Magdalena's Truth

Sterling Douglas stood at the head of the massive mahogany dining table.

"Gentlemen, this night has exceeded all expectations. The collective work necessary to gain the New York account was phenomenal. I hope you have enjoyed your first reward."

There was general agreement among the men.

"And now, champagne." Douglas clapped his hands, and servants appeared, carrying trays of champagne bottles in ice buckets. They began popping bottles, and serving the guests.

Magdalena sat on a bench near the main door. She was exhausted, but fully satisfied. All she could think about was climbing into bed for a few hours of sleep.

Douglas turned from the table, and approached Magdalena.

"Ready for Round Two?" He smiled.

She smiled back at him.

"No, I think I'm finished for the night. Thank you for this."

Douglas frowned.

"That was not the deal. You agreed to be available for the entire evening."

"I know. I'm sorry, I'm just so tired. This was exquisite. I wasn't expecting to enjoy it as much as I did."

Douglas leaned down, staring daggers into her eyes.

"What you want is immaterial to me. You agreed to be the reward tonight, no time limit, no 'I'm so tired' escape clause, no excuses. You knew the rules before you agreed."

"Well, yes, but-"

"Fine." Douglas was suddenly very calm. "You know the consequences, as well."

"Wait, Sterling, I-"

Douglas had left the room. He spoke quietly, pointedly, to the security staff. He then spoke to one of the servants, who scurried off towards the storage room.

Magdalena watched nervously. She knew the consequences, but did not believe Douglas would deliver on his promise. He frequently threatened repercussions for her behavior, and had not had reason to ever follow through.

Tonight was different. Douglas was furious. The angrier he was, the calmer he became.

Two servants entered the dining hall, followed by security staff. The servants pushed a large, waist high wooden tea cart. The cart had a black box on top.

The security personnel entered the dining hall, surrounded Magdalena, and pulled her to her feet. They stripped her of her blanket, leaving her naked again. They brought her to the tea cart, where the servants unpacked the box. They kept the contents hidden from Magdalena, as it contained multiple restraints and a ball gag. Holding her arms, the security guards forced Magdalena to bend over the cart, and fastened her arms and legs to the cart. She was frightened, but too tired to put up a fight.

Douglas returned to the head of the table.

"Gentlemen, there has been a slight change of plans," said Douglas. "Prior rules are no longer in place," continued Douglas. "The only rule in place now is do not make Magdalena bleed."

At this, Magdalena tensed. She never imagined Douglas would allow her to be harmed. She worried about what was to come.

"Sterling, please, just-" she began.

Douglas sighed. "Gag her. I've heard enough of her complaints for the night."

A servant fastened the ball gag around Magdalena's head. She still tried to protest, but was reduced to whimpers and mewling.

"We shall go by rank, as before," said Douglas. "The difference being, I shall join the festivities at the end."

The room was entirely silent. The prevailing rumor was that Douglas was better endowed than most porn stars. More than one of the men present was looking forward to finally knowing the truth. Unbeknownst to Douglas' subordinates, their collective ranks were chosen in part based on their male endowments. Douglas understood psychological perspective: six feet tall appears larger to five foot two than to five foot ten. He'd heard the rumors, and had facilitated them as best he could.

"Jonesy, you have the honor of being first."

Jones stepped up to the cart.

"Ah, thank you, sir," said Jones. "Nothing is off limits, other than blood, is that correct?"

"Yes, Jonesy."

Jones answered by spanking Magdalena's generous ass. He brought his hand back, and repeatedly swatted her flesh, hitting harder each time. The strikes echoed through the dining hall.

Magdalena moaned through her gag. She was not accustomed to any type of bondage. She had never been tied up in her life, let alone spanked until she cried. Tears rolled down her pretty face as Jones became more aggressive.

Jones stopped spanking, He pulled his erection from his trousers, and without preliminaries, forced his cock into Magdalena's well used pussy. He entered hard and fast, and kept a brutal pace, making her squirm and cry. As he fucked her, he spanked her ass, alternating cheeks. Bright red handprints appeared on the milky white skin of her ass. He could not keep up the pace for long. He pulled out, and came over her ass.

The servant applied a warm, wet towel to Magdalena's back side. This was less for her comfort than for preparing her for her next partner. Douglas stood by the cart, watching carefully.

Walters approached the cart, mesmerized by the reddened female buttocks in front of him. He ran his hands across her ass, prodding the flesh here and there. He opened his pants, and entered her quickly. As he thrust into her, he began playing with her ass. Grabbing the flesh, pulling her buttocks apart, Walters examined her back side as closely as he examined her vagina. As he fucked her, he began to gently finger her anus. He inserted his index finger just past the nail. Magdalena gasped, and wished she could thrust back towards him. He finished inside her quickly.

Miller was next.

"Sir," Miller asked, "am I right in thinking anything goes, now? Short of blood sports."

"Yes. You are correct."

Miller grinned in glee. He'd fantasized about this very situation, but had never had an opportunity. This would be a night of many firsts. He grabbed Magdalena's cheeks, pulling them far apart. This had the effect of stretching her anus. Miller inserted a finger, reaming her hole.

Magdalena squirmed and whimpered, straining against her bonds. Until tonight, she had been an anal virgin. She'd never had a whole finger inside her rectum. The tongues had been delightful, but the finger was approaching pain.

Miller added another finger to the first. She groaned, and started crying again. Her anal ring was expanded farther than she thought it could go. Miller finger fucked her asshole. He added a third finger, slowly fucking her. He pulled his fingers out, and replaced them with his 5" cock. He thrust against her half opened anus, and slowly pushed until the head was just inside her tight ring. She screamed through her gag. Her hands clutched the cart legs. She was afraid she would not survive this evening. Douglas stood to her right side, watching the action, smiling.

Her ass was the tightest hole Miller had ever entered. He climaxed after only a dozen thrusts, for which she was grateful.

Carver and Garcia approached the cart together.

"Sir," asked Carver, "must she retain the gag, or may we use her mouth?"

"Use her as you like," said Douglas. "The gag is merely to keep her quiet."

Carver went to her head as Garcia went to her ass. Carver removed her gag, and gently caressed her face. She looked up at him, happy to be free of the hateful gag. As Garcia entered her pussy, Carver shoved his erection into her mouth. He thrust gently at first, keeping time with Garcia's thrusts into her pussy. She murmured, focusing on the cock in her mouth. Garcia grabbed her hips and started pounding into her, slamming his hips against her ass. Carver picked up his pace, and face fucked her. She held her mouth open, drooling, trying to concentrate on breathing. Carver held the sides of her head as he drove his cock into her jaws. She felt as though she was being torn apart at both ends. As he fucked her pussy, Garcia shoved two fingers into her ass. She squirmed and squealed, choking on Carver's dick. Carver slowed, allowing her to regain her composure. Douglas silently observed, looking annoyed.

Carver achieved orgasm into her gaping, wet maw, and stepped back towards a chair. Garcia fucked her pussy and stroked her anus in perfect rhythm. He sped up, bringing her closer to orgasm. She was panting and moaning, edging closer to climax.

"Finish quickly, but do not let her cum," said Douglas.

Garcia was shocked, but knew to obey. He pulled his fingers from her sucking rectum, and increased his pounding into her honey pot. She groaned in disappointment, knowing her orgasm was lost. Garcia pulled out, and came down her thighs.

Douglas smiled.

"Gentlemen, there is a change in plans. I shall not wait until the end to participate."

Magdalena tensed visibly. He couldn't mean what she thought he meant. He couldn't do this in front of his business staff. Could he?

"Shall I gag her again, sir?" Asked the nearest servant.

"No. I want to hear her scream."

"Sterling, no. Please don't do this. Please!" She began weeping openly.

Douglas laughed. "You knew the consequences when you chose the behavior. Now it is time for my fun."

The servant, who had been briefed prior to the party, checked that Magdalena's restraints were tight and holding her still.

Magdalena sobbed, and braced herself for her worst fear. Despite the attention her tiny rosebud had received, she dreaded full penetration from Douglas, especially in front of an audience. She could barely accommodate him vaginallly. She knew she was in for a painful night. She braced herself mentally, and focused on relaxing her anus as much as she could.

Douglas took his place at Magdalena's rear. She was still crying, and had begun shaking.

"Please, Sterling, please, don't do this! Please! I am begging you. Please -"

"One more word from you, my dear, and you'll get the ball gag again. And worse," Douglas snarled.

Magdalena was shocked. Douglas had never been so aggressive towards her. It frightened her: would she be safe? Would she survive this evening?

Douglas began spanking Magdalena's reddened buttocks. First the left cheek, then the right, smacking faster and harder each time. He kept up the pace with his left hand, as he freed his erection with his right.

The rumors had not done him justice. Douglas was 11" long erect, and nearly 5" in girth. There were audible gasps as he lined his cockhead up to Magdalena's puckered hole. He suddenly stepped back, went to the dining table, and grabbed a cruet of olive oil. He drizzled oil on his cock, then poured some on Magdalena's backside. Using two fingers, he massaged the oil into her tightest hole. She was still sobbing, still shaking, but was beginning to feel turned on. As much as she feared the coming penetration, as much as she hated to admit it, she also longed for it.

"Gentlemen," said Douglas, "until tonight, Magdalena was an anal virgin. She'd never had so much as a finger inside her anus. Now, you will all witness her deflowering."

The men gathered around the cart, craning for the best view.

Placing a hand on each cheek, Douglas spread her ass apart. He rubbed his cockhead up and down her crack. Magdalena tensed when he reached her rosebud. Slowly, he began to push the head against her anus, gradually opening her up. She grunted a painful response. He kept slowly pushing in, an inch at a time. Her anus resisted his intrusion, trying to push him out. When he reached four inches in, he pulled almost all the way out; only his cockhead remained inside her. He steadily pushed back in, going deeper. She was breathing heavily, her body bathed in sweat. It was painful, but tolerable.

Magdalena relaxed momentarily. The pain progressively gave way to pleasure.

Sensing her relaxation, Douglas took the opportunity to slam his entire length into her resisting asshole.

She screamed, howling in pain and shock.

He pulled out, and slammed into her again, and again. He fucked her asshole harder, faster, each thrust more powerful than the last. He banged into her anus as though he were drilling for oil. Despite his ministrations, her anus still resisted him, still tried to keep him out. Her reluctance did not even register with him. His only goal was to take his pleasure in the only hole she had denied him.

Magdalena openly sobbed, pulling against her restraints to no avail. This was the worst pain she'd ever experienced. She knew Douglas had more stamina than men half his age. This would be a long night.

While still furiously thrusting into her generous backside, Douglas reached a hand beneath Magdalena's body. He pushed through her labia to her clitoris, and began grinding a finger against it. She resisted: she did not want to orgasm in front of an audience while being raped anally. She groaned, pleading for him to stop. He rubbed her clit harder, slamming his erection into her anus.

Being stimulated in two places had the desired effect: Magdalena pushed against Douglas' hand, and tried to meet his thrusts. She orgasmed, screaming and crying all the while.

Douglas grinned, and increased his speed into her buttocks. After ten minutes, he climaxed inside her ass. He slowed his thrusts, leaning against her back.

"I kept my promise," he whispered into her ear. "Happy anniversary, my love. I hope it was everything you wanted."