Hailey and I were hanging out the other day and were looking to get into some mischief. We decided to call up our little sissy boy for some good ole humor. Nothing quite like humiliating a good little cock sucking pussy boy.
In hopes that we could drum up the perfect little toy to embarrass, we started going through our contact list for the perfect little closet freak. Finding the right one we sent him a text. “Come over so I can dress you up and parade you around” with an address to a cute little women’s clothing store. We got in our car and headed down to the store to wait.
About 20 minutes later he showed up looking quite abashed, this is going to be perfect! We walked over to his car and put him into the backseat. Getting in on either side of him Hailey pulled out her makeup bag and started to giggle. As she started putting makeup on him I grabbed his hands and started applying red press-on nails to match the red lipstick she brought with her. Once his cat eyeliner, long wig, and mascara were applied it was time to take our plan to the next level. Humiliating this little closet faggot was going to be so much fun.
Dragging his ashamed sissy self into the store between us it was time to really embarrass him.
Instructing him to walk to the girl behind the counter and ask where he can find the sluttest dress they carried. Hailey could just not stop laughing at him. She has the cutest little giggle. Red-faced through his makeup he walked over to the girl who finally looked up. She could not keep a straight face. Stumbling in embarrassment he could not manage the words, as a result, Hailey started laughing so hard that tears rolled down her face. “Do it or we will make this so much worse for you” I said.
Flustered as he asked the worker for the sluttest dress she had. She was laughing so hard that all she could do is point in the direction.
Making our way to the dresses with him leading the way all the girls stopped to watch us. Picking out 3 dresses in his size for him to try on. One short pink off the shoulder dress one tight black dress with the back out and a slinky long red strapless dress. Next, we made our way over to the bra and panty section so that he can be fully decked out in sissy gear. Grabbing a padded red bra and matching thongs to go underneath the dresses. We then made our way to the dressing room.
Getting all the ladies together for our fashion show while he changed, instructing half of them to laugh and half to praise him. As he walked out and saw his audience of about 15 women he turned beet red. Hailey leading the woman in laughing and catcalling him a sissy boy. While I instructed him to turn around and give us a show, the other half ooohed and awwed. Humiliating him further.
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