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Just be brave and always go for it: always put the penis ring on when the penis is not erect. First carefully insert one testicle, then the other testicle and then the penis into the ring. And don't overdo it - you shouldn't wear it for more than 30 to 35 minutes. Happy at the end, but also totally exhausted? Carefully remove the ring again - if necessary with the help of a lubricant.
Yes, it's true: size does matter. If you choose a penis ring that's too big, you won't get the desired effect and it might even fall off. If you choose a penis ring that's too small, it can cause health problems. Please always make sure that the penis ring fits tightly, but never uncomfortably or painfully.
You can determine the right size as follows: Loop a piece of non-elastic string around your scrotum and penis so that the ends of the string meet above the penis. Put the string on just tightly enough so that you feel a comfortable pressure. Mark the two intersection points of the string and measure the length to the millimeter. This length divided by pi (3.14) gives you the required diameter. But please don't use pi as a rough estimate - many people are way off the mark when it comes to the famous 20 cm.
Another tip: Measure on several days at different times, as natural fluctuations can occur. If in doubt, always choose the larger size.