Cowgirl urethral torment

I started by sitting on him. I skip the small dilators and first one is 13mm. His hole isn't ready for this at all. It's not big enough. It'll only go in short. It doesn't matter, I still want to give him a hard time. I'm gradually working my way up to 15mm. That's really too much for him. I've got to push pretty hard for a long time. I can see him suffering. I'm giving him his biggest reward. My thin fingers. I'm trying to get my whole ring finger in. Unfortunately, he's still not ready. So I still have to train him properly. I'm trying to insert one finger at a time. I want him to come on my belly. We're turning around. I'm scratching and finger-fucking him. He comes with my pinky inserted and I have to work to keep the cum on my belly and not leaking onto the bed. He tells me his penis hurts when he pees until the next day. I have no problem with that, so next time it will be even harder.