This is a true story about my crossdressing and how it started.

 

My First Years                   by: Nadia Cook

 

My earliest recollection was when I was only 7 or 8 years old and I was living in Japan. My neighbor was this real cute little brown haired girl who was my age and we went to school together. After playing with her one afternoon outside in our back yard, she asked me if I liked her new dress. It was a soft white dress made of soft satin and had frills at the bottom. I said that I thought she was very pretty in her dress and that her dress looked really nice and was probably comfortable. Well, I guess you can figure out what happened. She and I went in the bushes and traded clothes. It really felt nice and I felt like I should always get to dress that way. Every day that summer we would exchange clothes in our back yard and I got to wear her dresses almost every day. We never told our moms about this and it was our little fun time together. It wasn’t anything sexual at the time, since I was only 8 anyway. It just felt so good to be dressed that way. I really liked the party dresses when she wore them and I had one really favorite one. It was pink and had a bow in the back and was down to my knees. It was real frilly too, and had several petticoats. At the end of the summer, her family moved and I was really upset about it. The day they left, my mom gave me a box and said it was from the girl and her mother and that I would like to wear what was in the box. I took it up to my room and it was the pink dress. I was so happy. The next day I couldn’t help myself and I wore it in my room. My mom came in and looked at me and just said "It looks nice on you" and left. I kept it for many months until I finally grew out of it the next year. I wore it around the house and my sisters kept telling me how nice I was in it. I will always remember that first dress and the girl next door.

Also, when I lived in Japan, I was raised by my mom-a-san, a Japanese lady who cooked for us and cleaned the house and watched after my older sisters and me. By the way, I have two older sisters, one six years older than me and one eight years older than me. When we lived in Japan, I was eight years old and we lived there until I was10 years old. After the incident with the girl next door, I found I really liked looking at girl’s clothes and was curious about the clothes. My mom-a-san and I talked a lot about it and she really helped me with my feelings. She never told my mom and dad about our little talks and how I felt. What she did do was help me to feel better about what I liked. She bought me kimonos to wear at home. She told my parents that it was traditional Japanese clothing and that all traditional males wore them at home. I don’t think she told them that I liked to wear them and that underneath the kimonos I wore girl’s panties and undershirts or camisoles. When I came home from school, she would change me into my kimono and I would get to be her little girl. She only said that when we were alone and she really protected me from my parents and my sisters, so they wouldn’t know or wouldn’t tease me. I really liked the feel of the silk on my skin, both the underwear and the kimono robes. I ended up wearing these clothes almost every day until we finally left Japan when I was 10 years old.

We moved to California and lived in Marin County, which was just across the bay from San Francisco. This was in the early 70’s. I was really sad about leaving my old lifestyle and I only got to bring a few of my "nice" things with me to California. I thought it was really going to be bad and I acted up a lot and was a real pain to my older sister. Her name is Lorraine and she was 18 and I was 10, she ended up being at home with me while my mom was at work. I really got to be a nuisance and she hated having to take care of me and watch me. Whenever she went out my mother insisted that she watch me and take me with her. I would sit behind her and her boyfriend and bother them during the movie or wherever they went. You know how obnoxious little boys can be with their sisters. Lorraine would try to tell me to be quiet and all, but I just kept pestering her and her boyfriend. I knew she had to take me with her, so I just made a game of it and had a lot of fun bothering her and making comments about her boyfriend and her. His name was John and he was a really nice guy, but I still gave him a hard time. He was ready to break up with her because of me when one day my sister decided to make me pay for my behavior. She kept telling my mom about how I acted and that I kept saying things at the movies about her and her boyfriend. My mom finally got tired of hearing about it and she told Lorraine that she could do anything she wanted to me to make me behave. I thought I was just going to be getting a beating, but Lorraine and John had a better idea. On that first Saturday of my 11^th year, my life really changed. Lorraine and John got into his car and told me to get in the back seat, as they had done many times before. When we got to the movie theater, Lorraine got in the back seat with me and said that I was going to be very quiet at this movie. I kind of giggled at her and then she took out her lipstick and put it on my lips. It was deep red and tasted pretty good, but I was shocked. She told me not to take it off or things would get even worse. Then we got out of the car and went inside the theater. Once inside, John turned around to me since I was behind them and told me that he was going to enjoy watching me squirm more and more and that now he and Lorraine would get their revenge on my previous actions. He also said he was going to whip the daylights out of me if I gave my sister any more grief, so I had better start doing everything she said. I was fairly quiet during that movie, but towards the end of the movie I started talking to them and making sounds behind them. I kind of hid behind my sister when the movie was over so no one would see my red lips, which I almost forgot about, but John said I looked so cute with my nice red lipstick after the movie go over. We got in the car and went home. I went to tell my mom what she did to me, but when I got in the kitchen she looked and me and said, "Gee, you look nice today." I said that Lorraine did this to me and she just said that I must have deserved it and she has her permission to do anything to me. I was just stunned and went to my room. I looked in the mirror and it really didn’t look too bad, but I finally washed it all off.

My sister then came into my room and told me that I still did not behave they way I should so she had more "things" for me to wear the next time. I didn’t know what she meant, but I knew I was in for something "new" in my life now. The next day was Sunday and I heard Lorraine asking my mom if she could go on a picnic with John to the park. My mom said it was all right, but she had to take me because my dad and her were going to the city with my other sister for a recital. She really got angry and my mom just said that she had to take me or not go at all. She then asked my mom if she could do something that would make me quiet while I was with her and mom said "sure hon, you can do anything with him that you want that will control him". I knew I was in trouble now. After an hour, my dad, mom, and sister left the house and I was alone with Lorraine. She came in my room and said that she "had" to take me along with her, but I was not going to ruin her time with John, so I would have to be really quiet and act like I wasn’t even there. I said, "sure, I can do that", but I really knew I wasn’t. She then gave me that look of hers and said, "I am sure you will". I wondered what she meant. After a few minutes, she came back in with a dress of hers that she had in her closet and was way too small for her, but I knew who it was for now. She said, "You will now be my quiet sister Nadia, and you will be a very nice and quiet sister and stay out of our way". I really didn’t think she meant it, but she told me to put it on so we could leave. I said no at first and then she told me I had to or else and John would then help me. I did not like that idea, so I went and started to put it on. She then came back in my room and put some panties and a soft silk top on the bed and told me to wear these too. I took my jeans and shirt off and put the underthings on. It felt really nice and I remembered the clothes I wore under my kimono in Japan. Then I put the dress on and it fit too. It felt really nice and flaired out at my knees. My sister came back in the room and gave me a pair of her old shoes and frilly socks and told me I looked really nice for a boy in a dress. She then said that I should dress this way more often; in fact she would make sure that I would. John arrived at the house a few minutes later. My sister called me down and when I got in the living room, John looked at me and said that I would start being a good little girl now. I just couldn’t even say anything and stayed quiet. We all got in the car and went to the park. Lorraine gave me a blanket to sit on and I took it by the trees and laid it out and just sat there and watched them. It felt really nice in the sun and the dress felt nice on my legs, and I did kind of feel like her sister. When my sister left to empty the trash, John came over to me and said I was doing really good and he would tell my sister some things she could do for me. I really didn’t know what he meant. Up until now, wearing these nice things just made me feel good inside and I did not know about things that "turned me on". I remember sometimes having dreams at night and there would be spots on my underwear, but I didn’t know why at that time. Well, I enjoy the afternoon and Lorraine gave me some more lipstick to wear and said I could wear more makeup the next time. I really did not care, but I felt nice that she thought about me and wasn’t mad at me. We got home just before dark and my folks were still gone, so John kissed my sister goodbye and smiled at me after he told her something, then he left. Lorraine told me to go to my bedroom and she would be there in a few minutes. I said fine and went to my room. I sat on my bed and looked in the mirror, here I was an 11-year-old boy and I had this pretty dress on. My lips were bright red and I just didn’t know what I was, but I didn’t take off the dress either. My sister came in and sat next to me and said I was really good and that she was going to like being with me if I would be this way. I said I was confused about how I felt. She said to not worry, that she would help me find myself. She said I was different this way and she liked to help me. She then asked me if wearing these clothes made me feel sexy. I wasn’t sure what she meant then she said that since I was a boy did I get horny and did my penis feel good. I told her I just felt nice all over and I wasn’t sure about the other. She took my hand and slid it under my dress and said for me to feel myself. I still was not sure about this and I stopped my hand on my leg. She then moved her hand on my panties and then moved them under the elastic and gently touched me. I was still soft and she said that it felt so smooth and little, then she pulled it a little and it started getting harder and a little bigger and it really felt great. She looked at me and said that I would feel this good a lot if I kept wearing nice clothes like this. I said I would like to keep doing this if she would be there to help. She kept fondling me and it felt so very good, then all of a sudden I felt this rush and I got very hot and I squirted something right in her hand. It was very nice and I was flushed all over and my face was really red. Lorraine then took her other hand, which had caught the stuff that came out of me and told me to watch her. She took it to her mouth and she licked it out of her hand. She said I tasted good. Then she put a wet finger in my mouth and I tasted it. I said it was a little salty, but ok. She told me that next time I get the "urge" don’t make a mess, but catch it like she did and taste it all. I would like it. She told me she would never waste a boys cum and it was good for her, but she was my sister so I should eat my own and it would be our little secret. I said I would try it maybe. She said she would be there for me next time, but not for every time cause boys sometimes like to do it to themselves. John told her all about it and that I must do as she says or she will let John in to "help" me. I said that we could just keep him out of it and I would do whatever she wants me to. She then got up and said I could get ready for bed now and we would have lots more fun together from now on. I was a little worried by that, but also wondered about what she had planned for me. I went and got my dress off and hung it in my closet and then washed my face and got in bed. Lorraine came back and knocked on my door and came in and told me that from now on I could wear girl’s underwear all the time and when I got older she would get me a bra to wear too. She said she liked having another little sister. I told her I was still confused, but I would be nicer to her cause she had made me feel so good. She laid a nightie on the bed for me and told me to sleep in it to see if I liked it. I had some silk underwear in my drawer and I put those on and the nightie. It felt really nice under the covers now. I told her goodnight and went right to sleep and had a really great dream. That night I slept really good in my soft clothes. My mom woke me up for school and saw me in the nightie, but she didn’t say anything, she just smiled. I got dressed for school and wore panties that helped me remember how I felt over the weekend. School was normal and I just came home and was listening to the radio when Lorraine came in and asked me if I was still feeling all right. I said I was doing ok and told her I was wearing panties and she said she was pleased. The rest of the week was just a regular week and regular chores, but I did find my underwear drawer full of girl’s panties and camisoles instead of the usual underwear. I knew it was my sister that was being nice to me.

On Friday after school, I thought I was going over to a friends house, but Mom came in my room and told me I had to go with my sister to a movie and I must do everything she tells me or I can’t do anything over the weekend. I said ok and figured I would just have to be quiet again. After dinner, my mom and dad left for some function and yelled up to me to behave and they had better not hear I gave Lorraine any trouble. I waited in my room for a while, then Lorraine came in and told me that I had to go with her and she had an old outfit for me to wear, so I needed to wear it and keep quiet all night or John was going to be mad at me. She came back in with a denim skirt, a pretty pink blouse and the shoes I wore the last weekend. She told me to get dressed and I would also wear some lipstick and rouge so the people would think I was her sister with a short haircut. I put the clothes on and the skirt was down to my calves. I felt pretty good and looking in the mirror, I liked the effect of the makeup and clothes. John rang the doorbell and came in and was waiting in the living room when I came downstairs. He said I looked nice for Lorraine’s little sister and he hoped I would leave them alone at the movie. I said I would be quiet and he just smiled at me. Lorraine came down and told me to get in the car. We all got in, I got in the backseat and we stopped after a block and Lorraine said that this was the place so John drove in the driveway to this house. A girl about my age and dressed in jeans and a sweatshirt got in the backseat with me. Lorraine told me that this was Linda and she was watching her while her parents were out for the night. I didn’t know what to say so I just said hi. My sister told her that I was her little sister Nadia. She said hi and sat next to me. We got to the theater and I just followed my sister and John and Linda went and held my hand and we went to the inside of the movie. I was really quiet and did not know what to say. Finally, Linda got really close to me and said she liked me and said she knew I wasn’t a girl, but she liked how I looked for her. I still didn’t know what to do so I just said that I liked her too and she was really cute. She smiled at me and then went back to watching the movie. I do not even remember what movie was on, because I was so excited with her. She then put one hand on my knee and started sliding it under my skirt. Gosh, it felt so nice. She then took out her purse and looked at me and said I needed some of her lipstick so she could kiss me. I was going crazy and just sat there looking at her. Linda then put the lipstick on me and kissed me on the lips really soft. I liked that. She took her hand then and slid it closer to my privates, and then she went under my panties and whispered that she liked my soft panties, and then she put her hand on my penis. I wasn’t hard or anything and she just kind of played with it for a few minutes. It felt very good and I whispered to her that she was the prettiest girl I was ever with. She said I was the first boy she touched down there and she liked the feel of it. I said she was the first girl who touched my down there, I did not tell her about my sister. She then just held my privates, which of course had no hair, and just sat and watched the movie for a while. I was just so happy and content. I really liked her doing that and I smiled at her. After a while she let go and moved her hand to her lap and I tried to watch but it was dark and I think she was rubbing herself cause she kept closing her eyes and then kept glancing over at me. I was just so happy and feeling so good, then John turned around and said "Hey I like you two girls and thank you for being so quiet, then he went back to kissing my sister. Linda smiled at me and said she was so glad to meet me and I was the best boy she ever knew. She said she wished all boys were as nice and sweet and quiet as I was. I just sat there and said "Linda I really like you too" She winked at me, and then held my hand again till the movie was over. We got back in the car and they took Linda back to her house. She kissed me and said she would like to see me again, if I was dressed this way. I said I would next time for her. Then she leaned towards my ear and whispered. "Next time if you wear a bra I will let you touch my breasts, ok? I said yes, I definitely will!!

John and Lorraine then took me home. I went upstairs to my room and lay on the bed and thought about all that had happened. It was so neat and I felt so good about it all and I was really curious about Linda’s breast and what they would feel like. After about an hour, my sister came into my room and laid another nightie on the bed. She said that she talked to mom and to save on clothes, I would get their old clothes now, both the really cute girls clothes and other things. She also told mom that she would do my shopping with me when I did need clothing, especially shoes and other items. She said she would make sure we bought girls shoes for me from now on too. She said Dad would never know the difference in boys or girls shoes and he is too busy to really watch what I am wearing. He is so observant that he wouldn’t even notice if I was wearing a bra. In fact, we will see later on if he notices. I said he would know and make me change immediately. She said we would see later on. Then she sat next to me on the bed and I still had the skirt on and she asked me how I liked Linda. I said she was really cute, but she was wearing jeans and a sweatshirt and I kind of felt too girlish with her. She said that she babysat Linda on Wednesday and that she told her about me and how I liked to dress. Linda was really curious, so that’s why I asked her to go with us tonight. I told Lorraine that she was really sweet and that her hand touched me you know where. Then I told her it felt great. Lorraine asked if I got bigger for her and I said that I didn’t. She then reached under my skirt and started fondling me again. I got a little bigger and she took my hand and put it down there to catch my stuff. It felt so good again and I came with a little more than last time, but not a lot. She told me to lick it off my hand. I did and I liked the taste and swallowed a little of it. She then kissed me on the cheek and told me I needed to do that at least once a week. She could not because she was my sister and that wouldn’t be right, but she could help to teach me things like that. She asked me if I would promise her that I would do this for her and of course to keep tasting it too. I said I would for her, but she couldn’t tell anyone. She said that would be all right cause there would be other things people would find out about me, but if anyone teased me I should come and tell her. I said I would and then she told me to undress and clean my face and get into bed in my nightie. I did as she said and I went to sleep very content and happy. I was beginning to like the things that her and Linda were doing with me.

The next morning was Saturday and my Dad came in to wake me up. He saw what I was wearing and just told me to cover up while he talked to me. I thought I was in big trouble now. He just told me that he couldn’t take me camping this weekend to prepare for next weekend’s scout camp. He hoped I wasn’t too disappointed, but he had to stay and work. He said he felt bad so he would give my sister some money to take me to the store and buy something for camp. I said that would be great and I was looking forward to the next weekend at Scout camp. He still didn’t say anything about what I was wearing to bed, but he just left my room. I went to the door to see if I could hear him talking to mom and I overheard him tell mom about the money he was giving my sister to buy something nice for me. He asked her if I was acting strangely and she said that I was just being punished for bothering my sister the last few months. He said that that was all right and I heard him leave. I went back to bed and slept a little longer. At ten or so, my mother came into the room and said she was going to town with my other sister and Lorraine would be watching me today. I must do as she asks or else. I said I would be fine and not bother anyone, but I wanted to go see some of my friends down the block. She said that was up to Lorraine. She said "By the way, that looks nice on you, I have some more things the girls used to wear in the attic and I will get them out for you since you like them so much. She didn’t give me a chance to answer. Then she left my room and I heard her and my sister leave the house.

After getting up and taking a shower, I was getting dressed in jeans and a t-shirt, when Lorraine came in the room. She told me to get ready and we were going to the store to buy something "nice" for me, since Dad told her she had to go with me. I told her that the money was for some camping gear for next weekend, since we were both going on the Scout campout together. She said that he told "her" to buy something nice, so she would pick out things for me. Dad had given her $50 and I thought we were going to the camping store. She had different ideas though. She told me to wear a pair of my other sister jeans and some sandals and we would go to the shoe store first. Her jeans had a cute design on the back, but still looked like jeans and my sister gave me a light pink t-shirt to wear with it, with a little puppy on it. She then gave me some red lipstick and said to put this on. I said that I thought this was my shopping trip, and she said yes it was and we will buy mostly for me unless I want to get something for her trouble. Then she told me to put my feet on the bed and she started putting red polish on my toes. After she finished she looked at me and I was in a trance looking at my feet, so she started putting the polish on my fingernails. I started to protest, but I knew it wouldn’t do any good. I was told to just sit there for a while and she left to get dressed. She came back after a few minutes and looked really cute in her dress and blouse. I always liked the way she looked in her clothes. She smiled at me when I told her she looked nice, then said that I was a very nice little sister to her. I blushed and looked in the mirror and did think I looked more like a little girl than a boy. She took my hand and we went to a shoe store. There was this really nice girl that worked there, she was my sister’s age and she went and got several pairs of shoes that my sister picked out. She smiled at me when she looked at my feet in the sandals and I had red polish on them, then she noticed my nails and said my hands looked nice too. Then she bought some tennis shoes for me and they were all white so I didn’t mind. My sister bought several socks to go with both shoes and they had frills at the top. Finally the saleslady went to ring up the purchase and she said to my sister, "Your brother is really going to look nice in these things, I wish I could get my little brother to be so nice. Some day at school you’ll have to tell me what you do with him." I think my sister set me up again. We went to the drugstore and Lorraine went and bought some cosmetics, mostly lipstick, polish and rouge. I told her that the money was for me to use. She said that this stuff was for me; unless I was being nice to her then she would use them too. I just said never mind. We then went to JC Penny and she went to the girl’s section and bought several training bras for me to start wearing. I told her that the money was for camping and she said that Mom would tell Dad that that is what I picked out, then he will get mad at me and either not take me camping or maybe make me wear it with the other scouts. Then she just laughed. She then said that we could go home now and I could get dressed since John was coming over for the evening. I did not like the sound of this. When we got home, I had to put all the things we bought in my room and my drawers. There were several boxes in my room too. I opened them and it was all my sisters’ old clothes from the attic. My sister told me to get dressed and then put all the stuff in the boxes in my drawers and closets. You would not believe how many dresses; skirts, blouses and underthings were in those boxes. I was really feeling kind of funny and when I started unpacking the boxes I couldn’t help but enjoy the softness and beauty of all the clothes. I tried a few of the things on too. My sister came in when I had one dress on; it was white with little green flowers on the edge. She said that that dress would be just right for tonight and she would insist I wear it. Then she came in and looked at me and she could tell I was kind of just floating. She told me to sit down and start touching my breasts with one hand and hold my little penis with the other. I did and it felt so nice. She told me to keep rubbing both of them very gently. I did and it did not take very long and I felt myself growing. She raised my dress and looked at my little penis and told me that some day another girl would hold it for me and kiss me all over. It felt so wonderful. I could feel it coming, so I took my other hand and waited for my stuff to cum. It did and this time there was even more of it than the last time. It filled my hand and my sister went and licked a little of it, then told me to "eat" the rest of it. I did and I really liked it and my sister said I was getting older and better for some nice young girl to hug and kiss and touch me all over. I couldn’t wait for that day to finally come. I told her thank you and she said I was worth it since I was not so much of a nuisance to her. She liked having my girl side with her. She then told me to get my lipstick and some rouge on since John would be over soon. I still had my nails bright red and I liked the look of them around my waist when I looked in the mirror. Every time I picked up something I could not help but notice my nails. I knew then that I was hooked on this pleasure and did not know what might happen next.

 

 

I will continue with other stories during this time in my life. I had some unusual experiences, some very good, some very weird, throughout my years, but I like tell about true experiences. I just have to get better at telling these experiences so that they make the reader feel good about them. I hope you enjoyed my first try at this. More to come, I hope.        Nadia Cook

© 2000
The above work is copyrighted material. Anyone wishing to copy, archive, or re-post this story must contact the author for permission.