My Sisters Crossdressing Dare.When I was 16 I would go out with my older sister and friend. There is this small convience store near our house. On monday nights this guy my sisters friends knows works there. He's a real nerdy type of guy and sometimes the girls will flirt with him and he doesn't get it. I told her you guys don't approach him right. She said I dare you to try and as a metter of fact I bet you can't get his attention at all. I'll put 50 bucks on it. I told her your on. On monday night I prepared to get dressed and told them they could not see how I was dressed until we got there. I did my hair and makeup, put on a black bra with matching panties. A garter belt with fiishnet stockings, 4 in. heels and then a bright red cami to top it all off. I put on my rain coat and off we went to the store. When I got out of the car I showed them what i was wearing, they scream and laughed. I went into the store, no one was in there I bought a package of gum. As I paid him I opened my coat. His face was frozen. I got my change and handed him a piece of paper with my phone number and said if your interested. I won the dare, but he's still a nerd. He never called.
deleted 26-30 2 Responses 8 Mar 23, 2011