Every week for WTMFI Wednesdays, we ask you a series of 5+1 questions.

Each session’s questions are based on a variety of topics surrounding sexuality. While the topics dictate the content, themes dictate the overall structure of each session. For some themes, we will only focus on one topic, while other themes will focus on a variety of these topics. See a full list of all topics covered at the bottom of this page.

Below, you will find a list of each of our themes and a short description and examples of questions that you can expect. Each of these questions are actual questions from our sessions so that you can familiarize yourself with our format.


Q&A | The 5 W’s | Have You Ever… | Would You Rather…| Should/Could/Would


In our Q&A theme, we ask you 5+1 questions on a mixture of topics related to sexuality.


  1. What was your first time kissing like?
  2. Did you orgasm the first time you masturbated?
  3. What was it like giving oral sex the first time?
  4. Do you think you were good or bad at sex the first time?
  5. What was your first time falling in love like?

BONUS: How do you feel now about your first sexual experiences?

From Session #1 – Q&A: The First Time

The 5 W’s

When we post The 5 W’s, we’re asking you Who, What, Where, When, Why – and as a bonus, How – with a specific topic in mind.


  1. Who was the first person you had sex with? (Don’t use real names, but describe the person to us)
  2. What was the sex like your first time?
  3. When did you have sex your first time?
  4. Where did you have sex your first time?
  5. Why did you decide to have sex your first time?

BONUS: How did you feel about your first time afterwards? Now?

From Session #21 – The 5 W’s: You First Time

Have You Ever…

In Have You Ever…, we ask you 5 + 1 questions about all the things you have and maybe haven’t done and of course, always ponder whether you’d even want to!


  1. Have you ever used food during foreplay or sex?
  2. Have you ever used a sticky food during foreplay or sex?
  3. Have you ever used ice during foreplay or sex?
  4. Have you ever used hot food during foreplay or sex?
  5. Have you ever used candy during foreplay or sex?

BONUS: Have you ever eaten food off of someone’s genitals?

From Session #24 – Have You Ever: Pour Some Sugar On Me

Would You Rather…

In Would You Rather…, we give you 5 + 1 different sets of two options – sometimes fun and sometimes not so much. Then, we ask you which one you’d rather do and why.


  1. Would you rather have sex indoors or outdoors?
  2. Would you rather have sex at night or during the day?
  3. Would you rather have sex after waking up or before falling asleep
  4. Would you rather have a shower before or after sex?
  5. Would you rather be completely naked or have clothes on during sex?

BONUS: Would you rather kissing or dirty talk during sex?

From Session #22 – Would You Rather: Day or Night?


With Should/Could/Would, we ask you to reveal your deepest thoughts, feelings and opinions on a variety of topics related to sexuality.


  1. Should all people involved in a sexual encounter always orgasm?
  2. Could you feel satisfied after a sexual encounter without orgasm?
  3. How would you feel if you couldn’t bring your partner(s) to orgasm?
  4. Could you imagine never having another orgasm?
  5. How would you describe an orgasm?

BONUS: Should you orgasm every time you masturbate?

From Session #20 – Should/Could/Would: Orgasm


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