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Preparing for my first man
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Okay so I want to tell the story of the first guy I met, he originally posted on a Seattle personals page here, claiming that he could get any man to cum, especially straight guys. Well, as someone who considered themselves straight, but was also insanely hooked on being a sissy, I had to reach out. We chatted for a while, a few weeks probably, about what he would do to me, his kinks, mine, and about me as a sissy. I told him I had never done anything like this before, and he loved that - he said one of his pass times was helping turn straight guys.

Also, i should mention, we decided to change the deal. Instead of him trying to make me cum, I would simply get to experience being a sissy. And he even offered to get me my own cage! It was so sweet, and and on the day the cage arrived, I popped in my plug, got a bag with the cheap schoolgirls uniform I had bought, and got on the bus to his place. Before I left I shaved as best I could, the front was clean and I did my best to shave my ass, but I can't say I had ever done that before! He was so nice though, he even offered to help me shave back there so I was nice and ready for him.

When I get there, I get off the bus, and he buzzes me into his apartment, I was scared and nervous, but committed. I walk up to his room right off the elevator, and I knock. I take a big step back, and not more than 2 seconds pass before he opens the door and welcomes me in. He's very nice, with me being quite shy, and we chat for a few minutes before he asks if I want to rinse off first. He points me to the bathroom, and I walk in as he stands at in the doorway. I realize he has no plans of leaving, so I take off my shirt, then my sweats, and finally my underwear, until I am fully naked with just the plug in. I He smiled, but I wasn't really looking at him too much, I tried to focus on myself as I didn't really even know what to do.

I got in the shower, and started to rinse off. While I did this he walked away, and I was a bit confused until he came back wearing nothing but his boxers. He asked if I was ready to shave, and I said yes. After I turned off the water, he sat on the edge of the tub and turned me around. He took out the plug, bent me over, and got to work. It was really hot, but I felt so small with this other mans hands on me, grabbing my ass and shaving me. I could see his boxers, and his cock starting to get much harder and eventually slip out through the end. It was so hot, end after the shaving was done he told me my cage was on the counter, and that I should put it on along with the short schoolgirl skirt and the white top. He went out to the bed, and told me to come out when I was dressed...

LMK what you guys think, and if you want to hear the next part ;)

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2 months ago