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