First Time Chastity Clip Fuck

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First time upload & sissygasm after being locked in chastity for 3days, teased with hypno, please call me a sissy and emasculate to keep me motivated!

(OC) first time in chastity, loving each second 🖤

Kik slavefagboy69 Got poppers looking to try for first time seeking abuse and domination

Couldn't wait for #femboyfriday, my first time getting dressed up and locked up like this! Hope y'all like it <3

My first time ever in chastity. About to go for a nice little walk like this 💜💜🖤🖤🔗🔗

Tried sounding for the first time... In my cage

Cumming in my cage for the first time. Desperate for someone to obey.

My first time doing butt stuff in chastity

My first time riding my dildo, how did i do? 😅

Posting here for the first time, now I know it belongs here

1 week in chastity and in that week I've posted pics & vids, flirted with strangers AND downloaded Grindr for the first time - it's been a good week

This is the first time using this toy and i managed to fit it all in🥵 Encourage me to bounce on it some more🤤

New chastity student gets automatic prostate massager inserted into his asshole for the FIRST TIME. I hope you get it now why we restrain our students for this kind of procedures.

Fucking my ass for the first time

Home alone for the first time in months, Mistress suggested I share this video here and ask for ideas for tonight.

My first time trying Blowjob. Now I want the real one ASAP! <3

My first time in chastity. And yes I need to buy a smaller one.

caged and plugged at the same time ? its my first time caged!

Day 7: told him before we put the cage on that if he made it a full week for the first time that I would give him a blowjob as a reward 😜 what I didn't say was that I wasn't going to remove the cage first 😈🙈

Throwback to one of the first times Master assfucked me in my old belt

Ruined his orgasm for the first time in his little acorn cage... He was so full it ended up all over his face!

I decided to share my favorite toy for two minutes 🤭 he must have enjoyed it! First time trying to cum in the inverted cage was successful 🤭😘

It’s normal to be nervous the first time

My gf(who doesn't know i am a sissy) is out of time perfect time to try and take this monster bbc dildo fully for the first time. I have a long way to go,35cm to be precise😰kik janisjanis1

A teaser from the session where I ruined my man for the first time during Locktober 🙌🏼❤️ [f] [m]

throwback to one of the first times I was locked

Wondering my wife strapon on our pegging training? First time video of us 😊

Master let me cum from anal only with my vibrating plug for the first time and I loved it, please don't make fun of my moaning 👉👈

I just love being filled to the balls and then gaped. Do you think that when the time comes to take a real cock for the first time, that I'll be able to handle it?

Fucking the precum out of myself. First time fucking myself like this

After 3 days in chastity for the first time, I simply could resist. Do you see a potential for a good sissy?

Went outside dressed like a girl for the first time ever! I got so excited I must've forgotten my panties at home.

The first time I put all 8 inches in

Finally - first time cumming in chastity

Big cocks first time in a cage 😈

my first time in chastity it was a lot of fun ;) (20)

how it feels to have a vibrator in my boypussy (this was my first time 😳)

Luke, a good friend of mine, is now also my chastity slave🤭🔐🙇🏻‍♂️ This is his first time being locked up and teased by me☺️👸🏼 We had to take some breaks because his loser cock kept getting hard🤭

His first time! Putting it where it belongs. Save, protected, controlled. I own him, completly 🔒🥰️

The first time in the cage🔒 will be so special, remember, their is no going back when I have the key!🔑

My first time, it felt amazing :) Just need to use another cage, when I do it again.

For the first time in his life, the lock clicked on my new puppy's cock, and the #chastity was attached!🍆🔒 My #slave is used to me treating him hard. The 🐶 still has to get used to this. But they really enjoyed the nippleclamps🔥

Sissy training first time pegging in chastity

My Fan paid me to Unlock for the first time in 60 Days🥹

today i can finally deepthroat for the first time

Locking up my hubby for the first time and making him watch me fuck another man

Hubby got quite an experience. He actually got to cum twice 🤭. I was fucking his ass when he came for the first time, but I wasn't finished so I kept going while I used his own cum as lube until I had enough fun 😈😘

Locking up for 72 hours for the first time. My previous best is 36 hours and I’m excited to beat it with the help of my new timed lockbox.

New to Chastity: First Time with the Magic Wand

Day 12 - He told me he was desperate today for the first time, I think we should celebrate the milestone 🤭

Training Day - Days Gone Bi! Just look how eager he is. He really doesn't need my hand on the back of his head, it just makes him feel better about taking a cock in his mouth for the first time.

Hubbys first time in chastity!

My first time with inverted cage

My first time cumming in my cage! It felt so good

Putting hubby in a cage for the first time while I go out on a date

Trying my knot for the first time, sooo good!

Sissy's First Time in a FLAT CAGE

My First Time being locked up

Had to meet my bf's family for the first time 😏, but had to remind him after we settled at his mom's house that he was still my bitch by claiming his naughty little hole and slapping those useless balls of his 😜🤭.

Went to the beach in a bikini for the first time! (With a little surprise 👀)

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