8 XXX : first time chastity

Told my bf he could fuck me for the first time in over a year if he just stayed locked until his birthday (Dec 9)....wait till he unwraps his first present ;)too mean??

imgur.com category @teasequeen1133

First time in this sub. Enjoy!

imgur.com category @sissy_alt

First time

imgur.com category @Chasta100

first time locked (album) - 24 hours so far...

imgur.com category @PhilipKThick

First time ;)

imgur.com category @Femsissysub

Finally locked for the first time. :3

imgur.com category @kishby

First time locked up for a week, wish me luck!

imgur.com category @Chastityslut69

25M my first time locked up

imgur.com category @CodieConner

Locked up for the first time

imgur.com category @BadDovah

First time in chastity. I think it might be a bit too small. Any tips?

imgur.com category @T00rpedo

Morning wood and about to go get fucked for the first time!

imgur.com category @Chastityslut69

Wife is Going on a Date for the First Time in Months.

imgur.com category @SacramentoCuckold

First time, hope you guys like ;) (PMs Welcome)

imgur.com category @LockedSlave215

First time in chastity

imgur.com category @subboycalgary

For the first time ever, the keys to my lock are in somebody else's posession

imgur.com category @Xorda

First time locked up :)

imgur.com category @soflobroyo

First time in chastity. How'd I do?

imgur.com category @smoothnhosedcd

First time in chastity - 24 hours in.

imgur.com category @TakeMyWhole

First time posting, favorite pictures I've ever taken of myself

imgur.com category @Sissyrohanna

First time locked up. I can't stand it.

imgur.com category @SecretLifeOfASissy

first time in chastity

imgur.com category @LikeALadyPerhaps

First time trying this.

imgur.com category @Traptsmile0531

First time caged at work. Left keys at home

imgur.com category @Imnotapintobean

Ate my cum after cuming in my cage for the first time. Mistress was kind enough to give me a kiss.

imgur.com category @The2inchPunisher

Caged and plugged for the first time

imgur.com category @Throwawayboy_93

Wifey locked me up for the first time and went to work

imgur.com category @THINGSTOPLAYWITH

First time posting! Locked up for two weeks and feel like sharing

imgur.com category @throwawaynotthrowawy

Locked up for the first time, the wife told me that if she can't cum there is no reason for me to.

imgur.com category @kindabi420

Wearing to work for the first time.

imgur.com category @Terrasque976

Need some first time help

imgur.com category @throwaway_j-i-c

First time post.

imgur.com category @Keira2000

Taking Chance for the First Time

imgur.com category @addyftw1

First time locked up. 2 hours for every upvote.

imgur.com category @tendersiss

Familiar with chastity, new to sissification. First time poster. Am I doing this right?

imgur.com category @secretsissykins

Got sissied up for the first time with my cage on and took some pics!

imgur.com category @JessicaSissyCumSlut

First time posting, should I do it more?

imgur.com category @sissy_slut_kikme9999

Crazy to think my first time with dick inside my hurt and I thought I’d never want it. Now I crave it and I’m making this face. I’d like to thank my cage for that. :)

imgur.com category @[deleted]

First time using my first dildo! Love it soo much!

gfycat.com category @My-N-quite-SFW-alt

First time in chastity, you can tell I’m a bit excited!

imgur.com category @Thisisntathroaway

Gave a blowjob for the first time yesterday and I loved every second

imgur.com category @SisKayra

I fucked myself for the first time while caged earlier!

gfycat.com category @CinBDSMthrowaway

First time!!!!

gfycat.com category @Mentok27

First time showing my face while being caged and fucked

gfycat.com category @3r5r

First Time!

imgur.com category @Rx8er1

My first time cumming in chastity!

gfycat.com category @ChasteAlex

First time locked!

imgur.com category @Nsfwclone20

I'm LOVING being locked up at her will for the first time

imgur.com category @bisexualbi

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!

gfycat.com category @SissyEmilys

First Time Posting (pt. 1)

gfycat.com category @Friendlysergal

Taking [M]y M/F Elliott past his massive coronial ridge for the first time. I have never had another toy make me quiver before just by inserting it.

gfycat.com category @BadDragon19