Jizz

Stop playing with that, you'll never get out without the key.

chastity

don't be mean: let them play

chastity, keyholdercaptions, xxxcaptions, Sissyperfection

Day 2 of being locked up. Realized how hard it was to wear it at the gym. My girlfriend gave the spare key to her sister for safe keeping, which is pretty exciting. She enjoy showing it off to her yesterday and even let her play with me to see how hard I

chastity

Wife's away. I'm not allowed to play. Couldn't be happier.

chastity

Verify me! Locked until PA piercing this Friday or Saturday... So looking forward to long term play I can't escape from... [8in.x6in.] I want my boyfriend to almost never let me out, I am so excited!

chastity

There's a certain feeling you get when you realize the cock in the cage can get bigger than the plastic one you're playing with.

chastity

My cage & pacifier for scale; staying diapered and chaste while my gf plays this weekend :)

chastity

Well.. Finally locked up by my other half after a year of 'playing'

chastity

Is this club exclusive? Or can we play here too...

chastity

4 weeks without playing with [m]yself

chastity

The only gift I didn't get to play with on Christmas

chastity

Can Never Play When the Queen is Away

chastity

Mommy let me play dress up!

chastity, SissyChastity

New device to play with...

chastity

While the key holders away boys will play.

chastity

Locked clit and about to play with my hole

chastity

Cages and leaking from prostate play

chastity

Just a lazy Saturday locked up! Should I unlock and play?

chastity

Blueballed from watching ruined orgasm porn all day. Had to stop myself from playing with myself somehow.

chastity

Aftermath of my play session. Finally fit the largest plug of the set!

chastity

Wanna play with me?

chastity

Two ways to play

chastity

Locked and ready to play

chastity

Just playing around with a little device I got yesterday.

chastity

Safe and sound. Not much to play with

chastity

Getting ready to play ;)

chastity

Just playing oblivion waiting for goddess to get home

chastity

Little guy wants to come out and play

chastity

Locked back up and decided to style my hair. All I need now is someone to play with.

chastity, Sissies

Passing the time playing spiderman

chastity

It took some convincing to get my SO to play along. I think she’s got the hang of it.

chastity

Been playing too much lately.. Need some control

chastity

Update: Uncaged for day 45 (my bday) for 2 days of free play including a creampie eating. Now back in for 45 more !

chastity

Waiting for the wife to come home & play.

chastity

Frustrated playing ga[M]es

chastity

This is the most play I’ve had in a while :)

chastity

Relaxing playing Anthem as the wife is getting her bbc fix

chastity

When Wife is away, Husband plays..... sort of.

chastity

Told not to play with myself when my girlfriend is at work.

chastity

Day 8 of 79. 24/7 since I got the new cage. Goddess has plenty of play dates scheduled though! Glad my tiny useless cock is locked up ?

chastity

mistress play time

chastity, Femdom

Anyone wanna play?

chastity

Roommate out of town. Wish I had someone to play with.... ?

chastity

Day 16 and escaping for a shower! Edged last night in the cage. I nearly came from her playing with my nipples, then again with my balls. Not from direct contact with my cock... First time that's ever happened in my life! Has that ever happened to you?

chastity

My new device arrived today. Already playing with it.

chastity

All work and no play makes Jack a horny boy...

chastity

Sometimes when I’m locked up I like to put on a strap on just to have something to put my hands on and play with.

chastity, gonewildchastity

No playing on this vacation

chastity

First cage has arrived! Now to find a willing keyholder to play with...

chastity, gonewildchastity

Day 7. What are some games I could play while locked up?

chastity

App controlled prostate massager for when Mistress wants to play

chastity

Nothing better than two bottoms playing together

chastity

Sissy Locked Up By GF And Ready To Play With His New Toy (Twitter: @AppreciatorChad)

chastity

Freshly showered, plugged, ready to play and please.

chastity