One Great Halloween

I was 18 and I was alone at home for the last week of October and the first week of November. I had dressed up in women's clothes before, just sitting around the house with nothing else to do. So when my friend George called me Halloween day to invite me to a Halloween party, I said id go with him since I had nothing else to do that day. I sat around all day thinking of what to go as, nothing came to mind.

He showed up to my house at around 6p.m. dressed as a doctor. He looked very convincing and I playfully told him I needed a prostate exam. We both laughed as he took out a rubber glove and placed it on his right hand. He looked at me and told me to drop my pants and bend over. I thought he was messing with me so I just looked at him and laughed, he looked me dead in the eyes and said I'm not messing around I want you to bend over. I got a little scared and began to sweat a little, he burst out laughing and saying he was just teasing.

I asked him what I should dress up as for the party, he had no idea what to suggest and we both sat thinking about a costume. Suddenly he asked me if I still had the women's clothes I would wear around my house. I told him I had thought about it but needed a thong to go with it because I had no panties. He took off and told me to get ready in my costume while he was back. I took a shower and shaved all over. When I got out I put on my black skin tight mini skirt, black tube top with a strapless bra with prosthetic breasts, my black wig and did my make up.

Shortly after George came back looked at me all over and said I looked hot. I blushed. He handed me a red thong, then took it from me and asked is he could put it on me. I agreed to this and when he put it on me I bent over with my ass in his face and told him I was ready for my prostate exam. He lifted my skirt, pulled my thong to the side and began to lick my asshole. I shivered all over. He slowly began to finger my ass and caressing my cheeks. Suddenly he got up and dropped his pants. I asked him to take one of the lubricated condoms from the entertainment center. He took one opened it and placed it on his hard cock. He placed the tip of his head directly on my ass hole; he pushed it in till his whole head was in me.