Went to the city, and had fun too :)

Let's just get this out of the way. I am a 27 year old man, and I dress as a woman in public. I haven't been very comfortable leaving my hometown, but this story is different. Living with my mom at the time, I would wear her dresses into public places. One night, I decided I would challenge myself. I WALKED 6 miles, or about 9.5 km, to the nearest big city. I did this in high heels, and a dress, along with the other women garments. After this long journey, my legs were killing me, so I decided to stay the night at a hotel in the city. As I walked to my hotel room, this man walked by me. He greeted me, and invited me to his room. I accepted his invitation and entered. He told me to go sit in the bedroom. I did as he asked, and when he came back, he told me he knew about my secret. "It's ok," he said, "I won't tell, but only if you can do my request." His request was to give him a nice b******. I wasn't gay, I just dressed feminine for fun, but as I sucked his fairly giant c***, it felt good. I was enjoying myself.

The next day I checked out of the hotel. I had the man's phone number now. I will never forget that night.

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  • The closest I came to this was years ago I was driving down the road and see this curvy well dressed black girl walking down the road. I stopped and offered her a ride which she accepted. As she gave me directions she was thanking me for the ride and how nice I was. She had told me I could drop her off at the end of her road not wanting to make me go out of my way but I told her it was OK. Once we got to where she lived she had me stop about half way up the gravel road to her house.

    She reached over and started to rub my thigh and my c*** started to get hard as I'd kind of wondered what it would be like to be with a black girl. In no time I was getting one of the best blow jobs ever. I reached down and started to fondle one of her big t*** but it felt like a foam pillow. I began to look closer and soon realized I had a black guy in drag sucking my d*** for me. And it was pretty damn good. He sucked and licked my b**** and when I shot off he swallowed every drop. By now his wig had came off so there was no pretending any more. As he got out of the car he told me his mom worked 2nd shift and if I ever wanted him to suck my d*** to come by any weeknight.

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