"Silena was gorgeous, Charles knew it and so did she. His mom was dating Silena's dad, and though both Charles and Silena were grown and in college, their parents were getting serious and they wanted the "kids" to behave like brother and sister. The problem was that when he was around her all Charles could think about was getting in her pants, and as far as he could tell all that Silena thought about was getting away from him. It was not a situation that was likely to end well, but neither of them was willing to tell their parent that nothing would make them siblings, including the marriage of their parents.
"There had been more attempts to bring the "family" together than either of them cared to remember, but this latest was the biggest catastrophe yet. At first the idea of a Caribbean cruise had sounded fantastic to both of them. Charles had imagined a week of scoping out girls in skimpy bikinis, while Silena had planned to spend the days quietly getting the best tan of her life and possibly spending an evening or two with some latin hunk that would notice her among all the other nubile young women aboard ship, and leave her with a memory to cherish all winter in their cold Minnesota home."
"Naturally, their parents had made other plans, and those plans were not compatible with their ideas on how to best enjoy this vacation. Virtually all their time had been spent together in planned activities that both Silena and Charles had hated. The one thing that they had agreed upon was that their parents were definitely not up to speed on their interests, evidently thinking they still enjoyed the same sorts of activities they had when they were twelve. It had taken only a few hours on their third day for Silena to come up with a scheme to get out of the latest round of family fun.
"Dad, I'm feeling a little nauseous, I think I better go back to my cabin and lay down for a while" she had said, and her dad had willingly acquiesced after his mom had made a fuss over her feigned illness.
Now Charles was fishing for an excuse to excuse himself, when one virtually fell in his lap.
"I should go check on Silena" Steve, her dad, said."
"With a sudden stroke of genius, Charles grabbed at the chance to get away. "Let me, I can come and get you if she needs anything, and after I can go down to the pool and check out the girls" he said, the last bit in a suggestive whisper.
Silena's father was after all a man, and this suggestion caused two things to occur to Steve almost simultaneously. First he realized that Charles might enjoy some time alone on the ship to seek the pleasures of the opposite sex, and second he realized that accepting this bargain would give him the chance to get Charles's mother alone for a time.
"How thoughtful of you Charlie" his mother said, and as Steve nodded his approval of the plan, Charles knew that he had finally achieved his freedom."
"Pausing only long enough to grab the spare cabin key from Steve, Charles made good his escape. He fully intended to pop in for just a moment and complement Silena on her own escape before looking around the ship for something or someone more interesting to spend his evening with. When he got to her room, he knocked quietly, and when Silena didn't answer, he knocked a little louder. After she still didn't answer, he put the key in the lock and turned it.
When he went in the cabin was dark, only a small lamp across the room was illuminating the room. Silena was in bed snoring lightly face down wearing nothing but her bra and panties, which happened to be a thong that divided the sweetest ass that Charles had ever seen. Beside her on the bed was a bottle of Scotch that was almost half gone."
"It was pretty obvious that Silena had managed to get her hands on the booze, and came back here to enjoy it. She was passed out drunk, and Charles found himself just staring at her sexy ass, thoughts of a less than brotherly nature flying through his mind. His cock, having no more conscience than any other began to harder, tenting his loose shorts as it struggled to be free and closer to the object of his desire."
"He walked over, initially thinking to cover her, but he couldn't bear to look away or cover up such a sexy derriere, especially when Silena was utterly oblivious to his presence as far as he could tell. He wanted her desperately and this was likely to be as close as he would ever get.
Before he even realized what he was doing, he had loosed his cock from his shorts and began to stroke it slowly. Before long he was deep in a lust fueled daydream. In his mind he was pulling that tiny bit of cloth down off her ass, and opening her sweet buttocks to give his probing cock access to her tight little pucker. Silena was begging him to stop in his dream at first, but soon she was crying out in pleasure as he plunged over and over again into her toned backside."
"Silena could feel a presence in the room when she awoke, startled awake by some uncertain sense that things were not as they should be. She could hear a soft rhythmic sound somewhere above her that sounded vaguely familiar. Cracking one eye open just enough in the dim light to take in the room she was shocked to see that someone was in the cabin with her. It took a moment to register what was going on, but those shorts bunched around the ankles in front of her could only be Charles's. Silena's drunken mind ran through a gamut of emotions from surprise to anger to lust in short order.
By the time she could respond she knew that if she startled him, it would not only scare him but also it could cause a cascade of poor choices to befall them; not that what she was thinking now was a good choice, but don't wake a girl up spanking your cock while staring at her nearly naked ass and expect rational thinking! She had an idea that she hoped wouldn't scare him off. She was going to fake talking in her sleep."
"Oh Charlie, not my ass!" she moaned out quietly.
The sounds above her stopped suddenly. She knew that he was now probably freaking out, but if she didn't move and continued to appear asleep for a moment he would realize what he'd heard and stay to hear if there was more.
Sure enough, all was quiet for a few tense moments but soon she heard the sounds of his stroking begin anew, she knew she had him. Moaning quietly, she slid her hand down her side, sliding it under her, all the while keeping her eyes tightly shut and listening closely to his labored breathing."
"Oh Charlie yes! Yes, you can put it in my ass, just be gentle. Let me finger myself a little first. Will you watch me finger my tight young pussy for a minute before you stick that big thing up my butt?" She hadn't really enjoyed anal sex before, but realizing that teasing him this way was very likely going to end up getting her fucked in her ass before it was over. At least, she hoped, if he was any good and liked what he got they could have more fun later.
His strokes were picking up speed and his breathing was coming more rapidly. She needed to distract him, or she was going to have to do more than warm herself up alone. Her hands were both inside the little triangle of clote covering her sex. As she opened her now wet labia with the fingers of one hand, she slid two fingers of the other hand deep into her soaking pussy. Arching her hips up, she pushed her tight ass upwards towards him."
"Pull down my panties and watch me Charles, watch me finger my pussy" she begged, moaning softly as she wriggled her ass slightly. She didn't know if he would do it, but at this point if he didn't she was going to look at him and take the chance.
George couldn't believe what was happening. He had watched and listened, and he was starting to question whether she could still be asleep, but whether she was dreaming or awake and taunting him, she was thinking of sex with him, and not only sex, but she was offering up her ass. That would be a first for him, though he had often thought about it. It was too great an offer to pass up, even if it caused more tension in their already tenuous relationship.
"Yes Charles" she whispered as she felt his trembling fingers on her hips. Slowly he pulled the thong down her hips, and she moaned her pleasure quietly as she pumped her wet fingers into her pussy."
"Switching hands she let the other hand take over in her pussy, as she drove her hips higher, and placed one of her soaked fingers against her tightly puckered anus, running it around the tiny orifice in a slow circle.
"Finger it Charles; finger my ass" she whispered.
Charles wasn't sure if he should follow her directions, as he didn't know for sure whether she was awake or not, but he couldn't turn down the chance at this point. With trembling hands he grasped one of her firm buttocks in each hand, and thrilled as she sighed with pleasure at his touch.
"There is some lube in the draw" she said, voice made husky with lust.
He knew now that she was awake, and that made him much bolder. Opening the drawer, he had to push aside a large pink vibrator to reach the lubricant, and as he did he got an idea. Taking out both items, he squirted some of the lube into one hand, smearing it all over his fingers and rubbing a large amount onto the vibrator. Turning on the device, he lowered it to her pussy and began pushing it into her."
"Silena heard the vibrator come on, and wondered if he meant to put it in her ass, but shuddered with pleasure, moving her fingers down to work her throbbing clit as he pushed the studded toy deep into her yearning cunt. It was over halfway into her, pumping it in short rapid strokes when he began to push a well lubricated finger into her ass. He was a bit rough and urgent, and for a moment Silena thought to call it off thinking that he was either too excited or too inexperienced, but the continuous pounding and vibration in her pussy was overwhelming.
George was in heaven as her tight ass contracted around his wet finger. He would have paid her for the chance to just finger her anus like this while working her pussy over with her vibrator, but she was going to let him fuck her ass, and his impatience was getting the better of him. She groaned in pain as he pushed a second finger into her tight back passage, but he was merciless as he pushed it in deeper and deeper."
"Silena wasn't thrilled; his fingers roughly sawing in and out of her ass hurt a lot, but despite that the throbbing joy in her sex was growing exponentially. Most guys that she'd given her ass to had simply taken their pleasure and ignored her pain, yet Charles seemed to revel in both, and she found that the pain was oddly pleasurable this time.
Charles couldn't wait any longer, and as he straddled her sexy legs his throbbing cock sought the warmth of her puckered opening like a homing missile. He pulled his fingers out of her ass and guided his cock into her in one smooth motion. As the head penetrated through the ring of her anus she groaned in pain and the tight ring of her anus contracted even tighter trying instinctively to push him out, but his cock was having none of that. Leaning forward over her he used his weight and pushed himself deeper into her bum."
"Her resistance was useless, and as he brought his weight to bear, she cried out in agony. His cock slid deep into her ass without mercy as his hips began thrusting wildly. He slid his hand under her, grasping the end of the vibrator where it hung from her pussy unattended and began to pump it into her in time with his thrusting into her ass. Silena was biting her lip to keep from screaming at first, but soon the pleasure took precedence over the pain and she felt herself climbing faster and faster toward a very improbable orgasm.
Charles's wildest dreams of getting his cock into Silena's tight body were surpassed as she writhed and shuddered, grunting in primal lust beneath his thrusting body as she came. He couldn't believe it, and as her throbbing ass milked his cock, he could not hold back his own pleasure. His cock exploded, pumping hot semen into her bowel in spurts that left him gasping for breath. "It took several minutes before each of them caught their breath enough to move but finally, he pulled his flaccid cock from her ass. As he did she rolled underneath him, pulling him too her to kiss him.
"Oh, Charles, that was the best" she said breaking the kiss. "Why don't you go shower, and we can explore some other options."
"Can we do that again?" he asked.
"Oh, I certainly hope so" she said kissing him once more."
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