Paul's Sissy Journey Ch. 04

PROGRESS

Okay, so it has been approximately thirty days since I first came to be a virtual prisoner in a luxurious penthouse owned by my wealthy wife. My days are anything but ordinary.

After Chrissie introduced me to Alex for a cock sucking session, she went over the list she had written down regarding all the ways I needed to improve my oral servitude.

The next morning, after worshipping her heels, Chrissie had the bullet points of what needed to be improved on the big screen in the living room. For the next two weeks or so they would be a constant reminder of how I needed to get better at sucking cock.

Chrissie read them aloud.

"1. Eye contact needs to improve. Always look at the person who you are pleasing and work on a submissive, grateful demeanor. Beg for cock like it is your lifeblood, necessary for your survival."

"2. Kneeling is not the optimum position that a slut is the most provocative in. A bitch who can stay in a squat position, on heels, while sucking cock, really is showing what a good slut she really can be. This also keeps the sissy's nylons clean and free of runs."

"3. Relaxation is imperative when getting face-fucked. This is when the true submissive nature is on display."

"4. Some gagging is allowed, depending on the size of the penetrating cock. A quick gag pleases the Alpha, knowing that the sissy will struggle to swallow all of the cock. But continuous gagging is disruptive."

"5. When cumming, the Alpha needs to see the sissy gladly, even greedily, accepting the seed with a look of thankfulness on her face. If the warm gush shoots directly down the slut's throat then sissy will stay still until the Alpha removes the cock. At NO time will sissy attempt to remove the cock from her mouth herself."

"6. Cleaning and thanking the Alpha is extremely important. Cocks are to be licked clean of any remaining secretions, along with any of the slut's saliva. Only after a proper cleaning will the sissy wait for further instructions from the Alpha."

I stayed kneeling, following along. Chrissie certainly was detail oriented and I knew that she possessed many of the same traits as my perfectionist wife.

She continued. " So now my little sissy slut. Your walking in heels has improved significantly and we will be adding a new higher heel tomorrow. As for the cock sucking, 3 p.m. will be "real sucking time." You will treat whoever comes here as a dominant and you will treat them as you do me. Kissing and thanking them upon arrival as you thank me, and then begging them to allow you to fellate them. As always, I will be watching intently and taking notes. If you behave, and I see progress being made in your cock sucking skills, a milking time will be determined in order to lighten the full load of those little sissy orbs of yours. I will also be noting on the video as to how you suck all of the different sized dildos strategically placed around the penthouse. You will notice that every room has a cock and entering and leaving will require a five minute sucking session. If you look closely at the base of each phallus, there is a digital timer attached to the bottom. As you begin to suck, press the timer and do not remove your mouth until the beep goes off. This will signify that you are free to leave or enter the room. I expect you to suck all of the artificial cocks with as much gusto as the real ones. Becoming an expert at sucking cock is imperative for you being able to move on in your training. Go about your normal training today. Heel walking, porn watching and of course now the newly added part of your training, cock sucking."

I went about my business as ordered, walking continuously in heels, sucking cocks in every room and watching video after video of sissy porn. Except for eating, my life was consumed with my sissy training. I had read that men had been feminized and turned into full blown sissies in a few weeks. But now, knowing what being a proper sissy entailed I felt those stories were total bullshit.

In the living room, where I seemed to enter and exit more than any other room, contained the largest of all the cocks. A large black phallus was suctioned to the coffee table approximate 9 inches in length and really, really thick. I forced myself to squat as Chrissie had suggested as I sucked this monster. By the time 3pm came around, I had lost count of how many of the cocks I had sucked. My mouth seemed to have actually stretched out a bit, sort of like my rear sissy hole I thought.

I had just finished slurping and lasciviously sucking the living room cock when the elevator opened and in walked a tall, thin white man dressed impeccably in a suit. Next to him was another man, black and also tall.

Mr. Black spoke first. " We work for your wife over at the firm. She has offered your services as a stress reliever for all of her employees. We decided to take her up on the offer."

As he was speaking, I sashayed over and knelt before the two men, alternating kissing their shoes and thanking them for allowing me to suck their cocks.

"Me first," said Mr. Black.

Right on cue, I looked up from kissing his shoes and asked, in what I was now hearing as a more sissy voice if I could please suck his cock.

"I can't believe it," said Mr. White. " The boss told us her husband was training to be a cock loving sissy but we were a bit skeptical. But look at this bitch. Begging to suck cock."

I was mortified but also so excited. I wanted cock. I was actually beginning to crave the real thing. Was it the training? Was it the constant porn and hypnosis? Or was it the "supplements" that were added to my meals every day?

At that moment I really didn't care. Mr. Black's big cock was inches from my mouth. I was drooling like a wanton slut. My sissy life was really taking a turn.

After asking politely, I sucked him in, savoring the feel and taste of this man's gorgeous dick. Every cock so far that I had sucked was a bit different. Mr. Black was long and not as thick that I had imagined. I was licking and sucking his balls and holding his hard cock in my hand. Out of the corner of my eye I noticed Chrissie with her note pad, carefully watching my sucking technique. I swallowed Mr. Black quickly like a hungry slut. The cock hit the back of my throat but this time my gagging was under control. Mr. Black was moaning and began thrusting furiously into my mouth. I could see Mr. White with his own cock in his hand, hard and dripping, waiting his turn. The warmth and pulsing of a real cock was a welcome respite from all of my dildos.

Mr. Black now grabbed the back of my head, was shouting at me incoherently and his face fucking had me swooning with a submissive desire that was more powerful than I had experienced up to this point. My pre-cum was dripping down me and I was so turned on that I was in sissy heaven. When he came, as the shot of cum hit the back of my throat, I moaned like a bitch in heat. I was so fucking turned on that I couldn't wait to get Mr. White into my mouth. My desperation for another hard cock got the best of me and I completely forgot about cleaning Mr. Black. I leaned over and grabbed Mr. White, looking sexily into his eyes, seeing that look of approval from another masculine guy wanting my mouth on him.

Mr. White was very thick and about eight inches long. Another size, another new cock, another cock sucking experience for me. I was a bit surprised that Mr. White was completely devoid of hair and the smoothness of his cock and balls was extremely arousing to me. He also was wearing a ceramic cock ring, snugly seated at the base of his balls. As I began my sucking I realized that this was the hardest cock so far, probably the result of the cock ring. His manhood was like an iron pole, hard and slick with my saliva. I could feel every vein on his shaft as my tongue and mouth played sweet music on this exquisite penis. He was much more in control than Mr. Black, savoring my cock sucking skills and slowly pushing in and out of my mouth. It gave me the feeling that he was using my mouth just like he would fuck a vagina, taking his time with every thrust. My saliva was sloppily coating his entire shaft and balls and was spilling out down my chin.

I heard Mr. Black comment something regarding how hot this was to watch, but I was so into pleasuring Mr. White that I really did not hear or comprehend the actual words. I was a sissy dutifully pleasing her man. All my thoughts turned to making sure this was the best blow job Mr. White had ever experienced. I had been fellating cocks all day long but now I wanted my cock sucking of Mr. White to last forever. His breathing and slight moans further added to my wanton desires to please him. Was I falling in love with this man or just his cock? Maybe both.

"You are such a wonderful little sissy bitch. I can't remember ever being so hard. Keep sucking and make Daddy cum." The praise and encouragement from Mr. White pushed a new submissive button in me.

I was now intent on making love to this extremely aroused cock. This was no longer just a blow job, this was a lovemaking session that was as intense as I had ever experienced. I didn't notice the soreness in my knees, or the constant stretching of my mouth needed to fully pleasure Mr. White. There was nothing except the focusing of all my newly found skills to have Mr. White cum in my mouth. I was imagining his taste and I was craving another mouth full of a stranger's cum.

As if on cue, and with what I thought impossible, Mr. White got even harder and suddenly he was cumming, shooting copious amounts of warm cum into my sissy mouth. I savored the taste, hoping his orgasm would never stop. His knees actually buckled and he cried out with an animal like sound bellowing forth. I continued slowly sucking, vacuuming every last morsel of cum out of his dick. He remained really hard even after cumming and the cleaning of his still erect cock was a pleasure beyond belief for me. I carefully licked his balls clean and replaced this incredible man toy back into Mr. White's pants.

Both at the same time, Mr. Black and Mr. White began clapping in unison, at the time praising my cock sucking and promising to give a glowing report back to my wife. The thought excited me, knowing that my wife would be pleased by my progress.

After both men had left, Chrissie made a call on her cell phone and told me to clean up and meet her in the bedroom. Her tone had taken on a much more dominant nuance than before but I just figured she had also been caught up in the cock sucking scene moments before.

I washed my face and rinsed out my mouth, returning then to the bedroom.

Chrissie stood off to the side of the room and standing next to the bed was a rather large black man, dressed in a designer suit.

"Get on the bed slut and lay on your stomach." Chrissie ordered.

I did as I was told and almost immediately the large man was binding my hands and feet to all corners of the bed. What was happening?

Chrissie continued. "A proper sissy never forgets her place. And although I will report that your cock worshipping is improving, it really is disappointing to me that you still are a selfish bitch. Because you were so concerned with feeding your perverted desires, you totally forgot to clean Mr. Black after he came. And that, as you are well aware, is one of the first lessons taught to you by me. And watching your selfish actions shined a bad light on me sissy, because it is my responsibility to train you properly. So now, Mr. Winchester is making his first appearance in the sissy suite. He is summoned for only one reason...to punish!"

I was suddenly scared as shit. Mr. Winchester came into view at the head of the bed, now holding a wicked looking cane. He swished it in the air a few times, as if he was testing its ability to properly punish it's subject. He then moved behind me, now out of my sight and without warning the first blow hit.

( to be continued)