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Long Time Crossdresser
It started when I was pretty young. I want to say around 2nd grade. I went to my aunt's house for my cousin's birthday I believe it was. I was in the basement playing games when a little pink suitcase got brought out. Inside was a bunch of dresses and costumes that belonged to my cousin. All of the kids decided to dress up. Even the boys and of course myself! I don't remember what I was wearing, but I'm pretty sure it was some kind of disney princess dress. We all continued to wear them for the rest of the evening. It was a very weird night, needless to say. There was one point where I went upstairs and even walked in front of all of the parents sitting at the kitchen table! Nobody really said anything, because I'm pretty sure they already knew what we were all doing, and just accepted it as a weird game. Some of them even gave a little cheer which made me feel weird. At the end of the night, we all put everything away in the pink suitcase and went on with our lives like nothing happened that day. Little did I know how much this day would change my life! For a while, I continued to secretary put on those outfits whenever I came over. I really enjoyed them!
Fast forward about a year, and I was in the basement at our own house by myself playing video games and stuff. I saw this pink shirt sitting in a bag of other clothes. No doubt that it came from my sister. I suddenly remembered that night at my aunt's house, and I got the thought of what it would be like to wear it. I ignored it at first, but a couple days later I continued to look at it and those thoughts grew stronger. I was completely by myself, so I finally caved! I took off the shirt I was wearing, and put on the pink one! It felt really good, and the rest of my time in the basement was spent wearing it! I almost got caught because my mom opened the basement door and called my name. Thankfully there were walls around the stairs, so she wasn't going to see me unless she actually came down. I responded to her like normal, and was thankful that she stayed by the door and left after a couple minutes. I continued wearing the pink shirt until I decided to put my original shirt back on and go back upstairs.
After going down and wearing the shirt a few times, I found more clothes in the bag that it came from. I decided to take things a little further and brought the bag over to the crawlspace. I climbed in, and used this piece of plywood sitting next to the entrance to block it shut like the world's ** door. I took out more of my sister's old shirts from the bag, and started putting them on. I was too young to understand at the time, but I was feeling aroused while I did this! I put on every shirt at once, and then tried a few of my favorites by themselves! They felt so good to wear! After a bit, I put everything away, and got my own clothes back on. I then sat the plywood door back down and got out of the crawlspace like everything was normal.
Eventually I decided to take one up to my room by wearing it under my own shirt! I almost got caught again because I ran into my mom heading into my room. One awkward conversation later, and I was in privacy. I hid the shirt in my bottom desk drawer, and started wearing it to bed. I could only do it on weekends though, because during the week my mom would come in to wake me up for school by rubbing my back. She would surely notice the shirt even if I did conceal it! I got some of the other shirts that I liked and started wearing them to bed as well! Eventually I moved everything to be hidden between my mattress. I knew they would be safer there.
After a while, I actually stopped doing this. I went a few years without dressing up at all. Then around middle school I remembered my time doing it, and it all started back up again. This time I started wearing dresses! Both from my mom, and my sister! I could only take things that were already getting donated though. Everything else had to stay in their spots in the closet/dresser since I didn't want anyone to notice they were missing. I really enjoyed wearing them though! This was around the time that I hit puberty, so I started masturbating too! Doing that while wearing my sister's dress was so good! There were times when my sister would stay the night at a friend's house, and I would take advantage of that time to sneak into her room and wear something of hers to bed! Of course it had to be a dress most of the time. I would sneak back in the next morning and put it back. She was none the wiser (I think.)
One day I had a friend stay the night, and I forgot to put my stash of clothes in the crawlspace like I normally would've. He noticed me acting weird about the matress. I was pretty much forced to let him see my secret since he wouldn't let it go. Right as he looked, I stepped out of the room because I didn't want to be there for his reaction. I quickly thought of a way out of it by playing it off as a joke when I came back. It seemed to have worked, but I have doubts that he truly believed such a blatant lie. I wonder if he still remembers it
Today I am an adult. I still REALLY enjoy crossdressing, and now I have money to spend on my own stuff. It's mostly pink and obnoxioisly girly dresses and other outfits! That's just how I like it! I recently bought this adorable Pinkie Pie dress costume from AliExpress. I don't even care about the show at all, but you can look it up to see what I'm talking about! I literally just bought it because of how cute and girly it looked! I'm so excited to try it on when I get it! This is a great example of just how girly I like it! I have other dresses, costumes, swimsuits, and cheerleading uniforms of this same style of pink and obnoxiously feminine! I particularly enjoy skater dresses! I like the ones with short sleeves and the skirt that ends right above the knees. Those feel the best to wear!
The only person who knows about it is my brother. He came into my room when I was working trying to find something, and he accidentally found my secret. It turns out that he also crossdresses! I don't think he's into the really pink and girly stuff like I am. He does have a few dresses and stuff though. He's tried to get me to dress up with him a few times, but I'm still just not comfortable with doing it outside of my own privacy. Maybe some day, but for now my crossdressing stays in the closet
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