AFAIK, Thugs are the only ones who can even giver her the D, Goblins only give cunnilingus, and guards are the only ones who initiate a handjob (you can initiate it on others)
Quickest way to getting fucked is spanking, or secondarily whatever weakness you've built up her sensitivity to. spend a while stomping ass and raising order for more cash per day, buy the accessories that lower whatever, get the sex skills (kiss specifically, at least) Buying accessories also raises the charm stat, so yep, money grinding.
Find a thug. Begin by releasing butt pleasure, kiss him until he gets the blush marks, use the dodge skill over and over (the lewd moves don't miss, and you don't want to go down too quick because then you'll be left waiting on them to get their asses going without your own moves) until he gets those pesky clothes off and spanks Karryn enough, and if you've gotten her dirty enough as soon as she's wet (probably around 60-70% pleasure) it'll be go time.
If there was enough time spent dirtying her up, all the hearts should fill up on their own after you bring butt up, but it's probably a good to raise cock a bit too. I'd actually say avoid raising others so they don't use less-pleasurable moves on her.
I had 2 accessories that reduced sex resist iirc, but after getting all the traits i could, and going about this route, it seems 100% surefire to happen the turn the thug was aroused, and karryn was wet. The bar seemed to frequently have a 5 round fight, where a thug was in rounds 1/3/5, with annoying rounds 2/4 without them and only regular prisoners.
Of course, if you bring up her fatigue even just 20-30% she'll start to become weak and have a hard time not getting bopped down by thugs and then you have to wait for them to act stupid and poke her butt and tits and take forever to get anywhere, above 50% and you'll spend more time on the ground getting fondled than getting any good sex going on.
