Tell him straight out that the talk is too far and hes being a dick.

Yes I agree, just say you let him win because you don’t want to hurt him keep it playful

I wouldn’t get physical, it could get out of control.

If it’s playing, I don’t think you should be attacking his most vulnerable part. Maybe launch a sneak attack instead.

I big no to your suggestion and no “fighting” contact with his head either. If you aim badly or he suddenly moves you could injure his eyes. I have seen the results of that. All could see in a friend’s eye was blood after being hit in the eye accidentally. Result- a few days in hospital, complete bed rest both eyes covered, not allowed to get out of bed at all, totally dependent on nursing staff. Sponge washes by staff. If you move one eye the other one automatically moves too. He had to have drops in his eyes at regular times. That’s why both have to be covered. Fortunately his eyes had been tested a couple of weeks before so the Eye Specialist was able to compare tests results. He lost 4 % of vision in that eye.

Bah, don’t muck around with the testicles. What you intend to be a slight rap could easily end up much worse

Don’t rap the nuts! They are way too sensitive and easy to hurt

Go sign up for a Muay Thai class, teaches defense and attack! Throw in a random head kick or check and block – blow his mind!

I wouldn’t go for the nuts, but I’m competitive and wouldn’t wont to lose so if you have the opportunity I would work on my strength so that you can give him a run for his money.

Do you have any games that you know you can beat him? It could be a card game or something similar

I agree with the other person who commented about saying you let him win lol

Just tell him you let him win because you don’t want to hurt him hehe

Child birth is a great equaliser!

Stay away from the nuts. That would overstep boundaries I would think.
Perhaps you guys could compete in things less physical.
If he always wins the play fights, then he is technically right. But that doesn’t mean you’re not better than him in other activities. So compete at something else you are good at, convince him to partake, and when you win in that, you then have the opportunity to joke trash talk too.
We all have our strengths and weaknesses. Discover what yours and his is and use that to your advantage.

Have you given birth to kids?
That’s one that usually keeps them quiet!