As a precursor to making him swallow...  This is so easy.

Have some humiliation shirts made up.  A fun creative exercise...  A lot of fun at the t-shirt shop seeing the shock as you place your order or pick it up. Then, where them around the house and nonchalantly want to go out to the store with him, run errands, or go to a friend's house. He will likely panic a bit asking if you could or would change.  Just slip a short over the top. That way, you can tease him more while you are out.  "It's getting hot in here...  I should take my outer shirt off"  or unbutton your shirt a bit, so some of the phrase is exposed.  

Any boundary can be overcome.  Just give it time and teasing, and soon he will BEG you to cross that boundary!

Ladies... If you are still on the fence about femdom, just take the plunge.  It is so easy, and so rewarding!

Women...  Use his internet history to know what turns him on, and look for ideas. Men...  Let her review your history.  You're looking at what turns you on, so don't be a wimp by trying to hide it.

this is a great caption to teach you both how to think.

You can suck on a cock in his mouth to make him hard in his cage, while ridding his strap on making him feel like he's having sex.

Test his submissive resolve.  Don't just give it to him...  Make him BEG to suck your strap on, or BEG to have you own him

Clothed or unclothed, spend some time with him underfoot.  It conveys SO much!

A simple choice like this can serve as a challenge to assess where his allegiance is...  You or himself.  If he chooses wrong, you could Take his choice away.