A Roll of the Dice

Author's Note: This story has been written exclusively for Literotica's "Summer Lovin' Story Contest 2010" writing competition. Thanks in advance for your votes and/or comments (but especially the votes, the higher the better, lol). I have tried my best to write this story in keeping with the spirit of the theme. Vote with your heart.

Description: On a Greek summer vacation, a woman finds herself torn between two men.

*

Todd sat across a small, round table from his sister, Sabrina. The two were enjoying a summer vacation in Greece on their father's dime. He couldn't keep himself from frequently staring. His sister had gone from being a kid to a tantalizing beauty seemingly overnight.

Between them both, on the table, rested a cup containing two dice. It was his decision... his roll...

* * * * *

Sabrina, who was a fresh, nineteen year-old high school graduate, had asked for this trip as a graduation present. She'd wanted to come alone, but her father immediately denied that request and told her he'd act as chaperone. When business interfered with their plans she was excited by the prospect that she might get her way after all. Instead, her father asked her older brother, Todd, to fill in.

She argued the point until she was blue in the face that she was of legal age and could do this alone, but her father remained adamant. In the end, faced with the possibility of the entire trip being canceled, Sabrina reluctantly agreed.

Todd, being much older at twenty-six, lived in a different part of the country and the two hadn't even seen each other for several years. Due to the age difference they'd matured at different times, leaving them emotionally distant. Simply put, they just didn't know each other very well, and shared no common interests.

Being much younger than their father, Sabrina was hoping Todd would be cool about things and not be overly protective. The last thing she wanted once she got to Greece was to have someone constantly shadowing her. She was desperate for some summer fun, maybe even a brief summer romance, before beginning college.

A week after her graduation she flew to Chicago where she met up with Todd at the airport. After sharing an uncomfortable hug they walked to the international terminal and waited for their flight to begin boarding.

He was stunned by how mature she looked, and how incredibly gorgeous his kid sister, now a young woman, had turned into. It was almost as if he was looking at someone else, except for the shoulder-length auburn hair and brown eyes he was familiar with. If not for the digital photos their father had shared with him, he might not have even been able to recognize her, so complete had the transition been.

Todd couldn't help but gawk in wide-eyed awe. Her slender, shapely frame was dressed in what appeared to be a scandalously short white skirt, which showed off her nicely toned legs. Once he was able to pull his gaze away from them, he next took notice of the thin, pale blue halter that was held in place by spaghetti-sized shoulder straps. Watching her breasts mildly shifting under the clothing captured his full attention.

"Hi Todd," she greeted him, leaning forward for a brief, uncomfortable hug.

"Sabrina, you look fantastic," Todd complimented her appearance. "You're no kid anymore."

They sat down together and made brief attempts at a polite conversation, but they dead-ended in an uneasy silence. To fill in the time and minimize the awkwardness they each turned to their smart phones. Sabrina texted a few of her girlfriends as Todd made a couple of calls to clients.

Once on the plane the pleasant distractions provided by the phones were no longer possible. She was assigned to a window seat on the left side of the aircraft just over the wing, while Todd was beside her in the middle. An old woman had taken the aisle seat.

After taking off and reaching cruising altitude, Sabrina removed her seatbelt and leaned toward the window, making an effort to sleep. In reality she was still upset about not being allowed to travel alone and she was holding this grudge against Todd, despite the fact that he was actually doing her a favor.

As Todd sat beside his sister he couldn't help but sense that she was giving him a cold shoulder. He was aware of the trip's history, their father warning Todd to keep a close eye on her after her emotional meltdown and temper tantrum when she was denied permission to make the trip alone.

Just to prove his point and put a little fear in her, their father made sure he sat her down the previous night to watch a movie about the terrible things that can happen to attractive young women traveling abroad, and how he wasn't an action star who could travel across the globe and rescue her in the nick of time. According to what Todd had been told, their father thought she'd gotten the message... but had she?

I don't handle women very well, he thought to himself. I'm too kind when I need to be forceful, and too stern when I should be lenient. I'll never figure them out.

After an hour of boredom he scooted past the woman in the aisle seat and fetched his tablet-sized computer for something to do. As he began looking at some family video clips and Sabrina heard the sound, her interest was piqued.

"I can't sleep," she complained in a frustrated tone as she returned to an upright sitting position. Leaning over his lap she asked, "What are you watching?"

"Some old family movies," he answered. "You're welcome to look at them with me if you'd like."

The two siblings, once awkward around each other, quickly became like two peas in a pod. He placed the computer on the one armrest they shared as he used finger-taps and other motions to scroll, launch, and resize the display.

"This one is when you were five," he explained. "You have got to see mom's Christmas-morning hairstyle, it's hilarious!"

They both laughed at their mother, who was definitely not a morning person, as she staggered into the living room half-asleep, hair in total disarray. Several times, as they laughed, they looked up into one another's eyes and shared a deep gaze. Sabrina felt a chill passing through her spine every time they connected this way, not knowing that her older brother was experiencing a giddy sensation like he had when he first fell in love.

"Can I get you anything?" a flight attendant asked.

"I'll take a rum and cola," Sabrina spoke up.

"I'll have to see an ID. The legal drinking age in-flight is twenty-one."

"Sure, not a problem," she answered as she reached for her purse and produced the necessary identification.

Satisfied, the drink was provided.

For Todd it was as if he'd reached a critical point in an interactive video game when game-play freezes and a dialog appears on the screen asking: "Do you (a) tell the flight attendant that your sister is nineteen and her ID is fake, or, (b) let her buy the drink".

"I'll let her... I mean, I'll pay for her drink. I'd like a scotch and water as well, please." Afterwards Sabrina said, "Thanks, that was pretty cool of you. Look, I'm sorry for the way I've been acting. It's just that I've been mad about not being allowed to make the trip alone. If not for you, I wouldn't even be here. So thanks, Todd, really. I mean it."

He smiled as the ice was not only broken, but shattered. "You're very welcome. I haven't been much of a brother to you because of the age difference, but now that we're both adults I sure do hope this changes. I'd like to be a bigger part of your life."

Sabrina smiled warmly. "I'll drink to that."

As they sipped on the drinks, ordering a few more afterwards, they shared the videos and a bunch of digital photos.

"Where'd you get all of these?" she questioned.

"I was in dad's den a few years ago when I came out for Thanksgiving. I opened a closet door and saw some things on the top shelf. It turned out to be a box full of pictures along with some unlabeled video tapes. I asked dad if I could borrow them, then took them down to a shop in town and had them digitize the whole lot. Sure glad I did. There's a lot of family history here."

"I'm glad you did too. Can I get a copy of them?"

"I don't know," he playfully hesitated, trying to use this as leverage. "If you don't run off on me while we're in Greece, I'll be happy to. But not until we get back."

"Blackmail? I thought you were a marketing director."

"Not for the next two weeks," he clarified, fighting back an urge to laugh as he kept a dead-pan expression on his face. "No... for the next two weeks... I'm a babysitter."

She gasped aloud as her face widened in shock. As her expression was replaced by feigned anger she playfully slapped his left shoulder several times. "You jackass, I am not a baby!"

He countered with, "Tell that to our father."

Once his supply of family memorabilia had been exhausted, they were able to hold an enjoyable conversation. He shared about his divorce of a year ago, admittedly a large part his fault due to the demands of his job that he refused to give up. Sabrina talked about the highlights of high school and how nervous she was about starting college.

Afterwards, yawning and stretching her arms, her mind buzzing and body relaxed from the drinks, she told him she might be able to sleep now.

"This is the best part," he joked. "Babysitters always love it when the baby goes down for a nap."

She tried to look mad but couldn't suppress a giggle. "Okay, jackass, keep it up and we'll see who the real baby is."

* * * * *

If Sabrina was anybody other than his sister, he'd be thinking that he was being "led on". As she leaned toward the window, her body in a fetal position on the seat, her skirt kept riding up. To try and hide her immodesty Todd continually grasped the skirt along her right thigh to lower it, the back of his hands brushing along the silky skin of her upper thigh.

A minute or two later she'd shift again, causing him to repeat the action. Each time it did, it sent a tingle through his balls, a feeling he only hated because of her being his sister. Any other woman would've had him hard. As he sat there, thinking, he began to give in to the forbidden secret desire that had been eating away at him for so long.

Perhaps twenty minutes elapsed before she rolled over, now facing him, still curled up. Thinking she looked uncomfortable, he gently manipulated her body to raise the armrest between and pulled her tightly curled body a little more open and rested her head on his lap. He fought back the urges as his cock began to harden, willing it to remain dormant. What she did next made that impossible.

Rubbing the side of her face against his crotch several times, placing a hand on him there and squeezing twice, his erection could be restrained no longer. Despite all of his mental efforts, his cock expanded, the bulge growing, pressing upward against her cheek and fingers. It lasted for maybe a minute or two before his arousal cooled off.

Bending down, brushing her silky auburn hair away to expose her left temple, he lightly kissed it. "I love you, Sabrina. I always have, even more now. You have no idea how proud I am of my kid sister and the incredible woman she's grown into. You're nothing short of awesome."

He was pretty sure he saw her full, pink lips bending slightly, if briefly, into a faint smile. But he wasn't confident enough to know that she had.

A short while later he heard his sister's sleep-breathing. He kept a hand on her, lovingly caressing a shoulder, unable not to stare at her breasts that he was pretty sure she wanted him to see as they pressed against the thin halter, their outline and nipples clearly defined. As wrong as he knew it was his gaze kept returning to the erotic sight, and every time it did he had to will his growing erection away.

When an announcement was made that they would soon be starting their descent, Todd couldn't help himself. Feeling playful as he always did, always playing pranks on others in high school and college, he saw an opening here.

Sliding a headset connector into a jack of the tablet computer, he carefully placed a headset over her ears. Launching a digital movie, the same movie she'd been forced to watch the previous evening, he advanced it to the point where a young woman Sabrina's age was hiding under a bed in an apartment in a foreign country while bad guys were searching for her.

"Nooooooooo!" the woman cried out, the cry jolting Sabrina from her sleep as the woman in the movie was found and yanked out from under the bed.

As she woke up, immediately sitting upright, at first shocked, her blurred eyes soon sharpened, as did her mind. It took a moment before she saw the tablet computer playing the movie she'd seen the previous night of a girl being abducted. Eyes narrowing, she turned to her brother.

"Not funny, jackass."

He couldn't help but laugh. "Maybe? Just a little?"

After rubbing the sleep from her eyes Sabrina looked into her brother's. "I love you too, Todd. I always have, even more now." His sweet, eloquent words were returned, but in a mocking tone.

"I was wondering if you were awake then."

Her body pressed against his, breasts compressing against his chest, their arms embracing, and nipples noticeable. "I just want to enjoy this summer vacation. Please tell me I can."

* * * * *

It was summer and they were in Greece! Their father, suspicious of Sabrina's motives, made sure that his replacement, in this case his son Todd, shared the same room as his daughter. It was awkward in the morning, at times requiring him to leave so she could "do her thing".

"I'm sure they have some other rooms available," Sabrina called out from the bathroom as she styled her hair. "You might meet a woman and need some privacy too."

"You have no idea what dad pays for babysitting," was his response.

"Fuck you, Todd!" she exclaimed before kicking the bathroom door shut.

Admitting to himself that their father could be overly protective of his daughter, and wanting to give his sister some space, he rented a room two doors down. Close enough to be handy, yet not feel too overbearing... but he wasn't telling her just yet.

* * * * *

"It's so beautiful here," Todd said as he and his sister, wearing swimsuits, settled onto the beach not far from the water in the back of the resort they were staying at.

"It's amazing," she agreed.

Todd had been trying not to stare at Sabrina, but he found it impossible. She looked so damned good! First on the flight over, showing him her sleek legs and perky, naturally firm breasts and the pink nipples through the thin top she was wearing, and now this. He was wearing dark sunglasses less to ward off the UV rays and more to disguise his staring.

Sabrina was wearing a tiny pink string bikini that hid very little. As he laid down on an oversized towel she was setting hers up, giving him an opportunity to enjoy her shapely curves and the jiggle of her boobs as they shifted under the bikini-top until she sat down beside him.

"Can you get my back?" she asked, holding up a plastic bottle of sunscreen.

"Sure," he agreed, sitting up on his towel.

Todd squeezed some lotion onto one palm and started vigorously spreading it across her shoulders, and then her lower back. He loved the tropical scent as much as the silky feel of his sister's skin. The contact had his cock stirring again.

"Can I get the front?" he teased.

Sabrina smiled a smile he couldn't see as her nipples hardened at the thought. "Dream on, older brother."

He was propped up on his elbows so he could view the beach, and those wandering across it. Todd was impressed by the beauties passing through his field of vision, enjoying the enticing views of scantily-clad female humanity. While his father's request for him to take two weeks out of his life to chaperone his kid sister seemed like a huge inconvenience at the time, he couldn't help but rethink that position now.

"I'm going for a swim," his sister announced as she got up and walked toward the water.

Todd stared at Sabrina, whom he found as gorgeous as any other woman he'd seen to this point. His gaze settled on her tight ass as it swayed seductively, his cock stirring with arousal as he did. He scolded himself for deriving pleasure from watching her, but not even this kept him from doing so.

Does she really love you? he asked himself. Was she mocking my confession because she felt differently, or maybe she was too uncomfortable to admit it in a serious manner?

A dark-skinned, handsome guy about his sister's age swam up to her and they started talking. Todd was curious, but not enough to miss viewing opportunities of other women. Before he knew it he'd lost sight of his sister. Recalling his father's warning about how sneaky Sabrina could be, he sat up and began looking around. It wasn't until he stood up and turned around than he spotted them on the deck of the hotel sitting at a table, sipping a drink.

Abandoning the towels he walked in their direction, watching as they were conversing and laughing. As he approached Sabrina flashed him a desperate expression and so he simply passed by them, sitting at a table nearby, and ordered an Ouzo.

As the day progressed Todd felt less like a babysitter and more like an unwelcome bodyguard. By mid-afternoon he was tired of it. Settling back down on his towel under the brightly shining sun he cared less about the whereabouts of his sister and more about the relaxation he deserved.

He wasn't sure how much time had elapsed, but it wasn't until late in the afternoon, close to dinnertime, when Sabrina returned.

"Thanks, Todd. Thanks for giving me some space."

He glanced up in time to enjoy the view of his sexy sister as she sat back down.

"Who's the guy?" he asked.

"Adonis," she answered. "His dad owns the hotel we're staying at. He's really nice. After dinner, can we go out tonight? He said there's a club right down the street, said it's real popular. Can we?"

He couldn't help but smile as he heard the growing excitement in her voice. "Of course. It sounds like fun."

She leaned over and briefly kissed his lips in appreciation. Unexpected, it ended before he realized. But her scent, and the memory of her soft, sweet lips, remained with him.

* * * * *

"How do I look?" she asked as he sat on a chair in the hotel room reading a book he'd brought with him.

She was wearing a bright red dress that beautifully accented her dark red hair. He found it difficult to pull his gaze away from her magnetic, innocently sultry brown eyes to admire the rest of her. When he did, he began to admire the details.

The dress strap looped around her neck and lowered to join the body of the garment, with a deep V designed to reveal her captivating cleavage. Either her breasts were naturally closely packed, or the fabric containing them compressed them into the alluring shape he was enjoying. The nipples were covered but their outward appearance was noticeable. The length was nearly the same as the skirt she'd worn earlier.

Sabrina smiled with pride as she saw him closely inspecting her. His expression spoke volumes and it fed her fragile confidence and budding self-esteem. When he appeared to have finished with the front, she turned to reveal the back.

"You should return it," he teased upon seeing his sister's magnificent backside. "They only sold you half a dress."

She giggled. "Very funny. Do you like it?"

"No," Todd decided as he gazed at her shoulder blades and the way that her body curved in at the waist before flaring out again to form her hips. She had a great ass, tight cheeks, with a great shape to them.

Her head turned to look at him. "No? You don't like it?"