DISCLAIMER-This is a series of fan fiction, most of the characters in this series follow on from ONLINE CHASTITY by FICT which can be found in the BDSM part of Literotica. This is just my view of what paths the original characters in the original series could have taken. You should read Online Chastity chapter 1-6 to see how Alex ended up here.

(Alex has come a long way)

It was a Wednesday lunchtime as Alex parked his car in the coffee shop parking lot. He looked at the coffee shop with the lofthouse above and he could not believe that he had been coming here to ‘perform’ for over a year most Friday nights. Sam had shown him over the last year everything he had fantasised about and more and he had become pretty much devoted to her. She had led him down a path that had caused him to lose much of his shyness and inhibitions. He had gotten over his fetish for women’s clothing and had become addicted to kinky sex. He still wore the neck collar but to him it was now a fashion accessory not a training device. He was also cage free because Sam trusted him to save his semen for Friday nights.

He soon discovered that Sam made a living by streaming their performances live to paying subscribers and it was a very very lucrative company. He usually performed with Nathan and Jennifer who it turns out were happily married. It wasn’t at all times sex, sometimes they would all do photo shoots promoting numerous fetish wear, hence the reason why Sam took measurements of his body the first time he was in her lofthouse. The rubber or latex would fit him like a second skin.

It occurred to him that Sam had all this planned from the moment she drew him into her web. He accepted this however due to the fact that his cut from the revenues was very good and, as far as he was concerned, easy money. The money earned was all above board, Sam’s accountant saw to that, and was in the bank earning interest. If he kept performing for several more years he would be sitting on a very nice nest egg indeed. Sam also made sure everybody involved in her little enterprise had regular health checks.

Some of his closer friends knew about his kinky side line and wished him well, particularly when they saw how confident he had become and the fantastic sex he was having. Sam was also very meticulous with the planning, sometimes he wouldn’t be needed so he could hook up with numerous female friends knowing he could have sex and not worry about failing to perform. He regarded these breaks as mini vacations to stay fresh, not realising that this is what Sam intended for him.

Before he entered the coffee shop he paused to look at himself in the window. Due to his regular waxing sessions there wasn’t a hair on his body except his head. The breeze at all times felt cool on his body and he had learned not to be embarrassed by the looks he got from some people. It was a warm summer’s day, he was wearing shorts and a tight t-shirt that showed off his toned body. He kept himself in shape but was told by Sam not to bulk up too much, the appeal to his Fetlife fanbase were his slim, lithe sweet boy next door image. He also sported the same wavy haircut that drew Sam to his original Fetlife post.

He opened the door and quietly walked in, Tam was behind the counter as usual serving a customer. She looked over at him and smiled, said nothing, but pointed to two coffees at the end of the counter. He smiled back and nodded, the tracking device in the collar alerted her that he was coming, so the coffees were ready to go. He scooped up the coffees and made his way upstairs, he let himself in with the key that Sam had provided him with, a concession Sam afforded to very few people, but it showed she trusted him.

He closed the door quietly and walked into the lounge and saw Sam lying on her sofa with her arm across her face. She was wearing her black catsuit with high heels, this was her work outfit that she now wore when training new recruits. Her body was as curved and enticing as it was when he first saw her photos on her Fetlife page. She heard him enter and looked over at him.

“What are you doing here on a Wednesday, Alex?” She asked.

Alex said nothing but walked to the coffee table and placed the coffee in front of her, he then leaned down to give her a kiss on the cheek, which she made easier for him by turning her face, he then plopped down in the armchair facing her.

“All my clients are happy with my designs so I got the afternoon off, Miss Sam.” He replied. “Besides I spoke to Nathan the other day and he told me you had another session with a potential recruit.”

“How many times have I told you not to call me Miss Sam when we are speaking in private?” She asked.

Alex threw her the cocky lopsided grin that he had perfected, knowing that she adored his cheekiness.

“Force of habit, Miss Sam!” He exclaimed, raising his hands. “I can’t help it, Miss Sam!”

Sam let it go at that and reached for her coffee, she watched Alex as he looked at the mirror on the wall that would show who was in the playroom being trained. He had come a long way in the year since she first enticed him into her web. He retained his innocent image but at the same time literally exploded out of his shell after Tam had fucked him into oblivion during his second session. She knew at that moment that Alex was hooked on kinky, fetish sex and would be easy to control without him realising it.

Most of his clients that used his services as a graphic designer, were in fact Fetlife subscribers, who paid good money to see him perform in the playroom and elsewhere on Friday nights. They were advised of his services by Sam herself so that she could keep an eye on him without making it look obvious.

She was also aware that he had made a copy of the key hanging on the hook by the front door that unlocked his collar. She chose to keep all this to herself of course and let Alex think he was being smart. He had, so far, never failed to perform for her and she knew he worshipped the ground she walked on, despite his cheekiness. He had clearly become something of a hedonist but had worked out as a valuable member of the team, something she was very happy about.

“How is the new mirror working out, Miss Sam?” He asked.

She looked over at the mirror on the wall, the blind had been removed but the mirror had been replaced with an updated version that she could control from her mobile. At the touch of a button she could reverse the view that meant she could see through one side but the person on the other side only saw a reflection of themselves.

“It’s working fine at the moment.” She replied. “Would you like a demonstration?” She asked.

Alex nodded so she pushed a button to reveal what was going on in the playroom. Alex whistled at what he saw. On the platform was a young man, naked, he was standing spread eagled with his arms cuffed to the ceiling and his feet bolted to the floor two feet aside. He was six feet tall with a swimmer’s create similar to Alex and the same wavy hair cut. He wore an identical neck collar and his body had been oiled from head to toe that made his muscles more defined. Like Alex he didn’t have a single hair on his body except his head, he was breathing heavily and standing in front of the silicone pussy that Alex remembered so well, but what drew Alex’s attention was the size of the erect cock that was embedded in the pussy. He turned to Sam.

“That must be well over nine inches, Miss Sam!” He exclaimed.

“Nine point four inches to be exact.” She said smugly. “If he passes his training, do you think you’ll be able to handle all that cock, Pet?”

She emphasised the word ‘pet’ to ensure she had Alex’s attention. She hadn’t referred to him as ‘pet’ for a while and she knew she still had the ability to shock him, despite his confident demeanour. Alex swiftly regained his composure and turned back to the mirror.

“I’ll do anything to please you, Miss Sam.” He replied. “You know that.”

“I often wonder what happened to the shy boy who entered my lair over a year ago.” She laughed.

“That boy is long gone, Miss Sam.” Alex said with a smile. “You corrupted him and turned him into the man before you, Miss Sam!”

Sam merely smiled as Alex looked closer and noticed there was a block of wood behind the young man, level with his ass. The block was attached to a stand that was bolted to the floor and there was a strip of metal on the side closest to his ass. This was something he hadn’t seen before and he turned to look at Sam.

“I’ve had to improvise with this one.” She said and gestured to the young man. “His name is Michael and all he wants is to fuck me with his big cock. I’m looking to channel his libido into a more exciting and controlling direction for him.”

“He looks very young, Miss Sam.” Alex said. “How old is he?”

“He has just tuned nineteen and is fresh from high school looking to broaden his horizons.” Sam replied. “Would you like to see how the block behind him works?”

Alex couldn’t take his eyes of the lad and just nodded. Sam pushed a button on her mobile and spoke into it.

“Break time is over, Pet.” She said. “Start again and tell me when you are close to cumming. Understood?”

Michael looked around at the metal block behind his ass but did not move. Sam let out a deep sigh and pushed a different button on her mobile. Michael jumped and twisted his neck from side to side, Alex knew that Sam had shocked him via the neck collar. He still didn’t move so she shocked him again causing him to jump again. He took a deep breath and slowly began to draw his hips backwards until his ass touched the metal plate on the wooden block, appearing relieved, he took another deep breath and began thrusting his large cock into the pussy very slowly.

“Now, Pet.” Sam said. “If you want to fuck me you must learn to obey without delay, Do you understand?”

“Y-y-y-y-yes, Miss Sam!” He gasped between breaths. “S-s-s-s-sorry, Miss Sam!”

Alex turned around to look at Sam with raised eyebrows.

“The metal plate attached to the block can be electrified whenever I choose.” She said and waved her phone.

Alex shook his head and couldn’t help but marvel at Sam’s ingenuity when dealing with different young lads with different fantasies.

“This is his second session up here.” She went on. “He shows glimpses of promise and it would be such a shame to see that cock of his go to waste.”

Alex said nothing but knew that Sam was viewing Michael from a company perspective, much like she did with him a year ago. He himself had come to terms with what Sam did to him, simply because the money he was earning was good and the sex was out of this world. He also understood the subterfuge Nathan and Jennifer played on him and how it was necessary to draw him in to their world of kinky sex. He stood watching Michael fuck the pussy for a few minutes until his breathing became ragged.

“I’m g-g-g-getting close, Miss Sam!” He gasped. “I’m getting close, Miss Sam!”

“Very good, Pet.” Sam cooed into her mobile. “Very good, Now stop and rest again. Understood?”

Y-y-y-y-yes, Miss Sam!” He gasped, his chest heaving.

Sam noticed he stopped immediately with his cock fully embedded in the pussy. He now knew that Sam had activated the metal plate behind his ass and knew he was in for a nasty shock if he continued thrusting his hips.

“That’s very good, Pet.” Sam said. “You obeyed immediately that time, well done. You do want to fuck me with that marvellous cock of yours, don’t you, Pet?”

“A-a-a-a-absolutely, Miss Sam!” He gasped.

Alex couldn’t help but smile because he remembered Sam using almost the exact same methods to get him to obey her. They stood looking at Michael as he breathed deeply, unable to move, when Sam suddenly spoke up.

“It’s a good thing you’re here Alex. I’ve just had an idea.” Sam said. “Go and get two dining chairs and put them in front of the mirror would you, please? Then get naked.”

Alex knew Sam well enough to know where this was going so he got the chairs and stripped naked as asked. Alex sat down and began stroking his cock to get hard. His posture in the chair was somewhat laid back, his legs apart and he placed one arm on the back of Sam’s chair. Sam then unzipped the crotch of her catsuit and sat down but crossed her legs, she held her mobile in one hand and began stroking the back of Alex’s neck with the other.

“Now.” She said. “He’s probably gonna freak out when he sees you so just play along. You might also need to improvise.”

Alex nodded as Sam pushed a button on her mobile that enabled Michael so see into the lounge. Michael’s shock was clear as his eyes went wide.

“Oh shit!” He exclaimed.

He immediately began to withdraw his cock from the silicone pussy, only to get his ass shocked. He let out a scream and pushed his cock back in and a large amount of precum began to ooze from his cockhead and drop to the floor. He then began to pull on the cuffs holding his arms above his head as well as trying to free his feet from the bolts attached to the floor.

“Nooooo, Miss Sam!!” He screamed. “Please, Miss Sam!! I don’t want another man to see me like this, Miss Sam!! Please, Miss Sam!!”

His struggles then intensified as he desperately tried to free himself from his bondage. After several minutes he realised that his efforts were futile so he rested his chin on his chest, closed his eyes and began to sob. Sam watched impassively while Alex continued to stroke his cock to keep it hard. This was Sam’s show so he knew better than to say anything. They both watched Michael for a few minutes until Sam spoke up.

“Look at me. Pet.” Sam said into her mobile. When Michael failed to respond she repeated herself. “Look at me, Pet.”

Michael opened his eyes and looked at Sam with tears streaming down his face and glanced at Alex as he calmly stroked his cock. Sam gestured towards Alex as she continued to stroke the back of his neck.

“This is my good friend Alex, Pet.” She said. “He was in your position once, feeling humiliated at being naked and horny in front of strangers. But look at him now, after training with me he soon lost his inhibitions and began to let his feelings show. As you can see, he has a wonderful physique like you and is not afraid to flaunt it to anybody. Yes, Pet, he is the nice boy I told you about when we first met.”

“B-b-b-b-but I’m not gay, Miss Sam!!” Michael sobbed and looked at Alex with a wide eyed stare. Alex remained impassive and did not react to the fact that Sam had been discussing things about him with Michael.

Sam laughed gently, the sort of laugh that she used when she was trying to entice young men to do what she wanted.

“Neither is he!” She replied. “A man’s body can be just as gorgeous as a woman’s, Pet, and men know what sends other men wild. They don’t at all times have to be gay. We could explore that with you at a later date. Would you like to see what rewards Alex gets for being a good boy?”

Michael merely nodded and sniffed as he still sobbed. Sam uncrossed her legs to show Michael her shaved pussy. Michael gasped in shock and stared at it intently. She then glanced at Alex who was on his knees in front of her in a flash and immediately began licking at her pussy. Alex was very experienced at this now and knew what Sam liked. He licked her pussy from top to bottom at first then swirled his tongue around in circles. He would then suck on her pink folds and pull at them with his mouth. While doing this he used his thumb to rub the top of her clit. He would then tongue fuck her which made her gasp. Alex continued this for several minutes as Sam’s breathing became heavier and her pussy became more and more wet. He would ease of slightly so she didn’t cum too quickly, when Sam decided she wanted to cum she would stroke the back of Alex’s neck more forcefully. Very soon she began drawing deeper and deeper breaths, so Alex moved back so Michael could see her pussy. Sam let out a loud gasp as her pussy juices squirted out and landed on Alex’s face, neck and chest.

In his bondage Michael began to shake with arousal and his cock oozed more and more precum in very impressive quantities. Alex looked around at him and began to rub Sam’s juices all over his chest and stomach. His torso now shone like Michaels, he then licked his fingers clean.

“Miss Sam’s pussy juices taste like nectar from heaven, Michael.” He said.

Alex then use his fingers to open up Sam’s pussy lips so Michael could see the wet inner folds and pointed.

“Your impressive cock will love it in there.” He declared. “Mine does!”

Alex then stood up and stroked his cock to ensure he was rock hard and pushed the head into Sam’s pussy. Sam gasped in obvious pleasure as Alex fucked her with a slow tempo.

“If you follow Miss Sam’s instructions.” Alex said. “This could be you. This is what you want isn’t it?” He asked.

“Oh god, Mr Alex!” Michael groaned. “It’s what I want more than anything!”

“Then you need to obey Miss Sam.” Alex explained. “With patience and experience your cock will enjoy what mine is enjoying. But it is something you must earn. Do you find out?”

It didn’t escape Alex’s notice that he was now doing to Michael what Nathan and Jennifer did to him, drawing a hesitant lad into Sam’s world of kinky sex.

“Yes, Mr Alex.” Michael eventually replied. “I find out.”

Sam then pushed a button on her mobile that hid them from Michael’s view and spoke into it.

“Now then, Pet.” She said. “Alex and I have put on show for you, now it is your turn. I want you to fuck the pussy very slowly and cum for us. You must learn to control yourself if wish to experience what Alex has just experienced. Start.”

Alex withdrew his cock from Sam’s pussy knowing he had to save his orgasm for Friday night and sat down in the dining chair. He continued to stroke it to keep it erect in case Sam allowed Michael to see through the mirror again. They both watched Michael as he began to thrust his prodigious cock into the pussy. Alex never tired of watching a man, spread eagled, only able to move his hips backwards and forwards because it brought back so many memories for him. It only felt like yesterday that he was in Michael’s position and some part of him was envious. After only a few minutes of slow fucking Michael began breathing deeply again as his orgasm approached and Alex could see he was making an effort not to speed up. Michael looked down at his cock intently then threw his head back.

“I’m cumming, Miss Sam!” He said unnecessarily. “I’m cumming, Miss Sam!”

He stopped moving as his orgasm overtook him and he shot a large quantity of semen against the mirror that came out of his cock in thick torrents that only younger men were really capable of. He leant back and screamed out in satisfaction, his chest heaving as he gulped air into his lungs. As he began to settle Sam spoke into her phone.

“Well done, Pet.” She said. “That was excellent, well done. You have a short rest now, you still have three hours of your session to go.”

Michael whimpered but nodded and Sam pushed the button on her mobile that turned the glass into a mirror again and Michael disappeared frim view. She then turned to Alex.

“That was inspiring, Alex.” She said. “Thank you, I think we might have just turned the corner with him. It’s still gonna take a bit of work before he is fully ready though. We need to get him okay with the idea of fucking other men without freaking out. As well as being prepared to take it up the ass.”

“Your welcome, Miss Sam.” Alex replied. “I was happy to help but good luck trying to get him to give head, Miss Sam!” He laughed.

Sam smiled her amused smile when Alex flashed his cheekiness her way but as usual let it go. He was a good earner for her enterprise and he knew it. She was just happy he hadn’t let it go to his head. He began to get dressed but didn’t, however, put his t-shirt on, his chest and stomach still glistened with her pussy juices.