Introduction
It is not possible to obtain all of the achievements on one play through, without using saved games to repeat events. On the first play through I'm going to go for the less obvious achievements.
I decided to break the game down into days after the tutorial portion, even though there is no way to keep track of the day number in the game. I put in Save Game prompts for the areas where you will need to play through twice to get an achievement. You could get to the next day, save, then load the save and go through the prompts to get the achievement by going to the Second Play Through Achievements sections. Most of the achievements in the Second Play Through section are the act like an ass type achievements.
As I already had most of the achievements this guide has where you should earn the achievement. For the few achievements that aren't actually mentioned you should gain them along the way.
The Tutorial
While playing the tutorial part of the game you will not have all of the options available that you will have later.
Before you start playing let the whole main menu video play through to earn the AFK achievement.
The game starts off and you get to select your name and your relationships with the three women in the house, two about your age and an older woman. Only relationships where these people shouldn't be having sex with each other will make sense in the context of the story.
Receive the First step achievement
Press P to activate the Panic screen and earn the Much panic! Such wow! achievement
The game opens with a scene with Nadia.
Receive Sweet dreams achievement.
A car alarm goes off and wakes you from your dream about Nadia.
Jessica comes into your room and tells you to get up.
Press the Angle button to see Jessica from different angles
Earn the Different perspective achievement
Early on in the game you aren't going to have any real options. You're going to have a single choice. The more rewarding choice will be presented in BOLD text and the less rewarding will be in regular text.
Get upIgnoreGo into the Hall
Go into the Bathroom
Take a showerBrush teethGo into the Hall
Go downstairs
Go to the Kitchen
Eat your breakfast
Go to Town
Go to School
NoEnter school
Click on Zoe and Megan
Go to classSulfuric
High
Sulfate
Vitriol
BurnEarn Mr. Heisenberg achievement
Go back into the Hallway
Go back to your house
Go into the Living Room
Click on Jessica
Leave her alonePress the Hints button, you're going to be doing this a lot for this game.
Go to the Garage
Click on the work bench
Click on the Red button in the upper right when Elizabeth comes in.
Earn the X-Ray achievement and see Elizabeth topless.
The Red button will sometimes remove clothes, other times it will show the girl(s) in different outfits, so X-Ray is a bit misleading.
Go to the Kitchen
Go to Living Room
Click on Megan
Watch TVGo to your roomShe went outGo to your room
Go studyContinue studying
Day 2IgnoreGo into the Hall
Go into the Bathroom
Take a showerBrush teeth
Go into the Hall
Go downstairs
Eat BreakfastGo to Town
Click on the house next to your eight times
Earn the Wrong house, m8! achievement
Go to School
Enter School
Click on Megan and Zoe
Go to classGo to Classroom
Sulfuric
High
Sulfate
Vitriol
BurnGo into Living Room
Click on Jessica
Go to the Garage
Click on the Work Bench
Go to your room
Click on the bed
RelaxGo into the Hall
Go into the Bathroom
Click on the sink
Click on the sleeping pills
Day 3AnswerGo into the Hall
Go into the Bathroom
Take a shower
Go downstairs
Go to the Kitchen
Click on Elizabeth
Save Game 1FriendlyPick either options
No (Friendly)or
I'll think about itEnter School
Go to Classroom
This is the last time you'll have to take the Pop Quiz
Sulfuric
High
Sulfate
Vitriol
Burn
Ask her directl
Truth
Go home
Earn the Walk with me achievement
Go to the Living Room
Click on Jessica
Try talking to her some more
Talk some moreGo to Jessica's room
Click on the laptop
Enter the passwordGo to your room
Explore the house until you earn The Explorer achievement
Click on your bed
Go to the Living Room
Click on Megan
Fine
Go to your room
She went on a dateEarn the Snitches get stitches achievement
Slightly open the doorEarn the Perv! Achievement
Earn the Finally free achievement
Click on your phone in the upper left
Click on the Gallery icon
Earn the Pretty Pictures achievement
Press the Hints button
Earn the Where was I? achievement
Now we're ready to start playing
Day 4
Answer Zoe
Go to the Kitchen and click on Elizabeth
Pick either option
How's workor
How are you doing?Use the Map and go to the Town Map
Go to the School
Go into the School
Go into the Classroom
Go into the Hallway
Block (You have to do it before the bar disappears. If you miss you can mouse wheel up to try again)Earn the Like a ninja, or something achievement
Go to Hallway 2 around the corner
Go into the Bathroom
Click on the Whatever Just Wash Your Hands poster
Earn the Equality achievement
Click on Ellie
Go to the Living Room
Use the Fast Forward to get to the night
Click on Elizabeth
Why not
You can pickForward Time to Morning
Earn the Reset! Achievement
Day 5
Don't skip Jessica
You're rightGo to Jessica's room
Click on Jessica
Talk
ComplimentGo to Megan's room
Barge inEarn the Ever heard of knocking? Achievement
You in a rush?Go to school
Click on Ellie
Walk up to her
Enter school
Enter classroom
Go to Bath Room
Talk to Ellie
Pick any one of the options
Show me your boobsShow me your ♥♥♥♥♥A blowjob
Earn the Creep achievement
Go Home
Go to the Living Room
Click on Jessica
Go to Jessica's Room
Advance time to Evening
Click on Jessica
Make a jokeGo to your room
Advance time to Night
Click on the computer
Click on the computer
Don't touchGo to Living Room
Click on Elizabeth
Romantic comedy
Day 6
Go to Megan's Room
Click on Megan
Talk about the car alarm
Go to School
Click on Ellie
Sneak up on herEnter school
Enter classroom
Go to Bathroom
Click on Ellie
I like your outfit
You suck?
Sorry. 'Meant to say "It sucks"
I like trains. (Like the Block you have to do it before the bar disappears)Earn the We all do! Achievement
Pick either option
You have to do 20 sit-upsor
You have to run 3 laps around the schoolGo back to Hallway 1
Click on the door to the Teacher's Lounge
Compliment her
Ellie will show me her boobsEarn the Honesty pays achievement
Go back to the Bathroom
Click on Ellie
Give her the gunPick whichever one you want to see
Pinch your nipple or
Squeeze your boobs togetherPick whichever one you want to see
Bend overor
Lift your leg on the sinkYou're done with Ellie until you get your Sexual Experience up to 5.
Sexual Experience 1/5
Go to Classroom
Click on Nicole
I don't like her either
Looks aren't everything
WaitGo to the Store
Click on Micky
Still working two jobs, I seeGo Home
Advance the time to Night
Go to Jessica's Room
Catch her (Another timed selection, do it before the bar disappears)Advance time to Morning
Day 7
Rush to the Bathroom (very quick timed event)If you missed it, mouse up and try again
Slowly open the doorReceive the Steamy Shower achievement
Go to School
Enter school
Click on Megan and Zoe
Go into Classroom
Go to Store
Click on Micky
You got scratch-off tickets?Go Home
Go to Jessica's Room
Click on the laptop
Try guessing the passwordGo to Living Room
Advance time to Night
Click on Elizabeth
You can pickYup!Start jacking off
Day 8
Go to School
Enter school
Click on Megan and Zoe
Try sneaking in closerEnter the Classroom
Click on Megan
Pick either choice
I heard you and Zoe talking…or
Err…I thought…Go Home
Go to Living Room
Click on Jessica
Go to Jessica's Room
Advance time to Evening
Click on Laptop
Go to Living Room
Advance time to Night
Click on Elizabeth
Enjoy the scene
Day 9
Click on Answer Zoe
Go to School
Enter school
Go to Teacher's Lounge
Enter Classroom
Click on Nicole
Go to Hallway 2
Enter the Girl's Locker Room (Locker Room will not be available if you didn't Answer Zoe)
Don't assume my gender! (Another timed response)Earn the Never assume achievement
Hidden Event 1Wait about 15 seconds until the Spy on Zoe option appears.
Spy on ZoeEarn the Peeping Tom achievement
Go Home
Go to Jessica's Room
Click on Laptop
I found it openGo to Living Room
Advance time to Night
Click on Elizabeth
Enjoy the scene
Sexual Experience 2/5
Day 10
Answer Zoe
Go to School
Go to Classroom
Click on Nicole
Not all menNot a kidStay on the subjectPick
Back to text messageor
Flirt a littleEarn the Selfie! achievement
Talk some moreGo to Girl's Locker Room
Don't assume my gender! (Timed response)Go inRespondGo Home
Go to Living Room
Click on Jessica
Nothing importantAdvance time to Night
Click on Elizabeth
Enjoy the scene
Day 11
Recap everything that happenedAnswer Zoe
Click on the door to Megan's Room
Wait about 15 seconds until the Spy on Megan option appears
Hidden Event 3Spy on MeganEarn the Peek-a-Boo achievement
Follow MeganGo to the Classroom
Save Game 2Go to the Girl's Locker Room
RespondAbout the partySay nothingThey seem okayI guess they're the right sizeAre you sure?Squeeze her boobGo to the Girl's Locker Room
Wait about 15 seconds for the Go in anyway option to appear
Hidden Event 2Go in anywayEarn the Even girls do it achievement
Go to the Classroom
Click on Megan
Go to Megan's Room
Click on Computer
Click on bed
Click on Bookshelf
Day 12
Go to School
Go to Classroom
Click on Nicole
Blackmail her with the nudesBraGo to the Mall
RedheadsMention MeganGo Home
Go to Jessica's Room
Advance time to Evening
Click on Jessica
Click on the Blue Plant
Advance time to Night
Click on Elizabeth
Pick either option
Go balls deep!or
Go slow
Day 13
Go to school
Go to Classroom
Go to Girl's Locker Room
Wanna go to the partyYeahMeganI just wanted to see your reactionPick anyone of the three
Kendall JennerMargot RobbieKate UptonGrab her boobsShow her♥♥♥ on Zoe (Timed Choice)Sexual Experience 3/5
Advance time to Afternoon
Go to the Mall
DirectBig ♥♥♥♥Just do itEarn the Black eye achievement
Go Home
Advance time to Night
Go to Jessica's Room
Walk in on her
Day 14
Go to the Kitchen
Click on Elizabeth
Continue staring at her boobs
Brush against her again
Go to School
Go to Classroom
Go to Girl's Locker Room
Sexual Experience 4/5
Go to the Mall
DirectBig ♥♥♥♥Don'tGo home
Go to Jessica's Room
Click on the laptop
Go to Living Room
Advance time to Night
Click on Elizabeth
Push itGo to your room
Click on computer
Intermission - Hidden Event 4
Time for a little break from the main story. Now would be a good time to create a Save point, in case you want to do this again.
Go to the Bathroom
Press the Flush button on the toilet
Make any selections you want, there are no achievements other than NFG 1 for this section. You can reload your save to see what different selections do.
Earn the NFG 1 achievement
Intermission Continued - Hidden Event 5
Now would be a good time to create a Save point, in case you want to do this again.
Go to the Bathroom
Click on the toilet brush
I'll take my chancesPick either option
Warn heror
♥♥♥ on her faceApologizeAfter you leave the classroom you will receive the Payback achievement
NoEarn the NFG 2 achievement
You can reload your save to see what the other options do, but this is the best path through the event.
Day 15
The days are going to go by a lot quicker as we start wrapping things up.
Advance time to Afternoon
Go to the Mall
Smooth
MeganGo Home
Go to Megan's Room
Click on the bed
Day 16
Go to Living Room
Advance time to Night
Click on Elizabeth
Drop it
Go to Your Room
Click on Computer
Earn the Ouch achievement
Day 17
Go to Living Room
Advance time to Night
Click on Elizabeth
You're beautiful
Women like you
Kiss her
Day 18
Advance time to Eveningjavascript:ValidateEditSubSectionForm()
Go to Elizabeth's Room
Click on Elizabeth
Go to Living Room
Save Game 3Click on Elizabeth
Everything
Go for it
Day 19
Advance Time to Night
Click on the Computer
Apologize
Day 20
Advance time to Night
Click on the Computer
Sexual Experience 5/5
Earn the Experienced! achievement
Day 21
Go to School
Go to Bathroom
Advance time to Noon
Click on Ellie
Grab her titEarn the Karma achievement
Go to Your Room
Advance time to Night
Click on the Computer
Day 22
Go to School
Go to Bathroom
Advance time to Noon
Click on Ellie
Walk pastPick either option
Let me finger youor
Lick my ballsAdvance time to Night
Click on Computer
Day 23
Suggest another idea
Day 24
Go to School
Go to Bathroom
Advance time to Noon
Click on Ellie
Day 25
Advance time to Night
Click on Bed
Stay awake
Remain "asleep"
Day 26
Go to Jessica's Room
Continue the "Photoshoot Story"
PeekPick either option
My sisteror
My girlfriendPick either option
Stick it inor
Don't do it
Day 27
Advance time to Night
Click on Bed
Wait for the girls
Knock
Wrong Answer
Right AnswerPick either option
Jessicaor
Chloe
Day 28
Go to the School
Go to the Classroom
Click on Nicole
Ask to keep her company
Day 29 - Freeze Day
Smash itEarn the Smash! achievement
Earn the Everybody, freeze! achievement
Day 30
Go to School
Go to Classroom
Click on Nicole
Continue blackmailingReceive Blackmail veteran achievement
Advance time to Morning
Second Intermission - Hidden Event 6
Save Game]Click on Toilet Paper Roll
♥♥♥♥ it
Make your selections and reload or restart as necessary.
Answers for Nicole's "test"
Potassium hydroxide
Three, four, two and one
Allosteric inhibitor
Introduction of a bulky N-alkyl substituent
Earn the NFG3 achievement
Second Intermission Continued - Hidden Event 7
Save Game
Go to the Bathroom
Click on the Toilet
Knock 4 timesEarn NFG 4 achievement
Second Intermission Continued - Hidden Event 8
Save GameClick on the Toy Bike in Your Room
Earn the Perfection! achievement
Day 31
Go to School
Enter School
Go to Classroom
Talk to Nicole
Talk to her
Don't kiss her
Advance time to Morning
Day 32
Go to School
Enter School
Go to Classroom
Go to Girl's Locker Room
No, I don't like you like that
Go with it
Advance time to Morning
Day 33
Go to Megan's Room
Catch (Timed reaction)
Day 34
Answer
Second Play Through Achievements
Load Save Game 1Day 3When talking to Ellie
Ignore (Insensitive)
Earn the Douche achievement
Load Same Game 2Day 11Go to the Girl's Locker Room
Respond
About the party
Say nothing
Nothing special
Meh
Insult her
Earn the Heartless achievement
Load Save Game 3Day 19When talking to Elizabeth
Big titsEarn the Say it ain't so achievement
Source: https://steamcommunity.com/sharedfiles/filedetails/?id=2590461159