SissyBoy NSFW GIFs and Nudes - Popular Posts

Media

88

Created

09/12/2024

I love to feminize boys into sissies.

u/rhileyhiles Clariceboaventura SissyBoy 8 months ago

881

Your roommates caught you in your girl clothes. You forgot your sissy body turns boys gay, but it was too late.

r/SissyCaptionStories

u/Seek8888 Longjumping Alps 850 SissyBoy 6 months ago

547

Just one week will turn any boy into a leaky pathetic sissy.

r/SissyChastity

u/zsirblade Ssirblade SissyBoy 11 months ago

614

I failed as a boy,but I am happy being sissy 💕

r/asiansissification

u/yellowmevious SissyBoy 1 year ago

16

Caged and pretty before he gets dressed for another ✨big boy✨ day at work… he’ll be the sluttiest sissy in the office 💅🔐

r/ChastityCouples

u/KinkDifferently SissyBoy 1 year ago

973

Caged and pretty before he gets dressed for another ✨big boy✨ day at work… he’ll be the sluttiest sissy in the office 💅🔐

Totally failed as a boy! Hopefully im making progress as a sissy?

r/StraightToSissy

u/sissyjini SissyBoy 10 months ago

962

Totally failed as a boy! Hopefully im making progress as a sissy?

Being a boy hasn't worked out so well for you, don't you think you'll be better off as my sissy fuck doll?

u/Jadesjungles SissyBoy 1 year ago

1812

Being a boy hasn't worked out so well for you, don't you think you'll be better off as my sissy fuck doll?

My gf found my sissy clothes. I’ve been locked in chastity and forced to stay feminized since. She said she wont let me be a boy anymore.

r/ForcedFeminization

u/Artistic_Weight1834 SissyBoy 6 months ago

1558

My gf found my sissy clothes. I’ve been locked in chastity and forced to stay feminized since. She said she wont let me be a boy anymore.

This str8 boy needs pulled deeper into sissy hypno

u/Dizzy_Butterscotch28 Lemming00 SissyBoy 1 year ago

1366