I’ve got a fun sissy boy dress-up story for you all. 

Paul didn’t think he would be a fun sissy boy dress-up story. Instead, he wanted to try and get with me for real. But he was a loser, and I never let a loser near my pussy. 

As Paul begged me for a date, I eyed him as critically as possible. I suggested a forced bisexual sissy situation. Instead of being with me, he could suck the cock of my friend? 

Paul’s headshake revealed that no, he did not want that. So, I offered instead to dress him up at my discretion, and if he wanted me to play with him then, I would. I made it clear this would be a sissy boy dress-up session, and that Paul would be my sissy. He agreed. 

Cleaning Paul Up

Well, to start a sissy boy dress-up session, we needed to get Paul clean. So, I demanded first and foremost that he get into my bath. Unsure of what I meant to do, I explained to Paul that I was going to shave all of him, and clean him up. Though his hands were shaking, Paul agreed to go ahead and get into the water. As soon as he did, I threw in a bath bomb, one with a lavender scent. 

I lathered him up with a raspberry shaving cream and spread it over his legs, his back, and his arms at first. I took my pink Venus razor and began to scrape down his skin, having to pull it several times to get rid of his corse, dark hair. But though it took me about an hour to get Paul ready to start our sissy boy dress-up session, it was worth it. No hair existed anywhere on his body, not on his legs, thighs, or balls. 

In fact, Paul even asked me to do his face, and I took the razor and pressed it against his skin, gliding it up and down. Finally, I saw his pink skin, shaven and clean, pores open and ready for make-up. By this point, Paul smelled of berries and lavender, two very sweet scents.

Doing Paul’s Makeup and Clothes

Nothing is easier to put makeup on than a well-cleaned face. Even though I shaved Paul, I made sure to exfoliate his face. Then, I moved to a concealer that matched his skin tone- something painfully pasty white, as Paul hadn’t ever been outside. Thinking of how I wanted his eyes for our sissy boy dress-up session, I began to draw a cat’s eye marking with eyeliner. For his eyeshadow, I gave him a gradient of purple to white. Since white makes eyes pop, it gave the impression of his eyes being bigger, cuter, and more innocent. 

I thought about what color Paul’s lips should be for our session. Since it matched, I went for purple, to match his dress stockings. I applied blush and eyeshadow quickly and then led Paul to my bedroom. 

Inside, he had a fluffy maid uniform, with headpieces and clip-on drop earrings. He bent over to put on the thong, the purple silk stockings, his cock hard as he did so. I knew a sissy boy dress-up session was perfect for us. 

Trembling, he pulled the dress on over his head, careful not to smudge his makeup. He gave it a twirl and then put on the apron, his earrings, and a cute little headband I found for him. Without any feedback from me, he got onto his knees and said in a girly, breathy voice that he was ready. 

I believed him. He was ready to worship me. 


Would you like to be my sissy? Then call for some hot phone sex

sissy boy dress-up