So, for me it started when I was around 12, maybe even 11. It was the summer before my 6th grade year I think. Me and two buddies were playing in the woods and one of them told us that he liked to wear his sisters panties. He said that it felt good, and something about how if he pulled them down just a little so you could see some pubic hair at the top thought it looked like a girl. Girls weren’t really shaving down there as much back then I guess, lol.
Anyway, it was an out of the blue disclosure and pretty surprising. None of us had ever talked about anything like that before and he was actually one of the tough kids at school so it was doubly surprising. He did threaten to beat us up if we ever said anything to anyone 🙂 We never talked about it again, but I always wondered what happened to him or if he ended dressing fully too. Also wondered if our other friend ever tried it.
I of course did try it. I was curious after he said that, and not long after I borrowed a pair of my sisters nylon panties from the wash and ducked into the downstairs bathroom to try them. I had honestly never looked at her stuff before and never thought twice about. I still remember they were a seafoam green bikini with some lace accent. They looked so unlike my tighty whities and the material felt so good. I slid them on and it was euphoric. They felt amazing.
So, my sister was 4 years older than me, so her stuff fit me pretty well at that point. I remember thinking that of panties felt so amazing, what was it like to wear other girls clothes? It didn’t take me long to find out. My dad worked evening shift, and my mom was a nurse who worked shifts. My brother was in college at this point I think and my sister was pretty busy and would end up going to college 2 years later. I had a lot of time to myself as a kid to dress, and I did.
I pretty quickly moved to adding bras to the panties, which were also amazing, I remember we had a stack of clothes that were going to be donated in the laundry room and there were two of my sisters sun dresses in that pile. Those were the first actual girls clothes I wore and I wore them a lot before they did finally get donated. After they were gone, I started looking in her closet for stuff to wear. I remember being scared and excited going through her stuff. The laundry room and donate pile somehow seemed okay, her room was a magical world of girls stuff. I know in hindsight that its a violation of a persons privacy to go through and wear their stuff, but as a kid its what I had access too, and honestly probably some of the forbidden aspect of it made it more exciting. In her room I discovered pantyhose and slips, which were also adorable. She had nice clothes too. I learned to be excited at Homecoming and Prom time because I knew she’d get some amazing dresses that I’d get to try later. She had great taste in clothes. I like to think that rubbed off on me 🙂
At some point I started wearing my mom’s stuff too. She didn’t have much in the way of dresses, although I did try what she had, she was more a dress slacks kind of lady. At this point I wasn’t interested in girls/women’s casual looks, it was all dresses and skirts for me. She did have some nice bras, panties and slips though. Not slutty stuff, but kind of classy and feminine. She was a nurse too and actually had two nursing dresses from back when nurses actually wore white uniforms. Even as a teen it was super fun to dress up as a nurse with white pantyhose on 🙂 Again, not cool to wear your mom’s stuff although I later found out that was common. At the time though I had access to both a teen girl’s wardrobe and an adult woman’s so it was an exciting time and it definitely formed my views on style and clothing. I think that may be why I prefer real women’s fashions, rather than fetish stuff that a lot of CD’s like.