Surprisingly easily actually! It’s the big surprise in all this to me really. But I tend not to think of it as humiliation, but teasing. I’m not saying things like ‘you have a pathetic little cock’, instead it’s a few things like dropping in the word, ‘little’ -‘let’s get your little cock out of its cage’
Most of all though it’s me telling him stuff while I play and edge him, whispering in his ear stuff like, ‘I wish you were bigger’, ‘Do you think this would feel even better if I more cock to stroke? Etc.
And simply looking at Tumblr and videos and me genuinely admiring the big cocks, ‘oh my God, look at that, do you wish your cock was that big?, He’s twice the size of you! That’s a beautiful big cock, I couldn’t even fit that in my mouth’
It’s also super hot to blame his caging and denial on his cock size, ‘Id never lock up your dick if you were as big as that’, ‘If you were twice this big I’d let you cum, but small cocks don’t deserve to cum, you know that baby’ kind of thing.
Also I don’t do it all the time. I tend to try it and if he gets hard or says something that indicates it’s hot, I go for it.
I hope that helps explain. The bottom line is we both love it… Not completely sure why but that doesn’t really matter!