Baby Sissy Stories

Baby Sissy Stories

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You had asked about my encounter with the Nanny lady in your last email and I'm sorry I did not get around to answering you last time. Her name is Mommy Molly and she has a playroom on the web, something like MommyMolly'sPlayroom.com, not quite sure. The rate was great, something like $30.00 for twenty minutes or so. She let me have a few extra minutes. I started out by getting dressed up in a diaper and plastic pants and my babyist baby shirt and sissy sox. Then I wet my diaper ****blush****! And then I called her while I was laying down on the bed. It was quite strange talking to ANYONE on the phone while in my diapered state, a first, for sure. But she sounded really nice right away and I liked how things went. She let me "mommy" in my diaper which I really enjoyed. I emailed her and she emailed back which was nice. She also told me about some shoulder surgery she was going to have and when, so I sent her an e-card but she never acknowledged that. You know what' funny is that I started having some attachment feelings towards her. You know, the usual kinds of issues. Fantasies like, Wow, wouldn't be great if I could visit her for two weeks and be in diapers 24/7, that kind of thing. To have her take care of me like a baby would be so.......well, you know. Do men obsess about having a woman change their diaper? Or do men just obsess about having anyone change their diaper? Would it be OK if it were a man? What if the man were dressed up like a woman in frilly clothing? Would it matter then? Lately I've been having lots of these kinds of thoughts and feelings, and I'm as straight as they come. It's like when you're a baby you don't care as much about who's male and whose female. You just want love and acceptance. Anyway, I had a good time and I'd like to do it more often but it's a bit pricey and I don't have money that I can really call my own, so I have to be very careful about things like this. I'm lucky my wife hasn't already slit my throat for buying all the baby/girly clothes I've bought in the last month. Plastic pants, bloomers, both plastic and satin, my new bonnet which you'll see (which is way too big, but that's a whole 'nother story I'll have to tell you about), a custom made bubble onesie, bras, stockings, tights, tops, pink hair bows...I'm actually wearing a purple camisole and two pairs of pink panties under my boy clothes right now. I'm just enjoying it so much! Baby lotion after I shave is an absolute must! Yesterday I didn't shave but I wanted a little more "glide" down there, so I powdered myself in the morning, just opened up my shorts and dropped a bunch of powder down there, and it was so nice to have that scent lingering around me all day. I was really quite productive and it was wonderful to have all that powder down there soothing me and feeling so babyish.

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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
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