Updated; everything with consent.

I like to offer my boyfriend with other guys online and share his nudes with them, basically cuckold but without the humiliation part. Usually I jerk on cam with other tops to his pics.

The thing is that most of the time he's not into cuckold, so there's no way to do it in real life, we only enjoy that when we both (specifically him) are horny enough and he allows me to do it.

Any advice? I don't feel like I should encourage him to do something that he's not comfortable with, but some very specific time he really is. So I'm confused if he thinks that doing so would imply something romantic or idk. I just know that I get hard when others jerks off to my boyfriend hairy ass.