jaydensteele

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

Chastity check by the hiking trail 🫣 1st solo task done ✅ A couple more to go: - Self spanking (Video) - Sissy walk in public (Video) Any other ideas?

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

Sub Boy Mode ✅ Tip to make my day 😊 What would you like to see me wearing in my videos?

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

Brutal ball kicking session with Mistress, you can hear her enjoying it by the laughing as I crumble to the ground clutching my swollen balls 😫 Tip for the risk of being made sterile I take from getting my balls beaten 😅

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

Sometimes when we’re driving I can get a bit annoying so Mistress has learned a quick way to fix my attitude is by pulling over to the road side and spanking my bare bottom just out of view of the people driving by, I’ve only had to walk back without my pants on once but safe to say my face was ...

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

Pre Spanking Ritual: Make your boy go to his room and wait for you with his pants around his ankles. As he’s waiting for you the feeling of fear and humiliation will set in, he’ll also know that that feeling will soon be replaced by just one feeling, a intensely overwhelmingly painful sting on ...

Humiliating chastity check on the balcony 😫

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

Jayden has some time by himself next week so I’ve told him to do some solo videos for you guys, there’s also some relatively quiet hiking trails nearby… Let me know what tasks/content you want him to do

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..

I’ve been a bit sick over the weekend unfortunately but still trying to post, got a couple of new videos planned to film when I’m better! Unrelated but where are the most humiliating/embarrassing places you’ve either been spanked or spanked someone? (Let me know in the comments) Personally ...

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

Mistress is out and I’m locked in chastity so figured I’d do a sissy photoshoot 👠💄👗 Tip for a sissy surprise in your inbox 😈

Who wants to tan with me? 😉

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

I got so horny when Mistress locked me up and went out that I started spanking myself… Who wants a turn?

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

Storytime: I said something mean about one of Mistresses gay friends so she threatened so send him a video of me in a miniskirt with a dildo down my throat unless I videoed myself at the gym wearing these see through PRIDE speedos and my chastity cage. It was super embarrassing with the thought of s...

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

Made to show off my smooth hole to anyone walking past 😳 What kind of punishment to boys who are rude need?

Nutcracker 😫

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

Sissy Task: (From Mistress V) 1. Lock yourself in chastity 2. Dress up in your girliest clothes (Lingerie, Heels, Dress, Makeup, Ect) 3. Get a dildo and video yourself sucking it and riding its whilst moaning and saying slutty things 4. Post it to X and tag @thekinkyboss

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

Chastity Check ✅ She locked me up the other day because I couldn’t make her cum with my dick, so now I’m locked up for a week and only allowed to use my tongue 👅 Changing at the gym is gonna be embarrassing 😳

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

Mistress wants to take me to Bangkok and make me walk around wearing this dress, heels and makeup… Tip if you want to see me walking the streets looking like a sissy 🤭

What’s your favourite spanking position?

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

On my hands and knees with my girlfriend taking her frustration out on my poor balls, she said I was complaining too much so she gagged me too 😭 We’ll make another video soon with ONLY HARD KICKS! Every $1 tip = 1 kick 😫 I think I’ve only taken about 5 hard kicks in a row before…