Ok Video don't work! But it don't matter! I do get the point.
I think I know what you are talking about. As DLD said try to get 90% erection, from there,with one hand hold the base and balls too with L Wedge grip and press! to start your jelq as deeper as possible, and with the other apply the best Ok grip for you that is comfortable and you actually feel blood flowing up to your head (the best is to really feel the pressure of the expasion all the way up and really purple-ish glans)
If skin keeps been a problem, do this!
I used to place a towel somewhere(it has to hold itself,find the way)like a towel ring. Everytime I felt skin was a problem I would pull extra skin from the bottom of the scrotum and hold it while jelquing upward. (after my penis got bigger extra skin problem it didn't bothered anymore
This could cause pain on you penis as you jelq upward, if you pull too much or from the wrong spot.
I also reccommend this specially for upward But to the side jelqs (skin pulled to the left jelq to the right,skin pulled to the right jelq to the left). If you need more help let me know I could upload the video explaining.