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This is a continuation of a true story about my early years of crossdressing.

 

My Early Years              by: Nadia Cook

 

I remember my sister had told me I had better behave and that she liked me more when I was her quiet sister Nadia. I really did not know what I was getting myself into, but I still did not trust my sister’s ideas, nor did I know what to do with my own feelings. It was a lot better for me if I just went along and did not cause any more trouble.

The clothes my sister put out for me were very nice and so soft too. The dress she had me wear was white with green flowers on the trim. The dress was one of those that spread out and needed a petticoat underneath it. I had on the new panties my sister had bought with my money, and the new girl’s shoes she had bought and I still had my fingernails polished a nice bright red. And, of course, the new training bra my sister bought for me. I still had the red lipstick and rouge on too. When I looked in the mirror, I looked like a girl of 11 with really very short hair. The clothes did not really turn me on, but they felt really nice. I know now that I was "hooked", but then I just felt like I should just be doing what Lorraine (my sister) told me to do. I knew she had Mom’s support and Dad just didn’t care I guessed.

I stayed in my room until I heard the doorbell ring. I went down the stairs and John had arrived. He saw me and said I looked real nice for a girl and he hoped I would stay out of his and Lorraine’s way tonight. I went and sat on the couch and started watching TV while my sister was getting ready upstairs. He sat in the chair across from me and watched TV, but kept eyeing me to see if I would do anything. My sister came down and sat next to him and John asked her if I was going to be right there all night. She said she had to watch me, but that that same girl last week was being brought over by her parents to be here too. My heart kind of skipped a beat. We all waited a few minutes, while John kept staring at my dress. He said he remembered when Lorraine used to wear that dress and she was a knockout. I might be just like her in a few years. I just grinned and kept watching TV. I really didn’t know if I liked the thought of wearing her dresses for "several years". I thought this was only a temporary thing. I felt kind of trapped, but also I was enjoying the "feel" of the clothes.

The doorbell rang and Linda and her mom came in. Linda looked at me and smiled and said hi. Her mom looked at me a little peculiar, but just said hi. My sister said, "This is John, my boyfriend and my little sister, Nadia." I just smiled at her and she said "Hi there, nice to meet you, I wish Linda would have dressed a little nicer" Linda was wearing a pair of short shorts, open toed sandals, and a white blouse which I could see her pink bra through. I thought she looked like a knockout. Her Mom said she would be back in a few hours to pick her up. I felt like this was going to be a pretty good night after all.

Linda came over to me and gave me a little hug and we sat on the couch. She said she wanted to see some show on TV, so I changed the channel and sat back down. John looked over at my sister and smiled and then they left the room and went to the family room in the back of the house. After about 30 minutes of watching TV, Linda moved over to me and put her hand on my leg and smiled. I just sat there not knowing what to do. I think I was afraid to touch her, so I just sat there like a dummy. Linda moved her hand up my leg very slowly and moved closer to me. She leaned over and looked at me and I looked at her and we kissed, not those long kisses, just a soft kiss. She said she liked my lipstick. She wasn’t wearing any. We both just watched some more TV and all for a little longer. Her hand slowly creeped up my leg and after a few more minutes, she went under my panties and held my little penis. I did not get bigger at all and she just kind of held it for a long while. It felt nice…. Then after a while she whispered that she liked touching me and it felt soft. She said my dress made me very sexy and she really liked my clothes on me. Then she asked if I was wearing a bra, which I was. I said yes and she smiled at me and said "You can touch my breasts if you want to. I was a little nervous, but I went under her blouse and reached for her small breast. If felt really neat and was so soft in my hand. While I was holding her, she gently rubbed my penis and and said "wouldn’t you like to have breasts like mine?". It felt so very good, and I said yes, Linda, yes I would" She kept rubbing me and I just held her breast and she said I needed to do this more often and be her girl. I said yes that I would like that. Then, I felt myself cumming and I told Linda that it was going to squirt something. She said that that would be ok as long as I was still thinking about being her girlfriend. I said yes, yes and I squirted into her other hand. Gosh, it felt wonderful, but now I realize that I was associating dresses and girls with what she was doing. She then took my "stuff" and licked it a little, then she looked at me looking at her and she smiled and said. "Here this is yours, why don’t you taste it?" I smiled at her and then licked all of it out of her hand. She looked surprised and then said "I didn’t think you would lick it all up" She then smiled and said this was fun and she was enjoying me. We both sat back and watched more TV for a few minutes.

I was admiring her legs and shorts as I watched the TV, then she caught me watching her and she smiled at me and said. "Ok, Nadia, I have an idea. Do you have any of that red polish left?" I said yes, its upstairs. She asked me to go get it so she could polish her toenails since they looked so plain and we still had time before her mom came to pick her up. I went upstairs, swishing all the way and just feeling great. I got the polish and Linda started polishing her toenails, then she looked at me and told me to take off my shoes and socks and I could be just like her. So, I just smiled and said ok, then I took off my shoes and socks and she took my foot in her hand and started putting the polish on my toes. I just sat there and watched her. She just made me feel like I should have done this before. She finished my feet and told me to just sit there with my feet on the couch over her lap and she had her feet on the table. It looked quite different with the red polish on. I kind of liked it.

After a half hour of so, my sister came out of the back room and saw us sitting there. She noticed both of our feet and said. "Gee, Linda, I should have thought of that for him" You both look so cute, too bad I don’t have a camera". Then she left the room and we just smiled at each other and watched some more TV. The doorbell rang and I started to get up, but my sister came in the room and said to just stay there and she would get it. It was Linda’s mom and she came in and saw us sitting there, and she said. "How cute, looks like you two are hitting it off. We need to go, Linda" I just got really red all over and moved so Linda could get up. I was still barefoot and my feet looked really nice with the dress. I said bye to Linda and she said she would see me sometime later. "And thanks for the polish, Nadia". I was disappointed to see her leave. My sister looked at me and said I looked better and that this may be a nice beginning for me.

She said she liked Linda, too. Then she told me to go to bed and be sure and wash my face real good and put a nightie on too. I just went up and did what she said and went to bed. I felt so great that night. I hoped I would see Linda a lot more often. The next morning my sister woke me up to get ready for school. She gave me some polish remover and showed my how to get the polish off my fingernails. She said that some guys at school would really give me a hard time if I wore polish to school. She put out some of her old jeans and a corduroy shirt and told to me to get dressed. She said to wear my nice panties and the bra and no one would even know. I told her I couldn’t cause I would get caught, but she said go ahead and she bet that no one but her and I would know. If anyone found out than I could stop wearing the dresses on her dates from now on. I said all right but I just knew someone would notice and I would be teased for it. I wore the light blue panties that felt really soft and a white training bra, which was of course pretty but flat against my chest. I was really worried all day long that everyone was looking at me and knew what I was wearing, but I made it through that first day and nothing happened at all. I was really surprised, but kind of relieved too, when I got home from school. My sister gave me and my other sister a ride home from school.

We got home and my parents were still at work. I was going to go outside and play when Lorraine grabbed me by my shirt and told me to change into the clothes she wanted me to wear at home. I was a little upset cause I was going to go play some football. I told Lorraine I was going to play football with Jim next door. She said I could go out, but I would have to wear lipstick so I would look nice. I said no way cause Jim would laugh at me. She said that was her rule until mom gets home, since she has to watch me everyday. I told her that I just couldn’t do that, so if I had a choice I would just stay inside. She said that would be fine, but the rule is that I wear the clothes she has picked out for me while she is in charge. I finally said all right and went up and put the dress on that she had laid out for me. Since I was wearing the dress, Lorraine told me to wear the lipstick and rouge and since my toenails were still polished (I had already forgotten I had them polished too) I could wear the sandals she bought for me. I went and put on the slip and dress and the sandals and went down and watched TV. Lorraine came up to me and then put lipstick on me. I watched TV until I heard my mom come in. She was talking to my sister in the kitchen and then came in and saw me sitting there. Mom told me that I was nice and quiet and my sister gave me her a good report on me. I could go on out and play now that she was home, but I had better change so I wouldn’t mess up the clothes I had on. I ran upstairs and literally threw the dress off and put on my jeans and sweatshirt. I almost forgot to take off the lipstick, but I remembered and washed my face. Then I went out and played with my friends until dinnertime. When I came back in for dinner, we were at the table eating and my Dad asked me how things were going and if I was behaving now for my sister. I told him that things were just fine and I was obeying my sister’s every command. He said that was great. Then he asked me if I got the camping stuff with the money he gave Lorraine. Then Lorraine said that I bought some much-needed clothes for school. He said that I needed to get a sleeping bag. I had forgot about that. Now he won’t have one. My other sister, Rose, told my Dad that I could use hers that she used for overnights, since it wouldn’t be that cold this weekend. My Dad said that would be great and he gone back to eating. I then remembered that her bag was light blue with little dolls on it. I started to say something but I would just show him later and he would get me a new one.

The rest of the week was the same every day. I wore my panties and bra every day under my jeans and shirts and of course kept my toenails polished. I started getting used to the underclothes and most of the time forgot about having them on. I was enjoying the nice feeling of the girl’s underclothes. I never had any incidents I can remember for that first week, but on Friday things got a little rough. When I came home from school, my Dad was there packing the car for the boy scout field trip. He told me to get my uniform and my gear and get it in the car. I went and got all of my things and my sister brought me her sleeping bag. It was definitely very girlish looking. My Dad saw it and then started yelling at me for not showing it to me earlier. He would not have enough time now to get me a new one, so I would have to sleep in this one. And if the other boys made fun of me than that was too bad and I would just have to be embarrassed. He told me not to bring any other of my "girls" things cause this was "boy scouts". I was a little shocked by his statement. Lorraine came out and brought my backpack. She said I forgot my toothbrush and she put it in the backpack for me. We left and drove for an hour or so until we got to the campground. We unloaded the car and met all the other scouts and we all started putting up the tents and putting our camp gear away. When the other scouts saw my sleeping bag they all laughed at me and made remarks about my sister’s bag. My Dad just told them to be quiet cause that is all I had to bring. Luckily the rest of the weekend went fairly normal. When I had to change clothes the next day, I noticed my sister had put panties in my backpack. I usually changed inside the sleeping bag so no one ever saw them. I got lucky, but I knew she did that on purpose. We had fun camping, but that was the last time my Dad did scouting with me. He said he was getting too old and couldn’t keep up with the kids. After that, I attended a few more meetings, but I lost interest too.

We drove back to the house on Saturday and I went back to my normal routine for the next week. Late that night, I could hear my parents and my sister arguing downstairs and I think it was about me. When I finally got downstairs to eat breakfast, Lorraine was there and she said that she was going to play tennis with her girlfriend this morning and I had to go along. She was really upset that she had to watch me. Then she told me to follow her to her room. She said she had this old tennis dress she hadn’t worn in years and that since I had to go with her that I had to wear it. I said I didn’t know since this was out in a public spot and people could see me. She said, "You don’t have a choice!" So she told me to put it on and my new socks and tennis shoes and we would go. I felt kind of funny, but the dress was pink and had like shorts and and a small skirt and I knew I would be in bigger trouble if I didn’t do what she said. We got to the courts and her girlfriend was waiting for us. She told my sister that her brother looked so cute in the outfit and smiled really big. She told me she would like to baby-sit for me sometime and we could have a little more fun (boy, did I fantasize about that later). They played tennis a while and I hit the ball against the big board for a while, then her girlfriend showed my how to hit the ball and serve. This is when I got my first interest in playing tennis. Later on in high school I would end up playing on the tennis team and eventually I won the regionals here in Texas. Of course, I didn’t get to wear a tennis dress except on private occasions in high school with another girl friend, but that is another story.

After playing tennis, my sister took me home and her girlfriend came over with her. I went and took a shower and changed to my jeans, then Lorraine came in and told me that as long as we were alone I have to wear one of my new dresses and since I did not have them on I needed to put lipstick on and my sandals, so her friend could see how I looked all nice. I really was nervous and just decided I guess I had better do what she says. I changed into a nice yellow dress, I also had on my panties and bra and a petticoat to go with it. I went downstairs to watch TV and sat on the couch. Her friend came in and laughed at me and said she wouldn’t believe it if she hadn’t seen it with her own eyes. She sat next to me and my sister gave her a tube of red lipstick and she put it on my lips. It felt good. Then she asked my sister if she could see if I was really a boy. Lorraine said sure. She then squeezed my breast and said, "Well, he has nothing there". Then she took her hand and went under my dress and slowly went to my panties and pulled them down a little. She felt my penis; it was not big or anything. My usual size was about an inch or so. She touched it and then held it for what seemed like a long time. She looked at me and said, "I guess you are still so young, that you don’t get hard?" My sister then told her that I have gotten hard only had a couple of times and I got only a little bigger. She then kind of rubbed it very gently for a few minutes, but I still did not get big, but it felt so great. Still to this day I like to be fondled without getting hard. She did this and then smiled at me and said, "I think you really like this girl thing and I will bet someday you will really get turned on by some sweet girl".

Then she asked my sister if she could see my privates instead of just feeling them. I wanted to say no, but I just smiled at her. My sister nodded her approval and she told me to stand up and raise my dress and hold it above my waist. I did this and she pulled my panties down and looked at my little hairless penis. She then got down and I couldn’t see what she was doing, but it felt wonderful and wet. I was still small when she stopped and then she just said "Thank you, Nadia, that was so nice. I like it when a boy doesn’t get hard so quickly. You are the first I have ever seen stay small, thanks again." I just stood there not knowing what to do, but I did know it was a very good feeling. I just felt so comfortable. She then said she had to go get ready for a date and she left after giving me a kiss on the cheek. I am sure she went out that night and really had fun with her boyfriend. I pulled my panties back up and sat back down on the couch.

My sister then said that Linda was going to come over again tonight so she could baby-sit her. My heart was now just pounding. I couldn’t wait…

Linda and her mother arrived about a half hour later. Her mother came up to me and invited me over after school next week to play with Linda. I said that was great. Linda smiled and said to her mom. "Isn’t he sweet, mom" Her mom just smiled at me and said to behave myself tonight and when I come over later. I told her I would be just perfect and make them both happy. She said, "We’ll see" Linda’s mom left and Linda sat on the couch with me. She had on jeans and a sweatshirt again. I told her she would look good in dresses and she told me to just be quiet cause she liked it this way. She sat next to me and we both just watched TV. My sister cooked some popcorn and then sat in the other chair and watched the TV. Linda started to move her hand under my dress and petticoat, I got a little nervous with my sister there, but she looked over and just smiled at Linda. Linda then moved her hand up and just held my penis again and kissed me on the cheek. I started having fantasies about her and me together, but I was just so comfortable with her I just sat there and let her play with me. Once I went and moved my hand and touched her breast, she didn’t have a bra on. It felt so tiny and nice. I really liked her size and she whispered to me "Wouldn’t you like breasts like mine?" Of course, I just smiled at her and nodded. Almost every time we were together at my house or her house or a movie with my sister, this is what usually happened. Nothing much else, but it was the most relaxing times I have ever had in my childhood. She made me feel just great.

After the show was over, my sister told Linda I wore a tennis dress today at the courts. Linda couldn’t believe I had the nerve to do that. She told me to bring it over to her house next time so we could play tennis together. I just smiled at her and said, whatever you say, Linda. Her mom came in later that evening and picked her up and said she would see me next week after school. I told her that I would be there.

School was the same the next week. I wore my regular clothes except for the bra and panties, which started to seem just natural to me. On Friday, my sister picked me up and Linda was in the car too. I was glad to see her. She had on some pedal pushers and a blouse and had a little makeup on and looked really nice. Lorraine said that she was taking us both to Linda’s house and I was spending the night there. She wouldn’t have to baby-sit me for once and she would actually have a date for Friday night without me. She was really happy. She said that I better obey Linda’s mom or I would really get it for the rest of the weekend. I said I would be real good and nice and sweet. Linda said that she would make sure that I would too. They both just smiled at me. Humm, I wondered what she had in mind.

When we got to the house, Linda’s mom let us in and told us both to go to Linda’s room and play since it was raining. We both just ran up the stairs. I never met her father and I asked her about him and she said he didn’t live there anymore and only girls lived in the house now. I went into her room and it was just the way I thought it would be. It was a typical girl’s room with pretty things all over and a nice big double bed with canopy. She only had posters of girl’s on her walls though. I thought she would have some boy’s bands or something like that, but she didn’t. She showed me her closet and it was huge with all kinds of clothes, but not as many dresses as I had in my closet. We sat on her bed and she showed me some pictures of her friends at her school and I noticed she didn’t have any with her and any boys at all. I didn’t say anything at the time. She then looked at me and said I needed to have a little color in my face like hers. She took some lipstick out of her dresser and put some on me and then gave me a nice soft kiss and said, "That’s a lot better".

We looked at some more pictures and then she asked if I wanted to see her "special" album. I said sure. She got it out and it had pictures of her and another girl in different clothes. The other girl was always in dresses and she was in jeans or slacks or shorts. And in some of the pictures they were making out and touching each other, of course with their clothes on. She asked me if I liked them and I said they were nice. She asked me if I would pose for some pictures with her later. I said sure that would be all right with me. She said great. She asked if I noticed that the other person in the picture was a girl she was kissing. I said yes. Did I understand what that meant? I said I just thought you were friends. She said yes that was all it was and I was her "friend" too. I was thrilled to have her say that.

Linda’s mom called me down to the family room and said she would like to talk to me. I went downstairs, still dressed in my school clothes and with the lipstick on my lips that Linda put on earlier. I came into the room and Linda’s mom told me to stand next to her. Linda’s mom is gorgeous, she has long brown hair, and blue eyes and wears really sexy short dresses. She is only about 30, but she looks 20. She had on a white mini-skirt and a blue blouse and dangling earrings with just the right makeup and short heels. Really nice… I stood by her and she just looked me over for a minute or two, then she said. "I would like to tell you a few things about this house and our rules here. If you agree and obey my rules then we will all get along and you can see Linda as much as she wants. Otherwise, you will not be allowed to play here or to see Linda." Let me ask you a few questions first. I know you are a boy and Linda likes you a lot. However, men and boys are not welcome in this house ever since Linda’s father left us, but since you seem to like to be a girl, then I agreed with Linda that she could see you and invite you over her. Now, is this how you dress for school?"

I told her yes, and then she said, "Do any of the other kids say anything to you about the bra you are wearing?" I looked at her and then realized that she had noticed it and then I started wondering if other kids had noticed it in school. I told her that no one has said anything to me since I started wearing bras and panties to school. She then said, "oh, and you wear panties all the time too?" I said yes, now that my sister has insisted on me dressing this way. She then said, "Well, then it is your sister’s idea and not yours and you are only doing this as some kind of punishment?" I told her that Lorraine suggested that I dress this way, but now I kind of like it and do not mind wearing girls’ clothes now, but I am still pretty scared about doing this in public. She then said "I think I can see what you are doing and I like it when you dress as a girl. And……from now on…. When you come over to our house, we want you to dress only as a girl…. Is that ok with you, Nadia??" I said I did not know if I could do that or not, since this is so new to me. She then said, "Well, I tell you what, if you can make it through this weekend as Linda’s girlfriend, then I will have a nice surprise for you and you will be able to come and visit as often as you would like. Would you like that???"

I told her that I am not real sure about what is happening, but I really enjoy being here and anywhere with Linda and I would try very hard to please her if I could keep visiting and seeing Linda. I would try very hard to please her and Linda. She said, " I would have to agree to do whatever she and Linda wanted, but most likely anything they ask of me would not be anything any other girlfriend of Linda’s has done." That seemed reasonable to me, so I told her I would try.

Linda’s mom then asked me if the girls’ clothes I was wearing turned me on. I told her that I was getting used to them, but that I wasn’t sure what she meant. She asked me if I got hard down there. I told her that I have had that happen a few times, but that it wasn’t just the clothes. She said that she would not tolerate any "male things" and she would protect Linda from any man ever hurting her. I definitely felt she did not like men. She said that I would have to be punished if I acted wrong anytime with Linda. I wasn’t sure what she meant, but I knew she really did not like men around them. She then told me to go upstairs and Linda would send me down in a few minutes so she could talk about a couple of other things and see how I reacted. I told her I would really try to please her and Linda since I liked them a lot. She smiled at me and said that she thought things might just work out for all of us.

I went back to Linda’s room and told Linda what happened. I asked her if she told her mom everything we had done together. She said her and her mom talk about everything and she knew all about me, including what she likes to do to me. Now, I knew this would be a different experience for me. I was a little bit worried and scared, but I still felt I trusted Linda. Linda then told me to take a shower and clean up and she would lay some clothes on the bed for me. She went to her room and started cleaning up too, since she just came from her school.

The shower felt really nice and after I dried off and brushed my teeth, I went to my room and on the bed were the clean clothes for me. There was a pair of frilly pink panties and a pink bra, some pink socks and black shoes with a medium size heel. Next to the pillow were a very pretty white petticoat with several layers and a beautiful pink party dress. I wasn’t sure about putting these on and I just put the panties and bra on when Linda came in. She had exactly the same outfit except hers was all baby blue. She asked me if I needed any help and I just said "Do you want me to put this on for sure??" She said yes and started to help me get the petticoats on. I really liked the way it flared out and then when she helped with the dress I was just thinking how pretty Linda was in her dress and that I still would look like a boy next to her. I told her I still looked like a boy in this dress. She told me that that is exactly what she wanted and later I would maybe look more like a girl if I wanted to.

After I put on the shoes and socks, Linda had me turn around for her and kind of model the dress, which really fluffed out and she was really happy and smiling. Then she went and had me stand there while she put some deep red lipstick and a little rouge on my cheeks. She said I made a great looking boy-girlfriend for her and she said, "Thank you very much", then she kissed me on the cheek. We then went downstairs.

Linda’s mom called us to come into the family room. She asked Linda and I to stand in front of her. She was grinning and just so happy to see us both in similar dresses and said that we were both very pretty together. Then she asked me to turn around and she held me by the waist and fluffed my dress out. Then she asked me how I felt. I told her I was feeling very girlish and liked the feel of the clothes. Then she really surprised me and raised my skirt up and her hand went around my waist and under my panties and she grabbed my penis and balls. Her hand felt really nice holding me. I just stood there in amazement, wondering what she was doing. I was still small and she let out a noise like a squeal. She said, "I am really happy and surprised that you are nice and normal and not at all hard. You feel so nice and soft like a young lady, you will make a great friend for Linda and I am very pleased you are this way." Then she squeezed me hard and let go of me and put my dress and petticoats back down. She told us to go and have fun reading or watching TV in the next room. So we left and went and sat down on the couch and Linda turned on one of her favorite shows.

Linda told me she was really happy, but she still preferred to dress her normal way, but this was also nice since both of us were dressed the same way. I remember it being quiet for quite a while, except the TV going. I don’t remember what we were watching. After a while, Linda sat even closer and then started kissing my neck. We both kissed each other for a little while, and then her mom came in and took several pictures of us kissing. Linda then put her hand inside my dress and was touching my breast and her mom took a picture of that too. A few weeks later, the pictures of us were in her room with the other pictures of Linda and her other girlfriends. That made me really happy when I saw them later on. Then Linda liked to whisper in my ear and ask me if I wished I had breasts. I always told her yes that I would like to have breasts like hers, and then I would touch her breasts too. We spent many nights like this just kissing and touching each other’s breasts. Near the end of the night, Linda finally went under my dress when her mom wasn’t there, and she fondled my penis. I didn’t get turned on, but it made me feel really great and ever since then I have always loved to have my flaccid penis touched this way. I think that this has always been more pleasurable than when I am hard, it’s just that after I reached my teens I became more aroused earlier than when I was younger. It is hard to explain, but I feel that this earlier experience reinforced my sexual desires to dress up later in life.

Finally, it was getting late and Linda’s mom came in and told us that she called my mom and it was all right for me to stay with them for the entire weekend. I told her I didn’t bring any clothes, but she reminded me that they had plenty of clothes I could wear and I would enjoy this first weekend with Linda and her. I was very satisfied and told her I would be pleased to be with them. Linda and I went up to our rooms and took our dresses off and washed up. When I came out of the bathroom, there was a very pretty yellow nightie and panties for me to wear on my bed. I didn’t hesitate and just put them on and got into bed. It felt just wonderful with these very soft and frilly sleep clothes touching my skin. I immediately fell asleep, wondering how this weekend was going to end…..

The next morning Linda came in my room and woke me up. She said I sure looked cute in her nightie. I felt really good and the nightgown felt nice against my skin. I felt strange having Linda sitting next to me in the bed, but then I looked at the door and her mom was they’re looking at both of us. Linda’s mom told us to get up and take a shower and then come down and have breakfast. Linda said she would put out a nice outfit for the morning and we could look like sisters again. I had no idea what she had planned, but it kept my mind wondering what I would be wearing. I took my shower and went into the bedroom and on the bed was a pair of pretty white panties with lots of frills and a white bra and white blouse and then a pair of blue capris pants. I went ahead and put on the panties first and the bra, then the blouse, which was really light and see through and the bra was very plain to the eye. The pants were a nice fit, but they came only down to the middle of my calves. I looked for some shoes and socks, but there were only some open toed sandals with small heels on the floor, Linda came in and told me to wear them and she would help me put them on. Of course my red toenails showed very nicely in them and I really looked like a sissy boy in them. Linda had the same things on and she really looked nice in them. I kind of felt uncomfortable, but she kept telling me that I looked good and she was proud of me. When we came down for breakfast, her mom said we both looked very pert in our morning outfits. I told her thank you and went ahead and ate breakfast with them. They talked a little about another girlfriend of Linda’s and told me I reminded them of her because when she came over they always dressed alike too. We went into the living room and Linda’s mom took some more pictures of us. She also asked us to sit down so our pretty toenails could be seen in the picture. One of the pictures she took, Linda started kissing me really long and I really felt wonderful, but I still didn’t get "turned on" that time. Linda just kept telling me I was being so good for her and her mom and putting up with them. I told her I just liked their company and was very glad they liked me this way.

After about an hour, Linda said "Lorraine told me that you went playing tennis with her and her girlfriend and that you were really cute. Would you like to play with me this morning?" I told her I didn’t have anything to wear unless I could borrow her shorts and a tee shirt. Linda said that she just happened to have bought a nice tennis dress and I could wear it if I wanted to. I told her I was a little nervous wearing one with Lorraine, but my sister had insisted so I had to. Linda just stared at me with her pretty blue eyes and said "Would you please wear my new tennis dress for me?" I told her if it would make her happy than I would. She left the room and talked with her mom and then came back and led me up to her room. She told me to take my clothes off and she handed me this very pretty blue tennis dress. I really liked it, but I wanted to see her in it. She told me to take this and change in my room and she would be in to see how I looked. She also gave me some socks and a pair of white tennis shoes to wear. I went to my room and took off the blouse and pants and left the panties on and then put the tennis dress on. It fit just right and the small pleats went only halfway down my thighs. I just knew I would get looks from this and I hoped there wouldn’t be a lot of people around. Linda came in the room in just her panties and looked at me and said I looked wonderful. Then she took some red lipstick and put some on my lips. She said she would keep the lipstick in her bag for later. Then she went to her room to change.

Well, when she came back in the room I was kind of surprised. She had on a pair of tennis shorts and a t-shirt. I asked her why she wasn’t wearing this dress and I could wear the shorts. She told me that she hadn’t worn the dress yet and felt more comfortable in the shorts, and besides, she liked me as her sissy tennis partner. I was a little upset, but she had been so nice to me I just agreed with her and we went down to see her mom. When her mom saw us she really smiled and went and got the camera again. She told me I was really going all out for Linda and was a great girlfriend for her. I would really get that surprise she promised since I was so willing to make her daughter feel happy. I just smiled and told her I was happy too with Linda. Linda’s mom then drove us to their club, and I was kind of hoping we would be in a quiet court somewhere.

I was really nervous getting out of the car and there were a lot of people at the club, some were going golfing and others to the courts. I followed Linda and her mom and we luckily didn’t go into the club, but went right to the courts. However, when we got there, there were two other girlfriends of Linda’s waiting at the courts. I guess I was Linda’s partner. We met them; I think there names were Susan and Terry and I had seen both of them in the pictures with Linda. They saw me and told Linda that she finally was going out with a guy, but he was still in a dress. They kind of smiled at me funny, but Linda told me they were her friends and they knew what she liked and I was just fine for all of them. At least they didn’t laugh, except when I missed quite a few shots. I still hadn’t got the hang of the game yet, but as time went on I practiced more and more and got a lot better later in the year. The girls were really nice and polite and showed me the right court etiquette and all. I learned a lot from them, and they really got a kick out of Linda after every set putting more lipstick on me. They said several times I looked "cute" in the outfit, and that they never saw Linda in a tennis dress and maybe I would rub off on her. I really enjoyed learning the game and forgot I was wearing a dress. It just kind of felt like a normal outfit to play in. I wished many times later in life that I could have played in a tennis dress. I did feel like I fit in with the girls even though only one of the other girls was wearing a tennis dress too.

We didn’t win, but the girls said they would like to play us again after my stroke improved. I told them I would practice more. They said that they were sure Linda would teach me a lot more too besides "tennis". Linda’s mom then came over and took us into the clubhouse for a drink. Now, I was really embarrassed and I got a lot of stares from everyone there. I was probably pretty red in the cheeks from embarrassment. Linda’s mom told me not to get worried and forget what other people are doing. That is easier said than done though. I was glad when we left and went back to Linda’s house. We went and cleaned up and when I finished there was a skirt and blouse on the bed for me with nice clean panties and a bra. The skirt was like the plaid skirt that Linda wears to school and the blouse was lavender and very feminine and frilly. I went ahead and put the clothes on and the open toed sandals that were there. Linda came in a few minutes later and she had on jeans and a t-shirt. I didn’t say anything cause I was beginning to understand her. We went out on the patio and her mother was there and she took a couple more pictures of us. Again, she liked to take a picture of us kissing each other. I didn’t mind cause Linda was such a good kisser.

Linda’s mom asked us if after dinner we would like to go play miniature golf and Linda said that that would be fun and I agreed. After dinner, Linda took me up to her room and got out some pink shorts and a pink sweatshirt for me to wear and then she put on some white shorts and a red sweatshirt for her. Of course, I still wore my panties and bra underneath them and I wore the sandals so my red toenails could be seen. We then drove to the putt-putt course. Her mom took several pictures of us playing golf and she took one picture when Linda was putting lipstick on me. I was very conscious of the red toenail polish every time I putted and the red polish I had on my nails too. I felt like several guys were looking at me and talking about me, but no one bothered us while we were playing. I had a lot of fun though and felt great with Linda as my friend. We went home after that and Linda had me change back into the school dress I was wearing earlier and we sat on the couch and took our polish off and put new polish on our hands and feet. I really liked doing Linda’s nails too. Her mom took a picture of Linda putting nail polish on my nails too. It was getting late so we were told to go to bed and I had to go to church with Linda tomorrow. Linda got a different long silky nightgown for me and told me to sleep tight cause tomorrow would be really different for me. The nightgown felt really nice and I went to sleep dreaming about Linda that night.

The next morning I woke up and went down for breakfast. They had laid out a nice girls robe for me and a pair of slippers. I ate and then Linda told me she would get my clothes for church. I wondered what she and her mom had in mind for me now. When I finished my shower, I looked on the bed and there were some more very frilly panties and a bra and another petticoat and a very pretty orange dress with lots of ruffles and a white border and there were some fancy socks and black shoes with a two inch heel. I was not sure I should do this with all the people that were going to be there, but I knew I would have to, so with mixed emotions I put them all on. The dress was not short, but it was not really long either. The petticoats made it flare out and it came down to just above my ankles. It felt really good and I liked to have it flounce when I moved. I looked at myself in the mirror and I looked like a boy in a dress and I was still very nervous about going out. Linda’s mom came in the room and said she had one of my surprises. She had in her hands a very pretty long brown wig. She put it over my head and the hair fell on my shoulders. She then brushed it a few times and told me to look in the mirror. Linda put some lipstick on my lips and rouge on my cheeks and I finally looked like a 12-year-old girl. I was really excited and I felt that now I could go out and be Linda’s "girlfriend". Linda’s mom said I looked like a very beautiful sister of Linda’s.

Linda had on a similar dress but it was in blue to match her eyes. I really felt proud to go out with her now. I don’t remember much about the services, but we did talk to several of Linda’s friends and she just introduced me as Nadia her girlfriend. That was a big highlight for me and I will always remember that day. Her mother took several pictures and after we got home, Linda and I kissed a lot on the couch.

Linda’s mom went to the store and left us at the house. Linda and I were kissing and touching each other and then Linda kept whispering in my ear that I was her girl and how great it would be to have breasts like hers, then she kept touching my penis and after a while I got hard. She moved the dress and petticoats so she could get her hand on my penis and she kept touching it softly until I eventually came in her hand. She then licked half of it and gave me the rest. She said one day she wanted me to lick her down there, but I never got a chance to. Gosh, it felt so very good and I even liked the taste. She made me feel great all that day.

Her mom came back and we were just sitting there kissing each other. She said that she had to take me home now. I was very disappointed but I knew I had to return home. She said for me to take the dress off but not the makeup and she would bring me my other surprise gift. I reluctantly took the dress and petticoats off and the Linda came in the bedroom and told me I could keep the panties and bra and she then handed me a cheerleader’s uniform. Linda told me she had four of them and I could have this one. I was thrilled with it. I put it on and it was very short, as short as the tennis dress I had on earlier. I still had the wig on and I really liked how I looked. We went ahead and got in the car to go home. I had a small bag with my clothes I had worn to school. Linda’s mom told me I could come over once a month and we could have fun together. I was really happy. When we got to my house, Linda’s mom told me to take off the wig so I could have it next time I visited. I really did not want to, but I knew I had to. Now, here I was wearing a cheerleader uniform and my short hair and having to go in my house alone. Linda said she would walk me to the door, which made me feel better. Luckily, only my sister was at home and she laughed at me and told me to go get changed before Dad got home. Linda told her I was just wonderful and behaved like a nice little girl for them. My sister said that she was pleased I cooperated with them and thanks for inviting me over. I went and gave Linda a kiss and she kissed me and I went up to my room.

Over the next year I went over to Linda’s house once a month. Her other girlfriends were there when I wasn’t, apparently wearing the same clothes I got to wear. They moved after that and then when I was 13, we moved to Texas and my cross dressing experiences became a lot less frequent. More about each of those experiences later, but I will never forgot those times with Linda and her mom.

 

 


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