Honeymoon with My Sister Pt. 01

Story Info
Dean vacations with his sister in her cheating ex's place.
6.5k words
4.59
49.3k
185
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Daymon1
Daymon1
162 Followers

It all started one unassuming day with an unexpected phone call.

"What's up, Mom?"

I could tell from the tone in her voice that she was having a rough day. "Dean, it's your sister. That loser fiancé of hers cheated on him. Only days before her wedding!"

My heart dropped. "Oh my god, is she doing okay?"

"What do you think? I've been on and off the phone with her all day trying to calm her down."

Let's rewind for a moment. My sister, Autumn, was engaged to get married to her tool of a fiancé, Mark, the next week.

Mark was Autumn's high school sweetheart and her first real relationship. He was a few years older than her and always acted like his shit didn't stink. The guy had a good job, a fancy car, and a nice house, but he was also an arrogant jerk who thought his looks and money could get him whatever he wanted. I always thought my sister could do better.

Autumn was nothing like Mark. She was kind, generous, and always put others before herself. She was intelligent and worked hard to make something of herself. She and I were close growing up, but once she started dating Mark I saw less and less of her. It wouldn't surprise me if that was his doing, being a controlling douchebag seemed to fit him to a T.

"Should I talk to her? Should I talk to him? Is the wedding still on? Mom, the wedding better not still be on-"

"Dean, I've done enough calming down of my children for one day. No, the wedding's off. Your sister is a mess, and nothing I've said has gotten through to her. Do you mind?"

"Of course, Mom. I'll call her right away."

"Thanks, sweetie. Let me know how it goes."

I immediately dialed Autumn's number, but stopped short of calling her. I was furious, and I knew the last thing she needed was me whipping her up into a frenzy.

Deep breaths, I thought to myself. Don't even mention Mark. Just ask how she is.

I dialed her number again and she picked up on the last ring. She didn't say anything.

"Autumn? It's me, Dean."

She sniffled. "Hey."

"How are you holding up, kiddo?"

"Not good." She sounded hoarse from crying.

"Want to talk about it?"

She burst into tears. "I just feel so stupid, Dean. I can't believe I didn't see any of this coming. Mark had been so controlling, isolating me from my family, just to pull the fucking rug out from under me. I'm such a fucking idiot."

I knew it, that asshole...

"Listen, don't you ever feel stupid for trusting someone. They're in the wrong, not you."

She sniffled. "It's like a week from the wedding. Everything's paid for, I don't even know what we can get refunds on. Dad spent all this money, but if I would have seen the truth earlier he wouldn't have wasted it on me."

"Aw, come on. You know he doesn't care about that. You know it's not you he's mad at. I'm sure we'll see him on the news tonight, arrested for killing Mark himself."

I heard something that sounded like a mix between a chuckle and a sob, which was something. Then she grew sad again.

"What about the honeymoon? I'm not getting a refund on that either."

"Just go yourself. Get your mind off of him. Go meet a tropical hunk a million times more handsome than him, maybe someone with an actual personality. I guarantee you that by the time you come back from Hawaii, you'll have forgotten all about him."

"I don't wanna be alone right now," she said, sniveling a bit.

"That's fine, bring a friend with you. It doesn't matter which two people go, right?"

She was quiet for a second and started crying again. "I don't even know who to take. I met all my friends through him, and I'm sure those assholes knew about this. I don't want to see any of them right now."

I didn't know what to say at this point. She sounded crushed, and I was struggling to find the right words to comfort her. "I'll go," I blurted out, without knowing where the idea came from.

"Huh?"

"Yeah, I'll go. Just you and me. We'll have a blast, finally catch up and hang out like we used to do."

"Dean, I can't ask you to do that."

I laughed. "What, you can't ask me to go on a week-long tropical resort trip with you? You're right, that's a lot to demand. Never mind."

This time she laughed too. "If I could hit you through the phone, I would."

"Yeah, well, the person who invents that is gonna be a billionaire."

"I'll pay them for it myself," she said, and I could hear the smile in her voice. "Okay, I guess we're going to Hawaii."

We chatted a little more, mostly talking shit about Mark and laughing at his stupid ass.

"Thanks, Dean," she said sincerely. "You're the only one who was able to really cheer me up."

"Anytime, kiddo. See you next week."

---

Time passed slowly over the next week as anticipation built for my upcoming vacation. One of the worst parts of vacationing is having to wait for it to finally come, so you would think that find out about it only a week ahead of time would make the wait a lot easier. That wasn't the case. I was particularly excited to spend some quality time with Autumn. I didn't realize how much I had missed her, and I was looking forward to catching up.

Finally, the day arrived, and I met Autumn at our parents' house so they could take us to the airport.

"Have a good time!" Our Mom called from the car.

"And no thinking about Mark!" Our dad added, receiving a (questionably) playful punch in the arm from Mom.

After waving them off, we took off toward the airport.

At this point, you're probably wondering what my relationship situation is like. "Dean, where's your girlfriend or wife in all of this?" I'm a good-enough-looking guy (I think), I take care of myself, I'm just always busy with work. My Mom calls it an excuse, and maybe she's right. Maybe it was just because I have a very clear idea of what I want and I hadn't met anyone who met my standards.

I say this so you hopefully understand why, when I saw my sister walking ahead of me wearing short jean shorts and a black, open-back shirt, her red hair cascading down her naturally tanned and freckled skin, partially obscuring the finely sculpted muscles she had been working on over the past year leading up to the wedding, that I couldn't help but look. She widened at the hips in a womanly way, and had just the right amount of cushion in her rear. Her long legs were lean and smooth, and she was wearing comfy sandals for the airplane that showed off an expensive, wedding-grade pedicure that she had already paid for and couldn't get refunded.

Okay, I had met one person who met my standards. Maybe Freud would go as far to say that she's the one who set those standards. (Did Freud even say anything about sisters?)

She turned around and my eyes darted up from her legs to her face, kind and beautiful, with striking green eyes and covered in freckles. "Are you coming?" She said, with a smile that could melt your heart (and did).

My mind couldn't help but turn the phrasing around on me and I could only mutter out a "huh?" as I caught up with her.

The flight was comfortable and uneventful. They had paid for first class tickets, and the luxury was nice on the long flight. Autumn slept the whole way, one of her jackets laid over her like a blanket, her head occasionally coming to rest on my shoulder. My stomach betrayed me, a funny fluttering feeling happening every time it occurred.

We were lucky enough to not have a layover, but still arrived at the resort pretty late in the afternoon. We headed for the check-in desk, where Autumn begrudgingly gave them Mark's name for the reservation.

"Oh yes, honeymoon package for Mr. and Mrs. Thompson? Congratulations, you two," the man behind the desk said with a smile.

"Oh no, we're not-" I started to say, but my sister cut me off.

"Thank you," she said with smile she was trying hard to make sincere.

The man raised an eyebrow, but if he thought anything more of it, he didn't say so.

A porter loaded our suitcases onto a golf cart and drove us out through the resort to our bungalow, pointing out different locations that were good to know as we passed them. The resort was massive, with dozens of bungalows spread out across the grounds. In the center of the resort was a couple different restaurants, a bar, and a pool with a hot tub. A private beach was a short walk away, and there were kayaks, paddle boards, and other water toys available for use. The resort also offered spa services and other relaxation amenities, and it was all included in the price.

When we reached our bungalow, the porter unlocked the door and carried our luggage inside. We tipped him and he thanked us, giving us another "congratulations."

The bungalow was amazing. The living area had a comfortable sofa and a fireplace, a large television, and a kitchenette stocked with wine and other adult beverages. There was a private deck outside overlooking the ocean, complete with a hot tub, lounge chairs, and a hammock.

Autumn walked up beside me, sighing. She looked as if she was about to cry.

"What's wrong?" I asked.

"This is supposed to be my honeymoon, with Mark." She choked back a sob. "I'm grateful you're here with me, but-"

"Hey, come here." I wrapped her in a tight embrace, stroking her hair and letting her cry into my chest. "I'm sorry, sis. I really am. But you deserve to have a good time. Don't let that jerk ruin this for you. Don't let him control how you feel anymore."

She sniffled, wiping her eyes. "I'm just gonna go to bed."

"Okay."

She disappeared into her room and I sat down on the sofa, staring out at the waves crashing against the shore. I was upset that Autumn was upset, and I couldn't help but feel like Mark was somehow watching us, enjoying the fact that he had hurt her this badly. I hoped he wouldn't get the satisfaction.

I grabbed a drink and sipped it slowly while Autumn got ready for bed. When she was done in the bathroom, I got ready myself. I walked through the bathroom to get there, and the one-two punch of the master suite hit me like a ton of bricks.

First was the master bedroom, which was huge, dominated by a king-sized bed in the center. Second was the bathroom, which was sleek and modern, with both a shower, walls lined all the way around with powerful-looking showerheads, and a jacuzzi-style bathtub.

Now it was my turn to be forlorn, as I suddenly wished that I had a partner to share it all with. The bed, the bath, the view... everything. It was almost overwhelming. However, I let the feeling pass, and I wasn't going to let this trip become about me.

"Hey," I said, passing back through the bedroom. "Can I grab some pillows from the bed?"

"Why?" She asked, confused.

"I'm gonna sleep on the couch."

She shook her head. "Please don't make me sleep alone tonight."

"It's just-"

"Dean, please." She looked vulnerable, and it melted my heart. "It's nothing we didn't do as kids."

I recalled those nights where she came to sleep with me when she had nightmares, when our parents were too cheap to book a bed for each of us on vacation, and when we stayed up too late playing video games and passed out next to each other. I smiled.

"Yeah, of course," I said. "I'll stay."

She slid over in the bed and I climbed in beside her. She was wearing an oversized t-shirt as a nightgown, and it wasn't clear what she was wearing underneath. I always sleep shirtless, and I already had it off as I made my way to the living room. I suddenly felt naked next to her, hoping I wasn't making her uncomfortable.

"Goodnight," I said from all the way across the bed. With how big it was, I might as well have been a million miles away.

"Hey, Dean?"

"Yeah?"

"Thanks. For coming with me. I'm sorry if this is weird or awkward."

"Don't worry about it," I said. "It's just like old times."

"Just like old times." I could hear the smile in her voice.

Except, it really wasn't. I was with my sister on her honeymoon, sharing a bed with her. She was a beautiful woman now, and I was man with desires, whether they were subconscious or not. It wasn't exactly the same at all.

I heard her breathing slow and deepen, and then it was just me. Me and the ocean, me and my thoughts. The night was cool and calm, and even though I was jetlagged, it didn't take long for me to drift off as well.

---

I woke up the next morning with a weight pressed up against me, and a head resting on my chest. A leg was slung over mine, and a hand was dangerously close to my crotch. My boxers suddenly felt tight, so I gently slid out from under her and padded to the bathroom, where I relieved myself dutifully.

"Not this time," I said to my penis, much in a way that a normal person wouldn't.

I walked out to find her awake, in the kitchen, brewing a pot of coffee. She was still wearing just the t-shirt, and it was riding up on her thighs, showing off a hint of her panties.

"Morning," I said, trying to avoid making eye contact with perfect, round little-

"Not this time," I reminded myself.

"Oh hey," she said, her tone disaffected.

"How are you feeling?" I poured myself a cup of coffee and joined her at the island.

"Ready for some fun in the sun?"

"I don't think I'm in the mood," she sighed. "I'm just gonna go lay out on the beach and read."

"Alright," I said, trying not to push her. "Let me know if you want company."

She smiled. "Thanks, Dean." She grabbed my shoulder and squeezed.

She finished her coffee and disappeared into the bathroom, reappearing a few minutes later wearing a black beach cover-up. She grabbed her book and a towel and headed toward the door.

"Have fun," I called after her.

She waved. "See ya."

I slipped on some swim trunks and a t-shirt, deciding to wander around and explore the resort. I checked out the pool first, where I had a drink at the poolside bar and watched the couples laugh and touch and kiss. I sighed. "None for me," I thought to myself.

I downed the rest of my drink and headed down to the beach. I wasn't going to have a good time just sulking the whole time, and neither would Autumn.

I found her lying out under an umbrella, her cover-up still on. She was reading intently, and didn't notice me approach.

"Hey," I said, plopping down in the chair next to her.

"Oh hey," she said, not really looking up from her book.

"Whatcha reading?"

"It's just a romance novel," she said, finally putting it down.

"Is that the best idea right now?"

She shrugged. "It's escapism."

I nodded. "I guess so."

We sat quietly for a while, Autumn reading as I people-watched. After a short while I got bored, so I decided to take action. I reached over and grabbed her book.

"What the hell?" She exclaimed, grabbing for it back.

"Enough escapism, it's time to actually escape."

"I hope that sounded better in your head," she teased, climbing over me to get the book from my outstretched hand. I wriggled away from her and ran down to the ocean, Autumn falling behind as her flip-flops dug into the sand.

I tossed her book into the ocean and she shrieked.

"Dean!" She shouted, lunging for me.

I grabbed her and pulled her into the water with me, both of us falling on top of each other, wrestling to get the upper hand. She pinned me down just as a wave hit, knocking her over and off of me.

Autumn stood up, soaked, and I couldn't tell what she was thinking.

"That was immature," she said, shaking her hair out.

"Well, it got you in the water, didn't it?"

She walked up to me slowly, wading through the waist-high saltwater. "Wait until I tell Mom," she said, pressing a finger to my chest.

I was actually scared for a second, not sure what she was gonna do, and then her serious expression broke. She started giggling maniacally. "Oh geez, you should have seen your face," she said, punching my arm playfully. "I can't believe I actually got you with that."

"No you didn't, not for a second."

"Yes I did. Dean, you're a grown-ass man and you're still afraid of your little sister telling on you?"

She splashed me, and before I knew it, we were in an all-out water war. After a while, we finally trudged back to our chairs, exhausted and soaked. Autumn stripped out of her soaked cover-up, revealing bikini underneath. It was a green, a color that always brought out her eyes and went well with her hair (though she looked like Christmas quite a bit of the time). It hugged her curves well, and it seemed a little smaller than she might have expected based on the spillage of her top out of the top of her top and her bottom out the bottom of her bottoms.

"Nice," I said, not really realizing how flirtatious it was until it left my mouth.

"You wish," she said, winking.

We went back to the bungalow and took turns showering, both of us changing before heading out to lunch.

"Congratulations on your marriage," the waiter said, as if there was a sign over us saying 'Hey, congratulate these two on getting married, we're totally not siblings.'

(Later I would realize that, every time we made a reservation, the system informed the staff member that we were newly married and cued them to congratulate us. Those tricky devils.)

I blushed and Autumn laughed.

"Is he alright?" The waiter asked her.

"He'll get used to it," she said, going along with it.

It felt strange, but not entirely uncomfortable. Something had clearly flipped in her, and I was happy to see her starting to have a good time. We chatted through lunch, catching up and staying for longer than we expected.

"What do you wanna do next?" She asked as we walked back to our bungalow.

"I should be asking you," I said. "It's your honeymoon."

"Don't remind me," she said dryly. "Let's go hang out at the pool."

The afternoon passed quickly, and we lounged in the sun. Autumn fell asleep, and I couldn't help but notice how peaceful and content she looked. As the sun started to set it got cooler, and Autumn shivered awake.

"Hey sleepyhead, wanna go grab dinner?" I asked.

"Sure," she said, stretching. "Let's go."

We ate at a hip sushi restaurant, and I felt like I wasn't cool enough to be there with Autumn. We first went back to the bungalow, where she changed into a tight black top and a pair of high-waisted shorts that showed off her toned figure. Her hair was messy and curly from the saltwater, and she looked effortlessly sexy.

"How did Mark not realize how lucky he was?" I mused, without thinking.

Autumn raised an eyebrow. "What do you mean?"

I stammered, trying to recover. "Just, um, you look nice tonight."

She grinned. "Dean, are you flirting with me?"

"What? No, that's not what I meant-"

She burst out laughing. "Calm your tits, dude. I'm messing with you."

I blushed. "Right, of course."

We ate expensive sushi rolls, drank sake, and Autumn even got me try a bit of octopus.

"Okay, now it's your turn," I said after gagging down a tentacle that felt like it was still squirming.

"What? No, that's gross."

"There's my sister," I said, rolling my eyes.

She smirked. "Fine, fine." She picked one up with her chopsticks and popped it in her mouth, chewing slowly.

"How is it?" I asked, ready to make fun of her.

She swallowed, and her eyes betrayed her words. "So good..."

We ate some more, drank some more, and then drank even more. When we went to leave the restaurant, the hostess stopped us and called a resort employee in a golf cart to shuttle us back to our bungalow. We giggled uncontrollably the whole way, leaning on each other for support. He made sure we managed to get the door open before he called out another fucking congratulations and drove off to pick up the next drunk couple.

Back inside the bungalow, Autumn kicked off her shoes and collapsed on the couch.

"I'm so drunk," she said, her eyes closed.

"Me too," I agreed.

She groaned, sitting up. "I need to shower. My hair feels weird."

Daymon1
Daymon1
162 Followers
12