t eat you.” I paused before wetting the glue strip on the paper. “I’m sorry I’m going to put my tongue on this.”

“Billionaires don’t have special moistening apparatus for cannabis cigarettes?” She affected a snooty accent as she said it, then dropped it, laughing. “It’s okay. The fire will burn up whatever awful pathogens are in your saliva. Continue with the sharks.”

“There isn’t much else to say.” I racked my brain. “The water was nice.”

“What kind of sharks were there?” she asked, leaning forward like a journalist who’s gotten an interview subject to open up. “Tiger sharks? Great white? Those ones who look worried all the time?”

“You’ll have to forgive me, but I don’t remember. It was enough that they were sharks. I didn’t need to know the species of every single one of them.” But I wished I’d paid attention, now. Apparently, trivia was a great way to impress her.

Trivia, and not a fucking awesome hotel suite. On a resort that I personally owned.

I handed her the joint and pushed a lighter across the corner of the table. “Ladies first.”

“Okay, but I’m not a lady,” she warned, lighting up.

“Your brother mentioned that.” Maybe she wouldn’t want to know that her brother had mentioned it. I wouldn’t want my sister to talk about my sex life to everyone she knew.

“I’m sure he did. I’m sure he warned you all about me,” she said, her voice tight as she held in her inhale. She passed the joint to me and exhaled. “And my body count.”

“He did warn me that you were a heartbreaker.”

She scoffed. “That’s not fair. I rarely have serious relationships. I’m not out there breaking anybody’s heart.”

That, I couldn’t believe. Because serious relationship or not, if I had a woman like Charlotte for even a week, I’d mope about losing her.

That’s exactly what Scott was talking about, dummy.

“Well, I’m not going to be the first,” I joked, taking a hit.

“Good. As long as we’re on the same page about that.” We made another pass and she paused before inhaling. “But I do want to swim in your pool.”

“Should have brought your suit.” I would have loved to see that.

“I don’t need a suit.” She exhaled a cloud of smoke. “It’s a private pool. Who’s going to see me?”

“A security guard?” There wouldn’t be any security guards up here, and I didn’t allow the cameras to be turned on while I was staying.

She shrugged. “Oh well. I know the owner and he’s not going to kick me out.”

My high began to overtake my horniness and inject some common sense into my screaming brain. “Yeah, but if I let you get naked up here, then I have to go confess to your brother, and the friend code says he gets to punch me in the face. I don’t want to have a black eye in the wedding pictures.”

“Maybe the wedding pictures will defer the punch,” she suggested. “But if you don’t want me to swim in your pool, I won’t. Like I said, I’ve got the whole ocean out there.”

“Full of sharks.”

“That wouldn’t have a problem with me being naked.”

“I never said I’d have a problem with it.”

The silence that fell between us was like a dare.

One of us had to make some kind of move to steer us in the right direction. Maybe not the right direction. More like one of two inevitable directions. One ended with me walking her back to her villa after a fun, flirty night that never went any further.

The other…

She took another hit and stood up. And then she pulled her top over her head.

I knew it was rude to stare. But her breasts were perfect. It would be like looking away from a staggering work of art or a breathtaking natural vista. I gripped the arm of the chair to stop myself from reaching out to touch her creamy skin, which I could tell would be impossibly soft from looking at it.

She reached for the button on her cutoffs and nodded toward the still-burning joint in my hand. “That’s not incense, you know.”

“Sorry.” Why was I apologizing? I was wasting my own weed. I drew in a big hit and prayed the THC racing to my brain would make me completely disinterested in sex or anything related to it.

At the very least, I hoped it would help my raging erection go away.

Then she leaned down and parted her pretty pink lips, craning her head toward the joint in my hand. I lifted it and she took a long drag, then stepped back and shimmied her shorts down her hips.

No underwear.

Jesus Christ.

“Come on,” she said, dropping her clothes on the love seat as she walked away. “Or are you going to go in and get your trunks?”

Was it impolite to tell someone that you couldn’t possibly get into a pool with them, naked or otherwise, because your dick would be too obviously hard?

That said, she had to know that was the case. It might have been her intent all along.

My gaze moved from her gorgeous ass up the curve of her lower back, vividly imagining my hands there, holding her in place as I stroked into her again and again.

You’re going to fuck your best friend’s sister tonight, my brain warned me. This has already gone too far. The second your pants come off—

She dove into the water and came up laughing. “You’re lying about the shark thing. You’re too afraid to get into a swimming pool with me, so you’re definitely too afraid to get into an ocean with sharks.”

“Sharks aren’t trying to fuck me,” I blurted.

Her mouth dropped open with shock. I almost apologized. Then, she shrugged and said, “That’s true. I am.”

I got up and tried to subtly adjust myself as I walked to the pool’s edge. She swam up and folded her arms on the ledge. Water droplets clung to her skin and dripped from her long eyelashes and the tip of her nose. I put my hands in my pockets and looked down at her. “We just met.”

“Yes, we did.”

“I’m your brother’s best man.”

“That is true.” She blinked up at me expectantly, and my resolve crumbled.

I tossed my hat aside and pulled my T-shirt over my head. “We have to keep this a secret.”

“I was never going to tell him about this, anyway,” she said, pushing back from the wall. “I’m a grown-up. You’re a grown-up. Scott doesn’t own either of us. And you’re fucking hot.”

“Thanks. I’ve been working out.” I dropped my shorts and she half-gasped, half-laughed.

I was used to that reaction.

“Wow. Congratulations on all of that,” she giggled, gesturing to my dick.

“Thanks.” I grinned and busted out the most disgusting reply I could think of. “My mom made it for me.”

It had the intended effect. She groaned, “Ugh, gross,” but laughed anyway.

She kicked toward the center of the small pool and treaded water there while I jumped in. It wasn’t a dramatic jump, as the deepest the water got was only five feet.

“You’re not one of those guys who thinks because he has a bigger-than-average dick, he doesn’t have to try in bed, are you?” she asked as I swam to join her.

“You’re not one of those women who thinks because she’s hot, she doesn’t have to try in bed, are you?” I shot back.

“Fair. I guess we can grade each other at the end.”

I reached her side and sank down to her level; five feet wasn’t deep on my six-foot-three frame, but if she put her feet down, her nose would probably be underwater. I pulled her into my arms and she gazed up at me, her big doe eyes instantly captivating me. For a second, I wouldn’t have been able to describe my surroundings. Her firm body and soft skin seemed to melt against me. There was no shyness or rigidity to her, no reservation.

I’d been with countless people like her. People who knew they liked sex and wanted to have a good time, the kind of good time that was perfect for getting over a breakup.

I would have to show her a good time, then.

But there were preliminaries. “I’m not trying to be crude here,” I began, “but from what I understand, you’re ‘free-spirited.’” I made air quotes with one hand. “I need to know if you’re safely free-spirited or…”

“Reckless?” she finished for me. “I’m very careful. I’ve never had sex without a condom before. Except, you know. Oral.”

“Do you get tested, then? If you’re not using condoms and dental dams during oral?” It sounded like a doctor’s office question, but safety first.

She nodded. “Sure do. Every three months if I’m out there and active. I know everyone thinks my life is this nonstop fuckfest because I show the slightest interest in sex and one-night stands, but I haven’t gotten any since that damn cruise last year. I passed the last exam with flying colors. How about you?”

“Regular checks, just got out of a long-term relationship.” I didn’t mention that those “regular checks” were a requirement for membership at my kink resort. Even the most free-spirited of free spirits were sometimes put off by the mention of anything harder than handcuffs. This would be a straightforward, well, fuckfest, to use her words. “I use condoms during intercourse, that’s nonnegotiable.”

“Same.” She held out her hand for a businesslike shake, and as I took it, she added, “But if it’s okay with you, I like to swallow.”

Jesus. What had I gotten myself into?

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  • In love with my brother's best friend    Twelve

    Charlotte's POVI literally could not stop replaying the scene from Matthew's room in my head.No matter how hard I tried to focus on getting my makeup done or helping with the wedding dress, my mind just kept looping back to that exact moment.More than anything, the words my brother had shouted kept ringing in my ears. He said Matthew was going to treat me like the others. Like the rest of his past fiances.Those words bothered me a lot. Like, a normal amount of brotherly worry is fine, but the way Scott said it made it sound like I was just another name on a very long list. It made my stomach twist into knots.Sitting in the bridal suite, listening to everyone laugh and drink champagne, I felt like I was making a grave mistake of some sort. Like I was blindly walking right into a trap that everyone else could see but me.But honestly?

  • In love with my brother's best friend    Eleven

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  • In love with my brother's best friend    Ten

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  • In love with my brother's best friend    Nine

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  • In love with my brother's best friend    Eight

    Charlotte The morning came with more noise than the day before.I could hear voices in the corridor before I had fully woken up, someone laughing, a door closing, the particular kind of energy that moves through a building when everyone inside it is preparing for something. I lay still for a moment and let the sounds settle around me, and then I remembered what day it was and got up.Scott's wedding was tomorrow. Today was the last full day before everything changed, and the resort knew it. By the time I came downstairs, the lobby had already shifted into a different register, louder and warmer, with clusters of people gathered near the entrance and a steady movement of new arrivals coming through the doors with overnight bags and bright expressions. I recognised some faces from photographs Scott had shown me over the years and others I had never seen before, and all of them carried the same easy excitement that comes with being somewhere celebratory with people you are glad to see.

  • In love with my brother's best friend    Seven

    Charlotte The sunlight came through the curtains before I was ready for it.I lay still for a moment, staring at the ceiling, listening to the quiet of the room and letting my mind catch up with the rest of me. The sheets were soft and the pillow still carried the faint warmth of the night before, and for exactly three seconds I felt completely at ease, the way you only do when you are half-awake and the world has not yet had a chance to remind you of anything important.Then it did.I turned my head slowly to the other side of the bed and found it empty, the indent still there in the pillow, the duvet pulled slightly to that side. Matthew was gone, which was both a relief and something else I did not have a name for yet. I sat up carefully, pulling the sheet around me, and looked at the room in the early morning light. Everything was exactly as it should be. Nothing had been broken or overturned. The world had continued to exist in its usual arrangement and yet something felt fun

  • In love with my brother's best friend    Chapter Six

    MatthewThe bottle left her lips with a soft, wet pop. A single drop of water clung to her bottom lip before it slid down, tracing a glistening path over her chin, down the elegant line of her throat, and straight between those perfect tits. I watched it disappear into the valley between them like

  • In love with my brother's best friend    Five

    CharlotteThere I was, fully naked in the arms of the hottest guy I’d ever seen, and he was adorably shocked by my request to suck him off.“Oh, that’s what strikes you speechless,” I teased him. “Not me stripping naked less than an hour after we met?”“I—”I slipped my arm around his neck and pull

  • In love with my brother's best friend    Three

    CharlottteThe resort was absolutely ridiculous. There was no other way to describe it. We pulled through the tall wrought iron gates at midnight, and everything inside the stucco perimeter fence was hopping.“I thought this was a quiet seaside vacation spot,” Mom said nervously as she peered out t

  • In love with my brother's best friend    Two

    MatthewIt wasn’t every day that I got a chance to surprise my best friend, especially since our jobs had basically kept us in different countries ever since college. We’d gotten together every chance we could, but for the past decade it had been a once-per-year affair. And now that he was about to

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