Vacation Nightmare - Pt. 01

Rebecca watched in horror as her best friend Susan, was anally taken by a steady stream of men. As each man finished, another one took his place. Each one casually walked up to the poor woman cuffed to the table with her legs held in the air by stirrups. Her body was tilted upward, to make her asshole easily accessible. Her arms were cuffed to the upper corners of the flat table, her ankles locked to the stirrups, and two bars ran over her, one just below her breasts and one at her waist, holding her down. Without a word, and as hard as they could, each man took their turn shoving their cock into Susan's ass.

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Susan cried anew with the beginning of each assault, "Please, no", "Please stop", "I am so sore", followed by crying and screaming throughout each rough fucking. The men didn't say much, but they clearly enjoyed fucking the woman as hard as they could. The men would pull out as far as they could and then ram back in with long, hard strokes. The only difference was that some of the men pistoned in and out quickly, each slam followed immediately by the next, while others luxuriated in the feel of Susan's ass, holding it deeply inside of her, and then pulling out slowly, only to ram into her once again.

Rebecca and Susan had been friends since college, over 20 years ago, and knew almost everything about each other, and Rebecca knew that Susan had limited sexual experience, she had never married and had only an occasional boyfriend, and doubted that Susan had ever been fucked in the ass. Watching her friend take her seventh and then her eighth rough plowing, Rebecca could imagine how painful the fucking must be for her friend. The men were using no lube, and were just going at her as hard as they could, while Susan continued to scream, cry and plead with them to end her misery.

Rebecca was right. When she started the day, Susan was an anal virgin, but that was no longer true. Each assault felt like a red hot poker was being stuck up her ass. The body slams were also causing her pain. Cuffed as she was, she could barely move, and her pubic region was swelling. The men seemed to be doing everything they could to make her experience as painful as possible. No lubricant was used, although thankfully the deposits of cum were helping. Many of the men would reach over with their hands and squeeze and tug on her breasts hard or else pull on her nipples as they fucked her. After several particularly brutal nipple pulls, Susan's nipples had become extremely sore, to the point where a slight touch was agony. But the men just kept on coming, and Susan's nightmare continued.

The truth was that Susan was indeed inexperienced. She thought of herself as a closet lesbian. She had always had strong feelings for her best friend, imagining the two of them gently caressing each other, feeling each other's breasts and gently fingering each other to orgasm. She was no stranger to vibrators, and for over 20 years she masturbated to thoughts of Rebecca. Over the years she had collected a large photo collection of her friend in swimsuits and lingerie shots from when they went shopping together. She would spread the photos out and imagine what it would be like to caress Rebecca's large breasts and to suck and tease her nipples.

It was the one secret she held back from her best friend, never working up the courage to act on it. Rebecca was happily married, and Susan was sure she would be rejected. She had never met another woman that sparked the same desire, and reluctantly she would go on the occasional date with a guy to help keep her lesbian urges secret. .

Rebecca had many admirers beside Susan. She really was something special, with a classical curvy body with double D breasts, large, well-formed nipples, a slight waist and a rounded ass. She was big, but athletic, not heavy. The kind of person you might cast to play one of those comic book heroines with the large breasts that stay magically in place under spandex. And at 5'10", she had long shapely legs that helped her standout anywhere she went. Beauty just seemed to radiate from her. At a bar, or a cocktail party, she was the subject of constant surreptitious glances from both men and women particularly admiring her large breasts and nipple shadow.

Rebecca was naked with her wrists and ankles cuffed to a large wooden X that supported her. The two women were on vacation along with Rebecca's husband Bob. They had been invited to a resort on a small Caribbean island owned by the law firm that employed Bob, who had recently been promoted to Full Partner and was invited to the resort complex as a reward for his promotion. They were scheduled to be there for two weeks, and since this was also planned to be a working holiday with law firm meetings throughout, Bob suggested that Susan come with them as company for Rebecca.

Susan started to plead and beg as man number 8 pulled his cock out her ass. Cum was dripping from her ass onto the floor. The white had a little red in it, blood from the rough anal pounding. Man number 9 walked up. He had the largest cock Rebecca had ever seen, and she knew it was going to be pure agony for her friend. She spoke up, and begged as well, "Please, leave her be. Can't you see that she is bleeding?" He looked up at Rebecca and grinned and lined the tip of his cock up against Susan's now well used hole, and without a word, and as hard as he could, shoved his cock into Susan's back hole, and pushed hard Susan shrieked, the cock was huge and she felt like a log had been shoved up her ass. The man reached down, grabbing Susan's breasts, and with an extremely strong grip turned them into sausages within his fists, using them as handles as he moved in and out of the unfortunate woman. Susan just screamed and screamed throughout the anal reaming.

From behind Rebecca a female voice spoke, "hmmm, looks like Susan is being thoroughly entertained, perhaps it is now your turn Becky." Her name was said tauntingly, with disdain, like a mother talking to a small child who had just been caught doing something wrong.

A woman stepped into Rebecca's view. Rebecca recognized her, it was the senior managing partner of Bob's law firm, Sheila. She was dressed in a black leather corset that displayed her breasts as if they were on a shelf, held in place with half cups. She had thigh high black boots on. And hanging from a belt around her waist was a riding crop.

She spoke again, "Oh Becky, You and I are going to have so much fun over the next two weeks, although I am not sure your amazing breasts are going to enjoy the vacation all that much."

Sheila then ran a gloved finger across Rebecca's lips, and then leaned in and kissed her hard on the lips. Sheila forced her tongue into Rebecca's mouth, while she lowered her gloved hand, and without any warning, shoved two fingers into Rebecca's cunt. The dry leather gloves scraped Rebecca's vaginal walls as they moved in and out, and she tried to cry out, but it was muffled from the aggressive kiss.

Sheila pulled her fingers out, and moved her head away. "Yes Becky, we are going to have so much fun!"