Humiliation Captions

I’m definitely in big trouble, Mistresses.
I’m definitely in big trouble, Mistresses.
Of course I have heard that saying, babe. I was hoping you were happy with me, but I see why not ...
Of course I have heard that saying, babe. I was ...
This is truly embarrassing. I really do deserve to be a chastity cuckold sissy.
This is truly embarrassing. I really do deserve ...
I’ll pretty much be locked forever, Mistresses.
I’ll pretty much be locked forever, Mistresses.
1
Hot gassy girl blast to the face
Hot gassy girl blast to the face
My micropenis was locked away and replaced with a big toy. I am glad to be made to show it.
My micropenis was locked away and replaced with ...
1
littledickwanker jay YES, Debbie made me try to fuck her with a strap on but it kept sliding off my tiny peepee.
I don’t think there is any doubt, Mistress. I was never really a man.
I don’t think there is any doubt, Mistress. I w ...
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 ...
Sissy Webcam Trainers
Hi-res Realsissies Collection
Hi-res Realsissies Collection
3
avatar
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...
Slave Diana Very cool!!
“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 ...
Penis Ratings
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.
1
Conja Lucky they let you.
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 ...
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 ...
Show your penis to women online
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 ...
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…

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