60 Dirty Questions to Ask a Guy Worth a Try

What is your personal idea of what a perfect kiss should look like? Just tell me; you don't have to show me practically.

What do you think a perfect date should comprise of?

Besides me, who is your dream girl?

Where would you go to if you have to take your girlfriend to just one romantic spot in the world?

What event will you define as the most embarrassing moment of your life so far?

What do you wear to bed when you are in the mood for sex?

What part of the body would you want me to get a tattoo on?

How old were you during your first kiss, and who was the girl you kissed?

What outfit turns you on the most in a girl?

Have you ever felt like having sex while texting to someone on the phone?

Have you ever had a one night stand, and who was the girl you had it with?

If I were to be in your room right now, what are the things you would have loved to do to me?

What do you enjoy most about me during sex?

What color of lingerie and panties turns you on the most?

Have you ever been naughty enough to have sex in a public place, and were you caught in the act?

What is your definition of a perfectly sexy woman?

What part of your body do you enjoy being touched the most during foreplay?

Have you ever given in to the sexual advances of a much older woman, and how old were you at that time?

Apart from your mother, who was the first woman to touch your penis, and what did it feel like?

When you had sex for the first time, how old were you, and if you had a choice, would you change it to be later in your life or much earlier?

What would you consider the most shameful act you have ever been involved in?

Do you get intimidated when girls take the first steps towards sex?

How many girls have you been with before we met?

Which names would you prefer to be called, brainy or sexy, cool or cute?

If you have the chance to date a female celebrity, who would you choose?

Do you like checking out a girl's features when she walks away after talking with you?

Have you ever been in a situation where someone you were not in a relationship with walked in on you while you were naked, and what was your immediate reaction?

What are the physical features you are most attracted to in a girl?

What is your idea of a perfect foreplay?

Have you ever exchanged naked pictures with any girl?

Have you ever had cyber sex with a total stranger?

What would be your immediate reaction be if you lose your trunk while swimming?

Tell me what your parents look like, are they as good looking as you are?

What is the weirdest thing you have ever dreamt of doing with a girl?

When was the last time you dreamt of me?

If I were to choose between wearing a yoga pant and a short skirt all through my life, which would you prefer I wear?

Can you guess the color of the panties I'm wearing now?

What is the naughtiest thing you have ever done in your life, and how old were you when you did it?

Have you ever experienced the embarrassing situation where you say another girl's name while having sex with your girlfriend?

What part of your body would you say is the most sensitive?

Have you ever been involved in a game of double dating at any point in your life?

Have you ever been caught by anyone masturbating?

Have you ever practiced with sex toys?

When last did you masturbate?

If you were asked to choose one sex style for life, what would you choose: regular, anal or oral?

Do you love your woman with hairs on her private area or bare?

What is your favorite sex position?

If you could get a once in a lifetime chance to sleep with a single celebrity, who would you want to sleep with?

Do you feel jealous when you see me discussing with other guys?

If you catch me making out with another hot girl, will you join us or get angry?

Have you ever slept with someone, and then woke up wishing you hadn't slept with her?

If you were asked to choose between a slightly underweight and a slightly overweight me, which would you go for?

Would you love sex for breakfast and for dinner?

What is your take on public display of affections?

What is the difference between making love and sex?

If you get the chance to change the age you were when you lost your virginity, would you choose a younger or an older age, and why?

Have you ever had a threesome?

Have you ever found yourself in a friends-with-benefits situation?

What arouses you the most, and why?

Have you ever slept with a woman for money?