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