Humiliation Captions

I’m not sure I like these new rules, Mistress. Can’t we talk about them first, please?
I’m not sure I like these new rules, Mistress. ...
Yes, Mistress. I’ll try not to make too much noise.
Yes, Mistress. I’ll try not to make too much noise.
1
Tinyold4 Yes please mistress may be filled and push against it
They have found out, Mistress. Big time. There is no going back to being a man now, if I ever wa ...
They have found out, Mistress. Big time. There ...
Hi-res Realsissies Collection
Hi-res Realsissies Collection
2
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BarefootSissy Will you please add me to your collection of sissies?
Sissy Anisha / Adil Arman You didnt read the post description above! This was NOT made by me...i merely reposted it fr...
“Please don’t sign up for the Sissy Club subscription, Mistress. It’s too humiliating and not ne ...
“Please don’t sign up for the Sissy Club subscr ...
Apparently, it’s not so harmless after all, Mistress. I will be a sissy from now on.
Apparently, it’s not so harmless after all, Mis ...
It is very frustrating, Mistress. But I agree, I will be a pussyfree loser forever.
It is very frustrating, Mistress. But I agree, ...
2
Show Your Tiny Dick Keep it caged and far away from pussy! lol
Sissy Donna Yes, Mistress.
I am a pure cuckold. All I can do is watch.
I am a pure cuckold. All I can do is watch.
Yes, it is quite obvious, Mistress, that I deserve chastity. No one wants my little dick and I a ...
Yes, it is quite obvious, Mistress, that I dese ...
1
littledickwanker jay i just turned 50 and even though i've tried fucking pussy 3x in my life i failed to penetrat...
Please, that’s not necessary, Mistress. This is so embarrassing.
Please, that’s not necessary, Mistress. This is ...
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You’re absolutely right, Mistress. Any resistance is futile and quickly fades as I’m locked in c ...
You’re absolutely right, Mistress. Any resistan ...
Yes, Mistress, all I get is licking and cleaning up. I am completely weak and submissive. Your p ...
Yes, Mistress, all I get is licking and cleanin ...
The evidence is most certainly quite convincing. Is she wrong?
The evidence is most certainly quite convincing ...
When your cock and balls fit into his cock’s head, you know you’re unqualified for pussy and onl ...
When your cock and balls fit into his cock’s he ...
Penis Ratings
I am as ready as I’ll ever be. I’m so humiliated…
I am as ready as I’ll ever be. I’m so humiliated…
My complete and total emasculation and humiliation, with my clitty preserved in micro chastity a ...
My complete and total emasculation and humiliat ...
I was never meant for pussy. I’m a beta virgin for life.
I was never meant for pussy. I’m a beta virgin ...
Yes, Mistress. I am glad you are at least allowing me to lick your beautiful pussy. My useless c ...
Yes, Mistress. I am glad you are at least allow ...
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My puss is full, Mistress. May I please be released now?
My puss is full, Mistress. May I please be rele ...
Those panties found for me couldn’t be more appropriate. They perfectly complement my small cage ...
Those panties found for me couldn’t be more app ...
Words cannot express my humiliation and emasculation.
Words cannot express my humiliation and emascul ...
I am definitely not a man anymore. I am a cock-loving sissy.
I am definitely not a man anymore. I am a cock- ...
I can’t help leaking, Mistress. I love watching a real man please you like I can’t. I will gladl ...
I can’t help leaking, Mistress. I love watching ...
3
littledickwanker jay I loved watching and wanking while Charles fucked Debbie to ecstatic, moaning orgasms. Howev...
cjack You can lick my cock and cum from my cock and her pussy! If you’re a good boy I may give you...
Sissybuttslutkrystal01 Looks great follow me I’m a sissy cucj
It’s your and my lingerie both making me strain in my tiny cage and drip like a pathetic sissy,  ...
It’s your and my lingerie both making me strain ...
Yes, Mistress, I deserve to be fucked by real men with giant cocks. I hope all that training has ...
Yes, Mistress, I deserve to be fucked by real m ...

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