Chapter Five – Indoctrination and New Rules

Corporate Ambitions

Indoctrination – New Rules

When the car stopped in front of the mansion, Janie once again opened the door of the limo for me and took my hand to help me from the car. She again smiled when she caught a glimpse of my pink panties peeking from under my dress. She smiled, saying “You are such a sweet sissy, tease you are,” and gave me a little peck on the cheek. She held my arm as we walked to the door, I think she could tell that I was extremely nervous and she tried to reassure me. Walking through the front door and into the foyer I was startled to hear two pairs of high heels clicking on the marble floor, Janie’s and MINE! She left me standing in the foyer to summon Ms. Williams.

While standing there I though of my options. I could turn and run out the door and escape. But reality took over, where could I co dressed like I was? Police? No, I think not. I would probably get arrested or worse. I could not do much, I didn’t even have my clothes or my wallet, and even if I did, I was broke anyhow.

I was wrenched from my thoughts by the sound of a hearty woman’s voice. It was Rebecca! How could I face her?

“My, my, my, how the mighty have fallen! Don’t you look like the sexiest sissy girl in the world? Janie has done wonders with you, even better than I had expected. How do you feel now, ‘Mr. Smith’?”

Ms. Williams had seen me, it was all out now. The way she looked at me made me feel like a mouse about to be devoured by a cat. I wanted to melt into liquid and run through some imagined crack in the floors of the opulent apartment.

Rebecca just strode gracefully toward me, and held my shoulders to kiss me firmly on the lips, her tongue sliding into my mouth like she had always greeted me this way. I parted my lips and took her tongue into my mouth as though it was the most natural thing in the world. My knees became rubber, and before I knew it I was leaning full against her strong, statuesque body, my hands sliding up her back. Her breasts were pushing into my breasts and she reached behind me, she grabbed my ass and pulled me into her crotch. I was sure that I would rip the cache panty with my excitement, or worse yet, fill my panties with my cream. Finally, released from our passionate kiss, I got a chance to see her.

I knew she was beautiful, yet I had never seen her dressed like she was now: pure feminine power. She wore a royal blue see-through, long gown and underneath, the prettiest lingerie I had ever seen. She had a royal blue, satin shelf bra, which held her hard nipples up invitingly. The matching panties and garter belt were barely visible, and her dark hose ran down her long legs like a river to pools which were perfectly matched 3″ high heels. Gazing at her panties I could see the outline of her pussy, and it appeared to me that there was a damp spot at the “v” of her legs. She was absolutely gorgeous and I wanted her. Then I remembered the way that I was dressed and how my cock was trapped between my legs! Why me?

Rebecca dismissed Janie, each exchanging shrewd smiles. Then we were alone. “Well, ‘Heather’, I’m glad to see you have taken such an interest in our products,” Rebecca mused. I was speechless. All I could think about was how I was a man and that I was now standing before the CEO of a major corporation in a dress! Oh, how would I ever live it down?

“I can explain…” I started. But Rebecca dismissed the notion with a wave of her hand. “No, let me explain,” she declared with a fiery tone I hadn’t expected. “You were hand picked, Heath. Chosen carefully, by me, if you will. You are one of the brightest, and I must say looking at you now, prettiest male sissies I have ever set eyes on. But where are my manners? Please join me for dinner.”

She looked so beautiful and yet somehow Rebecca was stronger than anyone I had ever yet known. Captivated by the starkness of the contradictions that she alone embodied, I could only follow where she led. And she led me to a dining room that I can only describe as vast. There, she pulled out my chair for me and seated me like I was the lady. But Rebecca was certainly the lady here.

Soon, there appeared a lone servant girl with the first course of our meal. As the poor girl hovered about us, Rebecca started to tease her as Janie had been teasing me. “My,” Rebecca remarked, “your little titties are growing so nicely!” The servant girl blushed deeply but continued serving us.

“Now where was I?” Rebecca reflected. “Oh, yes. We at Women’s World believe that male dominance of our planet was, at a time, a necessity. However, it’s clear that since we no longer have any saber tooth tigers running around, there is no longer any need for male protection. With the end of that need, meaning the arrival of civilization, came the advent of the male’s compulsion to invent ways to make themselves remain important. More quiche dear?”

I found myself hanging on her every word. She was making sense. Lord knows everything I had learned in my MBA program made little sense to me. She went on…

“We at Women’s World, arrived at the conclusion some time ago that it is merely a process of evolution, that males eventually become subservient to females. We’re simply speeding up the process. It’s inevitable, dear, don’t you agree?”

I wanted to run! I started looking around and wondering which window I would crash through and where I would run after that. Then she reached over and put her fingers at the nape of my neck and started playing with my hair there.

“Come now, my little sissy. I’ve had reports on you all day long,” Rebecca whispered letting the nails of her other hand ride easily under my dress. She slid one hand up my stockinged leg, the other hypnotizing me at the back of my neck, and soon I found myself saying, “Yes, ma’am.”

“You love being treated this way, don’t you, Heather?” “Ooooh, yes, ma’am.”

Rebecca just grinned and cooed, “Then it’s time we put you in your place, don’t you think?”

“Ooooh, yes, ma’am.

Rebecca took me by the hand and led me to her “master suite” and shut the doors. I was enchanted by this awesome beauty, and let her take my pretty dress off with no hesitation. She looked down at the cache panty and shook her head. “Darn, we have to get rid of that. I have something quite different in mind for you, Heather.” I stood submissively as she got on her knees and pulled the tormenting panty down my legs and flung them into a corner. My cock pointed straight out, sticking practically in her face. She detached my stockings from the garter straps and slowly filtered each one down my now hairless legs. I lifted my feet, one by one, and she had my stockings in one hand while the other was stroking just behind my knees.

I could feel her breath on my cock as she said, “I wish I had a real man! I would love to suck a powerful man’s dick!” She pushed my hands behind my back and tied them together with one of my stockings. My hard cock was practically slapping the cheek of her face. “But you are not a real man, Heather. You’re just a feminine, little sissy girl!” While she said it, she was wrapping one end of the other stocking around the base of my cock and balls, tying it tightly. Then she spread the remaining silky material of the stocking out over my stiff cock, enveloping it, and pulled it down abruptly between my legs, up the crack of my ass, and secured it to the space between my tied wrists. “There,” she said in triumph, “now every time you move your hands, your sissy clit will be stroked by pretty, feminine stockings. That should keep you!”

“How does is feel to be put in your place by a woman!” I moved my hands about and sure enough, the friction of the stocking torture device on my cock and against my ass was doing its work. Soon, very soon, I fell to my knees, begging for release. “Please, ma’am, I’ll do whatever you say.”

“Yes, you will, Heather. Oh yes, you will…”

As Rebecca rose from her kneeling position I thought she would never stop rising upward. She was like an angel, floating ever upward, borne on wings of sheer pleasure. She looked down into my hungry eyes, and romance threatened to wash the moment away, eclipsing my lust- our lust, all lust.

And I felt myself falling deeply in love with her.

She took me into her arms, her fiery eyes devouring my body. I was a conquest, yet my willing passion reached a foreboding place. The look in her eyes, the way she held me. How I thought that it should be I who did these things. Still, in that moment, I gave my love over to her and surrendered totally. “I love you…” I breathed from somewhere deep within me.

It was true, I loved her from that moment, wishing that all the moments that make up time could somehow be this moment.

I knew that I wanted to be hers, to belong to her. I knew that I did belong to her now, and that somehow, she belonged to me. All other realities simply disappeared and all other things ceased to exist. I felt myself swoon. I was were I belonged and would stay forever, a sissy owned by a beautiful, dominant woman.

Suddenly I felt Rebecca’s lips on my own lips, our lipstick mingling together. She pressed her mouth hard against mine and let her tongue force it’s way deep into my mouth. She grabbed the back of my head and pressed me deeper into her lips, her other hand found its way to my ass and she pulled me into her crotch. I truly knew at that moment what it must feel like for a woman to be ravaged by her lover. The movements also caused me to move my hands and in the process stimulate my already aching cock trapped in the silk stocking. I suddenly feared that I would cum too soon and loose this moment forever.

Rebecca backed away from me and looked lovingly at me. “Do you want to be my sissy girl Heather?” I could barely mumble the word “Yes”. “If this is so, you will always be the feminine sissy that I require. You will always address me as Ms. Rebecca, unless the situation does not warrant it, which will be very seldom. You will always do what I ask without reservation or hesitation. Such actions will be dealt with by prompt discipline. Do you agree to these terms Heather?” I could only look into her eyes and nod, my voice failing me just as my cock was failing my masculinity. “A nod is not sufficient Heather,” she spoke in a firm tone. “Yes Ms. Rebecca, I agree to your terms, I want, no, need to be your feminine sissy forever.” I could not believe what my mouth was saying, it was betraying me completely. “Very well then Heather, as you wish. On your knees before me!” she commanded. I merely sank to my knees in front of her, my cock bobbing in the silk cage she had placed it in.

She turned and went to her vanity, her back to me for a short time. I saw her remove her transparent gown and let it fall. I stared at the beautiful sight of her lean shoulders and tight back leading to her tight sexy ass and long lean legs. She was apparently putting something on. I didn’t have to wait for long to see what she was doing. She turned and walked to me and there it was. A long lifelike rubber dildo stretching from her loins! While the rubber cock looked out of place on her feminine body, it also looked as if it belonged on such a beautiful, powerful woman, my owner.

Ms. Rebecca walked slowly to me, her lifelike dildo swaying back and forth in front of her, much like I remembered my own doing when it was hard and I was walking towards my latest conquest. She stood before me, looking down at my feminine figure, my own cock jutting from my loins. She grabbed her cock and began to stroke it and looked at me. “If you are to be my sissy girl, one of the duties you will have is to service my hard cock on demand. Since you are no longer a man, you must begin to experience true femininity at my hands.” She took the cock and rubbed it on my cheek, then to my lips. “Kiss my cock Heather, do it now!” I tentatively kissed the tip of the hard cock in front of me. She put her hand on my head and began to push the cock towards my face. “Suck my cock, sissy girl.” I know not why, but my lips parted and I began to slowly engulf the hard, lifelike dildo in front of me. Suddenly, I felt that this was the only place for me to be and the only thing I should be doing. My masculine pride failed me completely as I took even more of Ms. Rebecca’s hard cock into my mouth, and my own cock was rock hard and leaking into the stocking tied around it.

“That’s right, sissy Heather, suck your Mistress’ hard cock. You are getting me so excited, sissy. You like to suck my cock, don’t you sissy girl?” All I could do is nod my agreement and keep sucking. She pushed the dildo deep into my mouth till I felt the pseudo balls hitting my chin. Then she began to push this mammoth cock in and out of my mouth picking up her speed as she went. Suddenly, with her cock buried deeply into my throat, she stopped and looked at me. “You are my sissy girl, aren’t you Heather?” I nodded in response, once again. “You will make a very good girl for me I am sure. But to show your obedience to me and to fulfill your femininity, I want you to get on your feet and lean over the edge of the bed, when I remove my cock from your pretty mouth. Do you understand?” Once again, I nodded my agreement as she began to pull the hard cock from my mouth. Once it was out, I reached over and kissed the tip before getting up with her assistance.

Gaining my feet, she helped me to lean over the edge of the bed on top of a big pillow that had no doubt been strategically placed there for my benefit. Bent over like I was, the stocking that bound my hands to my cock tightened cruelly. I could feel the stocking slide deep into the crack of my ass and pull mercilessly at my engorged cock. Ms. Rebecca just stood back, admiring the view for a moment. Moving behind me she rested the dildo on my exposed ass. Stroking the cheek of my ass she spoke seductively, “As a sissy girl, I think you know what comes next. All girls cherish the moment they surrender their virginity to their stronger lover. This is that moment for you, my sweet sissy. I will take your virginity if you so request, but keep in mind that once I do, you belong to me completely. I will mold you into the perfect sissy girl of my desires. Your only desire henceforth, will be to please me totally. Would you like that, Heather?” “Yes!” I moaned into the bed. “I didn’t hear you, Heather. If this is what you want, you must beg me to fuck your sissy pussy and make you mine.”

This was an extreme moment of truth, and I pondered my answer as best I could. To be taken in this way would be one thing, to surrender to it, even beg for it quite another. The considered words found their way to my lips. “Yes, Ms. Rebecca. I want to be your sissy forever. Please take my virginity, fuck my sissy pussy and make me yours.” I moaned. I couldn’t believe my ears, what was I saying? Then it struck me, I did want to belong to this powerful woman, and I did want to be hers completely.

She reached down and untied the stocking, pulling it from the crack of my ass and causing me to moan loudly. She then stepped behind me and said, “I hope your mouth got my cock lubricated enough Heather, but remember, every girl suffers a little bit of pain to achieve her womanhood.” This said, she began to push the monster cock into my tight, virgin asshole. I winced in pain as she pushed harder and harder, till suddenly the head popped into my ass. I screamed at the invasion and the pain, but she soothed me saying “go ahead, girl, scream if you must, no one will hear you but me, and the possible exception of Janie and the maid. However I would wager that Janie has the maid in a similar situation right now anyway, and I doubt they would care what was going on here. So scream if you must, sissy, but this is imperative to your becoming my sissy completely. You will come to enjoy my cock soon, even long for it.”

She pushed the invader slowly but ever deeper into my ass, and soon, much to my amazement, I began to enjoy it. The pain subsided and pleasure began to take over. Could this be true? Me, Mr. Macho just yesterday, and now enjoying being fucked in the ass by a woman while wearing frilly lingerie and makeup like a girl? Could it actually be true that I was indeed a sissy, and that this strong, beautiful woman had seen it, known it, before I even did. I didn’t know and really didn’t care, I was enjoying the feeling and knew that I would be enjoying it again and again. I could feel an orgasm building in my stomach like I had never known before.

Ms. Rebecca hastened the pace a little and soon I felt the hard cock sliding fully into my ass, the pseudo balls hitting my own on the inward stroke. I could also hear her moan as she picked up the pace. Could it be, that we would both cum at the same moment? Unexpected, she grabbed my hips tight and thrust with all her might deep into my ass and screamed a passionate scream. And I knew she was cumming! The thought that I could bring this beautiful woman to an orgasm by simply dressing in feminine clothes and letting her humiliate me in this way, took me over the edge. I began to cum like I had never cum before, almost from a place in my body I had never known existed. The silk stocking trapping my hard cock did nothing to contain my excitement, I could feel it spreading through the stocking and on the bedspread beneath me. I could also feel Ms. Rebecca spasming in her orgasm. Trying to push even more of her cock into me, even though there was no more to push. She fell over me and held me as both hers and my orgasms subsided. I reveled in the feel her hot breath on the back of my neck and her small kisses nibbling on my neck.

It was over, and I could feel her beginning to pull her cock from deep within me. Some part of me never wanted her to remove her cock from me. Sensing this she hugged me and laughed, “Not to worry my precious sissy girl, there is more of that to come.” Then I felt the cock pop from my ass to be replaced by only emptiness. She pulled me to my feet and untied the stocking from my wrists and removed the one from my now shriveling cock. Throwing them aside, she stood me up and led me toward her bathroom. “Undress me, Heather.” was all she said.

With trembling fingers I reached behind her and unhooked her bra marveling at how her breasts stayed taut and firm without the bra. Kneeling before her, I removed her heels and slid her stockings down her long lean legs. Laying them aside, I looked up right into those blue panties, only now I could easily see the outlines of her pussy as the whole front of her panties were soaked from her orgasm. I smiled to myself, knowing that I had done this to her. Placing my fingers in the waistband, I began to lower them. Slowly her wet pussy came into view, and I fought with everything the instinct to just bury my face in that pleasure spot. After taking off her panties I brought them to my face and inhaled the fragrance and then ran my tongue over them and tasted her essence. I could have died in peace right there with her panties in my hands and my tongue licking her essence. She stopped my revelry and brought me to my feet. Removing the rest of my clothing, she led me to the shower and pulled me into it with her. The warm water was wonderful and she proceeded to wash my body completely, not missing a spot. She handed me the sponge and I began to wash her body lovingly. Mine was a more thorough wash as I savored every inch of this goddess’s body, her perfect breasts, her stomach, her legs and feet, then her awesome ass and then her perfect pussy. We showered in complete silence and she didn’t say a word, just spread her legs when I kneeled and began to wash her pussy with my tongue. She pulled my head into her hot pussy while I licked her, and I thought I may suffocate as she ground her sex into my face- then, she came again!

Our shower over, I dried her off and powdered her, and she left me to do the same for myself. Smiling over her shoulder all she said was “Plenty of powder sissy, a girls best friend.” When I emerged from the bathroom she was laying in bed in the nude waiting for me. Beside her, was a pink satin baby doll nightie with matching panties, all covered in rows of delicate white lace. I did not need to ask because she pointed to the sexy clothes and said, “Your night clothes Heather. I hope you don’t mind, but I prefer to sleep in the buff, but insist on my girls being dressed appropriately for bed.” I was helplessly caught and I knew it as I let the nightie drop over my head and my now hairless torso and hips. Then came the matching panties which, with monotonous predictability, began to confer new arousal. “Horny again are we sissy girl? My, you’re a regular little sex kitten aren’t, you girl?” she said with a charming laugh. I crawled into bed next to her and she wrapped her arms around me and pulled me close. She reached up and clicked off the light, kissed me deeply again, then said, “Good night, my sweet little sissy Heather There is much for you to learn, but if you pay attention and strive for perfection, you will have a wonderful life and I know I will. You will be forever mine, sissy, and I am sure the pleasures we will share are too numerous to count.” She fell asleep with me in her arms, tweaking my hard nipples underneath the ultra feminine nightie. Sleep came hard for me that night, as I had no idea of what I had gotten myself into or what would become of me. Nor did I understand why I enjoyed it so. I realized that if I had chosen to, I could have slipped out of the house and made my escape, but there was something deep within me that forbade such a course. What would life bring me now? Finally I fell asleep, dreaming of such funny things as frilly satin and silk and all things feminine.

The End

Ready to start your training?

Submit your application today!



This sissy is finding this site to be more and more exciting, stimulating, enlightening and educational with each visit. This sissy is just discovering the value in contacting other members and discussing concerns and insights. This site is doing more… Read more “barbie”

Notify of
oldest most voted
Inline Feedbacks
View all comments