Paul's Sissy Journey Ch. 08

The Sissy is Totally Turned

( Paulette had been trained every single day for nearly six months. The secret of developing a true sissy is for them to eventually embrace the whole sissy persona. Paulette was now longing for a cock to suck and was craving cum. She nearly ran to the front room every time Chrissie called in a new Alpha to please. But with the realization that his wife was now fucking a boyfriend and that his position as her husband had dramatically changed put a new found sense of the reality that had been created by Paul being turned into Paulette. This is when a sissy is the most vulnerable to revolt and may attempt to morph back into the husband that once was. But Paulette knew that she had signed the contract with his wife and decided to go through the sissy transformation. And the fact of the matter was that if he had refused, then his wife would have divorced him back then anyway. So the conundrum that Paulette found herself in permeated her thoughts. And Chrissie knew that this was the time that she really needed to step up the new slut's training.

New Training Begins

I was still kneeling and trying to comprehend the ramifications of all that had just taken place. My wife had a new lover and boyfriend. I had just sucked his cock, swallowed his load and thanked him by kissing his shoes. And Chrissie had eaten my wife's pussy and got her off to a wonderful orgasm. And then I was made aware that my wife had been playing with Chrissie years before my wife and I even met.

My reverie was interrupted by Chrissie's voice calling me into the bedroom. I got off my knees, adjusted myself and click clacked into where Chrissie was waiting.

"Fix your face bitch. You look like a cheap whore. The way you attacked that cock was really impressive. Go on, clean up your face and reapply your lipstick."

I did as I was told, just like I always did now without question.

After cleaning up and re-applying my lipstick I re-entered the bedroom and the sight that was before me surprised the shit out of me.

There stood Chrissie, dressed in her hose, heels, and garter belt with a very impressive cock strapped to her, sitting right above her clitty cage. I must admit she looked absolutely stunning and I was leaking like a wanton bitch.

She smiled at me, motioned for me to kneel and strutted forward, her cock swinging lewdly to and fro. I knew what was expected and I took the fake dick and started sucking on it. Chrissie was not gentle and was soon shoving the cock down my throat, causing me to gag and holding my head in place until I was gasping for air. My saliva ran down my chin as she continued the assault on my mouth with her cock. Chrissie was showing me a side of her I had not yet experienced. Her thrusts were forceful and meant to illicit the slut in me. I was really aroused, knowing that the beautiful, sexy sissy that I had come to lust after was face fucking me with abandon.

She held the back of my head, and with her cock nestled in the back of my throat she looked down at me and hissed.

"Now listen to me you little sissy bitch. That cock that you are now gagging on is going up your ass. It is time that we start training you to take cock in your boipussy. I have been instructed to increase the time line of making you a complete sissy. It seems that Master Harding enjoyed your mouth so much that he let your wife know that he wishes you to be able to take his cock in your ass when you return home as your wife's sissy. The text that I received from your wife while you were cleaning up laid out the schedule at which she insists we proceed. So your days and nights will be full of hours and hours of you having your slutty ass filled and fucked. In addition, your wife has decided that she will also be using you, so that means your pussy licking skills must be drastically improved. So my little slut, you can look forward to males and females using you in the days, weeks and months to come."

She pulled the cock out of my mouth and I was light headed from lack of oxygen. I was panting like a cheap whore with saliva dribbling down my face and my mouth still open thinking that the cock would soon be forced into me again.

"Stand up bitch. Let's get you out of that dress.. Time for me to fuck that virgin sissy ass of yours."

I stood up, standing in my heels and Chrissie had me turn around so she could unlock the small lock keeping my dress zipped up. Once done, she had me step out of the dress and then she pushed me forcefully onto the bed.

"On your hands and knees cunt. Your first fuck always needs to be doggie style. We need to get you into the most submissive position possible. Now stick that ass out so I can get the plug out."

I suggestively stuck out my ass just like Chrissie instructed me to do. I had many butt plugs in me but up to this point I had never actually been fucked. And the eight inch cock that I had been sucking on was soon going up my boipussy.

I felt my butt plug being pulled out, and with a plop it slid out. Chrissie told me to open up and the plug was shoved into my mouth. This was my first ass to mouth experience and I was mortified but of course still complied and sucked on the distasteful plug. As I was sucking on it, Chrissie took a scarf and tied in around my mouth like a gag, keeping the plug in place.

She whispered in my ear. "That is so I won't have to hear your screams as I take your ass. I am so excited getting ready to wreck a virgin sissy. After tonight, any thoughts you might have of ever going back to your masculine self will dissolve like an ice cube on a hot day."

Chrissie moved in front of me and lasciviously started coating her cock with lube. My eyes were no doubt wide with both fear and anticipation. Chrissie smiled at me with what can only be described as lustful eyes.

"Now grab those ass cheeks sissy and pull that ass open for me."

I reached back and pulled myself open for her. Almost immediately I felt the head of the large cock push against my hole and begin to painfully spread my sphincter apart. I pushed back like I had been taught with my butt plug training and the head popped into me. I cried out in pain and as I did Chrissie slapped my ass repeatedly.

She yelled out at me. "Shut the fuck up sissy. You need to learn to accept cocks. This is just the beginning. Believe me I have some very well-endowed male friends who will be visiting you in the days ahead. Now let's see if we can goes balls deep on you shall we?"

I felt the large phallus being pushed into me inexorably by Chrissie. I was almost glad to have the butt plug strapped into my mouth, for it gave me a chance to stifle my cries and accept my fate. Finally I felt the balls rest against my reddened ass. Through my whimpers and now tears I heard the unmistakable soothing voice of Chrissie, who now was praising me for being such a good submissive sissy slut. And once again a sense of pride came over me for my ability to take her cock to the hilt.

No sooner had these feelings gushed within me that Chrissie began to fuck me, rocking back and forth, the cock sawing in and out of my ravaged rose bud. And then it happened. It actually began to feel pleasurable! Holy shit I thought, this really feels good. And of course Chrissie could feel my sudden change in demeanor and really started to fuck me. It is a difficult thing to describe to someone, almost like a need to piss but not exactly. As my p-spot was massaged by the massive cock, the pleasure mounted more and more. I soon found myself pushing back on Chrissie's cock, just like a whore would. I was moaning suddenly and the sensations were driving me absolutely wild. I knew and felt my sissy cream leaking through the cage onto the bed. The pace of her fucking me really intensified and her balls were slapping against me every time she thrusted forward. And each thrust was met with a sissy like moan which emanated deep inside of me. I did not want this to stop! The full feeling of being impaled by her cock was rocking my world. I was moaning, blubbering, crying and craving more and more. I knew then, as this epiphany hit me, that I would never be able to live without cock again, both in my ass and mouth. The humiliation would be worth it. And whatever transpired in regards to me serving my wife and Master Harding would be worth the cock that I would be able to enjoy. I know it sounds fucking crazy to those out there that have never become a cock crazed sissy bitch. But I knew what I was becoming and the thought of ever going back was now a thing of the past.

Chrissie kept fucking me and I was delirious with the pleasure I was receiving from her cock.

As she continued to fuck me she softly spoke to me.

" Oh I can tell my little bitch is liking my cock in her now. I can feel and hear your little whimpers and moans of desire. If I keep going we just might fulfill the dream of a slut like you, and that would be for you to experience her first sissygasm. But alas my dear, that is going to have to be delayed until you get a real cock to take you there."

And with that she pulled her cock out of me, leaving me wanting more and feeling very empty suddenly. She told me to slide off the bed and get on my knees. She untied the scarf and took the butt plug out of my mouth and tossed it nonchalantly onto the floor. As I kneeled before her, Chrissie held her cock out to me and I knew what she expected.

"Now sissy," she began. "you are going to clean my cock up of all its juices. Now put it in your mouth and clean me. As you are doing this, let me explain why we are doing ass to mouth. First off, it is so fucking humiliating for you and that in itself is something sissies like you thrive on, whether you realize it or not. And secondly, after an Alpha male has used your ass for his pleasure and deposited a huge load of warm cum into you, it is only fitting and necessary that you clean him off, just like you do after giving them a blow job."

My mouth had been busy cleaning Chrissie's cock of my ass juices and the lube. It was distasteful to say the least, but she was correct in assuming that the act was so humiliating and kinky that it actually was arousing to me. And of course I knew that the other desired effect would be that I would constantly pay attention to keeping my boipussy as clean as possible all the time.

"That's a good slut." she cooed. " Now carefully take the strap-on off me and take it to the sink and clean it. When you come back I have a nice new butt plug to get you feeling full again."

Still on my knees, I removed the cock harness from Chrissie and noticed immediately the amount of sissy cum that had dribbled down her thighs. She no doubt enjoyed being the "fucker" as much as I enjoyed being the "fuckee". I crawled to the bathroom, stood up on what can only be described as wobbly legs, and cleaned off the cock and left it on the sink to dry. Back on my knees, I crawled back out to Chrissie and remained kneeling by the side of the bed.

Chrissie stepped forward with a box in her hand and told me to open it and look inside.

I opened the box and inside was a very large stainless steel butt plug.

"This is the XL N-Joy steel plug. One thing my little slut will notice is how heavy the plug is. Now go ahead sissy and lift it out of the box."

I did as I was told and was shocked by how much this plug weighed. I swear it was close to two pounds and the mushroom head was substantial to say the least.

Chrissie took the plug out of my manicured hand and told me to stand up and bend over at the waist. I once again followed her commands and soon the cold steel actually made me jump when she began to push it into me. The damn thing was big, but the weight of it, once it entered me, would be a constant reminder that I was a sissy slut with a plugged ass. The other feature of the plug was the way it was shaped and how it slipped between my cheeks, snugly pressing against me but also how comfortable it felt. Chrissie had me model for her and walk around the room in my heels. Every step made the weight of the plug move slightly and the result was a feeling of euphoria. It was like Chrissie's cock was still embedded in my ass.

Chrissie watched as I strutted about like a true sissy, making sure to walk heel to toe and to look as feminine as possible.

She suddenly removed her panties and looked at me with those lustful eyes again.

She sexily whispered to me. "You know slut eating out your wife really turned me on and I have been extremely horny ever since. I loved taking your virginity and now, with the approval I received from your wife, I am going to have you eat my ass and give me a thorough tongue fucking. I expect you to be on your best behavior and to orally pleasure me with as much focus and excitement as when you suck Alpha cocks. Now get on your knees again and make love to my ass!"

Holy shit I thought. After all these months of lusting after Chrissie, she was offering her ass to me for orally worship. I did not hesitate for a second. I know, this was the ass of another sissy, but that seemed to excite me even more. The changes that had been trained and hypnotized into me were certainly having their desired effects. I was dripping with so much excitement as I began to slowly kiss and lick my way around Chrissie's rosebud. My wife had never really been into any anal with me so this was a fairly rare and new experience for me. After sucking and pleasuring so many cocks I found myself copying some of the same teasing techniques that I had learned to do with cocks. I knew Chrissie was unbelievably horny, so rather than just attack her asshole, I decided to slowly use my oral skills to lick around her hole with a tantalizing tongue action. God I was in sissy heaven. I found myself swaying my own back and forth to feel the weighted plug more and more in me. Chrissie was moaning softly and as I got closer and closer to her boipussy her breaths became much more ragged and labored.

"You fucking tease," she shouted. "If you don't get that wet tongue of yours in my ass immediately, I promise to call for some punishment time. Now fuck me with that tongue bitch!"

With a huge smile I moved to her hole and slowly pulled her cheeks apart to reveal her sexy bleached asshole. I pushed my tongue forward and it met some resistance. Without being plugged like me all the time, Chrissie was quite tight. But I would not be denied and as I stiffened my tongue as much as I could I breached the ring of her anus and began a slow fucking motion, pulling her hips into me as my tongue buried itself in her hole. It is not an easy task to keep one's tongue inside a hot asshole while trying to emulate a fucking motion. But I must have been doing something right because Chrissie was panting and moaning very loudly as my oral ministrations continued to arouse the hell out of her. Her body actually began to shake and then she screamed at me.

"Hurry bitch, get in front of me. I am going to cum in my cage and I want my sissy juice to drop into your mouth. Hurry up bitch. Fuuuuuck!"

I quickly got down in front of her with my mouth open and wide right beneath her chastity cage. And it was just in the nick of time because Chrissie started cumming and her juice flowed out of the cage directly into my mouth. it was the most erotic, exciting thing that I have ever experienced. It was not like an Alpha orgasm, wherein the cum shoots out of the cock. This was much more of a subtle flow that was finding its way into my sissy slut mouth. Chrissie took one hand and steadied herself on the edge of the bed, preventing her from actually falling over during her sissy cumming. I was craving more and more of her juices, hoping that the sissy flow would never stop.

"Oh my God slut. I haven't cum in weeks and that felt so damn good. Now open up and show me all of my sissy juice before you swallow."

Still in the same position, I opened my mouth as wide as I could and showed Chrissie all of her deposits. Her smile and nod was the sign for me to swallow her load. Two things that I quickly realized. The first thing was that her cummies were quite clear and not thick like the Alpha males I sucked. No doubt a result of the estrogen pills and other feminization parts of her diet. And secondly, her juice tasted almost sweet. Boy was I fucked, because I knew after getting that first taste my cravings for it would become an addiction.

Both of us were spent, and after brushing our teeth, we headed off to bed. Chrissie letting me know that unlike what I would do previously with my butt plugs before bed, this one would stay in all night. She explained that with the stainless steel plug she was able to use an oil based lubricant that would keep me lubed all the way through morning. I don't remember my head even hitting the pillow.

TO BE CONTINUED