My name is James. When I was in high school, I started getting fascinated by girl’s school uniform that girls in my school wore. I often fantasized myself dressed as a girl and coming to school as a cute girl.
I have an older sister who is 3 years older than me. She and I are very close and we share almost everything with each other. One day, when mom & dad weren’t around, I asked my sister if she could keep a secret, to which she replied that she would.
I was nervous to speak at first but I finally told her that I kept having an urge to dress up as a girl and feel what its like. I could tell she was pretty surprised by what I said. After some minutes of silence, she asked me if I was joking? But I told her it was the truth.
She then asked me if I was gay? I said I wasn’t really attracted to boys but I just wanted to dress up as a girl and feel cute. She asked if I had dressed up in girls clothes before and I said no. My sister then opened her wardrobe and took out few of her old dresses. I started feeling quite nervous while she was taking out those dresses.
My sister then handed over some of her dresses to me. She asked me to try these on and show her how I looked. I took the dresses and gave her a hug. She smiled and I went to my room to change. I felt a burst of excitement that I had never felt before. I removed all my clothes and decided to wear a white floral dress first. I put them on and immediately I fell in love with how nice it felt to wear a dress.
I looked in the mirror and I couldn’t stop admiring the dress and myself. If only I had long hair, I knew I could really look like a girl. Then I heard my sister calling me and I got very nervous with the thought of walking in front of her while wearing her dress. I slowly walked out of my room and everything felt so different when wearing that dress. I hesitated for a bit to enter my sister’s room but she kept calling me.
When I finally walked in, she looked at me from top to bottom and said not bad, the dress fits you pretty nicely. I blushed. She asked me to come near and showed me a zip at the side of the dress. She pulled it up and it felt like a perfect fit. I just loved how the dress felt in my body.
To my delight, my sister told me I could keep those dresses and wear them whenever I liked. She shocked me by saying that in the coming weekend she would take me shopping for some girly clothes and accessories. I felt very lucky to have such an understanding sister.
Over the next few weeks, my sister got me a new dress, a padded bra and a pair of white stockings. She would give me makeovers and give me tips to present myself more like a girl. We would hang out a lot together and check out women magazines, talk about fashion and other girly things.
It was two weeks before Halloween, my sister had a crazy idea to dress me up as a girl for Halloween and show our parents and few friends. I was spooked by the idea and told her I was just too afraid if they will not like it. My sister convinced me that nothing bad will happen and it will be fun. I finally agreed and she made a plan for Halloween where we would both dress as glamorous Victoria Secrets models. It did sound very exciting.
On the next week, my sister brought me a blonde wig and a pair of black heels. She showed me how to put the hair wig on and when I wore it, she was as surprised as I was with my transformation. She told me I really looked like a girl now.
I realized having long nice hair could instantly make a person look more feminine and pretty. I now looked more feminine in every outfit than before with the hair wig on. I started styling the hair wig to match my face and after some practice, I was able to style the wig better. Every night when everybody was asleep, I would get dressed and also practice walking in heels and work on my feminine manners & postures.
When Halloween arrived, I was super excited. My sister and I started getting ready in her room. I was about to receive a complete makeover by her. She told me how much she liked giving me makeovers and felt like I was her little sister that she never had. I blushed and gave her a big hug.
Then she showed me two dresses and told me to choose one. Both were mini-dress, one was purple and the other was black. I picked the black and she said she would wear the purple one then . I went inside the bathroom and removed all of my clothes. Then, I put on the padded bra and panties, nude sheer pantyhose and the black dress & black heels. I loved how the dress hugged tight around my body and it felt so feminine wearing them.
Lastly, I put on the hair wig last and styled it. I was so happy to see my reflection in the mirror. I felt cute and beautiful. I couldn’t stop blushing. I stepped out and my sister was so pleased with how I looked and kept teasing me. She said now guys would be hitting on me and girls would be so jealous of my looks. I couldn’t stop smiling.
After my sister finished getting ready, she started to do my makeup. She moisturized my face, then applied some foundation and smoothen it out with a makeup sponge. After that, she applied some concealer cream and matched the complexion overall. She then did my eyes and put on eye liner, mascara and some eye shadow.
She also brushed my eyebrows and highlighted the shape with an eyebrow pencil. And lastly, applied a matt pink lipstick on my lips. I loved how girly I looked with the makeup on. I thanked my sister for such a wonderful experience. She told me it was just the beginning. We took a couple of selfies and videos and it was so much fun.
Then she told me it was time to go downstairs and show our parents. I started getting nervous again but my sister took me downstairs to show our parents. I could feel my heart beating so much faster and I was so nervous.
When mom and dad saw me, they were completely amazed how good I looked as a girl and couldn’t believe it. Everyone laughed and my sister kept teasing me. We had some drinks and snacks. I was still a bit uncomfortable but I was glad mom and dad took it pretty well.
Suddenly, my sister told mom & dad that she and I were about to go meet some of her friends and hang out. I was shocked. I didn’t know she had a plan to go outside. I was just too shy & scared to go outside and let other people see me as a girl. I refused but my sister was not taking no for an answer.
She made me get up and as we walked towards the door, I begged her not to take me and meet her friends. She said she knew I would be scared for the first time to go out in public dressed as a girl but this would be a great chance for me to finally feel like a girl . I understood what was trying to say and agreed to go out.
She handed me an eye mask and told me to put them on. She said it will make me feel more comfortable and it did. Now, I had more chance to not get recognized by people whom I didn’t want to see me dressed as a girl. We walked out of the house and it was like I was going out for the first time. There was this huge rush inside my mind and body, I felt so exposed and vulnerable.
Taking the first few steps were very scary but having my sister with me started giving me more confidence. That evening, I meet some of her friends and she introduced me as her cousin from another town, everybody was so nice. We walked around the town and we all had a great time. One of my most amazing experience in my crossdressing journey.
Submitted by James (Justine)