"Half Jack" refers to a person who is gender confused, and possibly considering sex change surgery. A person who either feels that they are of the wrong gender, or that they are half male and half female.
Mary was really into Tom at the party last night, but she wasnt aware that he's "Half Jack" and had no interest in her.
Either during sex at orgasm or while your 'one night stand' is asleep.
the idea is you cum and shit all over your partner at the same time giving you and your partner your weird sexual jollys. if your partner is asleep then you do the same process without waking her up and leave her alone in her house/flat, so she wakes up with shit and cum all over her body, make sure you give her a fake name so she cant track you down.
Ex1 - dude i was banging this chick lastnight and she asked me to double jack all over her face!
Ex2 - hey i had this one night stand lastnight and when she was asleep i doublejacked all over her body and i went back home!