Long ago someone wrote this guide. Hope this helps. I can't figure out why I can't find original author though

. All credits are his/hers.
1-2) Permanent Chastity/Permanent Chastity Together
agree to wear belt from Engineering Department and then tell teacher about it, they will be closed and you will be stuck in the belt (better not being with relationship). If you give buddy belt you get second ending
3-4) Memory Wipe/Prince's Concubine
go into interview and abroad. There you will have choice of staying with prince forever (second) or trying to escape, you will then get caught and put into some sex factory where you can stay forever (first)
5) Stepmother
became Dan wife, easy way to do it is after having chat with girls about sex and their experience you can go home or stay there with Dani and Haley. Stay and you will have this ending
6) Sugar Baby
work as stripper and in the end you will have choice to stay with client
7) Polyamorous Wife/Stepford Wife
you have to be Engineering penetration tester and try to hack belt (also on academic probation) if you put Bailey into belt you get first ending if not you got second
8) Permanent Vacation/Breeding Pet
Become Barry's slut. Go to island with him. Stay for the hunt. Don't get caught. Choose to stay. If you get pregnant, you get second ending.
9) Cuckqueen/Cougar
be Barry pet, drop from school and move with him, you find him cheating if you stay with him you got first ending if leave and divorce him you got second
10) Submissive Wife
get belt and go back to uncle after game (second vacation)
11) Artist's Muse
just pick this job and agree to everything
12) Swingers/Country Girl/Snitches Get Stitches
get expelled, do this alone, work as waitress, in court provide evidence for them. Don't recall what you have to do to get country girl ending and what for swingers, i think it was something about permanent or not transformation
13) Street Whore
get expelled, do this alone and work as whore
14) Catgirl Pet/Free Use Woman
get expelled, go to prison, don't fuck guard, you will be reeducated and at the end you can pick one of this two option
15) Chaste Parolee
get expelled, go to prison, fuck guard
16) Chaste Wife
drop school, move back with parents, agree to the belt from father
17-19) Large Family/Obedient Wife/Small Family
Choose Faith as roommate, work as barista, agree to date Andre, amount of kids will give one of this three endings
20) Enslaved
go to bar, go to Troy, don't fuck him, go out, in captivity lose strength
21) Submissive Lesbian Wife
Choose Samantha as roommate, work with her in the bar, be submissive
22) Boss Babe
just be yoga instructor
23) Professional Surrogate
get pregnant, carry the baby, don't be in relationship, have orgasm/masturbation denial also probably you have to be on academic probation (don't remember, don't care)
24) Trophy Wife
work in office (Emily roommate)
25) Army Wife
be barista, start working in bikini, don't be in relationship and go with the soldier
26-28) Prison Bitch/Life without Parole/Purple Prison Prostitute/Killed in Prison
All four ending require you to change back into man. Change cannot be permanent. You have to get expelled, work as waitress, get into court and there you will be given choice to go into male prison. There you will be attacked by inmate (and can be killed, it looks like it is random), agree to became his bitch (Prison Bitch ending), murdering him (Life without Parole ending) or take purple pill and became Purple Prison Prostitute
30) Cum Slut
Work with Olivia, get belted by Robert, don't go with him and you should have option to wear cumslut choker