Playing Sissy Dress Up with a Brat

I have always been able to talk people, especially men, into doing anything for me. I don’t know why I seem so damn trustworthy to people. But this being the case, it is exactly how I got a guy to play sissy dress up for me.

As a huge practical joker, I love playing jokes on my unsuspecting friends. But I don’t hide this fact. Everyone knows it and yet, more often than not, my friends fall for my jokes. Then they get all mad at themselves because they can’t possibly be upset with me! My friends know I am a joker, so there is no excuse.

I can play jokes on men more easily because I’m pretty and sexy. Men love me dressed sexy. It’s fun because I like how men react when they see me in my skin tight jeans and little tank top. I keep my red hair long and slightly wavy and I’m always in heels. So the guys don’t mind the jokes, because they have the attention of a smokin’ hot babe.  As a result, I can pretty much do whatever I want.

Embarrassing? Perhaps.

I love to find ways to talk my guy friends into doing things to humiliate and embarrass themselves.

I’ve done things like dared one of them to run naked through a department store when it was crowded. How was I to know there was a cop nearby? It was his own damn fault that he got arrested. He was the one stupid enough to take my dare.

I have another friend who is a closet cross dresser. He is one of my best friends. We went out one night last year and got plowed and he confessed that he really loved dressing up in women’s clothing. He went on to say that he wished he had the courage to dress up and go out to a club. I decided, then and there, to assist my friend with his sissy dress up fantasy.

Then he realized that I now knew his biggest secret and he begged me to never tell anyone. He wasn’t gay or anything. I laughed at that comment. He was speaking with slurred speech from drinking so much. He continued, “I just like dressing in women’s clothes.” I told him that I wouldn’t say anything and that we should go shopping for him sometime.

Of course, being the practical joker that I am, I had no intention of keeping such a juicy secret to myself. I just had to think of the perfect time and event to expose my friend. It was going to be classic!

Shopping for the Sissy Girl Dress Up

I made sure that I took him shopping to buy all the right goodies. Shoes, dresses, panties… you name it, we bought it all on that first trip. He must’ve spent thousands of dollars on clothes and shoes that day. That’s not to even mention the tab he racked up at the make-up counter. We told the shop girl that it was all for me, but then I winked at her and pointed to him when he wasn’t looking. She got the message and made sure that all of the shades and things would look good on him.

I went home with him to look at all the things he had bought. He looked so happy to be preening in his new outfits. I told him that I would find a bar that we could go to together in one of the nearby towns so he could wear his new clothes out. He couldn’t pass as a chick, so it had to be somewhere that we knew would accept him and his new pretties.

Getting Exposed

In the weeks that followed, I supported him in every way. I have no problem with cross dressers at all. I just love practical jokes.

During this time, I also planned a party without his knowledge. I invited all our friends and told them it would be held in my basement. What a bratty babe I was being! This way, I could get my friend all dressed up without him ever realizing that there was a whole crowd of people downstairs who would want to see him all dressed up. I even invited his boss!

Party Time!

The day of the party, I told him to come to my house and dress up in his finest girly clothes and put on his make-up. I went on to say that I had set up a photo shoot set in my basement so that he could strut his stuff for the camera all he wanted. He was thrilled.

He took a long time getting ready and all the while I was sneaking people down into my basement. They were patient because I was serving them lots of wine and finger foods. That kept them busy and occupied. No one knew they were waiting for anything.  It was a comfortable get-together. It was soon going to be a sissy dress-up-fest, but they did not know it and I couldn’t wait.

The Sissy Dress Up Reveal by a Brat

Eventually, my friend descended the stairs in his finest duds. He wore a tight little black cocktail dress and heels. Oh, he looked fabulous. I took pictures of him as he walked into the room, completely unaware of the one hundred people watching him. There was dead silence for a moment, and then everyone began to laugh as he screamed and ran back up the stairs. This sissy was completely humiliated. But, we sure had fun at his expense.

We all cherish the picture of him in drag, strutting into the room. Even now, he has the picture framed and hanging on his living room wall. It reminds him of what happens when a sissy has a sweet and helpful girlfriend.

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