A tropical island

K-T was ecstatic. Somehow his family had won a contest from some TV show. The kind where people call to answer stupid questions during ad breaks on ridiculously overpriced phone line, only for one of the thousands of people who gave the right answer to be picked out and get a prize.

And what a prize... Even with the scammy nature of such games trying to get millions of people to call, K-T couldn't believe that it could be profitable for the first prize to be a two week all expenses paid trip for 8 people in a high end hotel on some dreamlike tropical island in the Caribbean.

Of course his two parents would come and his twin sister Emily would too. He was less delighted by the presence of his aunt Jill, she was often involved in events that ended up leaving him wearing a lot less than he would have liked.

Once the 5 people of his family had been picked the remaining three slots had been heavily debated. Emily wanted to bring a friend with her and after complaining that she couldn't really choose between her two best friends Lucy and Jennifer without losing the friendship of the other, she had been allowed to bring both of them.

Aunt Jill had tried to get one of her own friends to come with but K-T had been really opposed to it. He know this woman in particular and she had the same tendency than his aunt of trying to humiliate him, except it was turned to 11. The last time he met her while having to stay at Jill's place for a week she had managed to convince his aunt (and it hadn't been a tough sell. At all) that the 18 year old boy need to wear a diaper and be in bed by 6pm. Big no on her.

K-T school life of constant humiliation had put people in three categories in relation to him. The ones that thought he was enjoying it all and him to be a pervert and as so avoided him. The ones that completely ignored him. And the ones who happy to have found an easy target spent their time bullying him. The girls mostly for the thrill they got out of humiliating a boy in front of the whole school. The boy mainly for two different reasons: some really jealous thathe was so endowed down there and had been so soon during puberty. Other to punish him for showing off his cock to their girlfriends (despite the fact that he never did so by choice and that their formof bullying involved him doing it even more often.).

This left him with very few friends he could invite for such a trip. He also had to consider that this would be his first real vacations as an adult and that a luxurious trip like this could be a good way to woo a girl. Of the two girls he had a crush on, Samantha wouldn't fit at all, she was very rich, so much that she could have paid for the whole trip for everyone on her own dime without issue. Inviting her would do very little to impress her and it was really doubtful that she would have even accepted in the first place.

The second girl had been a perfect match. Lily was the little niece of the old couple living across the street. She was spending a lot of time at their place because her parents traveled a lot for work and along the years K-T had completely fallen for the lean and athletic blonde. He had to argue with talent and put his foot down, preventing Jill from taking her crazy friend or Emily to get to bring a third of hers. And in the end he won, doubly.

Not only did he manage to convince his family to let him invite her, but when he went to ask her she immediately accepted, touched and delighted by his generosity towards her. In a spark of the moment she even hugged him and left a quick kiss on his cheek. That night K-T had barely slept and just thinking about what could happen had made him so exited that his member was raw in the morning from beating off so much. Him and his dream girl, two weeks together in a beautiful hotel, white sand beach, tiny bikinis...

Now it was time to leave. He had packed his suitcase with enough clothes for the trip, which with how little he owned and his propensity to lose them was pretty much everything he owned except for a few winter clothes that had been put in storage and would barely fit him after his last growth spurt. He had his backpack with his tablet, headphones, phone, a few books and snacks for the trip and everything else had been put in his suitcase.

This needed to be a perfect trip. He made sure to finish packing the day before. Leaving no chance to fate that his suitcase wouldn't be ready and left behind, it had been ready next to the door since the evening. He got up and got clothed more than three hours before the shuttle that would bring them to the airport was supposed to arrive. Making sure to already have showered and used the toilets long before then. He knew that any event where he had to remove any clothing was yet an occasion for his mother, aunt or even sister to drag him out half dressed by saying that he was late.

It was sad that it was a special occasion but he was wearing a full outfit. A colorful floral pattern Hawaiian shirt, underwear (a very rare perfect normal nearly new pair of boxers that actually fit him), cargo shorts, a pair of socks, some sneakers, a baseball cap and a pair of sunglasses.

Nothing, absolutely nothing could ruin these vacations for him.