While working on the streets I get a lot of out of the ordinary sexual requests. One of my favorite ones that I have had so far involved Cuckold sex. This guy wanted me to play the role of his wife so he could be cuckolded. When I looked in the car I expected to see another guy in there, but it was only him. I asked him where we were going to get the other guy, he said he would take care of that, but he wouldn’t be able to do it until the next night and asked me if I would accept a retainer. Like I’m a fucking lawyer. I told him that I would be at the Hotel on time the next night. He told me he would give me the rest of the money when I showed up. Then he gave me a picture of his wife, and some of her lingerie.
I showed up at the appointed time and was met by the man and another guy. He told us that he has always wanted his wife to cuckold him, but she has gotten to the point to where she finally said that she wouldn’t do it and for him to stop asking, but he had her permission to pay someone to role play it for him as long as he didn’t fuck the woman. Fair enough!
He really played it up. He gave me a very nice black dress to wear, then we went out for dinner, then came back to the Hotel. Where I informed him that his cock just wasn’t going to work for me anymore, as it wasn’t adequate, but I had someone that I wanted him to meet. We opened the Hotel room and there was the other guy, naked, stroking his cock. The guy that was playing my husband started to act upset, so I did my part. The whole thing was super surreal because my “date” was 100% into the whole role play.
I did add another thing to it. After my fellow actor finished fucking me, I had the distraught husband clean off the guy’s cock. He wasn’t expecting that, but in the end he paid me double than the price previously agreed upon. He told me that he wants to do this once a month. I am all for it!
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