Educating Michael

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 returns for more)

It was a Friday afternoon and Tam was serving a customer in the coffee shop when she looked up and noticed a dishevelled young man enter. He shuffled up to the counter with his hands in the pockets of his loose fitting jeans. He looked pale and gaunt and had dark rings around his eyes. He also looked as though he was about to burst into tears at any moment.

"Are you okay, honey?" Tam asked. "Can I get you something?"

The young man looked around furtively to check nobody could hear what he was about to say.

"I'm here to see Miss Sam." He said quietly.

"You?" Tam blurted. "You're Sam's noon appointment?"

The young man nodded silently.

"How old are you, honey?" Tam whispered.

"I turned nineteen last week." The young man glumly replied.

Tam then noticed the shock collar sticking out from his shirt that he was clearly trying to hide.

"Were you the young man who was here last Wednesday with Alex?" She asked.

He nodded without saying a word, looking thoroughly miserable.

"Why didn't I see you last week?" Tam asked.

"Miss Sam let me in the back way." He replied quietly.

"So you know where to go?" Tam responded.

Again he nodded and without saying a word and made his way to the corridor that led upstairs,

"For fuck's sake, Sam." She whispered to herself. "He's still a fucking child."

Michael got to the top of the stairs to find the front door of Sam's lofthouse open and slowly walked in. Sam was waiting for him in the centre of the lounge, she was wearing the same business suit when he first hit on her in the bar almost two weeks ago. He stood staring at her from the doorway and tears began falling down his cheeks.

"You lied to me, Miss Sam." He sobbed. "This ring you put around my balls stops me from cumming, when I'm close it sends a shock to them, Miss Sam!"

Before Michael left last Wednesday she had placed the experimental ring on him to see if it did indeed keep a man's semen trapped in his balls and prevent him from cumming. Judging from Michael's consternation it did actually work, which surprised her.

"Yes it does, Pet." Sam replied softly. "But its the best thing for you in the long run, Pet."

"How, Miss Sam?" He asked and sniffed.

"It saves all of your orgasms for your training sessions with me, Pet." Sam explained.

"But why, Miss Sam?" He whined. "I've been going crazy not being able to cum!"

"I know how frustrated you must be." Sam said. "But after today you will be thanking me."

She walked over to him and he towered over her, she reached up to stroke his face. He was so enthralled by her he was rooted to the spot then noticed her suit.

"Are we going somewhere, Miss Sam?" He asked.

"We aren't going anywhere, Pet." She smiled. "Now take your clothes off and turn around."

After last week Michael knew better than to argue and did as he was told, he was soon naked before her and turned around as instructed. She quickly placed cuffs

on his wrists and locked them together then turned him around and bent down.

She removed the ring that was around his balls with a small key and gently began to stroke his cock. In no time he was rock hard and she smiled up at him, then she placed cuffs on his ankles and attached them to the same spreader bar as two weeks before.

Sam stepped back and nodded, then she picked up a rubber hood from the coffee table and placed it over his head, zipping it up at the back. She then used a small padlock to keep it on, the only part of Michael's face now visible were his eyes and mouth. Then she produced a dildo gag and strap that she placed in his mouth and buckled it at the back of his head. Michael noticed that there was a type of syrup coating it that he was forced to swallow to keep his throat from drying out.

Sam then led him, breathing heavily, by his cock further into the lounge. He noticed a large curtain was drawn across the lounge and could hear movement and groans behind it. Once again there were plastic sheets covering a large portion of the floor.

Sam smiled at him and pushed a button on her mobile, the curtain began to retract to the ceiling, what Michael saw made him groan behind his gag. A man and woman were standing in the centre of the lounge fucking. The woman's wrists were attached to cuffs on the chains that went up into the ceiling, her ankles were strapped to her thighs which forced her legs open while she swung from the ceiling. The man's hands were cuffed behind him and his ankles were cuffed to a spreader bar just like his own. They were also wearing identical neck collars and the man was slowly fucking the woman's pussy. They were covered in the coconut oil that Sam seemed to prefer so much. The man had a dildo gag in his mouth but the woman was free to gasp and groan as he fucked her. Michael also noticed four cameras on tripods recording everything from each angle.

"These are my good friends, Nathan and Jennifer, Pet." Sam said. "They are husband and wife but have an open mind when it comes to sex."

Jennifer looked over at Michael and smiled between gasps as Nathan continued to fuck her slowly. Nathan, unable to speak, merely nodded.

"Have you ever had anal sex, Pet?" Sam asked him.

Michael shook his head as he continued to stare at the sight before him.

"Well, that will change today. I'll leave you to it, Pet." she said.

With that Sam turned away and left the lofthouse, closing the door behind her.

Michael was breathing heavily, standing watching Nathan and Jennifer continue their slow fucking. Jennifer looked over at him and smiled.

"Let's see what you can do with that cock of yours, shall we?" She gasped. "Don't be shy, Michael."

Michael shuffled over to her but because his cock had no lubrication on it he was unable to force it into her ass. He tried for several minutes but couldn't get the right angle and whimpered in frustration.

"Would you like some help, Michael?" A voice whispered in his ear as he felt a hand stroke his hip.

Michael snapped his head around and saw that he was face to face with Alex, he could feel Alex's erect cock pressing against his ass cheek. Alex merely smiled and Michael felt coconut oil being poured across his shoulders from a large jug that Alex was holding in his other hand. Alex immediately began rubbing the oil over his shoulders, back and ass before moving to his chest and stomach, he also began pinching his nipples. Michael began to groan and sigh as the shock of another man getting intimate with him began to wear off.

"So, do you want some help, Michael?" Alex asked again.

Michael screwed his eyes shut and nodded his head, desperate to have his first experience of anal sex.

Alex then began to massage the oil over Michael's cock with deft, tantalising fingers. Michael hissed in pleasure and threw his head back.

"You see, Michael." Alex said. "A man's fingers can be just as delicate as a woman's and you wouldn't even know it."

Alex then took a firmer grip on Michael's cock and began to position it at Jennifer's anal opening. He first rubbed the head across her anus several times which made him thrust his hips forwards.

"Now you need to be careful, Michael." Alex said. "You can't just shove your monster cock into someone's ass. You can hurt them, with anal you need to take it nice and slow so the ass you're fucking gets used to your width, understood?"

Michael took a deep breath and nodded his understanding. Meanwhile Nathan and Jennifer had stopped fucking and remained still. Alex the placed the head of Michael's cock into Jennifer's ass.

"Now push slowly, Michael." Alex instructed.

Michael did so and as the head of his cock passed Jennifer's sphincter she let out a gasp and groaned as he pushed his cock into her bowels inch by inch.

"My God!" Jennifer exclaimed. "That's one impressive cock you have there, Michael!"

Michael smiled as he pushed his cock all the way into her ass until his balls rested against her ass cheeks. Alex got him to hold there for a few minutes as Jennifer got accustomed to his size, then let him start a slow fucking motion.

"It's different fucking someone in the ass, Michael." Alex explained. "The anal muscle is a lot tighter than a pussy so the sensations on your cock are greater, especially if the person you're fucking clenches.

As if on cue Michael felt Jennifer's ass clench around the base of his cock and he let out a loud, muffled gasp. Jennifer turned around and winked at him. Michael quickly realised he was in the hands of three professionals.

Nathan and Michael then worked up a rhythm, when Nathan thrust his cock into Jennifer's pussy Michael would pull back and vice versa. It had the effect of driving Jennifer into a frenzy of genuine lust. The sensations of Michael's monster cock in her ass moved from pain to bursts of pleasure and coupled with Nathan's cock pounding her pussy, drove her wild.

"AAAAAHHHHH!!" She screamed into the air.

While Jennifer was busy being subjected to dual penetration, Alex kept himself busy by continuing to massage the oil over Michael's body. He concentrated on his ass crack and anus and slowly began to push his finger inside his puckered opening. This had the effect of forcing Michael onto his toes and groaning as much as Jennifer through the dildo gag in his mouth. Alex pushed his middle finger in right up to the knuckle and began fucking him with it.

When Alex felt that Michael's ass was dilated enough he poured coconut oil over his own cock and lined the head up with Michael's anus. He used the same method he had just shown Michael and gently pushed the head past Michael's sphincter, who threw his head back and gasped but still managed to keep fucking Jennifer's ass.

Alex then maintained a rhythm, fucking Michael's ass when he was withdrawing from Jennifer's ass, as all four of them moved towards their own individual orgasms. Jennifer's orgasm came first, she looked Nathan in the eye as her juices coated his cock and her pussy squeezed at the same time.

"OOOOOHHHHH!!" She squealed as Nathan and Michael continued their dual assault on both of her orifices.

She found the the sensation of the two cocks overwhelming and very soon Nathan was groaning as his cock flooded her pussy with his semen. She clenched her pussy muscles, milking as much cum from his cock as possible. Nathan withdrew and staggered back, his legs shaking.

Michael held off his orgasm a little longer, he was enjoying the tight fit of Jennifer's ass and as she came her anal muscles began contracting on his cock, the feeling was fantastic, just like Alex said it would be. He suddenly stiffened and groaned behind the dildo gag as his semen shot out of his cock, flooding Jennifer's ass. It was his first orgasm for ten days and Jennifer knew that the load was huge and felt the warmth of his semen coating her ass walls.

That left just Alex who was still pounding Michael's ass, taking his anal virginity, He held Michael by the throat with one hand and reached around to stroke his chest and nipples with the other. Alex soon groaned as he shot his semen into Michael's ass, coating the boy's bowels just as he had coated Jennifer's.

Alex then reached up, as the only one of the four whose hands weren't cuffed, unbuckled Michael's dildo gag. He dropped it on the floor and grabbed Michael's masked head and pulled him back and began kissing him deeply, thrusting his tongue into his mouth. Michael could do nothing but groan and whimper, the feelings of his first bisexual encounter overwhelming him on so many levels. Alex then pulled away.

"Tell me, Michael." He gasped. "Wasn't that better than a wank or a five minute fuck with silly teenage girl?"

"Oh God!! Yes, Mr Alex!! Michael breathed. "That was something else!!"

Alex, Nathan and Jennifer exchanged knowing glances while Michael closed his eyes, still in bliss at what he had just experienced. They knew that this afternoon was all about getting Michael comfortable at being naked around men and engaging in bisexual sex without being abhorred by it. Alex and Nathan knew that the erectile drugs they had taken, and the same drug that Michael didn't realise he had taken, would last for several more hours. They both knew that Jennifer's presence was necessary in order to stop Michael freaking out at having sex with two other men, they would fuck him while he was distracted fucking her and it was working like a treat.

"The afternoon has only just begun, Michael." Alex said with a smile. "That was just the warm up."

Five hours later Alex was experiencing a feeling of deja vu. He was sitting on the sofa idly chatting with Nathan and Jennifer. They had cleaned themselves up and cleared away most of the plastic sheets. However, in the centre of the lounge on the soft mats was Michael, he was laying face down, naked, and sleeping saturated in oil and the semen that all three of them had managed to produce during the session. During the afternoon Michael felt comfortable enough to ask for the rubber hood to be removed and also had several loads of Jennifer's pussy juices on his face and chest, adding to the smell of his debauchery.

The only thing missing, Alex thought, were all the bite marks and scratches that he had suffered at the hands of Andrea and her companions. Sam had insisted to the three of them that there was to be no biting or scratching of any kind, she did not want to send Michael home to his parents with his torso so obviously abused.

During the last five hours Michael had experienced everything that they could do to him in the time allowed, ranging from spit roasting him to rimming and much more. He was sleeping with a contented look on his face that Alex remembered so well after his first experiences with kinky sex. On Sam' instructions he had put the ring back around his balls, trapping them, ensuring that Michael saved his orgasms for his next visit, being so young Sam did not fully trust him yet.

The front door opened and Sam entered the lounge followed by Tam. Alex hid a smile behind his hand because he knew Tam was not going to be happy. Tam saw Michael on the floor covered in semen and looked over at them.

"For fuck's sake!" She hissed. "He's only nineteen! What have you done to him?"

Jennifer put a finger to her lips.

"Shhhhh! There's a baby sleeping!" She giggled.

"That young man has just had the afternoon of his life!" Nathan stated.

"He even asked me to take his hood off so his friends, when they see the video, know it's him!" Alex added for good measure.

Tam just stared at them indignantly but knew there was nothing she could do so she turned to Sam.

"He's too young to be doing this!" She insisted.

"That's why we're going to take it nice and slow with him." Sam replied. "There will always be one of us girls here to distract him while the boys teach him to do what the boys do."

Sam let out a deep sigh and rolled her eyes.

"Let's face it, Tam." She said. "You would love to have sex with this six foot, blond, blue-eyed boy with a big cock at some point, wouldn't you?"

At this point, Michael began to stir and they all stopped talking to look at him. He slowly opened his eyes and turned over onto his back very slowly and then sat up. He blinked several times and saw all five of them looking at him, Tam had a look of concern while the other four had warm smiles on their faces. Michael began to blush when he realised he was the only one naked and saw what he was covered in.

"EEEEEWWWWW!!" He cried. "GROSS!!"

"So, Pet." Sam said, still smiling. "How was your afternoon?"

Michael held out his arms as he looked up at her, they were covered in strands of semen, whose he wasn't sure.

"It was fantastic, Miss Sam!" He gushed. "I didn't know that sex could be that good! When can we do it again, Miss Sam?"

This brought a general round of laughter from all present, apart from Tam who rolled her eyes. Knowing perfectly well that all four of them had enticed Michael into accepting the delights of kinky sex by deceiving him with Jennifer.

"They all said they wanted my monster cock in their asses, Miss Sam!" He exclaimed. "I also came in Miss Jennifer's pussy!"

He then stopped and frowned.

"Although I'm not sure about sucking men's cocks. Miss Sam!" He said. "But I did enjoy Mr Alex rimming me!"

Michael was clearly overwhelmed by the many new experiences he had engaged in during the afternoon, that he was babbling like a small child. The others were quite happy to let him talk, except for Tam of course, who felt they were making a mistake taking on someone this young. Michael eventually looked at Sam.

"Am I here to even out the team, Miss Sam?" He asked. "Three boys and three girls?"

Sam kept smiling, but was secretly impressed by Michael's question, she said nothing however but Nathan soon spoke up.

"We boys could call ourselves 'The Three Musketeers' if you like Michael." He said. "You could be Aramis, the ladies man!"

Tam simply snorted but the rest of them remained silent until Sam spoke again.

"Right then, Pet." She said. "You know where the shower is, we can't send you home like that. So get yourself cleaned up and I'll have an uber take you."

Michael then stood up and rivulets of oil and semen began dripping from his body onto the mats as he made his way to the showers, making sure to stay on the plastic sheeting. They all silently watched him go.

"He's certainly in a better mood now than he was in the shop earlier." Tam admitted. "He was about to burst into tears."

Sam looked at her with a knowing smile.

"The art of control, Tam." She said. "Is being subtle....."