Ask me any of them; I dare you 😉
What tends to feel better for you: sex or masturbation?
Have you ever had your prostate stimulated?
Have you ever had an orgasm from anywhere other than your genitals?
Are you well-acquainted with the G-spot?
Are handjobs boring, or underrated?
Do you like having your balls touched?
Do you like having your nipples touched?
Do you like having your anus touched?
Have you ever been pegged?
Do you like mild roughness (scratching, spanking, hair-pulling, etc.)?
Are you into anything under the BDSM umbrella?
Do you pee in the shower?
Do you ever masturbate in the shower?
Have you had sex in the shower?
Do you sleep partially/fully naked?
Have you ever skinny dipped?
What’s the most unusual thing you’ve done nude?
Have you ever to a nude beach, naked party, or other situation involving casual nudity?
Are you comfortable being seen partially/fully naked by family or friends (i.e. getting dressed, etc.)?
Are you comfortable with partners seeing you nude in non-sexual contexts?
Have you ever showered with someone (non-sexually)?
Do you care if a partner sees you going to the bathroom?
Do you have naked pictures/videos of yourself? If yes, have you sent them to anyone? Are they online?
How many sexual partners have you had?
How often do you masturbate?
Age you started masturbating? How did you discover/learn about it?
What position do you typically masturbate in (laying on back, on stomach, sitting up, etc.)?
Describe your masturbation routine, technique, etc.
What do you masturbate to (porn, smut, imagination, etc.)?
Have you ever masturbated to the point you got sore?
Your thoughts the first time you got up close and personal with the opposite set of genitals?
Have you ever “compared” (genitals, breasts, whatever) with a friend?
What kind of underwear do you normally wear?
Have you ever had a wet dream/orgasmed in your sleep?
Does your penis curve at all?
Which testicle hangs lower?
Are you circumcised or no? Are you happy with it?
What are you more into (or like more about yourself), boobs or butts?
Do you find genitals physically attractive, or weird/gross, or not feel strongly either way?
Do you like the way your genitals look?
Would you be able to pick out your genitals from a lineup?
What do you do with your pubic hair (shave, trim, wax, nothing, etc.)?
Do you care/have a preference what partners do with their pubic hair?
Do you tuck your penis a certain way (i.e. left or right) when you get dressed?
Do you have or want any genital piercings? Do you like any on other people?
What is the quickest you’ve ever brought yourself (or been brought) to orgasm?
Do you ever “edge” (repeatedly stop and start) when masturbating?
What’s the longest masturbation session you’ve had? Longest sex session?
What’s the most orgasms you’ve had in one session (of anything)?
Do your orgasms tend to be full-body, or crotch-centric?
When you ejaculate, do you more shoot or dribble?
Have you ever attempted (or succeeded) to give yourself oral?
Have you ever given/received a footjob, boobjob, etc.?
Have you ever had sex in a public place?
Have you ever had sex in a bed/on a couch that didn’t belong to either of you?
Have you ever had sex/masturbated while somebody was sleeping near you?
How many rooms of your house/apartment/etc. have you had sex in?
Strangest/most unique place you’ve had sex? How about masturbated?
Have you had any sexual experiences that were downright gross?
Are you particularly “vocal” when masturbating/having sex?
Have you ever been caught masturbating/having sex?
Have you had or do you want to have a threesome (or foursome, or more)?
Have you ever used a homemade sex toy, or a regular object as a sex toy?
What are your favorite positions?
Your most embarrassing sexual experience?
Worst place/time you’ve ever gotten a boner?
Have you ever had any genital injuries?
Have you ever had a sexually transmitted infection?
Do you think you’re “good” at sex, or your performance/skill could use improvement?
Have you “sexted” (whether through text messaging or IM chat)?
Have you masturbated for or with someone via webcam?
If you had the opposite set of genitals for a day, name 5 things you would do.
What’s something you like about your body?
What’s something you dislike about your body?
What body parts do you find the sexiest?
What was your most recent sexual thought?
When was the last time you touched your genitals?
Do you often imagine people naked?
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