Sissy Tiffany The Crying Fuckhole

I am sissy Tiffany Chastity Destiny the crying fuckhole. A 53 year old slut from Copenhagen, Denmark 🇩🇰 I live with my wife / Madame and she holds the keys to the chastity tube and the collar . I am not interested in any kind of financial domination or tributes.

[sirowner]

Only intense training can bring you to perfection, gurls and bois

[subboi-41]

Lovely. Please make sure to make escape impossible, Sir.

[master-roughx]

If you reblog or interact with this post then you are giving me your consent to send you degrading messages, to turn you into a little cockslut, send you pictures of cock, messages about what I want my friends and I to do to your body and make you fully submit to anything and everything I ask. You’ll be a whore with no control and no brain, just a dumb bimbo for cock.

[subboi-41]

Thank you Daddy.

[mystepmomspanksme]

Motivation

fetchthestrap-deactivated202405

“You’re going to eat me out and if you don’t do a really, really… REALLY good job I’m going to belt whip your bare bottom over this desk. Then we’ll see if your technique improves.”

[subboi-41]

Thank you Madame.

[curiousbarbara]

Don't cry. This is a good lesson for you. Go to the corner. Don't put your pants on. And remember, from now on, I will not hesitate to use this hairbrush every time you disobey me, even in the slightest way. Until your behavior is impeccable. Understood?

[mystepmomspanksme]

[charliechastity]

Here are 3 things that matter to me: 1) That you can see my thick cock entering you. It's why I like to pile-drive it into you. 2) Whether spurting in a cage or given a rare stroking when I milk every drop, you drink every drop, whore. Every fucking drop. 3) Begging for chastity. If cage-ruined, you beg to stay in. If I milked it myself, you beg for immediate re-locking. I want to watch you beg hard, with your own cum still glistening on your lips.

[subboi-41]

Thank you Madame.

[subboi-41]

I totally forgot about this, until it got reblogged. Probably one of the best captions I’ve seen on here.

[forciblyfeminised]

There you'll meet lots of new friends dressed like that, sissy!

[sissypredator]

I'm your new friend sissy! And youre about to discover how it feels to be treated like a helpless little sissy slut as my massive alpha cock pumps cum up your cute little sissy ass.

[subboi-41]

Thank you Madame.

[richelletgirl]

[prettycrossdressing]

Agreed!

[sissypredator]

I love coy little sissies who think they look cute and innocent. I’ll quickly drive that coyness and innocence out of you as I force you to bend over and drive my hard cock up inside you, ramming it in and out as you beg for mercy. I’ll leave you in a crumpled heap of torn clothing on the floor, like the snivelling little faggot that you really are. Not so innocent now, are you?

[subboi-41]

No Master. Not innocent anymore.

[hipueppchen]

I got caught by my strict Auntie, having "Fun" in Her Stocking-Drawer.

Now i have to face the consequences ...

Auntie is so cruel, but I ♥️ Her so much that I will do anything She orders...

... the more humiliating and embarrassing, the more my shrunken weenie is trying to get hard in its cage...

I ❤️ to be Aunties Sissyboi

[subboi-41]

Thank you Auntie.

[sissycdkari]

[subboi-41]

Pink !!!!

[mommymiassissygirl]

@mommymia56 says these are the start of our week long session. Baby girl doesn’t know whether to be excited or terrified! What do you think?

[subboi-41]

Pink !!!!

[yesantoniopezzinius]

[subboi-41]

Miss Piglet is so beautiful !

[femdomvignettes]

It was meant to be a weekend getaway, a chance to escape the city, but now Alice found herself in a real predicament. The thick metal holding her in place forced her to squat, gagged, like some medieval torture device. She had pulled at it but there was no give, and the panic was beginning to set in.

A heavyset woman in her 50s walked into the room, her buxom curves held into a leather corset and matching leather pants. She walked across to Alice with purpose.

"I've made a few calls, and good news, we've found a buyer for you." The woman seemed delighted, bending over to stroke Alice's hair gently.

"You are making me a lovely bonus darling, you should be happy you won't be kept here too long with me, I'm not a very nice person."

Alice whimpered as the woman grabbed her hair roughly. "Such a shame I won't be the one who breaks you in. But we can have a little fun for a couple of days can't we? See how eager those holes are to be used yes?"

The woman roughly tore away Alice's underwear, as she sobbed the woman's fingers roamed and explored her freely.

"Already wet for me? Oh my, this will be fun" the woman giggled as she began to tease and torment Alice.

[2ksissybreaker]

🏃‍♂️‍➡️🚶‍♂️‍➡️🧎‍♂️‍➡️🧎‍♀️‍➡️

[subboi-41]

I would love to be Alice.

[sadidisticsir]

[2ksissybreaker]

🏃‍♂️‍➡️🚶‍♂️‍➡️🧎‍♂️‍➡️🧎‍♀️‍➡️

[subboi-41]

Please keep me like this, Master.

[stevealero]

[2ksissybreaker]

Things like you don't need freedom.

🏃‍♂️‍➡️🚶‍♂️‍➡️🧎‍♂️‍➡️🧎‍♀️‍➡️

[subboi-41]

Thank you Master.

[doggers05]

How to gag a nagging woman, by Elijah Pink.

[2ksissybreaker]

🏃‍♂️‍➡️🚶‍♂️‍➡️🧎‍♂️‍➡️🧎‍♀️‍➡️

[subboi-41]

A gagging to die for !

[mummymacyrose]

Respost, sissy boys

[subboi-41]

I surely would love that, Madame.

[mummymacyrose]

[subboi-41]

Pink !!!!