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