A Sissy Maker Tale Pt. 09

The twice-daily training sessions were having the desired affect Alexandra was hoping for. The constant edging and anal stimulation was virtually erasing any of Adam's male psyche when he would arrive at her home.

By the third day, Adam had been conditioned to knock on the door, wait for his Mistress to tell him to come in and them immediately go to the "other" bathroom to remove all of his clothes except the panties he would be wearing that day. He would then crawl to the study and remain on his hands and knees in the middle of the room. Sometimes Mistress Alexandra would come in as soon as he did, but other times she would have him waiting for up to thirty minutes, knowing full well how painful his knees would be as a result of the wood floor.

The sessions basically consisted of the same emasculation and slow feminization that Alexandra knew were so important in the early stages of training.

Adam was constantly edged and fed his pre-cum. By the third session he was begging to be allowed to lick up his droppings knowing that this was pleasing to his Mistress. All the while he was being verbally assaulted by Alexandra, letting him know over and over again that his little clitty was of no use to any woman and that he was not a real man.

"Just look at you", she would state. " What real man would be in ladies panties and have his clitty locked up? And what real man would enjoy having his ass pussy played with so much. And what real man would moan like a sissy bitch when being finger or dildo fucked?"

These questions were constant and the extreme edging was the catalyst that soon had Adam agreeing with his Mistress. He began to realize that he would not be allowed a "man" orgasm again as long as he was "hers", and that the only sexual satisfaction would come from his boipussy being manipulated.

His clitty was now constantly leaking and he was in a state of sexual arousal all hours of the day and night. His sleep rarely consisted of more than four hours. He was required to be at his Mistress's house at five AM every morning. This would allow for at least three hours of training before he was sent home to get ready for work at nine. In the evenings, he was required to be back at his Mistress's house by eight PM and another four hours of training. By the time he was back home and in bed, it was close to one AM.

After the first two training sessions, Adam was sent home with a mantra that he was to remember and recite prior to the next and every other training session.

It stated....

"Greeting Mistress Alexandra. I am your new sissy bitch and I am here to be trained to your specifications. I am here to obey and please you. I am here, and have the honor, to be molded into a cock loving sissy that will make you proud of me and accept me as an adored pet. "No" is not in my vocabulary anymore. I await your instructions."

As Adam was reading it, Alexandra stated, "I expect you to know this verbatim by tomorrow morning. No excuses."

Adam spent most of the night go over it again and again.

Alexandra always met her bitch dressed in a dominant way. Either a short leather skirt, sometimes in only black nylons and heels with a black panty covering her pussy, or sometimes in leggings and boots. She always was topless and the site of her tits was meant to keep Adam sexually focused. Needless to say it always accomplished that goal.

On Friday night, after a particular long session of edging, anal stimulation and verbal emasculation, Alexandra let Adam know that he could sleep in on Saturday and was not required until noon. He was told this while his head was being held firmly against Alexandra's covered pussy and his nose was luxuriating in her lurid smell.

Every session would end this way, with Alexandra having a firm hold on Adam's head. As she gripped his hair and sensually ran his finger through it, she would tell him the same thing after every session.

" You know sweetie. Until I have determined that your preliminary training is complete, you will never, ever touch or taste my pussy. Only if you continue to be a good, compliant submissive bitch for me will you be allowed the privilege of serving me between my legs. Do you understand?"

Adam would answer, "Yes Mistress", as his head was planted firmly on his Mistress's loins.

Saturday morning marked one week since Adam had first met his new Mistress and had started his training. Alexandra was ready to take the next step in her process. This would include punishment exercises and teaching Adam to learn to crave her cock. For it would only be through her cock that Adam would receive sexual pleasure and hopefully, sexual relief.

Right on time Adam was knocking on the door at noon. Alexandra was ready and called for him to enter. Per his previous visits, he disrobed and was kneeling in the middle of the study. He noticed a padded leather bench that had not been there during all of his other sessions and he began to fidget at the thought of what it was there for. Laying atop the bench was a device that Adam had no clue as to its use. Unbeknownst to him the item was going to become a part of many training sessions to come.

The device as a "humbler".

Now, for the uninitiated......

"A humbler is a type of physical restraint device used in the BDSM practice of cock and ball torture. It restricts the movement of a submissive male by cuffing his testicles around the base of his scrotum. The humbler consists of a testicle cuff which is mounted at the midpoint of a bar which sits at the base of the buttocks, behind the man's thighs."

"The device gets its name because the wearer must stay in a crouched or "humble" position while wearing it to remain comfortable."

The clack of Alexandra's heels awoke Adam out of his reverie.

As she stepped in front of him, and with head bowed, he recited...

"Greeting Mistress Alexandra. I am your new sissy bitch and I am here to be trained to your specifications. I am here to obey and please you. I am here, and have the honor, to be molded into a cock loving sissy that will make you proud of me and accept me as an adored pet. "No" is not in my vocabulary anymore. I await your instructions."

"What a good gurl you are", she replied. " Up to this point you have pleased your Mistress and I have decided to continue your training. You still have a long, long way to go but I think you are making great strides. I am proud of you bitch."

With this, she patted his bowed head and Adam felt a great sense of accomplishment.

" Now stand up sweetie and let's take off your panties. There you are. Just look at the mess you made again. You know what to do."

She handed the soiled panties to Adam and he immediately licked and sucked all of his juices out of the fabric.

"What do you say sissy?"

"Thank you Mistress Alexandra."

"Well you are very welcome slut. Now get back on your hands and knees and I am going to introduce you to the humbler. This is a vital part of your next training and once in place I expect another thank you."

Alexandra grabbed the humbler off the bench and moved behind her bitch. She took the wooden device and put it in place as she grabbed Adam's little testicles, pulling them backward between his legs. By connecting both pieces of the humbler on both sides of his ball sack and then tightening the screw, the wooden pieces put pressure on the thighs and kept the sissy balls cuffed behind the sissy's ass. Adam had no idea what was going on but he was soon to find out the restriction of movement the device created.

"There we go sweetie. All done. Now that wasn't so bad. Did you forget what we talked about?"

"Thank you Mistress", Adam squeaked out.

"Now stand up for me bitch!"

Immediately meaning to obey, Adam tried rising to his feet. The pain hit him instantaneously and he fell into a crouching position.

"I said stand up you little cunt!"

Slowly this time he tried again, and again he felt the pain and realized it was useless and kneeled in pain again.

Alexandra was now laughing out loud at Adam's predicament.

Between her episodes of laughter, she was able to explain to Adam that the humbler would not allow him to stand and would keep him in a kneeling position for her whenever it was in place. The understanding made Adam cringe and a new found fear started to take hold of him.

Alexandra had now grabbed him and was pulling him by his hair over to the bench. While still on his knees, she lifted up the top of his torso and laid it across the padded bench. Adam cried out in pain as his balls were pulled further back from his body. His hands were pulled in front of him and were suddenly cuffed to the front legs of the bench. He was totally immobilized in this position and with this being his first foray into restrictive bondage, Adam was terribly frightened.

"Please Mistress Alexandra" he begged. " I don't like this. I am scared. Please let me up."

He was already on the verge of crying and Alexandra was delighted. She knew the position was painful and so fucking humiliating.

But she also knew that eventually her new little sissy would be begging to be put in this position again!

"There, there sweetie. It's okay. This is for your own good. It is time for you to understand that when you displease me, or if I feel the need, I will punish you to help you progress with your training."

Alexandra took a large ball gag and secured it tightly on Adam as she continued her dissertation.

"Now I expect you to nod if you remember what I am recollecting for you. First, in the Home Depot you didn't answer me immediately. Remember?"

Adam nodded in fear.

"Secondly, you took it upon yourself to bring a muffin and a coffee for you to enjoy with me on your first visit after we met, without my asking you to do so. Do you remember?"

Again a fearful nod of the head.

"And just today you spoke to me without being asked, begging for release from the bench. Do you remember?"

A final nod reaffirmed his remembering.

As Alexandra moved across the room she opened up a cabinet and took out, what she referred to, as her "punishment cane". She knew Adam could see her, she made sure of it. His eyes bulged out and drool was leaking out of his mouth at the site of her holding it sensually and bending it, as if testing it's worthiness.

Swishing it ever so slowly as she approached him Alexandra casually stated, " I am glad my little slut has such a good memory. It makes me certain that you will remember your first caning forever and ever. You will come to know the cane very well in the weeks and months to come. It gives me great pleasure in marking you as my new property and that my dear, should give you pleasure. Knowing you are pleasing me."

Adam was now shaking his head, in a non-verbal pleading.

Of course Alexandra totally ignored the begging for her to stop and positioned herself behind Adam. She had learned from earlier experience just how devilish the humbler was when paired with a caning. The pain from the cane would involuntarily have the submissive moving up to avoid the strikes, but the humbler would render that endeavor both hopeless and pain inducing.

Alexandra began a light, slow tapping on the right thigh and ass. From the top to the bottom she tapped away until a lovely light hue of red began to appear. She repeated this on the left side and admired her work.

During this, Adam felt the first taps and was a bit relieved that there didn't seem to be much discomfort. But as the tapping continued his backsides began to burn and he started to squirm and pant. The constant staccato of the cane tapping his skin soon had him in pain and he was happy for a brief respite.

" Are you going to be a good bitch from now on?" Alexandra yelled.

Adam frantically nodded yes.

"I didn't hear you?"

Adam muffled out a "Yes, yes, yes Mistress."

"And are you going to be my sissy cock whore for me?"

Again a muffled "Yes".

"And are you going to crave your boipussy being played with?"

"Yes, yes, yes Mistress!"

"Well then, let's get something in you to ascertain if that last answer was truthful."

Alexandra had fucked his boipussy in the training sessions with her fingers and some smaller didos. But today she was introducing the slut to a butt plug. She stepped in front of him and showed him the plug that was going in him.

"You see bitch. This is a butt plug and it is going to accessorize you just like your cock cage. You will learn to crave being plugged and today we start your butt plug training."

The plug was black and of medium size. With the humbler in place it took a bit more time, but soon the plug was inching it's way across the tight sphincter of Adam.

As the painful sensation of being plugged hit him, Adam began to moan and cry and whimpered numerous "nos" as the plug ever so slowly pushed into him. The burning seemed intolerable, and just when he thought he couldn't possibly take any more the tip of the invader pushed pass his tight hole and the thickest part of the plug stretched him to new heights.

A high-pitched scream emanated from the gagged sissy as the plug seated itself.

His Mistress was in front of him again, wiping the tears away and complimenting him on being such a good gurl. For a reason he would never understand, he tried to smile through the ball gag. Once again taking some sort of demented pride in pleasing her.

Moving behind him Alexandra put her hands on the young submissive's ass and was aroused by the warmth emanating from the skin. She moved off to the side, took aim and landed a frightful blow on the already reddened ass. Adam screamed out in pain but the blows were coming in rapid succession now. The swoosh of the cane was followed by a distinctive crack and every landing strike was followed by another ghastly scream. Alexandra was an expert at wielding the cane and every time she hit she made certain it was in a different area than the previous one. A punishment caning was not for the faint of heart and soon the poor slut's ass was striped and bloody. Uncontrollably sobbing and screaming Adam prayed for the punishment to stop. He knew at that moment that he would never willingly upset or disobey Mistress Alexandra again. And Alexandra knew the power of the cane and her administering punishment would forever be burned into the psyche of her new sissy slut.

After fifty strikes, the punishment session was over. Nonchalantly Mistress Alexandra replaced the cane in the cabinet and smiled down at the blabbering, sobbing sub before her. She bent down and looked Adam directly in his watery eyes.

"Not a single fucking sound", she whispered to him.

She unbuckled the ball gag and Adam spit out a large amount of saliva. But he remained quiet as his Mistress wiped his face and left the room, leaving him plugged and beaten, still stretched across the bench. She was in her bedroom, carefully watching him via cameras mounted throughout the study. He wiggled and moaned but soon he was crying himself to sleep. She adjusted her timer and set the alarm for sixty minutes. Once again, knowing it to be just the right amount of time to further initiate a continuance of the training session.

Alexandra herself had dozed off and was awakened by the buzzing of the timer. She readied herself and went back into the study. The clacking of her heels did not seem to wake Adam up from what was now a deep slumber. She once again went to the cabinet and this time retrieved a black leather riding crop. She took up a place behind Adam, sitting on an ottoman, and slowly began to wiggle the butt-plug that was firmly embedded in his boipussy. As she became a bit more vociferous in her handling of the plug, Adam started to wake up.

He slowly was waking up and the feeling of having the plug tickle his prostate was a new, and yes, a pleasurable feeling for him. Alexandra knew exactly what she was doing and could tell by the almost inadvertent throbbing of the slut's ass that her movements were having the desired effect. Adam's previous sobbing had turned to quiet moaning to which he was desperately trying to keep hidden from his Mistress. But it was no use. The more he felt the pressure on his p-spot, the more he moaned, reveling in the new-found pleasure. His little clitty, which had shriveled to almost nothing during his punishment, was now throbbing and leaking again, making a small puddle on the leather bench.

"Well good morning slut. Tell me how much you like what I am doing to you."

Adam knew better than not answer, so he struggled to talk. "It feels wonderful Mistress. I have never had this feeling before. Thank you so much for showing me how my boipussy can give me pleasure."

"Well sweetie, like I explained to you previously. The only way you are going to achieve any sexual release is through your ass pussy. That is why from this moment forward I am going to train and condition you to crave cock......mine and eventually others."

With that, the butt plug began to vibrate as a result of Alexandra turning on the remote setting. Adam was once again moaning and at the same moment Alexandra walked in front of him again.

How she had "readied" herself prior to leaving her bedroom was by attaching a six inch strap-on to herself. Now, standing before her sissy slut, the black phallus waved in front of his face. He was taken aback and then he also noticed the crop that was being held by his Mistress.

In the position he was in it was necessary for him to look up and actually strain his neck to see the vision before him. He understood what was going to be asked of him, or commanded of him actually, and he instinctively closed his mouth in a quasi act of defiance.

A devious smile crept across Alexandra's lips right before her crop slashed across Adam's back. Another scream was followed by more moaning and now a great look of confusion on the little slut's face. He was still moaning with delight from the vibrating butt plug even as the crop had did its damage.

"A good sissy knows how to suck cock sweetie. Of course we can do this the hard way or the easy way. Either way, you will be sucking my black dick for the next thirty minutes. So what's it going to be."

Knowing better than to speak out of turn, Adam looked up at his Goddess and opened his mouth to a cock for the first time in his life.

Alexandra took her time and instructed him carefully as to how to proceed. She soon had him licking and sucking the balls of the fake cock like a pro. As she had him continue to lick the underside of the black phallus, she turned the vibrations up a notch on the butt plug. His moaning intensified and so did his willingness to suck cock. With saliva now dripping all over the cock, Adam was now slurping the dick in and out of his mouth, all the time listening to the commands being given by his Mistress.

Alexandra was impressed with how quickly her new student was taking to sucking cock. Many times she had to admonish him for becoming overzealous and had to explain to him that giving a blow job was an art that did not need to be rushed or hurried.

After approximately twenty minutes of his oral training, Alexandra decided it was time to have the bitch try to swallow for the first time. For this part of the training, she took hold of both sides of the bitch's head and began to force the cock down her throat. This was met with an immediate gag response and a spitting up of more saliva. But Alexandra was undeterred and continued her face fucking. She lost count of how many times the slut gagged, but finally, after telling Adam how to relax and breathe when inhaling cock, the deep- throating occurred.

As Adam became more confident, Alexandra pumped the cock in and out in a slow action that soon turned into a full-on forceful face fuck. Alexandra actually got a bit too carried away and caught herself just before Adam was going into panic mode from suffocating. She pulled the cock all the way out of the well-fucked mouth and as a reward turned the vibrations up another notch.