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sissyboy 

gender rebel, hot faggot in a dress, performance art group in portland oregon known for being loud, foul, nasty,artistic, innovative, and above all...extremely sexy.
"are you going to the next sissyboy show?"

"sissyboy is offensive and wrong!"
sissyboy by pillowbookparade May 18, 2005

sissyboy 

sissyboy by Randi Panties September 24, 2003

Sissyboy 

A male who is unattractive and cowardly ; in other words, a beta male
This ugly ass looking guy is such a sissyboy

White sissyboi 

Extremely feminine and passive pink Caucasian boy, who recognizes the unrivaled virility and muscle mass of black men, wears panties and fishnets because he has sissy clit and tiny little balls, worships black people by sitting on black dildos and masturbating to BNWO and pornography interracial
White sissyboi: oh my god, look strong black body with that 9 inch BBC, my pale body with pink 3 inch sissy clit can't stand, hope he use me as his sissy slut!
White sissyboi by WhiteKl August 28, 2023

Sissy boy 

Your local, closested, cuckhold husband who projects his insecurities on to others by spreading lies to feed his egomaniac ways. Wife’s a jealous, cheap, hoe who needs a full-time therapist and hobbies that don’t involve slandering women with real careers.
He’s being such a good Sissy Boy!
Sissy boy by tryanalnexttime October 20, 2022

Sissy boy 

A boy with a small penis who wears a thong and he is locked in a cock cage, he cums in his pants when he sees a picture of Justin bieber
Sissy boy by its the real deal September 21, 2018