If the achievements and endings do not unlock for you, I suggest deleting your persistent file from the following folders:
Steam\steamapps\common\CUPID - A free to play Visual Novel\game\saves
C:\Users\[User]\AppData\Roaming\RenPy\Cupid-1422075367

This will reset your progress, so make a backup copy just in case.
For me, playing through the game in the order you see the endings below unlocked everything, so hopefully you won't need to delete your files.

Some achievements unlock right after you made a certain decision (for example Cynical Mother, Justice Fighter, A Grudge), but most of the achievements will unlock during a certain ending. This makes tracking a little bit difficult and I decided to list the decisions I made during my playthrough to get a specific ending, and list the achievements which belong to the ending after it.

Also if you miss certain CGs, you might want to play with Mature filter ON/OFF, depending on what option you had before, and replay certain parts of the game. If you want to compare what you have to a complete gallery, check the Endings, CGs and Bonus menu section below.

Monster
Spectral Handjob
Oral Sex from Hell
Nightmare Fuel
Jealousy
Bloody Cupid
Wet Dream Gone Bad
Pat the Bunny
Fourth Wall

It will also grant you several other achievements during the playthrough, stated in ( ) right after the choices.

if you only miss "Jealousy" and have everything else, your problem might be you unlocked and checked "origin" section. Delete your persistent file and play ending 4 again.
Play this one with Mature filter off to get the achievements. Credits go to Salada, thank you for your help.

• Haven't you learned your lesson, idiot?! (Angry Start)
  
• Then stop your disobedience!
  
• This is all your fault.
  
• Are you hungry, child?
  
• He is the same as everyone. (Cynical Mother)
  
• There are no more good people in the world, child.
  
• Of course not!
  
• Didn't I tell you to leave?
  
• She was nothing but selfish.
  
• I am glad you are back to me.
  
• Look at how he is unperturbed by Catherine's death.
  
• Justice. (Justice Fighter)
  
• I knew it!
  
• Just go in and ignore him, child.
  
• Scold her.
  
• How dare you talk back to me! (Insensitive)
  
• Open it.
  
• Does Guilemme's presence upset you? (Catherine's 24k)
  
• It is obvious she will abandon you.
  
• Friendships do not last.
  
• She is selfish just like everyone else.
  
• You fancy him, don't you?
  
• Take the dagger first. (Bull by the Horns) (The Creature)
  
• Read more.(Incomplete Journal)
  
• Do it for me!
  
• To stop him from hurting people.
  
• Yes, it is.
  
• No, you are not!
  
• Don't worry, I will guide you. (Green-eyed)
  
• Scold
  
• Believe in Mother, child!
  
• Stop it.
  
• Yes
  
• To stop him.
  
• Because you are the only one who can!
  
• How dare you disobey me!
  
• Yes.
  
• Because he is a bad man.
  
• Of course not!
  
• Tell the truth
  
• Tell the truth
  
• Tell the truth
  
• Kill him, child!
  
• ...
  
• ...
  
• ...

Ending 4 unlocked

Does not Form Scars, Drawing Blood, Angel of Vengeancem, Punisher, Squick, Fan Disservice, You don't mean? and Emptiness achievements are unlocked.

• I fear for your safety.(Mother's Intuition)
  
• Alright.
  
• My poor child.
  
• Are you hungry, child?
  
• I do not care for him
  
• It is hard to say.
  
• Of course I do!
  
• Didn't I tell you people are cruel?
  
• She led you astray.
  
• I am glad she is dead.
  
• Remember the fear in Catherine's eyes in her last days?
  
• Retribution.
  
• We must get to the bottom of this.
  
• Leave now while he is not looking, child.
  
• Console her. //Save after this - Save 1 //
  
• Leave it alone. (Nonchalant)
  
• Are you worried about Catherine now that he's here?
  
• It is obvious he is never going to look at you.
  
• Family is more important.
  
• She is probably repulsed by you.
  
• You hate him, don't you?
  
• Take the key first.
  
• Read more.
  
• Do it for the greater good!
  
• To stop him from hurting people.
  
• Maybe not.
  
• Yes, you are.
  
• You've done if before.(Green-eyed)
  
• Convince
  
• Believe in Mother, child!
  
• Don't cry, honey.
  
• ...
  
• ...
  
• ...
  
• ...
  
• ...
  
• ...

Ending 3 unlocked.
Hostage achievement unlocked.

For Implied Incest:
Load Save 1 and choose "Open it" instead of "Leave it alone", then continue playing the way it is described above.

Players who already completed the game and "Play it again" is still missing:

Delete your persistent file and play through ending 2 first. The problem might be that many of you started with ending 1 when it was still bugged and "Play it again" requires ending 1 not to be unlocked.
Credit goes to Salada, thank you for your help. :3

• Haven't you learned your lesson, idiot?!
  
• Then stop your disobedience!
  
• This is all your fault.
  
• We must not linger.
  
• He is the same as everyone.
  
• There are no more good people in the world, child
  
• Of course I do!
  
• Didn't I tell you to leave? // Save after this - Save A //
  
• She led you astray.
  
• I am glad you are back to me.
  
• Look at how he is unperturbed by Catherine's death.
  
• Retribution.
  
• I knew it!
  
• Leave now while he is not looking, child.
  
• Console her.
  
• Open it.
  
• Are you worried about Catherine now that he's here?
  
• It is obvious she will abandon you.
  
• Family is more important.
  
• She is probably repulsed by you.
  
• You hate him, don't you? // Save after this - Save B //
  
• Take the key first.
  
• Read more.
  
• Do it for me!
  
• To destroy him, of course!
  
• Yes, it is.
  
• No, you are not.
  
• He will never change.
  
• What do you intend to do?
  
• Will that even work?
  
• Plead.
  
• I don't know.
  
• Why?
  
• I understand
  
• S-so be it... // Save after this - Save C //
  
• I don't trust him

Ending 2 unlocked.

The Talk, Guilleme's Soliloquy, Jealous Catherine, What makes a good parent?, Dysfunctional Family, Guilleme's Redemption, Play it again and Closure achievements are unlocked.

Replaying the ending from the Chapter Select will grant Love is Bittersweet and Poison and Cure.

For "Little Thief":
Load Save B and choose "Take dagger" instead of the key and continue playing the way described above.

For "Mother":
Load Save C and choose "Please take care of yourself" and then "I love you".

For "Mother's Past":
Get all the endings and go to the Bonus section and play the extra "origin". Then choose the same answers as you did for "Mother". (Load Save C, "Please take care of yourself" -> "I love you")

For "Emilie's Fate":
Load Save A and continue playing through until you reach the following choices -> "She is selfish just like everyone else" and "She is probably repulsed by you". Choose "She is selfish..." and continue playing.

For a complete walkthrough for Ending 1, please visit this site[himeutsugi.org]. You can find a guide made by Lore there.
I list the choices here for those who don't want to or can't open a browser to check it.

• I fear for your safety.
  
• Alright.
  
• My poor child.
  
• Are you hungry, child?
  
• I do not care for him.
  
• It is hard to say.
  
• Of course I do.
  
• Didn't I tell you people are cruel?
  
• She led you astray.
  
• I am glad you are back to me.
  
• Look at how he is unperturbed by Catherine's death.
  
• Retribution.
  
• We must get to the bottom of this.
  
• Leave now while he is not looking.
  
• Console her.
  
• Open it.
  
• Are you worried about Catherine now that he's here?
  
• It is obvious she will abandon you.
  
• Family is more important.
  
• She is probably repulsed by you.
  
• You hate him, don't you?
  
• Take the key first.
  
• Read more.
  
• Do it for me!
  
• To destroy him, of course!
  
• Maybe not.
  
• No, you are not!
  
• He will not listen to you.
  
• What do you intend to do?
  
• Will that even work?
  
• Plead.
  
• Yes.
  
• Why?
  
• I understand.
  
• S-so be it.
  
• Please take care of yourself. (Save here for Freedom achievement)
  
• I love you.

Ending 1 unlocked.

The Promise, Victim Mentality, Father and Child, Love is My Drug, Sound Advice, New Beginnings, Agape's Blessing achievements are unlocked.

For "Freedom":
Load the save and choose "Good Bye" instead of "I love you".

• I fear for your safety.
  
• Alright.
  
• My poor child.
  
• Are you hungry, child?
  
• I do not care for him.
  
• It is hard to say.
  
• Of course I do.
  
• Didn't I tell you to leave?
  
• She led you astray.
  
• I am glad you are back to me.
  
• Look at how he is unperturbed by Catherine's death.
  
• Retribution.
  
• We must get to the bottom of this.
  
• Leave now while he is not looking, child.
  
• Console her.
  
• Leave it alone.
  
• Does Guilemme's presence upset you?
  
• It is obvious he is never going to look at you.
  
• Family is more important.
  
• She is probably repulsed by you.
  
• You fancy him, don't you?
  
• Take the key first.
  
• Read more.
  
• Do it for me!
  
• To destroy him!
  
• Maybe not.
  
• No, you are not!
  
• He will never change.
  
• What do you intend to do?
  
• Will that even work?
  
• Plead.
  
• Yes.
  
• You love him, dont you?
  
• I understand...
  
• S-so be it...
  
• Please take care of yourself.
  
• Good bye

This will unlock Never Pure, Dedication, Dark Fairytale and Unlocked All Endings.

Modern Day Cupid
Just open the Bonus menu, click on Bonus once again and start the Epilogue.

This should have been a Comedy
In the section mentioned above, start the extra end. It also unlocks the last CG.

Playing as an Adult
Play with Mature filter turned off.

The first 4 should unlock before you reach "Read more" . For the rest, I suggest choosing "Read more" .
For those who already completed the game, just launch chapter 6. No need to a start new playthrough.

Filthy Colours

Domestic Abuse

Marquis de Sade

Sacrilege and Sex
Please note, you need Mature Filter turned off for this one.

More Entries to Unlock

Unlocked all Entries

Unlocked all of Guilleme's entries

BEWARE: SPOILER AND MATURE CONTENT AHEAD!!

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