8 XXX : those first 3

Safety First

imgur.com category @jakefratelli

Overwhelmed by her first milking

imgur.com category @automat1111

[Drawn] The first stage of a hucow's creation

imgur.com category @succubusl0v3r

Her first taste of the pumps

imgur.com category @honi_yudani

Went to my first kink party last night, had way too much fun

imgur.com category @starsissy17

the first week felt a bit strange, but now i would feel very naked without my chastity device

imgur.com category @shymax

A picture of me in my comfy chastity cage. (first post, I hope i'm doing it right)

imgur.com category @deviantsub

Just got my first cage :)

imgur.com category @lilycd88

woohoo got my first cage!

imgur.com category @Mc_Trash

She forced my first caged release

imgur.com category @Worshipyourqueen

my first cage. tightest spacer. incredible feeling

imgur.com category @Elusive_Desire

18 year old - first cage :)

imgur.com category @krchastity

Finally locked for the first time. :3

imgur.com category @kishby

Hi everyone this is my first post ;) (crosspost from r/sissies)

imgur.com category @Your_Ganymede

Trying out my first chastity cage

imgur.com category @GermanStud27

25M my first time locked up

imgur.com category @CodieConner

Locked up for the first time

imgur.com category @BadDovah

My first Device :D

imgur.com category @LA_boi

My first "milking" while in chastity. It was incredible!

imgur.com category @personobjectified

After my first night

imgur.com category @hwylup

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

I got my first chastity device today. I was so excited, I could barely get it on.

imgur.com category @AeonLeo

My first caption for the day... another one I made recently

imgur.com category @lockedforher

Just passed my first 24 hours consecutively locked up

imgur.com category @SluttyCagedBoy

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

imgur.com category @Xorda

Just got my first device today! It's nothing fancy but I'm still excited!

imgur.com category @ZTgirl

Keyholder feeling guilty: one of the captions I wrote myself. First post here!

imgur.com category @lockedforher

Sissy Maid in chastity (first post to this sub!)

imgur.com category @YourNewFetish

A Sir decided it was time to lock me up. It's my first night caged and I can't wait for many more.

imgur.com category @Checkme2807

My first post here.. mine btw

imgur.com category @BondageBri

[F]irst time posting. First of many?

imgur.com category @EarDwellingSpider

Kink first world problems

imgur.com category @darlingking

"It wouldn't hurt to knock first, you know?"

imgur.com category @[deleted]

The first of many

imgur.com category @Stinging__roger

Who's first? ;P

imgur.com category @prawnfarm

Another kiss, first.

imgur.com category @chrystaltwist

Spanked first!

imgur.com category @Elvishgirl

Vina's first milking was over a year ago. The life has been good to her.

imgur.com category @automat1111

[f] first time trying to get milf milk.

imgur.com category @xxxandi

Very first day, wish me luck...

imgur.com category @inchworm03

I didn't know it'd end like this when I first bought this toy for her....

imgur.com category @HisWifey01988

Got my first tease n denial blowjob today, it was so hot to watch her pull up pants and giggle saying it keeps popping up and down in there, got to go to work

imgur.com category @lukas0maximus

19m. First 6 hours in...

imgur.com category @Imlogang

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

Bought my first cage 6 months ago. Quite the "downgrade"

imgur.com category @incognitochastity

The point of no return, my first day in chastity!

imgur.com category @SissyKai

After my first ever experience switching, returning to 24/7 lock up is so bitter sweet :-)

imgur.com category @Doormat_Loser

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

imgur.com category @THINGSTOPLAYWITH