Once you have a high enough Lewd fame in Bareshade (I had 3), you'll be able to click on the alley in front of the watchtower. If you need to add to your Lewd fame, go to the Track, and take breaks until Gunnar wants you to suck his dick. Doing that increases your Lewd fame.
Peoblem for me, i dont get no option to even suck him off since 1, i got lewdness at a 1 fame only n i need his forgiveness to even progress to northcrest, how can i raise lewdness if the whole town sees me as a high regarded personel?
Not even a fucking opt to fuck barkeep or the caravan guards