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500+ Freaky Questions to Ask a Girl – The Master List

500+ Freaky Questions to Ask a Girl – The Master List

Updated on May 17, 2022 | Published on Nov 17, 2021

Reviewed by Julianne Cantarella, MSW, LSW , Certified Relationship Coach

500+ Freaky Questions to Ask a Girl - The Master List

Knowing each other inside and out is never a terrible idea, whether you’re just a crush, a girlfriend, or in the early stages of a relationship.

In fact, every person must do it early enough before anything important happens in order to avoid small disappointments that are common in the early stages of any relationship.

There’s no better way to get to know the person you’re falling for than to ask them questions and receive their honest opinions. Therefore, freaky questions to ask a girl are the right way to go.

And, if you want to learn about their other side (the freaky side), you need to ask the proper set of freaky questions at the right time.

Whether you choose dirty truth or dare questions, dirty would you rather questions, sensual never have I ever questions or naughty who’s likely to ask questions for couples, make sure they’re the proper set of questions for her and that the moment is perfect.

If you want to know what dirty things a girl likes, here’s a list of freaky questions to ask her.

500+ Freaky Questions to Ask a Girl - The Master List
500+ Freaky Questions to Ask a Girl – The Master List

Freaky questions to ask your girlfriend

Want to have some freaky or dirty conversation with your girlfriend? If that’s the case, you’ve come to the correct place.

If you are feeling distant from yourself, want to spend some quality time, play drinking games or simply want to make your love bond stronger, then below is the desired list of freaky or dirty questions to ask your boyfriend or girlfriend at night or being alone. 

1. Do you prefer to be the dominant or submissive partner in the bedroom? Or do you prefer something else? 

2. Do you want to be a member of a trio? Have you ever had sex in front of a crowd?

3. Have you ever given something to one of your previous boyfriends in exchange for a sexual favor?

4. Have you ever 69’d a guy who was still standing? Or don’t have any interest in this? 

5. Have you ever recorded yourself having sex with another person? Or have you ever clicked photos? 

6. Do you enjoy having naughty conversations in bed? Or sweet and soft conversation is your preference?

7. When you’re having a sexual act with a guy, how long can you hold your orgasm most reliably?

8. Have you ever dreamt about another man while in bed with one? Or have you never thought of anyone else? 

9. Tell me about the most daring thing you’ve ever done in bed. What type of lingerie do you prefer?

10. What would you do if you were here with me right now and could do anything with me, and why?

11. Do you sleep in your pajamas, lingerie, or in your underwear? Do you ever sleep in your underwear?

12. Where would you kiss a man if you had to kiss him anywhere other than his face? Neck, hands, feet or back? 

13. What would you do if you happened to run into me while I was naked? Would you like to see me like this? 

14. Do you think girls love having the lights on or off when you’re in bed? 

15. Have you ever considered having sex in the presence of a mirror? Or you don’t want to see yourself like this? 

16. Do you prefer it when I’m shy and sexy or when I’m bold and sexy? And why? 

17. Do you prefer your man to be rough and aggressive in bed or delicate and kind? And why? 

18. Who would you pick as part of a threesome with another guy and me, and why? 

19. If you had the chance, what sexual desires would you like to attempt with me?

20. What area of my body works as the biggest turn for you? And why? 

21. Have you ever cried while having sex? What was your feeling after making out? 

22. Have you ever fallen off during a sexual encounter? If so, then why? 

23. Would you take advantage of me if we were only friends right now and I was drunk with you, or would you be a gentleman and drop me home?

24. If we were on vacation and having sex in a hotel room, and you suddenly learned a man was observing us from his room window, would you stop or continue having sex?

25. Would you be embarrassed if I caught you masturbating and asked you to stop or would you finish your task until you were satisfied?

26. Do you enjoy having your back kissed? Or do you like to be kissed somewhere else? 

27. When did you have your first sexual experience? When did you first start masturbating?

28. Have you ever had a sexual attraction to a friend’s boyfriend? How did you feel that time?  

29. When it comes to sex, what position do you prefer? Do you enjoy having sex while swimming?

30. What are some things you will never do in bed? Are you a fan of pornographic films?

31. Do you want to go see a pornographic film with me? Will it pique your interest?

32. What is your favorite bedtime activity? Do you have an unfinished sexual fantasy?

33. What part of your body do you prefer to be kissed the most? And why so? 

34. Do you prefer to provide or receive oral sex? In bed, what excites you the most?

35. If given the opportunity, would you desire to have sex with numerous men at the same time?

36. If given the opportunity, would you participate in an orgy? Do you have any voyeurism fantasies?

37. When did you lose your virginity and at what age? Can you tell me how you feel after that? 

38. What is your least favorite sexual position, and why? And what position would you like to enjoy most? 

39. Have you ever cheated on someone sexually in your life? Who are you going to be with?

40. Have you ever slept with a close friend’s boyfriend? If so, then why? 

41. Do you enjoy having sex while drunk or on drugs? Or do you want to give it a try? 

42. What do you like to do after a good night’s sleep? What is your desire for the same? 

43. What is the best aphrodisiac in bed, in your opinion? And why do you think that? 

44. Have you ever had a romantic encounter in the open air? If not then why? 

45. What is the weirdest pornographic film you have ever seen? Did you enjoy it? 

46. Do you have any abnormalities or preferences when it comes to sexual activities? Or are you a person who fully enjoys it? 

Freaky questions to ask your crush

Do you like someone but are afraid to talk to start a conversation? Then this section is for you.

Whether you like someone who doesn’t know you or you like your friend whom you are really frank with, then here is the ultimate list of questions you can ask your crush when you both are talking alone. This will gradually help you to slide into her heart and connect on a deeper level. 

47. Has it ever occurred to you to have homosexual fantasies? Or, do you never want it? 

48. Would you do it if I asked you to touch yourself while I watched you do it? 

49. On a scale of one to ten, with one being the least sexual and ten being the most sexual, how sexual are you?

50. Do you masturbate on a regular basis? Do you ever consider anyone other than me when you’re doing it?

51. Have you ever had a car romance? Where do you like to make love the most?

52. What part of your body do you hate having sex in? 

53. Have you ever been caught having sex or making out with an inanimate object by your parents? Have you ever walked into your parent’s room and caught your parents having sex?

54. In terms of sexual adventure, how daring are you? Do you have any sexual fantasies?

55. What’s the dirtiest sexual fantasy you’d like to see come true soon? And which one do you not really want to come true? 

56. Do you prefer delicate, pleasant sex or brutal, forceful sex? And why?

57. Do you like BDSM? If that’s the case, are you a dominatrix or a submissive?

58. Tell me about a strange sexual experience you’ve had. Can you explain it to me?

59. Tell me about the most memorable sexual experience you’ve ever had. And why?

60. Have you ever entertained sexual fantasies about a family member? And why so?

61. Have you ever had or considered having sex with a cousin or other close relative?

62. Have you ever had sex in a restaurant or a bar?

63. Have you ever kissed a woman or a girl? Do you want to do it?

64. What gets you going in the morning and what gets you down in the evening?

65. Do you think the guy on your left or the guy on your right spends more time in the mirror?

66. How would you react if you discovered your parents were not monogamous?

67. Have you ever had a lap dance performed for you?

68. Have you ever had someone tell you that they loved you and you didn’t feel it? Who is the love of your life?

69. Would you sell a pair of underpants to someone you don’t know?

70. Would you eat your partner’s dinner even if it was disgusting?

71. Where have you masturbated in the most public places?

72. Have you ever returned home with someone you don’t like?

73. What was your mother’s first reaction when you told her you were gay?

74. What would you do if you found yourself in this situation? Is there someone who is too high or too drunk?

75. Is the person with whom you lost your virginity the same person with whom you lost your virginity?

76. What is your favorite position on the field?

77. How many different relationships have you had?

78. When was the last time you had a nice massage from a professional?

79. Have you ever considered whether or not you have a drinking problem?

80. Have you ever been on a date and felt stupid?

81. How do you deal with someone who approaches you hate the fact that you are not attracted to them?

82. Have you ever done it in front of others?

83. What is the most unusual place you’ve ever had sex?

84. Have you ever tried whipped cream in your bedroom?

85. Which aspect of sex do you find the most pleasurable?

86. Have you ever had a dirty phone conversation?

87. Have you ever gotten on a boat and made it out there?

88. Who was the youngest person with whom you have had sexual relations? At the time, how old were you?

89. Which portion of my body do you prefer to kiss? And why?

90. If we were alone right now, what would you do with me? And why?

91. Which celebrity nude/semi-naked photos are your favorite? Who is your dream girl?

92. What was your mother’s first reaction when you told her you were gay?

93. Is there anything you’ve always wanted to know about me but were too afraid to ask?

94. Which portion of your body do you think is the most attractive?

95. What are your plans for my body? Can you tell me about it?

96. Who would you have on your show if you were Ellen DeGeneres for a day?

Freaky 21 questions to ask a girl 

Here is the small question list of 21 questions that you can ask a girl. Let’s delve deep into these simple yet interesting question games to ask your crush, girlfriend, or wife. 

97. Have you ever considered trying a glory hole? What was your experience?

98. Should marriages have expiration dates that can be extended? And why so?

99. Have you ever been in a trio? Do you think you’d like to have one?

100. Would you like to know what my most violent sexual fantasy is? Or you are not interested in it?

101. What is the most outrageous thing you’ve ever done? How was your experience?

102. During your most recent sexual encounter, did you or the guy perform better?

103. Agree or disagree: People are overly concerned with social media.

104. Where have you masturbated in the most public places? And why?

105. Describe the experience of having oral sex with a bearded gentleman.

106. Make a drawing that brings you joy. Would you like to tell me about it?

107. Is it easier to orgasm if you have a larger clitoris? What are your thoughts?

108. Tell me about the most insane thing you’ve ever done.

109. What is the longest friendship you’ve ever had? What if I begged your friends?

110. How long does most people’s intercourse usually last?

111. What was your most embarrassing experience? 

112. Is there something you wish you had but don’t? And why?

113. Have you ever had a hidden boyfriend or girlfriend? And why? 

114. Have you ever had sex so good that it woke up your neighbors?

115. How do males fake orgasms — isn’t the fact that they don’t ejaculate a dead giveaway?

116. In an ideal world, how often do you believe humans should have sex?

117. Who would win The Hunger Games in this circle?

Freaky would you rather questions to ask a girl

Would you rather questions are the best conversation starters that help to keep the conversation going with fun and engagement.

This is quite fun to ask such questions and delve deep into each other’s life. So let’s take a look at the best possible deep questions to ask a girl. 

118. Would you rather have uncontrollable gas for a month or have to go to work soaked?

119. Would you rather get paid $5,000 or make out with your famous or rich crush?

120. Would you rather go shopping in your underwear or go to the beach naked?

121. Would you rather prefer to sleep with your partner’s siblings or a sibling from one of your best friends?

122. Would you rather have ordinary sex every day for the rest of your life or fantastic sex once a year?

123. Would you rather want to have sex with a different person each year or with the same person for the rest of your life?

124. Would you rather want to drink a glass of puke once or burp every time your name is called?

125. Would you rather have sex with your parents or have sex with your parents?

126. Would you rather prefer a job promotion or sleeping with your attractive coworker?

127. Would you rather wear your mother’s clean underwear for a day or wear the same pair of underwear for a week?

128. Would you rather want fluorescent pubic hair or pubic hair that is extra-long?

129. Would you rather have your genitals exposed to your neighbors or send a hot text message to a relative?

130. Would you rather have sex with any one of your choosing or a threesome with two strangers?

131. Would you rather have your best friend spit in your mouth or lick the bottom of a stranger’s shoe?

132. Would you rather have gorgeous boobs or perfect butts, ladies?

133. Would you rather be good at sex but have a bad body figure or awful at sex but have a good body figure, men?

134. Would you rather prefer a sexy naked photo or a sexy text message?

135. Would you rather have your pet lick peanut butter off your nipples or lick peanut butter off your best friend’s nipples?

136. Would you rather have an orgy with random strangers or have sex with all of your ex-boyfriends and girlfriends?

137. Would you rather prefer losing your sexual organs or gaining 80 pounds (that you can’t lose)?

138. Would you rather prefer a sexy naked photo or a sexy text message?

139. Would you rather be caught cheating on your lover or be cheated on and never know?

140. Would you rather have an orgy with random strangers or have sex with all of your ex-boyfriends and girlfriends?

141. Would you rather want to eat a chocolate bar that tastes like mold or a lump of mold that tastes like chocolate?

142. Would you rather prefer losing your sexual organs or gaining 80 pounds (that you can’t lose)?

143. Would you rather prefer to wear lingerie every day or never wear a bra again, ladies?

144. Would you rather prefer melting chocolate or whipped cream in your kinky sex?

145. Would you rather be slapped in the face every time you had a sex-related thought or sneeze nonstop while having sex?

146. Would you rather have balls under your chin or forks for your fingers?

147. Would you rather choose pubic hair that regrows five times faster or a micropenis?

148. Would you rather want to be caught having sex at work or to have your supervisor watch you have sex?

149. Would you rather prefer to live in the Playboy Mansion or at a strip joint?

150. Would you rather make out for 10 seconds with your biggest crush or ten minutes with your best friend’s brother?

151. Would you rather suffer bad acne for 6 months or smell like body odor for a year?

152. Would you rather spend a year of sex with your clothes on or never see your mate fully naked?

153. Would you rather have a lifetime of truly exciting sex or a lifetime of romantic sex?

154. Would you rather kiss a stranger in the dark or make out in public?

155. Would you rather prefer to have sex with Queen Elizabeth or with Hillary Clinton?

156. Would you rather prefer being in a relationship with someone who has a sex addiction or someone who has a low sex drive?

157. Would you rather like your sexual partner to talk about disgusting things or be entirely silent during sex?

158. Would you rather want C-cup man boobs or a 2-inch penis, men?

159. Would you rather have sex with the #1 charting artist once or have to perform the #1 charting song every time you have sex?

160. Would you rather prefer bad breath or stinking ear wax?

161. Would you rather prefer to date someone who won’t kiss you or someone who won’t give you oral sex?

162. Would you rather prefer to commit the act while shackled or blindfolded?

163. Would you rather your partner cry uncontrollably or laugh uncontrollably anytime they see you naked?

164. Would you rather prefer to have sex in a horrible smell restroom or a soiled bed?

165. Would you rather want your Instagram followers to see your nudity or your grandparents?

166. Would you rather prefer to hook up with your boss or your doctor?

167. Which would you prefer: sex in a car or sex in a tent?

168. Would you rather compete in a wet t-shirt contest or perform a lap dance for someone?

169. Would you rather prefer a glass of urine or a teaspoon of poop?

170. Would you rather get a racy letter in the mail or send a racy text message? Have you ever accidentally sent a dirty message to someone?

171. Would you rather kiss your celebrity crush or have a social media following of over a million people?

172. Would you rather have a dirty conversation with the person to your left or the one to your right?

173. Would you rather want to be able to masturbate every day for the rest of your life or never be able to masturbate again?

174. Would you rather develop urethritis every time you have sex or never be able to ‘finish’?

175. Would you rather have your parents find you masturbating or catch your housemate masturbating?

176. Would you rather want to have a single partner or a group of partners?

177. Would you rather prefer to have sex with your best friend or date your best friend?

178. Would you rather cheat on me or bring another person into bed with you?

179. Would you rather want to do something romantic or try out some fresh kooky ideas?

180. Would you rather prefer to end a first date with a passionate kiss or with sex?

181. Would you rather want to be caught cheating or do you want to catch your spouse cheating?

182. Would you rather your significant other sleep with your best friend or with his or her best buddy?

183. Would you rather prefer your spouse to date one of your best friends or one of your arch enemies?

184. Would you rather confess your crimes in front of your children or do you prefer to do the crime in front of your children?

Freaky 21 questions game to ask a girl

Here is a small list of 21 questions that you can ask a girl. Let’s delve deep into these simple yet interesting questions to ask your crush, girlfriend or wife for playing this game. But these are not ideal questions for kids.

185. Have you ever been attracted to a lady sexually? Can you tell me about it?

186. Describe a time when you raised your voice to a higher pitch.

187. What do you believe the present greatest threat to marriage is?

188. Make a drawing of how you see yourself. And why do you think so?

189. Do you agree or disagree with this statement: People take social media far too seriously?

190. During your most recent sexual encounter, did you or the guy perform better?

191. What is the maximum number of times you’ve had sex before your dick hurts?

192. Have you ever been referred to as “tight”? If so, then why?

193. Have you ever had your ass pinched by a stranger?

194. Which fruit do your balls resemble the most? 

195. In your personal relationship, what gay couple do you aim to be like?

196. Who was the last person to kiss you? Was there any significance to it?

197. Who can you make a convincing impression of?

198. Have you ever had your face slapped? How did you feel about that?

199. Have you ever removed a partner from your Facebook friends list after a breakup?

200. Where do you think you’ll have the best chance of finding a sexual partner?

201. Is there anywhere you’d never have sex? 

202. Do you have sex with your eyes closed?

203. When you’re having sex, what sounds do you make?

204. When practicing oral sex, do you use condoms?

205. What makes you horny when it’s not sexual?

Dirty freaky questions to ask a girl

Dirty questions are a way to go for intimate and open relationships. If you want to establish an intimate relationship then fun dirty questions can be the right way. This makes your partner aroused and makes her feel the same way you are feeling right away. 

Therefore, if you both are alone and feeling some sense of humor together then start with these sexual questions to ask s girl. Here is the list of dirty questions to ask a girl.

206. In bed, are you a dominant or a submissive? Or something else?

207. Did you even email anyone your naked photos? How is your love life going?

208. What portion of sex do you enjoy the most? And why?

209. Do you prefer hard sex or soft sex? And why so?

210. Have you ever participated in group sex? And why?

211. What is the most enticing thing you’d like to do before you die?

212. Have you ever slept with two men on the same night?

213. What is your favorite portion of a man’s body?

214. Do you like being in position 69? And why so?

215. How many penises have you sucked up to this point?

216. Do you enjoy using sex toys when sexting?

217. How often do you masturbate when having a dirty conversation with someone?

218. Which portion of your body do you enjoy the most?

219. Do you like to be on top or bottom? Or something else?

220. Have you ever met a guy who can turn you on in a matter of minutes?

221. Have you ever considered having sex with someone of the same gender?

222. Do you enjoy it when I bite your lips? Or did you not?

223. Do you like it when I slap your buttocks?

224. When you lost your virginity, how old were you?

225. Do you prefer sex with or without a condom? And why?

226. Is it true that thinking about me makes your boobs harder?

227. Which part of your body do you enjoy kissing the most?

228. On a scale of one to ten, how would you grade my penis?

229. Do you want to bring someone else into our sex life to spice things up?

230. Have you ever had sex with a man your father’s age?

231. If you had the chance to sleep with a celebrity, who would you choose?

232. What’s the weirdest thought you’ve ever had about someone you’ve never met?

233. Do you prefer to have sex at night, in the morning, in the middle of the afternoon, or RIGHT NOW?

234. If you had the chance, how would you sexually dominate your boss?

235. What do you do when you’re horny in public? And why?

236. Have you ever done your business in a public restroom?

237. What is the strangest thought you’ve ever had when touching yourself?

238. What’s the weirdest thing you’ve utilized to get yourself out of a jam?

239. Do you recall your first experience of being aroused?

240. Who was the first person to give you an orgasm?

241. Do you remember the feeling of your first orgasm?

242. Have you ever had sex with someone you didn’t know their name?

243. What do you like best about a quickie? How was your feeling?

244. What is the boldest thing you’ve ever done in terms of sexuality?

245. Do you ever fantasize about fucking one of your professors?

246. Do you ever mentally undress strangers for the sake of amusement?

247. Then think what it would be like to fuck them in every detail.

248. Have you ever kissed a man or a woman of the same gender?

249. What motivates you to take the initiative? And why?

250. What does it mean to be good in bed, in your opinion? Did you have any good feelings after that?

251. Have you ever been unable to stop yourself from cheating on a partner or girlfriend?

252. Have you ever pushed your loyalty to the limit and then backed down just for the thrill of it?

253. Do you have a go-to masturbation fantasy? 24. Do you have a go-to masturbation fantasy?

254. Have you ever had sex while closing your eyes? How did you feel?

255. Have you ever handcuffed or blindfolded a partner?

Freaky questions to ask a girl over text

Texting is the best way to communicate and express your emotions because sometimes it’s quite difficult to say words with which you are not comfortable. 

Therefore, nowadays text conversations are the best way to express feelings and tell your partner about your willingness. So, here is the ultimate list of naughty questions to text a girl. 

256. Are you sure about that, my dirty little sex queen from the woods?

257. What is the dirtiest thing you’ve ever heard someone say to you during sex?

258. Have you ever secretly observed another couple getting it on?

259. Have you ever witnessed a couple have sex with their consent?

260. What would you say if a couple asked you to be their “third” child?

261. What is the most flattering remark you’ve ever received regarding your naked body?

262. How long has it been since you experienced a vivid sex dream?

263. Can you imagine what an orgy might be like? 

264. Have you ever tried to seduce a complete stranger?

265. How would you describe your dream one-night stand?

266. On average, how long does it take you to get yourself off?

267. What is the strangest thing that makes you happy?

268. Have you ever had a bad dream concerning a close family member or friend?

269. Have you ever woken with your pillow humping?

270. When was the last time you had an amazing dream?

271. What has been the most humiliating experience you’ve had while hooking up?

272. Do you enjoy touching yourself in front of the individuals with whom you share your bed?

273. Can you tell me about the dirtiest SMS you’ve ever sent or received?

274. Which kind of pornography do you prefer: professional or amateur?

275. What’s your favorite way to do a blowjob?

276. Would you rather be a dominatrix or a submissive if you had to choose?

277. Is there anything in bed that you won’t do?

278. When did you get your first kiss, and how old were you?

279. When did you know you were so fond of me?

280. Would you like to add some spice to our sex life?

281. Do you enjoy receiving public kisses?

282. What part of a man do you admire the most?

283. Could you tell me about your most recent exotic dream, and if I was in it?

284. How frequently do you think about me when you’re having fun?

285. How do you feel about sex in public places?

286. What is your sexiest dress, and would you wear it to bed for me tonight?

287. Have you ever had a one-night stand? If so, how did it go?

288. When did you realize you wanted to have sex with me for the first time?

289. What is your favorite position, and would you like to see us try it out tonight?

290. Do you enjoy flirting with people via text messages or social media?

291. What is the naughtiest text you’ve ever sent, and how did it go over with the recipient?

292. Are you interested in trying out phone sex?

293. What is the most vulgar thing you’ve ever said during a sexual experience?

294. Which portion of your body is your favorite?

295. Where would you have sex if you could have it anywhere in the world?

296. Have you ever flirted with someone you didn’t know online?

297. I bought some lingerie for you and would like you to model it for me. Will you join us?

298. On a first date, how do you feel about sex?

299. What part of your body do you prefer being touched the most?

300. Outside of your home, where have you done it the hottest?

301. Which area of your body do you prefer for me to kiss?

302. What suggestions do you have for making our sex life more interesting?

303. Have you ever used food as a kind of foreplay?

304. How many males have you slept with, and how do they stack up against me?

305. What is it about sex that makes you feel the most at ease?

Freaky questions to ask a girl you like

If you like a girl then, there is no harm in asking freaky or flirty questions to know if she also likes you or not. If that girl is comfortable answering personal questions about any topic then why not flirt with her. 

Sometimes, this also helps to know her emotions and brings her closer to you. Let’s deep dive into the freaky funny questions to ask a girl you like. 

306. Do you like foreplay or getting right down to business?

307. Would you like us to act like complete strangers tonight and do something naughty?

308. Have you tried using props in the bedroom before, or do you wish to?

309. Do you enjoy having sex in the presence of another couple?

310. Do you want me to keep an eye on you while you enjoy yourself and then join you later?

311. Does it turn you on as much as it does me to do it in forbidden places?

312. Which part of my body do you prefer?

313. Do you mind if I leave you with hickies?

314. Do you enjoy watching me change my clothes? Would you tear my clothes while making love?

315. What’s your wildest fantasy about me, and do you want to make it a reality?

316. When you lost your virginity, how old were you?

317. May I borrow your hand for five minutes?

318. Do you appreciate it when I gently massage your entire body?

319. If you had to spend the rest of your life in one posture, what would it be?

320. What are your plans for me tonight?

321. What’s on your naughty bedroom bucket list?

322. Would you join me in the fitting room the next time I go shopping with you?

323. Does it turn you on to know that other people can hear us having sex? With how many people have you slept till now?

324. Would you mind sending me a sexy photo of yourself via text?

325. What would you do if you got home tonight and discovered me naked on your couch?

326. Which aspect of me do you find yourself missing the most right now?

327. What would we do if we just had 20 minutes together?

328. Would you put on your sexiest clothes and wait for me tonight?

329. How would you like me to assist you in relaxing if you’re stressed?

330. Do you want to tie me up tonight and do whatever you want with me?

331. How would you feel if you were forced to spend the night naked, chatting dirty, and forbidden from touching for an hour?

332. Does it make you sweat just thinking about me?

333. What would you have loved to see me in if I had to come in masked tonight?

334. Do you prefer it when I go slow or when I go fast and wild?

335. Do you consider yourself a naughty young lady? If you say yes, back it up with evidence.

336. How long should you wait between foreplay and sex?

337. What is the one activity you can’t stop yourself from doing, and it always gets you wet?

338. When do you prefer to have sex during the day?

339. What do you do if you become horny in public and don’t know what to do?

340. Do you recall the feeling of your first orgasm with me?

341. Describe how it feels to be inside you in great detail.

342. Have you ever had strange ideas about your boss? 

343. How do you feel about threesomes? And what was your experience so far?

344. Who would you invite to join us tonight if you could invite anyone from anywhere in the world?

345. Have you ever considered fucking one of my friends? And what is the reason?

346. Would you have sex with me in front of a camera?

347. Have you ever secretly watched another couple having sex? Is it true that it turned you on?

348. Have you ever tried out for an orgy? And what is the reason?

349. Is the prospect of fucking a complete stranger appealing to you?

350. What was the most awkward time you were aroused?

351. Do you prefer it when we both orgasm at the same time? Please describe how it makes you feel.

352. Do you enjoy it when I direct your actions? How did you feel?

353. Do you believe that sex without feelings is more appealing?

354. Do you have a bedtime line you never cross? And why?

355. How would you react if you were asked to be someone’s “third”?

Freaky sex questions to ask a girl

If you and your girlfriend want to spend some intimate time together, then sex questions are the right way to begin. This helps to arouse you both and brings your emotions to a peak. 

Therefore, we have curated the list of freaky sexy questions to ask a girl you really like or love. 

356. What is a proven strategy to turn you on in a matter of seconds?

357. Have you ever fucked a man in his forties or fifties? If so, how did it go?

358. Do you prefer males who are younger or older? And why?

359. Do you want to spend the entire week in your favorite sex position?

360. What could I do to you that would be the most orgasmic?

361. Who would you have sex with if you had to have sex with a celebrity, and where would you do it?

362. Would you make out with another female in front of me if I was watching?

363. What is the naughtiest thing you’ve ever done to your significant other?

364. What strange sex position do you want to try? And why do you want to do so?

365. Do you enjoy blowing people’s minds? Would you spit or swallow it?

366. What is the worst event that has ever happened in your bedroom to you?

367. Have you ever wanted to play a sexual role? And what is the reason?

368. Do you prefer to be cuddled after sex or do you prefer to be alone?

369. What is your ideal if you had to keep it a secret?

370. What was your first impression of us when we first met?

371. Do you still have feelings for your ex-boyfriend?

372. Would you still wait for me if I had to relocate for a number of 10 years?

373. What are your thoughts on long-distance relationships?

374. Can you tell me about your first boyfriend? How was your relationship with him?

375. What would you think if I went out with someone else?

376. Have you ever regretted having sex with someone?

377. Have you ever kissed a female who reminds you of yourself?

378. Do you feel vulnerable by dumb talk? And what is the reason?

379. Can you tell me about your first one-night stand?

380. Do you enjoy going out with me on a regular basis?

381. How would you react if your best friend informed you that she had caught you with another woman?

382. Have you ever felt like you’re being watched?

383. Would you sex your ex if you had the chance?

384. How would you react if I had a much more significant intimate relationship with you in the past?

385. Do you believe you can fall in love at first sight?

386. What is the dirtiest thought you’ve ever had about someone you’ve never met before?

387. Do you ever dream about having sex while you’re sleeping?

388. If you had the chance, how would you sexually dominate your boss?

389. What’s the creepiest sexual fantasy you’ve ever had?

390. What’s the dirtiest thing you’ve ever heard someone say while having sex?

391. Have you ever had sex with someone who is married?

392. What’s the filthy thing somebody has ever said about your nude body to you?

393. Have you ever fantasized about having a sexual relationship with your crush?

394. When was the last time you had an orgasmic dream?

395. Can you tell me about the dirtiest massage you’ve ever given or received?

396. Have you ever had a romantic relationship with a coworker?

397. Do you want to have sex in a group? And what is the reason?

398. If you could sleep with any celebrity, who would it be and why?

399. Do you enjoy employing props in your bedroom?

400. What is your most important roleplay? And what is the reason?

401. Who is your favorite celebrity in the live in a world of pornography?

402. Which of your sexual fantasies is your favorite?

403. Have you ever done your business in a public restroom?

404. What was the strange idea that came to you as you were touching yourself?

405. What is the best prop you’ve ever utilized to get yourself out of a sticky situation?

Good freaky questions to ask a girl

Everyone wants good things in their life, so why not have good questions. This also helps to establish your bond and make your feelings more close and intimate to each other.

So, let’s delve deep into the section of good flirty questions to ask a girl

406. Which of your sexual fantasies is your favorite?

407. Have you ever done your business in a public restroom?

408. What was the strange idea that came to you as you were touching yourself?

409. What is the best prop you’ve ever utilized to get yourself out of a sticky situation?

410. What was the oddest place you’ve ever had sex?

411. Which of my friends would you like to have sex with if you had the chance?

412. Have you ever had sex with a woman whose name you don’t recognize?

413. Have you ever kissed someone who looks like you?

414. What would you choose for me to wear right now if you had to?

415. What is the best thing about a woman that sexually draws you?

416. Will you marry me if I accidentally get pregnant for you?

417. How do you feel about my parents, siblings, and mother?

418. What will you do if I advise you to unplug from your social media accounts?

419. Which of my friends did you find the most attractive?

420. Would you still love me if I were paralyzed in an accident?

421. Would you forgive me if I regretted having sex with another man?

422. What if you wake up one morning and find out I’ve only got three days left?

423. Have you ever had sex with a complete stranger simply to satisfy his or her desire?

424. Have you ever been caught cheating on a date? What is the reason for this?

425. Is there anything you don’t want to do while you’re lying in bed?

426. What was the most treasured sex experience you’ve ever had?

427. What has been your most pleasurable sex experience with me?

428. Who was your ex-boyfriend or girlfriend, and how did your relationship with the end?

429. Have you ever been forced to engage in sexual activity?

430. If I’m out of town, would you sleep with another girl?

431. Would you fall for a girl if she seduced you?

432. Do you have any expectations while lying in bed?

433. How would you react if you were asked to have sex with your boss?

434. What would you say if you came across me and your best friend in a hotel room?

435. Will you still marry me if you find out I had sex with your best friend?

436. How would you react if I told you that I had sex with your sister the night before?

437. Have you ever suddenly left a job? Have you had a lot of job changes?

438. Is your job a career or just a job for you?

439. Has your job ever contributed to the end of a relationship?

440. Where would you live if you could live anywhere in the world?

441. Would you rather live in an urban, suburban, or rural setting?

442. What would you say I’m like in bed, in your opinion?

443. Has your penis ever reached the end of your vaginal opening?

444. What types of pornographic videos do you enjoy watching? How often do you watch porn videos?

445. Have you ever had sex while closing your eyes?

446. Would you like me to touch which area of your body?

447. What is your all-time favorite sex experience?

448. What sex position would you like to see us try today?

449. When you’re having sex, do you always make a lot of noise or do you keep it quiet?

450. Do you want to kiss when you’re having sex?

451. When you’re staring at a girl with a penis erection, how do you put yourself together?

452. When you fall in true love with someone, how quickly do you usually fall in love with them?

453. Do you want a certain type of woman in your life?

454. How do you know who the most beautiful woman is? What distinguishes her?

455. How can you tell whether a lady is ready to have sex?

456. Have you ever considered having a sexual relationship with one of your teachers?

Random freaky questions to ask your girlfriend

Do you have some random flirty questions, then here you go. Random questions not only make your bond intimate but it also brings humor into your relationship. This combination works wonders. Then what are you waiting for?

Let’s dig deeper into the ultimate list of random cheesy pickup lines questions to ask your loved one. 

457. Have you ever imagined how it would feel if we kissed?

458. How do you react to my hug? Did you get dressed up for me?

459. When did you first notice that I was different?

460. When do you believe it’s appropriate for two people to become intimate?

461. What do you think the finest part of kissing is?

462. When do you believe it is appropriate to “make a move”?

463. When I’m not around, do you think about me?

464. Have you ever attempted to imagine me in my edible underwear? Which color underwear do you like?

465. Which of your dreams has been the most exotic?

466. What’s the strangest dream you’ve ever had about me?

467. What was your initial reaction to me?

468. How do you feel about me in three words?

469. What would you call me if you had to give me a nickname?

470. Have you ever had a fling with someone just to satisfy your lust?

471. What is the dirtiest thought you’ve ever had about me?

472. Where would we go if we could go anywhere right now?

473. What would you wear if you could see me in any dress right now?

474. How do you feel about a guy’s body hair?

475. What would you wear if you had the option to choose what I was wearing right now?

476. What part of your body do you prefer to be touched often?

477. When was the last time you experienced a dream that was filthy?

478. Where would you have sex if you could have it anyplace in the world?

479. Have you ever had an affair with a coworker?

480. What would you do if I said I wanted to have sex right now when we were out to dinner?

481. Where have you ever masturbated in the strangest place? How did you learn to masturbate? 

482. What was the most humiliating sexual experience you’ve ever had?

483. Have you ever had sexual fantasies about someone else?

484. Would you stop or continue if I ever caught you masturbating?

485. Do you like to be in command or to be obedient?

486. Do you prefer one-night stands or sexual partners for a longer period of time?

487. Do you prefer to be at the top or the bottom of the heap?

488. What are some things you’d like to do more of in bed?

489. What time of day do you prefer to have sex?

490. When we’re together, what’s your favorite part?

491. Could you give me some examples of why I like you?

492. What do you want out of a relationship the most?

493. Do you think you’d react if I kissed you right now?

494. In a relationship, who should make the first move?

495. Where would you like to go on a date if I could take you anywhere?

496. On the first date, do you invite someone in?

497. Do you believe that lovemaking can take place anyplace, not just in a bed?

498. Do you have any moves you’ve never attempted but have always wanted to?

499. Do you enjoy experimenting in bed with extreme temperatures such as ice or wax?

500. What kind of bedroom props do you like to use?

501. What is the most daring place you have visited?

502. What are three areas outside of your house where you’d do it?

503. Which sexiest outfit would you like to see me in?

504. Would you prefer to ride in the front or the back of a motorcycle?

505. Would you agree to develop a bedroom bucket list for me to check off?

506. Would you accompany me into a fitting room if we were shopping for clothes?

The wrapping up

Asking your girlfriend questions is a great approach to get to know her better, strengthen your relationship, and discuss topics like sexuality.

Some of the dirtiest questions to ask a female are listed above, and you may even SMS them to her. These appealing inquiries will keep your relationship going strong.

Finally, try to ease into it, don’t ask these questions out of the blue before you’ve had a chance to get to know one another. Feel free and have fun asking!