Paul's Sissy Journey Ch. 06

Days turned to weeks and weeks turned to months. Every day was a training and learning day for me. My hypnosis was a twice a day occurrence, once during the day after lunch and another all night long as I slept. It became routine for nearly every minute of every day to be consumed with training me to be the perfect sissy. My corporate wife was a perfectionist and I could feel her supervising the training process of me each and every day.

The third month of my training had me learning all of the daily feminine actions needed by me to become a passable sissy slut. My morning routine had me arising early, showering, plugging my sissy pussy with ever larger butt plugs and then sitting down at my makeup table to turn my face into the feminine vision my wife demanded. It took nearly the entire month, but near the fourth week my skills at applying my makeup was becoming much, much better. Countless times during my cosmetics training Chrissie had roughly wiped my face with a towel and told me to begin again. A professional makeup artist assisted me with the transformation of my somewhat manly face to one that screamed femininity.

I hardly knew the person who stared back at me from the mirror once I had finished putting on my makeup every morning. My eyebrows had been shaped in a very feminine way and then, much to my chagrin, Chrissie had brought in a tattoo artist to fill in my brows and also add color to my lips. A beautiful sissy cosmetologist also worked on me, plumping up my lips with injections and filling in my cheeks to give me a sexy, pouty look.

Once my makeup was applied every morning, I would then proceed to get dressed for the day. Knowing the great taste my wife had it came as no surprise when the massive walk-in closet just off of my bedroom was filled with the most expensive, sexiest outfits imaginable. All of the items were color coded so that when dressing for the day everything matched impeccably. There were a variety of corsets. A multitude of panties, bras, hose, and garters filled all of the drawers that lined the closet. And then there were the shoes. At least twenty pairs of Christian Louboutins, another twenty pairs of Jimmy Choos and a variety of Valentinos, Guccis, and Dolce Gabbanas. There were black and pink and white with many different heel sizes and styles. Many of the pairs were of course the locking variety, insuring my feet would remain in heels until released by Chrissie.

Once dressed I would stand before Chrissie for inspection. She was also a perfectionist and many, many times I was sent back into the closet to readjust or change some item for her. Some days it was the classy business look. Other days it was a casual spandex pants and heels day. But most days my look was that of a sexy sissy, who after many months of my training, was actually giving Chrissie and the other sissy trainers a run for their money as to how hot and sexy I could look. My diet and exercise had slimmed me down and almost all of my masculine muscle mass was gone. My breasts were becoming a bit larger and my hips seemed to be slowly evolving into a very feminine look. It was never discussed with me but I was almost positive hormones were being put into my food from the very start of my incarceration. I would find myself massaging and pinching my nipples throughout the day. My clitty constantly leaked and every evening was spent hand-washing my soiled panties.

I would have the pleasure of sucking real cocks about four to five times a week. My cock sucking skills had improved tremendously and I was very adept at deep throating and orally pleasing all of the men who came to use me for my sissy abilities. Chrissie would smile with delight how I had improved and she would make sure all of my sessions were documented for my wife to see.

I had not spoken or seen my wife ever since the first few days of my arrival. So it was a huge shock when at the beginning of my sixth month that Chrissie informed me that my wife would be visiting me the following day, on my birthday. It was one thing knowing that my wife had been viewing all of my progress, but it was quite another to stand before her in my new sissy persona. I was so very nervous.

As a special treat, and to prepare me properly for my wife's visit, Chrissie had arranged for me to leave the townhouse and accompany her to a beauty parlor where I was to be, as Chrissie put it, "given the works."

I had not been allowed to leave the premises since arriving so going out was going to be a special treat for me. But my excitement was soon tempered as Chrissie was going to personally dress me for our outing.

After completing my makeup, Chrissie showed me my outfit for the day. Along with pale pink thigh-highs and a pink bra, I was literally poured into a pink micro mini skirt that was so tight and short that it made moving about quickly impossible. A short light pink blouse that exposed my new skinny tummy was given to me to wear that completed my extreme sissy look. Finally, a pair of locking five inch heels were attached to my feet.

Chrissie looked at my carefully, having me twirl for her inspection.

"Something is just not right," she stated.

She pulled out her cell phone, walked into the other room and all I could make out was her thanking someone and telling them she would see them soon.

Approximately twenty minutes later I was called into the living room where I saw, standing next to Chrissie, a very large man with an abundance of tattoos and piercings chatting with Chrissie.

"Oh there you are sissy. I realized what was missing to complete your look. My friend Mike is here to pierce your belly button so we can adorn it with some pretty sissy jewelry. Now come over, lie on the couch, carefully so as not to wrinkle your outfit and we will be done in a jiffy."

This was not what I was expecting. For the first time in many months I almost began to protest but the thought quickly left my mind and I minced over to the couch and carefully laid down. Mike was already prepared. Cool alcohol was applied to my belly button and the needle was unceremoniously shot into me. Before I knew it a pink jewel was dangling from the tummy.

Chrissie squealed in delight. "Oh yes, much better. Look how cute it is sissy. Now everyone will definitely know your sissy status. And I just had another thought. While Mike is here let's get those little sensitive nipples of yours pierced also. It will save Mike a trip. Right Mike?"

Mike nodded in agreement and before I knew it I was now sitting up and Chrissie had removed my blouse and bra. Each nipple was pierced and a small ring was attached to them. They were stinging from the needles but Mike assured Chrissie that in a few days the soreness would be gone and they would be ready to be pulled on and abused.

"What do you say sissy?"

"Thank you Master Mike," I replied. "May I suck your cock in appreciation for the piercings?"

Chrissie squealed with delight again. "Oh sissy, I am so proud of you. But unfortunately we do not have time for your makeup to get ruined by you sucking Mike's big cock. But we will take a rain check and Mike can come back anytime to use you for his pleasure. Now let's get going!"

Once my bra and blouse were back in place, Chrissie buckled and locked a pink sissy collar around my neck and attached a pink leash to it. As she tugged slightly, I followed behind her as we made our way to the elevator. I began to panic, suddenly realizing that I was going to be taken out into the public dressed in the most sissy way imaginable. My knees literally began to shake as Chrissie pulled me into the lift after inserting her key card into the slot.

Reaching for my chin with her perfectly manicured nails, Chrissie made it very apparent to me that she expected me to be on my very best behavior, or else!

Thankfully the elevator went directly down to the parking garage where a large black SUV was waiting for us. Another gorgeous sissy, or at least I assumed she was a sissy, held the door open as Chrissie entered first and then tugged me along beside of her. The windows were all blacked out so I had no idea where we were going. As we drove off Chrissie tapped and played with the jewel hanging from my tummy, eliciting an arousal in me that had me leaking immediately.

Upon noticing this, Chrissie whispered seductively in my ear. "You know sissy the more feminine you have become the more attractive to me you are also becoming. Be a good girl and perhaps soon you will have some special play time with me. Imagine, two sexy sissies playing with one another. Would you like that?"

I could only nod, being at a loss for words.

Before I knew it we were coming to a stop and the back door on Chrissie's side was opened. The bright sunlight made me squint and as I was being pulled out of the car I nearly tripped and fell.

"Follow close behind me slut," Chrissie said. "Everyone who now sees you will realize that you are an owned sissy bitch ready to please. Do me proud, show me how all of that high heel training is paying off. Swish those hips as you walk. "

With the restrictive tight skirt I minced gingerly behind Chrissie, making sure to strut my stuff as well as I could. The skirt was so short that anyone walking behind me would have a lovely view of my pink panty clad ass. It seemed both men and women were staring at me. Many of the guys smiled as they walked by and this actually was quite arousing to me.

"Looks like you are making quite an impression my little sissy. Have you noticed those horny men ogling at you?"

"Yes Mistress Chrissie," I replied in my girlie voice.

After walking for about half a block we came to a salon which had some fancy French name which I really cannot remember. The huge glass doors were pulled open for us by two extremely handsome young men and I followed Chrissie up to the front counter. From somewhere behind a wall, a strikingly beautiful blonde came forward and greeted Chrissie with a huge hug and a sensuous kiss on the lips. They chatted for a few moments and soon another woman, quite a bit older than the first, came out and Chrissie handed her my leash.

She tugged me along and I followed her back into the salon where she instructed me to sit in one of the chairs facing a mirror.

"Well let's see what we have here. I was told that you have been letting your hair grow out, but Jesus girl, what a fucking mess. We really are going to give you the works and turn you into a sexy bimbo looking creature. Now let's get this cover up on you so we won't ruin that cute blouse and I will start with washing that mop on top on your head."

And so my day at the salon began. My hair was washed, cut, dyed and then blown dry. When I was allowed a look, I was shocked. A cute blonde with a sexy bob haircut that sported streaks of pink was looking back at me. I hardly recognized myself and all vestiges of my masculinity had been now wiped away. I was so fucking sexy!

Next came my manicure and pedicure which was followed by a bright pink coat of nail polish on both my feet and hands. Nail extensions had been glued on my fingers and my pink polish made them a model of femininity. My lipstick was replaced with a new color which matched my nails perfectly.

And as I stood up and checked out the new me, I reflected on what had occurred to me in the first six months of my training. I was now a hairless, skinny sissy girl with a cute blond hairdo. I was an expert at applying makeup and walked in heels like I had been doing it for years. I craved cock and loved pleasing men with my mouth. I had not been allowed a male orgasm in six months and my penis was definitely shrinking but continuously leaked sissy juice into my panties. I felt empty without a butt plug inserted in my boipussy and looked forward to kneeling before Chrissie and kissing her heels while thanking her for my training every morning and evening. I had resigned myself to the fact that I now wanted to be the best possible, sexiest sissy I could be to make both Chrissie and my wife proud. My nipples and belly button were pierced and my skin was soft and supple.

There was no going back but there was also more training to complete. Chrissie had told me that pussy training would commence soon, as well as cunnilingus training. She explained that a perfect sissy needed to be able to please both sexes and that meant becoming an expert at pussy and ass eating. And of course a perfect sissy needed to be able to take large cocks in all of her holes. Up to this point my boipussy had only been stretched daily with the butt plugs and I had yet to experience being fucked like a real girl. Chrissie had told me about sissygasms and I was looking forward to eventually being able to have one from being fucked in the ass.

"My oh my who is this hot little bitch?" Chrissie's voice interrupted my daydreaming. "You look good enough to eat my sexy sissy. Such a wonderful job they did on you. You are now a femme sissy bitch who just looks likes she is ready to be used. I hope you like the new you?"

"Oh God," I gushed just like a little girl. "I love it Mistress Chrissie. Thank you so much."

And right there in front of everyone I carefully kneeled down and kissed her heels.

"Okay sweetie let's get going," Chrissie stated as she tugged me up by my leash and started walking out of the salon. There were a few cat calls as we left and I was, for the very first time, proud of my newfound sissy persona.

Once back in the SUV, Chrissie tugged sharply on my leash and brought my face right up to hers. She seductively began kissing me on the lips and I was melting right there. My moaning began with her first kiss and was never ending. She was so damn sexy and I had secretly lusted after her from the moment we first met. And now, knowing that she was also caged and a sissy just like me made it even better. Our tongues danced in each other's mouths all the way back to the residence. When she kissed my neck and gingerly tugged on one of my nipple rings I thought I was going to faint. She had me pull down my panties and lift my skirt so she could fondle my ever shrinking balls. Her touch was like a magic wand, flowing over and through me with a sensuality that I had never experienced before. She fed me my pre-cum as it flowed down over my balls. I sucked at her fingers ravenously with a reckless abandon.

And then she whispered to me again. "You see sissy, there are many heights of ecstasy that a sissy can and will achieve. As long as one understand that the pleasures of others always comes first. You will forget and never miss your old male orgasms. You are past the point where you will ever be allowed another one anyway. And you will not miss it. And as your anal training begins in earnest I will have the extreme pleasure of fucking you into oblivion. Oh no, sissy, not with my baby cock. Oh no. You will be on the receiving end of many sizes of cocks and dildos and eventually will have a real cock fuck your pussy. And if I train you correctly, that elusive sissygasm will raise up inside of you and your world will explode. And you will love me dearly for taking you on this journey."

I was crying softly, surprising myself. I buried my head on her shoulder as she continued to fondle me. I never wanted it to end, this moment of such clarity and desire.

( Chrissie was enamored with the little sissy slut but knew that she would not be allowed to play with her unless her Mistress gave her permission. The desire was there but she knew better than to push the envelope.)

Before I knew it the car had pulled to a stop again and I was sorry that I had to leave the sensuous shoulder of Chrissie. Pulled out of the car once again by the leash, we were in the deserted parking garage. The beautiful driver had once again opened the car door for us and stood invitingly as we exited.

Chrissie asked me, "Well sissy, did you enjoy the ride?"

"Yes, very much so," I answered.

"And have you totally forgotten your manners? Our driver did an excellent job and yet you have not yet offered to thank her. Do you think that is appropriate behavior for a sissy slut?"

"I am sorry Mistress Chrissie."

Chrissie gave me a look of, "so now what?"

I looked over to the driver, looked her directly in her lovely blue eyes and asked her if I could please her in some way for the great job she did.

Without uttering a word, she unzipped her spandex bottoms and slid them down so that her cute, free clitty swung seductively in front of me.

Remembering how to squat without letting my knees touch the garage floor, I got into position and looked up to the sexy sissy in front of me, asking with my wanton expression if she would allow me the pleasure of taking her into my mouth.

She smiled and nodded. While still being held by Chrissie, I lightly flicked my tongue over the head of the driver's clitty. This was very different than how the masculine cocks I had sucked seemed to react. With a slight purring noise, I looked up to see her close her eyes and tilt her head back in ecstasy.

"She hasn't cum in over a month sissy. I expect you to tease her endlessly with your mouth and tongue and make sure she enjoys a very long blow job from you. Remember, this is a girl you are sucking so I expect you to be gentle but naughty. Understood?"

Chrissie pulled the leash taught as she finished her instructions and I nodded immediately that I understood what she expected of me.

I slowly began my oral ministrations, lapping up the pre-cum and savoring the wonderful taste. I held her little balls in my hands and took her clitty in my mouth. As it expanded to it's very small size, I realized how much I could do with such a small appendage in my mouth. I licked it with my tongue and would then suck it, moving my lips up and down the tiny shaft. I thought it was like savoring a popsicle, only this was hot and savory. I tickled her balls as I teased her and a few times I thought she was going to fall off of her six inch heels. Thankfully, her back was resting on the side of the SUV so as I continued to suck and lick her she had a way to keep from falling. Such effeminate noises were coming out of her red lipsticked mouth as I continued sucking her in and out of my hole so that it felt like I was sucking a woman's clit rather than another sissy's clitty. I was really aroused by the scene before me and I took great care to make sure the blow job lasted an inordinate amount of time. I had coated her entirely with my saliva and the little clitty slid easily up and down my mouth. There was not much to deep throat, but I sucked her in all the way and was actually able to get her balls in my mouth at the same time. She and I were in heaven.

I could feel the tiny clitty harden even more and I suddenly heard my luscious partner begging Chrissie to allow her to cum. She had no doubt been trained so well that she could and would not cum unless given permission. I was awestruck by the discipline she had, knowing that she had not cum in over a month and that my oral skills were driving her crazy. The begging was beginning to turn into an animalistic sobbing and as I continued sucking her into my throat I had a feeling she was ready to pass out if not given the permission she was begging for.

I released her from my throat, but continued sucking up and down while keeping her in my mouth. Her uncontrollable moaning and begging was a tremendous turn on for me, knowing that my cock sucking skills could elicit such pleasure.

Finally Chrissie spoke. "What do you think my sissy cock sucker? Should I allow our luscious driver to cum in your slutty mouth? I think she is so ready and I think we have teased her long enough. Now when I snap your leash take her all the way down your throat and hold her there. Keep sucking but do not remove her from your mouth. I want all of her sissy juice to go directly into you. Understood?"