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It sucks to be me.

It sucks to be me.

Nice

Nice

Yes, yes, yes and I suppose so.

Yes, yes, yes and I suppose so.

Oh yeah.

Oh yeah.

I’ll bet she’s done worse than I can imagine.

I’ll bet she’s done worse than I can imagine.

Oh no, not that!

Oh no, not that!

There’s an incentive.

There’s an incentive.

Payback is … you know.

Payback is … you know.

Chaste Bob’s Orgasm Denial Journey turned 1 today!

Chaste Bob’s Orgasm Denial Journey turned 1 today!

Tell me more about the rewards.

Tell me more about the rewards.

I don’t know what to say.

I don’t know what to say.

Why don’t I ever get invited to these weddings!?

Why don’t I ever get invited to these weddings!?

Got that right!

Got that right!

Another one of my captions, reposted from imagefap.com by femdomarea,

Another one of my captions, reposted from imagefap.com by femdomarea,

Points of Intrigue for CB6000

Points of Intrigue for CB6000

chastebob.tumblr.com/post/54725370768/

chastebob.tumblr.com/post/54725370768/

Yes it does.  Chastity device added in Photoshop

Yes it does. Chastity device added in Photoshop

This works too.

This works too.

Sounds like a plan to me.  Chastity device added in Photoshop

Sounds like a plan to me. Chastity device added in Photoshop

Another one of my explorations into the potentially delightfully

Another one of my explorations into the potentially delightfully

I know, I know ooooohhh I know.

I know, I know ooooohhh I know.

Especially nice on a hot summer’s day.

Especially nice on a hot summer’s day.

She’s doing her homework after you asked her to be your

She’s doing her homework after you asked her to be your

Ed looks happy to get whatever he gets.

Ed looks happy to get whatever he gets.

OK, I know it isn’t the same bouquet, but work with me

OK, I know it isn’t the same bouquet, but work with me

chastebob.tumblr.com/post/54317251327/

chastebob.tumblr.com/post/54317251327/

The question none of us wants to have to answer.

The question none of us wants to have to answer.

Yes, I can see her too.

Yes, I can see her too.

See other caption of this same model a few posts back, for the

See other caption of this same model a few posts back, for the

A Woman's Guide to Chastity Security

A Woman's Guide to Chastity Security

chastebob.tumblr.com/post/53949882334/

chastebob.tumblr.com/post/53949882334/

This is what happens when revenge is served hot.

This is what happens when revenge is served hot.

Subtle teasing.  Chastity device added in Photoshop

Subtle teasing. Chastity device added in Photoshop

That’s the deal, isn’t it.

That’s the deal, isn’t it.

Still better than Hercules’ labors.

Still better than Hercules’ labors.

So that’s what that meant.

So that’s what that meant.