r/Sissy_humiliation • • 13m ago

how many times would u fuck a tgirl in a day NSFW

• Upvotes

r/Sissy_humiliation • • 21m ago

humiliate me as a toilet NSFW

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r/Sissy_humiliation • • 40m ago

Am I even a boy anymore NSFW

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r/Sissy_humiliation • • 55m ago

Would you like to be sissified in my crib like this? NSFW

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r/Sissy_humiliation • • 1h ago

R u gonna humiliate me (last page) NSFW

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r/Sissy_humiliation • • 1h ago

Would you let your pretty domme feminize and degrade you? NSFW

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r/Sissy_humiliation • • 1h ago

cute little skirt, useless caged cock 🔐 NSFW

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r/Sissy_humiliation • • 1h ago

will u make me ur sucking buddy NSFW

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r/Sissy_humiliation • • 1h ago

Sissy’s first wig NSFW

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r/Sissy_humiliation • • 1h ago

My girlfriend turned me into her slut NSFW

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r/Sissy_humiliation • • 1h ago

I’m begging to be bullied for being a cock slut NSFW

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r/Sissy_humiliation • • 1h ago

You’ll have your work cut out for you with my cock today NSFW

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r/Sissy_humiliation • • 2h ago

You bitch, get down on your knees and show me what you’ve got NSFW

4 Upvotes

r/Sissy_humiliation • • 2h ago

Please turn me into a bimbo barbie NSFW

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3 Upvotes

r/Sissy_humiliation • • 2h ago

Come twerk on mommy lap NSFW

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2 Upvotes

r/Sissy_humiliation • • 2h ago

Would you let me feminize you until you want huge cocks in your ass just like me? NSFW

60 Upvotes

r/Sissy_humiliation • • 2h ago

How long can you last? NSFW

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2 Upvotes

r/Sissy_humiliation • • 3h ago

Stupid sectet sissy bitch risking viral exposure kik bambilovescox im so dumb for this its really my biggest secret NSFW

5 Upvotes

r/Sissy_humiliation • • 3h ago

Calling All Good Subs – Let Me Give You What You Deserve NSFW

2 Upvotes

r/Sissy_humiliation • • 3h ago

would u suck my cock if i invited u over NSFW

10 Upvotes

r/Sissy_humiliation • • 3h ago

Maybe I'll remember where I put the key if you cum like a sissy for me 💋 NSFW

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3 Upvotes

r/Sissy_humiliation • • 4h ago

Losing to big black cock >w< NSFW

10 Upvotes

r/Sissy_humiliation • • 4h ago

Sissy liking for daddy for humiliation and use NSFW

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2 Upvotes

r/Sissy_humiliation • • 5h ago

New video cummin on the 17th! NSFW

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1 Upvotes

r/Sissy_humiliation • • 5h ago

What was like the Sissy Maid world/contetn before Mrs. Silk? NSFW

3 Upvotes

Hi, I am really curious about what was like the sissy world (content) in the early 90s before Mrs. Silk web page? Where did people get the videos, dresses and stories about being transformed into a submissive sissy girl?  Was Maid Jane the first “proper sissy maid”?

I read somewhere that Prissy Sissies existed in the 60s and i have seen a 1971 Dutch movie called “Business is Business” where a dominatrix has a sissy maid slave and the sissy gets spanked by her. Apart from that I have not found anything else.

Could anybody tell me more about it?

Business is Business (1971)

Prissy Sissies