Paul's Sissy Journey Ch. 03

TIME GOES BY

The next day I was awoken early by the alarm. Chrissie was already standing at the foot of my bed smiling at me. She once again was dressed to the nines in a very provocative ensemble. Suffice to say she would never disappoint me as the days went by and she never seemed to wear the same sexy outfit twice.

Learning from the previous day's error, I jumped out of bed, crawled over to her on my knees and kissed her heels as I thanked her for taking the time to train me. She looked down at me approvingly, which I must admit made me feel good. After a few minutes of me worshipping her, she pointed to the bathroom and I headed over to the shower. As would be the case every morning, she watched me intently as I cleansed myself. After drying off and using the toilet I lubed up the butt plug and inserted into my boipussy.

"Follow me." Chrissie stated.

I did as instructed and followed her out into the living room. In the middle of the room an aesthetician had already set up a table and what I assumed was electrolysis equipment was set up also.

I was a bit embarrassed being totally naked in front of this new stranger but she smiled at me and motioned for me to climb up on the table. I once again did as instructed and the lovely red head, who was dressed in a very sexy short-skirted nurse's outfit explained to me the procedure. The removal of my body hair was to begin today and would take place every other day until the desired results were reached. I had no idea the process would take so many hours. I was thankful that I had very little hair to speak of on most parts of my body.

The red-head introduced herself as Helen and had me lie on my back. She explained that she would start on my, as she called it, the clitty region and work her way down my legs.

Chrissie positioned herself at the end of the table and briefly explained what other things were to be accomplished today.

"So Paul," she began. "Yesterday we took your measurements and a few items have already been delivered. In your closet you will see an assortment of heels. Each pair is equipped with a locking strap that will insure they stay on as required. Walking in heels is something a sissy will always do and I will never see you walking again, except when going to and from the bed and shower, without a pair of heels on. They will become a part of you, just as this will."

In her hand Chrissie held out a pink chastity cage, which seemed awfully small to Paul.

"This is your first cage. As we move along in time, other smaller cages will be exchanged until your clitty has shrunk to the appropriate sissy size. As with the heels, you will never be free of the cage unless supervised by one of your trainers. After Helen finishes the first treatment around your clitty, I will be putting the cage on you. Previously with many other sissies I have allowed one last orgasm prior to locking the cage in place. However, in your case your wife left explicit instructions that it would not be the case with you. I will probably need a bag of ice to shrink you down for the cage to be put in place and I am sure for the first few weeks, when the cage is removed, the ice will be necessary again and again. So as Helen begins her work on you, just imagine that you will never have a male orgasm ever again and the only way that clitty will be allowed to leak out it's sissy juice will be from anal stimulation. This is the world of the sissy Paul."

I was shocked and dumbfounded at the same time. For the first time since arriving, thoughts of escape rattled around in my head.

Chrissie must have noticed the look of concern and consternation on my face.

"Don't worry bitch." She stated as she looked down at me. "I have seen that look many times before. The realization that your manliness is being taken away so suddenly can be a shock. But believe me eventually you will thank me for taking away any and all semblance of your past masculinity. Soon you will be leaking copious amounts of sissy juice out of your new cage rather than the inappropriate erections that you seem to get every time you see me. You must admit a hard clitty is not very lady like. Now put both of your arms on the sides of your body."

Unbeknownst to me, leather straps were attached to the table and the ladies wasted no time in securing my hands, buckling then snugly. The same was done with both my feet. I was virtually immobile now, looking up and seeing both of the hot women smiling at me.

A blindfold was then put over my eyes and a set of head phones placed over my ears. A soft voice began to speak to me, calling me by name, soothing me and relaxing me and eventually hypnotizing me into what I guessed was some type of induced sleep or trance.

I awoke slowly with the gentle voice still whispering in my ears. As the effects of the hypnosis began to dissipate, I felt a coldness between my legs. Opening my eyes, and still being bound to the table, I tried to lift my head and see what was going on. And there it was, a big bag of ice covering my cock and balls. There was no way knowing how long the bag had been in place but the extreme coldness began to turn into a dull ache. The women were nowhere to be found and because I was still basically immobile, the bag remained in place even with my feeble attempts to shake it off of me. I was ready to call out, but caught myself just in time, remembering the edict regarding no talking. So I remained silent and waited.

Finally, in what seemed like an inordinate amount of time, I heard the familiar click clack of high heels nearing me. And there stood Chrissie, sporting a huge wicked grin.

"So bitch." She began. " I think the ice has done its job and has shrunk you sufficiently so that I can get that clitty caged. Let's see what we have here."

She removed the ice bag and lifted my now limp and shriveled penis in her hand. Quickly drying me, she proceeded to apply Vaseline around my balls and cock. The device was simple enough. Chrissie slipped my balls through an opening in the main part and then squeezed my cock through the same opening. Very much reminding me of a cock-ring now, except there was a top piece that slightly extended from the ring. The second part, a small tube, was slid over my now tiny dick and the two pieces fit together, snugly trapping me. There was a build-in lock that, with a key, and it was then locked in place. Straining all this time to witness the locking away of my cock, I was amazed at how tight and small the pink cock cage was. And Chrissie said this would be the biggest size used on me. The vision actually aroused me, and I soon felt the pressure of the cage not allowing me to grow at all. Chrissie lightly scratched my now hairless balls and seemed satisfied with her work.

"Welcome to the world of chastity Paul. I know you have seen my bulge while looking up my skirt and have been wondering about it. So here sissy, have a look."

Chrissie lifter her skirt, pulled down her lacy panties and showed me the bulge that I had wondered about was indeed a chastity cage, much smaller than mine. And I also noticed Chrissie's balls had been removed.

"I have been in chastity for three years Paul. I, like you, was a victim of nasty male erections. But those are all long gone, a thing of the past. And I love being locked up and being used for the pleasure of others. One day sweetie, you too will share these feelings and become the sissy your wife has envisioned. But for now, we will train you to be a locked -up bitch and a good gurl. Now I am going to unbuckle your feet, but do not move your legs until I get your new heels in place and locked."

I remained still and Chrissie reached behind her and grabbed a pair of black heels. One at a time she slipped them on my feet. They were designed in such a way that when the ankle straps were in place a small padlock was attached and clicked, locking the heels in place and preventing them from being removed.

So suddenly things had progressed quickly today. I was now plugged, locked in chastity and had heels locked onto my feet. I had also had my first session of hair removal while under some type of sissy hypnosis.

Chrissie loosened all of my bonds and had me sit on the side of the table I had been secured to. As I slowly regained my bearings, I noticed lines of blue tape running throughout the living area and into the other rooms. There were a set of double lines, approximately six inches apart.

Chrissie saw my confusion and perplexed look, and with that sexy smile began her explanation. "Well bitch, I know you are wondering about all of the lines on the floor. At first glance it might seem totally weird, but there is a method to our madness. You see, walking in heels correctly is such an important part of being a perfect sissy. And unfortunately, so many sissies still retain some slivers of masculinity because they stomp around in their heels, the result of never being properly trained and anyone looking at them notices this. You know damn well your wife is a perfectionist. What that means is that all facets of your training will be done until near perfection is achieved. And walking in heels is just one some part of training you to be her perfect bitch."

"But I digress. Back to the tape. Because it is essential that while walking in heels one foot goes in front of the other in a heel to toe action, the area between the lines of tape will be the only areas you will be allowed to walk. And the only way you will be able to stay within the lines is by walking with one foot in front of the other. At no time, other than being in the shower, will you be allowed outside the lines. This will require much concentration on your part and a new found focus that I will bring out in you with the help of my cane. As we begin our heel training today please understand that falling outside the lines will be met with swift punishment. Our schedule will be two hours of training in the morning, followed by some sissy porn watching, followed by another two hours of heel training. In between you will have lunch while listening to sissy hypnosis. Do you understand bitch?"

Rather than nodding my head in agreement, I made the terrible mistake of talking. "I am not sure I can do"...Whap!

I fell to the floor in agony. My whole body shook and I was confused as to what the fuck was going on. It felt like someone had taken an ice pick to my balls.

"Your sissy cage also has a shock element attached. Any outburst from you, any form of disrespect, or any times I might be in a naughty mood, this is what happens bitch." Again she was wickedly smiling as she spoke. "So now that we have that taken care of, let's proceed with your high heel training. I suggest you listen to me and do as I say. And remember, stay in the lines. Otherwise you will be spending a whole lot of time in a fetal position writhing away. So up you go sissy. Now look at the big screen. These are very important dos and don'ts. Read them out loud for me now."

I was scared shitless to talk but the look on Chrissie's face told me to proceed. On the screen was a list.

I repeated what I read to Chrissie.

" Number One...Retain Good Posture"

"Number Two....Take Small Steps"

"Number Three..Don't Lean Forward or Back"

"Number Four....Place One Foot in Front of the Other"

"Number Five....Relax Your Legs"

"Number Six.....Walk Heel to Toe, Click Clack, Click Clack"

Chrissie clapped her hands. " Good gurl. Except when sissy porn is on, these tips will remain on that screen so you can practice, practice, practice. Correct posture and a slutty swaying of the hips is a must for a sissy when walking in heels. You see Paul, once I am done with you every man who sees you walking down the street in your heels and short skirt will want to fuck you like a whore. They want to do this to me now and it is a tremendous feeling. So let's get started shall we bitch?"

The next two hours were a living hell for me. Although the feeling of being in heels was a complete turn on for me, the practice that Chrissie put me through was exhausting and painful. Numerous times I stepped out of the lines. And each time the shock debilitated me and I fell to the floor. The tears soon came, but I knew better than to beg for her to stop. Over and over I walked until my calves were crying out in pain. The sound of Chrissie yelling at me, telling me to improve, to do better, to quit walking like a man...the sound resonated in my voice. I was really beginning to dislike her.

And then, finally, after practicing for God knows how long, she actually gave me a compliment. Now the normal response that one would expect after being tormented for so long would be a resounding " fuck you." But for some reason, the simple compliment coming from her made me feel like I had really accomplished something and I was very proud to have been able to do this for her. Without any command, I dropped to my knees and began kissing her heels as a show of my gratitude. I began to sob quietly (what had gotten into me) as I continued to kiss and lick her high black heels. At that moment, all I wanted to do was to please this beautiful sissy who was putting me through my paces.

With a voice so soft and sweet I thought I would melt she said. "It's ok sweetie. With lots of practice and focus on your part you will be walking and swaying in theses heels like a true sissy slut. Now I heard the bell so your lunch is ready. How about you get something to eat, then two hours of sissy porn on the couch and then two more hours of heel practice. Then a shower and in bed by nine with your headphones in place."

And that was my schedule for the next two weeks straight with no variation at all except the fact that Chrissie increased the size of the heels I wore, so by the end of the second week I was walking in five inch stilettos. The daily porn and the hypnosis was certainly taking a hold of me. Every morning I would wake up with sissy juice running down my balls and messing the bed. My mind seemed to focus on real men's cocks and what it would be like to suck another one once again. Almost every porn video that I watched had some type of Domination involved with a sissy invariably either sucking cock or being fucked by a large penis. More and more my clitty leaked as I watched, so much so that Chrissie insisted I sit on a towel so as not to stain the couch. Sometimes I wanted so badly to play with myself while at other times I thought of rubbing my boipussy and wondering what it would feel like to have a real cock up my ass. I will say that during all this time the electric shocks became fewer and fewer until finally I actually made an entire day without writhing in pain on the ground.

There was no way that I had any touch with the outside world so the days began to become a blur. I tried to keep count as to how many days I had been in training but it seemed my brain was focused on too many other things, all revolving around the sissy lifestyle.

One morning, and I believe it was during my third or fourth week, when I woke up at six like I did every other day, instead of just Chrissie looking over at me from the foot of the bed there was a man standing next to her. He definitely was much taller than Chrissie and was dressed in a black Nike sweat suit, with black sneakers and a black mask covering most of his face.

" Time to get up bitch. Let's get those heels unlocked ( yes, I did indeed sleep in the heels also) and you will hop in the shower." Chrissie stated. " Today we will go up to six inch heels which I am sure you will have no trouble with. Let's move!"

I was mortified to get out of bed totally naked sans my heels and cock cage in front of this man. But being the good sissy that Chrissie was turning me into, I did as I was told. After my shower I reached for my butt plug only to be surprised that it had been replaced by a much larger plug. I must admit at times the other plug had a tendency to want to slip out of my stretched boipussy so I suppose a bigger plug made sense. It also solidified my assumption that my hole was indeed getting stretched out in order to eventually accommodate a real man's hard cock.

Once plugged and after putting on the new high heels and having them locked in place I was on my knees worshipping Chrissie's heels and thanking her as was my daily ritual.

"You know," she said. "Since you have been such a good bitch for me the past week we have decided to give you a special breakfast today. There is nothing that excites a sissy more than a hard cock and a mouthful of warm cum to start the day. My friend Alex here has been nice enough to feed you your breakfast. As you work for your morning meal, I will be taking notes in order that I can determine what areas of cocksucking we need to improve. Now crawl over to Alex and ask him politely to feed you his cum."

So for the second time in my life I was going to suck a real cock. Just the thought had me leaking profusely and I could not wait to get that hard cock in my mouth. I had been locked up for about three weeks and my state of arousal was beyond comprehension. As I crawled over in front of Alex, I inadvertently let out a wanton moan of excitement.

Chrissie laughed and said. "Well just listen to that. I guess all the videos and hypnosis are having a nice effect on our new sissy. Now be a good slut and ask Alex nicely."

Now kneeling before Alex, I looked up into this large man's face and asked as politely as possible. "Please Mister Alex. May I please have my breakfast now. I would love to be used for your pleasure."

Alex laughed and bellowed forth. "Well of course sissy. Take my manhood out and let's see what we have to work with. If you do a good job I will feed you. But if you aren't able to elicit the correct response from me I will cane you until you sob."

Holy shit I thought. I was trying to remember all the techniques I had witnessed on so many of the videos I had watched.

There was a draw string on the pants, no zipper, so I carefully untied Alex's pants and slid them down his legs. I was immediately surprised by the size of the black cock staring back at me. Still flaccid it looked to be about seven inches long. It was gorgeous to me, how it shined and without any pubic hair it seemed to beckon me to move in and use my mouth, tongue and lips. Remembering what I had watched on the sissy porn videos, the first thing I did was kiss the large head as a show of respect. I could taste the pre-cum that had already leaked out a bit and that further energized me, knowing that Alex was excited to have me fellate him.

I began to lick the underside of his shaft, slowly working my tongue back and forth. The hardening of his cock let me know that what I was doing orally was stimulating him. I reached up and with both hands carefully fondled his balls, taking each one into my mouth and seductively sucking them. His moans were music to my ears. His cock was now as hard as steel and had grown another inch or so as it leaked pre-cum onto me. I teased him and licked him waiting to eventually put him in my mouth. I wanted to suck him immediately but I realized at that moment my desires were secondary to the pleasure I was to bestow upon him with my sissy mouth.

"Put that cock in your mouth slut."

Those were the words I was waiting to hear. Opening up wide for him, his bulbous head soon was in my mouth and I was ever so slowly guiding him further into my warm orifice. I had a grip now on the gorgeous erect cock, controlling the speed to which it entered me. My saliva was slathering all over him and as I worked and sucked him even further the moans and panting that were emanating from him now were incredibly arousing to me. I was leaking all over the hardwood floor and I was inadvertently clenching the butt plug in my ass as I continued to please Alex. As I took him in I began to gag occasionally when the cock entered my throat. As I gasped for air his motion would push his manhood deeper down my windpipe until finally I seemed to be able to relax enough that it could stay there for a few seconds as I breathed through my nose. My saliva was literally running down my chin now and my determination seemed to grow as Alex neared fruition.