of course, a boy should wear jeggings. They make your body look super girly, make your legs look super dainty. Its all I wear, better then those bulky wide leg pants that always get in my way and constantly pulling them up.
You can but wont your manparts be kinda obvious. I mean I worry bout cameltoe but come onnnnnnn
I have two pairs of jeggings and they are really comfortable.
Enjoy wearing them you'll feel so good!