A Dare

I had taken a dare for $200 to dress up in my brother's girlfriends clothes and go about my day like normal. I planned to just stay inside the whole day but noticed that we were out of water. Fuck! I think. I need to go get more water and I just have to be dressed like this. I know that I look like quite a convincing girl. When I had first tried on the top I figured it would be a bit tight and it was, but not overly tight. I also had to wear her panties which felt a bit strange going in between my cheeks. When I grabbed the jeans though, I thought there would be no way I would fit in them, but I did. I actually filled them out quite nicely too. My brother thought so as well. When I told him I had to go get water he laughed and said he would be joining me. I sigh thinking he is just going to tease me the entire time as we go to our nearby water filling station to fill up the jug we had brought. I had to bend over at one point as I had dropped the jug of water and I hear a bit of laughing from my brother. "What?" I ask as I look over my shoulder. "Oh nothing, it's just that your ass looks even better than my girlfriend's when you are bending over like that." I feel my face getting red. "Shutup, I do not." He takes a quick picture and shows me and damnit he was right. "See I told you." I just hit him on the shoulder as we head back with the water. I didn't know it, but that was the beginning of me dressing in girl clothes more often and loving how I looked in them. My brother enjoys the company when I do it too. ;)