h2g2 The Hitchhiker's Guide to the Galaxy: Earth Edition

This is an excellent and informative (and not just for you boys, girlies too can suffer from zipping the nether regions too).
But, I have to say this, I think that the advice to zip then button is wrong. My credentials for saying this are many years of dressmaking have made me intimately, boringly so, acquainted with zip fasteners.

The fly-zipped trousers are constructed is the same for male and female garments. The zip is separated from the flesh/underpants by a flap (the technical name for which I have temporarily forgotten... not to worry, the name will wake me at 4am). When the button (or hook) is fastened, the trousers are so constructed that the zip is now in a position to be zipped without putting strain on any of the teeth ie. the two sides are together, but not joined. It is important when zipping that the 2 sides are as close as possible without overlapping and perfectly parallel. This is one of the reasons trousers (and most skirts) have the button and zip. (the other, for zip trivia freaks is to stop it coming undone during wear).

I would recommend this:
1. make sure that the flap of material is properly aligned (ie. flat and behind where the zip will be)
2. close the button / hook
3. slowly close the zip, pulling it upwards, not outwards.

hey presto: safely zipped.

Definitely agree with buttoning first.
You've got to get the two sides of the zip as close together as possible before zipping, then you only need a tiny amount of force.

Girls have this problem too? Jeez, those must be some TIGHT pants!
(sorry for shouting.)
Please feel free to wear these troublesome pants in public as often as you possibly can.

Some of us not blessed with the Barbie bod may have a similar problem with not quite so important parts, but nearly as sensitive.....

Yes, some of us females have caught tender flesh in zippers - or how about neck-hair or your entire pony tail in the zipper at the back of a dress? Explain THAT to your mother after a date!