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