Educating Michael Ch. 06

DISCLAIMER- This is a series of fan fiction. This series follows on from the events depicted in Alex in Wonderland. You should read that series first to know about the characters. The original characters can first be seen in ONLINE CHASTITY by FICT chapters 1-6

(Michael gets carried away)

Sam was in the bedroom of her lofthouse. She was hanging by her wrists from the ceiling with the cuffs that were attached to chains that retracted up into the ceiling itself. She had been placed in this position by Michael. He had raided her cabinet to use her implements of kinky sex against her at her own urging, he needed no second invitation. This was supposed to be a night where Sam would let Michael release his tensions with some casual sex, however, he had effectively turned the tables on her after she challenged him to show her his wild side.

Her ankles were strapped to her thighs which kept her legs apart, allowing him easy access to her pussy and ass. He was also using the tripod cameras to record everything and he still hadn't allow her to cum. Even now he was fucking her in the ass again with his nine point four inch cock, he had placed a six inch dildo gag in her mouth so she couldn't speak, just groan and drool onto the floor.

He reached around and grabbed her throat and turned her head to face one of the cameras, he used his other hand to cup one of her breasts as he continued to drill her ass for the second time this evening. He then used his tongue to lick her ear.

"Is this wild enough for you, Miss Sam?" He asked. "Or would you like to see more?"

Sam nodded and grunted on her gag as he withdrew his cock almost all the way out of her ass then rammed forwards brutally impaling her.

"Yes to which, Miss Sam?" He hissed in her ear. "Both?"

He rammed her ass again with all his strength and she wailed into her gag and threw her head back. She nodded again, suddenly enjoying the loss of control and decided to let herself go despite the cameras recording everything. She admitted to herself that she wanted this, things had become stable since Alex came onboard but stale, despite the current success of the business.

Michael continued brutally fucking her ass for several minutes, all the time Sam groaned and, at times wailed, into her gag. He would occasionally stop, with his cock fully inserted in her ass, so he could slap her ass cheeks with both hands, making her jump as the cheeks turned bright red.

He felt his second orgasm approaching and withdrew his cock so he could shoot his semen up her back, soon he began rubbing seven shots worth of semen over her shoulder blades and back.

Sam was now covered in two loads of his semen, she hadn't been debauched this way for years now and still he would not allow her to cum. She was panting heavily and drooling saliva from the dildo gag in her mouth.

Michael stepped back then moved to stand in front of her, he then very gently began stroking her pussy with his fingers. This sent her into a frenzy of lust and desperately began thrusting her hips forward in a futile attempt to cum. Michael simply withdrew his fingers and smiled at her.

"Not yet, Miss Sam!" He gloated. "Not yet!"

He then left the room, leaving her hanging but soon returned carrying two objects that had Sam looking at him wide-eyed. He was carrying the six inch thrusting dildo that she first used on him when first came to the lounge, In his other hand he was carrying a similar dildo, this one however was eight inches long that extended to ten inches when thrusting. He held up the six inch dildo to her face and smiled.

"I didn't realise this dildo had a big brother, Miss Sam!" He said good naturedly.

He immediately began positioning the six inch dildo and pushed it into her ass. He used plenty of oil before twisting it past her well worn sphincter and pushed it fully home. Then he held up the larger dildo, Sam had forgotten she even had it and had never used it before, he coated it with more oil and slowly inserted it into her pussy. Sam began to shake in her bonds and threw her head back, wailing at the sheer size of it as it hugged her pussy walls. It was bigger than Michael's cock and wider and the thrusting extension, which she now dreaded, would make it even longer.

Sam looked at him with pleading eyes as he reached down and switched them both on. They immediately began their work causing her to jump and groan, she began to try to escape her bonds knowing it was impossible. She could feel that he had put them on a low setting ensuring that she would not be able to cum but very soon her holes were beginning to ache. Michael smiled at her again.

"These dildos were on charge next door, Miss Sam." He said. "The batteries, according to the instructions, have about two hours of continuous use so they should keep you distracted for a while."

All Sam could do was groan and shake, she knew there was no escape until Michael allowed. She closed her eyes.

While her eyes were closed Sam felt a stinging pain on her right nipple. She snapped he eyes open and screamed into her gag as she felt another sting, this time to her left nipple. Michael was standing in front of her holding the leather spanking crop with an evil glint in his eyes. He then moved behind her and she soon felt two stinging blows to each ass cheek making her scream again.

"You didn't think I was going to forget about the pain you inflicted on me during my training did you, Miss Sam?" He whispered in her ear.

Sam whimpered and sobbed as he ran the crop across her back before she got two more blows to each ass cheek. She jumped and screamed into her gag, before she could catch her breath, however, she felt two blows to each shoulder blade. She tried to look around at him but he pushed her head forward and slapped her twice under each armpit.

She could do nothing but scream and shake in her bonds, all the while the dildos were doing their work, the larger one in her pussy keeping her close to orgasm.

"Thank you very much for teaching me how to inflict pain, Miss Sam." Michael said. "But I thought I would mix it with pleasure. I hope the dildos take your mind off what I am going to do to you."

Sam watched him as he moved to stand in front of her again, eyes wide with genuine fear at what he was going to do to her. He moved towards her and her eyes were fixated on the crop that had never been used on her before. He held her right breast and gave the nipple another slap before doing the same to the left breast.

Tears were now streaming down her face as he slapped the flesh of her breasts with the crop, alternating between the right and left. This sent Sam into a frenzy and she desperately tried to free herself to escape the crop as Michael stepped back to observe her sobbing for the first time he met her. After a few minutes he reached forwards and removed the dildo gag from her mouth.

"Please, Michael!" She gasped. " No more! Please!"

Michael just smiled at her.

"We've only just started, Miss Sam." He replied. "You're giving up already?"

Sam looked at him with tears in her eyes as he clearly mocked her endurance, she took a deep breath.

"At least release my legs so I can stand." She begged. "The strain is too much on my shoulders."

Michael thought for a moment then stepped forward and released her thighs so she could stand and the pain in her shoulders began to recede. He then moved behind her and for a few minutes massaged and kneaded her shoulders with his hands and fingers.

"There. Miss Sam." He said. "You rest for a while, I'll be right back."

With that he left the room leaving Sam still sobbing with nasty red marks beginning to show on her nipples and breasts, she knew her ass and back would be looking the same. She began to think she had made a mistake, Michael now had access to all of her equipment and she was clearly at his mercy, the irony of him only being nineteen was not lost on her. Still the dildos were buzzing away keeping her horny.

Michael soon returned with some ankle cuffs and a spreader bar which he place on her without saying a word. She was now standing spreadeagled before him, a complete role reversal from several months ago. He then picked up the crop again and smiled at her as she tensed up, expecting more punishment.

Ninety minutes later Sam was an absolute mess. She was now covered in hundreds of welts all across her body where he used the crop on her. He even removed the dildo in her pussy so he could slap the outer lips with the crop, all she did was wail and scream and stream an never ending flood of tears down her face.

No part of her body escaped and yet she was still very horny with the dildos still buzzing away, Michael walked around her to inspect her body and then stood in front of her.

"It looks like you'll be wearing your full catsuit, Miss Sam." He said. "That's if you want to hide those marks from the others. By the way, do you like my wild side?"

Sam said nothing but sagged in her bonds, her chin on her chest, weeping softly. If she were not chained to the ceiling by her wrists she would be crumpled on the floor by now.

"Please, Michael." She sobbed. "Let me cum! Please!"

Michael smiled and knelt down to remove her ankles and spreader bar, He then stood in front of her again with his cock still erect after all this time.

"If you want to cum, Miss Sam." He said. "I'll let you start. Get your pussy on my hard cock."

Sam looked up at him, shocked at what he wanted her to do. Seeing no choice she managed to raise her welt covered legs and wrapped them around his waist. She then lined up her pussy entrance until she felt his cockhead against the outer lips.

Michael then gripped her ass cheeks and forced his cock into her pussy nice and slowly, she began pumping her hips immediately, desperate as she was having been on the edge of orgasm for several hours.

Despite the pain of the welts covering her body Sam, pumped her pussy as fast as she could despite her weariness and very soon felt her long awaited orgasm approaching.

Michael, however sensed it too and grabbed her ass cheeks to prevent her from pumping her hips. She looked at him desperately.

"Oh please, Michael!" She begged. "Please let me cum! Please!"

Sam was playing the role of the submissive and wasn't used to it. Michael merely smothered her mouth with his and rammed his tongue inside, dominating her. All she could do was whimper and groan until he relented. He soon pulled away and stared at her intently.

"Tell me, Miss Sam." He said. "What do you want?"

Drawing her cue from his intense stare Sam looked directly at one of the cameras recording proceedings.

"I want you fuck me with your monster cock so I can cum!" She gasped. "I love your monster cock! I love it! Please fuck me with it so I can cum!"

Michael grabbed her ass cheeks firmly and began to bounce her up and down on his cock, their bodies grinding together. Very soon Sam's eyes began to roll into the back of her head as her orgasm overtook her.

"AAAAAHHHHH!!" She squealed as her pussy began to convulse on his cock shaft. "Yes!! Yes!! Yes!! AAAAAHHHHH!!"

Michael then let a growl as his third orgasm of the evening hit him. He pumped his cock as far into her pussy as possible as his body stiffened, his semen going deep into her pussy. Sam could tell that, even though it was his third orgasm, it was a large amount, she could feel it dripping out of her pussy onto his balls and down onto the floor.

Michael stayed standing where he was for several minutes, stroking her sweaty welted back as his cock began to shrink but remained inside her pussy, still he dominated her with his mouth.

He soon stepped back and unbuckled her wrist cuffs and he had to hold her up the prevent her from falling to the floor. He then carried her from the bedroom into the lounge, following the plastic sheeting as usual, before entering the luxurious bathroom and showers.

Thirty minutes later an exhausted Sam was in one of her fluffy dressing gowns dozing on the sofa. She came around fully to see Michael sitting in the armchair looking at her, fully clothed ready to go home.

"So, Miss Sam." He said. "How was your evening?"

The irony wasn't lost on her as she opened her dressing gown to see all the welts covering her body, including her pussy lips and gestured with her hands.

"Well I certainly wasn't expecting this, Michael." She groaned.

"You did ask to see my wild side, Miss Sam." He said with a smile. "Don't worry. While you were sleeping I've cleaned up, put proper bedsheets on your bed for you. I've also put all the equipment back where I found it, all cleaned."

Sam didn't really know what to think. In her bedroom he had acted like a maledom. He had teased and humiliated her and inflicted punishment on her she had never experienced before. He had her in tears begging to cum and all he needed was a leather spanking crop. Yet here he now was acting like he wanted to stay on her good side by pleasing her.

Michael could sense that she was playing the events of the evening back through her mind, so he cut to the chase.

"I want to do this is on a regular basis, Miss Sam." He declared. "It'll be our little secret. I know you and Jennifer and Tam are taking turns to keep me happy while I have sex with Alex and Nathan."

Sam was once again impressed, he knew exactly what he wanted and knew his own value to the business. Sam decided to play his game.

"Okay then, Michael." She said. "You can have your way with me from time to time but you must learn to control yourself. Agreed?"

"Agreed!" He said enthusiastically.

He then put his hand in his pocket and handed her a small key. He then stepped back and dropped his jeans and underwear to show her that he had placed the ring, that kept his semen trapped, around his balls. Sam raised her eyebrows at this but said nothing.

Michael then stood up to leave.

"See you next week, Miss Sam." He said,

Sam had to follow him of course in order to lock up behind him. As he drove out of the parking lot in his brand new car Sam did some savage thinking.

"You are going to be a challenge Michael....." She said to herself.