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  1. Sissy Story Chapter 01
  2. Sissy Story Chapter 02
  3. Sissy Story Chapter 03
  4. Sissy Story Chapter 04
  5. Sissy Story Chapter 05 - Finale

Sissy Story Chapter 01

Categories Fiction, Authoritarian, Transsexual

Authror: A. N. Pervert

Published: 01 June 2017

  • Font:

Life with Mother

Mom and Dad and I were a family. My first memories were of three of us, Mom and Dad and me. We lived in wonderful big house with a pool and a maid to help with the cleaning, and men who came by to do the yard and the pool. I didn’t see it as privileged, rather as reality, but we had a lot of money. Dad left when I was six, in the summer after first grade. I cried, but it didn’t help, he left anyway. At least the yelling stopped at home. Instead, there commenced a time of Mom crying almost every night, screaming on the phone, and lawyers. I remember the lawyers coming by the house and conversations about divorce. Mom told me all about it, blow by blow. I don’t remember the details much, since I didn’t understand anything except Dad didn’t live with us anymore.

I remember her exultation and party with her friends when the divorce was final at last, after a couple of years. I was seven years old, almost eight, then. A bunch of women came over, and Mom sent me to bed and then they all drank downstairs and sat around laughing and talking. I sat at the top of the stairs and listened while Mom told her friends that she had gotten the house, the cars and alimony. I remember wondering what alimony was, and her saying, “That son of a bitch will pay alimony until I die, I’m never getting married again! And that’s in addition to the child support until David is 21 and his college!”

And the ladies laughed and clinked their glasses. I didn’t really know about the situation, it was only a bunch of words. What I did know was, for the first time in a long time, Mom was happy at least for that night, and that made me happy. As her friends left, I went back to my room and lay in my bed and listened to Mom make phone calls, sometimes crying, sometimes laughing. It was a pretty confusing time. That’s how I spent the 2nd grade the first time I took it. Mom didn’t really pay much attention to me, and my schoolwork suffered. I wasn’t surprised that year when I got held back. I remember sitting in the Principal’s office with Mom while he told us I just didn’t seem to understand the work and didn’t pay attention. What he didn’t tell Mom, and I did, was that my classmates made going to school a horrifying experience. They bullied and made fun of me relentlessly because I was small and Dad had left, and they made fun of Mom, which I didn’t tell her. I hated school.

After that, Dad never came around the house anymore. His mother and father didn’t approve of Mom, or me. I didn’t know why. I guess I always was a little bit of a momma’s boy, even when Dad lived with us, and I became a little bit more of one after Dad left. She was so beautiful. I always tried to please her and make her happy. Between school and Dad it was easy to retreat into my relationship with her, tuning out the world. I played on the computer and listened to Mom talk about things and dragged myself to school. The good part was, after all the commotion died down, Mom started paying more attention to me, which I loved.

As things do in life, we fell into a routine. We’d sit on the sofa after dinner, her drinking wine, me lying next to her with my head in her lap. She’d complain about Dad, and, alternately, compliment me on how pretty I was, how I was the bright spot in her life. These conversations were a wonderful time.

I do remember the day Mom got into a huge argument with the maid, screaming and accusing her of reporting to Paul (that was Dad) and finally firing her. I never found out what set that off. After that, we didn’t have a single maid. Mom hired a maintenance service and we had different ladies come in a couple of times a week to clean. Mostly, they didn’t speak very good English, and they paid little or no attention to me. Mom and I lived in a bubble in the house, with the occasional person drifting in and out of rooms, cleaning, fixing things or decorating. Mom loved to decorate and redecorate. In between outside people, I listened to Mom complain about the house, and Dad, and Dad’s parents, who Mom blamed for most of our problems. It wasn’t all her, though, she listened while I complained about school. We became closer. My second try at second grade was a little, but not much, better. I scraped by and got promoted, though Mom talked to me about paying attention in school.

Some of my favorite memories from this time involved Mom and I going out. I’d sit with her at her vanity while she was getting ready and we’d go out to eat and then go window-shopping in the mall. We’d do this a couple of times a week. I still have very pleasant memories of it. Mom and I would look at clothes and shoes and jewelry and furniture in the windows of the shops that always looked so bright and happy. I liked Mom getting dressed up, she always looked so pretty dressed up. I wore the clothes I usually did, but I was always clean. I’d take my bath and go down to her room in my underwear. I loved pulling a chair up beside her in her bra and panties and sitting there watching her in the mirror as she put on her makeup. She’d let me watch until she was finished and then she’d shoo me out of the room saying “it’s time to put our clothes on.” Then I’d run back to my room and get dressed and hurry back and wait outside her door until she appeared, dressed and beautiful, for our trip out. We’d walk back to her dressing table and she’d spray on some perfume then with a smile, “Close your eyes” and spray a little perfume on me. She’d then tell me how good I smelled and how much she was looking forward to our evening out. I’d tell her she looked pretty and she’d smile. We both loved this, and the couple of times a week we did it were a really special time, for a long time. It was even more special, when, every so often, while she was putting on her makeup, she’d look at me in the mirror watching her intently and then she’d put just a little touch of lipstick on me, or brush my eyelashes just like she did hers, and smile and tell me how pretty that made me. She’d then tell me to wash up, and get dressed. Most times I ‘forgot’ to wash the lipstick or mascara off, but she didn’t seem to notice.

Another favorite time was when she went to the beauty parlor. I’d go with her every Thursday, and sit quietly and reading a book, or playing a video game, while she got her hair and nails done. I loved the smells and all the women coming and going and Mom coming out, the prettiest one of them all. She’d show me her nails and ask me what I thought of her hair. My life at home became peaceful and quiet and safe, me living with my beautiful Mom.

One day when I was in the fourth grade, while Mom was drinking wine and I was next to her on the sofa with my head in her lap complaining about school and how much I hated it and she was playing with my hair looking at me. She patted my head, finally, as if she’d reached some conclusion, “You know, I think I should home school you. I’d like to find out exactly what difficulties you seem to be having in class and it’ll give me a chance to see what’s going on with you rather than just read Teacher’s reports. It will be fun. With the Internet today, I can sign you up for courses online and we can spend time together learning. What do you think of that?”

I hesitated, I definitely didn’t like school, and I didn’t have any friends, but it was part of my life. “You’ll be my teacher?” I was surprised, but a little concerned how things would be. Who has their Mom for their teacher? I was already different from all the other kids this would just be another thing. Mom replied, “Yes. It will be fun.” I told her I was worried about being different from the other kids. She reassured me by explaining that I wouldn’t be taking classes with the other kids, just the two of us together. Her logic eased my fears somewhat, and I remember thinking about Mom and me going to school alone. We didn’t really talk about it any more that night, but I thought about it a lot. I remember that night I dreamed of Mom standing over me all made up, in her high heels and smelling wonderful, and with her arms crossed, and a smile, telling me something. It was an exciting dream. Looking back on it, it was probably my first dream ever with some sexual overtones, which is why it was so memorable. There isn’t really much accounting for what goes on in a kid’s mind at the time like that when such life-changing events were happening. I do remember thinking I might enjoy the time with Mom, but, even as a kid, I remained skeptical. Mom was nothing like my teachers and I wasn’t a particularly good student. I worried that Mom wouldn’t like teaching me and it would change our relationship. Maybe she wouldn’t love me anymore, or send me away to school like I saw on TV. All in all it was, at first, just another anxiety.

That next evening, we went out to dinner, Mom took that opportunity to put a very little makeup on me, like it was a special evening. I “forgot” to wash up again, though I looked at myself in the mirror in the bathroom after I was dressed and it did look pretty girly to me. I liked it, in a way. But I was concentrating on getting finished and running down the hall so I could be at her door when she opened it. Thankfully, she said nothing at all about how I looked, just sprayed me with perfume and we went out. We went to dinner in an Italian restaurant, where I could get pizza, but where we sat at a table and were waited on. It was one of my favorite places. As we were eating, Mom asked me if I’d thought about her home schooling me. She recited a list of why it probably would be best, emphasizing that I’d like school better, I could work on things as long as I needed to understand it, and, most of all, she and I would have fun spending all that time together. It was a sort of magical moment, intoxicating, really. The evening consisted of some of my favorite things and I was excited and trying very hard not to show it. She made it so easy to agree with her. Having her home school me would be better and I guessed it would make school more fun, though I couldn’t imagine what could possibly be fun about school. “Great, it’s decided’” she smiled and everything seemed possible, even having fun at school. Anyway, school couldn’t be any worse than it already was.

It wasn’t a couple of days after that until a computer was delivered to the house by some lady, who set it up and showed me how to sign on to the online school and asked me if I had questions. She gave Mom a lot of books and then she was out of the house, like so many of the other people who invaded our space. Getting on the computer and into the online class was pretty easy so I picked it up pretty quickly. Before the lady left, she told Mom to call if she needed any help. As far as I know, Mom never called for any help.

That’s how my school started that year, in the summer. I was pretty disgusted since I was going to school over summer vacation, but Mom worked with me every day, and let me go swimming as soon as I finished the day’s lesson. She bought a couple of pretty fun games that called themselves “educational” and watched me learn how to play them on the computer. It all turned out pretty neat, a lot more fun than regular school. Every day, with Mom sitting over my shoulder and answering the few questions I had, I whizzed through lessons and then went swimming, or played on the computer and Mom and I talked about the lesson. She’d ask me about what I thought about it, and, sometimes, how I figured things out. She was always impressed, and I liked impressing her.

Mom didn’t like taking me to the barbershop so I hadn’t been in a long while, but this didn’t particularly bother me, since I didn’t like the barbershop either. The fat man who cut my hair smelled badly and the TVs were blaring some game or other on the television the whole time I was there. Mom and I never watched sports at home. So it got to where Mom trimmed my hair a little every once in a while, telling me how pretty it was. It kept getting longer though. One day, it got in my eyes while I was doing my lessons and Mom took my hair in her two hands, and pulled it back over my head and looked at me. “You need your hair fixed. Just a minute”, and she left and came back with a twist and put my hair in a knot on the top of my head, out of my eyes. I didn’t like it. It looked girly and I told her so. She smiled and didn’t say anything. She just Googled something on the computer and brought up a picture of a guy with a beard, and his hair like she had fixed mine. “A soccer player in Europe”, she said then she started getting pictures of football players and basketball players all with hair in various styles. There were movie stars and tennis players and all sorts of people with a “man bun”.

“We’ll have to get yours cut someday, I guess. But I must admit, I do like it long,” she smiled at me. I decided I liked it long, too, especially when she smiled and hugged me tight and said, “You look adorable,” and kissed me on top of the head. I went back to the computer and worked on my class but she paid as much attention to my hair as my lesson and kept on talking about it, adjusting the bun, brushing it off my ears. I liked her running her fingers through my hair and playing with my head, as I loved any attention she gave me. Finally she seemed dissatisfied with every adjustment she made until she said, in apparent frustration, “This isn’t working. We don’t want to cut your hair and it keeps getting in your eyes and looking messy. The only way we can fix this is braiding it.” And she took down the bun and braided my hair into two pigtails. I kept on working on my lesson, though my attention wandered to my hair. She noticed this, so she said “Just a second,” and she left and came back with a hand mirror and showed me my hair from the back. I thought I looked silly with a couple of braids coming over my ears and said so. She laughed, “You look absolutely adorable and I could just eat you up.” She hugged me around my shoulders, kissed me on top of the head and pulled me close, into her chest, and put her lips on my neck and blew.

I always loved this, but acted like I didn’t, “Oh, Mom.”

She replied, “I can’t help it, you’re so pretty!” So, we left the pigtails in while I worked. After my lesson I went into the bathroom to wash up for lunch and looked at myself closely. There was Mom’s lipstick on my neck and my hair was in two braided pigtails. I sort of liked it, it didn’t look too bad and nobody but Mom and I could see, maybe some maid or somebody I didn’t know, so I left them, and the lipstick. In my mind at that time, the lipstick was the important part.

When I finished washing my hands and went down to lunch she looked at me and smiled, “Give me a kiss, Cutie,” she bent down with puckered lips and I pecked at them. She’d just put on fresh lipstick and I tasted it on my lips and it excited me even more. After classes I went swimming and I honestly forgot to take my hair down. I wore pigtails all that afternoon, until I noticed them again, washing for supper, then I took them down. When I got down to eat, Mom was beautiful, she was wearing high heels and nylons and was made up and had on a dress. I was thrilled. She didn’t kiss me like she did at lunch and she frowned with her eyes smiling, “You looked so adorable in your pigtails. I hate to see you take them down. Oh well.” Our dinner was pleasant, but not as exciting as lunch, despite how Mom looked. She told me a couple of times to brush the hair out of my eyes so it didn’t get in my food, but she didn’t move to brush it back for me.

After that, it became the new routine. We’d sit at the computer, me taking classes, her braiding my hair, mostly into pigtails, and telling me what a shame it was some little girl didn’t have my beautiful hair. “Your hair does look awfully pretty in pigtails.” Now and then she’d ask me some question about my lesson but she kept playing with my hair all the time. I had to make an effort to concentrate on my work. To be fair, that was easier because schoolwork became more enjoyable, and I started making even better progress. She put a mirror on the table beside the computer where I could see myself and she could refer to it, “See, how pretty?” when she’d put some new weave in my hair.

When I did really well, sometimes Mom would buy me a game for the computer. One day she got one called Virtual Hairstyles and installed it. After class she started it up and we looked at styles together and talked about whether her hair, or my hair would look good in this one or that one. Mom selected one we both liked and had the beauty shop do her hair that way, and asked me if I liked it. As usual, I told her she was beautiful. She kissed my neck with fresh lipstick and hugged me tight. My life and expectations were changing, everything started being pleasant all the time. I liked classes and my schoolwork continued improving. My anxieties decreased and Mom and I seemed happy all the time. And my dreams, oh my dreams, with Mom playing with my hair as I worked on the computer, spraying me with perfume, and kissing my neck, telling me how pretty I was and how proud she was of me. It was very exciting.

This went on for quite a while. I got ahead of my grade level and Mom was telling me how impressive my progress was, and she was sitting with me at the computer playing with my hair and suddenly said, “You deserve a treat. Finish up with your class and I’ll put ribbons in your hair to celebrate”.

“MOM!”

She kept smiling, “Doesn’t my baby want to look adorable for Mommy?” she asked, faking that sad face with her eyes smiling and playing with my hair.

“MOM,” I protested.

She thoughtfully kept fingering my pigtails and continued, “You’ll look so cute I could probably not resist taking you out for ice cream at Soda Plaza for the rest of the celebration,” she looked at me expectantly.

I considered this. Soda Plaza had all sorts of ice cream and was fun, if a little young for me.

She kept looking at me grinning and telling me how cute I’d look and my greed for the ice cream overcame any doubts about her putting ribbons in my hair. After all, only Mom and I would see it. When she saw me hesitating, she just got up, pretending like I’d agreed, and said, “Good, it will be fun, you’ll look scrumptious. Now finish up so we can get busy.”

I fell into my lesson and finished after a few minutes. I didn’t do as well as I normally had I was so excited, but I did get finished, and passed all the tests they gave after the class and went to find Mom.

“Ah, ha, you hurried to get done. You can’t wait to look cute, can you?” Her eyes were smiling as she bent down and kissed me.

“No”, I remember saying, dreams of the soda plaza dancing in my head.

She laughed and sat me down in front of her vanity so I could see myself and she got in the chair to the side and tied bows at the end of my pigtails. Pink bows. They looked silly. She then found a big ribbon and tied a pink bow in my hair so it showed over the top of my head and over the sides. She took a mirror and showed me what it looked like from behind and she gave me the mirror with a “You try it.” I looked at the back of my head and myself in the mirror. I looked like a girl. I put the mirror down and looked at her to see if she was laughing. Instead I got, “Well, Cutie, do you think you look cute enough to get me to take you to Soda Plaza?” She cupped my chin and looked me straight in the eye.

“Yes.”

“Yes…and?” She laughed.

“Yes, ma’am.” I tried.

She pursed her lips and grinned, “Nice. But I asked you if you thought you looked cute enough.”

I answered, “Yes, I think I look cute enough.”

She laughed and hugged me and said, “I have to agree. Close your eyes.” She picked up her perfume bottle, squirted me and started out the door.

“Wait,” I wailed, “I can’t go to the Soda Plaza like this, what if someone sees me?”

She looked at me very seriously, “What would that matter? If we take it down the celebration won’t be the same.” She could see I was almost starting to cry. She hugged me and said, “OK, this is a celebration for both of us, so I tell you what though, it doesn’t have to be this time, but you ought to think about going to the mall with ribbons in your hair. We can go to one across town, if you want, and you can to wear your hair in pigtails with ribbons, and look real cute for Mommy.” She sweetened that comment with, I’d like that, a lot.”

I was a kid. Next time was in some nebulous future even though I liked the idea of Mom liking it and I was tempted but I was still afraid. I knew an “OK” would put things off and would get me the ice cream then, and the future could take care of itself. I did note how she looked at me.

She sat me back down, hugged me, kissed me again, and said, “You look so adorable,” as she took down my hair, brushing it out. She kept on saying that maybe next time I would go with pigtails and ribbons in my hair and how much fun we’d have. When she was finished she looked at the ribbons and said, “This is so much fun. It’s been a long time since I’ve had this much fun, next time will be even more fun,” she patted my head, before hugging me and we were out the door.

We went to the Soda Plaza and had a great time. For the first time I remember, Mom dawdled there sitting at a table with me, with her legs crossed. She touched me all the time and kept smiling. She even gave me a bunch of quarters and watched me play games as she sipped her drink through a straw and sat with her legs crossed outside the table. She looked beautiful. I kept on looking at her and finally just quit playing even though I had quarters left to play more. I took the remaining quarters back and told her I wanted to sit with her and just talk. She leaned over and smoothed my hair and whispered, “That is so sweet. This is a fun celebration without a doubt, but I’m thinking about how much more fun we’re going to have. I really wanted a little girl, you know. But when you came, I fell in love with you. I thought it would be fun to dress a little girl up and teach her about makeup and everything. But you are even more fun.” She brushed my hair from my eyes, “You are such a pretty boy, such a pretty boy. I’m glad my pretty boy is having fun with his Mommy.” Then she kissed me on top of my head and leaned back and smiled, “Isn’t my pretty boy having fun with his Mommy?”

I was very excited. It was no lie at all when I said, earnestly, “I’m having fun.” Mom gave me a huge smile and we talked some more, mostly about how much I brightened her life and how pleased and proud of me she was and how cute I was.

In retrospect, after all that has happened, I can look back on that and say it was the first time in an always excellent but very complicated relationship with Mom that we connected in a different, more intense way than we had before. I loved it. It was a great day, a day that has stuck in my memory.

Our routine changed. I did my lessons while Mom sat and braided my hair and had me look at myself in the mirror by the computer. We didn’t talk about the barbershop anymore and my hair got longer and longer. Mom tried all sorts of different braids and without asking started putting berets and ribbons and bows and flowers and all sorts of things in my hair while I worked and then have me inspect her work. I got more and more accustomed to it. Gradually, I ended up leaving my hair however she fixed it that day while we were at home, only taking it down at night and brushing it out. She suggested we start taking lessons on Saturday and Sunday, and I agreed so she’d fix my hair and talk to me. In this way, I got accustomed to wearing ribbons and bows in my hair and I loved the attention, I couldn’t get enough of it. While I will confess to still having some doubts at first, Mom seemed very happy and enjoyed doing it. When we went out, I took all the braids out and all the stuff, like flowers and bows, she put in my hair and we still had a good time. She did manage to remind me how cute I’d look if I just wore my hair like that all the time. But I’d run into kids from my former school at the mall every once in a while, and while we didn’t really talk, because I just wasn’t interested in them, they did see me.

But I was interested in Mom and me and what we were doing. I don’t want to leave the impression that I thought she was wearing me down, or maneuvering to get me to do something I didn’t want to do. Rather she was convincing me to believe in myself, and to let myself go and have fun.

On the way home from our little trips, Mom would chat about ‘next time’ and how much more fun we would have if I’d go out with my hair done and how much she’d enjoy it. She was convinced I’d enjoy it if I gave it a chance. I wasn’t so sure about that, but I did like the trips and fun we were having. Gradually I started to think it wouldn’t be so bad. I started asking her questions. “How do I know we won’t run into somebody we know? What if everybody thinks I am a girl? Do you really think I look pretty with my hair done up”?

Mom patiently answered all my questions with good humor. “Well, we won’t be absolutely one hundred per cent sure we won’t run into someone we know, but we could go across town where we never go and nobody knows us. And what if everybody thinks you are a girl? If you want, I can set them straight. But why would I? All they are going to see is a very pretty girl. And anyway, who cares, really? You’re still adorable whether other people think you’re a boy, or a girl”. And she’d smile and glance for a second away from the road at me and then continue, “You are the prettiest person in the world, especially with your hair done up. It gives me goose bumps to think how pretty you are. Maybe it makes me too proud of you, but how else could I feel keeping company with someone so pretty, don’t you think”? She laughed so prettily and she’d reach over and pat my knee.

This logic and her praise had an effect on me, and slowly relieved my misgivings. She upped the ante, by telling me it would be fun to have a secret we shared and the rest of the world wasn’t in on. “You know you could wear panties right now, and nobody would know but me and you. It would be our secret, I’d like that”.

I was thunderstruck by the idea. I liked keeping a secret from the rest of the people out there, I mean, a world all our own that we made ourselves, Mom and I. It made me think I could get even closer to her. It was very exciting. I dreamed of going through the mall with packages, and Mom laughing and smiling and my hair all done up and makeup with panties on. It was very, very exciting. The first time I had it I liked it, and I had it many times after, it was my most exciting dream yet. Without discussing it, we bought some panties at the mall and I started wearing them most days. What should have been a big step, turned into a small step that only Mom and I knew about. They felt a lot better than the briefs I’d been wearing, silky and smooth. I liked the way they felt and I liked the secret. The only thing I didn’t like about them was I had to go to the bathroom sitting down.

And our routine got more fun with Mom teasing me, “Is this the day my little cutie is going to go to the mall all fixed up? Or am I to be tortured knowing I am with someone who could be so much cuter, if he thought enough about his mother” and “I sure would like to take someone adorable to the mall”, this was always accompanied by hugs and little pecks for kisses. It became a game I loved, me playing coy and turning her down and her looking so sad. We had fun. Then she’d tousle my hair and pinch my cheek and cup her hand under my chin and tell me how I was depriving her of the very great pleasure of showing the rest of the world how pretty I was, but she loved me so much anyway, though she didn’t know why. I’d laugh and say “Mom, I’m sure the world will get along without seeing me in pigtails” and she’d reply that the world needs to see me looking adorable. And we’d laugh and she’d kiss my neck and get lipstick on me. I loved it. Now I understand she was getting me to be confident myself. Then though, I just thought I wanted to make her happy and I loved the attention. I held out for what seemed like a long time during the year I was twelve, before I shyly suggested that maybe I could go out with my hair done, if that’s what she wanted.

She looked delighted but she immediately shot back, “No, no, no, Sweetie, if that’s what you want, we’ll do it. Mommy wouldn’t want her pretty boy to do it just for me, no matter how much prettier it made him, it wouldn’t be right, no matter how happy it would make me”. She grinned triumphantly.

“OK”.

“OK, you want to look cute”?

“Well, I’d like to go out with my hair done up to see what it was like.”

She laughed and told me to finish my class and then come get her. I was finishing up as I asked her so I told her, “I’m ready now”.

“OK, you want to get started right away. Good, let’s go,” and up we went to her room and her makeup table. As she put on her makeup, and brushed a little makeup on me, she kept talking, “You look adorable. You are so cute. We are going to have a great time”.”

When she had finished she looked at me and said, very seriously, “This is so much fun. Another time, maybe we’ll polish your fingernails and toenails, if you want,” she smiled and she sprayed me with perfume and we were off to the mall, with my hair all done up, wearing panties and thinking about nail polish. It was very exciting.

We shopped for a while and Mom bought some stuff for the house and, for me, some mirrored sunglasses. “These will make you more comfortable, because you can hide behind them.” She smiled and put them on me. They had pink frames to go with my ribbons. “I would have thought it was impossible, but you look even more scrumptious,” she said, “so scrumptious you have to be kissed” and she kissed me on the lips got more lipstick on me. She grinned, “I guess it’s a good thing we wore the same color”.

She was right about everything, I felt incognito with the sunglasses on, though I had to lift them up to look at some things she showed me in the stores. The sunglasses did make me feel more comfortable. I caught several looks at myself in windows and mirrors which were here and there, and I did look pretty cute.

While we didn’t really attract much attention at the mall I was a little anxious about getting ice cream, but Mom said not to worry, we’ve got this. When we arrived, there were a lot of people around, but nobody acted strange or made any comments or anything, even though we stood in line right next to them. The ice cream was great. I love ice cream. Mom whispered “Is my cutie having fun being shown off in pretty ribbons and pretty panties?”

I just nodded and thought this was at once silly, and another way very exciting. I convinced myself that situation wasn’t as stressful as I expected, but I still had some trepidation. But I realized then, in the back of my mind at that moment, for the first time I could identify a little spark. I really liked this. Wearing bows in my hair was exciting. Wearing mirrored sunglasses with pink frames was exciting. Wearing panties was exciting. Wearing nail polish would make it even more exciting. I was thinking about this and looking at Mom and smiling and wondering, what in the world was I doing and whether it was OK. I thought it couldn’t be bad though, not with Mom so happy and me feeling so good. It was a lovely summer day. I remember how happy we were, Mom and I, sharing our secret life.

We walked out of the mall window-shopping. Every so often Mom would stop and talk to me about clothes, and shoes and whisper, “You’d look darling in that” and “It is you, totally you, it would bring out your eyes. Those shoes are so sophisticated. They’d look really good on you.”

I wasn’t really paying attention to anything and just agreeing with what Mom said. I was mostly interested in catching glimpses of myself when I could. We saw a display of Capri Pants for Girls in one window and Mom just gushed, “Those are so cute.” I was distracted looking at myself in the window and thinking about nothing except my pigtails and ribbons, and agreeing with virtually everything Mom said. Which is how she managed to slip, “Why don’t we stop on the way out and get a whole cute outfit we can hang up in your closet?” into the conversation and got my agreement before I thought about it. She clapped her hands and laughed, “This is so much fun”.

We went through several stores and bought a crop top, a sleeveless blouse, a pair of the Capri pants and some pink sandals woven loosely so you could see your toes through, but not completely, a couple of more pairs of panties, and a hat with a small brim. “That hat will really show off your pigtails,” she said. I wore the hat out of the mall, chatting with Mom and looking at myself in the windows of the shops.

When we got to the car, “It was such a pleasure to take you out today, you have been so well behaved, just like a proper young lady”, and hugged and kissed me. I felt so special, and, to be honest, I felt that spark even more when she said I was just like a proper young lady. It did get my wheels turning.

When we got home we hung the outfit in my closet. When Mom left my room, I moved it and put it where I could see it from my bed, and think about it. We put the panties in a drawer on top of my other underwear. I noted the panties were starting to outnumber the briefs. That evening I lay on my stomach on the bed and rocked back and forth and thought about how I looked in the windows of the shops. I remember this as my first wet orgasm. I was a little taken aback by it all, at first thinking it was wetting the bed but it felt so good. It felt good to see myself, looking so girlish. I loved looking at myself. I thought about polishing my nails and, for the first time, watched my penis get hard. I rocked on the bed again thinking of nail polish and hair ribbons. It was freedom and it was glorious.

I was becoming quite a good student. I enjoyed Mom as a teacher, and her fixing my hair made the lessons fun. I looked forward to them. I didn’t get a lot of privacy though. My dick was getting hard all the time and it was becoming embarrassing. It got especially hard every time Mom did my hair, which was every day. Mom never seemed to notice though. We just kept running through lessons and one Saturday she said we were running out quicker than we should and she hadn’t ordered ahead so she thought we could just skip the lesson that day. I was a little disappointed, but tried not to show it and said, “OK”.

“Good, come on”, and we went up to her room and her dressing table and she said, “You know what, you look really cute wearing just your panties while you get your hair done”.

I looked at her for a second and decided I was going to get my hair done without a lesson, so I went to my room and took my shorts off and went back in just my panties and t-shirt and sat and looked in the mirror while she fixed my hair while I watched myself. After that we reverted to my regular schedule of lessons five days a week, but fixing my hair became separate from the lessons. She still did my hair every day, on weekdays at the computer, on weekends in her room with me wearing my panties and a shirt. She always made the weekends special by brushing a little lipstick and mascara on me, while I watched her do it in the mirror. On weekends, I’d keep it on all day even swimming and even when we went out to eat or to the mall. I started wearing panties every day, all the time. The way it turned out, I didn’t miss the weekend lessons, after all.

Out of the blue one day she said she had been reading an article, and she thought we ought to start taking vitamins, which we did, both of us, every morning at breakfast. I didn’t really think about it at the time, because I had no idea at the time about anything, but the erections were less frequent. I still loved her doing my hair every day, though. She started encouraging me to learn how to do it, but I’d always demur, “How can I do it taking my lessons? And besides I like you doing it.”

Our life was really sort of ideal. We both enjoyed ourselves, my schoolwork was ever improving and Mom’s attitude was great. Then Dad missed a check. Mom was very angry. She called her lawyers again and it all started again. We still did lessons and she still did my hair, but she wasn’t so playful anymore. I tried my best to help her, but there was only so much I could do. Then one day, another change. I was out swimming and Mom called me in the house, saying she wanted to talk to me. When I first heard this, I dreaded what might be happening, and slowly walked into the living room where Mom was sitting on the sofa. She patted the seat beside her and said, “We need to talk a second. This is very important”. Kids don’t like to hear things like this, especially kids who have been unhappy and have gotten happy. I was dreading the conversation, wondering what change was going to happen.

“Your Dad missed paying us, which is like him. He has no sense of responsibility. I had my lawyers contact him and, when he wouldn’t talk to them, call his parents. Anyway, to make this short, your grandparents proposed giving me a generous payment and setting up a trust for you that will pay for your support, college, and give you a great start after college. They only had one condition, which made me furious at first, but my lawyers said think about any proposal so I said I’d think about it. I’ve decided to talk to you about it, and leave it totally up to you. This will all happen if I will release Paul (that was Dad) from all marital and parental responsibility and change your name to my family name. I’m Ann Marie Quinn and you’re David Paul Rockhampton, Jr. If we take this, we’ll need to change your name to Quinn. What do you think about that”?

I was relieved. If this had happened while I was in school, it would have been a mess, but as it was it seemed pretty trivial to me, I’d like to have the same last name as Mom so, almost immediately, I said, “Sure, why not”?

She looked at me, “Are you sure? Your name now is your father’s name, won’t you miss that”?

“I don’t think so. It’ll take some getting used to, but you and I would have the same name”.

She laughed, “No, you won’t be Ann Marie Quinn Jr., you’ll be David Paul Quinn”.

“That’s what I meant”.

You could see her thinking. “If changing your name doesn’t bother you, though, I’ll agree to it. Are you sure”?

“Sure”, I honestly couldn’t see what the problem was.

Mom kept on thinking then she smiled and said. “We could change your whole name and David Paul would be gone.”

“There’s nothing wrong with that, I don’t guess”.

“Let me think about all that, I thought you’d be upset, but if you’re happy with it, I really don’t see why not.”

“I’m happy with it, Mom.”

All the tension eased just like that, we went back to living our life, lessons, hair braids, and panties with a little makeup more and more days, but every weekend, trips to the mall and thinking about nail polish. After a few weeks Mom told me everything was almost done. The checks had cleared and all we had left to do was my name. “Let’s celebrate”, she said, smiling, “Come on”.

We went upstairs to Mom’s room and she started making herself up. I, as usual, was sitting next to her.

First, she did our nails, my toes and her toes the same color, my fingers and her fingers the same.

She then started doing her eyes while we still had little cotton balls between our toes. She kept smiling and looking at me in the mirror. I, of course, was watching every move she made, excited. She finished putting on her mascara and turned to me with the brush in her hand and said, “Look up”. And she proceeded to put mascara on me, as much as she put on herself, instead of just brushing a bit. “Now, look in the mirror”.

I saw myself looking back with pretty eyes. I blinked, winked, and looked out the side of them at the mirror.

“You like”, Mom asked?

My erection was sticking my panties up like a tent. “Yes”, stumbled out.

“Good”, she smiled and went back to her makeup, looking at me through the mirror and telling me how pretty I looked. I was so excited it was difficult to sit there and watch her. After she put her lipstick on, and blotted it with some tissue, she looked at me, picked up the tube and said, “Pucker up”.

I did and Mom put lipstick on me. Not just a touch, either, but a lot all over my lips. She then gave me the tissue she had just used and folded it so there was a clean place next to where she had blotted her lips. I held it between my lips the way I had seen Mom do a hundred times. When I finished, there were my lips, next to hers. She put the tissue in the corner of her mirror and smiled at me. “There. Perfect, the two of us just alike”.

My head was swimming. We took the cotton balls off our feet and she had me stand up and look at myself in the mirror next to her.

“Oh, what we need now is a picture of the two of us together. Get dressed and come back here. I went to my room and got some shorts and a t-shirt on. She got dressed in shorts and a t-shirt, pretty close to the same as mine. She then got her phone and we posed together and she took several pictures, so, as she said, “I can remember exactly how pretty we looked together. Now let’s get this celebration started”.

In a daze I followed her downstairs to the kitchen. When we got there she smiled and said turned around and looked at me and hugged me again, “Very cute, very cute, indeed,” and she popped a bottle of champagne, “For the celebration”, and she continued. “Come on”. She got a couple of champagne glasses and we went into the living room and sat down. She put the two glasses next to each other with the bottle on the table and the bottle of champagne next to them. “I guess it’s time for us to choose you a new name, huh?”

I was too excited to talk, so I just nodded my head.

“What name should we choose for you? What name do you like?”

I didn’t know.

She looked at me and said, “We ought to choose something that won’t embarrass you. I’ve been thinking about it a lot.”

“What name do you like Mom?”

“I thought Ashley would be nice.”

I cringed a little, “Isn’t Ashley a girl’s name?”

“Nope, both men and women are named Ashley. You can look it up on the Internet. I like it, it’s adorable and it won’t cause any questions to be asked.”

I wasn’t sure what she meant by that, but I agreed anyway, “OK.”

“And, for your second name, Meredith. It can be also either, and it was the name of my favorite aunt. Ashley Meredith Quinn sounds very dignified, don’t you think”?

“Ashley Meredith Quinn. OK, I guess.”

“Of course I wouldn’t call you that unless I were angry with you…Ashley Meredith Quinn, come here!” And she laughed.

I was really uncomfortable I was so excited. I didn’t dare touch myself.

“I thought we could have another secret. For a nickname, I could call you Sissy, because you were my Sissy, you’d like that, wouldn’t you, part of our secret?”

I couldn’t help myself. I came in front of her in my panties. I still remember looking at those yellow silky panties darkening at front and my penis jumping all by itself.

She laughed and pointed and said, “I guess that’s a yes, Sissy, so it’s done!” And she hugged me and kissed me on the lips and our lipstick got mixed together. I got another erection immediately and you could see the tip of my penis in the wet panties. I almost came again.

“Now, let’s drink to it”, and she poured herself a glass and me a little touch of champagne, “To me and my Sissy,” and she put her arm through mine so we could see our fingernail polish and I put my feet close to hers so we could see my toenail polish and she took a drink and I drained the swallow of champagne she’d given me.

“To Ashley Meredith Quinn,” she said and I almost fainted.

“Remember though, all this is just a name Sissy. Who you are is who you are inside”. She looked at me and smiled, “And your name is Sissy”.

That’s when and how I got my new name. We changed it on my school and everything. Mom got a paper from a judge. I was Ashley Meredith Quinn.

“You’ve had a big day, clean up and off to bed”.

“OK”, and I ran upstairs, but I didn’t clean up. I looked at myself in the mirror and kept my panties on and masturbated until I couldn’t anymore. Mom came in that night, and tiptoed to my bed, like she used to when I was a little kid. I pretended I was asleep and she kissed me on the forehead and let me keep the makeup on in bed. I looked like the dickens in the morning and so did the sheets. I took the nail polish off with remover, but a little reluctantly.

Mom redecorated one of the bedrooms, which wasn’t particularly unusual, so I really didn’t pay much attention to it. She got the maintenance company to come in with their decorators and Mom picked fabric and furniture and curtains and paint and pictures for the wall, everything. It didn’t take a lot of our time, none of my time, really, I was just aware of busy people who came and went. After a couple of months, they were finished. Mom had made what she referred to as the “girl’s room”. It had lace bedspreads and pink area rugs and hearts on the pillows and wallpaper. Wallpaper with pink flowers and a huge mirrored dressing table. All the furniture was French provincial, which was a furniture style as Mom explained to me. The dressing table held brushes and spray bottles, just like Mom’s. It had a big mirror. The bathroom was also changed. There was a sink and a full-length mirror and a freestanding tub. There was no longer a shower though. There were pink towels and pink fuzzy rugs on the floor and pink bathrobes hanging on hooks and pink ruffled curtains over the windows. It had a huge walk-in closet with built in shelves and shoe racks, all empty. She put one of the pictures she had taken of us in makeup hugging each other in a frame on the nightstand. I laughed when I saw the room, and she raised her eyebrows. I asked, “It is wonderful, who’s moving in, Katy Perry? She’ll love it”!

She sniffed and said “I think it’s very cute, and tasteful, perfect for the right person in fact”.

It gave me an erection, but it seemed like everything did. For a while I liked to go by and sneak a look in it every now and again.

A new routine established itself, her teasing about finally going to the mall with nail polish on, and me playing coy, until one day I just changed my answer. I was growing up. I’ve never gotten very big, but I was 5’4” by this time and a little surer of myself. The polish we’d put on for the naming ceremony had almost all worn off and I finally answered one of her ‘don’t you want to look cute for Mommy’ questions with “Maybe it would be fun to polish my nails and go out.”

Mom looked very pleased. “I think that’s a good choice, I think everything will be more fun, if that’s what you want.”

After my lessons that day we went up to Mom’s room and she showed me how to file my nails and press my cuticles and buff them and put the nail polish on. She asked, “Do you think it would be fun if we wore the same color polish?”

“Yes, I’d like that.”

Once again Mom painted my nails to match hers like she did for the naming ceremony, my fingers and toes. She talked about how much fun it was putting nail polish on me to go out and how excited and happy she was. She brushed a little lipstick and mascara and blush, though, not like that night. With my braided hair and ribbons, I looked very much like a young girl. She hugged me and sent me to get dressed and I admired myself in the mirror getting dressed, grabbed my sunglasses, which I still had, treasured, and rushed back to her room. I couldn’t keep my eyes off my fingers. My toes were covered up with my tennis shoes, though, which I thought was a shame, they looked so cute.

She sprayed me with her perfume and looked at me thoughtfully. “That outfit we bought you last year is too small now, isn’t it?”

“Yes, I think so.”

“Well, let’s go see for sure.” So we went back to my room. I couldn’t get in the pants, or the blouse. The hat was fine. The shoes were way too small. Mom sadly hung everything back up, then said, brightly, “Well, we’ll just have to get another outfit today” as if that was the plan we had agreed to, and we were off to the mall across town where we were, by this time, regulars, I guess.

As usual, we worked our way through the mall, looking in shops. This time, though, things were different. We tried things on. We actually went together back to the dressing rooms and tried on items. I got pants and blouses, mostly, a couple of scarves, and jackets. I wasn’t really going anywhere, just enjoying the attention when Mom came up with “Oh, this is cute”. I agreed without examining it, I was looking at myself in the mirror. “Let’s try it on. And this one, and this one”, she had an armload of stuff we took back to the fitting room. When we got there I realized she had skirts and dresses. I just looked at her, I mean looked in her eyes as she stood there holding out the first dress. I took it from her. “You’re going to have to take off all your clothes, you know.” I nodded and stripped down to my panties. I couldn’t hide the beginning erection. She looked at me again, “You look so cute wearing panties. Your briefs are, to be frank, ugly.” My erection got bigger. She ignored it and I put the dress on. We had difficulty adjusting it, but she was finally satisfied and I turned and looked at myself in the mirror. A pretty girl in a dress stared back at me, with bare feet and polished toenails and fingernails and makeup and hair in pigtails with ribbons in it. Mom let me stand and look in the mirror for a second before saying, “Turn around.” And, in a daze, I did. I watched the girl pirouette. Mom said, “Put your leg behind you and point your toe and look at how it hangs when you’re walking.” The girl in the mirror looked at first one leg, then the other, and turned back around and smoothed the front.

“It’s pretty”, she said. “It needs to be worn, though. It would be silly to buy it and just hang it in the closet to look at. I tell you what, if you promise to wear it when appropriate, we’ll get it. There is plenty of closet space for all this in the girl’s room.” She looked at me and seemed very sure of herself, and serious.

I hardly hesitated though before saying matter-of-factly, “I’d like to have this dress”.

“Don’t you also think it would be wise, then, to move into the girl’s room, where your clothes will be?”

Again, without much hesitation, “Yes, but I want it to be my room, not the girl’s room.”

She smiled and looked satisfied. “Good, it was decorated just for you anyway, Sissy. We’ll move you in with your new things when we get home. And we can pack up your old room and give those ugly clothes to Goodwill.”

I was looking into her eyes through the mirror and using all my self-control. I didn’t want to cum in my new dress, “OK.”

“After all, you won’t be needing those things anymore, will you?”, Mom continued, “You need more panties and bras and nylons and open-toed sandals and makeup and high heels and dozens of things so you can look adorable for all the world to see, all the time.”

I was almost in a trance, “Yes, I’ll need panties and bras and new shoes”, and I looked at her directly.

She said, a little sadly, “And you need a trip to the beauty shop for a hairstyle more suitable for a young lady instead of a young girl. We are going to have so much fun”, and she smiled and giggled. “You’re so pretty. You know what, let’s just get you initiated on the way out. After we finish shopping for clothes, let’s get your ears pierced at that kiosk by the door. You’ll look so cute in earrings”!

We got purses and shoes and more underwear and, finally, my ears pierced. It was quite a day. I loved it. How I survived again without ejaculating again is beyond me, I looked so cute.

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Sissy Story Chapter 01

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