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Sissy Anal Training

Tongue dance whilst locked in chastity

Hole training with a bit of moaning ☺️

Intense training session

Because he is locked up so long, he have to train, penetrating.. but not with his mini-wiener❤🗝️

Daily anal training is really starting to pay off

Making my cage bounce while I train my hole

I have Subby trained to be a good boy and cum by the touch of my finger. ❤️ 🔐

Accidentally discover a new way to release while training for nipple orgasm. Was edging using this technique for about 10+ mins and finally squirt a bit out 😥😥

daily training is very important for aspiring girlies ;)

I train to walk in high heels like a good bitch ?

Night train, all alone, kinda bored, so I had a naughty little idea... Trip suddenly got more fun with some locked-up, NNN-friendly whiteboy sex to pass the time! 😇

I'm training him to be the best whore.

Poppers Training

Torture & Blowjob training for my chastity sissy😈

Slapping my locked balls around with my new dildo before setting me off to train my hole

[OC] The premature training is permanent, do you think your nub will ever grow back to it's previous size?

Locking my cock away and training my ass like a good little white boy 🙈

Clean Shaved for my first stint being caged. I guess its time to start training my virgin asshole

27 Sissy MA. Ownership? Sissy training? Forced Feminization...?

Sissy sex slave: ready to submit to training regimen

Do you want to help me train? 🥰 Kik: sissy.sophia. with 2 dots in the name

I promised him release... However, I changed my mind after some attitude issues. Instead, I surprised him and put him back in his chastity cage. I know it seems tough, but this is how I train you to respect me.

12 Steps to Chastity: 4 Week FemDom Training and Rehabilitation Program LINKS AND DETAILS BELOW! ⬇️

Working that dildo like it was the real thing... Training is important

Sissy training with huge dildo GIF by sissydelilahsnow

My mandatory deepthroat training

My personal pussy licking slave is so well trained

a little bit of my daily training

ESTIM Chastity Anal Training At INSTITUTION X

My wife getting more hard on my feminization training 🥹

Made him wear my dress and panties to start training his ass

I always new I want my cucky bf to be on a clean up duty, this is how I trained him to do so

good girls submit to training...

Daily training is essential for all sissy sluts 💜

My gf has trained me to need jizz

During Locktober I had ample opportunity to train my ass 😳

Routine pegging training preparation for his own bull.

Even complete fuckdolls need training to improve!

[oc] sissy maid training

keeping trained for big d*cks

I hope you are trained because I will destroy your bitch mouth

[20] Smooth, caged London sissy looking for a man to meet regularly and train me, dm if interested 😘

I think my training is going well. How about you?

A good oral training routine is very important for a Sissy 😇

cuckold in his daily anal training (6 months pussyfree, chastity belt for months and counting)

You'll forget what your dick used to be with patience and regular training!

[oc] trained and tamed in chastity 🥲

How's my training going?

Deepthroat Training for my Femboy Sissy

(18) anyone wanna train my sissy ass?

Sissy slut training 🎀

As my inverted cage training continues, my alrernate nub cage is starting to feel very roomy lol

Cage check in the train

ALOT of training to get to this point. How long did it take you to learn to cum hands free?

Teasing, rubbing & training my cunt for a hard pounding

Caged and ready for training, are you prepared to follow my every command while I hold the key to your freedom?

[oc] Most days are spent in the dog cage 😣. But my gf has made me into such a well-trained puppy boy 😣 I always wait for her approving stare, even if the reward is just her sweaty feet 😭

Starting my own himbo training class 😈

Day 2 - I continue to train