Here's a first go at specifics for my 'Ale & Wenches' rule from my Cinder house rules. I'm not entirely satisfied with these rules, but I can't quite put my finger on the problem.
Under my draft Labyrinth Lord house rules players can opt to earn some extra XPs by carousing. At the beginning of a session if a PC is hanging around Ye Olde Village Inne with nothing better to do, they can roll 1d6 and spend 100gp times the roll on liquor and/or lechery. The character gains experience equal to the gold spent. The d6 x 100 standard applies to villages only. A PC could travel to a town or city and debauch much more efficiently. Towns are worth d8 x 150 gp/xp and cities d10 x 200. The city of Hautville is worth d12 x 250 owing to its extreme wickedness. Carousing occurs at the beginning of a session and normally only characters that ended their last adventure in a town or city can take advantage of the bigger dice and higher standard of living sinfully. Thieves who are members of the local guild can spend 50gp more per pip if they so desire, while their friends can spend 25gp extra. Being mobbed up gets you first crack at the really good lotus powder, etc.
If the die roll is equal to or less than the character’s level, the result is a rousing good time and no harm done. Rolling above the character’s level indicates things got out of hand one way or another and the poor sucker must roll d20 and consult the chart below. If a character cannot afford the carousing they have rolled, they also must consult the chart and they only gain XP equal to half their money (though all the money is spent). Fellow PCs can chip in to cover a character’s bar tab, but henchmen only do so to avoid the imprisonment of the PC and then only if a loyalty check is successful.
[Update: I know use a straight save vs. poison to avoid mishap. Also I let people borrow to carouse as normal, but any money spent this way is owed to some local organized crime figure.]
1) Make a fool of yourself in public. Gain no XP. Roll Charisma check or gain reputation in this town as a drunken lout.
2) Involved in random brawl. Roll Strength check or start adventure d3 hit points short.
3) Minor misunderstanding with local authorities. Roll Charisma check. Success indicates a fine of 2d6 x 25gp. Failure or (inability to pay fine) indicates d6 days in the pokey.
4) Romantic entanglement. Roll Wisdom check to avoid nuptials. Otherwise 1-3 scorned lover, 4-6 angered parents.
5) Gambling losses. Roll the dice as if you caroused again to see how much you lose. (No additional XP for the second carousing roll.)
6) Gain local reputation as the life of a party. Unless a Charisma check is failed, all future carousing in this burg costs double due to barflies and other parasites.
7) Insult local person of rank. A successful Charisma check indicates the personage is amenable to some sort of apology and reparations.
8) You couldn’t really see the rash in the candlelight. Roll Constitution check to avoid venereal disease.
9) New tattoo. 1-3 it’s actually pretty cool 4 it’s lame 5 it could have been badass, but something is goofed up or misspelled 6 it says something insulting, crude or stupid in an unknown language.
10) Beaten and robbed. Lose all your personal effects and reduced to half hit points.
11) Gambling binge. Lose all your gold, gems, jewelry. Roll Wisdom check for each magic item in your possession. Failure indicates it’s gone.
12) Hangover from hell. First day of adventuring is at -2 to-hit and saves. Casters must roll Int check with each spell to avoid mishap.
13) Target of lewd advances turns out to be a witch. Save versus polymorph or you’re literally a swine.
14) One of us! One of us! You’re not sure how it happened, but you’ve been initiated into some sort of secret society or weird cult. Did you really make out with an emu of was that just the drugs? Roll Int check to remember the signs and passes.
15) Invest all your spare cash (50% chance all gems and jewelry, too) in some smooth-tongued merchant’s scheme. 1-4 it’s bogus 5 it’s bogus and Johnny Law thinks you’re in on it 6 actual money making opportunity returns d% profits in 3d4 months.
16) Wake up stark naked in a random local temple. 1-3 the clerics are majorly pissed off 4-6 they smile and thank you for stopping by.
17) Major misunderstanding with local authorities. Imprisoned until fines and bribes totaling d6 x 1,000gp paid. All weapons, armor, and magic items confiscated.
18) Despite your best efforts, you fall head over heels for your latest dalliance. 75% chance your beloved is already married.
19) When in a drunken stupor you asked your god(s) to get you out of some stupid mess. Turns out they heard you! Now as repayment for saving your sorry ass, you’re under the effects of a quest spell.
20) The roof! The roof! The roof is on fire! Accidentally start a conflagration. Roll d6 twice. 1-2 burn down your favorite inn 3-4 some other den of ill repute is reduced to ash 5-6 a big chunk of town goes up in smoke. 1-2 no one knows it was you 3-4 your fellow carousers know you did it 5 someone else knows, perhaps a blackmailer 6 everybody knows.