This can be taken too far. Try not to stare at his hands and say “Nice strokers!”. It could be taken the wrong way.

“You’d look good on your hands and knees under my foot.”

You’re joking with that NSFW tag, right?

It’s text. Unless your boss is actively reading from your screen or it gets you so damn hot you can’t contain yourself, it’s safe for work.

Ruling rule

Tfw no one notices how good I look in a collar and leash