8 XXX : chastity training

Chastity training for sissies

imgur.com category @[deleted]

Chastity training for sissies

imgur.com category @[deleted]

Depth training while locked up, I love lazy Sundays!

imgur.com category @tlps

Straining in Training

imgur.com category @tarsapo13

Chastity training for sissies

imgur.com category @[deleted]

Chastity training for sissies

imgur.com category @[deleted]

Sissy chastity training

imgur.com category @[deleted]

Kinky Chastity Tease

imgur.com category @missbratdom

Chastity training for sissies

imgur.com category @[deleted]

P.C.S. new jobs for chastity sissies

imgur.com category @[deleted]

Chastity Fun

imgur.com category @missbratdom

Let's hope I don't get tanlines... [crosspost from /r/chastity]

tumblr.com category @whizz

In chastity for my feet (GIF)

imgur.com category @missbratdom

Chastity belt plug training - Kami Tora

imgur.com category @darktruth

Training day~

imgur.com category @Revzyuu

Slave being trained by another slave in front of the Master, with remove control toy, secured by a chastity belt. One of my fantasies (xpost MastaHarem)

gfycat.com category @Masta808throwaway

sissy in chastity

imgur.com category @tvsubslut

Training in a tight fancy chastity belt

imgur.com category @Lock-Master

Training (cartoon)

imgur.com category @xchangepill

Thursday training session in progress

gfycat.com category @finsiss

Training sissygasms with my new 9" BBC

gfycat.com category @bby_alana_xx

How long should my slitty stay locked? Need a daddy to train me

imgur.com category @[deleted]

Sissy training daddy 9" and friend 10" - 6 of 6

gfycat.com category @bby_alana_xx

Itty bitty clitty training

imgur.com category @skeeboi

Natalie Mars showing is inside her well-trained pussy

imgur.com category @boysarethebestgirls

One month locked up really makes a big difference in sissy training...

imgur.com category @DaceyCD

Deepthroat Training by VoidNosferstu

imgur.com category @aimless_ascendant

Training in a tight fancy chastity belt

imgur.com category @Lock-Master

Starting His Training

imgur.com category @AtlantisStar

About to get trained real well

tumblr.com category @account4244

School Girl Training

tumblr.com category @account4244

Training Complete

tumblr.com category @account4244

What’s being caged for if not to train your ass?

gfycat.com category @whoevencares69420

Training ;)

gfycat.com category @LovinPink

Sissygasm Anal BBC Training (Part 3)

gfycat.com category @bby_alana_xx

Anal training with sissygasm - 3 of 3

gfycat.com category @bby_alana_xx

Sissy training daddy 9" and friend 10" - 4 of 6

gfycat.com category @bby_alana_xx

Thursday training session in progress.

gfycat.com category @finsiss

training my pussy

gfycat.com category @HubiBert

training my boy pussy for big cocks

gfycat.com category @little_sissy_

Sissy training daddy 9" and friend 10" - 5 of 6

gfycat.com category @bby_alana_xx

Training my sissy hole while dressed and in chastity

imgur.com category @evaLockedSissy

Wednesday training session: riding my dildo until I start leaking

gfycat.com category @throwaway070617

Chastity belt training

imgur.com category @Lock-Master

Training in a tight fancy chastity belt

imgur.com category @spacecowboyr

I thought chastity was supposed to stop cumming .... Not for this cuck! I LOVE locked orgasms!

gfycat.com category @Umbrii_xo

Couldn't find a proper chastity app to track my time locked, so I created a quick one. I hope to stay above the 50% mark at the end of the year

imgur.com category @libertosurf

What was your training schedule? Longest for me is 2 weeks with HT but can't get past 3 days with the cherry keeper.

imgur.com category @Rx8er1

Starting to play around with chastity. As a grower it’s usually fine and I can feel the direction getting trapped and stopped by it. But this happens with morning wood. I’m assuming that’s not supposed to do that. What am I doing wrong?

imgur.com category @Alabehr

training my sissy hole

gfycat.com category @bby_alana_xx