Breaking Ann Ch. 01

He removed both cocks and walked to the head of the table. He began removing the gag as he bent down and whispered in her ear "I want to be able to hear you scream as I shove my cock up your hot, tight ass."

Returning to the foot of the table, he lubed himself up, fisting his cock, savoring the moment. He recalled the events of the night and realized his buddy Jim's theory was probably right on target -- she needed the domination, needed the feel of helplessness in order to enjoy herself.

"Slave, your asshole will now be penetrated and you will take it. Do you understand? Answer me or you will regret it."

"Yes ... Master," Ann weakly replied.

"I will bury my cock deep within your bowels and you will ask for more. Do you understand, slut?"

Once again, Ann replied "Yes, Master."

Rick grabbed Ann's thighs, lining his cock up at the entrance to her tight, lubed passage, pressing on the pucker, soft and slippery from it's earlier assault.

"Slave, I will fuck you hard and deep until I am through with you and not a moment less. I will fuck you in your virgin asshole and when I command it of you, you will come and then I will fill your bowels with my cum. Do you understand this, slave?" Rick said as he slapped her ass hard.

"Yes, Master. I understand". As the words were leaving Ann's mouth, he grabbed her hips tighter and stabbed into her. His thick, meaty head popping through the tight ring as Ann wailed "Aaaarghhhhh, nnnnnffffffff, aaaaahhhhh!!!!"

"Take it my slut, take it! Thank your Master as he splits your hole open!" Rick cried as his hand found her clit and he sank another two inches into her.

"Thank ... thank y-y-you Masteeeeeerrrrrr! Owwwww... ahhhh ... nooooo. Stop Rick! Stop! I can't do this! I can't take this!" Ann wailed.

"Ungrateful cum slut! I decide what you will do." Rick said as his hand came down hard on her upturned ass cheeks. "You will address me as Master and take all of what I see fit to give!"

His hands clawed their way up through her splayed legs, up her torso, nails digging in, until they reached her breasts. He grasped her nipples between forefinger and thumb, rolling them around briefly before clamping onto them, pinching, twisting and pulling.

"Right now I decide you will take more of my cock," said Rick as he squeezed her nipples brutally, pulling back from her burning asshole before plunging in nearly four in one powerful, brutal stroke.

"Nooooo ... aaaaahhhhhhhhhh! Uuuumfffffff!" Ann screamed out as she was opened by Rick's thick shaft. She had taken a five inch dildo earlier, but it could not compare to the thickness and length of her husband's fat rod stretching her wider than she had ever been.

Rick steadied himself, moving his hands back down her body to spread her cheeks even further, mesmerized by the sight of her pucker pulling taught around his cock, stretched and shiny with lube. With a sure stroke, all four inches were pulled out and now five shoved back in quickly, not giving Ann time to protest. Small whimpers escaped her lips as she began to pant. Rick stayed very still, feeling her muscles strain and tremble as beads of sweat broke out on her body.

"Mmm," Rick moaned. "You should see what I am watching, my pet. I am watching your virgin hole being split in two."

He began to trace around it's rim where it was grasping his cock. Once again without warning, all five inches came out and returned to her bowels as Ann's mouth gaped open in a scream, but no sound came out.

Rick knew this was only the beginning. Her true deflowering and submission would come in a few hours when Jim arrived. He was only getting warmed up, teasing her, preparing her to be taken fully. He couldn't resist and snaked up finger up into her cunt, feeling around in the hot tightness. By now she was sopping wet. Despite her protests, her body was succumbing and Rick knew it wouldn't be too long before her mind succumbed as well.

He pulled his slick finger out of her and rubbed the juices on her clit. The twitching it caused in her asshole involuntarily milked the head of his cock and caused her to whimper at the new movement in her burning ring. Upon seeing that, Rick began to flex his cock inside of her, causing her pain and making it -- and Ann -- jump.

They stayed this way for nearly half an hour more, Rick alternately manipulating her click and cunt while his cock held open her tight ring. He mixed pleasure and pain, causing his cock to twitch inside of her, bumping her rectum in previously unexplored places but never going any deeper. She whimpered, panted, and sometimes yelped, but Rick would not relent.

Enjoying every reaction, he would use a firm voice and describe what he was seeing, what he was feeling, what he would do to her all the while making it clear that she was helpless and at his mercy. He would bring her to what he thought was the edge of release only to refuse her. Her body was now drenched in sweat, her whimpers few and her hole giving up the fight. Very slowly he withdrew as she panted. He looked down at her stretched hole and watched as it slowly closed then inserted a finger. Ann did not protest. Yes, she would now be ready.

Withdrawing his finger he approached the head of the table and fit the cock gag in her mouth. Stroking her hair, he whispered "Very well my pet. I see you are learning quickly and that pleases your Master. I can't wait to see your asshole stretched and filled with my entire cock. I only allowed you half my length tonight. Next time you will take it all and beg for more."

He squeezed the ball on the cock gag and sent a small burst of liquid down her throat. She was drifting off within minutes and was fully out by the time Rick had finished cranking down her legs and returning the table to it's original state.

While waiting for his friend to arrive, Rick cleaned the toys that had been inside his wife and showered. Before long, Jim was at the door with a big smile on his face and joined by his wife Linda.

"I hope you don't mind, Rick. Linda begged to come with me. She agreed to stay out of the way."

It never ceased to amaze Rick that such a respected couple in the community, Jim a family physician and Linda a paralegal, were so active in sexual practices that were still considered taboo by many of their peers. He'd been to a swingers party with them a few years ago, right before meeting Ann, and was present for Linda's anal deflowering, even participating in her first double penetration. They were memorable occasions for him, having been the only times he had ever been involved in such things and Rick was now returning the favor. He was actually thrilled to see Linda and thought it only fitting that she participate.

"Don't be silly, Jim," Rick said as he reached out to hug Linda. "I'm sure we'll be able to find something for Linda to do."

"Great! Anything goes, guys," said Linda as she embraced Rick.

Rick chuckled, grabbed her ass and said "Yes, I remember."

All three went in to revise Rick's plan to include Linda. Linda had hoped she would be asked to join and had a few things in mind already. Oh, the possibilities! Within an hour, they had their supplies gathered and were all eager to begin the breaking of Ann.