Becoming a Princess Part I

Well, I figured since I havent posted a story yet it was about time I did. This story is for the most part fiction. But has some fact in it about me as well as partly being based on an experience I once had. Some parts that are fiction will be slightly obvious. But I know some of it could work in reality even if its a little out there. I may write an “extended version” in the future. Or maybe “directors cut” would be a better term. I will be compressing the story because I think if I were to go into exact detail with every part, writing the whole thing would take me several days. And I just dont quite have the time or motivation for that. Haha. Anyways. I hope you enjoy. And as always feel free to comment.



Becoming a Princess




I walked up the front pathway of the large house. My heart in my throat. I knew I was going to be nervous. I just didnt think I would be this nervous. The time I had spent mentally preparing myself for this experience seemed to have no comforting value as I finally got to the stone porch leading to the front door. Giving myself a once over I decided I was decent enough looking.
I was dressed in what I often called my boy clothes. Though that wasnt exactly accurate. Yes the clothes could be considered masculine. But anyone on close inspection would see that my skinny jeans were obviously womens. Giving me some curve to my rather slender hips and showing off my naturally skinny waist. My shirt might seem like a normal V neck t shirt. But again, looking closer some would see that it probably dips a little lower than it should to be a shirt for a male. Not that I had anything to show off there. The shape and design of the shirt though still made me look slightly more fem.
I had gotten a few looks on the bus and even did a double take when I saw myself in the mirror. I had thought to myself that I look like a pretty boy from one of the Japanese manga's or anime's I sometimes watched with my female friends. I had always been petite and had a pretty feminine body. Even after I hit puberty and was now 21. Even when in masculine clothes or when I tried for the talk dark and handsome goth look I was still occasionally mistaken for female. And that of course, was one of the big reasons I was here.
I had started cross dressing when I was 16 in high school. Technically it was before that, because some girls clothes like pants and whatnot had just fit my slender waist better. But 16 was when I got bold. Borrowing one of my best friends clothes without her knowing. I dressed up. I still remember that being one of the first times I felt really sexy. But even so. Prancing around my room all dressed up and taking pictures from the neck down or while partly covering my face was the limit I had for the longest time. Living in a religious state, I knew it would be bad if I was found out by my f****y and religious leaders in my neighborhood.
I eventually told the friend who I had borrowed some of the clothes from. Who was very accepting. The surprise came when she told me how much the idea turned her on. We had always been best friends. But it was obvious the first time she got me all dressed up and put make up on me, that she wouldnt be able to resist. And I didnt stop her. Eventually though we went back to being just friends. She still helped me get clothes and when we were old enough started going out to clubs with me dressed up. Which is where I made my final decision that even though I liked men looking at me and knowing their desire to have me. That I really didnt want anything to do with them. I was a cross dresser. But I was definitely straight. And the experiences I had with women while dressed up were far more pleasing then when I had sex with them as a man. Finally when I turned 21 I decided to be bold. I signed up for a dating site as a cross dresser. Doing webcam shows with a mask on or with heavy make up and my almost shoulder length hair covering my face. I found my submissive side to be invigorating. And again, was a main part of what had lead me here today.
This woman had visited my webcam room almost since the day I started getting on. She didnt say anything at first. But when she eventually started talking her flattery as well as motherly concern and protectiveness drew me to her. Whenever a man would bad mouth me or start to treat me badly when I wouldnt submit to his will she would be the first to defend. And I also found out she was a partial site admin and had gotten several users banned from the site. Over the weeks we talked. I found she had a darker side, one that turned me on but also scared me at the same time. We ended up exchanging messages where she told me she wanted to do her best to make me into a real woman without any surgeries or changing my body. But she told me she wanted to teach me what it means to be a princess. That it would be hard. That I would have to submit. But that what she would teach me would please me in ways I never imagined. So I eventually agreed to meet. And here I stood standing on her porch. Realizing there was no turning back now. So taking one last breath I rang the doorbell waiting after the loud gong. And so my training began.

Day 1 of 4

She opened the door a wide smile on her face. Taking my hands in hers and doing the classic air kisses to each of my cheeks. “Welcome darling” she offered still beaming “I hope you found my house okay”. “Oh yes, it was no problem. The buses were a little confusing but I managed”. Giving me a stern look I wondered what I had said wrong. “I thought we had been over this young woman” she addressed, the use of the term young woman embarrassing, worrying, and flattering me all at the same time. “You need to address me properly, Im going to make you into a woman, a princess, and young women always do all they can to be proper”. I blushed and looked down at my feet, knowing the submissive gesture would please her “Yes ma'am, I apologize”. “Thats better” she replied using her pointer finger to tilt my face up ever so slightly. I could see her smile but not her eyes which is what I was guessing she wanted. “Now follow me” she instructed turning and entering her home. I let out another soft “Yes ma'am” and she closed the door.
After giving me the quickest tour possible she guided me to what looked like a large bedroom, informing me it was a guest room. But that the closet held all the outfits that could ever be needed. “Now, to start we are going to try and find the right personality for you to have fun in, before turning you into a princess” she let out excitedly. I looked up and smiled at her shyly. “Thank, thank you madam” I let out nervously “I would like that”. Beaming at me she opened the closet and my jaw dropped. Not only did the closest seem to be as big as the room and have normal everyday clothes. But also had some rather unique costumes and outfits that I was almost embarrassed to imagine even a woman in, and more embarrassed to imagine myself in.
“Now lets have some fun to begin, shall we”. Rummaging through everything I wasnt sure how the outfits she picked were going to lead to me becoming a princess. But I had agreed online to submit to her training and do as she said. Whether or not I became HER princess. When all was said and done she had laid out a schoolgirl uniform, a gothic l****a dress, a cheerleader outfit, and what looked like a cross between a sexy little black dress and a business dress suit. While looking at the outfits I noticed a faint tapping. Looking over to find the middle aged woman tapping her foot. “Well?” she said impatiently. “Um, very nice choices miss” I offered. She smiled and walked forward, surprising me by giving me a swift sharp slap.
“Im glad you like them, and that was part of what I was looking for. But I was also waiting for you to try them on”. Rubbing my cheek I replied “I see, Im sorry ma'am. I was going to but I dont see anywhere to change. Letting out another sigh she walked forward and I cringed expecting another slap. But this time she took me into her arms. “My dear little one, I am going to make you into a princess which. And the way I am going to do that means we are bound to get a little intimate. And me watching you change will just be the start”. I nodded and let out a muffled “Yes madam” into her breasts. She stepped back and I kept my eyes slightly downward and submissive. “Good girl, now get those rags off but dont put the clothes on just yet. There are a few little things we will need to add first to make you look and feel like a woman”. I slowly started stripping while she when back into the closet. Tossing out some shoes and coming out with a rather large box. Opening it she looked over at me. Standing naked and blushing I tried to cover my manhood and even though I had nothing to hide behind tried to hide my naked hairless body. My almost shoulder length hair hiding my face. “Well?” she said impatiently “Come over here young lady”. Doing as instructed I took small steps till standing in front of the box. Looking in I recognized some items but others I wasnt so sure of.
First she brought out a waist cincher, almost like a corstet. Looking at my waist somewhat disappointed I let out a soft sigh “I thought you liked my figure miss” I asked meekly. Standing she smiled at me and this time gave me a real kiss on my cheek. “I do my sweet, you are very feminine and I love it. But we have to make your curves look more natural. And this will also help you have the proper posture of a princess. I nodded and let her start the process of putting it on
After several minutes of inhaling and tightening she was finally satisfied. Brining me in front of a mirror. Feeling slightly lightheaded but knowing I wasnt going to pass out. I had to admit. My slender figure actually looked more like an hourglass with the use of the device. Even giving a little spin smiling at myself in the mirror. I looked at my lady and she was just beaming. I couldnt help but blush and be satisfied it pleased her so much. Realizing I was still naked though I covered my manhood. And my lady let out a giggle and a sigh. “Well come along, we still have a few more things to do before we get you dressed. And we want to have dinner before the night is over Im sure.
Stepping back over to the box she brought something out that I thought I had recognized but they didnt look quite right, along with what looked like a small tub of vasiline but had the color of make up or skin. “Breast forms?” I asked tilting my head. “Yes and no my dear” was a rather enigmatic response. “They are similar to breast forms but much more advance. The interior is silicone like breast forms. But the exterior is made of something that mimics human skin. But thats just the start. Throughout the interior there are wires and sensors. Leading to electrodes and other items that when attached to your skin will almost make you feel like the breasts are really yours. When the nipples are touched it will send impulses to you that will feel similar. Things like heat and cold with also be put through in a similar manner. And when you move and they bounce and jiggle, well, you get the idea”. All I could do was nod, I knew that my lady was well off. But to be able to afford something like that. She must be very rich. And very dedicated to her pleasures. Pointing to the the small make up tub I opened my mouth but before I could ask she answered “And this, is similar to liquid latex. It will help blend your breasts to your skin. And will help the bio electricity in your body charge the battery in your new female parts, now sit down Im going to have to put these on you”. Sitting down on the edge of the bed I let my madam get to work.
After about 30 minutes to put them on. And another 30 waiting for the liquid latex to dry. I got up to the bed and walked to the mirror. Surprised to find that the gentle movement not only tugged my chest with the weight of the breasts. But felt natural and more real than I ever expected. Gazing at the mirror I realized my error in telling my lady that a C cup would look too awkward on me. True I looked top heavy. But the corset helped for a much more natural look. Giving my breasts a squeeze together I let out a soft moan of pleasure. Blushing automatically. “Sensitive arent we” my lady said into my ear from right behind me making me jump. “Why dont you let me try, Im sure I can get you going” her husky voice stimulating almost as much as her hands and fingers as she reached around and fondled the nipples making both the ones on the forms and my own get hard. I started to get weak at the knees and my lady guided me gently over to the bed.
Laying be down and laying next to me she smiled, looking down at my erection which was now the only thing in my mind giving my gender away. She kept one hand on my breasts. The other manipulating my shaft. The two actions getting me so worked up I could barely breath. And suddenly she stopped. My 8 inch rod still in her hand. “Im sorry my sweet, but part of your training will be to have to deal with when someone gets you worked up with the smallest things and then stops”. I let out a whimper, since that was about all I could do at this point and nodded. Admitting defeat.
Looking out the window my lady let out a sigh. “Its getting too late to try on all these outfits and to find out your personality. I guess we will both change into our pajamas and just have a girls night after dinner. And we did. My gaze following her every move even with my eyes slightly downward and submissive.
Though I couldnt help but stare at her body as she changed in front of me. What some men would call a MILF. I just found as beauty. Her double D breasts and wide hips, giving way to a curvaceous behind. She wasnt quite a slender hourglass as me. But was far from overweight. Catching me staring she gave me a wink but then walked over and gave me a polite slap. Making me look down and apologize. “Im glad you like my body” she chided. “But as I said, we are teaching you what its like to be worked up and unable to do much about it, so dont think Im just going to walk around naked for you, I might have you walk naked for me if I choose. But it wont be the other way around unless I think you have earned it”. After that speech she handed me some silk pajamas to which I gladly changed.
Looking down I saw my cleavage, knowing that had I not known what it really was, I would probably mistake them for real myself. Getting aroused just looking at them. I quickly followed my madam out the door. We made dinner which she taught me about being a good cook. I listened intently for when I didnt another slap or other punishment came. Then we ate. I had always thought my manners were not too bad but apparently they left something to be desired. Earning several more scoldings and a few more slaps at the dinner table. When the food was finally gone I made sure to be a good little girl. Taking the dishes and rinsing them before putting them in the dishwasher. Earning a smile from my lady which I meekly returned.
“Now my dear, shall we go to bed” my beautiful teacher asked. I responded with a nod and a yawn, being sure to cover my mouth. Following my lady up the stairs I waited once we go to the top, eyes down waiting for direction. “Come along young lady, our bedroom is right over here”. I stopped looking up almost afraid, wondering what she was going to teach me if we were sharing a bed so soon. Stammering I tried to get out some sort of excuse “Our, um, our room, are you, are you sure its proper for a young lady like me, I mean, Im sure Im undeserving of such bedroom attention” . But I was silenced by a single finger against my lips. “Relax my sweet, Im not going to teach you the pleasures of being a female lover tonight. Its just. Although its been many years since I divorced my husband. I still do not like sl**ping alone. So tonight we just sl**p and let each others bodies give us comforting dreams”. Letting out a sigh I nodded and followed my lady. Crawling into the massive king size bed beside her. Letting her lay my head across her breasts and allowing her to wrap a single leg around me to keep me close. My own breasts pressed against her body. Both arousing and comforting as I drifted to sl**p. Wondering what the rest of my training to be a princess would bring.

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Categories: MatureShemalesTaboo
Posted by want2bespoiledutcd
1 year ago    Views: 1,588
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4 months ago
sexy
1 year ago
Fabulous. Sorry to see that you'll be shutting down your profile.
1 year ago
yes waiting for more chapters nice start.
1 year ago
Hot hot hot
1 year ago
wow Fantastic looking forward to reading the next chapters
thanks
Jay
1 year ago
nicely written and a good start for more