jesswintersof2Page 2

It’s Friday night and I’m in totally sissy maid mode 😉 who r..

The only appropriate skirt length for a sissy 💕

im trying so hard to knot this monster... omg PS I have qui..

🥶

Stay warm guys it’s still cold out here in NY! 😭 Reminder <..

ahn~~ i promise i will~~ ahh, i promise i will get an A next..

Mmm, as you can see, sissy got a new toy!! Hopefully I don’t..

Hey babes !! Vacation is over, guess whos back !!

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

White 🤍

Can you see the differences? Can you tell what makes a sissy..

Hey guys 🙂 I’m try to not neglect any of my pages. I took a ..

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

Cute selfiesss and pink outfit 💕💕💕💕

Since my sex machine broke, it seems like i will be doing th..

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

Just a small little video of me having a little fun with my ..

Wanna find out how deep it’ll go ? We will find out this wee..

omg.. i have waited WAY TOO LONG for this... i really destro..

Omg someone made these captions of me 😳(thanks mistress Mari..

I said I’d play, I never said I’d play nice ;)

Hey guys I’m back!! (Sorry I’m posting this late) While on m..

I wish all my seats and chairs came with this huge plug to d..

Mmm I love riding this horse-shaped red cock so much. Makes ..

Need a hot date asap 😜

It was my birthday yesterday! Busy weekend and thank you all..

One after the other i take my toys and fantasize that im the..

Let’s play ;)

Hehe I was feeling a little cheeky.. More on my full page I ..

Hey friends!! It’s almost the weekend and this sissy REALLY ..

If you came home and walked in and saw this sissy plugged op..

Tennis outfit for a very athletic girl !! What if I told u I..

I think it means she likes you

A sissy’s night in 😋😋😋 I have fun!

OMG. This is the biggest blackest toy i own. I finally got i..

How do you guys feel about my content where I suck / lick / ..

Just a new PFP and wanted to post it :) nothin crazy ! 💕

Hey guysss ! Some unexpected stuff happened this weekend (no..

ngl i came so hard from this... people arent kidding when th..

oh my god one of my favorite things to do... the only thing ..

Give me a D!!

Blue green yellow purple 💙💚💛💜 Got some good stuff coming soo..

Who’s going to cum and play with me

Just a new pfp :)

Hope everyone had a nice weekend 🖤🖤🖤 Hot stuff coming tomorr..

actually kinda hard to control the speed of your blowjob whe..

Hey I’m actually really curious about you guys.. what time i..

Starting to love this Black dress and stockings combo ;)

I never thought I'd be in this situation.. Being spit roaste..

I know I have at least a few fans who lightly dabble in furr..