A Sissy Maker Tale Pt. 10

Alexandra sent Adam home following her foot massage and nap. She released him from the humbler and told him that she expected to see him the next morning at 11am sharp. She realized that the poor boi was overwhelmed with what had transpired the last four of five hours and that he needed time to fully comprehend what was happening to him. There was only so much a new submissive could take during training and Alexandra was well aware that Adam was at his limit.

As he drove home with his panties on, still caged and now plugged, Adam began to silently cry. His ass was still on fire from the caning he had received and he was now wondering how he could possibly survive with his boipussy being filled per his Mistress's instructions. As he sat and squirmed, the butt plug was a constant reminder of his current situation.

Adam was deep in thought.........

"Why do I keep going back?"

"Why am I so enamored by Mistress Alexandra?"

"Even after such a severe punishment session, why am I still leaking in my cage?"

"Why does feeling so femme seem right to me?"

"Why was I excited when sucking Mistress Alexandra's cock?"

So many thoughts were bouncing around in his brain. He was quite confused by it all, but somehow felt at ease with the somewhat ridiculous circumstances that had placed him in his current condition.

As he parked the car and wiggled upstairs to his townhome, he suddenly had a strong desire to look at his ravaged backside and also the plug that lay embedded in him. He literally tore of his "man" clothes and rushed over to the mirror. Turning around, he got the first glimpse of Alexandra's work. His ass was a mess, stripped, reddened and in some areas still oozing some spots of blood.

Ever so gently he pulled his cheeks apart and got a good look at the end of the pink- jeweled butt plug sitting firmly in his boipussy. Without pausing, his hands went immediately to his caged clitty and he began to rub whatever area he could to find some sort of pleasure. He was then reminded of his Mistress's edict that all his sexual pleasure in the future would come from his boipussy being used. Instinctively he pulled his hands away and felt a feeling of shame wash over him, knowing that Mistress Alexandra would not be happy with him manipulating his private parts.

If Alexandra had known at that moment what had just occurred with her new slut she would have been tickled to no end. Her training was indeed beginning to take hold and Adam was already constantly thinking of making her happy and not disobeying her!

It was nearing the end of the first week of training and Adam was totally famished. After admiring himself in the mirror, he decided a shower was in order, so he took a long, hot shower, being very careful not to let the spray hit his ass directly. He knew he would be sleeping on his stomach and that the reminder of his punishment would remain with him for at least a few more days.

Surprisingly Adam slept fitfully and woke up well-rested. He made himself a cup of coffee and watched some of the Sunday morning news shows. As was normally the case after his cup of coffee in the morning, Adam headed off to the bathroom to take his morning shit. And then it dawned on him.

He had become so accustomed to the plug in his ass that he had totally forgotten it was still shoved inside of him. His mind was racing suddenly because he was in a bit of a quandary. Did he take the plug out without asking his Mistress, or did he risk waking her up by asking permission? He remembered her discussion regarding controlling his bodily actions, but did that mean now?

"Fuck! Fuck! Fuck!" he whispered to himself.

Waiting any longer certainly was not an option, so Adam decided to text his Mistress.

" Good morning Goddess. I hope I am not waking you but I didn't know what else to do. You see, I am ready to, um, well I need to vacate myself and I am still plugged per your wishes. May I please be allowed to remove the butt plug so I can go to the bathroom?"

Alexandra was already up and doing some stretching exercises when she heard the familiar ding of her phone. Reaching over she grabbed it and read the text.

As she read it, she began laughing. The little slut was still plugged for her and now he was no doubt becoming very uncomfortable waiting for a response. The notion that he was already asking her permission to take a shit was very reassuring. She was already planning a training session to show the bitch how to clean her boipussy every day. The speed in which Adam was accepting his new role was a welcome surprise to Alexandra. She couldn't wait to get her hands on him in a few hours.

Alexandra responded.

"Well good morning sissy. I trust you slept well in your panties, cock cage and butt plug. Did you think of your Mistress throughout the night? Go ahead and remove the butt plug and do what needs to be done. Make sure you shower and clean yourself inside and out for me. Following your shower, reinsert the butt plug. I know you will be feeling a bit empty after removing the plug so plugging yourself once again will bring a new found sense of contentment to my new sweet sissy. I will see you in a few hours. Don't forget, "Tardiness equals punishment!"

Adam was thrilled when his Mistress responded. He literally ran to the toilet, sat down and attempted to remove the plug. His ass was still very tender from the beating he had received the previous day so sitting was a bit precarious. He was glad he had taken some time last night to Google "butt plugs" and had an idea as to how to make removal a bit easier. So slowly he twisted the invader and pushed out like he was dropping a deuce. Eventually the plug plopped out with a rush and Adam immediately was emptying his bowels into the toilet.

Feeling like he had accomplished something that was entirely new to him, Adam smiled and knew that the plug would become part of him just like the cock cage had. Rather than shudder at the thought, it actually excited him to the point where he could feel his pre-cum dribbling over his tiny balls and he once again ran his fingers over his testicles and lapped up all the pre-cum he could.

Once in the shower, Adam danced around the spray so as not to feel the sting on his backside. He really had no idea as to what he needed to do to clean his insides as his Mistress had mentioned. So he grabbed the shower head and positioned it so that it was squirting up his boipussy, an action that was once again somewhat pleasurable for him.

Occasionally he would stop himself and try to come to terms with all the newly formed desires and feelings that his new Mistress was instilling in him. Did he really want to become a sissy for her? He didn't have an answer for that, but he did know that she was becoming very similar like a drug to him and the intoxicating effects were wonderful. His lips formed a wry smile as he continued to prepare himself for another visit to Mistress Alexandra.

As Adam was finishing drying off, he realized that he didn't have what one would consider to be a proper lubricant for the reinsertion of the butt plug. He finally decided on a moisturizing cream left over from his previous wife. He had already cleaned and dried the jeweled plug and so he used the cream to coat the anal toy and also took some on his fingers and pushed two digits into his rectum. When he felt he was ready, he bent at the waist and spread his legs while holding the plug in his hand. He began pushing and the toy slowly began to widen his sphincter. He was breathing a bit harder and he felt a burning but he was determined to get himself fully plugged for his Goddess. He pulled the toy out, added more lubricant and then gave it another try. This time the burning was minimal and with a motion that startled him the plug was swallowed up into his wanton boipussy. He once again felt that feeling of fullness and sighed with relief with the knowledge that he could remove and also put the plug back in himself as was required and necessary of him.

He decided on a bright pink lacy pair of panties, a pair of faded jeans, a tight t-shirt and some tennis shoes. He took more time than usual combing his hair and made sure to shave very closely, although he barely had what one would consider to be masculine facial hair. With one final check he felt he was ready to submit to his Mistress again.

Alexandra heard the knock on the door and shouted from her kitchen. " Come in sissy and prepare yourself. I will meet you in the study."

She checked her watch and the bitch was right on time. 'Good slut" she thought to herself.

Alexandra was really looking forward to this session. She would be further emasculating the little bitch and teaching him to connect pleasure with cock. At all times during the next few months of training she would be wearing a strap-on and of course the sissy would never be allowed pussy. Only after she was thoroughly convinced that she had turned him into a cock loving slut would she then teach him how to orally satisfy a woman. This was necessary because a sissy was to always be trained in the finer arts of giving pleasure to both women and men. But what defines a sissy is their wanton desire for cock, all the time, 24/7.

Her new sissy was kneeling as per her instructions, no doubt concerned about the leather bench with the humbler sitting on top of it. Leaning against the wall was Mistress's cane. The cane would become a vital part of Adam's training and it, like her strap-on would be a part of every upcoming session.

"Oh what do we have here? It looks like my new submissive gurl is waiting for her Mistress."

Adam took note Mistress was using feminine phrases when talking with him.

"Stand up and turn around bitch."

Adam got off his knees, stood up and did as he was told. The sight of his sexy Mistress took his breath away. She was wearing tight, black spandex pants that left no imagination as to the voluptuous body encased within. A black strap-on hung lewdly from her hips, swinging ever so gently back and forth. Impossibly high-heeled black stilettos adorned her feet and a thin, white lace top that seemed to accentuate her perfect breasts rather than hide them hung loosely on her torso. Her hair was pulled back into a tight ponytail and her makeup was as sultry as ever.

Alexandra looked at her nervous student and began a slow inspection, casually circling Adam like he was her prey and looking him up and down.

She produced a small key and simply stated, " Let's take this cage off and give you some relief."

Adam sighed as the tight cage was unlocked and his little clitty was once again free.

"Holy shit!" Alexandra exclaimed. "You call that a cock? There is no way that tiny thing could ever please anyone. No wonder your wife cheated on you. Just look at that thing. If you ever refer to it as anything but a clitty again I will cane you mercilessly. Now don't you dare move!"

Out of nowhere Alexandra had produced a small, leather penis whip. She held it up for Adam to see and then continued berating him.

"I am going to strike that clitty with this whip, and after every blow you will repeat the saying, "I no longer am a man. I am a sissy and have a clitty." Nod your head if you understand me bitch."

Adam nodded and stood perfectly still. He was so petrified he dare not move.

Crack!

"I no longer am a man. I am a sissy and have a clitty."

Crack!

"I no longer am a man. I am a sissy and have a clitty."

Crack!

"I no longer am a man. I am a sissy and have a clitty."

This went on for ten times. By the tenth blow Adam was crying but still was repeating the mantra.

"On your knees sissy. Put this cock in your mouth and give your Mistress pleasure!"

Adam sank to his knees and, having learned from yesterday's session, began to orally lick and suck the fake black dick. As he was doing this, Alexandra had moved her heels next to his little clitty and she was rubbing him as he sucked her. His clitty was as hard as he could ever remember and the more he sucked the more his Mistress rubbed against his private parts. Adam was sucking and lapping at the phallus with great abandon, trying to be a good cocksucker for Mistress Alexandra.

"Keep sucking me bitch and you better not even think of cumming. That's a good gurl. Now hold still while your Mistress throat fucks you!"

Alexandra had grabbed both sides of the sissy's head and held firm as she pushed the cock deeper and deeper into Adams mouth. The look of panic, which she had seen so many times before on newbies was always exhilarating. As she pushed into his throat the gagging started immediately. She would pull out just enough for the little slut to get a gulp of air, and then force the cock back in. Tears and saliva were everywhere as she continued. As she face-fucked him, Alexandra made sure that her heels were always manipulating the sissy's clitty. The more of the strap-on Adam took, the more she would work her heels over the slut's clitty.

It took nearly thirty minutes for Adam to finally get in the rhythm of sucking and taking the dick deep into his throat. Alexandra knew that she didn't want to overdue the cock sucking training, so after approximately forty five minutes of having Adam suck her black phallus, she withdrew the cock and patted Adam on the head, telling him what a good gurl he had been.

After sliding the strap-on out of his mouth, Alexandra told him to stand up as she walked over to the cabinet and grabbed a black dildo, nearly the same size of the cock she had been mouth fucking him with.

"Open your mouth sissy. Now take this penis and suck it like I have been showing you. Every deep throat will result in a special treat. Now suck sissy!"

Adam opened wide and the phallus slipped into his saliva covered mouth. He needed both hands to hold onto the invader as he began his oral ministrations. Much to his shock Mistress Alexandra had knelt down in front of him and took his little clitty in her mouth. The more he swallowed, the more his Mistress sucked and played with him.

Alexandra admonished him again about not cumming as she continued to give him pleasure. She knew that she was beginning her quest to have her new sissy start to feel that sucking cock would result in a pleasurable feeling. This was critical in her training process.

Over and over again, every time the slut would suck cock for her, Alexandra would make sure some sort of pleasure would be administered. This was the definition of operant conditioning.... "associating a voluntary behavior and a consequence. In operant conditioning, the learner is also rewarded with incentives." For example, the better Adam learned to suck cock, the better the pleasure would be given by his Mistress. And as always, pleasure would always be associated with cock sucking and/or a boipussy fucking.

Adam was now enthusiastically deep-throating the black dick. The soon-to-be sissy was slurping and lapping like a pro.

Alexandra continued fellating him and also giving him words of encouragement as he continued on becoming an expert cock sucker. Occasionally she would grab a nipple and pinch and twist it, giving the bitch another bolt of pleasure.

Many times during this session she had to grab the base of his tiny penis and squeeze hard to keep him from cumming. She was quite adept at this and understood how crucial it was for her to not allow any "manly" orgasms.

The sensory overload had Adam completely entrenched in his cock sucking. Nothing else mattered for him at that time other than making sure he swallowed like a whore and moaned with vigor as he handled the dildo in and out of his mouth. He had seemingly built up a tolerance to gagging, quickly learning how to breathe and deep throat. He was such a proud submissive as he was orally trained by his beautiful Mistress.

And much to Adam's shock he was soon wondering what a real black cock would feel like. "Holy shit," he thought. "What am I turning into?"

She had seen it many times before in an Alpha male. Hidden or subconscious desires that, with her expertise, become unlocked and allowed to flourish. The speed at which Adam was embracing the many feminine actions she was putting him through was a clear indication to her that he indeed was one of these Alphas who was suddenly finding the ability to let down his self-defense mechanisms and allow his deviant desires to come forth with abandon. The power which she wielded once again brought her ever so close to an orgasm of her own. God this was so exciting she thought, seeing the slow sissy metamorphosis!

She had been edging Adam for about forty five minutes and she knew he was ready to disobey her and erupt.

"Keep sucking that cock you little bitch. Don't stop or the cane will be used again!"

Alexandra got up off her knees, stretched her muscles and headed for the kitchen where she gathered up a bowl of ice. Returning to her slut, she took the tiny clitty and submerged it between the ice cubes. The sudden coldness shocked Adam to the point wherein he almost dropped the black phallus out of his mouth, but luckily for him he regained his composure and kept sucking.

Soon what could be generously called a hard-on deflated and Alexandra locked up her bitch's clitty in the cage once again. It was time to continue with conditioning Adam to associate pleasure with not only cock sucking but also from having his sissy ass fucked long and hard.

" Turn around sissy and bend over for your Mistress. You can put two hands on the desk there for support. Now stay put and don't move. Mistress has a new surprise for you."

Adam sensed his Mistress leaving the room once again and he waited, still sucking the cock, for her to return.

"Okay bitch, turn around."

His Mistress had returned and her voice startled him from his enjoying the rubber cock in his mouth. He turned around and his Goddess stood before him holding a pair of black stilettos surprisingly similar to the ones she was wearing. He noticed one difference being the small padlocks that dangled from the high heel straps.

She smiled at him and stated, "A sissy bitch always, and I mean always needs to be in heels when getting fucked in its boipussy. Now let's get these on you and have a look as to how slutty my sweet bitch will look. Now lift your foot for me. That's a good gurl, now the other one."

Alexandra adjusted the straps and locked the five inch heels in place. She could see that the slut was a bit wobbly standing, which of course was to be expected.

"Now stand in place for me and get used to the feel of these lovely heels that your Mistress bought for you. Soon we will be teaching you how to strut your stuff in them, but for the time being we only need you to turn around again, grasp the edge of the desk and wait for me to take you. Do you think it is time for you to feel my big black strap-on in your boipussy?"

The hesitation by Adam earned him a quick slap on his still sore butt cheeks.

"Yes Mistress," he squeaked.

"Good sissy. Now bend over and spread your legs for me. We need to unplug you so we can end your virginity. Keep in mind that being able to take cock is a vital part of your new persona. You will learn to crave a good pussy fucking by the time our training continues in the weeks and months ahead. Now let me just pull this plug out of you."

Removing the plug took a little doing, what with Adam using a moisturizer as a lubricant earlier when he plugged himself. As she twisted and pulled, the invader finally plopped out and it was met with a high-pitched scream form her bitch.

"Stop your whining and keep sucking that dick. I better see some deep throat action taking place again. Come on now cocksucker, get back to sucking."

As Adam followed her commands, Alexandra lubed up the strap-on and put the tip against the sissy's little puckered hole.