First Time Wearing My Sister's ClothesCompared to some of the other stories here, this is pretty uninteresting, but I'm sharing it nonetheless.
Summer is winding down, and my sister just went off to college. Thankfully, she left a decent amount of clothes behind at the house. I am 15 at the time. I've always wanted to try cross dressing. It seemed like it would be great, and I'm already kind of girly so I wanted to try looking the part. My parents were at work and the house was empty this day. I remembered my sister's clothes, and I snuck my way into her room. Even though the house was empty, I still felt very nervous and cautious. I looked in her drawers and found panties, bras, jeans, shirts, and everything I could want. So I undid my pants and underwear and sought to replace them with female clothing.
First I went through her underwear drawer. I felt like such a pervert for doing this, looking through and trying on her panties, but I wanted to, and nobody was around. I took a pair of nice, cute looking panties and slowly slid them up my legs. In the past I had read many people's experiences cross dressing, and they had said panties just felt so good. I can definitely attest to that. They obviously aren't made for men, though. My sister was also a bit smaller than I was, so it all felt a bit tight. It didn't help that I was getting an erection, either. But I tried to ignore it, and I just stood there, looking in the mirror above my sister's dresser. I was wearing panties. They were tight, but comfortable. My butt was hanging out a little bit, but it wasn't annoying. They were just blissful. It felt bad because I shouldn't be wearing my sister's panties, but it felt good because it was just plain wonderful. The only annoyance was the bulge in the front. That was annoying. But I pulled my shirt down, and it became invisible, and I felt kind of like a girl. I certainly didn't look like a girl, though. So I took a pair of tight athletic pants (I think... I don't really know much about girls' clothing) and slipped them on. They were tight, but extremely comfortable. I looked only at my legs in the mirror, and they looked like girls' legs. I looked up. Boy. So I delved into another drawer.
I found a cute shirt and tried that on. Again, my sister was smaller than me, so it was tight, but it formed my body a bit. I even took on a bit of a girlish form. I was just so happy. I smiled and looked. I didn't even really think about trying on a bra. It just didn't seem like it would work. So I just used what I chose. I tried on another shirt, then went back to try some other panties. I was in heaven. I started getting paranoid about when my mom would get home, though, so I changed back into my clothes and put everything back as it was. On the way out, though, I checked her closet. There were dresses and shirts and wonderful things. I was done for the day, but maybe on my next trip back, I'll do more and try more and actually try to fit the part. Sounds exciting. :)
I just wish I had a wig. My boyish short hair just doesn't fit with the female body I'm trying to make. I'll try doing some things to it, though. In all, my first experience cross dressing was wonderful. I was really paranoid about being caught, but otherwise, pure bliss. If you read this whole thing, thanks. :)