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You have the ability to go to anytime of your life and live it as a sissygurl. What age to you go to?My sissy staci said she would return to being a high school senior, and join the cheerleading squad.
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Mistress Joy’s School of Bimbo Cock Sucking: All sissy boys must attend!
School Bullies: I’m with the sissy-boi. Bullies don’t deserve the pleasures that my mouth can give them… but that is a seriously nice cock. Decisions decisions.
Sexual Subtext: Enough already! He want’s to fuck your sissy ass and you want him to. Get on with it and quit pussyfooting around. By the way: give that sissy an A for wearing that outfit to class.
Sissy Kids These Days: You give and give, and all you get back is grief.
School Girl Uniforms: Some cliches are worth reenacting.
Graduation Day: Seeing a sissy trying to make her way in such a cruel world always brings a tear to my eye.
Dear Mom, Things aren’t too bad here at the Prestige School for Boys. It was especially fun during our our physical education portion of class. ~your… son, Pete P.S. Send more razors. They have a really strict dress code here. No stubble
Education is Key!
I picture this as the final exam of my sissy school. If you can’t pass then you’ll have to start over and repeat the year. Basically a win/win in any event!
Looks like the Sissy Maid School is about to get a new student!
Are you a boy who’s dying to become a girl?Does the idea of being a feminized, submissive sissy excite you?Do you secretly wish that you could wear panties, high-heels, and makeup?Would you have sex with a man? Letting him use your body however
Sissy Caption - A Different Type of School
Don’t forget that in three days (10-17-2017), I’ll be releasing the sequel to “Dream”. Called “Over the Edge”, it features Naveen Ora, and follows a high school basketball player as he’s unwittingly manipulated into transitioning into
Crossdressed Sissy Caption - School Slut
Could you caption these?Sure“The jocks at school thought they had all gotten pics from one of the cheerleaders so they were all bragging to each other about what a slut she must be and how hard they’d fuck her if they had the chance. Little did they
sissystagg: cutebumsissy: School would’ve been so much funner… 🎀Sissy Captions Daily🎀 ;3
forced-sissy-captions: sissy school
sissyslutcaps: A bit of a longer sissy caption that wouldn’t realistically fit, hope this format is still enjoyable :) In high school you had mostly girl friends, tonight you went to a sleepover and everyone gave each other makeovers, they insisted
cassiestarxx:old-school sissy caption hehe ♥ ask me anything… ♥
Sissy School Faggot