Crossdressing Storieslatest

Turning into my Sister

Crossdressing in my Sister clothes

When I was 10 years old, my twin sister talked me into wearing one of her frocks. I agreed and she dressed me up in one of her frocks and we played together with her dolls. I still remember that moment clearly and how nice it felt to wear her lovely frock. That moment changed my life forever. 

Since then I started having the urge to dress like a girl and every time I had a chance I would sneak into my sister’s room and try on her outfits. It felt so good when I wore her outfits, especially her school uniform. As time passed, I grew more and more interested in feminine clothing and to look like a beautiful girl.



My parents both had a very busy work life and most of the times it would just be me and my sister. When my sister was busy with something like when she was taking a bath or watching Tv downstairs in the living room, I would sneak into her room and try on whatever clothes I could find and then take them off again and get back to my room.

It gave me such a rush but it wasn’t really enough for me. I thought about telling my sister about my urge to dress up as a girl but I was scared she would tell mom and dad. So, I just kept it a secret. 

When I was 14, I found a stash of my sister’s old clothes in the attic. I took few of the clothes which I thought would fit me and hid them in my closet. I would get dressed every night in my room and enjoyed dressing up. But wearing the same clothes again and again started to get boring. I wanted to wear makeup, cute dresses and look like a cute girl. 

I started to spend a lot of time online looking at boy to girl transformations, crossdressing and male to female makeovers. I was glad to find out that I wasn’t alone and there were a lot of people who liked to dress up as a girl too. I loved looking at photos & videos of boys who dressed as girls and makeup tutorials. I actually learned quite a lot about crossdressing. So, I decided to get some stuffs online for my own transformation.



I saved some money and order my first hair wig. I arranged to receive it when my parents were not at home. When it finally arrived, I couldn’t contain my excitement. I just couldn’t wait to try it on, my heart was beating like crazy. I rushed to my room, unboxed the package and pulled out the neatly packed hair wig. It looked like what they had shown in the picture. It was a long blonde lace wig.

At first, I had some problem placing the wig properly. Then with some more try I managed to have it placed decently on my head. When I looked at the mirror to check out, I just couldn’t believe how good I looked. In fact I looked quite like my sister. I felt really cute and it made me blush.

Then I undressed myself and put on an old dress that I had. I couldn’t stop looking at the mirror. I looked so much like my sister and I felt like a girl. I must have taken hundreds of photos and videos of myself. It was a very exciting experience.

After a week, I had tried the hair wig with all the outfits that I had. It certainly changed my appearance a lot and made me look so much like a girl. I started trying different hair styles with the hair wig and particularly liked having it in a piggy tail style which my sister also frequently used to do with her hair. We both looked so similar and it was surely because we were twins.



One day, my parents were away and my sister told me she was going to her friend’s house and would be back in the evening only. I was super excited because now I could get dressed and move around the house openly. When my sister left, I just rushed into her room to see if I could wear any of her nice outfit. I found her bra, a black crop top and pink pleated skirt. I just couldn’t wait to try them on.

I quickly went to my room to get my hair wig. Then I got back to my sister’s room and got undressed. I put on the bra first, then the crop top and finally her skirt. It felt so nice to dress up in those clothes. My whole body was tingling with joy to be wearing such a cute outfit.

Then I put on the hair wig and styled it in a piggy tail.  When I looked at the mirror, I couldn’t believe how cute I looked and so similar like my sister. In fact it was like I had really turned into my sister. No wonder it was because we were actually twins. It felt like my reflection in the mirror was my sister looking back at me.

I felt so girly wearing the outfit and couldn’t stop admiring myself in the mirror. Simply loved how I was looking in that outfit. After taking quite a lot of pics, trying different pose here and there in the room, I decided to go out to the living room downstairs.

It was like a fresh breathe of air as I moved around the house. I had also put on my sister’s sneakers lying in her room, really glad that all of her stuffs also fitted me nicely. Now my look was complete from head to toe and I was so happy to experience my time being a girl.



I must have taken hundreds of pictures in different places of the house that my phone warned me of low battery. I looked at the clock and thought there was still time to enjoy being dressed for another 1-2 hours. So, I put my phone to charge and went to my sister room to find some makeup to apply.

I found some lip balm, eyeliner & mascara and decided to put them on. I had never tried them before and it was exciting to be applying them in my face for the first time. I first applied some lip balm and my lips looked so sparkly. Then I tried to put on the eyeliner and I found out that it was not as easy as I thought it was. I made a complete mess and I had to wash it off and try again.

Finally, I was able to draw a nice line of eyeliner and decided not to get too ambitious with it. Then I moved on to the mascara and applied it somewhat randomly. I looked at the mirror and was quite happy with the result. It wasn’t bad for my first time applying makeup. I definitely looked more girly with the makeup and it was super fun. 

I went to grab my phone and started taking photos again. I definitely wanted to save these lovely moments of me as a girl. Just then, the bell rang and I felt my heart stop. Was that my sister or someone else? I couldn’t be seen like that? Was I really busted? All these thoughts came rushing in my head. I panicked not knowing what to do. There was no time to take off the makeup & outfit and go open the door. I was scared and I knew I was busted. So, with every ounce of courage I had I stepped out from my sister’s room to grab a peek of who was at the door.



My heart was pounding and my body trembling. I felt so exposed and vulnerable while slowly coming out of the room. The bell rang again and it spooked me again. It must have been such a funny sight of me as I was crawling slowly to the window to see who it was. I finally got near the window upstairs and slowly looked who it was at the door. 

It turned out to be a delivery guy. I was a little relieved. I asked myself whether I should go down to greet him dressed like that. I knew I was too nervous for it but I had to do something. I wondered if he would notice me as a girl? Nobody had seen me like a girl before and this would be the first time. Should I do this? Thoughts were racing again inside my head.

Just then I heard the noise of package being dropped on the floor. I looked from the window and saw the delivery guy turning around to leave. He must have thought no one was home so he placed the package in-front of the door. That was a close call, I thought. I heard the delivery van finally drive off and decided to go down to get the package. I slowly walked downstairs, still a little shaky and got to the door. My heart began beating faster again just thinking about opening the door. I took some moment to calm down.



With a deep breathe, I opened the door, grabbed the package and  shut the door. A few seconds just felt so long. Did anybody see me? It was such a rush. The package was for my dad, must be something he ordered. I placed it on the table and went back to get undressed  and wash off my makeup. I didn’t wanted to stay dressed longer and risk being caught.

So, I got back to my sister’s room and took off all the clothes. Then put everything back as it was and went to my room to clean the makeup. I took of the wig, washed my face and put on my boy clothes. After I freshened up I went to my sister’s room again to check if everything was placed back properly. Just then, the door bell rang and I had a mini heart attack.

I walked out of the room, checked my face in the lobby mirror to see if there was no  trace of makeup and then went downstairs to open the door. It was my sister. I opened the door, glad  that I decided to undress a little earlier. I then went back to my room. This was an experience I would never forget. The day I turned into my sister.
The End

– Sent by Ariana

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2 Comments

  1. Similar story to my situation

  2. That was so hot. I thought I wish I was that delivery guy, and you answered the door all dolled up. Then we…..? You tell me.

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