I’ve seen a lot of these floating around, but none of them seem to get check every box. I’ve attempted to create my own Ask list and try to include as many things as I could think of. Simply pick a category and a number to ask that question. For example, message “masturbation 3 and 5.” On that note, enjoy 500 NSFW asks.
What is the size of your penis/breasts?
Does your penis have a curve?
Have you ever had an STD?
Have you ever been pregnant/gotten someone pregnant?
What type of underwear are you wearing?
What is your favorite type of underwear?
When was your last erection/arousal?
Have you ever had an erection which someone noticed?
Has anyone seen your private parts other than yourself?
Explain your ultimate fantasy.
What is the strangest thing you’ve ever been turned on by?
Have you sent a sexual ask to someone on tumblr (Anonymously or Not)?
Have you sent a nude photo or video to someone?
Did it include sexual acts?
Have you ever posted a picture of image of you in the nude on a website?
Did it include sexual acts?
Have you ever anonymously sent/posted a picture or video of yourself in the nude?
Did it include sexual acts?
If someone you knew asked for a nude image, would you do it? What about a tumblr follower?
What was your latest sex dream about?
Have you ever had a sexual fantasy about someone?
Was it about anyone other than your lover?
What was the last fantasy about?
Have you ever fantasized about someone older/younger than you? How much older/younger?
Have you ever told any of these people that you fantasize about them?
Do you have a favorite person or few people to fantasize about?
How often do you fantasize about other people?
Have you ever showered with someone?
Have you ever confessed you were aroused by someone?
Are you open about your sex-life and sexuality?
Have you ever played “7 minutes in heaven”? Explain the experience.
Have you ever played “spin the bottle”? Explain the experience.
Have you ever played “Truth or dare”? Explain the experience.
Have you ever played strip poker/strip beer pong/etc?
Do you shave your pubic hair?
Have you ever had your pubic hair shaved?
Do you prefer clean shaven or unkept?
What is your favorite type of underwear for the opposite sex?
How much lingerie do you own?
Whats your favorite lingerie outfit?
Do you like the way your genitals look?
Are you comfortable naked?
How old were you when you first masturbated?
How often do you masturbate?
When is the last time you masturbated?
Do you masturbate to any stimulus?
What is the last thing you thought of or masturbated to?
Have you walked in on or caught someone masturbating?
Have someone ever walked in on or caught you masturbating?
Have you ever had cyber sex?
Have you ever had phone sex?
Have you ever had a wet dream?
What is your method of masturbation? (i.e. Hands/Toys/Lotion/etc.)
Are you loud or quiet when you masturbate?
Has anyone ever watched you masturbate live online?
Has anyone ever watched you masturbate in person?
Have you ever masturbated with someone? (Mutual masturbation)
Have you ever watched someone masturbate live online?
Have you ever watched someone masturbate in person?
Have you ever masturbated to someone?
Who do you like to think about when you masturbate?
Have you ever told them you think about them while you masturbate?
Whats your most embarrassing masturbation story?
Whats your funniest masturbation story?
Have you ever used something unique or strange to masturbate?
Is it easy for you to orgasm or do you have to work for it?
Whats the easiest way for you to get off?
Is there only one way you can get off? (i.e. Vaginal/Clitoral/Toy Use)
Does anyone know you masturbate? How did they find out?
Have you masturbated because your partner wasn’t around to help? Where were they?
Have you ever masturbated to a fictional character?
Are you able to achieve orgasm through only non-conventional or indirect methods? (Breast Play/Hands-Free/Anal)
What is the strangest object you’ve used to masturbate vaginally or anally?
Do you ever double penetrate while you masturbate?
Do you ever suck on a dildo while you masturbate?
Do you edge when you masturbate? (Get to the point of orgasm and stop repeatedly to enhance the experience)
What position do you typically masturbate in?
Describe a typical masturbation session.
How often do you usually last?
Whats the quickest you’ve ever been brought to orgasm?
What’s the longest masturbation session you’ve had?
What’s the most amount of times you’ve cum in a day?
Are you straight/bi/gay/etc?
How many relationships have you been in?
What has been your longest relationship?
How old were you when you had your first relationship?
Have you ever been in a long distance relationship?
Have you ever used an online dating site?
What do you look for in a partner?
What do you look for in a hookup?
Have you ever had a one-night-stand?
Have you ever been a booty call?
Have you ever had a booty call?
Have you ever had a friend-with-benefits?
Have you ever cheated on a partner? Explain.
Have you ever been cheated on? Explain.
Would you ever be in an open relationship? Have you?
How often do you watch porn?
What is your favorite category?
When is the last time you watched porn and what was it?
How do you feel about hentai (Anime Porn)?
How do you feel about gang-bang porn?
How do you feel about cumshot porn?
How do you feel about lesbian porn?
How do you feel about amateur porn?
How do you feel about cuckold/cuckqueen/swinging porn?
How do you feel about threesome porn?
How do you feel about teen porn?
How do you feel about Japanese/Asian porn?
How do you feel about mature porn?
How do you feel about ebony porn?
How do you feel about bondage porn?
How do you feel about masturbation/solo porn?
How do you feel about rough/violent/humiliating porn?
How do you feel about BBW porn?
How do you feel about orgy/party porn?
How do you feel about trans/shemale porn?
How do you feel about POV porn?
How do you feel about blowjob porn?
How do you feel about bukkake?
How do you feel about extreme porn?
Have you ever tried to recreate a scene?
Have you ever used porn to show a partner what you like/want?
Has a partner ever used porn to show you what they like/want?
Who is your favorite pornstar(s)?
Have you considered getting into porn?
Have you considered being a webcam performer?
Have you watched cam girls?
Do you have a favorite cam girl?
Have you ever watched porn with a partner? Describe the experience(s).
Have you ever watched a cam-show with a partner? Describe the experience(s).
Have you ever performed in a cam-show with a partner? Describe the experience(s).
Have you ever been to a strip club?
Do you frequent strip clubs?
Do you have a favorite strip club?
Do you have a favorite stripper/dancer?
Do you get lap dances or just watch the performances?
Whats your best strip club experience?
Most embarrassing strip club experience?
Funniest strip club experience?
Have you ever orgasmed from a lap dance? Describe the experience(s).
How old were you when you lost your virginity?
If you haven’t, when would you like to?
Explain your first time in detail.
How many sexual partners have you had?
Who was your best sex partner?
Did you tell someone after you lost your virginity? Who?
Have you received oral sex?
Do you prefer to give or receive oral sex?
Have you had anal sex? How was your first experience?
Do you have any friends you would hookup with?
Have you wanted to have sex with someone, but couldn’t? Why couldn’t you?
Do you like dirty talking?
Do you like being called names?
Do you like being called obscene names? (Bitch/Slut/Whore/Sissy/etc)
Are you loud or quiet in bed?
Whats your favorite position?
Have you ever invented a position?
Whats the strangest position you’ve tried?
Have you ever been caught or walked in on while fucking?
When is the last time you had sex? Describe the experience(s).
When is the last time you received oral? Describe the experience(s).
When is the last time you gave oral? Describe the experience(s).
When is the last time you had anal sex? Describe the experience(s).
Which celebrities would you want to have sex with?
Any fictional characters you want to hookup with?
Have you ever had shower sex? How was it?
What is your favorite position(s)?
Where is the strangest or wildest place you’ve had sex/oral?
Have you ever broken up with someone because they couldn’t satisfy you?
Have you used anything to improve sexual performance? (Penis Extenders/Tingling Lube/Cock Rings)
Whats your most embarrassing sexual experience?
Whats your funniest sex experience?
Have you ever had any performance issues? What were they?
Are you on birth control?
Have you ever faked an orgasm? Describe the experience(s).
Can other people get you off?
Is there only one way you can cum? (i.e. Clitoral Stimulation Only/Anal Only/Toy/Specific Position)
Have you ever been rejected? Have you ever rejected someone?
Have you ever been stopped mid-sex? Describe the experience(s).
Have you ever had sex outdoors? Describe the experience(s).
Have you ever had sex in public? Describe the experience(s).
Have you ever had sex in front of others? Describe the experience(s).
Have you ever had sex in a car? Describe the experience(s).
Have you ever given or received road head? Describe the experience(s).
Have you ever had sex/oral/manual sex in a movie theater? Describe the experience(s).
Have you ever had sex in a fitting room? Describe the experience(s).
Have you ever had sex in a plane? Describe the experience(s).
Have you ever had sex at work? Describe the experience(s).
Explain your best sex experience in detail.
Which non-genital parts of your body do you like being touched or stimulated?
Do you ever take pictures or videos when you have sex? Explain the experience(s).
Have you ever given a strip tease to a partner?
Have you ever given a lap dance to a partner?
Have you ever received a strip tease from a partner?
Have you ever received a lap dance from a partner?
Have you ever “titty-fucked” before?
Has someone ever “titty-fucked” your breasts?
Do you prefer your partner to be vocal/moan loudly?
Do you enjoy having your nipples played with?
What situations or themes have you role-played?
What would you like to role-play?
Do you role play with costumes?
Do prefer lingerie in the bedroom?
What would you like to improve about your sex life?
Have you ever gone into public with hickeys? Did you know they were there?
Have you ever had a threesome? Describe the experience.
Would you like to have a threesome?
Who would you like to have a threesome with?
Would your partner be okay with a threesome?
Would you like to be with two men at the same time?
Would you like to be with to girls at the same time?
Would you like to be with more than two girls at the same time?
Would you like to be with more than two guys at the same time?
Have you ever been double penetrated? Describe the experience(s).
Have you ever had every hole filled or been involved with filling each hole? Describe the experience(s).
Have you ever tried ’69’? Explain the experience.
Do you like cum or is it gross?
Have you ever tasted cum? Do you like it?
Where is your favorite place to cum or receive cum?
Have you ever had sex while on a period/with someone on a period?
Do you listen to music while you have sex? What kind?
Have you ever used a buttplug while having sex?
Have you used any form of sex furniture? What kind?
Have you ever brought toys into the bedroom with a partner? What kind? Describe the experience(s).
Do you like to have your ass eaten?
Have you ever anally fingered your partner?
Do you like prostate play?
Is it gay for a man to enjoy anal stimulation from a woman?
Have you ever experienced a prostate orgasm?
Have you ever double penetrated/been double penetrated with the assistance of a toy?
Have you ever experimented with the same sex? Describe the experience(s).
Do you prefer sex with a man or with a woman?
Have you ever had sex with another couple(s) monogamously? (Not touching the other couple(s))
Have you ever watched another couple have sex?
Have you ever gotten cum in your eye?
Has anyone ever cum inside you on accident? How did you feel about that?
Have you ever cum inside someone on accident? How did they respond?
Have you ever cum in your pants? Describe the experience(s).
Do you like to play with balls/have your balls played with?
Are hand jobs boring or are they underrated?
Describe your average orgasm.
Describe your average cumshot.
Whats the quickest you’ve ever been brought to orgasm?
Whats the quickest you’ve ever brought someone else to orgasm?
How long are you usually able to last?
What’s the most times you’ve had sex (or sexual contact with a partner) in a day?
Whats your longest sex session?
Have you ever bought a sex toy?
What is the last sex toy you bought?
What sex toy do you currently want?
Would you let someone buy you a sex toy?
How many toys do you own?
What kind of toys do you own?
What is your favorite toy?
Have you ever used a washer/dryer as a sex toy?
Have you ever used a shower head as a sex toy?
Have you ever used a pocket pussy or Fleshlight?
Have you ever improvised a sex toy? (Cucumber/Banana/Etc.)
What is the strangest sex toy you’ve ever used?
What is the strangest improvised sex toy you’ve ever used?
Do you prefer sex toys or the real thing?
Do you own any buttplugs?
Do you ever wear a buttplug in public?
Do you have any vibrating panties?
Do you ever wear vibrating panties in public?
Do you like nipple clamps?
What fetishes do you have?
What is your favorite fetish?
Have you indulged in all your fetishes?
What fetishes are you yet to experience?
Are there any fetishes you don’t have yet, but may be interested in?
Have you experienced BDSM? Do you practice it?
Are you a top/dominant a bottom/submissive or a switch?
What is it about BDSM that you like?
Have you experienced being tied up or restrained? Describe the experience.
Have you experienced rope play? Describe the experience.
Do you enjoy long, extended teasing/edging sessions?
What is the longest you’ve been teased/edged?
Do you enjoy tease and denial?
Do you like to be denied?
Do you have a panty fetish?
Have you ever purchased panties from a woman online?
Have you ever used panties to masturbate? (Stuffing/Wrapping/Etc.)
Do you have a hosiery fetish?
Do you like spanking/being spanked?
What do you prefer to use to spank? (Paddles/Hands/Whips/Etc)
Do you like to hit or be hit? How hard?
Do you enjoy choking or being choked? How hard?
Do you like to bite or be bit?
Do you like to slap or be slapped?
Do you like pulling or having your hair pulled?
Have you ever done a cum-walk? (Walking in public with cum on your face/clothes/etc)
Are you an exhibitionist?
What was your best exhibitionism experience?
Would you like to watch your partner have sex with another person?
Would you like to have your partner watch you with another person?
Have you ever been cuckolded? Describe the experience
Explain your best cuckold experience
What is it about cuckolding that you like?
Do you like to be humiliated?
Do you like to humiliate your partner?
Do you like to be humiliated while cuckolding or do you prefer a friendly environment.
Do you like to be forced into crossdressing?
Do you like to be forced into feminization?
Do you like to be forced into sissification?
Have you ever fisted? Explain the experience.
Do you like extreme insertion? Have you ever experienced it?
Do you soft-swap or hard-swap?
Have you ever been to a swingers club (with a partner)?
Would you ever go to a swingers club (with a partner)?
Explain your best swinging experience.
Would you ever participate in an orgy? (4 or more people)
Would you ever participate in a gang bang? (4 or more people)
Have you ever pegged/been pegged? Describe the experience.
What is it about pegging that you like?
Describe your best pegging experience.
Do you enjoy large strap on dildos or smaller?
Do you enjoy sucking or having your strap on sucked?
Have you ever experienced incest?
Do you like face-sitting/smothering?
Do you have experience in face-sitting/smothering?
Do you like forced cum eating?
Have you experienced rape play?
Do you like to be dominated?
Have you ever been dominated online?
Whats the most humiliating thing you’ve been forced to do?
Do you like daddy dom/little play? Describe the experience(s).
Do you like to be worshiped?
Do you like to be spit on or spit on your partner?
Do you like to keep the slave play in the bedroom or carry it over to real life?
Have you ever been suspended while having sex?
Do you like ball-busting/CBT (Cock and Ball Torture)?
Do you like to be told what to do?
Do you enjoy giving/receiving JOIs? (Jerk Off Instructions)
Describe your best JOI experience.
Have you ever given or received a foot job?
Would you ever swap cum with your partner?
Have you ever tried fetching? (Sucking cum from a partners anus or vagina after finishing)
Would you participate in a bukkake?
Have you ever participated in chastity?
What is the longest you’ve been locked up or forced a partner to be locked up?
Have you ever cum while in chastity?
Have you ever experienced a full friction/lap dance?
Have you ever cum or made someone cum from a full friction lap dance/grinding?
Do you enjoy outercourse/hotdogging/pussyjobs?
Do you enjoy cumming or watching someone cum over strange objects?
What is the strangest way anyone has made you cum?
What is the strangest way you’ve made anyone cum?
Do you enjoy forced cum eating?
Do you enjoy premature ejactulation?
Have you ever experienced a ruined orgasm? Describe the experience(s).
Have you ever had your prostate milked or milked a prostate?
What feels better, masturbation or sex
Rough Sex or Intimate Sex
Cum on Tits or Cum in Mouth
Cum on tits or Cum on Ass
Cum on Tits or Cum on Belly
Vaginal Creampie or Anal Creampie
Circumcised or Uncircumcised
Ruined or Complete Orgasm
Vaginal or Clitoral Orgasm
Prostate Orgasm or Regular
Grinding Orgasm or Titty-Fucking Orgasm
Be Humiliated or Worshiped
Lace Panties or Cotton Panties
Silicone Dildo or Glass Dildo
Real Cock or Sex Toy Cock
Real Pussy or Fleshlight/Pocket Pussy
Dirty Talk or Loud Moaning
Faked Orgasm or Premature Ejaculation
Cum on Clothes or Cum in Hair
Thigh Gap or Thick Thighs
Prostate Orgasm or Frenulum Orgasm
Anal, Clitoral or G-Spot Orgasm
Big Ass or Tight, Toned Ass
Sex on the Beach or Sex on a Plane
Sex in Public or Sex in a Car
Vibrating Panties or Butt Plug
Nipple Stimulation or Neck Stimulation
Realistic Dildo or Smooth Dildo
Giving Head or Receiving Head
Getting Anal or Giving Anal
Pussy and Anal Penetration or Ass and Mouth Penetration
Reverse Gang Bang or Male Gang Bang
Doggy Style or Missionary
Cowgirl or Reverse Cowgirl Â
Cum On Someone or Be Cummed On
Veiny Dick or Curved Dick
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