I hope you enjoy my account of the siblings Jake and Kaylee, poured out in a week of heavy passionate keyboarding, especially for the
Summer Lovin' Story Contest 2023
.
Please comment and rate! xxx)
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"No!" I say to my father in disbelief, wide-eyed in surprise. But, what I mean is "Yes. Yes. Yes." I can hardly believe his words. A summer vacation in the Caribbean islands, fully paid! For a dirt-poor student like me, this is unreal.
"Yep." He replies smiling. "It will be the last one for our family, all together. Kay has already left home. Soon you will too. You have your own lives without us." Then, I see sadness in his eyes at those words, about the end of an era. Our family vacations are ending. He wants us all to enjoy one last time together, where he and Mom are taking their two kids away from home on a holiday.
Of course, Kaylee is not so much a kid, now 22. She has her own apartment in town and a new profession as a veterinary nurse.
I am going to be 19 soon and feeling pretty adult at last: tall and developing some muscle. My hair is dark brown and eyes are green. Not a bad combination all-in-all. Also, I guess it's worth admitting; I am a quiet and relaxed type.
I thought for a moment that the holiday would tie in with my birthday, but not quite, as Dad told me the dates we are leaving the week after. Because of our impending holiday, we agree to make my birthday a very low-key event.
We pick up Kaylee on the way to the airport. She is waiting at the entrance to her apartment block, alongside her luggage. Kaylee is tall, well-proportioned, with a nice figure, but not too slim or too curvy. Her flowing hair is cinnamon, a red-brown and her eyes are deep green. She is a classical beauty, Amazonian, in my naïve opinion. Her personality? Let's just say Kaylee is a force of nature.
Kaylee and I are sitting together on the long flight. It is a good time to catch up.
"I expected to see Daniel with you last week?" I have mixed feelings about her boyfriend. He is an OK guy, but good enough for her? Not so much.
"We have drifted apart." She admitted. "No fight or anything. Just we are going out less and less, probably for the last time."
The topic shifted to her work. I remark how she is a natural at the clinic, helping injured animals recover, for their owners.
"It's not that easy. Often, people find dogs and cats, suffering from being hit by a car, or attacked by another animal, sick, or abused by low-lifes. People want to help the poor thing, but not enough to pay. We can only operate as a business, but find some a place with a shelter. Others get put down. Our surgeons have to do amputations where a hospital for humans will repair the damaged limb. All because of the cost. It's hard sometimes. You have to learn to be detached from emotions."
I am enjoying reconnecting with Kaylee. We have always been good friends and rarely have petty fights, which I see often with siblings in other families. After a while our conversation dries up and we put on headphones for the plane entertainment system. As I relax to watch an inflight movie, I glance at her, just appreciating how well she has blossomed into a stunning, confident woman. Heck, Daniel is an idiot to drift away from her. Good riddance to such a dumbass!
Finally, we arrive at our destination airport. The island, which Dad selected, is colorful and tropical. I like the warm, exotic air. We are all excited on the shuttle ride to the resort, discussing the activities on offer to guests. The main hotel is about six levels, with well-kept grounds. Palm trees are everywhere. Check-in is fast. "Treadwell is the name." Dad says, and soon we reach our new home for the next ten days.
Our accommodation is not part of the main hotel complex. We are staying in one of a dozen little villas which were built in the 1980s for tourists, before they built a large hotel next door, about 20 years later. The advantage of a villa is having 3 bedrooms and more of a park-like setting. Except they are popular and expensive! Dad was lucky to get us one.
The villas are cute. Bungalows with a veranda, painted in bright pastels. Inside ours, the front door opens into a lounge with all rooms coming off it. A small bedroom is on the right, then the bathroom, then two more bedrooms at the back of the lounge, and a kitchenette in the corner. We are excited to be inside our holiday home. I get the smallest room with a narrow bed, but I don't care. I just need a place to crash. A golf cart brings our luggage to us, so we can unpack.
Later, Kaylee and I are exploring. We find one of the hotel's outside bars. Around us are people in the main pool, lounging, or going back and forwards to the beach. She is probing me on my girlfriends, a subject I was evasive about, while we were on the plane. Eventually, she gets to the truth.
"You mean that dick of yours hasn't wormed its way into a girl yet?"
"Kaylee!" I exclaim, then look around just to be sure no-one is listening. I only use her full name when I am most serious about something.
"Oh. Come on. Are my words making you blush? Well, we have ten days." I could almost hear the gears ticking in her mind as she decides. "We are going to get that checked-off before we leave. There are lots of pretty girls here." She becomes thoughtful. This is now her number one mission. My sister is going to get me laid, and that is part of the fun she wants from this family holiday.
Maybe it is her job as a vet nurse. She is automatically in control, and I am a patient. "I'm going to fix you up," she says, and then turns to face the sea, smirking. Appointment finished.
Gee. I am distracted after that. Dad and I check out the jet-ski rentals by the beachfront. Mom and Kaylee are off for some girl-time together in the resort, but it turns out they grab a taxi to the nearby town to see the shops.
Around dinner time the ladies return to the villa. While Mom and Dad are in the kitchenette, Kaylee touches my arm. "Hey, I bought something for you." In her hand is a pair of grey camo military-style shorts. "Put these on." I look at her, but her eyes tell me no back-chat. I go to my room and return wearing them. They are a little tight, but I can rock them, alright.
"Not bad at all." She surveys me, front and back. Better than your boring school-boy shorts. "If you're going to attract some horny girl. You need bait for the job. I'll get another pair like them. In the shop there's a dark green pair, which will do for a spare."
Next, she opens another bag and pulls out a pair of dark brown men's canvas outdoor sandals. My eyes bugged. They DID look cool. "Just what you need on a Caribbean beach. Not your usual boy's stuff." She shrugged her shoulder, and I thought about my trainers by the front door. "I checked your size. They should fit." I got into the sandals. They were comfy and smart. "Wow. Thanks, Kay. Thanks a lot!"
"We are not finished yet." In her hand is another small bag, but it is too small for clothing. She withdraws a thin leather cord with a catch, and on the cord is a long hand-carved bone fish-hook.
"I have never..." I start, but trail off, leaning my head forward. She places it over my neck. Suddenly, I am aware my face is inches from her pert breasts. Then she stands back again. "Let's see."
"Oh. Very nice. Now you look the part. Fun-loving beach-bum girl-magnet." She teases, "Maybe I should get your hair done next?" she mused, "A tousled look, with sun-bleached highlights, perhaps..."
I know she is dressing me how SHE thinks I should look. And I realize I can't stop her. All those years as her little brother, she always knowing better, have taken their toll. I am putty in her hands for a make-over.
At that moment, Mom comes out of the kitchenette and nearly drops the plate of nibbles she is carrying. "Kay got me some things." I say lamely. "Come on, I'm not that different."
Kaylee laughs hard and Mom smiles like it is a private joke. "He's on holiday in the Caribbean and needs to look the part."
Later, Mom and Kaylee are sharing a bottle of wine on the deck in front of the villa. They think I am out of earshot, but even while I am inside, I can just about detect their voices. They mention me.
"What's really with the changes to Jake?" Mom asks.
"Well. Our Jake is a shy boy. I get the impression he needs to brush up his style in meeting and talking to girls. I am not around very often. So, this is an opportunity to give him some womanly advice."
"Ah. Yes, I thought so. He's a good boy, but yeah, definitely needs some maturity in one or two areas."
"Yep." Kaylee smiled. 'Leave him to me and he will be a new man by the time we get home."
They laugh together.
The next day, it is late afternoon; I have to take a cool shower after the heat of the tropical sun. The water splashes and I feel my dick rise to attention, as it so often does in these moments. My thoughts are turning to the fairer sex. What can be more overpowering than the memory of letting my sister dress me as she wants? I breathe deeply, letting my soapy hand rub the smooth skin of my throbbing cock. I lean back against the shower wall, both hands stroking and rubbing, all the time thinking of an eager girl in bed with me. "Ohhhh." I moan under my breath as a sticky squirt arches into the air onto the tiles. I roll my foreskin down and up again and squeeze out the remaining drops.
"What is Kay doing to me?" I quietly ask myself. I went on this vacation thinking about sun, surf and sand, but now I'm thinking about sex, sex and sex. Now, I want the soft face of a girl and her cute body. Fuck, she had better help me find someone, or I will strangle her for this.
It is 10 pm, and Kaylee just ups and says, "Jake and I are going to the bar and we'll check out the nightlife." Adding for our parent's benefit "We won't be out that late." She hadn't flagged this to me, but she is brimming with confidence and I am becoming like a side-kick, following along. "Yeah. Should be good." I agreed.
We go into our rooms to get ready and I find myself putting on what Kaylee bought yesterday. She swings in and says, "You need a shirt at this time of night. I think you have one that's cool. That ocean blue one. Don't do up any of the buttons."
Kay is wearing an orange tank-top and white shorts, her midriff showing. Her white gladiator sandals are stunning. Dark eyeliner is all she needs to accentuate her features. Gosh. She is hot!
"Have fun," Mom and Dad tell us, as we wave and exit the villa.
The hotel bar is humming with activity. Lots of people, mostly couples of different ages, some singles and groups. The music is local. Don't know it, but it is easy to move to its beat. A few people are noticing us, and I quickly know that, together, we look good, damn good, if I say so myself. Kaylee is aware of it, too. We are both a decent height. I am 6 foot, she's two inches shorter, but easily makes that up with heels when she wants, which is the case tonight.
We get some drinks and move further over. A dance-floor is alive with swirling movement and colored lights. Kaylee looks at me. This is one interest of hers which I took part in, dancing lessons. We won some prizes at school. We are on holiday, rarely out together. She is hot. Will we dance? Yes!
If we looked good at the bar, we rocked that dance floor. It is so nice seeing Kaylee's moves again. I smile as an older couple clapped while we exited.
Back at a table, we are drinking and I see three girls nearby. There is tension, as two of them are into each other while the third is feeling very much a gooseberry. Just then, Kaylee's mission to get me laid enters my head with full force.
"She's pretty." I say, motioning towards the lonely blond girl. Cute and curvy, wearing a nice white, lacy frock.
"Hmm." Kaylee looks sideways and gets the girl's attention with some throwaway line. Soon, she is clearly pleased to be talking to someone else, other than her pre-occupied friends, and comes over to sit with us, bringing her drink. "Athena." She introduces herself. We do the same, and soon we are chatting about the hotel, its clientele and the island. She changes the conversation.
