Chris was on all fours in the middle of the room. His back straight with his head in line and looking down. He was naked as this was always expected when serving his Mistress however he wore a few accessories. Around his neck was a steel collar. The collar served two purposes, the first was that it served as a very real reminder that Chris was a slave, as soon as it was on his behaviour always seemed more subservient and compliant, not that he wasn't already. The collar had been upgraded recently from a leather collar as his Mistress liked both the look and the extra weight.
The second purpose was of course that it gave his Mistress an easy way to lead and control him, with or without a leash. Pulling her slave into position by a collar or using either his cock or balls via a chastity cage, cock ring or ball ring as it really demonstrated her control and dominance over her inferior slave.
The slaves accessories today also included leather cuffs on each of his wrists and ankles. Although they were not really needed for what she had in mind for this session, they were again an aid at keeping the slave in line, both mentally and physically. If required with one clip she could quickly bind or lock the cuffs together.
Chris wore two other accessories for today's task. Both more obvious then the collar and cuffs as she walked around the naked slave on his hands and knees. Nested within the slaves ass was a crystal plug. The slave hated anything inside his bum but the Mistress had made it clear that it would not be a limit and in fact she would train him to make it more of a norm in his submissive and slave state. She loved the crystal showing where his hole should be and knowing the penetration would be mentally pushing him further to submission as he suffered discomfort for her pleasure and entertainment.
The final accessory was the humbler, a device that held his balls tight whilst pulling them back behind his legs as he knelt. This meant the slave was unable to move without causing himself discomfort and caused his cock to be rock hard pointing down between his legs.
As his Mistress circled him, inspecting her property, she ran her fingers over his body. His hair, back, ass... and tapping the plug as her hand traced over his body before squeezing his balls. Chris let out a soft moan at both her touch, enjoying the attention and then the sudden feeling in his ass and pressure to his balls.
"Would you like to cum today slave?" Chris found answering the question hard for several reasons. His Mistress had trained him that he could never ask for an orgasm and that begging was prohibited and would be punished profusely. As a slave his role was solely for his Mistresses pleasure and entertainment and as such any orgasm would not be for his pleasure but for hers.
His training had made it clear that any response given should always be enthusiastic. A ideal mix of emotions in his tone would be of longing, a desire to please, a hint of desperation but overall enthusiasm to entertain. There was of course only one accepted response to such a question. On the surface the question sounded like his Mistress was asking what the slave wanted but Chris knew better and without hesitation responded immediately. "I seek only to please you Mistress, if that will give you some joy then I would be delighted too."
This wasn't the first time Chris had been asked the question and he knew how she carefully picked her words and how she had trained him to respond.
Chris knew that his Mistress absolutely loved to tease him. Making out that he would cum and bringing him to the edge time and time again before denying him. Chris also had noted that the question asked if he wanted to cum, not have an orgasm, and therefore expected that if his Mistress was to allow him to cum then there would be no pleasure with the orgasm ruined in some way.
Chris' suspicions were correct. As soon as he had responded he felt his Mistresses start lightly caressing and teasing his balls before her other hand reached down to sharply tug and stroke his cock pulling it both down and backwards. As she slowly stroked his cock she responded. "Good boy, what I would find most entertaining today would be to milk you, do you know what that means?"
Chris blushed profusely his blood competing between rushing to his face and his cock which was now rock hard and enjoying the attention. Chris had never been milked before. he knew exactly what it meant but decided to feign ignorance to avoid the humiliation of having to explain his understanding of what may be about to happen.
Chris' Domme knew his tricks and before chris even had a chance to wonder if he had got away with his deception he felt her hand grab hold of his balls and tighten. "Nice try boy, get talking."
Chris let out a gasp at the sudden pain and quickly started his explanation. "To milk me Miss, whilst on all fours, you will edge me and then keep me on edge squeezing and coasting all the cum out my cock and balls with no orgasm."
"Better" she said. "As this is your first milking your right I will milk you by teasing your cock until your balls run dry, but as you are trained the stimulation with be using a toy in your ass, your cock throbbing with no contact or even whilst your cock is still locked in its cage."
Whilst speaking her hand had started working his cock, expertly teasing it. Chris had only half heard what she had said, specifically that in the future she would milk him via his prostate as he was quickly distracted by the feeling of being brought to his edge. He had been kept teased and denied for weeks so it didn't take him long to reach his edge.
The way her hand worked his cock was in no way designed to give him pleasure. He could feel one hand now massaging his balls, encouraging the cum out whilst the other hand used long slow strokes to squeeze the cum from the bottom of his clock all the way up and out.
"Now slave it's clear you lied so your punishment" his Mistress started to say however the rest of the sentence was unheard as Chris drifted into sub space, even though the hand on his cock wasn't sensual or working him to orgasm, the touch felt bliss after previous teasing and then chastity. As the hand reached the end of his cock again he let out a little moan. The pleasure, albeit a teasing one, was suddenly not his main focus as he snapped back to reality paying attention to his Domme when he heard the word punishment. He quickly tried to apologise but she didn't let him speak and carried on he sentence.
"Your punishment will be." She paused. "On this occasion nothing." Chris was surprised and confused but as he felt the hand slowly squeeze his cock again his focus turned back to his cock as another moan escaped from his lips.
His Domme explained "clearly you were embarrassed by the situation so instead of punishing you I will help train you. Your milking is being recorded so to help you overcome your embarrassment you can share the video will at least 3 people and ask them for their opinions on it."
His Domme stood up and then moved a standing mirror in front of chris so he could see himself being milked as she sat back down and started working his cock again.
For the first time chris could see the full scenario. There was a bowl underneath his cock that his Domme was milking his cock into, he could see cum starting to ooze out and drip into the bowl, he could see his face full of frustration as he held the position he had been instructed to hold, head facing straight, and what's worse he could see the camera. It suddenly dawned on him that before the camera could just see his ass and cock but now with the mirror in position it could also see his face due to the reflection.
His Domme picked up the pace stroking and squeezing his cock with one hand whilst the other massaged his balls. Chris watched himself in the mirror, his eyes flickering between the slutty and humiliating facial expressions he made as his cock was teased, to the glinting light reflecting off his plug ass and then to the constant dripping of cum being extracted with no pleasure from his cock .
Every time chris heard a drip he blushed. His Domme kept her rhythm pointing out when cum leaked out or when he made what she considered to be an amusing facial expression to keep his humiliation constant until she had milked him dry.
After yet another humiliating facial expression following a needy moan chris was asked to name the animal most commonly milked. Fighting back another moan chris replied, answering in a full sentence to avoid punishment, "other than male subs, the animal to be most commonly milked would be a cow Miss".
"Good boy, she replied and what noise do they make?" Chris paused for a second whilst another moan escaped his lips followed by a drip sound as some more cum leaked into the bowl. "The noise a cow makes is a moo Miss."
She responded quickly with a very dominant tone "moo then."