I used to go every summer holiday to stay for some time with my grand mom. At the time when I was 8 years old my parents moved into a new home and I spent a longer time with my grand mom. I have a six years older sister who was no longer coming to stay with me there.
I always have been with slim body, long thin legs and 100% girly butt which I still have after so many years, I had long blonde hair reaching my shoulders which at later stage changed to dark brown and blue eyes. Now and again I have been mistaken for a girl even in my own clothes which in most occasions made me feel embarrassed. I had friends and I was getting on well with most of them but I was not the most popular boy. I was from poor family and hardly had anything material as that is the way it works most times and I don't recall anyone ever giving me some extra attention in any way.
One day I was with few friends at playground with a slide that was damaged at the bottom and when we took turns going down almost all of us jagged our shorts including me. I went home couple of times to put on a new pair and manage to jag all of them. Later in the day when my grand mom seen what I have done asked me to clean myself and take a shower and she washed my clothes. I had nothing to put on as the rest of my clothes were for more cold weather and she looked true my sister clothes and give me a short orange dress ( that was just right for my size at the time) with shoulder straps, white panties and white sandals with almost 2 inches heels. I wondered why I had to put on the sandals but didn't make any problem. I din't want her to be looking at me while changing and ask her to get out of my room. I got myself all nude and start outing on my sister clothes. The feeling of that soft material from her panties and the thin fabric of her summer dress touching my body made me feel instantly so different and in no time I got transformed into a little girl. I was shivering in excitement remembering how we did a role play the last summer and I had to play the wife with the rest of the boys as we had no real girl among us. It felt somehow natural been in that role but I never thought about that again until the moment I was in my sister dress. I probably looked at myself at the mirror for 10-15 min before I got out of My room. My grand mother looked at me smiling and joked she got 2 grand daughters now. The she left me alone and home and said she will go out for some shopping and also will buy me new clothes. I went back in my room looking at myself in the mirror and really thought I am looking so much just like my older sister. After another 15 min or so I went out on the veranda and took a seat near the end to our neighbors garden hiding from the sun. Our veranda could be seen well from their top part of the garden. As I was seating I was seen by one of the two boys brothers living next door (by the older 15 y old). He could not make out who I was and how never had seen me before. He called me to get close to the fence and I made my first steps on heels and that short thigh dress and surprising to myself I managed to walk real well. I'm same time I was very anxious how would explain why I am dressed like that. He start talking to me as never before ever so kindly. His eyes were at all time on my thin body and asked me who I am. I start talking looking at the ground and explaining what happened at the slide. I was surprised that even talking he couldn't figure out it was me. As I told him my boy name he was finally realized my transformation and I could tell his amazement was so big. He never really talk much to me as a boy as his younger brother was my friend but I could tell he had real interest in me this time. He told me that I am looking more beautiful than my sister and she was pretty good looking. I could feel my cheeks were going red and even felt a slight breeze true my bare thighs under my dress. He asked me to go over to their house and watch TV with him. It took little convincing as I wasn't very keen to be seen on the street dressed as girl, but he made me go out. He was waiting for me at the gate. I looked bit nervous on the street hoping none of the other neighbors were out. I must have been very sexy looking girl as his face had such huge smile. Just before getting in their house we seen a friend of his coming over to see him and who looked me in the very same way and when we talked he had no idea I was the boy from next door. My neighbor looked at me and make sing not to tell who am I . We all walked in the house as he got hold of my hand in front of his friend like I was his girlfriend. He asked his friend to get in the living room and told him we would be their shortly to get to the kitchen and bring some soft drinks. I felt so exited and could feel my knees tremble. He asked me to relax and play his girlfriend and that I am one of the granddaughters that have not visited before. He assured me he would never find out if I don't tell. I bid my head and follow him with glasses in my hands. We sat in the sofa a cross if his friend. He served the drinks and got the TV on. Then took a seat next to me and put his hand over my shoulder and fixed my hair a bit which was reaching just bellow my shoulders as I was seated. I somehow managed to realize and cross my legs one over the other exposing my bare thighs but also in the same time trying to hide what is between them. My new boyfriend rest his hand over my bare leg and was really showing off. The feeling of having his hand on my thighs was much better that I could ever imagine. I realized that moment I was born in the wrong body and been a girl was coming so natural to me. For first time I start looking at my neighbor as a girl would look at a boy and was enjoying every bit of attention. He did most of the talking and manage to help me hide my anxiety which turn into confidence after while believing I really can pass as girl. I noticed how the other boy was keep looking at my legs and knew I have some real weapon I can use in all the boys I was going to meet in future. My new boyfriend even kissed me couple of times on my cheeks in front of his friend and I even expected him to do that. He noticed I do not resist him on been kissed and when I told him is time to go back home as my grandmother may be worried for me he got up with me and in the way out hold my body with one hand on my ass cheeks and the other behind my back and kiss me on my mouth. That was the best moment of my life so far.
Later at home I dint want to get off my sister clothes for long time keep looking at myself at the mirror. I realize I was born in the wrong body and ever since been so sad I can't change that.
Originally Posted by emilyshine
