keyholdercaptions

I just love the sound

keyholdercaptions

34

DRIP DRIP DRIP [chastity] [anal] [permanent]

keyholdercaptions

61

Just a quick signature giving me control over that locked up nub for a whole year. Little freak, youre drooling in anticipation

keyholdercaptions

37

No sign of a release

keyholdercaptions

83

They are all just colleagues. Have fun on your first day at work!

keyholdercaptions

72

Your key gets more action now

keyholdercaptions

66

Would you beg her to take your key?

keyholdercaptions

22

She is experienced and knows when the fun starts!

keyholdercaptions

73

I'll make your clitty go crazy

keyholdercaptions

15

Drinks are on you I guess

keyholdercaptions

22

St. Chastity Boarding School 101

keyholdercaptions

50

It is no longer your decision when it has been long enough!

keyholdercaptions

299

are you happy about how things turned out?? - original mcap_op caption

keyholdercaptions

15

Her bull gives her all kinds of ideas.

keyholdercaptions

67

Thats now how it works...

keyholdercaptions

31

Think about me

keyholdercaptions

61

Humiliation and submission at University Part 8 - image credits to tugmy2nipples

keyholdercaptions

37

.. but first I will lock you up

keyholdercaptions

11

Who's up for a spring cleaning?

keyholdercaptions

120

Focus

keyholdercaptions

100

which hole do you want to see?

keyholdercaptions

55

Dumb Question. (Trans)

keyholdercaptions

28

Youd just strain against your cage if you saw her perfect tits!

keyholdercaptions

294

Did you have a promise to her that would be forever? Well, now she is the keeper of your promise!

keyholdercaptions

134

Humiliation and submission at University Part 3 - image credits to tugmy2nipples

keyholdercaptions

23

I love treating and training my pets.

keyholdercaptions

24

Humiliation and submission at University Part 10 - image credits to tugmy2nipples

keyholdercaptions

30

You will be throbbing in that cage

keyholdercaptions

109

Some dates cang get really odd - original mcap_op caption

keyholdercaptions

12

How much do you crave my cock?

keyholdercaptions

21

Humiliation and submission at University Part 9 - image credits to tugmy2nipples

keyholdercaptions

62

Would you let your keyholder do this?

keyholdercaptions

99

It was even more humiliating when I realized that they'd sent her BF out to buy epoxy for my cage!

keyholdercaptions

54

New roommate agreement

keyholdercaptions

53

You asked for a sexy picture and landed yourself an extra 3 months of chastity.

keyholdercaptions

26

Nothing manly

keyholdercaptions

11

The never cheating way - original mcap_op caption

keyholdercaptions

50

Humiliation and submission at University Part 11 - image credits to tugmy2nipples

keyholdercaptions

60

Beach date pickup

keyholdercaptions

10

You're not just handing over the keys, you're handing over everything!

keyholdercaptions

25

EFFORTLESS [chastity] [femdom] [permanent]

keyholdercaptions

137

Step out of your comfort zone!

keyholdercaptions

62

OBITUARY [chastity] [permanent] [exposure]

keyholdercaptions

38

Let the games begin

keyholdercaptions

56

It's all fun and games

keyholdercaptions

90

Regular checks are needed even in a cage with spikes!

keyholdercaptions

25

INESCAPABLE [chastity] [femdom] [dildo]

keyholdercaptions

26

Your girlfriend has a knack for keeping you in line!

keyholdercaptions

56

Come on, give in, you know you want to

keyholdercaptions

24

Keep Holding On

keyholdercaptions

22

A small price to pay

keyholdercaptions

45

Humiliation and submission at University Part 13 - image credits to tugmy2nipples

keyholdercaptions

12

52 - A very bad puppy [Femdom] [Hentai] [Boots] [Chastity] [Humiliation] [Slave] [Petplay] [Group]

keyholdercaptions

13

Humiliation and submission at University Part 4 - image credits to tugmy2nipples

keyholdercaptions

21

A tiny cage with spikes will have you beg indeed.

keyholdercaptions

13

Love when "tuff" boys finally submit.

keyholdercaptions

75

Weren't you listening at the time?

keyholdercaptions

63

Humiliation and submission at University Part 12 - image credits to tugmy2nipples

keyholdercaptions

28

Humiliation and submission at University Part 1 - image credits to tugmy2nipples

keyholdercaptions

12

Reasons to (not) cheat - original mcap_op caption

keyholdercaptions

41