Chapters tagged crossdressing

by SissyBoiToi1

Chapter 16

"Let's do a little teacher-student roleplay," Davis says, pulling out a slutty schoolgirl costume. The image on the costume's bag looks like this-- ![](http://lghttp.17106.nexcesscdn.net/808773/magento/media/catalog/product/cache/3/image/9df78eab33525d08d6e5fb8d27136e95/c/o/cost...

by SissyBoiToi1

Chapter 18

You take the feather duster from Davis, and start to dust various pieces of furniture around the room. He stands in the middle of the room, barking orders. "Don't bend your knees! Softer strokes! Show off those panties!" You hear the exasperation in his voice continue to grow....

by SissyBoiToi1

Chapter 23

This is going to suck so hard. But not as much as not wearing this would suck when you get home, you suppose. Looking closer at the contents of the bag, you see a lot of pink. 2 pink blouses, 2 pink pairs of ruffly panties to go over the diaper, and a pink baby bib that says "Hu...

by SissyBoiToi1

Chapter 12

Enough is enough! You're putting your foot down here! Stacy hears your outbursts and looks at you curiously. "But why wouldn't you want to wear these?" "Because I'm a guy! An adult guy!" you yell angrily. "Then why are you wearing this?" Stacy giggles as she surprises you by y...

by SissyBoiToi1

Chapter 12

Muttering angry words about your mother, you pull the clothes off their hangers. You have a pink tutu and a girly blouse. You pull off your pants, pulling the tutu on, the underpants-like leotard squeezing your diaper. You pull the blouse on too, its silky texture rubbing strange...

by SissyBoiToi1

Chapter 12

Muttering angry words about your mother, you pull the clothes off their hangers. You have a pink tutu and a girly blouse. You pull off your pants, pulling the tutu on, the underpants-like leotard squeezing your diaper. You pull the blouse on too, its silky texture rubbing strange...