jesswintersof posts
A dusty mirror pic of my caged clitty and my feet 🙄
A dusty mirror pic of my caged clitty and my feet 🙄
2023-03-28 02:08:20 +0000 UTC View PostWhen I went from a pink small to a pink nano ☺️
When I went from a pink small to a pink nano ☺️
2023-03-28 02:04:48 +0000 UTC View PostSomeone wanted to see my cute pink pedicure!
Someone wanted to see my cute pink pedicure!
2023-03-28 02:02:46 +0000 UTC View PostTwo of my older pfps still using a filter lol
Two of my older pfps still using a filter lol
2023-03-28 02:02:05 +0000 UTC View Post
With socks… without socks… or without panties and skirt 😛
With socks… without socks… or without panties and skirt 😛
2023-03-28 01:47:01 +0000 UTC View PostThis was my pfp for a short while in 2022.
This was my pfp for a short while in 2022.
2023-03-28 01:46:01 +0000 UTC View PostHard to take pictures when your wrists are chained 😩💕
Hard to take pictures when your wrists are chained 😩💕
2023-03-28 01:36:11 +0000 UTC View PostBought myself a cute new choker with lock charm .. 🔒
Bought myself a cute new choker with lock charm .. 🔒
2023-03-28 01:28:58 +0000 UTC View PostEarly 2022… This is around when I stopped relying on filter..
Early 2022…
This is around when I stopped relying on filters but still didn’t know about makeup yet… ugh.. Jessica…
Sometimes I just wanna play sissy maid.. 💕
Sometimes I just wanna play sissy maid.. 💕
2023-03-28 01:26:24 +0000 UTC View PostA sissy needs to be plugged…. So I did ! 🧎♀️
A sissy needs to be plugged…. So I did ! 🧎♀️
2023-03-28 01:24:41 +0000 UTC View Post
Collared, cuffed, ready to be owned…
Collared, cuffed, ready to be owned…
2023-03-28 01:19:17 +0000 UTC View Post“Let’s compare my caged clitty to a good size toy..”
“Let’s compare my caged clitty to a good size toy..”
2023-03-28 01:17:58 +0000 UTC View PostPresenting myself as a good sissy maid for you all💕
Presenting myself as a good sissy maid for you all💕
2023-03-28 01:16:59 +0000 UTC View PostThis orange dress makes a return… and I love this pink skirt..
This orange dress makes a return… and I love this pink skirt !
2023-03-28 01:15:04 +0000 UTC View PostChained to the bed.. locked on.. nowhere to go..
Chained to the bed.. locked on.. nowhere to go..
2023-03-28 01:10:03 +0000 UTC View Post
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 😵💫
2023-03-28 01:07:36 +0000 UTC View PostVideo 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…? ;)
2023-03-28 01:04:47 +0000 UTC View PostCollared, chained, handcuffed behind the back. 🔒
Collared, chained, handcuffed behind the back. 🔒
2023-03-28 01:02:50 +0000 UTC View PostOops idiot sissy accidentally turned her webcam on !!
Oops idiot sissy accidentally turned her webcam on !!
2023-03-28 01:01:18 +0000 UTC View PostThe first time I stepped outside dressed .. even if I kinda ..
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:)
“A sissy tgirl’s bed after a shopping spree” ahaa ! 💕
“A sissy tgirl’s bed after a shopping spree” ahaa ! 💕
2023-03-28 00:58:34 +0000 UTC View Post
I used to think *this* was a short skirt.. this is wayyyy to..
I used to think *this* was a short skirt.. this is wayyyy too long !!
2023-03-28 00:56:07 +0000 UTC View Post
