Paul's Sissy Journey Ch. 05

I was totally restrained and was about to feel the cane for the first time since my sissy training began. I had forgotten to clean off Mr. Black's cock after servicing him and my teacher, Chrissie, was mortified and pissed at me for the disrespect I showed both to her and the Alpha male whose cock I had just sucked.

Now tied spread-eagled on the bed I can honestly say that my fear was substantial.

Without warning Mr. Winchester brought the cane down on my right buttocks. I wasn't prepared for the excruciating pain that it caused. I screamed so loudly I actually surprised myself.

"God this is going to be one noisy bitch." I heard Mr. Winchester calmly state. "Chrissie, get something to keep her quiet. I am in no mood to listen to the wails of a bad sissy cunt."

A moment later Chrissie was holding my head up and shoving a large cock gag down my throat. Buckling it tightly behind my head, there was no escape for me other than to suck on the phallus and breathe through my nose. Chrissie pinched my nose without warning and I immediately panicked, thrashing about as she looked wickedly into my eyes as she controlled any air that I was soon come to cherish.

Thankfully she released her grip.

"You see," she stated. "I not only train you but I also own you while I am here. You have been a very bad sissy and for that you are going to be punished...severely I might add. After Mr. Winchester canes you relentlessly, I will release your bonds. Once released, you will slide out onto the floor, on your knees and ask Mr. Winchester if you may thank him by sucking his very large cock. Do you understand bitch?"

I nodded in affirmation as once again my nose was pinched and my air supply shut off. Devilishly Chrissie smiled at me, knowing that I would do exactly as she requested.

"Please continue Mr. Winchester. I think our little bitch is ready to pay for her mistake."

Another blow struck the other cheek and my howling was indeed muffled by the large cock in my mouth. Mr. Winchester was an expert at wielding the cane, never seeming to hit the same spot twice. The rhythm and the time between blows was mind numbing and added to my ever growing fear. The tears flowed down my cheeks, my muffled cries and repeated attempts at begging him to stop was having no effect on my beating. I lost count after the first ten cracks of the cane. The whooshing sound right before the blow landed was something I would never forget. My body was trembling and my sobbing uncontrollable.

After what seemed like an eternity my beating stopped and Mr. Winchester came near the front of the bed again.

Now whispering to me he said. "Now listen little slut. That cock is coming out of your mouth now. I am going to give you ten more cracks of my cane. But you need to be a good little sissy and beg me to cane you, asking for another after each new blow and counting out the number. Do that for me and this will end your punishment. Screw up though, and we start anew."

Chrissie was soon unbuckling the cock gag and as she pulled it out of my mouth I gasped and almost vomited.

"Let's begin bitch."

I didn't even know if I was going to be able to talk after having my throat stuffed and with all of my sobs that were still emanating from me. I took a deep breath and croaked out.

"May I have another please Mr. Winchester?"

Crack! Oh fuck it hurt so bad.

"Number One. May I have another Mr. Winchester?"

Crack!

"Number Two. May I have another Mr. Winchester?"

Crack!

And so it went and miraculously I made it to ten without failing.

Mr. Winchester stated. "Now that's a good girl. It wasn't so bad was it?"

And then I totally lost it, crying and sobbing, racking my body into convulsions and shaking violently. And with this came my apology, letting everyone know that I learned my lesson and please, please do not cane me anymore.

Chrissie untied my bonds and not forgetting what she had told me, I slid like a spineless snake off the bed and forced myself onto my knees looking up at my tormentor.

"Please Mr. Winchester." I begged. "May I please suck your gorgeous cock as a way of thanking you for my punishment lesson?"

A man of few words, Mr. Winchester nodded in affirmation and I ever so slowly began to loosen his belt. The caning had no doubt excited him as his cock was already semi-erect. And fuck was it big. As my trembling hands took the monster out of his pants, it's length and girth began to continue to grow. The head was huge, almost the size of a baseball. and his balls were extremely large as well.

My sissy mouth went to work, licking and coating his big balls with my saliva. I held the big cock in one hand, unable to actually grasp all around the shaft. As I began licking this huge member I suddenly loved the sight of the shiny black cock in front of me. And much to my chagrin my sissy clit was beginning to leak. Here I was blowing the man who just caused me more pain than I had ever experienced and I was now getting aroused pleasing him. The sight of his luscious cock ignited all of my sissy desires and I couldn't wait to put it into my mouth. I opened as wide as I could and took him in, sucking with a lustful abandon that I didn't even know I possessed. But this was not going to be me in control of his manhood. Mr. Winchester grabbed the back of my head with both hands and shoved the monster down my throat. I was suddenly thankful to Chrissie for making me suck all of those fake cocks in every room! This was the epitome of a violent face fucking. Mr. Winchester was in total control, pistoning his large dick in and out of my mouth, sliding inexorably down my throat, causing me to gag and spit saliva all down my chin. The more I struggled the more he seemed to like it.

And there, out of the corner of my eye was Chrissie, filming the entire scene.

It felt like his cock was going to burst through the back of my head.

The moans and grunts of pleasure coming from Mr. Winchester became louder and this aroused me even more. I could tell he was close as he increased his tempo and incredibly his large cock seemed to grow even more.

The first shot of warm cum hit the back of my throat with such force that it stunned me. Wave after wave of semen kept spurting from Mr. Winchester's cock. And still he held me in place, making sure every last drop of his man seed was fed to me like the sissy slut I had become. And I kept sucking, basking in the glow of having pleased this Alpha giant to the point where he came copious amounts of cum over and over again into my greedy mouth. I wanted more! More cock! More men!

My desire for more Alpha cock was interrupted as Mr. Winchester slowly withdrew his luscious cock from my mouth. Being the dutiful slut and having learned a very difficult lesson, I licked and cleaned every inch of Mr. Winchester before replacing his member back into his pants and zipping him up.

Looking up at him with thankful, sincere eyes I said to him.

"Thank you sir for allowing me to pleasure you with my mouth. I hope I pleased you and I also wish to thank both you and Chrissie for teaching me a valuable lesson today. I won't forget it and I will strive to be a better sissy bitch."

Mr. Winchester actually smiled. He looked over at Chrissie and said. "You know this bitch might actually turn out to be one of the better ones. Give me a call when her anal training really begins. Splitting her in two will be my pleasure."

And with that he turned and walked out of the room and over to the elevator.

With the thrill of my cock sucking finished, I suddenly felt the throbbing of my backside from the caning. My ass was on fire and I began to moan quietly, not wanting to upset Chrissie and be further punished.

"Well slut," she said. " I hope you learned a lesson today and I am sure you will stay away from any future punishment sessions if possible. Now stand up and go take a look at Mr. Winchester's artwork in the mirror."

I struggled to my feet and wobbled over to the bathroom mirror. My ass was a vision of red stripes, all now swelling and placed directly next to one another, virtually covering my entire backside. I began to cry again, looking at what had become of my ass.

And so as I stood there in my heels and caged clitty, looking at what I was becoming I realized that I was crying not out of sadness but out of some type of cathartic appreciation of who I was now and how I was embracing the new me. I had a new lust for cocks and was hoping one day to be able to look and act as sexy and as natural as Chrissie. The sissy had emerged and I was going to do everything I could to become that perfect sissy my wife wanted me to be.

to be continued