Geordi had his creepy relationship with hologram Leah Brahms.
That episode where Wesley zings Geordi "At least I don't get my women on the holodeck!"
That's like a double zing, lot of truth to it and more so coming from Wesley of all people!
Picard had a pretty long list, but he was more discrete and classy than Riker so people probably wouldn't categorize him as a skirt chaser.
But in the spirit of the thread, going with assumptions regarding extras, Ben the bartender. Managing to pull a bluff with a 8 10 jack and king showing, that man could talk his way into Fort Knox nonetheless a woman's pants.