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I’m required to always be over the top thankful when responding to any new homework assignments given to me by Miss Madison or Princess Christina. My owners monitored my email responses. The frustrating thing for me was I did thank her twice and

Pic of Miss Madison holding onto my chastity key over summer break when she was back home living in the same city as me. You can see she is wearing her sorority shirt. Princess Christina talking about using losers and loving it! Of course what Princess

chien-de-nadya: Chastity Cum-Job Princess Rikki has decided on the ultimate form of male control, keeping her slaves cock locked away in permanent chastity. After a few weeks of chastity his cock has become embarrassingly sensitive, his balls are ready

princess-bobbi-gurl: Anybody wanna help a gurl get her diapys on?

*whimpers* day 4 of being in chastity and all shaven clean. and my Miss keyholder lives 5 hours away! *gasp* Sissyrachelle1983@yahoo.com

Oh my!!! After 5 days in my pretty pink princess chastity belt I feel so femmy and subby!! I want to be kept in my frilly dresses, locked in lace as a sissy maid forever! I would so love to be someone’s full time!!! Sissy Rachie looking like she’s

Safety secured in my pink princess belt again with miss holding the keys!! Day 1 again! *mind lost in pink wavesEven the chastity is princess pink! hehehe

Princess now realizes just what you sissies and male subs need to help with your training. Bring me your dick for a minute, I have something to wrap around it… Sounds hot doesn’t it.

Chastity is turning this sissy into a nympho slut! That’s just what Princess likes to see.

Still tough for me to go a long time in chastity, but this is me before work!Keep it up sissy! Princess wants that clitty cock perma-locked!

Love the blog!Thanks gurl! You’re well on your way to becoming a sissy for sure, especially how you fit that tiny chastised dick in your panties so well. That’s what Princess likes to see.

femdom-brats-and-princesses: Mikayla’s got a Special Offer for her cuckolds and wimps. “ You can either cum EVERY day for a whole year or you can spend the next 12 months locked in your steel chastity device ….”Sounds to good to be true?….of

It sure does princess.

chien-de-nadya: Chastity Cum-Job Princess Rikki has decided on the ultimate form of male control, keeping her slaves cock locked away in permanent chastity. After a few weeks of chastity his cock has become embarrassingly sensitive, his balls are ready

bmwoly: robcuckoz: robcuckoz: when it arrived I panicked and thought I must have messed up the measurements. It’s a snug fit but it’s right. Given its so short and the angle it’s only sit down pee. I saw a thing on barefoot princess where she

princess-hannah18: It belongs to me. If you want to stroke you’ll need to pay

A character from a lesser known, but quite cute manga/anime about a female nerd and her friendship with a cross-dresser: Kuragehime (海月姫), the Jellyfish Princess.

I think this is my first, but not last caption featuring Snow White. For some reason, she seems to be more suited for kinky reinterpretations than other fairy tale princesses. It helps that the clothing of her Disney version is so easily recognizable,

She could put off that crown, but once a princess, always a princess.

Chastity College: Week One ~ now 30% off until Dec 12.https://www.smashwords.com/books/view/739920Thanks so much for supporting my writing. <3

Well Darling, I have never even heard of anyone actually playing with chastity.Sure, I have read about it in books about knights and princesses and such.But then it was always the princess in chastity. Certainly no interest there.But if you close that

Anonymous requested: Could you do where a husband and wife are both locked in chastity by a Bratty Princess that never lets them cum? P.S. Love your captions

Can you create a caption of a very sexy picture of amber heard using a chastity slave to clean her and her lovers cars while they have sex (or something along those lines). Something about how chastity is the only thing that makes me useful.

Selena Gomez chaste foot slave for life?

Could you do a Hayden Panettiere Ass slave?

Could you make a caption of chastity with Kat Graham. thanks

bukkakemeplease:Could you please do a chastity caption with Emilia Clarke?& Anonymous:Can you please make some Emilia Clarke captions!

bootfan requested:I’d love to see Ariana Grande humiliating Her chastity slave!

Anonymous: Please do ariel winter chastity. Not sissy stuff though. Thanks in advance.

Kylie Jenner Week

Kylie Jenner Week please do a Kylie Jenner one

Kylie Jenner Week

It’s Hump Day and Jessica has news about the Sissy Princess Patreon page!

Once a sissy understands her place she then knows where her clitty belongs… locked 4ever! ~ Sissy Princess on Patreon https://www.patreon.com/sissyprincess

That’s so funny.Oh, and hot. She made me promise to tell you it was hot and sexy.But really, showing me your caged cock and then turning around and showing me your princess plug in a public park…Come on, that’s funny.

Princess Katrina 💋

tangodeltawilli: Shiny bottoms. Check.See thru top. Check.Week’s vacation. Check.Metal Chastity cage and princess plug. Check and double check.Well Hubby, I think we are ready to hit the beach, don’t you?

Princess Katrina 💋

chastity-slaves-obey: Anonymous requested: Could you do where a husband and wife are both locked in chastity by a Bratty Princess that never lets them cum? P.S. Love your captions

sassyprincessesslavehusband: Going on day 6 now and I have completely swollen up in my cage…I miss this, the lack of control, the stimulation, the anxiety, the pink lock and best of all, I miss serving my princess.

petofaprincess: Locked up for Princess

freakycleanxxx: Waking up in chastity and princess plugged October 21st.

Princess E's slut

Princess E's slut

chastefetish: Princess teased my caged cock earlier, saying that this is the only head I’ll get from now on. Thank you for playing with your caged toy earlier, and thank you for denying me for your amusement.

themistress669: Hmmm locked up… as you belong princess

Chastity belongs in any good relationship. It isn’t JUST about me getting what I want. It makes his life better, too. He used to hate doing his half of the chores. Now he does dishes in nothing but the cage. And we always put a princess plug in

tangodeltawilli: Well Darling, I have never even heard of anyone actually playing with chastity.Sure, I have read about it in books about knights and princesses and such.But then it was always the princess in chastity. Certainly no interest there.But

princess-hannah18:You thought you had any semblance of control ? Oh how cute. Don’t worry slave, you’ll soon learn -princess Hanna is in complete control. I OWN you

princess-hannah18:It belongs to me. If you want to stroke you’ll need to pay

Princess Luisas Caption Factory

Princess&Chastity

Princess Denied

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