Riddles > Tricky Riddles

Our tricky riddles are our middle difficulty level riddles, if you find our easy riddles TOO easy, this is where you should try your skills before trying our hard riddles and our hardest riddles.

Some People Prefer Being On Top, Others On The Bottom

Riddle:

Some people prefer being on top, others prefer being on the bottom, and it always involves a bed. What is it?
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The Thing That a Man Has In His Trousers

Riddle:

What does a man have in his trousers that a lady doesn’t want on her face?
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The Thing That Men Keep In Their Pants

Riddle:

What do men keep in their pants that their partners sometimes blow?
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Blow It To Play With It

Riddle:

You have to blow it to play with it. What is it?
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It Has The Word ‘Cum’ In It

Riddle:

What’s long and hard and has the word ‘cum’ in it?
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Six Inches Long And Sweet On The Lips

Riddle:

What is six inches long, sweet on the lips, and goes down better with butter?
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Insert In a Small Hole

Riddle:

What do you insert in a small hole and twist all the way around?
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You Can’t Taste It Unless You Undress It

Riddle:

You can’t taste it unless you undress it. What is it?
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Woman Had Two Cow Has Four…

Riddle:

What does a woman have two of that a cow has four of?
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Better To Spit Than To Swallow

Riddle:

What’s white, sticky, and better to spit than to swallow?
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I’m Great For Protection

Riddle:

I’m great for protection. You use your fingers to get me off. What am I?
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What Gets Longer If Pulled

Riddle:

What gets longer if pulled, fits snugly between breasts, slides neatly into a hole, chokes people when used incorrectly, and works well when jerked?
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I’ll Fill Your Holes When You Ask Me To…

Riddle:

When I go in, I can cause some pain. I’ll fill your holes when you ask me to. I also ask that you spit and not swallow. What am I?
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I Come In a Lot Of Different Sizes

Riddle:

I come in a lot of different sizes. Sometimes, I drip a little. If you blow me, it feels really good. What am I?
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Riddle Me This...

Riddle:

Riddle me, riddle me, rin-е-go, mother gave me some seeds to sow. The seeds were black, the ground was white. If you riddle me that, you'll escape my bite. What are they?
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A Beautiful Face

Riddle:

My love, when I gaze on thy beautiful face, Careering along, yet always in place - The thought has often come into my mind If I ever shall see thy glorious behind.
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What Is It?

Riddle:

What occurs once in a date, twice in Valentine’s Day, and three times in everlasting love?
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Two Days in February

Riddle:

What did February 14 say to February 1?
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I Can Forever Last

Riddle:

Current, serious, steady, or fast, It can also be either painful or beautiful, And sometimes it can forever last. What is it?
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Two Ants

Riddle:

What do you call a couple of Italian ants?
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Dining Habits

Riddle:

From that which comes within itself, It builds its table on my shelf. What is it?
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Which Fierce Animal Am I?

Riddle:

I have legs but rarely walk. I bite many but never talk. I search for places that can hide me, Because those that feed me also hate me. What am I?
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Banana Race

Riddle:

A raven, a monkey, and a squirrel are all racing to the top of a coconut tree. Which animal will get the banana?
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The Cat and the Window

Riddle:

A cat can jump up to 6 and a half meters. There is a window 3 feet away from the floor, but the feline can’t jump through it. Why?
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Tick-tock, Bow-wow!

Riddle:

What goes tick-tock, bow-wow, tick-tock, bow-wow?
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Chased by a Tiger

Riddle:

What steps must you take when you notice a tiger running toward you?
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The Leopard's Plight

Riddle:

Why is it so difficult for the leopard to hide?
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Growing Down

Riddle:

I grow down as I grow up. What am I?
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Can You Guess the Wild Animal?

Riddle:

What king do you make if you take the head of a llama, the middle of a pig, the back of a buffalo, and the tail of a stallion?
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Never Owned But Often Loved

Riddle:

Sneaky as a shadow in the dead of night, Cunning but affectionate if given a bite. Never owned but often loved. What am I?
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