It's the wrong way when you frequently interupt the process with the question, "Why am I doing this?" Funniest fuckin' comment I ever heard in my life.
Some general tips (no pun intended): I'm probably a little older than most of you. I learned the hard way (aaarghh another pun), that you have to be gentle with your penis because you can injure it. This is especially true if you experience a very large change in length like me. Guys can even injure their penis's if they are asleep and roll over on them while they're erect. Putting great pressure on it while using your hand can also be bad. This may result in what is called Peyronies disease. Actually it's not a disease, just an injury that will make it bend in an odd and uncomfortable way when erect. I had to have surgery which left uncomfortable scar tissue. I believe they now have more state of the art techiques for fixing this problem. Here's a gentle way to get some relief: Use a prohylactic that has K-Y or Albolene in it (Don't mix the two ..... One is water base the other is like an oil). If using K-Y put a little clean water in with it. Experiment with this. Natural vaginal lubrication isn't as thick as K-Y. Before putting the prohylactic over your erect penis, put some straight K-Y on yourself so you can easliy slide into the prophylactic. Put a soft lined winter glove on the hand you use. You can also use thin foam rubber. This isn't too far off from the feeling of a vagina and I think it's worth the fuss. Hope this works for you. Take care of that love worm. Best wishes to all.