Sissy Captions, Sissification Caption Pics

Teri the tiny pecker packing panty wearing cuckold fairy

This is Teri. He’s a tiny pecker packing, panty wearing, sissy cuckold that has premature ejaculation issues. That’s right, he has a micro penis and can’t hold his load. That’s …

Come Haze This Sissy Pledge

Come haze this sissy pledge and follow her journey through sorority, frat boys and lots of cock shoved in her mouth! Weekly it’s a new adventure! Follow on IG @andreadre026

Cynthia shows off her curves and remains pussy free

Cynthia is feeling so feminine and seeks alpha attention. So far in 2023 Sissy Cynthia has had a over 10 hot girls tell him to be pussy free for life. …

Ocean City Hooters Girl Denver Shoemaker

Local residents of Ocean City, MD, know all about darling Denver Shoemaker from neighboring Ocean Pines. He’s the crossdressing waitress that loves to tell the world about her cravings for …

For some sissies it all started like this

For plenty of sissy boys out there in the world, it all started with something like this. A pretty bra with some balloons inside sure does bring the sissy fantasies …