Crossdressing in Sister’s Clothes & Makeup

crossdresing in sister's clothes

“Hi, my name is Nick. Here’s my little story about crossdressing in my sister’s clothes.”

“Since my childhood, I was somehow interested in women’s clothing. At the age of 6, I tried on a dress for the first time. It was my sister’s dress. While growing up, I was so fascinated in girl’s clothes. I imagined myself in cute dresses and skirts most of the time. It was very hard to explain why I liked it. But I just wanted to dress like a beautiful girl. But I could barely get a chance to dress up because there was no privacy and I was just too scared to tell anyone about my crossdressing.

However, having a sister made it easier for me to start my crossdressing adventure. I tried on her clothes secretly. It felt so different and very exciting. I loved everything about it. I searched the internet to find more about the desire to dress like the opposite gender. I found out that there were many people like me who loved dressing up too. This was a bit of a relief to me to know about.



I tried to fight the urge to dress up, but every time I was alone in the house, I just couldn’t stop myself from going to my sister’s room to see if there were any clothes that I could try on. Most of the times there was and I would just dress up in them and enjoy the feeling.

By the time I was 16, I had a small wardrobe of girl’s clothes myself. I also brought a black hair wig and a pair of high heels. I started to dress up more frequently. I was usually spending my time dressed up most of the time in my room. I enjoyed taking photos and videos. I even used to go to bed fully dressed up sometimes. It was just amazing to see myself as a girl. I didn’t really feel that I was a transgender though. I just loved to dress up every now and then, and enjoy the feminine experience.

But the clothes I had brought myself were never enough. I usually got bored with them in a short time. However, my sister had many clothes. I would sneak into her room when I could and try to find something I liked and took it for some time. I nearly got busted many times but I got away with it until one time.

There was a family event in my grand parents house. I had an exam coming up so my parents decided to leave me behind. My sister had also gone with her friends for short trip the day before. My parents were going to be away for two days. I was so happy to know I could dress up fully in the house and try on all the things I always wanted to try.

As soon as my parents had left in the morning, I rushed to my sister’s room to get my hands on my sister’s lovely outfits, makeup and heels. I was lucky that her clothes usually fit me well. I opened her closet, there were just so many outfits I wanted to wear. There was her school uniform, a white floral dress, a pink lace mini dress and a denim skirt & green top combo. I got some of her makeup too – eyeliner, foundation, mascara & lipstick. I took all those stuff in to my room and started to get ready.

I got undressed, put on a padded bra and panties. I decided to try the school uniform first. I put on the white shirt, next the grey pleated skirt. After that, I wore the tie and socks. I then started to put makeup on. I had a little experience but I was not that good with makeup. I had some time in my hand this time so I decided to be very careful about applying the makeup.



I started with the foundation, then the eyeliner and mascara and lastly the lipstick. I loved how I looked. Then I put on the hair wig and lastly my sister’s school shoes too. I figured, I might as well dress up properly this time and indeed I did. I was looking like a cute school girl and that skirt was making me feel so feminine and cute. I was really enjoying myself. I went back to my sister’s room because she had a large mirror in her room. I just couldn’t take my eyes of myself and it was just amazing how I felt at that moment. I started to take a lot of photos and videos. I was loving every bit of it, in fact I forgot it was already late afternoon pf the day.

I decided to eat something and this time it would be really different. I was going into the kitchen fully dressed as a girl for the first time in my life. How amazing it was, I was really happy I was able to experience such lovely time as a girl. I made a sandwich and coffee. I sat in the kitchen table and ate my meal heartily. It was so relaxing and lovely. Then, I washed the dishes and walked around the house taking pics & videos of myself. Then as I was in the front part of the house, I was right behind the front door. I had never stepped out. I felt such a rush to go outside. It was something I had never felt. I was getting very excited and aroused. I peeked through the window to see if there was anyone outside. I looked quite dry. I decided to step out. I slowly unlocked the front door. My heart began to race. I checked to see if there was anyone on the road. Then I took the first step. A rush like no other hit me with every step I took outside the house. My eyes moving everywhere to see if there was anyone who was watching me. I took out my mobile and started to take some pics and videos. As i was doing so, I heard a car coming. I panicked a little. I decided to go inside before it passed me. But as I was about to reach the door, I could see the neighbor’s front door opening. I jumped towards the door and slammed it behind it. It felt really scary. Had the neighbor seen me all dressed up now? I was nervous. I peeked through the window to check out but it was just Mrs. Hedge spraying some water on her hanging plants in front of her door. I was relieved.



I went up to my room thinking what I should do next. I decided to wear the pink lace dress with pantyhose & high heels. I took off the school uniform & began to dress up in the cute dress. I loved this outfit too and it felt great to wear. I looked sexy. I started taking a lot of photos & videos for like almost an hour or so. Then, I felt tired. It had been a crazy day with so many new things that I experienced. I went back to my sister’s room and got into her bed. I then checked out all the photos and videos that I took and deleted the ones that I didn’t liked.

As i was wondering around, I saw a nail polish bottle. I felt like painting my nails, which I had never done before. So, I played some music and started to paint my nails. I was really enjoying it. Painting my nails made me feel so feminine. It was my first time so I was being careful to put the polish on. It took me 15 minutes to put polish on one hand. As I was finishing to put polish on the last finger, the door suddenly and there was my sister. We both screamed when we saw each other. I didn’t hear her with the music on and I forgot to lock the door in the front. We both were quite taken into surprise but she was much more than I was. At first, she didn’t seem to recognize who I actually was. I was quite embarrassed myself. When, she realized it was me, she finally spoke “Rick?? Is that you? What’s going on?”.

To be continued…

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