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Sissy Charlotte

Users

0

Media

2

Created

09/21/2025

I kept my wife's Halloween outfit but she doesn't know

r/StraightToSissy

u/littlesisterboy 2 weeks ago

21

I kept my wife's Halloween outfit but she doesn't know

My older brothers friends used to beg me to wear panties when they would have sleepovers. I think this was their ultimate goal 🏆

r/SissificationProject

u/littlesisterboy 1 week ago

3

My older brothers friends used to beg me to wear panties when they would have sleepovers. I think this was their ultimate goal 🏆

I looked at sissy porn a few years ago and now look what it did to me 🤦‍♀️

r/LimpClittySissy

u/littlesisterboy 1 month ago

17

I looked at sissy porn a few years ago and now look what it did to me 🤦‍♀️

Why does it turn me on so much to show people how small it is 🤷‍♀️

r/smalldickpositivity

u/littlesisterboy 3 months ago

119

Why does it turn me on so much to show people how small it is 🤷‍♀️

My wife is gonna kill me if she catches me in her nightie and stockings...with a wig on playing sissy dress up for strangers on the internet 🤦‍♀️

r/LimpClittySissy

u/littlesisterboy 6 days ago

11

My wife is gonna kill me if she catches me in her nightie and stockings...with a wig on playing sissy dress up for strangers on the internet 🤦‍♀️

My older brothers friend used to bring his sisters clothes to our house and sneak them to me and get me to play dress up for him. I loved it 🍭 🧁 🤦‍♀️

r/CrossDresser_Closet

u/littlesisterboy 1 week ago

386

My older brothers friend used to bring his sisters clothes to our house and sneak them to me and get me to play dress up for him. I loved it 🍭 🧁 🤦‍♀️

I clicked on a sissy link one time just to laugh at how pathetic a man could become and now I'm literally becoming one🤦‍♀️

r/SissyHeaven

u/littlesisterboy 1 week ago

54

I clicked on a sissy link one time just to laugh at how pathetic a man could become and now I'm literally becoming one🤦‍♀️

My older brothers friend used to bring his sisters clothes to our house and sneak them to me and get me to play dress up for him. I loved it 🍭 🧁 🤦‍♀️

r/FemboyBussy

u/littlesisterboy 1 week ago

6

My older brothers friend used to bring his sisters clothes to our house and sneak them to me and get me to play dress up for him. I loved it 🍭 🧁 🤦‍♀️

My older brothers friend used to bring his sisters clothes to our house and sneak them to me and get me to play dress up for him. I loved it 🍭 🧁 🤦‍♀️

r/ExposeSissies

u/littlesisterboy 1 week ago

28

My older brothers friend used to bring his sisters clothes to our house and sneak them to me and get me to play dress up for him. I loved it 🍭 🧁 🤦‍♀️