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I've looked at the game's code. It depends on the choices you make during the story line. There is a variable called sympathy that starts at 0. Some choices increase sympathy and some decrease it. If you have at least 1 sympathy, she will choose to stay with you.

Choices that increase sympathy:

• You don't have to be so formal.
• I'm glad you like it. (after giving her the normal dress)

Choices that decrease sympathy:

• *Push her head down*
• It's proper apparel for a whore like you.
• I guess even you're good for something.
• *Find a stray dog*

There are only 2 chances to increase sympathy and one of them is locked to the normal dress path. So in order to have her stay with you when giving her the lewd dress, you must choose the "You don't have to be so formal" option when you first meet her and NOT choose any of the options that decrease sympathy. You can also just edit the save file to increase sympathy.

I noticed on my 100+ day playthrough that I don't remember anyone's vagina or asshole tightening even once. I checked my list of slaves and most of them had a loose vagina and/or asshole, even though many of them hadn't had sex in weeks or even months. I then checked the scripts and found a problem that prevents any tightening.

In the dailyTighten function you have these lines for vagina and asshole:

if averagesize < globals.vagsizearray.find(person.vagina) && rand_range(0,100) <= globals.expansion.settings.vaginaltightenchance * (age-4):

if hole in ['all','asshole'] && person.asshole != "none" && rand_range(0,100) <= globals.expansion.settings.analtightenchance * (age-4):

You have 4 being subtracted from age (which is 1, 2, or 3) so you end up with either -1, -2, or -3. Then the tighten chance is being multiplied by this number giving you a negative number (ex: 25 * -2  = -50). With rand_range generating a positive number from 0 to 100, this condition is always false and no tightening can occur.

I fixed this by getting the absolute value instead:

if averagesize < globals.vagsizearray.find(person.vagina) && rand_range(0,100) <= abs(globals.expansion.settings.vaginaltightenchance * (age-4)):

if hole in ['all','asshole'] && person.asshole != "none" && rand_range(0,100) <= abs(globals.expansion.settings.analtightenchance * (age-4)):

By doing this, the above example would change from -50 to 50 and you would have a 50% chance for the condition to pass. I tested this and my slaves started occasionally tightening after this change. I probably over explained all this to you but I prefer to be very descriptive just in case to minimize the chance of misunderstandings.

Also noticed something else when checking out this function.

if rand_range(0,100) <= globals.vagsizearray.find(person.vagina) + (difference*10) + (age*5) + (person.sexexpanded.elasticity*20):

if rand_range(0,100) <= globals.assholesizearray.find(person.asshole) + (difference*10) + (age*5) + (person.sexexpanded.elasticity*20):

The age * 5 means that you are making it more likely for older slaves to tighten right? Isn't it supposed to be the opposite or am I missing something?