Paul's Sissy Journey Ch. 02

IT BEGINS:

I followed Jeremy submissively to the car. A long black limo was idling before me. Jeremy opened the beck door and told me to get in. Still dressed like a sissy slut, with the taste of Jeremy's seed still in my mouth, I crawled in and sat down. The door was closed and I found myself in complete darkness. All windows had been blackened out and I could barely see my hands in front of my face.

As the limo pulled away and my journey was beginning, a sense of fear and trepidation all of a sudden overcame me.

Was I really leaving all semblance of my previous life behind?

Was I really ready to become a full-time sissy for my Dominant wife?

Did I just suck my first cock and enjoy it?

So many thoughts swam in my head as the drive continued. I was absolutely embarrassed and humiliated that I had signed the paper for my wife and had then dressed as a slut and sucked a real cock. But why was my soon to be called clitty hard and leaking still? Why did I follow Jeremy so meekly into the limo with no thought of leaving at that time?

I closed my eyes, laid back and soon nodded off to sleep.

My slumber was interrupted as the car came to a stop and the engine was turned off. The back door was opened and my eyes adjusted to see a stranger peering in at me and grabbing me by the arm, gently pulling me out into the moonlight.

"Follow me," He stated.

Once again, I meekly followed this stranger, listening to the click clack of my heels and doing everything in my power to not fall on my ass. We ascended approximately 50 or so stairs and then proceeded to the front of what appeared to be some type of private, luxury hotel. As I entered, I noticed the myriad of cameras that made me realize the depth of security here was quite impressive.

A voluptuous blonde smiled at my unknown host and walked over to the elevator in what I can only describe as the highest heels I have ever seen on a woman. She used a key to open the elevator doors, motioned for me to get in, joined me, leaving my male stranger friend behind.

I found it odd that there were no floor buttons to be pushed inside the elevator. I also noticed two more cameras looking down at us.

I decided to break the silence. "Please Miss, can you tell me where I am and what is the name of this hotel?"

In a sexy, breathy voice, the blonde looked over at me, smiled wickedly and said. "No talking. No questions."

"But," I tried to ask.

Whap! Her hand struck my right cheek with such force that I actually staggered back.

Looking at me with a wicked grin, she put her finger to her lips signifying for me to remain silent.

I knew better than to challenge her. I stood silently, inadvertently lowering my eyes to the floor, realizing that this was indeed all real and my adventure into feminization and sissyhood would begin once the elevator doors opened.

And right on cue the doors opened. I was motioned out, the doors closed behind me, and I found myself in what can only be described as a luxurious penthouse. The main room was quite large, tastefully decorated with beautiful white modern furniture. The wood floors were a light maple color and the walls were the color of a shade of pink. The decorating certainly was very feminine and had all the details of a womanly touch.

On closer inspection, I noticed two things.

Cameras were everywhere. There was no attempt at hiding them. I knew at that moment that any sense of privacy that I might like while staying here would be non-existent. I suddenly wondered who would be viewing the feed from the cameras? Would it only be Crystal my wife? I hardly thought so. But then who?

The other thing I soon noticed was the artwork that adorned the walls. Casually viewing the art from across the room, the paintings seems to be all abstracts done in a variety colors of pink. But closer inspection revealed that every work of art had erotic images of submissive sissies being dominated in some sexual way, cleverly weaved within the abstract brush strokes. A slight shiver went down my spine as I came to understand that every detail of making my temporary domicile a sissy haven was done in order for me to never forget why I was here and what I had agreed to.

My bedroom was a very bright pink with a large mirror hung above the bed. The artwork was not so much abstract in here. The images were very apparent and powerful.

Just above the headboard of the bed a large painting depicted a very feminine sissy, cock caged and balls tied, being fucked from behind by a very dominant looking black man. The look on the sissy's face, with eyes rolling back in her head, was one of complete submission and rapture.

On the opposite wall there were five erotic paintings, all showing a sissy on knees sucking cock. The sissies were all dressed differently, were all a variety of ages, and were sucking both real cocks and also cocks of female Mistresses. Every sissy's eyes were looking up at their Dominant partner, with a glassy-eyed submissive emptiness that portrayed their complete acceptance of their roles.

The bathroom was also very large, with a huge walk-in shower that had a variety of shower heads situated at different heights. I also noticed the many eye bolts that were embedded in the walls of the shower, also in a variety of locations.

I tried not to let my mind get ahead of myself as I took in all of the penthouse.

I click-clacked into the modern kitchen ( looking back I found it interesting that I had yet to take my heels off) and opened the fridge. Much to my disappointment, the only items in the fridge were a few bottles of water.

I grabbed one of the bottles, headed over to the couch and finally sat down, all of a sudden feeling very tired.

"Hello Paul."

What the fuck?

There, right before my eyes in 4D pixilation on the large 75 inch monitor that was on one wall in the living room, was my wife. She was dressed in one of her Armani business suits and appeared to be sitting in one of the conference rooms at her law practice.

She continued. "Because you are now watching this video it is affirmation that you signed the document presented to you and you have decided to become my sissy bitch. This makes me very happy Paul. For as long as I can remember deep inside of me there always was a desire to feminize you and to turn you into my own personal play thing. I fought my desires for a long time, but as our relationship lost much of its spark, culminating in you embracing your sissy tendencies, well, my mind was immediately made up. I realize that the fantasy world that you spent dressing up, sucking fake cocks and invading your boipussy was something that you figured would always stay just that, part of an erotic dream for you. But now my sweet husband that fantasy world is going to be slowly turned into your lifetime reality. Grasping this idea will no doubt be at times very difficult for you, but with the experienced professionals I have hired who will be there every step of the way with you and your transformation, I am quite positive that at the end of your 12 months of training, you will be the perfect sissy for me and my friends."

I was taken aback...12 months?

" A very careful plan has been created for you. There are a variety of stages, all of which I will expect you to complete like the good submissive you are to become. Unfortunately, I am a pragmatist and realize that there will be at times some insubordination on your part. As you will come to learn, discipline and punishment will be a vital part of your training scenario. There will be pain followed by many tears that will stream down your face as you sob like a little bitch....begging for the punishment to stop. Only your handler at the time will make the determination as to the severity and longevity of each punishment session. As you are now acutely aware, every minute of your transformation training will be videotaped for my viewing. It is important that we have a video history of what you once were and, after 12 months, what I have turned you into. Now, some specifics. Number One. You will not be allowed to leave this penthouse for the duration of your 12 month training alone. On certain occasions, when it is felt that public humiliation is deemed necessary and important to your training, you will be accompanied by one of your handlers to a location of their choosing. You will be closely followed by another handler who will document everything on video. Number Two. All facets of your life will be controlled. A high protein diet will be instituted immediately. Exercise will be a daily requirement. When you sleep and when you wake will be strictly enforced. You will notice that the closets and dresser drawers are currently empty. Once you shed your current attire tonight, you will be kept naked for at least the first 30 days.

Number Three. Your body now belongs to me and I will mold it and change it to satisfy my vision as to how I want you to eventually appear. There will be electrolysis to rid yourself of any manly hair. There will be some plastic surgery, although to what extent I have yet to decide. Female hormones will eventually become a part of your daily intake. Your current cock will be caged tightly, slowly shrinking as the months go by. Your balls may stay, or may go. I have been looking at many photos of sissies without their balls and I am beginning to really like the look. Just a little clitty hanging daintily between your legs is a sight that I will look forward to, minus any masculine balls. Number Four. Hypnosis will begin tomorrow and it will be a vital part of your transformation.. Your mind will become a wonderful receptacle for all things sissy. Fortunately for me, and perhaps a bit disconcerting to you, is the fact that one day you will indeed be a mindless sissy bimbo, only concerned with providing pleasures to others. But of course, that is what you have really wanted all along, right sweetie? There is so much more, but I know you must be very tired. So, after this video ends, you will take off all of your cute clothing and place it in the laundry chute located in the laundry room. You will then get into bed and go to sleep. You will be woken up in the morning by your first handler. Remember, following direction without hesitation will be a prerequisite to not being punished. This is the last time you will see or hear me for the next year. But don't worry honey, I will see you every day and night. Now run along sweetie, do as you are told and sleep well. Remember, I still love you and will love you a thousand times more when you are completely transformed in a year."

The video ended abruptly, the screen turned to blue and I sat in a state of shock and disbelief.

What had I done? Was I really prepared for what might lie in store for me?

I was so fucking tired that I just got up, removed all of my clothes and wandered over to the laundry room and put them all down the chute.

The pink feminine bed was a welcome sight and I crawled into it, suddenly understanding that this was to be my place to sleep for the next year. Holy shit! I closed my eyes and drifted quickly off to sleep.

FIRST DAY:

The next morning came way too quickly. With an alarm blaring in my head I was confused to where I was. It took a moment for me to come to grips with my current location. I had no idea what time it was. I would normally look at my phone for the time, but of course that was no longer in my possession. As I rubbed the sleep out of my eyes, a female form came into view at the foot of my bed.

"Good morning sleepy head," she said. "Today is the first day of the rest of your life. The date today is March 17th. This will forever be known as your sissy birthday. My name is Chrissy and I will be your handler for the first month of your stay. Now get out of bed and come stand over here near the mirror. I need to do an inspection of what I have to work with."

As I began getting out of bed it dawned on me that I was completely naked. I hesitated for a moment but immediately saw the look on Chrissy's face that told me to hurry up. I got up, stretched my early morning limbs and stood before a full-length mirror. I was embarrassed by my early morning wood and tried valiantly to get it to go down.

As I stood before the mirror, I was able to really take in Chrissy and how lovely she was. Not only did she have a beautiful face and figure, but the outfit she wore oozed sexiness. She wore a short black leather skirt that barely covered her backside. Her luscious legs were adorned with seamed thigh highs being held up with a black garter. Her feet were encased in a pair of black Louboutins with at least a five inch heel. I knew the brand of the heels from the red soles that my wife pointed out to me when shopping with Her. The heels were extraordinarily expensive. A white silk blouse was covering the upper half of this amazing creature, with the buttons undone at the top revealing just a hint of cleavage. Her hair was an auburn color, straight and cascading over her shoulders.

"Now that you are done staring bitch, put your hands on top of your head and stay still. Do not move until I tell you to."

She had just referred to me as "bitch" and this somewhat surprised me.

I took my position as she requested.

"God, all this fucking hair, "She disgustingly stated. "What a mess."

From a dresser drawer nearby she retrieved a small pad, a pencil and a measuring tape and some latex gloves. After slipping on the gloves, she began taking measurements of all of my body parts and jotting them down. My feet, my legs, my butt, etc..

When she came to my dick, she just matter of factly measured it like it was any other part of me. The length, the girth, circumference around my balls, everything. She measured the opening of my mouth and the opening of my ass. I was so totally flustered and humiliated by the time she finally was done.

"Ok bitch. I am done with the inside measurements. Now I need you to bend over and grab your ankles for me."

" Are you kidding me?" I replied.

Whap! For the second time since arriving a sharp slap rocked my world. My cheek burned with both pain and shame. I bent over as asked.

From the drawer Chrissy grabbed a small bottle of lubricant and squeezed it onto her fingers. Stepping behind me, she inserted a finger up my ass. This was followed by two fingers, then three and finally four.

" Well well bitch. I see someone has been already been playing with this boipussy. You are a little slut aren't you?"

Snapping off her gloves, Chrissy then ordered me into the shower. My humiliation continued as she instructed me how to clean myself and how to negotiate the many different nozzle locations to help facilitate both the outside and inside of me being washed thoroughly. When done, she handed me a pink towel and told me to dry myself. When I wrapped the towel around my waist, she chastised me and showed me how a sissy should wear a towel after showering.

She next showed me which scented moisturizers I was to use every day. She also told me to use the toilet as needed. I looked at her incredulously as I understood that she was not intending to leave the bathroom as I relieved myself. She instructed me to always sit down to pee and I noticed that the lid of the toilet was attached so that the lid could never be raised up. It took some time but I was able to finally pee in her presence.

After washing my hands, Chrissy told me to follow her back into the bedroom. Once again, she instructed me to grab my ankles and not move. From my position I couldn't see what she was doing, but as she got behind me, I felt the tip of a butt lug beginning to be pushed into me.

Chrissy cooed to me. "Normally I would start with a small training plug, but since we all know how much of a slut you already are and how you have played with yourself multiple times, this medium size will suit you for now. Let's see that sissy ass swallow this plug for me like a good slut."

Her words were arousing to me, and the thought of this sexy woman pushing a butt plug into me was extremely exciting. As it passed by my tight ring and became embedded within me, Chrissy slapped my ass as a sign of accomplishment.

She once again talked to me. "You may now stand up bitch. Get your sissy ass over and make your bed. I expect no wrinkles in any of the sheets or covers. Once done, kneel at the foot of the bed for me."

Now I couldn't remember the last time I had to make a bed. So it took me some time and a few re-dos to get it right. Finally I was pleased with my work and took my place kneeling at the foot of the bed.

Chrissy stood looking down at me and from this vantage point her short skirt revealed a small lump in her lace panties. I was flabbergasted. This gorgeous bombshell used to be a guy? The thought that a year from now I could look anywhere near to this beauty was so hard for me to comprehend.

"Get down and kiss my heels bitch. Show me how much you appreciate me taking the time to train you. From this day forward, every time you greet me, I expect you to be on your knees and kissing my heels or boots. And each evening prior to putting you to bed, you will do the same. Now nod your head if you understand."

While kissing and licking her heels, I nodded my head in affirmation.

"Good bitch. Now while you are down there worshipping me, there are a few items we need to sort out. Unless asked a question, I never want to hear you speak. Your masculine voice is so annoying and it will be changed eventually, but for now no talking. Understood?"

I nodded again.

" Your butt plug will remain in place from when you arise until when you are put to bed. You will shower in the morning and at night. After your morning shower the plug goes in and after your evening shower it gets removed. Taking proper care of your toys will be your responsibility. Let me find a dirty toy just once and there will be hell to pay. Understood?"

I nodded once again as I kept to my worshipping her heels.

"The measurements I have taken today have already been sent out and certain items necessary to start your training will arrive tomorrow. Today you will be allowed to rest on the couch and watch sissy porn all day. You may leave the couch when your breakfast, lunch and dinner arrive. There is a dumb waiter in the pantry and a bell will ring to signify your meals arrival. You are to eat all of your meals at the dining room table and I will expect everything, and I mean everything served to you to be eaten.

Finally, knowing what a slut you already are, I realize you will want to play with your sissy clitty all day long as you watch your sissy porn. This is strictly forbidden. There will be absolutely no touching of your clitty by you today. Touch it just once and punishment will be forthcoming! Now crawl over to the couch. The videos will start shortly. Enjoy your free day little sissy. Tomorrow our work begins in earnest."

With that Chrissy sauntered out and entered the elevator leaving me behind on the couch. As promised, a video started right on cue and I settled in for my day of viewing.

The first video was more of a tutorial than anything else. The title was "All Things Sissy" and the content consisted of what attributes make a perfect sissy slut. It started innocently enough, but eventually many lurid scenes of sissies being fucked and sucking cock were dancing across the scene. My cock began to ache, begging for relief, but I knew better than to touch it. I was really mesmerized by the looks on the sissy's faces as they were penetrated and fucked by large manly cocks. My mind was totally absorbing all that I was seeing and I wondered if this was actually some type of sissy hypnosis video. I found myself actually wondering if it was going to be possible for me to achieve such exquisite feelings of submissiveness that I was witnessing on screen. And could I really be trained to take cock in my mouth and boipussy with such ease as these sluts seemed to do?