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.

Two Trains In a Tunnel

Riddle:

Two trains enter a one-way tunnel at different ends exactly at 9:00, But they both come out the other end unharmed 5 minutes later. How is this possible?
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Rewarding When It Is Hard And Long

Riddle:

What is more rewarding when it is hard and long?
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An Unsinkable Virgin

Riddle:

What do you call an unsinkable virgin?
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You Move Me Around With Your Lips And Tongue

Riddle:

I am long, you move me around with your lips and tongue, I get wet with saliva and I get sucked. What am I?
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If I Miss, I Hit Your Bush

Riddle:

If I miss, I hit your bush. It’s my job to stuff your box. When I come, it’s news. What am I?
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I’m Amazing When Using My Mouth

Riddle:

I work with briefs and I’m amazing when using my mouth. What am I?
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A Happy Sex Life...

Riddle:

Why is a happy sex life like a good steak?
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Set Me To Vibrate…

Riddle:

Set me to vibrate when you want some alone time. What am I?
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I Was Ripped Open By Something Long And Hard

Riddle:

I once let over 1000 different people inside me, until I was ripped open by something long and hard. What am I?
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I Love Holding Your Buns All Day

Riddle:

I absolutely love holding your buns all day. What am I?
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I Drip When You Take Me In The Mouth

Riddle:

I drip when you take me in the mouth. What am I?
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It Gets Wetter When Things Get Steamy

Riddle:

What gets wetter when things get steamy?
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For Me To Grow I Need Stimulation

Riddle:

Every man has me. I’m a word that begins with the letter “P” and for me to grow, I need stimulation. What am I?
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You Use Your Hand To Whack Me Off

Riddle:

You use your hand to whack me off, the bigger I am, the louder I make people scream. What am I?
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Women Really Love To Get Their Hands On Me

Riddle:

I am a five letters word starting with “P”. Women really love to get their hands on me. What am I?
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I Love Being Filled With Wood

Riddle:

I am dirty, I love being filled with wood, but someone only goes down on me once a year. What am I?
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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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My Tip Penetrates

Riddle:

I have a stiff shaft. My tip penetrates. I come with a quiver. What am I?
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Goes Into a Tiny Hole

Riddle:

What is super hard and goes into a tiny hole?
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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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You Play With It At Night

Riddle:

You play with it at night and it vibrates. What is it?
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Six Inches Long and Goes In Your Mouth

Riddle:

What’s at least six inches long, goes in your mouth, and is more fun when it vibrates?
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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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