My quick-start guide. This is for version 1.2.0 alpha2, available
here.
Step 1: go to your "Progress" tab. Go to "Income." Take out a loan for $25000 and use it to start an escort agency. Hire workers to fill out the roster. Don't bother with tweaking it any further, you'll get enough money just by starting the agency and hiring 10 workers.
Step 2: Go to the "Contacts" tab. Go to "find new contacts." Don't change any of the search criteria except for race, just start searching. You'll get 3 results per search, 3 searches per day. Add some contacts, I'd recommend starting with 4.
Step 3: Contact each person on your list and challenge them to games. Set the stakes to "be a sissy" and "have sex." Bet whatever it takes to get them to agree. I haven't lost a game of dice so far and the AI is pretty stupid, so don't worry about losing. You'll get them to agree to be a sissy and have sex with you pretty much straight up.
Step 4: Repeat step 3, but this time set the stakes to "agree to short-term stay in the dungeon."
Step 5: Inspect each sissy on your list, check their profile. Go to "Brainwash." You'll have one idea to add, start with the "you need to be brainwashed" option. You have no points to add to these ideas yet, that'll come later.
Step 6: The hashtag looking symbol is the "dungeon" option for the sissy. Click on this, it'll give you an option to put the sissy in a cell in your dungeon. Do this for all 4 cells.
Step 7: Go to each sissy in your dungeon and go back to their profile. You can now adjust their schedule. Set each one to do a fat-burning workout each day and to shave everything.
Step 8a: Visit the dungeon, stand outside of each cell door and pick the "have sex with the prisoner" option. This is the only way to initiate sex with a sissy in your dungeon. If you don't see any options to start sex, hit the spacebar.
Step 8b: To build up "deep throating," start with a face-fuck (not the blowjob). You can get there by selecting "top." Wear a condom at first, you want the positive karma for later. Face-fuck at full force, but watch their stat and back off when the gauge is almost empty. Keep the oral sex going until their pleasure meter is at full.
Step 8c: Hit "tab" to switch sex positions. Start anal sex, click on "top" again to get to it. Start slow and gentle, and ignore the fact that they'll be in pain very quickly. Click on "gape" whenever the blue bar of "anal endurance" is almost empty. You won't get them to a sissy-gasm the first time round, this is all about building up their endurance. Keep clicking "gape" whenever the blue bar is almost empty, eventually there will be a message of "gaping increased." Stop having sex when the "anal endurance" bar is just about empty.
Step 9: After repeating step 8 (a,b,c) for each sissy in your dungeon, go to "schedule." Set up your own schedule to include a full work-out each day. Include shaving if that's your thing.
Step 10: The "schedule" tab has "simulate days" on it. Start with just 1 day at a time, keeping a sissy for too long when they've only agreed to short-term stays will hurt your reputation a lot. Check each sissy's profile each day for their brainwash progress, being in the dungeon will automatically increase their "be a sissy" idea at a rate of 1 point per day (may not be consistent across all sissies). They'll all be in pain from the first anal sex so only practice oral sex at this stage.
Step 11a: As soon as each sissy has 5 points in the "be a sissy" idea, release them from the dungeon. You can do this from their profile using the same button you used to put them in the dungeon. Completing an idea will give you another idea point, my recommendation for the next one is the "long-term dungeon stay" idea.
Step 11b: At the same time that you're building up your sissies' brainwashing, check your finances and keep trying to pay back the loan. The interest builds up FAST but you earn pretty quickly too. Start buying ads ASAP, they'll pay for themselves. Pay off the loan just as soon as you can.
Step 12: Once a sissy is out of the dungeon, they'll keep accumulating brainwash points. Invest these in the "you should be brainwashed" idea first. Once this is filled up, the sissy will get 2 points per day.
Step 13: Fill the "long-term dungeon" idea next, once this is done put the sissy back in your dungeon. Now you can keep them there as long as you like.
At this point it's a matter of having sex with each sissy to build up their endurance. Buy butt-plugs and use them, they will build up gaping faster than you can by fucking them. Brainwash points will accumulate naturally, complete ideas as they come up. The "your ass is your pussy" idea allows for unprotected sex, so prioritise it. All other ideas are up to your preference.
A final note: the achievement system is bugged, so don't go chasing them.