Sissy Baby Story
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Sissy Baby Story
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Turned Into A Sissy Baby I was terrified at the prospect of being turned into a girl. I mean it’s one thing to do it alone in your bedroom from time to time but another thing entirely to have beautiful women see you in a dress. I don’t think that’s the best way to get girls. But due to hard times I needed a place to stay and some extra money. A group of experts were offering big bucks (like 25 million) to a group of men with different views of womanhood and feminization. I was lucky enough to be chosen. So I packed a bag with all my essentials and hopped a private jet to an even more private island over 20 hours away where my transformation would be taking place. The only building on this island was a gigantic castle. With all its separate towers and turrets it was far more than any princess would dare to dream of. I was led into the main entryway by a man (surprisingly) then 2 tall and extremely attractive brunettes who looked about in their twenties took me down a series of hallways so vast I’d never be able to find my own way out. Clearly some of the men here tried to escape in the past. I was at last brought into a master bedroom of bright magenta walls with white trimming and carpeting. A big bay window looked over the grounds and there was a giant canopy bed in the middle of the room hung with white lace and covered in pink satiny sheets. Also a large vanity complete with a professional chair, sink and tub was over in the corner. Double doors opened to what I assumed was a closet and a door off to the side which could only lead to a bathroom. I was so taken aback by the immediate girlishness of the room I didn’t even notice the three women who occupied it. One had black hair and was hovering around the vanity, the other had red hair and stood near the closet, and the last was a blonde who sat on the bed. They were all exquisite, subtly beautiful. “Well, well, well. It looks as though the girl of the hour has finally arrived!” exclaimed the blonde. I noticed she was probably in her mid to late forties. A definite milf. “Now don’t just stand there girl! Take your clothes off for us!” For the record let me just say that I’m a 5’10 guy with shortish brown hair and a pretty thick build. By no stretch of the imagination was I a girl….yet. I stood there awkwardly and she said in a softer tone, “No need to be nervous dear. We won’t judge a thing.” Surprisingly I believed her. I trusted her for some reason and I stripped naked, slowly, in front of them, feeling like I’d never be the man I was now again. “There we are darling. Now don’t you feel better already getting rid of your old clothes? They did nothing to show off your girlish, curvy figure at all!” Girly figure? Hardly. “Now then dear, before we begin I want to be absolutely sure you know what you’ve gotten yourself into. We are transforming you into a lovely little 4 year old girl named Sally, and you will need to relearn everything you’ve known. We are essentially building you back up fresh from scratch. Are you ready to be turned into my beautiful little girl?” For 25 mil? Absolutely. Turn me into a damn pigeon for all I care. “I’m ready.” “Ah, ah, ah say it correctly dear. And from here on out you’ll be referring to me as mommy,” she said with a smirk. Well that sounded kind of stupid but alright. “I’m ready to be turned into your little girl mommy.” “Hmmmm, well you don’t sound much like a little girl to me. Higher darling, much, much higher.” Feeling very stupid now, but also wanting to please “mommy” I said in a near impossible pitch of falsetto, “Yes mommy I really want to be transformed into your pretty little girly girl.” “Excellent Sally, excellent! Now sissy is going to take you into the tub and shave you bare and then the really fun part begins! See you in a little while sweetie!” The red headed girl led me into the bathroom which was done completely in lavender. There was a smaller vanity in here with a high chair and an enormous shower, also (strangely) containing a chair, with restraints on it. “In you go Sally.” Sissy said. She had a surprisingly husky voice. She strapped me into the chair feet first, then my arms. My neck, luckily, was kept free. “Just a precaution honey, try to enjoy it.” She turned the shower head on which doused me in refreshing warm water. When I was finally good and soaked she slathered me in a sweet smelling body wash and began shaving my toes. That was kind of embarrassing. I didn’t even realize I had hair there. Next she began shaving my legs very slowly. I became a bit scared when I saw how feminine my legs looked hairless but tried my best to think about the big payoff. Next she moved to my penis, chest, then my arms, then my armpits. Finally I was completely shaven and my skin felt silky smooth. It was pretty sickening. “Very good Sally,” Sissy encouraged as she undid my restraints. “Come here and let me dry you off.” She dried me very slowly and took her time around my newly shaved penis clearly making sure she hadn’t missed a spot. I was beginning to get a raging erection from all her fondling, but she acted as though she didn’t notice. Thank god. She hung the towel up to dry then headed me back into the bedroom. “Lie down on the floor sweetie, and we’ll get you all diapered up.” Did she say diaper? “Oh darling we have to take care of that now don’t we?” Mommy said as she walked back into the room eyeing my erection. “Keep that thing it a cage. Sissy give him a chastity before his diapering.” “Wha- bu-,” I sputtered. “I thought I was being turned into a girl. I don’t want diapers or a chastity!” “Ah, ah, ah Sally. We don’t want a spanking do we?” Mommy asked as she produced a large and menacing looking whip. No we didn’t want that. My erection died as my manhood was packed away into a tiny pink chastity with a big silk bow on it hiding my penis entirely. If anyone were to see me they would clearly think there was nothing there. Sissy then pulled out a bottle of baby powder and powdered the area around the chastity. “Flip over sweetie,” she commanded softly. I flipped. I didn’t want that whip. She sprinkled the baby powder onto my bottom and again asked me to flip. Now she produced an adult sized diaper covered with little ducks. She lifted my legs into the air and put my ass on top of the diaper. She folded it up over my little bow so it was finally out of sight, and then did up the sides. And boom I was in a diaper. “Let’s take a look in the mirror shall we Sally?” and with that mommy pulled me to my feet and flung open the closet doors which revealed girly dresses and ballet shoes galore. She stood me in front of the full length mirror and chained my feet and arms behind me so I couldn’t move and I was forced to look at myself. “How do you feel Sally?” “Ridiculous,” I choked out in my falsetto voice. “Well then you’re just going to have to stand there until you learn to appreciate your diaper and your new self a bit more. I was left there for about five minutes standing face to face with what I had become. When she finally came back I was ready to do anything to get away from that mirror. “Shake your little bottom Sally.” I wiggled my hips around as best I could. “How does that feel?” “I feel like a baby girl mommy.” “And that’s exactly what you are.” She unhooked me and led me over to the vanity chair. “Now it’s time to sit back and relax darling. Cuzzie (apparently that was the black haired one) will be giving you a manicure and pedicure while I work on your hair. I’ll be giving you a head full blonde curls!” Oh joy unbounded. I took my seat cautiously. It was petrifying to be demasculized like this. Throwing away everything I was ever told. But it was also such a rush. It felt so forbidden. As Cuzzie got to work on my toes Mommy began bleaching my hair out with peroxide. “Don’t I get a wig,” I questioned softly. “Oh heavens no Sally. How could you ever be a real girl with a wig? You’re getting extensions and a perm angel. Nothing but the best for my baby doll.” Now I was getting really, really anxious and as the bleach started to burn my scalp I focused instead on my toes. Already, with no polish on them, they were much more girlish looking. Expertly manicured and lotioned. Then, just as Cuzzie started applying the purple polish my neck was forced back as my hair was washed out. I looked in the mirror to see that my locks had become white blonde. Shocking. I hardly recognized myself. Mommy then stepped in front of me with a comb and scissors. Oh no. “Hold still now Sally. Don’t fidget.” She parted my hair in three ways. Front, left, and right. Then she clipped me a set of bangs that barely brushed my eyebrows. Now I really was scared. Those bangs made me look like a little girl. There was certainly no going back now. She began threading the extensions through as Cuzzie moved to my hands. She was applying neat little tips which I could already tell were going to get in the way of even the simplest tasks. By the time she was finished painting them a dark lavender mommy had finished my extensions. My head felt much heavier. And yet it became heavier still as she started expertly knotting my new hair around little curlers. Hundreds of them it seemed. “Oh Sally,” she gushed as she worked. “You are going to be such a pretty little girl! I can’t wait to get you into your big poofy dress. And just wait until we get your hair set in matching piggie tails and little bows!” That sentence just about drove me wild. After my hair was all set up in the curlers, Sissy waxed my eyebrows into teeny tiny arches. It hurt so bad I started to whimper. The little girl thing was already having an affect on my personality if I was sitting there whimpering rather than screaming obscenities. “Let’s get you all dolled up nice and pretty now,” mommy said as she pulled me from the chair and over to the bed. “Now sit here darling and start putting things on as I hand them to you.” The first thing she emerged with was a pair of white tights. Shockingly, they were large enough to fit me, diapers and all, but didn’t sag in any spots. As I slid them up my now hairless legs I really did start to feel like a girl. “Oh don’t you look adorable in your little tights! They show off your legs so well!” The next thing she came out with was a set of gigantic petticoats. They looked like they were made for a giants daughter. This was it. The part where the real girlishness kicks in. I slip the petticoats up my tighted legs and set them between my waist and my navel. They stuck out two feet wide in all directions. I was aroused. “Why you look like a little ballerina darling! But no little girl is complete without her corset. I’ll have to do this for you sweetie.” She walked over carrying a white corset and put it over my chest then started tying it tightly in the back. “Of course we’ll have to pull it tighter and tighter in the following days but for now I think this is a good place to start. Are you comfortable sweetheart?” “Yes mommy, I’m fine,” I squeaked. Finally it was time for the dress. Mommy pulled it from the closet with a flourish and slipped it on over my head then zippered up the back. It was a bright pink color with huge poofy sleeves. The petticoats had it jutting out so that my diaper was only just visible. It felt….amazing. “Oh look at my pretty little girl! You look so adorable in your poofy dress and tights! Are you ready for your shoes?” “Yes mommy!” It frightened me of how accepting I was of my transformation but I felt so pretty and girlish I wanted nothing more in the world. She handed me a pair of shiny black tap shoes that fit me like a dream. “Swish your dress around like a good little girl for mommy.” I started swishing my hips to the left and right, fingering the bottom of my dress. “What a good little baby doll you are! Now turn around and touch your toes with your legs together so mommy and sissy and cuzzie can all get a look at that cute little diaper you have on!” I eagerly turned around and showed them all my bottom. They all laughed with glee. “Oh how adorable is she! Look at that little blush!” “Speaking of blush,” mommy said “it’s time to finish up her hair and get started on her makeup. Come on my little Sally, back over to the vanity! And this time lift your skirts before you sit down.” I made my way over slowly as my petticoats and dress swished with every little movement. I did exactly as she said and slowly took my seat. Sissy began taking out my curlers and once all my hair had come down I was spun around to face the mirror. My curly blonde hair hung past my shoulders and was curled to perfection. I was a baby girl. Mommy took her comb and made a straight line down the center of my scalp. She took one side and brushed it up as high as it would go, almost to the top of my head. She knotted it there with a plain white hair tie and repeated the process on the other side. She used a round brush to swoop my bangs down then curled them under. At last she added two big bows to the tops of my pigtails. “Oh look how cute my little daughter is! Wiggle your head back and forth for mommy. Let me see those pigtails bounce up and down!” Loving all of the attention I jangled my head back and forth with a little giggle. “Atta girl! Now there’s just one thing missing. Every pretty girl wears dangly earrings to frame their face. Hold still baby and this won’t hurt a bit.” I got a bit scared when I saw the needle but surprisingly when she pulled the needle in and out of each ear followed by huge pink sparkly heart earrings I felt no pain. Just some additional added weight. “Now wiggle your head like a cute little girl for me baby. And do that darling giggle again.” I shook my head with added vigor giggling loudly and playing with my pig tails. My actions were getting me more aroused than I had ever been in my life! “Oh Sally you’ve been such a good little girl for mommy through all this! Let’s practice a few poses. I want you to skip across the bedroom for me. Let me hear that cute little giggle once more.” I stood slowly and ruffled out my pretty pink dress then shook my bottom. It made sissy and cuzzie laugh and I started to giggle uncontrollably. I started skipping across the room. “Very good Sally! Now come back to the middle of the room and give us all a nice little curtsey.” I pinched my dress between my fingers, crossed my feet at the ankles and bent my knees forward. “Perfect darling! I’m pleasantly surprised that I don’t need to teach you anything about your form. Something tells me you were fond of playing dress up!” At that I felt my cheeks brighten again. I’d never blushed this much in my life. “Oh heavens dear I almost forgot your makeup! You look so girlish even with nothing on! Come sit down.” Cuzzie came over and started applying my makeup. She put on a cover up and foundation, then pale pink lipstick covered by a shimmery gloss. A lot of blush. My cheeks were now permanently rosy red. Bright blue sparkly eye shadow and a ton of mascara that made my eyelashes about an inch long! I looked like a gorgeous beautiful girly girl baby doll. Then mommy gave me a fuzzy pink purse and said we were going to run to the store. “But everyone will see me mommy!” I immediately protested. “Why of course dear that’s the point! You’ve been so good Sally don’t start fussing now. I don’t want to have to spank you.” And I could tell from her tone and her eyes that she meant it. “Okay mommy lets go.” “That’s my girl!” I was led down a different set of hallways and out of the back of the castle this time to an expensive looking convertible. I made my way to the passenger side but then mommy stopped me. “No one under twelve in the front seat silly. Come on I’ll strap you into your car seat.” “But mommy!” I fought. “It’s the law,” she said shortly. Grumbling, I scooted myself into the large car seat and allowed her to snap me in extra tight so I couldn’t move a muscle. “Feel free to have a little fun back here sweetie,” she said with a wink. Ah very clever. The car seat was like a type of bondage. I could feel the tingling between my legs and began to think all the things I needed to too get me aroused. You’re dressed like a baby girl. You’re wearing a diaper and a poofy pink dress. Your hair is set in curly pigtails with cute little bows! You look absolutely ridiculous and now are going to be humiliated further being put on display like this. My penis was aching with pleasure at all this but the chastity prevented an erection so I just squirmed and moaned a lot. Mommy either couldn’t hear me over the wind or pretended to be unaware. By the time we reached the downtown area I was exhausted from my ‘masturbation’ session and did not protest to having to sit in the (modified) seat of a shopping cart with my feet and hands chained down. This area was bustling as if everyone from the castle and their parents were here. Some people laughed, some awed but everyone looked at me. “Just smile sweetie. They can’t take their eyes off you because you’re such a pretty little girl.” “What are we here for mommy?” I was surprised there would be anything here that wasn’t already in the castle. “We’re going to get you your own stroller honey! A reward for doing so well today. And maybe we can get you a cute little bonnet too for your extra effort!” “Okay mommy,” I said dejectedly. I wasn’t having much fun anymore. “Oh you’ll cheer up once we get to the store.” And shockingly the second we got inside I felt the excitement return. There were all sorts of baby girl things in here. “Mommy can I get down and look?” “Ah, ah Sally. I need to keep my eye on you.” All around me were men and boys dressed up like girls. Some babies, some in their seventies. All in very feminine baby attire. “What do you think of this one Sally?” I looked to where she was eyeing and saw a frilly pink stroller loaded up with white restraints. “Can I play in it like I did in the car seat?” “If you listen to mommy then you can sweetie!” “Okay! I’d love it please mommy!” “Excellent.” Mommy started pushing the cart and stroller up to the register. “I have to use their bathroom, can I get down?” With a laugh that made me feel as though I wasn’t in to anything good mommy replied, “Oh honey, you’re a baby girl! That’s what the diaper is for.” “I can’t go to the bathroom in a diaper!” “Ah, ah, ah, it’s called potty Sally, and you’ll just have to get used to it. Now which will it be? Hold it in and get yourself sick and spanked or go now?” With a sigh I gave in. “I’ll go mommy.” “That’s my pretty baby girl.” I had no choice. I had to take a **** right then and there sitting in the shopping cart, chained in, in my diaper. A wiz too which was no easy task with that chastity. As mommy finished up paying for my new stroller she kindly asked the cashier if we could use their bathroom. “My daughter here needs a diaper change,” she said motioning over to me. I put my head down and blushed fiercely as the girl took me in. “Sure,” she said not looking surprised at all by my appearance. “In the back and to the left.” With a thank you Mommy finally unlatched me from the shopping cart and pushed the stroller into the back leaving the shopping cart up front. She was carrying a diaper bag which I hadn’t need until now. I felt extremely uncomfortable. The bathroom consisted of 5 long rows all carpeted with doors and mirrors. More of a dressing room than a bathroom. Only differenc
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