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.
This story was taken from one these sites, check them out to find more sex stories:
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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.
This story was taken from one these sites, check them out to find more sex stories:
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