A winky face denotes playfulness.
It is used as a way to convey the playful sentiment in a medium, such as text, where emotions can't otherwise be displayed.
Depending on the context, it can be flirtatious, but usually denotes joking.
The winky face is used to imply to the opposite sex (or same if you sway that way),
that your keen as a bean for their Dick or Vagina!
Jess: Chris asked me if I was free tonight
Chloe: did he put any emoticons?
Jess: Yeh he put a winky face at the end of the sentence
Chloe: HE WANT'S YOUR VAGINA!!
The face one makes when they want to have sex with someone. Mostly happens when drunk but can be when sober and just extremely horny. A face that says it all, no words are necessary....the face (especially the eyes) say "I want you to make love to me. NOW"
After Danielle had her tenth beer she started to make a seductive winky winky face at Anthony.