A Sissy Maker Tale Pt. 10

His ass had been stretched by the wearing of the plug, but the black cock was much bigger than the butt plug. Adam felt the tip push against him and slowly push into his opening. It felt so big but he wanted to take it to please Mistress Alexandra. He tried to relax as he kept sucking the cock in his mouth. He began to moan as the cock pushed past his tight hole and slowly entered him. He was thankful his Mistress was being somewhat gentle and not forcing the big cock into him suddenly. Inadvertently, or maybe instinctively, the little slut actually began to push back against the strap-on as it disappeared into his virgin backside.

Of course Alexandra noticed this and verbally complimented Adam for being such a good slut. His clitty was leaking profusely as his Mistress began to get into the rhythm of fucking him. Soon she was balls deep in her new slut, pounding away with abandon and listening to the constant moaning emanating from the sissy. She had both hands on his hips as she thrust forward and would push him into the desk as she expertly slid the lubricated cock back out of his boipussy, just to the point where the head was about to leave the tight fuck hole. Adam would shake and gasp every time this occurred and was now himself taking the black dildo in his mouth all the way down to its balls, lost in the seemingly endless scene of depravity.

There is something to be said for the changes that occur to a once masculine being who surrenders himself to a powerful Domme and allows her cock to take him. Whatever self-esteem was present as an alpha male is tossed aside and the poor slut slowly comes to the realization that what he once thought were important traits in a virile male are now to be replaced by feminine ones. Regaining any self-esteem will come at the hands of his Mistress as she molds him into a new cock loving sissy slut. It is this new found understanding that makes every compliment, as well as every reprimand, so important to the new sissy. And it is why, with such intense training, the sissy does everything in its power to pleasure others for the satisfaction of the Mistress or Master. A sissy, not being a man or a woman, has a definitive set of boundaries and behaviors that set it apart from the norm. By totally embracing these specific features a once masculine male will flourish as a proper, well-trained sissy.

Alexandra understood how important is was to dissolve any vestiges of self-esteem Adam might still have. So she constantly was verbally demeaning him, letting him know that she would never, ever let his little clitty near her pussy and that there was no way Adam could ever satisfy a woman with that tiny appendage.

As she fucked him for the first time Alexandra was whispering these very thoughts into his ears. Over and over the fucking and verbal assault continued until Adam was so incredibly broken that he was crying with tears of joy. A joy that emanated from him, for the first time in his life, feeling completely at ease with an acceptance of his fate. The bursting of his self-defense dam so to speak had suddenly allowed his once hidden desires to be used as a submissive to burst forward with the subjugation at the hands of Alexandra. He was rapidly falling in love with his new Goddess and was willing to go to any lengths to please her!

As Alexandra's strap-on continued to piston in and out of Adam's boipussy, she would occasionally reach around and pinch his nipples. She knew that a sissy's breasts and nipples were to become extremely sensitive erogenous zones thorough training to the point where a mere twist or pinch would put the bitch into a state of sexual frenzy. So a constant manipulation of this area was paramount in the twice-daily training sessions. She would eventually be introducing nipple clamps into the regimen as well as some nipple enlarging implements. But for now her tweaking was having the desired effect on her new slut.

The fucking of Adam was to go on for forty five minutes...an inordinate amount of time to anally abuse someone.

Alexandra always was a figure of health, maintaining her physical prowess through daily strength and stretching exercises. This was important in order for her to maintain her schedule of training and stick to the allotted time she deemed necessary to properly train a new sissy. So as the never-ending fucking continued she never lost a beat.

Adam on the other hand was a completely different story all together. He was struggling after the first fifteen minutes to remain upright in his high heels. His cute, hairless legs were shaking as he was being taken so skillfully by Alexandra. If it wasn't for the extreme degree of wanton desire and pleasure Alexandra was squeezing out of him, Adam would have collapsed halfway through this boipussy fucking session. He was sweating profusely and continually steadying himself on the edge of the desk. Twice during the fucking his Mistress had removed the cock from his ass completely to apply more lubricant. Each time she did this, Adam felt a sudden emptiness and missed the feeling of having something in his pussy. His now gaping hole would actually wiggle with desire hoping that the cock would return to its previous inserted position. He truly was exhibiting many properties of a wanton slut without even realizing it.

With approximately five minutes left in this part of the training session, Alexandra instructed the sissy to remove the cock from its mouth.

As she continued her onslaught, she whispered to him....

"Now my little bitch. You need to tell me how much of a perfect sissy you are going to become for me. Let's hear it cunt."

Adam replied through his sore, saliva soaked mouth. Babbling and crying the words burst forth.

"Oh God Sweet Mistress. I will do anything to become a perfect sissy for you. Anything! Anything! Please allow me to be used by you for your pleasure. You are taking me to places that I once thought only dwelt in fantasies. I am yours. I know I belong to you only now. Never have I felt so strongly about something. Please, please Mistress Alexandra train me to be the perfect sissy you require."

As she slowed her fucking motion, Alexandra smiled, knowing her training was coming along nicely. She slowly removed the cock from Adam's boipussy and told him to stay still. reaching once again into the cabinet she removed a much larger butt plug that was going to replace where her strap-on had just been. The circumference was larger than her cock so the sissy would certainly feel more stretched as it was pushed in.

"Take both hands and spread your pussy wide for me bitch. It's time to fill you up again."

As soon as Adam released his hands from the edge of the desk he plopped forward with his body unable to remain upright. He took both hands and pulled his cheeks apart for his Mistress.

Alexandra loved this image before her and quickly grabbed her phone to take a few snapshots of her new sissy and his ravaged backside. Once done, she lubed up the larger plug and pushed it into Adam's gaping hole. The bitch let out a squeal as the biggest part of the toy entered through his sphincter. Alexandra patted him on the head and mussed his hair back and forth in a movement that signified she was pleased with him.

"On your knees again now slut. We still have some training left for you and your useless caged clitty and that cock sucking mouth of yours."

As Adam was getting into position, Alexandra had retrieved an o-ring gag and held it up for him to see.

"Open up that mouth for me sissy. Here we go. Ahh yes, look how it keeps my little slut's hungry mouth wide open."

The gag was firmly buckled into place and Alexandra moved into position with her cock dripping with lubrication and whatever remnants of the sissy's boipussy still intact. She tilted Adam's head back and slipped the phallus into the waiting orifice. She didn't waste any time in shoving the cock back into her slut's throat, causing an immediate gag reflex. She pulled out slightly and slapped Adam across the face, admonishing him for not being able to take her cock and please her. The mixture of the lubricant and Adam's ass juices tasted horrible to him but there was no escape.

Over and over the black invader was shoved down his throat, eliciting an enormous amount of dripping saliva. From above, Mistress Alexandra was once again snapping some pictures of him and telling him to look up into the camera phone.

As she continued to face fuck him she looked him in the eyes and stated.

"This should be a good teaching lesson for you bitch. Every time I take your boipussy you will be required to clean off my cock with your mouth. So it behooves you to make sure your pussy is always clean and smelling fresh. We wouldn't want my new sissy eating her own shit now would we?"

Adam shook his head as best he could.

Eventually the gagging subsided and Alexandra was somewhat pleased with his ability to take a cock in his mouth. But there was so much more training necessary to get him to the point where he would swallow like a pro and crave a good face fucking.

She slipped the cock out of his mouth after another fifteen minutes had gone by.

"Okay sissy, get up, take your dildo friend and my strap-on to the other bathroom and clean them thoroughly with the special soap that is on the counter. Leave them there and then return here to me."

Alexandra chuckled at the way he carefully walked in his new heels on the way to clean the toys. Just another part of training that would take hours and hours so that he would walk like a lady and not a bumbling oaf.

She was sitting with her luscious legs crossed when he re-entered the room. She motioned for him to come to her and she pointed to the floor. Adam kneeled on all fours before her like a well-trained puppy. He looked so sexy on his knees with his heels locked in place.

"Open your legs for me sissy. I need to get a grasp on those tiny little balls. They really are more like grapes aren't they?"

Adam felt his testicles being pulled behind him and before he knew it the humbler had been attached to him again.

"Time for some rest bitch. I will be going out by the pool but you will remain here on the floor. If you take notice, you made quite a mess with all of your clitty leaking. I expect a thorough cleaning of my expensive hardwood floor with your tongue before you rest. Now get to it. And once you finish you can lie here by my desk and think about how wonderful it was that your Mistress took your virginity right here in this spot."

The clacking of her heels as she walked away sent shivers up and down Adam's body. He immediately began to lick up all the wet spots on the floor as instructed and as he dutifully did this he once again felt a newfound sense of fulfillment. He was fastidious in his task, making sure every spot was cleaned up with his tongue. Finally he laid on his side under his Mistress's desk and floated off to sleep.

NEXT CHAPTER COMING SOON!