jaydensteele | Page 3

In our relationship I’m not caged 24/7 purely because it jus..

Just her plaything ☺️

Which view do you prefer?

What are your favourite ways aside from spanking to punish n..

First time trying a hanging wedgie, turns out they hurt more..

She’s training me to take a real one 😩

Hanging wedgie gone wrong 😫 Got a bit stuck lol

Learning my lesson with the cane 😭 I forgot how much the ca..

Nothing more thrilling than doing a sissy photo shoot on a h..

Chastity check by the hiking trail 🫣 1st solo task done ✅ ..

Sub Boy Mode ✅ Tip to make my day 😊 What would you like to..

Brutal ball kicking session with Mistress, you can hear her ..

Sometimes when we’re driving I can get a bit annoying so Mis..

Pre Spanking Ritual: Make your boy go to his room and wait ..

Humiliating chastity check on the balcony 😫

Jayden has some time by himself next week so I’ve told him t..

Well I don’t think I’ll manage to get this cage off 😅

Just chillin

I’ve been a bit sick over the weekend unfortunately but stil..

Mistress is out and I’m locked in chastity so figured I’d do..

Who wants to tan with me? 😉

I got so horny when Mistress locked me up and went out that ..

Storytime: I said something mean about one of Mistresses gay..

Made to show off my smooth hole to anyone walking past 😳 Wh..

Nutcracker 😫

Sissy Task: (From Mistress V) 1. Lock yourself in chastity ..

Chastity Check ✅ She locked me up the other day because I c..

Mistress wants to take me to Bangkok and make me walk around..

What’s your favourite spanking position?

On my hands and knees with my girlfriend taking her frustrat..

Comment ‘me’ if you want a list of BDSM tasks and she’ll sen..

I lost most of my old pictures of my spanking from when I wa..

I was allowed to edge myself before being locked back up in ..

Just short enough so everyone can see my chastity cage and s..

I’m only allowed to make myself cum by slapping my own balls..

She made me drink my own cum 🫣

Locked to the balcony by my chastity cage 😳

Ways to humiliate a sub: 1. Exposing them to your friends 2..

Face down, Ass up, Hole ready… Anyone who refers my profile..

Whats wrong with this picture?

Signs of a well spanked boy: 1. He’s crying & apologetic 2..

[Mistress V] Jayden posted this picture of him at 18 to twit..

Honestly the feeling of being tied up and jerked off, unable..

Who wants to come for a swim with me?

Just a boy in a jockstrap (+ a speedo tan)

What kind of humiliation punishments do you give/receive? M..

If you caught me trespassing like this what would you do?

Getting my balls spanked 😢 As per usual I started moving to..

A reminder that when if we hit 100 subscribers I’ll be getti..

Pre-Shopping Spanking 📸