A Vacation with my Sister – Part 1

A leading travel company offered me an irresistible deal for a luxury tour to the Maldives, for just a few thousands because they were trying to bring back tourists after Covid-19.

I wasn’t dating anyone at the moment, neither did I have any girls in my circle, so I called Callie, my elder sister and asked if she would be interested.

As expected, she wasn’t very keen to go on a vacation with her younger brother. Took a while to convince her, but I did it. Her boyfriend was going to the Netherlands for something work related around the same time, so she agreed to come with me. It was decided, Callie and I were going to the Maldives the following month.

I asked her to come over to my house a day before we left, since she lived in another city and it would be convenient to travel to the airport together. I contacted her occasionally that month, mostly to discuss regarding our finances for this tour and other travel documents.

The day finally arrived. I had applied all my leaves at work, packed up and was ready to go to sleep, since I had a long day planned for the next day with all the traveling. Callie was supposed to come home for dinner and stay over, but because of some delays she told me that she would directly be coming to the airport instead.

At this point my door bell rings. It’s Callie, dressed in a super hot, tight, black one-piece hugging her busty body. I always knew she was thick and good looking, but I’d never paid enough attention to her earlier, damn, my elder sister was fucking hot.

I could see that she was braless, and her nipples were pocking through her dress. The zipper on her dress was half open showing her cleavage and her busty boobs. Her bare meaty thighs were a sight to behold.

I greeted her and reached in for a hug, but she punched me and asked me to get her luggage in. I got her luggage in while she sat on the couch telling me how there was a change in plans and how she was able to reach earlier.

I went to the kitchen and made her some sandwiches for dinner. While she sat on my kitchen’s countertop and ate her sandwiches, I told her the plan for the next day.

Since I stayed in a single bedroom apartment, I offered to sleep on the couch and asked Callie to go sleep in my bed. She told me she didn’t mind if we both shared a bed, so we went to my room. Either way, we planned on sharing a bed while on vacation, so this shouldn’t have been a big deal.

So, we set our alarms for early the next morning, turned off the lights and went to bed. She kisses me a good night and closes her eyes.

An hour passes, Callie’s in deep sleep and I’m still wide awake. All I can think about are my sister’s busty boobs. Her large boobs were literally struggling to stay contained within her dress. Saying she looked hot in that dress, would be an understatement.

I couldn’t control much longer and wanted to touch her, so I slowly pull myself closer, put my arm around her waist and touch her navel. My cock is hard and is pressing against her sexy ass. At this point I’m pretty much spooning her.

I let my intrusive thoughts win, and move my hand to the zipper in her dress and bring it down. Now her boobs were no longer covered and her heavenly nipples, on her beautiful white boobs are right in front of my eyes. I knew she’d wake up if I touched her nipples, and didn’t want to risk it.

I then pull myself away from her, stroke my cock under the sheets and cum all over myself in just a few minutes.

I finally close my eyes and go to sleep. All I was dreaming about were Callie’s boobs, and my hands caressing them.

My alarm goes off, I wake up and find that Callie’s already in my shower. I close my eyes, and get back to sleeping hoping to get as much sleep as I could that day.

Callie comes out of the shower and wakes me up. She’s still in her bath robe and asks me to get ready quickly since we have to leave to the airport soon.

I quickly have my shower, dress myself up and go to my living room. Callie is ready too. She’s dressed in a beautiful white tank top with an exposed midriff. Yet again, she’s braless revealing her hot nipples.

I compliment her telling that she’s looking good, to which she replies “thanks, you too”. We then proceed to lock the doors and get into a cab.

At the airport, we finish our security check, check-in our luggage, and the staff at the counter informs us that we’re eligible for a free upgrade since the flight is quite empty. We gladly accept it.

We board the flight, I quickly rush and take the window seat, giving Callie the aisle seat. But she’s adamant and sits on my lap telling she wants the window seat. I grab her by her waist and try to lift her up, but she’s determined. She moves around and adjusts herself on my lap.

This triggered my cock and I get a boner. I didn’t want Callie to notice it, and make it awkward, so I get up from the seat and let her sit.

This was a long flight, and after a while we both were bored with the movies, so we get talking. One thing leads to another, we’re quite drunk and we decide to play truth or dare.

It was my turn first, and I chose dare. Callie dares me to call on any air hostess, and tell her that she’s gorgeous.

This was pretty simple, so I looked around and called the nearest air hostess to my seat. I asked her to get me some water, which she politely did. When she was about to leave, I told her, “hey thanks a lot, by the way you’re really pretty”. She just smiled and said, “aww, thank you”.

Next, it was Callie’s turn. She chose dare. I dared her to kiss anyone on the flight.

She gets up from her seat, walks around for a while, scouting for suitable men. Then she comes back to her seat, and tells “You know what, you’re my brother. Kissing you should be okay” and before I can respond, kisses me on my cheeks.

I then tell her that though this was cute, kissing on the cheek cannot be considered for the dare, and that she has to kiss someone on their lips.

“Fine then, who better than you”, she holds my face with both her hands and plants her lips on my lips, closing her eyes. After about five seconds, she moves away. It is at this point that she notices my boner and giggles.

“Looks like someone liked this”, she says pointing towards my boner. I told her that she was good looking, and that it was a natural manly reaction. “Alright then, let’s continue”, she said.

It was quite late now, we just had a few more hours before we arrived at the Maldives. The lights had been turned off and all the other passengers seemed like they were sleeping. We were extremely drunk so we decided it would be better if we slept too, before we did something we’d regret.

We turned off our lights, reclined our seats and covered ourselves with our blankets. Callie wanted some water, so bent and got the water bottle from the back pouch in the seat right before ours. While drinking, she dropped the water bottle on herself and her blanket.

Her top was all wet now, clearly revealing her nipples. Though there was nothing I could do, I just pretended to help by rubbing my hands over her breasts and nipples with a tissue, so as to dry her top.

She didn’t want to disturb the crew, so she asked me to share my blanket with her since we were about to land in a few hours anyway.

Both of us came closer, and covered ourselves with my blanket. She told me she was feeling cold, so I put my arm over her shoulder, very lightly touching her breasts. She kisses me on my cheek, wishing me a good night.

After a few minutes, it looked like she was sleeping, but I was wide awake thinking about her. I slowly moved my hand over her nipples, and cupped her breasts. God, they were amazing.

“Do you like it?”, Callie asked in a low, seductive voice while looking into my eyes. Before I could respond, she put her palm over mine, and made me squeeze her busty tits.

“You can have more of this later, but for now, just let me sleep in peace. We’re landing in a few hours, I’m feeling extremely sleepy and want some rest before we arrive”, she said resting her palm over my pants and touching my boner.

“You can continue playing with them, if it helps you sleep”.

Looks like I’ve taken a lot of your time already. If you’d like to read more about our sexcapades over the next few days of our vacation, do let me know and I’ll write more.

I’d really appreciate some feedback, good or bad. Thanks.

I've written this exact story on Medium available for free, which includes a few reference images (obv not actual). If you're interested, do check it out and follow me over here. I plan to write the next part over there by the end of this week.