I never wrote a walkthru since I 'thought' I'd answered all these questions before. After searching through the 23 pages of comments and all my emails I realized I had... but to multiple different people. So... I'm compiling all the info here for a Walkthru, Medals, and Hidden items.
----- Walkthru -----
You can get all three endings and every piece of clothing in one game but it's not gonna be as much fun as 3 games. Here's how I did it:
I started a new game. I did the Oral-Sex path first, buying only coffee, crickets, and spicy soup every day and paying off any debt immediately. Sell Alcohol at the Pussy Club to raise your Rep. until you can borrow 3000. I borrowed 3000 from the pimp ONCE to buy the blanket and Temple upgrades giving +1Hr and +10% money. Buy every Bridal Item in the Night Market. Pay to have the vendor look again to find them faster. Each one increases your BJ offers.
*IMPORTANT* I did NOT move the Pussy club reputation forward. Keep the pimp at the 3000 baht offer but don't take it again. Also, buy NOTHING (no items or temple upgrades) except Makeup and food!***** I went through all 30 days and had found all the Bridal Clothing Items and 21,300 Baht.
Buy the plane ticket home to use up all 20,000 Baht. You want to be close to 0 Baht for the Bondage ending.
Next I moved the pimp forward to the 5000 baht offer. Borrowed it and spent it all on items and temple upgrades, every day saying NO TO ALL SEX and buying all the food everyday to increase my debt. Every 5 days I borrowed another 5000 baht and spent it all, never paying any debt off, obviously. I repeated this pattern for around 12 days before I got the Bondage ending. Then I actually kept myself in debt for ANOTHER 18 days (60 days into the game now) just to get all the Bondage clothing pieces as well. You seriously could stay in debt forever by repeating this cycle: borrow 5000 baht every 5 days and buy all the food every day and do NO sex at all. (and DON'T move the pimp forward or you lose the 5000 baht option)
Next I aimed for the Priestess clothing and that is easy, Just say YES to all sex and buy all the makeup every day, and visit the temple shrine every night. took me 154 days total until I had all the Priestess clothing. I was Priestess level 12, had donated 624,774 BAHT to the temple, and also had 11.5% of the SPC (230 shares) purchased.
----- Alternate gameplay idea from: lrdjms -----
First off is bondage. The trick to getting the bondage ending is that you have to get into alot of debt, and you have to get into it fast. Your general day should include saying no to any sex offers, followed by blowing money on clothing, makeup, the gods, everything aside from food and drink. at night go to the pimp's place and click the "sell alcohol" button, this will increase your reputation.
eventually the pimp will offer you a loan of 5k, take it and blow the money, after the time alloted for the loan has passed, he will offer you the 5k again. Repeat process until you are completely in debt. At this point you should have no trouble getting the bondage ending.
The bridal ending is a bit trickier, it's easier to do the bondage ending first, then after you get that ending, have sex with everyone as much as you can to get more upgrade points. once you have about 300 or so, go to the main screen and click erase data. This will erase your progress but keep your upgrade points. To get the bridal ending, you need to survive 30 days without having vaginal or anal sex, meaning only bjs. only accept people that ask for bjs, the first day you should spend money on the mango milkshake, crickets, and either the first dress or the wax and bleach your entire body. Every day after you should limit the money that you spend to crickets, mango milkshake, and slight increases to the gods for increased sexiness, the client one and the god of wealth. IMPORTANT, whenever the dude shows up to offer to sell you bridal items, buy them( with the 300 or so upgrade points you have from the previous game). I cannot stress how important this is to the bridal ending, as if you don't get asked for bjs your going to go bankrupt and be forced to do bondage. if you follow this and spend your money on slight upgrades you will make it to the bridal ending.
Also, for people that don't know, if you want to get the "special" sex positions, go to the pimp's place, and sell alcohol, after you've done this enough then misty will talk to you about these new sex positions.
Hoped that helped people and btw this is a great game.
----- Medals -----
Average Workday: Work 9 hours each day. You must have a day where you make less money than your costs for that day. You will be given 1 more hour to work. Buy the mattress and pay the Temple god of Wealth to get the other 2 hours.
Upset Stomach: Buy the spicy noodles each day and eventually you'll get sick from them.
You Go-Go girl: Sell alcohol at the Pussy Club to increase your Rep until the Pimp offers you a spot dancing at the club.
Illicit Access: Use a confidence booster to unlock a sex act. Easiest at the start. Just buy a Pina Colada to gain 10 Confidence and unlock the next sex act.
Have a gay old time: This can be very hard to find. You need to unlock the anal sex, have the penis, and have anal sex with an old man. It's a random chance so may take awhile.
Bonus Overkill: You need to buy (or have activated) all the cosmetics and food items that give bonuses in one day.
Endings: see the walkthru above
Low self-confidence: You need to try to haggle a price and fail, then accept the lower price 3 times in one day.
Fully booked: You need to have a customer every hour of the day.
Meretricious Pulchritude: Have all the cosmetic items active in one day.
Millionaire: Earn 1,000,000 Baht throughout the course of the game.
Average American: Be $15,705 in debt.
----- Rare Items -----
There are 3 rare items in v.1.18. There is less than 0.5% chance of finding a rare item.
Cosmetic Kit: You gain the Makeup bonus everyday for free. Chance: Every day you buy makeup.
Hair Flower: You always have 100% Freshness. Chance: Every time you change a clothing item on the beach after having sex to increase your Freshness level.
Cell Phone: You can call a Client each day. Chance: Every time a client appears for sex.