What tends to feel better for you, sex or   masturbation?
Your 5 favorite spots to be stimulated.
Have you ever had an orgasm from anywhere   other than your genitals?
Do you prefer clitoral or vaginal stimulation?
Can you touch your clitoris directly, or does   that hurt?
Have you masturbated for or with someone via   webcam?
Are you well-acquainted with your G-spot?
Do you like having your nipples touched?
Do you like having your anus touched?
Have you ever been fisted (anally or   vaginally)?
Do you like mild roughness (scratching, Â Â 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?
Whatâs the most unusual thing youâve 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? Â Â 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.)?
What was your most recent sexual thought?
Do you ever just play with your boobs, labia, Â Â 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 âcomparedâ (genitals, Â Â breasts, whatever) with a friend?
What kind of underwear do you normally wear?
Have you ever had a wet dream/orgasmed in your   sleep?
How big are your breasts?
How big are your nipples?
Do you have long or short labia? Are they even   or uneven?
Do you have a particularly large or tiny   clitoris?
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?
What do you do with your pubic hair (shave, Â Â trim, wax, nothing, etc.)?
Do you care/have a preference what partners do   with their pubic hair?
Do you have or want any genital piercings? Do   you like any on other people?
What is the quickest youâve ever brought   yourself (or been brought) to orgasm?
Do you ever âedgeâ (repeatedly stop   and start) when masturbating?
Whatâs the longest masturbation session youâve   had? Longest sex session?
Whatâs the most orgasms youâve had in one   session (of anything)?
Do your orgasms tend to be full-body, or   crotch-centric?
Have you ever had sex in a public place?
Have you ever had sex in a bed/on a couch that   didnât 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. Â Â have you had sex in?
Strangest/most unique place youâve had sex? Â Â How about masturbated?
Have you had any sexual experiences that were   downright gross?
Are you particularly âvocalâ 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?
Have you ever had any genital injuries?
Have you ever had a sexually transmitted   infection?
Have you ever had a non-sexually transmitted   genital infection (yeast infection, etc)?
If you donât have a penis, have you ever tried   to pee standing up?
If you donât have a penis, how familiar are   you with how you look down there?
Do you think youâre âgoodâ at sex, Â Â or your performance/skill could use improvement?
Have you âsextedâ (whether through   text messaging or IM chat)?
If you had the opposite set of genitals for a   day, name 5 things you would do.
Whatâs something you like about your body?
Whatâs something you dislike about your body?
What body parts do you find the sexiest?
When was the last time you touched your genitals?
Do you often imagine people naked?
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