jesswintersofPage 5

Can’t wait for tonight!! Going to finally have time to play ..

Hey everyone !! I’m going through a move right now making it..

Hey allll ! I didn't forget about my pages ! Been busy but i..

Turns out I'm good at taking it on my back...and i fking lov..

Oops !! Wtf! I had some naughty little pix that were suppose..

i always wanted to be one of the cheerleaders when i was you..

let my warm mouth and open throat do all the work baby .. do..

holy fuckkk 😩😩 this feels so good .. all the while getting r..

training my tight sissy hole so im ready for you ..!

Sorry for a bit of a break with the content but I assure you..

What you think.. I need to go bigger, right? 😩😩😩

Training my sissy pussy with my machine and toys ! honestly ..

My hips and butt are finally wider than my waist!! Meaning I..

Old cage (pink) vs newer cage (black) side by side.. which o..

Don’t forget to feed me🥺

Oommfg love my machine so much.. felt so good I couldn’t eve..

❤️🖤

Couldn’t sit still on the bed !!

I love this skirt so much..

Felt cute or something idk ! <3

**Importantttt:** I uploaded as much content as I could in a..

A couple selfies turned PFP and a body pic ! <3

Idk why I took these .. I think it was just one of *those* m..

Just a bodyselfieeee

cute pink pfp

Cuffed, gagged, collared, and anal-hooked.. ⛓️

Graduated to a metal cage... theres no going back now...

Kind of a goth look... but only sorta .. !

I got my belly button pierced!!!!

Daddy can you please never take my collar off? 💕

I love this so muchhh ! 💕

This white tee is so big lol !

Oooh Oohh this skirt and stockings combo ...

<3

My ultimate "yes daddy" outfit... 💕 💕 💕

A Dom on Twitter wanted to make sure I was still locked duri..

Sissy is also a metalhead ?? (Yes...I am...)

A series of photos I made to make captions out of myself... ..

Another comparison I made for myself ! -- The "now" was mad..

Some seeelffieezzz

Pink hoodie blue eyes 💕💙

Simple