The Amazing Randy Goes All-In

"Black Jack is not only uncommonly handsome, in a scruffy, seafaring way, but he is known from the testimony of those same ransomed women to have an enormous cock, much larger than normal, so large in fact that among rival pirate captains, he is known as 'The Rugbeater.' The thought of that enormous dick both repels and attracts you at the same time."

"When I say, 'now,' you will be on Black Jack's ship, in his cabin, about to be tied, gagged, and fucked by the notorious pirate with the giant cock."

"When I say, 'You're rescued,' you will be back on the island, at Captain Michael Williamson's private quarters, where he's taken you to get cleaned-up and ready to send back to your father at Government House. Captain Williamson was the one who escorted you back to the island after your ordeal. You're attracted to him and, at government functions, have flirted extensively with the dashing Captain of the Guards. You've fantasized about him as a lover and now you're grateful, but his attitude towards you has changed, based on your recent encounter with Black Jack."

"You will experience this as if it were really happening to you, but when I say 'You are released Amy', you will be back here with me, safe, and ready to tell me about your experience, no longer under hypnotic control of any kind. Stand here for a minute, while I light the fire, which you will perceive as a small coal stove in Captain Woolsey's cabin." Randy lit the fire in the fireplace. It was a cool evening and the fire provided both light and heat, not to mention dark ambience for a kidnapping fantasy.

Randy left for the bedroom and quickly returned with a medium-sized black leather bag, which he opened in front of Amy.

"Now," said Randy as he slowly pulled various restraints from the leather bag. Although he preferred heavier gauge leather handcuffs, the novelty store in Sault Saint Marie had a limited selection, so he had to make due with less expensive, but highly portable, lightweight nylon and Velcro cuffs. They'd do, especially if he told Lady Amy that they were leather, or even iron. Out came a faux-leather forearm binder and a leather collar. Lady Amy drew back, speechless from horror, but when "Black Jack" pulled the rubber ball gag from the bag and advanced to secure his captive, Lady Amy betrayed her fears as she cinched her robe around her exquisite figure and quickly tied a bow to secure it, as if somehow it would prevent the pirate captain from his evil designs.

"Please Captain Woolsey, my father, the Governor, will pay a handsome sum for my safe return. Have mercy!" she pleaded. In response, Randy stepped right up to the quaking beauty in the blue satin robe and immediately untied the satin sash which Amy had just secured. Reaching up, he grabbed the lapels and, in a single fluid motion, pulled the exquisite cobalt blue satin covering to the floor. Amy let out a screech of indignation and embarrassment. "No, Captain! Leave me my dignity, please." Immediately her hands moved to cover her breasts, which were rising and falling, threatening to push their way out of her matching blue strapless lace bra, as her breathing picked up, driven by fear and the anticipation of her impending violation by "Black Jack."

Randy's hypnotic suggestions were working perfectly. Other times when they had done innocent role-play in the course of their lovemaking, it had been possible for Amy, for whatever reason, to "step out of character" to get another drink, or go to the bathroom, or just because she wanted to talk to Randy as herself. Not tonight. She had asked Randy specifically to implant suggestions and guide her through a totally new experience, one in which she felt threatened. She wasn't acting.

"Lady Amy," said the Captain of Pirates, "I'm afraid that the leg irons and handcuffs must go on. I can't have you running about here in my cabin with no 'sea legs' under you. I don't want you bruised-up when I return you to your father." Black Jack attached the Velcro restraints to both her ankles and wrists. Likewise, her forearms were secured in the binder as she continued to beg for a mercy which would never come. Black Jack intended to use her for his own pleasure, whatever that might be. She knew this in her heart.

Reaching into his bag, Randy, aka Black Jack, withdrew a number of short chains and clasps. He moved to the center of the rug, reached up to an old carrying beam, and hooked one of the lengths to a single eye bolt he had mounted earlier in the summer in anticipation of this very night. For over a month it had sat there unseen, unassuming; now it would serve as the attachment point for the beautiful brunette bartender who believed that she was about to be raped by a dashing, well-hung pirate.

Despite repeated pleas from the beautiful Lady Amy, Captain Jack simply took her bound hands, as delicate as those of a pampered member of the island ruling class could be, and raised them over her head attaching them to the eye bolt. He stepped back to admire his prize and his handiwork. His captive's beautiful brown eyes were wide open, dashing back and forth, looking for some kind of intervention. Her long hair hung down her back, soft and straight.

"What are you going to do with me, Captain? I demand that you free me from these restraints and treat me according to my rightful station."

"Lady Amy," said Captain Jack, "you are my prisoner. I will do with you as I please. Right now, it pleases me to see you hanging there."

"Let me go!" she demanded.

"Lay off that bilge," spat Randy, who was enjoying the cruel pirate act and trying as hard as he could to talk "pirate talk."

"No! Let me go now, you scum!"

"Scum is it now?" asked Captain Jack as he picked up the rubber ball gag and stepped behind the trembling lingerie-clad captive. Grabbing her long hair, he pulled her head back and licked her cheek with a slobbery tongue. He did it again.

"Ugh," said the strung-up beauty, shaking her head as best she could to get away. "You're disgusting."

"I've heard enough out of you, Lady Amy. Open your mouth," he said as he gave another hair tug for emphasis. Lady Amy defiantly clenched her teeth and shook her head. "Very well," said Black Jack, "then it's the 'cat' for you," as he reached into the bag and withdrew a short leather flogger, not much of a whip, more like a movie prop. "Let's see if a few swats with the cat o' nine tails will put you into a more cooperative mood." Randy whispered into her ear. "Amy you see this small flogger as a much bigger whip and when it lands, you will experience it as if it genuinely stings."

Stepping back, he brought the tiny flogger down on "Lady Amy's" bare back with a "snap!" The beautiful hanging captive let out a shriek, which, if Randy's home were not so isolated, would surely have been heard by neighbors. He struck her again and again she howled. "Stop, please! I will allow you to put that filthy gag into my mouth. She opened wide to receive the gag. In moments, it was firmly attached and Lady Amy's eyes were all she had left with which to protest, and they showed only fear.

Captain Woolsey once again stepped back to examine the beautiful woman whose arms were stretched above her. Her legs were long and lean; her abdomen, while not washboard flat, was slim and tanned as were her arms and face. Her breasts, full and round continued to heave as she struggled to fill her lungs with air.

The pirate captain delivered another blow from the imaginary cat o' nine tails and Amy bucked, while howling into her gag. Her eyes began to tear up. That was one strike too many for Randy, who put down the flogger and reached for her bra clasp, undoing it. The rest of the bra, under pressure from Lady Amy's swelling breasts dropped to the floor, her taut nipples, exposed. With a single rapid motion, he pulled her thong down to her ankles. Amy's eyes went wide as she hung suspended, completely exposed to her captor.

Black Jack moved to within six inches of the beautiful captive, staring at his naked prey eye-to-eye like a mesmerizing serpent. Without a word, the swarthy pirate captain reached down to grab her pubic mound. He growled, "Lady Amy, will you cooperate or is it a few more strikes of the cat to change your mind?" The suspended beauty nodded rapidly in the affirmative. "That's better," he said as he reached up to disengage the chains from the ceiling hook, "and let's have no more of that foolishness."

Once down, Randy allowed Amy to rest for a minute before removing both the armbinder and the Velcro cuffs and re-attaching them behind her back, immobilizing both arms and thrusting her chest forward. Black Jack reached forward and squeezed Lady Amy's tits, using the thumb and forefinger of each hand to pinch Amy's turgid, out-sized nipples, neither lightly nor too hard. Her earlier tears had been a mistake and Randy did not want to repeat Amy's perception of pain. The "pain" part of the evening was over.

It was time for the pleasure part to begin.

Prepare to be Boarded

Captain Jack continued to pinch her nipple, but lowered his hand to grab her sex. Amy's eyes opened wide, but Randy couldn't tell whether it was from fright or surprise. Amy, said nothing through her gag. "Black Jack" stared his lovely captive straight in the eye and spoke. "Lady Amy, if you will give me your word not to make a fuss, I will remove your gag. Will you promise that to me, Lady Amy?"

Lady Amy quickly nodded her agreement for a second time and Captain Jack removed her gag. She stood in defiant silence as Black Jack resumed his indelicate exploration of her magnificent body. This time, the lecherous Captain of Pirates was decidedly gentler with his captive as pinching turned to cupping and kneading both above and below her slim waist. At first, Lady Amy was just relieved that the handsome Captain Jack had suspended his rough treatment, but as she stared at the rugged, worn visage of her captor, she began to focus on the feel of his calloused hands on her most intimate areas, touching, probing, and stimulating a side of her that she had never experienced with a man. She had touched herself before, imagining that it was the touch of a handsome lover, but now that her fantasy had become real, she didn't know quite what to make of it.

After a while, Lady Amy's body began to betray her. She was nineteen, just coming into flower, her beautiful body bathed in hormones, her mind filled with questions. Black Jack continued to tweak and rub, spending more and more time rubbing her pussy, which had gone moist. Her hips swayed back and forth involuntarily in response to his ministrations. Captain Woolsey reached for the restraints with one hand while continuing to stimulate the beautiful bound brunette. In a moment, a chain was attached to her bound wrists and the pirate captain carefully lifted her arms toward the horizontal. In response, Lady Amy's body bent at the waist until her head was a full ninety degrees to her legs and her breasts hung plumb. True to her promise, Lady Amy remained silent.

Randy unzipped his pants and took out his erection. At forty-eight, Randy's penis was decidedly average in both length and girth, but that's not what Lady Amy saw. She had heard all the stories about the size of the pirate captain's penis. What she saw was a truly huge cock, every bit as impressive as the talk had made it out to be. Instead of looking away in shame, her eyes remained riveted on the massive erection, which Black Jack Woolsey stroked methodically and was now a mere foot from her face.

"Prepare to be boarded," said the pirate as he took up position behind the helpless beauty. With one hand, he steadied her trembling body and with the other he maneuvered his cock up against the outer folds of her pussy. He could feel the slick moisture as the tip slipped up and down, coating itself with her precious vaginal moisture. What she felt was the tip of what she believed to be an enormous penis. Black Jack eased the tip between her labia and hesitated, as if unsure whether or not to continue and deflower the hapless nineteen-year-old.

Lady Amy prepared herself to lose her precious virginity. With a single thrust, Randy entered her pussy as deeply as he could. She cried out as she imagined herself being impaled on the handsome pirate's oversized blood-filled rod. Randy grabbed her hips and held his cock in place for a few extra seconds in order to give the hypnotized Amy a chance to savor the imaginary feeling of having her tight pussy full of pirate cock. He started to pump with a steady rhythm as he reached around and fingered her clit, slowly flicking his index finger against her sensitive nub.

Lady Amy swooned as she concentrated on the dual sensations, which The Amazing Randy had hypnotized her into believing to be real. Her hips began to gyrate, pushing back against his cock, all signs of protest having fallen by the wayside. The Captain of Pirates and his helpless, but now cooperating, teen-aged victim continued to fuck, maintaining the rhythm that Captain Jack had established.

Randy had already decided that he would not allow Black Jack to ejaculate. He still had half a fantasy to fulfill. Randy enjoyed bondage with his lovers and it was very important to him that Amy enjoy it as well, but he wanted her to decide for herself. Amy, on the other hand, was capable of having multiple orgasms. He wanted Lady Amy to get off, strung up like she was. Amy was not the only one enjoying their fantasy, which was as it should be, he thought.

Without warning, Captain Jack withdrew his penis and moved his hands to Amy's breasts, which hung vertically from her chest. Had he actually been "Black Jack Woolsey," he would have squeezed both her tits much harder, pinching and pulling her nipples, as a sadistic pirate would. Randy had already decided that he would inflict no more pain, real or imagined, on the woman he loved. Cupping each breast and kneading, Randy, now hunched over Amy's back, re-entered the hanging beauty, thrusting his cock as deeply as it would go and re-establishing his pace. Instantly, Amy resumed her motion, moaning. Black Jack moved his hands back to continue diddling her clitoris. Eventually, Lady Amy broke her new rhythm and began to buck as her swollen clit took over her body's response. She cried out, but made no attempt to disengage from her captor's cock, squeezing with her vaginal muscles instead. Randy increased the pace of his diddling until Lady Amy cried out. Her body stiffened as the wave of orgasmic energy, made all the more potent by her belief that she was experiencing it for the first time, rocked her beautiful body from head to toe.

Captain Woolsey withdrew and immediately removed her restraints. Handing her robe back to her, he said in his gruff 'pirate voice', "Put this back on." Holding up her lace panties to his face to refresh his memory of her unique fragrance, The Captain of Pirates said, "I'll keep this pretty blue lace, if you don't mind. Captain Williamson will come aboard soon to retrieve you and bring me my ransom money. Tell him that Black Jack Woolsey said "I've already cut into the loaf. He can take as many slices as he wants for himself." Randy got dressed.

"You're rescued."

An Indecent Bargain

"Is it true, Lady Amy, that you are no longer pure? Captain Woolsey's message can only be interpreted one way," said the handsome Captain Williamson.

"It is," replied the beautiful "teenager," averting her gaze, embarrassed at her intimate confession to a man to whom she was so strongly attracted. "I trust that you will keep my secret. Should my father discover my shame, he will put me on the next vessel bound for England. This island is the only home I've ever known. I know nothing of England. Please don't tell my father, Captain. I'll do anything if you promise not to tell my secret."

Randy stared at his beautiful hypnotized lover and thought to himself, "She's playing her role as if she had a script." He stepped back to allow Captain Williamson to get a better view of the beauty who had just offered him his pick of rewards. Standing there in her blue satin robe, Lady Amy radiated both innocence and desperation. Captain Williamson spoke. "Such as what, Lady Amy? What are you prepared to offer me to secure my silence?"

The stunning brunette reached down and undid her robe, allowing it to drop to the floor in silent answer to the man about whom she had so often fantasized. "I'm offering you a "slice of the loaf," Captain," said the beauty in the coral blue bustier and garter belt.

"Lady Amy," said the Captain of the Guards, "I can assure you that I have no interest whatsoever in following Captain Woolsey's 'John Thomas' anywhere, even into such an alluring place. I will not coat my cock with his leavings."

Amy's face dropped. "Captain Williamson... Michael," she said using his Christian name, "although that ruffian did rob me of my maidenhood, he did so by force, and he did not leave his seed inside me. There are no 'leavings.'

"Nevertheless, I will not go where that bastard pirate has been."

"What am I to do, what will you take from me?"

"Again," said the handsome and dashing Guards Captain, "what will you offer?"

"I am yours to take, just please do not reveal my secret."

Randy stood by the couch and motioned for his hypnotized lover to come to him. Lady Amy walked straight up to Captain Williamson, tilting her head to offer a kiss. With a single motion, he turned his head to decline her offer, instead, he put his hands on her tanned shoulders and slowly forced her to her knees. Keeping one hand on her shoulder, he reached down and unhooked his trousers, which slid to the floor exposing his "John Thomas" to the lovely brunette.

Amy balked when he began to push her head toward his rising erection. "What do you want from me, Captain?" she asked.

"I want you to make good on your offer, Lady Amy. Open your mouth and mind your teeth."

Lady Amy knew that if she wanted to ensure the Captain's silence, that she would have to submit herself to his lewd demands. She opened her mouth and closed her eyes. Captain Williamson grasped her long beautiful hair as if it were the reins on a three-year-old mare being broken for cavalry duty and drew her open lips to his cock, which he inserted slowly into the warm saliva-coated cavern. Instinctively, Lady Amy allowed her lips to close around his cock as he slowed his intrusion to a halt and then slowly withdrew his penis and re-inserted it as he increased his piston-like invasion of her mouth and throat. He pulled her hair harder as he felt his spunk begin to rise towards ejaculation.

"Lady Amy, if you desire my silence, you will welcome my essence into your mouth, and then show it to me before swallowing it, all of it. Nod your head if you understand." Lady Amy, mortified, nodded her head in the affirmative and prepared herself for Captain Williamson's ejaculate. She didn't have long to wait. In less than a minute, Captain Williamson's cock exploded into the back of her throat. As more and more cum shot from the tip, he slowly drew his penis back to give Lady Amy a place for his jism to go. Four individual spurts of the warm slippery fluid filled the kneeling beauty's mouth full.

Lady Amy did as she was instructed and lifted her head without spilling so much as a drop, and showed the unchivalrous Captain of the Guards her cum-filled mouth. "Now, swallow it all, every drop," commanded Captain Williamson. This she did without protest, opening wide to prove that she had done as she was told.

Lady Amy's fantasy had come to an end. All that remained was for Randy to bring her back to the present. Randy spoke. "You will go into the bathroom and refresh yourself, including washing your mouth and brushing your teeth if you like, and then return to this room for further instructions. Amy did as she was instructed and left the living room for the bathroom in the master bedroom.