I too have never seen a telescoping gage with flat ends; perhaps you are thinking that they should have a full radius, when in fact, they are radiused to suit the smallest hole measurement in their range size. Another thing is how you are using it; the procedure is to get it inserted in the hole at a small angle, then snug the lock up and rock it over center and remove it for measurement, then measure it with a micrometer, not a caliper, which can introduce small errors into the measurement.
One might think I do not give enough credit for others not knowing how to use a telescoping gage, but I had to teach at least two employees to do it in spite of the fact that they supposedly had apprentice training. You cannot feel around in a bore with the gage after the first "over center", the effect would be to cause the gage to telescope somewhat and lead to an undersize reading.