Have you ever wanted to play dress up? 

Well, this is a story about the time I played dress-up with a little sissy slut! I’ve always loved doing makeovers and playing dress up since I was a little girl and once I got older, I thought all of that was over. I couldn’t have been more wrong, I learned that dress-up and makeovers as an adult are so much more fun! Especially when I turned my eye toward certain targets! 

So, when I was in high school, I had a gay best friend. We hung out all the time, at school, after school, on weekends, you name it. We told each other everything and that’s exactly why I was the first person he came out to. After he told me that, our friendship seemed to grow much closer and we had no judgment between the two of us. I’m still friends with him to this day. So, it wasn’t out of the ordinary for me to practice my make-up skills on him, in fact, he loved it! It got to the point where I didn’t even have to ask him, he would ask me. 

I remember there were some days, he would come over and look through my clothes and ask me to dress up and try stuff on. He especially liked my dresses and skirts. Of course, I wouldn’t turn him down, after all, he was just curious. Little did I know, that was his kinky little fetish! I didn’t find that out until about three years into our friendship.

You wouldn’t believe how I found out! 

It was junior year and we were at school in the library working on a project together. He handed me his phone to look something up for the project and when I pulled up his internet, porn hub was already opened. The video it was on was called “A Pathetic Sissy Boy Plays Dress Up And Gets A Cock In The Ass!”. The video almost started right in the middle of the library! He had no idea that I had just discovered his dirty secret! I didn’t say anything, instead closing the tab and opening a new one. 

I wasn’t sure if that was just a one-time thing or if that was what he was always into. Well, until I looked through his pictures. He had so many pictures of himself dressed up as a slutty woman. I kept lurking and found a picture of him in MY panties! Of course, I knew exactly what to do. I sent the picture to myself and deleted the evidence. 

The next day after school at my place, I confronted him about the video I found and his cheeks got red. He looked so embarrassed and he denied it. He denied it just like I knew he would. So, I showed him the picture of him in my panties. His jaw dropped. 

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