Here is the full list of all 32 Coming Out on Top achievements. It takes around 12-15 hours to unlock all of the achievements on Windows.
Cuckold someone for poor culinary skills.
Take a laxative.
Break the fourth wall.
Romance your pet fish.
Enjoy a cupcake.
Attempt to take down your university's corrupt athletics department.
Get Jed's sexual ending.
Get Jed's romantic ending.
Get your mugshot taken.
Get Brad's romantic ending.
Get Alex's romantic ending.
Get busy on a desk.
Go with Ian to South America.
Drink milk like a boss.
Get Ian's romantic ending.
Uproot a plant for a loved one.
Get Amos's romantic ending.
Taste one of life's finer pleasures.
Make it through the award winning film, "While I Sleep"
Get your cavity searched.
Get Phil's romantic ending.
Win a game of trivia.
Wear a top hat.
Use Ian's toy.
Use Ian's lube.
Graduate with honors.
Destroy a construction site.
Survive a kidnapping.
Jump up and down in a broken elevator.
Commit the crime of rickrolling.
Sell a personal item that belongs to a famous pop star.
Try an exotic ice cream flavor.