When I was little, my sister used to dress me up in her clothes and we used to play together. She was only a year and half older than me and she would doll me up most of the times and pretend that I was her sister. My mom didn’t really mind her dressing me up and thought it was cute that we played together.
Growing up, I also began to have fascination with girl’s clothes especially skirts and dresses. As we grew older, my sister didn’t have much time for me. Instead, she would hang out with her friends most of the times. Now and then I would get this strong urge to dress up as a girl and I tried resisting it but the urge would just get more stronger.
So, I started sneaking inside my sister’s room when no one would be around. I would dress up in whatever clothes I could find in her room, pose in front of the mirror, then change back and go back to my room. It wasn’t enough for me so I started sneaking some of her older clothes into my room and crossdress every night. It was so much fun and I loved dressing like a girl.
As time passed by, I wanted more. I wanted to wear bra, panties, hair wig, makeup, shoes and just everything girly. One time, I sneaked into my sister’s room and stole her old bra and panties. When I wore bra and panties for the first time, the rush was unbelievable. I felt so feminine and beautiful.
After that moment, I would always wear bra and panties when I crossdressed. Soon, my sister started noticing that some of her clothes were missing and told our mother about it. She asked me too, I was super nervous but I just told her I had no idea.
After that, my sister started locking her door whenever she left the house. I was sad that I could no longer wear her cute outfits. Then, I decided to get some new clothes and accessories online. It was so exciting to enter the online world of shopping. I would spent hours and hours browsing through shopping websites for dresses, makeup and shoes, imagining how I would look in them.
Finally, I order my first batch of items, it was a blonde hair wig, a white dress, a nude sheer pantyhose and a black pump. I was super excited. I made sure that the items would be delivered when my parents and my sister was out. I was so restless for few days until the items finally arrived. I was pretty nervous to receive the package from the deliver guy when it arrived but I just couldn’t wait to try everything on.
I rushed to my room to check out the items and everything was as expected. The quality of the hair wig really impressed me, it really looked and felt like real hair even though it was a synthetic hair wig. Wearing the hair wig for the first time was bit of a struggle but I was shocked by how much it changed my whole appearance. Not only did I look like a girl, I felt super feminine and cute having long hair.
Then, I put on my sister’s old bra and panties that I had, stuffed the bra cup with some socks and then put on the new dress. It was a bit tight around my shoulder but I managed to put it on. Next came the pantyhose and I loved how it felt on my legs. Lastly, I put on the new pumps and my transformation was complete. It was so much fun than I expected. I was really loving how I looked and couldn’t stop posing and admiring myself in the mirror.
Since, no one was home that day, I decided to step outside my room and stroll around in my new looks. It was so exciting and I could feel my body trembling with a new sensation as I stepped out of my room. I walked around the house and walking in heels was so much fun. I knew this was just a start to my crossdressing journey.
After that, I started to dress more often in the house, order more items online and started to get a lot better with my feminine transformation. I could do my makeup better, I could walk in heels better and my body posture and movement became more feminine.
One afternoon, my parents were out on a trip and my sister told me she was going out to her friends house and will only come back in the evening. When she left, I immediately opened my closet and took out my hidden girly stuff and started getting dressed. I choose to wear a pink floral dress, black pantyhose and my favorite black pumps and of course my blonde hair wig. In about 10 minutes, I was fully dressed from head to toe. Then I put on some makeup which took me about 15 minutes and I decided to do some photoshoot in the backyard.
As I walked out of my room and was passing by my sister’s room, I noticed that the door was slightly open. Usually, she would lock the door when she left. Maybe she forgot to lock it this time. Suddenly, my heart started beating faster imagining about the possibility of wearing some cute outfits of my sister. I went inside and looked around. There were some clothes hanging in the hanger but nothing exciting. I went to check if the closet was open and it was. My excitement was out of the roof as I opened the closet.
There were so many items and I was dazzled completely. I couldn’t decide what to wear, there was so many choices. After looking around for a bit, I decided to first try out one of her pink pleated skirt and a white top. I took off the dress I was wearing and put on the top first and then the skirt. I simply loved the look. When I looked at myself in the mirror, I couldn’t stop smiling.
My sister also had a lovely collection of shoes and she had a shoe rack with so many lovely shoes. I decided to try them on but unfortunately, her shoe sizes were much smaller than mine. I could barely insert my feet in them but at least I could fit into her clothes. As I looked around, I noticed her perfume collection and splashed myself with one of them. It smelled so fruity and feminine. I loved it. I was having the time of my life.
After taking lots of photos and videos, I decided to change into another outfit. As I was going through her closet once again, I heard the front door of the house open. My heart stopped, my body was completely paralyzed. Then, I heard my sister calling out to me that it was her back home. I knew I didn’t have any time to take of the clothes so I rushed to get out from my sister’s room. As I reached for the door, my sister open it and she screamed when she saw me. I was so scared and embarrassed.
She screamed out ” Mike? Is that really you? What the hell are you doing? You sacred the sh*t out of me! Is this some kind of prank? I am gonna tell mom now..”
For a moment, I couldn’t speak or even look at her. I was too ashamed of myself.
My sister screamed at me again ” Are those my clothes? Why are you in my room? This is so weird…”
I told her I was sorry and tried leaving the room but she didn’t let me.
She told me ” You need to explain all this to me first before you leave.”. She then took out her phone and started taking pics of me. I was so embarrassed and begged her not to do so. But she was too pissed and said she was going to show it to mom and dad.
I was so sacred at that point and I apologized to her many times for wearing her clothes. I tried to explain it to her but I was so nervous standing in-front of her dressed like I was. It was so embarrassing. Then slowly, I managed to tell her about my urge to dress as a girl and how it started from our childhood, with her dressing me up when we were kids.
She listened to the whole thing silently and took some time to process it.
Finally she spoke ” Okay, I can understand but I never imagined you liked dressing as a girl. Answer me honestly okay. Are you gay?”
I said no and told her I only liked dressing as a girl now and then.
She asked me if I have been wearing her clothes secretly and I said no. I told her I brought few items online and only dress in them.
She told me she wouldn’t tell mom. However, she made me promise to never sneak into her room and wear her clothes ever. I nodded and she asked me if I wanted to talk about my crossdressing with her and I said okay. She did catch me wearing her clothes and I had nothing to hide from her so we talked for sometime and my sister was pretty supportive. She also told me that I had to think about it carefully and if it was really something I wanted to do.
After we were done talking, I felt much better. I gave her a hug and she told me I did look cute as a girl. I blushed. She said I could keep the clothes I was wearing and I said thanks. After that point, my sister was very supportive and she even took me out shopping a few times as a girl. After a few years, I came out to my parents and they were understanding. I felt so light after confessing to them. But I never dressed in front of them.
After college, I moved out and have my own space now. I dress a few times every week as work keeps me super busy but I am happy that my sister caught me crossdressing that time. Otherwise, I would never have the confidence to talk about it to anyone. I know I am super lucky to have such understanding sister and parents. I have read many other crossdressing stories where it didn’t turn out well. But my advice to any closet crossdresser is to try to talk about it with the right person and give them time to process it. It can really help to become your true self and be happy.
Submitted by Mike