Eye-key-can. Akikan is about drink cans that become girls for battle. 

Good to say what it shown out loud. Could be literal, could be a pun, could be both. 

Question 1 of this cringy pictionary. All questions are possibly literal, puns or maybe both. 

Tensura aka That time I got reincarnated as a slime. the computer in the third image relates the MC's last wish. if you know, you know. 

If you watch enough animes, you would know this, even if you've never watched it. 

Question 2. Literal or Pun, maybe both.

Rather literal image and hint. Anime: Danmachi aka Is it wrong to pick up girls In a Dungeon.  If you think to hard you will gaslight yourself into choosing the wrong one. 

The more you think about it, the harder it gets. 

Question 3. Literal or Pun, maybe both.

While the image is of Dragon Maid. I specifically picked the scene of a boy holding ball who also is a dragon.  So works on a few levels. 

What do you see in this image? That's the answer. 

Question 4. Literal or Pun, maybe both.

in the anime DearS, that is simply the name given to the aliens. 

Shikanoko nokonoko koshi tantan  

Question 5. Literal or Pun, maybe both.

Fairly obvious, which is why it's a early question.  

Yep those are koi fish alright. But why that image. 

Question 6. Literal or Pun, maybe both.

Bodacious Space Pirates also known as "Miniskirt Pirates". A anime about a school girl who inherits a space pirate ship. 

Even if you watched FMA and know the reference, you may not get it right away. Though saying it outloud helps. 

Question 7. Literal or Pun, maybe both.

Answer also has a secondary full name as "All purpose catgirl nuku nuku tv". So naturally using All Purpose Flour made sense. 

Combine the images together. 

Question 8. Literal or Pun, maybe both.

Ookami to Koushinryou in english is "Spice and Wolf". Akira from Food wars is smelling a Cinnamon stick, a spice. As his iconic trait is using spices. 

Campfire Cooking in Another World with My Absurd Skill

Say each picture out loud separately and then put them together. 

Question 9. Literal or Pun, maybe both.

All answers in this question were for the same anime. All the titles were just various canonical versions of the name. 

 Regardless of My Adolescent Delusions of Grandeur, I Want a Date!

Even with Eighth-Grader Syndrome, I Want to Fall in Love

This is a freebie 

Question 10. You made it this far, so what is the correct term for the people in the picture? 

Meitantei Conan, Detective Conan, Case Closed.  Showing just some briefcase or any case wouldn't give a big enough hint so i used one closing. 

What's happening here? 

Question 11. Literal or Pun, maybe both.

Shichinin no Nana = Seven of Seven. Plot involves the MC having 6 copies of herself, each slightly different. 

All possible good answers, only one is correct. 

Question 12. Literal or Pun, maybe both.

Why it's called I My Me Strawberry eggs, who knows. I've watched it many times, and only got guesses. The image i used was strawberries on a egg plater with egg-like toppings. 

Ironically the name has really nothing to do with the show. 

Question 13. Literal or Pun, maybe both.

I used a certain image for a reason.  There's a lot of "Rail" ways  and a girl holding a "Gun".  But also felt the pose was very similar to Railgun's MC iconic pose. Google Misaka shoots railgun. 

Aria the Scarlet Ammo: The Butei Come and Train

Only hint is to think of why i choose the specific scene I did, specifically that stance. 

Question 14. Literal or Pun, maybe both.

You thought It was a just a Jojo reference, but it was Yugioh!  

Question 15. Literal or Pun, maybe both.

Keijo has a extended name of "Hip Whip Girl" shown in the opening and manga cover. So yeah.  Genshin Eula's hips, a whip sword and crossover of girls since Keijo parodies anime attacks. 

The Iceblade Sorcerer Shall Rule the World

Ignore the characters, focus on why I choose these images and why three images. 

Question 16. Literal or Pun, maybe both.

Air=wind + Gear stick. Simple yet tricky if you think to much. 

Is it easy and obvious or will it require a lot of thought. If you know what's happening, then you know. 

Question 17. Literal or Pun, maybe both.

Anime also known as Nyaruko-san Another Crawling Chaos or Nyaruko Crawling with Love. So Fairy Tail Juvia known for intense love crawling after someone was fitting. She was fighting someone who connects sense too.

Yes it's Fairy tail's Juvia crawling, that's all i will say.

Question 18: Literal or Pun, maybe both.

C3 aka Cubed x Cursed x Curious.  Found the idea of a curious/confused geas' C.C to be cute and then having the image as a Cube showing her three times makes it better. 

If you know the character in the image, it may make it easier or harder, depending on your how you think about it.  

Question 19. Literal or Pun, maybe both.

Gonna be the Twin-tail is exactly that, a anime where the love of twintails gives magical girls their power. Also i picked as it so well. Cyan hair for one, blonde twintails for another, also red coloring. 

Final question.  Fairly obvious if you think about it. 

Question 20. Literal or Pun, maybe both.

A anime quiz with a twist. You should not google the choices, only use what is shown. 
Now think Pictionary, the images in each question hint towards the answer. Sometimes pun, sometimes literal, all fun and cringy with what each implies. 
Also NO, sorry Bleach, One punch man and certain others are not in this quiz for obvious reasons.