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Hello! This is my first time posting here but I’ve spent a lot of time lurking over the years. I realize there have been a lot of interesting crossdressing moments in my life, particularly before I was 12 and quite often involving my sister. I wanted to share some of them as I love reminiscing and don’t often get to share these with anybody lol. I did tell this on another forum recently but wanted to share here as well.
Like I said, I have a sister who’s 4 years older than me and we were basically the same size until I was about 15. Of course I would occasionally “borrow” whatever clothing I could get my hands on and admire myself in the mirror. It may seem a bit creepy with hindsight, and I was caught at least once, but I want to talk more about specific events where things got a bit more involved. I must’ve been 6 (maybe 5,) and my sister and I were watching the movie Bring It On on cable. She did cheerleading at the time, so she had this idea to dress me up in her outfit as we continued the movie. I didn’t really understand it, but I was na?ve and went along. I don’t remember anything about the color or wearing any other articles of clothing, but it was a one piece uniform (as it was for kids.) We continued watching the movie, and we would dance around and try to match their routines. My mom eventually discovered us – she wasn’t mad but she did make me change. I always had an affinity for my sister’s cheer outfits after that.
One of the next big moments happened about a year later. My grandparents’ house has a pool and we would often go over to swim. We’d usually keep our swimsuits over there since their house was the only place we’d go swimming, but for some reason mine couldn’t be found. Maybe we brought it home and forgot to bring it with us, or it got misplaced in my grandparents’ laundry. My mom definitely wasn’t going to let me swim in my jeans, that was for sure. While my brothers jumped in the water, my mom, sister, and I looked around for them. After the two of them talked a bit, my mom asked if I wanted to try on some of my sister’s bikini bottoms since she had at least 4 or 5 swimsuits at the house. By this point I knew the magnitude of what wearing them meant as a boy, and I tried to feign reluctance – but you bet I really wanted to. My sister took me into the bathroom and presented me with 3 different bottoms. It was a little weird that she was in there with me, but I tried on the first 2 and they were just a little too big and would surely slip off in the water. But that 3rd one was a Goldilocks moment: it fit just right. I don’t remember those first 2 bottoms, but that 3rd one is etched into my brain. It was a light blue with red cherries all over, and there were ruffles along the top – definitely the most feminine pair. I was as red as a tomato through all this, and my sister could tell I was flustered a bit and laughed a lot. But that was settled and I spent that day swimming in those bottoms. I definitely wished I could have worn the top, but I knew that was an impossibility. Unfortunately, by the next time we went over we had found my swim trunks
Last thing I want to talk about happened when I was 11, and specifically on Halloween. Again, we had gone to my grandparents’ neighborhood as it was more affluent and it showed in our candy hauls. It was a school night, so we started trick or treating earlier than usually, and by the time we got through every house it was still relatively early and plenty of people were knocking on doors. My sister joked to me that we should swap costumes and trick the houses into thinking we’re new kids and get a double haul. We both laughed at it and made a couple of jokes, but as we walked toward our grandparents’ we kind of decided to actually do it. We told our mom and brothers that we were gonna go to my sister’s friend’s house in the neighborhood and swap candy. So in the spare bedroom my sister and I swapped costumes. Mine was homemade: I was going as a skipper from the Jaws ride at the Universal theme park, so it was a sailors cap, blue shirt, name tag, blue jeans, and sneakers. Hers was store bought and was a pretty generic fairy princess. It comprised of the main piece, which was this pink ruffled strapless leotard with a corset and frilly skirt that went down to my knees. She had some tights as well which I put on, and some ballet shoes that were just a hair too tight but I toughed it out and wore them anyways. She offered to give me her bra to help fill out the costume and prevent the top from slipping, but I was hesitant. She put on what little makeup she could on me – some lipstick, blush – and we snuck out the back. We didn’t start till we got around the bend, but we then went house to house and got some more candy. We only did about 70% percent of the neighborhood before we called it a night. We did end up going to my sister’s friend’s house to swap costumes and try to remove my makeup. While her friend and her friend’s mom laughed at our shenanigans, they snapped a picture of us two. I wish I could find it, but it’s been MIA for more than a decade now.
Those are just some of the many memories I have crossdressing and loving it as a kid. I’m 23 now and she’s almost 28, so I definitely don’t get into anymore hijinks with her. There are plenty more stories, and of course my high school years were even more prominent AND public! But those are stories for another day lol. Thank you for indulging me, and I’d love to hear some of your youthful stories! <3
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