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Sissy Anal Training

Ruined Anal-O

Locktober cum from anal

u/thiscaden - Anal Training

17 days since my last orgasm. Mistress wanted me to try cumming from anal. Couldn't quite get it. I'm frustrated!

First time anal after a long time 😊

SissyJoyce's First Anal Orgasm

My love language is anal. 💜🍑

I get so horny for anal when I'm locked up!

I can’t get enough anal

Just something about being shiny and caged makes anal feel so much better...

(OC) Wearing a cage makes anal so much more fun 🥺

15 pumps on my anal balloon to help stretch my ass out

I put on a cage for fun and am currently trying to cum from anal only! Would probably be easier if it was u instead tho...

Locked clit anal orgasm

With me you either cum solely from anal or you don't cum at all. With all my sissies it's only a matter of time before they cum from anal, even when wearing a tiny cage.

Cumming solely from anal stimulation while my useless limp cock is locked up is such an emasculating feeling. I can't get enough of it. This is the only way I want to cum from here on out.

Being locked up turns me into such an anal slut.

Ellie's anal training as promised yesterday

Daily anal training, please tell me if you want to add something for today 😖

Spontaneous training session left me craving for real dickChastity Anal Dildo Porn GIF by sokebf1001

Heels and anal make depth training more intense

novice level anal training: my first vibrator

The point of the cage was so that I don’t cum so fast from anal but now even that’s not working 😩

Had some fun practicing for anal orgasm this morning

Hopefully one day I'll cum from anal

my first time Cummings from anal!! Finally!

the sound of chastity

part 1 of this chubby sissy in chastity dildo training part 2 can be found on my redgifs

A chastity makes me even more horny

trying the Fucking Machine at full speed while in Chastity

48 hours in chastity and begging for any release help me daddy? 🥺

Flat cage anal training

Making good use of my anal toy, tormented with the wand aswell.

Stuffing my sissy hole with my two biggest toys. (Flat cage, double anal)

Precum from anal

Just another anal slut

Just anal slut stuff

This anal orgasm in my cage left me in awe 🥵

cumming from anal every day for a week. How long should I go for?

What should speak against it, if the keyholder and the chaste want to enjoy the anal pleasures together?

Gym Anal Doggy by futalab.blogspot.com

I couldn't achieve an anal orgasm so I got weak and cheated

Someone asked me if I can cum from anal only. Answer is yes 😏(31s, sound on)

Felt a bit too good~ 🥴

this orgasm left me broken

Locktober Sissygasm 🎃💦

A little leaky 🥴

This feels so good, everytime

No need to unlock when there's an anal ring

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I can't stop cumming like this 😵‍💫

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promise to keep fucking after i cum? 😻

Training me everyday

Only one priority

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First time here. Enjoy footage of my sissy anal orgasm

Cumming Through My Panties From Anal Play