Already mentioned by others but... I have gotten foleys in when urologists could not and was the "foley queen"
It's all in the angle - which can vary with the patient. What you want is straight in through the prostate.
Hold the base at the pelvis and form your fingers around it somewhat firmly - never had anyone complain of any pain with that. You are actually holding the "shaft" firm so it cannot bend and I use my fingers up the whole shaft to keep it all straight and from bending.
When the foley hits resistance, you will feel it with your fingers. Squeeze with the fingers to form it's path so it can't bend. From there it becomes a feel like doing IV starts. But, you will try to get the catheter in and hold back right at the resistance periodically waiting for the "spasm" to release. Sometimes it spasms and makes the "wall" worse. You have to keep the tip of the catheter at the "wall" to feel when you might get any opportunity to go through. When it goes through, it might be very tight but you are using the squeezing of your fingers to keep everything from bending and go through. Once you are in, you should be able to get through. It's getting in. Sometimes a med before hand will help with pain and relaxation and sometimes lidocaine helps.
Sometimes you might be standing at the bedside for a few minutes or so trying to get your timing, trying to get the patient to relax and breath, etc. I have only had two that I couldn't insert and I think the reason is because the people that were trying before they asked me caused so much irritation that it wouldn't relax and the patient was in pain. I am pretty sure if I was the first one that tried, I would have gotten in. It's so hard to explain. It's easier to show. Maybe I can sell videos??? Here I am constantly thinking of a way to make money other than FLOOR NURSING.