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A dusty mirror pic of my caged clitty and my feet 🙄

jesswintersof post A dusty mirror pic of my caged clitty and my feet 🙄 from onlyfans

A dusty mirror pic of my caged clitty and my feet 🙄

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When I went from a pink small to a pink nano ☺️

jesswintersof post When I went from a pink small to a pink nano ☺️ from onlyfans

When I went from a pink small to a pink nano ☺️

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Someone wanted to see my cute pink pedicure!

jesswintersof post Someone wanted to see my cute pink pedicure! from onlyfans

Someone wanted to see my cute pink pedicure!

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Two of my older pfps still using a filter lol

jesswintersof post Two of my older pfps still using a filter lol from onlyfans

Two of my older pfps still using a filter lol

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Mmmmphh

jesswintersof post Mmmmphh from onlyfans

Mmmmphh

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With socks… without socks… or without panties and skirt 😛

jesswintersof post With socks… without socks… or without panties and skirt 😛 from onlyfans

With socks… without socks… or without panties and skirt 😛

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This was my pfp for a short while in 2022.

jesswintersof post This was my pfp for a short while in 2022. from onlyfans

This was my pfp for a short while in 2022.

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Hard to take pictures when your wrists are chained 😩💕

jesswintersof post Hard to take pictures when your wrists are chained 😩💕 from onlyfans

Hard to take pictures when your wrists are chained 😩💕

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Bought myself a cute new choker with lock charm .. 🔒

jesswintersof post Bought myself a cute new choker with lock charm .. 🔒 from onlyfans

Bought myself a cute new choker with lock charm .. 🔒

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Early 2022… This is around when I stopped relying on filter..

jesswintersof post Early 2022…  This is around when I stopped relying on filter.. from onlyfans

Early 2022…
This is around when I stopped relying on filters but still didn’t know about makeup yet… ugh.. Jessica…

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Sometimes I just wanna play sissy maid.. 💕

jesswintersof post Sometimes I just wanna play sissy maid.. 💕 from onlyfans

Sometimes I just wanna play sissy maid.. 💕

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A sissy needs to be plugged…. So I did ! 🧎‍♀️

A sissy needs to be plugged…. So I did ! 🧎‍♀️

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Tbh idr taking theseee ! 💕

jesswintersof post Tbh idr taking theseee ! 💕 from onlyfans

Tbh idr taking theseee ! 💕

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Collared, cuffed, ready to be owned…

jesswintersof post Collared, cuffed, ready to be owned… from onlyfans

Collared, cuffed, ready to be owned…

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“Let’s compare my caged clitty to a good size toy..”

“Let’s compare my caged clitty to a good size toy..”

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Presenting myself as a good sissy maid for you all💕

jesswintersof post Presenting myself as a good sissy maid for you all💕 from onlyfans

Presenting myself as a good sissy maid for you all💕

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This orange dress makes a return… and I love this pink skirt..

jesswintersof post This orange dress makes a return… and I love this pink skirt.. from onlyfans

This orange dress makes a return… and I love this pink skirt !

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Teasing a little… 🤍

Teasing a little… 🤍

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Chained to the bed.. locked on.. nowhere to go..

jesswintersof post Chained to the bed.. locked on.. nowhere to go.. from onlyfans

Chained to the bed.. locked on.. nowhere to go..

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Some of my favorite heels

jesswintersof post Some of my favorite heels from onlyfans

Some of my favorite heels

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A 2021 video of me desperately humping a pillow and vibing m..

A 2021 video of me desperately humping a pillow and vibing myself trying to cum in chastity 😵‍💫

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Video from 2021! Sissy Jessica practicing on her pink dildo ..

Video from 2021! Sissy Jessica practicing on her pink dildo waiting for the real thing.. 💕 who wants to be her first blowjob…? ;)

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Collared, chained, handcuffed behind the back. 🔒

jesswintersof post Collared, chained, handcuffed behind the back. 🔒 from onlyfans

Collared, chained, handcuffed behind the back. 🔒

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Oops idiot sissy accidentally turned her webcam on !!

jesswintersof post Oops idiot sissy accidentally turned her webcam on !! from onlyfans

Oops idiot sissy accidentally turned her webcam on !!

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The first time I stepped outside dressed .. even if I kinda ..

jesswintersof post The first time I stepped outside dressed .. even if I kinda .. from onlyfans

The first time I stepped outside dressed .. even if I kinda knew no one would see me unless I was *really* unlucky (or LUCKY heehee) .
Always wanna save this pic to look back on:)

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“A sissy tgirl’s bed after a shopping spree” ahaa ! 💕

jesswintersof post “A sissy tgirl’s bed after a shopping spree” ahaa ! 💕 from onlyfans

“A sissy tgirl’s bed after a shopping spree” ahaa ! 💕

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Clitty pic from 2021!!

jesswintersof post Clitty pic from 2021!! from onlyfans

Clitty pic from 2021!!

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I used to think *this* was a short skirt.. this is wayyyy to..

jesswintersof post I used to think *this* was a short skirt.. this is wayyyy to.. from onlyfans

I used to think *this* was a short skirt.. this is wayyyy too long !!

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These heels are mega hot!!!

jesswintersof post These heels are mega hot!!! from onlyfans

These heels are mega hot!!!

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