There is at least one doujin that does this.

He's just going to make Miyuki suffer some pain everytime they do it.

Is she crying that the cum would spill out?

True said:

Is she crying that the cum would spill out?

No. Now that I've translated it you can probably make more sense out of it.

His power is not healing, is more like taking damage into himself (help when he can regen), beside this ability got a penalty where Tatsuya will feel the pain of damage part, which, oh god, where in hell that pain will transmit in the first place?!!

nckeo said:

oh god, where in hell that pain will transmit in the first place?!!

Nowhere. It would null pointer exception. Well played, dude.