I’d better start off with my childhood, which was pretty good! There wasn’t anything out of the ordinary. I mean, practically every little boy has dressed up in some girl’s clothing. It’s really just normal curiosity. I tried on my mom’s one-piece swimsuit when I was around six or seven and tried on a couple of other swimsuits around that same time, too.
When I was seven, I was hoping for a sibling to have fun with. My mom gave birth to a little girl. Her name was to be Danielle; sadly, an hour after birth, she died. She was premature; something I also was, but I survived. I didn’t know it then, but that event would have a serious impact on my crossdressing life, and my life in general.
It was when I was twelve that my sister’s death really hit me. I had been wearing some clothing that I snuck from my mom now and then, but now I was wearing it nearly every night in bed. It seemed to give me a form of comfort, and lying there in bed, dressed in girl’s clothes, I prayed to God to bring my sister back. I cried for endless hours, and I slowly sank into depression as I made it halfway through being 13.
Then when I was 14, I came up with a brilliant idea! I could be my own sister! I started wearing girl’s clothes every night for a different reason. In my mind, it was to remember my sister and what she would have become. And I started to experience new types of girl’s clothing other that the swimsuits I’d been wearing. I tried on panties, exercise bras, shorts, pantyhose, and of course regular bras and stuff like that.
I remember during this time, I wore a blue bikini top with matching bottoms underneath my regular swimsuit to the lake. We had (and still do have) a boat. A note of caution to any crossdresser who’s just starting out; if you’re reading this, please pay attention, NEVER wear a girl’s swimsuit underneath your regular one. You’ve gotta be really good to pull it off! Bikini bottoms you can definitely do but the top is really hard. I tried any excuse I could come up with to stay out of the water. Somehow, it worked.
At night I would dress up in girl’s clothing and pretend I was my sister. I referred to myself with her name, and I took on a girly personality. It was around age 17 that I changed my reason for crossdressing. Not entirely, but I did change it a little bit. I still do it to remember my sister, but I also do it because I know that deep inside, I’m a girl. I love the way girl’s clothes feel, and I love being this special kind of girl.
I was walking around the church that I attend with one of my best friends. He knows that I crossdress. He asked me if I liked panties and if so, what kind? I said that I liked all of them except thongs; I don’t like the way they feel, besides, my thingy won’t fit inside them anyway. He said that he’d give me a pair of pink panties if I’d go into the girl’s bathroom and do my business without getting caught. Of course I said sure!! I didn’t get caught and he gladly gave me a pair of panties that he stole from his sister.
That was like a drug for me. Once you start, you can’t stop. I asked him later if he’d start sneaking me panties and telling him how much it meant to me and how hard it was for me to get something like that. Thank goodness he’s nice enough to do that for me. To this day, he still does a panty raid of his sister’s drawers for me and sneaks them to me. He’s a really nice guy. I just recently got from him three pairs. One was totally black with black lace around the top. Another one was red with pink hearts around it. And the last one was green with white polka dots and green lace around the top. I love those and wear them a lot!
That’s really the end of my story. For those just starting out, be who you know you are. If I didn’t believe that I was a girl, I never would have carried on. The people here are really friendly and I’m sure you’ll have a fun time crossdressing! I sure do. Even if I still do it in secret.
Love you all! -Amber