3.
For starters, you can always work in a Café, with no requirements. It pays 10 quid per hour if I remember correctly. There are also odd helping jobs you can get while knocking on houses in the Residential Area and on Danube Street. You can also get a job at the Docks. To really start earning some serious cash in less than pure ways you need to raise your lewd stats and skulduggery. Once you've discovered the Brothel (go to The Strip Club first and be refused entry and someone will tell you about a suspicious building on Harvest Street) you get work there as a dancer/stripper (your tips will depend on your dancing skills - these are raised every time you dance or when taking lessons at the Dancing Studio + exhibitionist charms - taking off clothes while dancing). With enough promiscuity (lv 3 or higher) and good luck a spectator may ask you for a session in a private room, where you can whore yourself out. Your earnings will depend on your Math skills and the price is negotiated beforehand, so your further actions 'in bed' will not affect it, though you may get some extra tips during the sex (payment-related tattoos/body writings and sexual skills help a lot) or you can steal money from your john with enough skulduggery skills (it's easier to steal from them if they're sexually excited on the verge of cumming). Lv 2 Promiscuity will allow you to work in the Brothel's gloryhole, which while not very rewarding financially (between 5 to 20 quid per trick) is a great way to increase your sex and promiscuity stats in a safe manner. All acts, no matter how vanilla or dirty will only cost you fatigue, but no stress or trauma - quite the opposite, the lewder acts you willingly perform there, the more liberating they are psychologically, thus restoring your control, self-worth and reducing stress, trauma). Each higher level of Promiscuity will allow you to initiate more and more daring acts (jerking off, oral, boobjob - provided you have breasts big enough, vaginal anal; from passive/suggestive (tease/rub) to active/assertive (straddle/envelop)). It also opens up options for whoring outside of the Brothel or having free consensual sex. A week or two of frequenting the Gloryhole after school and working there till almost exhaustion will make a confident and skilled, confident slut out of your character. Do not forget to take a shower before leaving the Brothel and use the Dressing Room to change into something unassuming to reduce Allure avoid being molested/raped when returning home.
Finally, once your fame as a prostitute is high enough, as well as your promiscuity and deviancy, Briar the Brothel owner will propose a special Friday show, where you can earn really good money: Flirt'n'Fuck (Promiscuity lv 4 or above) for 600 quid, Schoolgirl/Schoolboy Gangbang (Promiscuity lv 5) for 1000 quid and Pig Mating (Deviancy lv 5) for 1500 quid. It will take some time to attain such level of Deviancy, but you'll get there eventually.
The Strip Club is a soft version of the Brothel, with proper security preventing any non-consensual encounters. You will first need to obtain a fake ID from Briar in the Brothel, which will cost you 500, but with enough dancing skills and proper attire, the investment will quickly pay off. You can make decent money working as a lewd bartender, without even having to have sex with your clients.
You can then win your bread as a petty criminal, starting with breaking into school lockers to take other students' lunch money, then committing burglary in the Residential Area, pick-pocketing outside the Strip Club, rummaging through Landfill, stealing while having sex, etc. The rewards are not that rewarding I've found, except for blackmailing Leighton and getting a luxury watch from him to keep your mouth shut.
You will also get financial rewards for winning school competitions (Lichen exhibition, Penis Measurement Survey, Math Competition)
4.
Generally speaking, the masochistic trait rises every time the PC is in great pain and aroused as well. The best method I found so far is getting regular spankings from Leighton while detained after school combined with edging in the school Toilets before receiving the spanking, so that my PC orgasms from the actual ass whopping and is in such a great pain that they cannot act normally. This also increases the Willpower (being in great pain and/or orgasming). There are several stages of masochism and with each one the painful actions are transformed into Arousal more efficiently to the point that the Drooling Masochist will be cumming like mad while being brutally raped / gangbanged with limited impact on their Trauma and Stress levels. Once you're strong enough to withstand the spanking and remain submissive during the act (kissing or sucking Leighton's nipples), their reactions while punishing you will change from anger to affection to the point they will praise your divine beauty while slapping your butt and biting your breast, eventually climaxing in their pants while giving you a spanking, which earns you a feat and humiliates the Head Teacher (although with no consequence whatsoever on their subsequent behaviour towards you). Their antagonistic relationship should be further expanded, with Leighton becoming one of the PC's love/hate interests.
Once you've brought enough antiques (10) to Winter's Museum, they will propose a medieval torture device demonstration with you partaking as a villager brutally interrogated by their landlord. The demonstration may be repeated agein and again, but only once a weekend when the Museum's open. The effects should be similar to Leighton's spankings, but it will take longer to explore enough locations where antiques can be found (sewer system, Forest, Landfill, Lake Ruins, Orphanage, Temple, etc)
5.
As mentioned earlier, the higher the masochism the rougher the situations your PC may handle. Apart from Leighton's spankings and Winter's torture device, I haven't found any safer methods of controlled increase of the PC's masochistic proclivities and I'd like that very much (a BDSM club or relationship with progressive training/perfomance sessions).
6.
No, the third time you refuse to pay they will beat you up and take to an underground dungeon when you'll be subject to constant rape that may seriously damage your psyche. Of course you may recover from the ordeal (there are feats/medals given for that too), but so far I've found it's easier to part with 2 grand every Sunday, which is equivalent to one Friday special Brothel show and 4-5 dancing sessions ending in a private room.
7.
I've gone that route once and found that you can leave Eden's hut of your own volition, even with the Stockholm Syndrome: Eden trait acquired, but after a few days of absence they will start looking for you and eventually find you and take you back to the Forest. The Eden theme feels a bit uneventful at the moment so I hope it will be expanded in the upcoming updates.
