Complete noob, but I have observed that the biggest influences on my best workouts and "stretches" and so forth result from two basic things, especially relating to stretching in general.
The more heat, the easier it is to stretch. Period. High heat has a dramatic effect on how much one can stretch with the same amount of given force. As you raise the heat, you can either stretch more with the same effort, or you can stretch to your normal "max" with a lot less effort.
Constant stretching versus "reps" of stretches leads to much better stretching session overall. (Provided you do so with a grip, which I use, or device, which I haven't, that doesn't restrict blood flow too much.) I only stop stretching when I sense any form of numbness or coldness, otherwise I keep stretching throughout that part of my workout. Instead of stopping for "reps" when "fatigued", I simply change angle of stretch while never reducing or stopping the stretch. Instead of "flapping the dick around" to keep blood flowing or to get it going again, I continuously kegel while stretching to keep the blood moving.
My two cents.