Last winter I happened into a depressed state. I was busting my balls at work, taking on jobs that were far outside my duties. The weather didn't help any, in fact it made it worse. It got dark early, it was always cold and the snowfall had been unusually merciless that year. I was bitching to my sister about all of this one day over coffee when she made me an offer I couldn't refuse.
"Peter, take a look at this. "she said, while pulling a brochure out of her bag. It was an advertisement for one of those package holidays in the Caribbean. It offered one week of fun in the sun for a single, set price.
"This is nice, "I said, throwing the brochure on the table. "but these deals are for two people. I've got no one to go with. "
My sister, Emily, picked up the packet and shoved it back at me. "Well, I've got vacation time lined up; I'll go with you. "
Like I said, I just couldn't refuse. I too had vacation time; actually I had it in excessive amounts. And nothing seemed a better cure for my blues than a week on a warm island surrounding by beautiful blue water. So, my sister arranged the whole thing and fifteen days later our plane touched down in Jamaica.
I was a little weary at first: our hotel's airport shuttle was this rusted out van driven by a man that must have had too much to drink. But after braving a dangerous car ride down narrow Jamaican roads, I was pleasantly surprised by our hotel. The Gilligan Resort and Inn was located on it's own secluded beach. It had a giant pool, filled with clear blue water, it's own nightclub and several decent bars for us to enjoy. Our package required Emily and I to share a room but boy were we happy with our accommodations. Our room was actually a huge suite with a private balcony view of the sea and a bedroom each, for my sister and me. The bathroom was a hotel room unto itself: it featured a shower that could double as a sauna and nice, if not cozy, hot tub.
Emily couldn't wait to hit the water and as soon as she got settled, threw together a beach bag and headed out the door.
"See-ya bro!" She said, walking out of our suite. I decided I wanted to enjoy our room for bit so I ordered up a Banana Daiquiri, changed into shorts and a tee-shirt and kicked up my feet on the balcony.
We had quite a nice view of the water and beach below. After sunning myself for a while, I stood up and surveyed the scene. The sand was teeming with all kinds of people, half-naked and having a good time. I couldn't help but notice all the beautiful women in slick one piece swimming suits and revealing bikinis. Deciding I wanted to get a better look, I threw on my swimming trunks, grabbed a towel and headed to beach.
I searched among the vacationers for an eternity and just when I was about to give up, I recognized my sister's bag. Emily was sunbathing face down and barely acknowledged my arrival. But honestly, I couldn't help but notice her.
It may be wrong to check out your sister but with her face covered, she'll look like your average sexy woman catching sun on the beach. Her skin had already begun to turn brown and on top of that, Emily had applied generous amounts of oil making her appear good enough to eat. I really couldn't take my eyes off of her ass: it was huge, round and it's flesh was nicely offset by the clingy white material of her bathing suit.
"Jesus Christ, man. "I said while thinking impure thoughts about my own sister.
Emily stirred a bit. "What's that? "
I turned away from her quickly. "Ah, nothing. It's the beach… it looks nice. "
"You should go into the water; it's nice and cool. "she answered. Believing that it was a good moment for some cold water, I took Emily's advice.
After that embarrassing, if not guilty, incident, the vacation went smoothly. My sister and I both developed unhealthy tans, explored the island, got some shopping done and took a nice little snorkeling adventure.
On the third night, we decided to try out our hotel's club. The Rumba Room, as it was called, was pleasant enough with a live DJ spinning a mix of club and Caribbean music. I danced a little with Emily but after a time, decided to give it a rest and take to the bar. I soon lost track of my sister but happened upon a gorgeous British woman who seemed to like me buying her drinks. We talked for a while, laughed, exchanged some flirtatious dialogue and generally had a good time. However, Lady Luck wasn't with me and the Brit eventually bid me goodnight. I looked around for Emily, couldn't find her and retired to our room.
To offset the feeling of rejection, I grabbed an overpriced bottle of champagne from the fridge, filled up the hot tub and tired to soak my worries away. Thoughts of what could have happened with the woman at the bar filled my head and I started to stroke my cock under the water. But I wasn't to get very far: I heard the door unlock.
"Emily? "I called.
"Yea, it's me. Where are you? "
"In hear! "I answered.
She popped her head around the door. "What are you doing? "
"Ahhhh, just relaxing. "
She opened the door a bit more. "What happened to that redhead you were talking to? She was cute! "
I sank into the tub. "Aw, she had to catch a plane home, I guess. "
