jesswintersof

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jesswintersof posts

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ahn~~ i promise i will-- ah~ i will get an A+ next week~~ i ..

ahn~~ i promise i will-- ah~ i will get an A+ next week~~ i promise!

😜😜😜😜😜😜 gonna be a crazy week 😜😜😜😜😜😜

i love when i let the machine do the work, i dont know what ..

i love when i let the machine do the work, i dont know what kind of pattern its going to give me, it surprises me and theres nothing i love more than surprises ;)

Hey everybody !! My vacation is over, I had to work this wee..

Hey everybody !! My vacation is over, I had to work this week but guess who’s back!! 💕 can’t wait to post the videos I made for you this week . Much love to all!!

jesswintersof post Just a lil smthhhh . !! from onlyfans

see how hard i am trying to knot this thing... i was told im..

see how hard i am trying to knot this thing... i was told im not allowed to remove the cage until i take it all like a good girl...

jesswintersof post White 🤍 from onlyfans

Can you spot the differences ? Are you able to tell what mak..

Can you spot the differences ? Are you able to tell what makes this sissy happier and happier? 😉😊

At least I was left with a toy to play with 🥺

happy Friday guys 🙂! I didn’t know how to “announce” this so..

happy Friday guys 🙂! I didn’t know how to “announce” this so ill just say it, im finally going to start HRT ☺️ . Early January! If anyone wishes to give general advice/brief info, feel free to do so in my DMs or reply . Thanks for the wishesss! Here comes an interesting 2024 💕!

Selfies and outfits hehe 💕💕💕

i so love butt stuff

I do these things for your pleasure.... ok.. mine too, just ..

I do these things for your pleasure.... ok.. mine too, just a little bit (;

;) this plug is more fun than it may seem . . . I’d still ra..

;) this plug is more fun than it may seem . . . I’d still rather you replace it though . . .!

hehe had a fun little night. bit of light home-made predicam..

hehe had a fun little night. bit of light home-made predicament self bondage... i tied my nipple clamps a strap under my bed and pushed it close to my machine so that it would force me to stay close and take the dildo really deep. if i pulled away from the machine too much it would pull on and hurt my nipples.. love this stuff . . . added fun with a gag and of course i'm caged in chastity.. hope you guys enjoy.. I wanna do more like this......

For all my subs and supporters on this page I just want you ..

For all my subs and supporters on this page I just want you to know some good stuff is coming !! I bought all sorts of fun stuff cute outfits and I feel better than I did when I was sick! I’m goin to be trying some new stuff out too (new type of content) , and yeah !! Just wanted to say thanks for sticking around and expect really fun stuff 😉 💕

Short little video of me having a bit of fun hehe

My chastity journey hehe

Loved my pink HT style cage it got me to where I am today 💕

I don’t have a problem I can stop anytime I want !

Wanna find out how deep it’ll go ? 😍😍

short clip of my last video.. sorry about the booty acne, ca..

short clip of my last video.. sorry about the booty acne, cant be perfect all the time... ANYWAY.. i think i found my new favorite type of toy.. hehehe 😍

i think i found my new favorite type of toy... inflatables....

i think i found my new favorite type of toy... inflatables...

i have really made you wait for this... i REALLY felt my ass..

i have really made you wait for this... i REALLY felt my ass being stretched and kind of destroyed so hard with this omg. I FKN LOVED IT!! This is the **2nd** biggest toy i have... which means.... i think you know

These were made by someone on Twitter named “mistress mariac..

These were made by someone on Twitter named “mistress mariaclaire” (I didn’t ask them to make these I just got sent them lol) But wanted to put them all out here for you guys to see xx thanks for everything and I’ll be back with my regular new posts when I’m over this horrible cough Much love!!!