Janie stood in front of me for a minute with her hands on her hips and a look of triumph on her face. She seemed to be studying me. When I looked up at her, all I could remember was how soft and hot her thigh had felt under my hand just hours ago. Her face broke into a broad, pretty smile as she spoke, “What? You don’t want to run your hand up my leg and under my skirt now Mr. Macho? Or should that be Miss Sissy now? Yes, I think it is now Miss Sissy.” She said it with so much sarcasm in her voice it stung all the way to my toes.
She explained that Ms. Williams had bet that I would take the course that I had taken. And that now that I had made the choice to follow the path to being a beautiful sissy, it was her job as Ms. Williams’ “personal trainer” to ensure that I went down the road with the proper attitude, demeanor and look. Just like she had done with all the others.
That last statement sent a chill down my spine. I looked at her in shock as she went on to explain that yes, Ms. Williams had done this same thing to other males, but that was not to be my concern now. She was no longer at liberty to discuss company business with me. I was to be concerned only with the present and to simply listen closely to what she said. I was to follow her every instruction closely, from now on, as if I had any choice. “Oh, yes,” she pledged, lowering her voice, “not all go willingly. I’m glad to see you’re not one of those.”
Janie just looked down at me from her superior position and ordered me to rise and turn around. I did as she had instructed, wondering why I didn’t just revolt and tear these silly clothes off! I should be showing her I was a man, not some obedient little wimp. Yet, I seemed to just blindly follow her instructions, not even raising any objections. She pulled me closer and unzipped the dress in the back, pulling it off of my shoulders and letting it fall to the cabin floor. Next came the frilly crinoline. Suddenly I was standing there in just my stockings, panties, garter belt, bra with huge breasts jutting forward, and a pretty camisole. Seeing her in her short, tight, leather mini had also left me with a hardon that was unmistakably poking the front of my panties out. “My, don’t you look so pretty?” she teased with now familiar sarcasm.
Then before my widening eyes, she began to unbutton her satin blouse, exposing her gorgeous breasts caressed, as they were, in their lacey shelf bra. I thought they would spill out at any moment. Reaching behind her she unzipped her little mini and let it fall to the floor, leaving the unmistakable smell of leather in the air. She kicked it onto the pile with my dress and crinoline petticoat. She was wearing only the briefest of black satin panties, which she slid off of her waist and over her thighs. Looking at me she put her hands on my shoulders and pushed me to my knees. “You have made me so excited, ’Heather’, I must have some of you before we continue.” She pushed her pussy in front of my face tersely, and I could smell the musky pleasure that lay between her thighs. I leaned forward and tentatively licked her pussy. Janie moaned a little, and grabbed my head, draping one leg over my shoulder so that I nearly swallowed her hot, wet pussy whole. “Be a good little sissy bitch and lick my hot pussy, girl!” she cried. I had no choice, other than suffocation, so I obliged her demands. It occurred to me that I had no desire for another choice. I licked her till she had four orgasms, yet she was still ready for more. But she knew time was limited, and Ms. Williams was very unforgiving of tardiness.
Satisfied, she pulled away from my juice soaked mouth. My makeup, what little I was wearing, was totally messed, and my cock was throbbing and had left a huge wet spot on the front of my panties. She leaned down and gave me a deep French kiss, her tongue forcing it’s way into my mouth and seeming to penetrate me there. Her kiss was more than a mere kiss, it was like a little fuck. I felt so helpless to avoid her demanding tongue, it seemed to compel my very soul to open, widely, willingly. To submit.
I was dazed when she pulled me to my feet, and then sat in one of the comfortable chairs in the cabin, studying me again. She pulled my panties down and my maleness sprang forward, nearly hitting her in the face. Pulling them off completely she draped them over my hard cock. “My, look at your pretty little clitty. It’s is so hard and excited, did I do that to you, Heather?” I was a bit taken back by her referring to my manhood as a clitty, and my name was not “Heather”. As alarmed as I was, my urgent need was screaming from my loins and overtook any anger I may have had. Anger, you see, being mixed into the stew of emotions and physiological takings place as my poor body had endured this day was not an option.
Taking the silky panties and draping them over my hard cock, she looked in my eyes and smiled. “Does my pretty little sissy want to cum for me”? “Yes,” I mumbled. “Are you a pretty little sissy boy, who likes, no, needs to dress in pretty lingerie and dresses?” Try as I might to not admit to such a foolish thing, what she was doing to my “clitty”, I mean cock, was driving me wild. I needed to cum so badly that I just said, “Yes, I am a little sissy boy who needs to dress in silky, frilly lingerie and dresses. I want, no, need to be a girl for you. Please let me cum?!”
“Will you do what ever I may ask of you, and I mean anything, without question? And will you wear exactly what I tell you to wear? And will you always obey the women in your life, like a good little sissy girl?”
“Yes!” I screamed, “Whatever you say! Please just let me cum, PLEASE?”
“Very well then, Heather,” she smiled as she draped the silky panties over my jutting pole. She left the sexy garment hanging there over my cock like some obscene flag. “You may put these back on and cum like a girl. Use only your fingertips, like this.” I looked up at her mesmerized, as Jeanie pulled her own sexy panties on and began to rub her crotch. “Fingertips only, like this.”
I pulled the panties back on and knelt before her, watching her example. Touching my hard “clitty” with just the ends of my fingers like she was. “Oooh, Heather, doesn’t that feel good? Gently stroke your clit through the sexy fabric. MMmmm.”
It didn’t take long, especially since you consider that I had been horny and excited all day long, for me to begin to orgasm. I felt it start from somewhere deep within me, the mounting pain that longs for release, the itch that cannot be scratched. It all overtook me in a rush, and washed over me in wave after wave of sheer ecstasy. Soon, the panties were discoloring as hard spurts of cum tried with classic male arrogance to shoot through them. Janie came too, smirking at the growing wet spot at my crotch. And then I collapsed onto the floor, breathless.
When I finally regained some composure she was standing over me, having replaced her panties and bra, and she was smiling down at me. She reached a hand to me to help me to my feet and once there, she ordered me to strip completely. “We have a lot of work to do on you and not much time to get it done. Ms. Williams, your new owner expects us shortly.” I should have been alarmed, I should have been aghast at her use of the word “owner”. But I was too weak to make such objections. I felt owned.
After I had stripped completely I felt so completely helpless in front of her. She began by spreading some kind of pink lotion all over my body, which did not smell too good and soon began to burn slightly. When I questioned this Janie told me it was one of Women’s World’s latest products, intended to take all my hair off, permanently. “Have you ever seen a hairy sissy girl? We’ve developed our products, let’s say, with a certain audience in mind.”
I was to find out that this jet had all of the amenities, there was even a shower, albeit a little cold. And though I hadn’t chosen to, I was standing in the shower watching the cold water wash all the manly hair from my body, forever, according to Janie.
Stepping from the shower she stood there with a towel and patted me dry. Standing back, Janie smiled her approval at my now hairless body. I shivered in the cool air of the cabin and felt goose bumps begin to rise. Seeing her I also began to get excited again, she was so sexy again in that black leather mini-skirt. She handed me what appeared to be a heavy satin thong panty. It was a Lycra “cache panty” as she called it. She ordered me to put it on, and I once again just blindly obeyed. As I pulled it up my now hairless legs and over my hips she reached down and pulled my “clitty” between my legs and pulled the panty up tight. “We wouldn’t want a silly bulge to ruin the lines of your pretty dress, would we?” I could only shake my head no. Then Janie started in earnest. First, she handed me a pink satin garter belt, which she attached around my waist. “Pink is for girls,” she mused while hitching it behind me. Then she handed me a pair of tan silk stockings and watched as I pulled them up my new smooth legs. She watched me struggle briefly with the garter straps then came to my assistance, “I will not help you do this always, I am only helping in the name of saving time. You will learn to do all of what I will do to you by yourself and I expect you to become proficient at it!” I could only stand and watch, I wanted to break down and cry, yet I could feel myself beginning to get excited underneath the restricting cache panty.
My erection pushed harmlessly at the entrapping sheath. Janie seemed to expect this reaction and patted my crotch lightly, seeming to brag, “See? You’re all nice and flat down there. Just like all the other girls!”
Next she gave me a pair of frilly pink satin panties that hugged my bottom and waist and looked so flattering. She ran her hand up the front and smiled, “See? No nasty bulge to have to deal with, only nice and feminine.” Next she produced some breast forms and told me to lay on the couch, which I did all too willingly. I watched as she rubbed some sort of lotion into my breasts and then on the inserts themselves. I nearly passed out when she came to me and placed the inserts over my own nipples and pushed them securely in place. “Don’t move for 10 minutes while these set up, yes it is nearly permanent glue. Only Ms. Williams and I have the dissolving solution.” Then to add to my distress she smirked, and told me “These will give you that feminine shape until your real ones grow, if that is what Ms. Williams decides for you.” After the glue had set she helped me to my feet, I felt so off balance with the new weight suspended from my chest, and I could feel them vibrate or wiggle with every move I took. I got a kind of thrill from feeling it, like nothing I had ever felt before. I found myself wondering what she meant by, “until your real ones grow.” Surely, they couldn’t do that.
She had me slip my arms through a matching bustier. The bustier helped hug my waist a little and held my new breasts close, suspended straight out in front of me. Next came a matching satin slip. I was relieved to be putting this on since it offered me some sort of modesty, even though it barely cleared my pantied bottom. But when I felt the silky material floating over my thighs and ass, my cock was again straining against its luscious prison.
Next, she produced a pair of 4″ heeled stiletto shoes. The shoes were a pink patent leather with an ankle strap securing my foot to the shoe. “I can’t wear these!” I pouted. “You not only can, you will and you will always wear a high heel similar to these. How do you expect to become a perfect sissy girl for Ms. Williams if you don’t wear these pretty high heels? And besides you will learn to love them. Now sit at my vanity so that we can get your makeup done, time is running short.” I meekly stood, nearly falling in the new heels, and stepped to her vanity. Janie draped a towel over my shoulders, to keep my pretty lingerie clean, she said. “You will pay close attention to what I am doing, you will be expected to make yourself pretty by yourself after this.”
I could not believe what was happening to me! Here I was, sitting at a very sexy woman’s vanity wearing all this silky lingerie, my cock was trapped in the cache panty and I was basically sitting on it. And this gorgeous woman, who only hours ago had my hand on her shapely thigh, was putting makeup on my face telling me I would have to do this myself in the future. This could not be happening! Secretly, and deep down inside, I loved it. Did it mean I truly was a sissy? I would get out of this somehow, and rise up to be a Wall Street Wiz yet.
Unfortunately, such thoughts running through my head caused me to misappropriate my attention to what Janie was doing to me. She surprised me by suddenly she spinning me around to look in the mirror. I could not believe what I saw! There was a beautiful woman looking back at me! This could not be me, I thought, and then looking at Janie and seeing her smile of approval, I knew it not only could be, it was! I would have come on to this girl in the mirror, and she was me. In fact, I was blushing furiously to think that she was turning me on!
Grabbing my hands Janie quickly glued girlish fake fingernails to my own, about ¾” long, and painted them the same shade of pink that coated my lips. While the nail polish dried I was able to watch her get dressed again, sorry to see her cover any of her body. Regret, I was tasting it in so many ways this day.
Then she went to the closet and brought out the prettiest white satin dress, I think I have ever seen. I could tell though that it was short and tight. Standing in front of me with the dress in her hands she smiled and said, “I do think you will be the loveliest sissy girl in this dress, don’t you, sweet Heather?” I could feel the blush rise in my cheeks and much to my chagrin I could also feel my trapped cock begin to stir again in its satin prison.
Standing me up she slid the dress over my head and past my pseudo breasts to let it float down my body. I registered a nine in the Richter scale. Once it was in place she zipped up the zipper in the back and I could feel the dress wrap itself around me, it was very tight. I thrilled at the new feminine feelings, and began to fall in love with them. Taking my hand Janie led me to the full-length mirror and I could not believe what I saw, I was a beautiful woman! I could also see that if I bent over just the slightest my garters and panties would surely be seen by anyone who may be looking. I looked at my Janie with pleading eyes, “Please don’t make me wear this to Ms. Williams dinner, I don’t think she would approve.” Janie laughed and hugged me tightly and said, “Of course she will approve of you silly, sissy girl. She bought the dress especially for you.”
Just as the Lear Jet landed, Janie handed me a matching little purse. She said the purse contained all the necessary items a sissy like me would need, such as lipstick, blush, other makeup and of course a sanitary napkin, just in case, and headed toward the door with me in tow. When we got to the limo, she once again held the door, only this time the front door on the passenger’s side. I eased into the front seat as gracefully as I could even though I was sure I was giving Janie a beautiful shot of my panties while I did it. “You’ll learn,” she chuckled.
She got into the driver’s seat and patted the seat beside her and said, “Come sit beside me, pretty sissy girl!” I moved over next to her and she immediately had her hand on my stocking covered thigh and was moving it under my dress. She teased me this way all the way to Ms. Williams’ estate, knowing full well that she was putting my trapped cock through pure hell! Thankfully we arrived at the mansion before I had an accident. I never would have thought that I would be grateful to see the place where my life as I had previously known it, would end.
.. continued …