First Time Sissy: Chastity Feminization: 3 Stories

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Hold your head up, dear,” she asked as she tied a fancy bow under my chin. “There now, you look just adorable, Honey,” she said, her hand straightening the flared skirt of the coat. Bending, she gave me a little kiss on the cheek and opened the front door. Megan was a woman with medium hair (reaching her shoulders) and red, light green eyes and a well defined body, she seemed to do a lot of exercises, she was not much taller than Katherine, but the difference in height was noticeable. Mommy takes my hand and starts pulling me toward the living room, but halfway through I feel the discomfort in my feet increase and I fall to my knees. Knowing that Megan knew Katherine and now she knew me, as well as knowing what we were going to buy there, only made me more embarrassed in the process, but Katherine seemed so relaxed about it all. I wasn't quite sure what she meant by "THAT shape". I thought I was quite attractive and had a pretty good figure when laced tight, with my breast forms and all dressed. I didn't have long to wait as it was only a short drive before we pulled up in front of the shop that had always fascinated me with its window displays. The displays and the sign on the front of the building had caused me to stop in front many times and admire the treasures inside. Actually I had bought several items including my breasts forms there. One of my greatest fantasies had been to step through that front door and be fitted with all the products they specialized in. The sign read "Lovely Ladies Lingerie Boutique" and below the name it read "Mastectomy Products, Surgical Supports, Custom Bras and Girdles, Custom Corsetry - Corset Training Our Specialty".

I followed mommy into the living room as I crawled on the floor and she helped me into my playpen and told me to wait there while she made me a bottle of milk. I nodded at her, feeling my face burn with embarrassment, my feet aching from the shoes and my legs shaking from the vibration in my bumbum. Lea noticed how I was and said not to be nervous and she would introduce me to the other babies in the class. She took my hand and told me to sit on the floor, meanwhile Anna left the room and went to meet mommy and Christine outside. I managed to fall asleep despite the discomfort in my diaper and woke up hours later to Emily calling me, saying that it was time to wake up and that mommy would be home soon. My diaper had been wet once more while I slept and was very soaking wet. Let's see what we have to work with. Strip." Kylie was really taking control. She's a bit bigger than Cat, maybe a size 14 or so, but being about 5'10", a very nice "hour-glass" figure. Even in the awkward situation, I was still looking at her nice full breasts, and round ass in her tight jeans. "Stop ogling at me, and get those sissy clothes off NOW!". For the second time tonight, I stripped off, the only items left were my wig, cage and plug. I can feel myself getting closer with every second, my ass clenching and starting to spasm, I'm tingling everywhere, I'm sure I can hear ringing in my ears, but it's different, it's not ringing, it's keys... and I can hear voices...

When she finished saying that, she noticed my surprised expression, because she had been working from home since I arrived, so I thought she would always be home with me. This is a standalone story in the 'Sissy Life' universe. You don't need to have read any of the other stories to enjoy this one, but it does fit with those in terms of characters & themes. Consider it a 'Rogue One'. I indulged myself as much as possible without getting caught, although my mother noticed things in her drawers mussed several times and questioned me. I'm sure she suspected and probably knew for sure I had been in her things. Some time later, I started looking on reddit for women who had fetishes similar to mine about submission and domination, and I even talked to some, but one caught my attention. She lived in the neighboring state, but she had a lot in common with me which made me very interested in her. After about 2 months of talking and video calling, we decided to meet. I was still exploring it with my tongue and had decided it wasn't so bad when it started to inflate. Now I knew what the ball on the end of the one tube was attached to and what it did. The balloon continued to inflate inside my mouth, pressing my tongue tightly against the floor my mouth and filling my mouth completely and forcing my cheeks tightly against the leather helmet covering my head and face. The tubes inserted in my nostrils allowed me to breathe relatively easily and I was not actually uncomfortable but felt so isolated and vulnerable to whatever Mistress and the doctor decided to do to me, a feeling I would grow to know only too well.

My life was normal and monotonous, like that of any 26-year-old man. I went to work every day, but I didn't like my job because it paid me little and I could barely buy the things I wanted after paying the bills, so I didn't have many options for entertainment because of the money, I spent most of my free time at home. I lived alone, so my free time consisted of playing games on my computer and video games, as well as watching series and movies. I had few friends, but they were all very busy and we didn't have much time to hang out together. I was single and too introverted to go out with girls, so I spent a lot of time looking at pornography on the internet and masturbating frequently. Oh, no, you arrived at the right time. We will take you on a tour of our daycare center to see the facilities and our procedures.” Christine said.sort of receptacle designed to hold it as it didn't feel as if it were being crushed. The whole arrangement was very tight and semi-rigid and while I couldn't call it comfortable I did like the feeling. I had the feeling again that it was something I would have to get used to as it would be with me a long time. Awn, baby Laura is so cute, I see she's excited to join the others, isn't she?''. Anna said as she took my hand and led me into the room waddling after her as mommy and Christine waved me goodbye. We joked about my feminine side and the fact that I was definitely the submissive but she didn't seem to be interested in being the Dom. She never does anything halfway and now I'm sure that was the problem. She would have to be totally the Dom or not at all. I was finding that I not only wanted my body confined and restricted but I wanted it to be reshaped into a female form. I wanted to look at myself and see a woman. I hadn't admitted to myself yet that I wanted to be a woman. I just wanted to look like a woman whenever I had the opportunity. Oh my God, my little baby girl is so dirty and smelly, you must be wanting mommy to change your diaper so bad, don't you? Tell mommy how much you want a fresh diaper dear.” Written for Mistress Terra to be read out for her OnlyFans account as more of a script. The dialogue sections are marked in bold.

Fingers again gripped my now flaccid penis and something was being inserted into it. As it was pushed deeper and deeper into me the slight burning verified to me that my Foley was being replaced. The rest of the task went without incident, but I did notice that it took me more than half an hour to do; it normally took less than ten minutes. The tray was really slowing me down! Having inspected my work, my Mistress decided it was acceptable and sent me to get her a drink of water whilst she got ready for bed. When she put her finger in the crotch of my diaper, I was nervous with embarrassment and felt a pressure inside my chastity. I got erections in some weird situations, like when I felt really embarrassed or nervous for some reason. She noticed my discomfort and said: The straps holding me in the stirrups and to the table being released woke me up. Someone lifted my legs out of the stirrups and helped me into a sitting position on the end of the table. I was so exhausted I could barely sit upright but the same hands helped steady me. The gag in my mouth deflated in I felt the laces of the helmet being loosened. The strap holding the gag was released and it was pulled from my mouth and the pads covering my eyes were also released and removed. It was the nurse helping me and I could see Mistress and the doctor on the other side of the examining room talking and putting things into a medium-sized suitcase. The nurse pulled the helmet from over my head and handed it across the room to Mistress who placed it in the At this point I was already very excited and felt pre-cum running down my diaper and if mommy kept this up I would finally cum in my dirty diaper. I started to squirm even more and was about to cum when mommy turned off the vibrator and said.Inside the door the sight of all the displays took my breath away. It was a large room with displays everywhere of all types of women's foundation garments, anything and everything imaginable. My mind spun as I wondered what she planned to get for me. I wanted one of each. I tried to take it all in at once as I numbly followed Mistress across the room to where a woman stood behind a glass display case. The case was filled with artificial breast forms of all types and sizes. The woman greeted Mistress and then glanced over at me. Let's take off these shoes baby, I know you must be tired of wearing them.''. She said as she took my shoes off and helped me up and headed towards the kitchen. I felt enormous relief as I walked without these shoes.