It All Started at Halloween
My wife's sister hosts a costume party every Halloween, and the theme this year was superheroes and their girlfriends. My wife suggested we go as Superman and Lois Lane. I agreed, thinking I would be a great Superman. She corrected me and said she will be Superman and I will be Lois Lane. I objected, but lost. She said we could win if I was convincing as a woman. She got me a dress and heels and a wig. As I slipped on the panties and stockings, I got excited! By the time I was fully dressed, I was so excited, I thought I would burst. She suggested I wear the panties, heels, and stockings each night around the house so I could get good at walking in them. After a few days, I was used to them and could walk just like a girl. They were so comfortable, I forgot I was wearing them when her friend came to visit. Her eyes got real big when I answered the door. Suddenly, I realized what I was wearing and turned red in embarrassment. She smiled and said I had sexy legs. My wife had invited her over to help with my makeup. I had to shower and shave most of my body. Then they got busy and, before I knew it, I was beautiful! We went to the party and no one knew I was a guy. I even had some guys dance with me. We won the first prize, but more importantly, my wife now let's me dress as a woman for some role reversal sex!
— Alec, 28