Hotwife/girlfriend Challenges

Hotwife/girlfriend challenges.

I know a lot of hotwife dare/challenge things are out there, I just wanted to collect as many as I could come up with and put them all in one place. So, for your enjoyment, 101 of the dares I find exciting. These are challenges for the ladies who are in a committed relationship.

It shouldn't need to be said, but this is "HOTWIFE" related, meaning slut wives, cuckolding. If you are reading this AFTER reading the title, you have no reason to be shocked when you find out there's cuckolding in it. But, you guys do what you do, spam "1" bomb the story, wait, READ the story first, jack off, THEN spam bomb the story and bookmark it so you can read the next one, too.

By the way, this is NOT a how-to manual, most human beings won't ever go past the beginner stage, and that's fine, whatever works for you. I grouped them by "Beginner, Intermediate, Advance, and Extreme" categories. I've been in the lifestyle, my wife has actually done things from all of the categories. Things ARE possible, but it takes a lot of trust and daring for both parties to withstand the consequences of doing such things.

The way I'd rate them is, Beginner would be things your girlfriend/wife might try, after discussing and fantasizing about the thought of the hotwife fantasy for awhile. They don't require nudity, sex with others, or a whole lot of risk. It's kind of a "feet wet" idea, that trying them might get you going to more daring challenges, or, you may decide that these are plenty for your liking. There can be some embarrassment to them, still.

The Intermediate category includes doing some embarrassing things, some nudity, definitely more daring. These are things that people who have progressed from the beginning stage and don't find them as thrilling anymore. I'd actually say most people who fantasize about the "hotwife" lifestyle and are adventurous, fit into this category. There is still no sex with others...though many of them could and would certainly lead to it.

The Advanced category includes sex with others. The categories are also naturally progressive and there are some repeat ideas, only with more daring elements at each stage. There are swingers and lifestylers who probably can look at this category and say, "been there, done that," but I'd say it's probably far beyond what most fantasizers even WANT to do.

The extreme category is just that, everything above but with the highest risk of embarrassment, humiliation if it goes wrong (even when it goes right, sometimes.)

Beginner-

1) Tell a very trusted girlfriend that you and your man are fantasizing about doing your hotwife fantasy.

2) Pay attention to the amount of interest you get from men. Sort them by category. A- Those that didn't change the way they looked at you, B- Those that enjoyed looking but wouldn't approach you about it and C- Those that would definitely be interested in seeing more of you. Tell your guy what those in "C" might like to do to you.

3) Wear the sexiest panties you have at the store or at work and when you see a man looking at you imagine what he'd think if he knew what you were wearing underneath.

4) Have a sexy picture of you either showing a lot of cleavage, like in cute shorts and a crop top, or in a bathing suit, as your phone screensaver. Purposely leave it lying around when guys who flirt are around.

5) When out with your girlfriends, let a guy or guys give you their numbers. (As kind of a double, this could be the opportunity for the above picture to "accidentally" show up when you are entering their numbers.

6) Start dressing more sexy, especially at work, enough so that people you are close to notice.

7) On a highway drive, wear a sheer top with no bra, let cars that pass see you.

8) Admit to your closest friends that you are horny all the time and that you "aren't sure that my boyfriend can handle it alone."

9) Have a photographer take sexy pictures of you, say they are for your man. Pose however he wants you to, in your lingerie, bathing suit etc.

10) Pick out one of my friends and make him "your favorite" tell him heartfelt things, including risque ones.

11) Have your man drop you off at work so that you need to ask a coworker to drive you home, one that has been flirty with you.

12) Flirt with every single food deliverer, repairman, handyman etc that comes to your house, not changing from your PJ's, or nightshirt etc when they are there.

13) Do your gardening/yard work with just your cut off jean shorts and a bikini top. Work on the areas of the yard where you know the neighbors can get the best views of you.

14) Go to a bar, or be at a party and give a guy your number, even though they know you are "with" someone. (For the beginner stage, have a "burner" phone or one just for this purpose),

15) Go to a drive through fast food place with a very loose top which will allow them to look directly down at your tits. Be forward enough so they can see completely down the top.

16) When we see guys, or are among guys like your man's friends, coworkers, start telling him what you like, or don't like about them attraction-wise, then tell him what you can imagine doing to, or with, them.

17) At the beginning of the week, flirt back with someone at work who has been a constant flirt to you. By the end of the week have him thinking "it" is possible.

18) Take walks around our block wearing your form fitting yoga pants and your sports bra top.

19) Go to work one day without underwear. Wear a dress or skirt tight enough where it is obvious there are no panty lines, if anyone cares to notice.

20) Text (or sext) one of your internet only buddies while you and your bf are having sex.

21) Start pinching your nipples just before you know a guy will see to make sure they are hard for him to see them through your blouse or sweater.

22) Get a part time job as a waitress at a place known for leering or groping men.

23) (Related to above). If at your current work, or at your new part time job, if guys grope you, you say no, but don't physically take their hands away.

Intermediate (Daring)

24) Get your nipples pierced and send pictures of it to friends before you send it to me. *(Bonus)- include one, "accidentally" to a male friend of you or your significant other.

25) Make a list of your hotwife fantasies and have it in a USB or document file on the computer that we let our friends use when they stay over. *(Bonus)- keep it on a file at work but keep your password somewhere close, like taped to the side of the pc.

26) Get your tits out when you are in a hot tub, even among friends. Be the first woman at the party to always have her tits out, like flashing, at least.

27) (related to the last one) When you two have friends over for things like sports watching or poker (could be generally an all male affair) the talk usually gets raunchy, like commenting on famous singer's or actresses tits or the like. Act offended and pridefully boast you think your tits are better than, say, Amanda Seyfried's. Then, show them all to prove it. *(Bonus)- If they are smart guys and catch on and start talking about women's asses, show them your ass as well to "prove your point."

28) Tell a friend who is known to gossip about your hotwife fantasy. Stress how hot it makes you. Tell her things like how much you love sucking cocks (see if she notices the plural).

29) (From above) Have a coworker drive you home. Flash your tits to the guy that you pick to drive you home, promise him he can see your tits any time he drives you home.

30) Make sure every one of the handymen, delivery guys etc get to know what your tits look like during your flirting, lots of cleavage, looks down blouse, etc. Every one of them needs to know your tits completely and could pick them out of a lineup.

31) Have a racy photo of you on your phone like you in sexy lingerie or something like you, topless, holding your arms over your tits, and/or wearing a collar. Again, "accidentally" leave your photo gallery open to it, either at work, or when we have friends over.

32) Flirt with his friends, his boss/ coworkers at parties, get-togethers. Let them start thinking that you might be "that" kind of girl. Purposely dress sexy as well, tight shorts, revealing tops. Make it easy for them to imagine it.

33) Never turn down a guy's number when he offers. Then, once a week, block your caller ID and randomly pick a number and send a topless picture of you, asking, "remember me?"

34) Wear your slutty "going out" clothes and go to a local bar often enough so that the bartender you picked out has seen pretty much all of your tits other than your nipples...or even your nipples.

35) Pick out one of his friends and zero in on him (from earlier). Let him be the one you flirt with the most. Be the freest around him, like you are comfortable with him seeing you walk around in your underwear. Reveal the most to him, like what you like sexually. Show him the pictures of you in various states of undress. Make your man invite him over frequently, most often by himself.

36) Say the mailman likes to cut across the yard to deliver taking him in front of the picture window every day. Be topless, or bottomless, or both, every day. See if he starts noticing.

37) Tell your friends everything you are doing, it'll get back to their husbands and boyfriends, I'm sure.

38) Pick out an old guy, he has to at least be the age of your father. He could be the librarian, or your doctor, or boss, coworker. He should be single, and not have had sex for awhile. But, give him extra visual access to your body. Purposely dress provocatively when you know you are going to see him. Bend over, suck on your pen tip "subconsciously."

39) Around someone you know is interested, like a coworker or your boss, fake a phone conversation that you know they can overhear. Make it clear that you are extra horny and that you haven't sucked or fucked a big cock in "SO" long. See if you get treated differently after that.

40) Always answer the door to food delivery with "too much" cleavage showing or glimpses of you ass in panties under a long shirt, things like that.

41) make your man keep a detailed diary of everything you do, including the advanced ones. Make sure he writes it all down, then keep the diary yourself and threaten to show it people who you know it would be embarrassing for me if he gets out of line.

42) On the highway, while your man drives, take off your top and keep your hands behind your seat. Have him purposely drive slowly past trucks and let them see your tits. *(Extra bonus)- Have him raise your skirt slowly, revealing more and more to each truck driver until your skirt is over your hips, your pussy and tits are out.

43) Have a photo shoot of sexy lingerie pictures, do what the photographer wants, including revealing more, even if it means stripping naked and allowing him to take every picture he wants.

44) Set up an internet account, tinder, reddit etc and do live shows with you topless, or in underwear. Have it be "dare" themed, like these challenges. Pick one every day and do it "live."

45) Sunbathe in the backyard topless. Position yourself so that, even if it looks like you are trying to stay out of sight that there's a spot in the neighbor's yard or a window where you know they can fully see you. *Bonus- after tanning that way for awhile, roll down your bottoms to sun your ass, Stay that way for at least 15 minutes. (hopefully they have their cameras out by this point).

46) Let a friend, coworker, or someone new grope you (Either your tits or your ass) at a party when you two are out together. Allow it for a few seconds before playfully batting their hand away. *Bonus, tell your husband/bf about it, then if they try it again later, let them, for longer, like thirty seconds.

47) For the time being, every time your man cums in you, call him a name of someone you know who excites you. Make it a different name each time he cums. And, depending on where he cums, like if it's your mouth, make it the name of a guy who you'd like to cum there.

48) Get a temporary tattoo of a black spade (representing black cock slut) and put it on the inside of your cleavage, enough to peek out under whatever you are wearing. Then, go to a bar you know is frequented by black guys and if someone asks to see the whole tattoo, you show them.

49) Go to a real tattoo shop and find a male artist for a "consult." Ask him about you getting a "Slut" tattoo, either the word or some representation of it. Tell him you wanted "Cock slut," but ask his opinion, what is available. Then, discuss where would be best to get the tatt, like, under your bathing suit line. Then, tell him you'll consider his ideas and then leave.

50) At a party or large get together, brag about your love of sucking cock loud enough so not just the girlfriends you are sharing it with can hear.

51) Buy a Hotwife ankle bracelet and always wear it.

Advanced (when you are ready for sex with others, but hold on tight, it's going to get adventurous if you do. There are many that actually are "extreme," there's kind of a gray area between categories!

52) (From above) If you did have your nipples pierced, let one of your lovers fuck you first and get to suck on them before your man does.

53) (From above). Make a list of your hotwife desires on a USB then "lose" it somewhere like at a party at your house (or at close friends), or at work or even in public somewhere. It doesn't have to have incriminating personal information on it, but leave enough clues that if someone you know or work with knows you well enough, would figure out it is you.

54) (From above) Joke with the coworker that drives you home by asking, "Cash, Ass, or grass?" then sheepishly admit you don't have any cash or grass, then pay up accordingly.

55) Have one of your lovers work over your tits with love bites, hickeys, pinch marks and let him cum on your stomach and tits so that your bf will have to see them when he's fucking you later. *Bonus- let him spank the shit out of your ass until you cry, then show it to your guy when you walk in the door.

56) Make sure the handymen/delivery guys that come to the house know that their bill can be "negotiable." See how many discounts you can get by using your mouth or pussy...or even ass, to lessen your bills. Your man should be expect to be getting free food from some of those places. *(Bonus)- Develop a "Pay scale" for some of them.

57) Have sex with someone that you know your guy would be totally surprised by for at least a month without telling him who it is. Tell him everything you two are doing, just not who it is, until you've done it repeatedly for at least 30 days.

58) Tie your guy to a chair and either bring one of your lovers home to fuck you on the floor right in front of him, or do it with one of the delivery guys.

59) Tell one of your girlfriends, the one who is the closest to your circle of guy friends, about the things you are doing with other guys. Then, pay attention to the guys she knows, see if they treat you differently than before.

60) Send an anonymous topless picture to one of the men's numbers you have, but if he responds wanting more, sext him and see if you can get him to cum, even if it means sending him another picture of your bare ass.

61) See how big a tab you can run up at the local bar over time before the bartender asks to collect, then see if you two can "work something out" in the back parking lot Then, depending on the size of the tab, give him his money's worth.

62) Pick out one of your big projects, like moving heavy furniture and pick one of your neighbors to help, then reward him with your mouth or with a shower with you to "clean up."

63) With all the guys numbers you have, make a game out of it. Once a week text 3 random numbers and ask, "what would be the sexiest place to get your cock sucked?" The one with the best answer meets you at that place and gets his cock sucked.

64) Hopefully, from all of the other suggestions, you'll have guys at attention, so it might make it easier, but, pick out one of your husband's friends and have a torrid sexual affair, fucking and sucking all over your house. It could be weeks, even a few months. Make him not be able to walk through the house without knowing that the other guy took you there, or there. On the carpet, in his favorite chair, over the kitchen table, on the balcony, on the washing machine. Make sure he knows of every single place he got his cock in you so thathe has to picture that daily, as he walks through the house. (Extra bonus*) Let your bf hide for some of those times and make him watch the guy ball you to his heart's content.

65) (From earlier) Flirt and blue ball an older guy for awhile, then, find a reason to have to go over to his house for something, say he mentioned a book you should read that you could borrow. Then, show up at his house in your long coat and only your black lingerie set underneath. Let him take his time with you, coax at least one orgasm out of him, leave him smiling.

66) Speaking of the needy, find out from "his" friends who has gone the longest without sex. That will be embarrassing enough, asking them about that, but when you've found "the one" tell him to leave Friday night open and that he can have you in any way he chooses until morning.

67) (From above) Have the fake conversation about how you miss sucking and fucking big cock. The coworker or boss that overheard your conversation, if they approach you afterwards (doesn't have to be immediately) and hint at wanting to "help" you with your problem, let them. Ask them to show you and if it ends with them fucking you on your desk, so be it. * (Extra bonus) If it's your boss and he hints that he has just the dick for you ask him to prove it. If he takes it out right there, then drop to your knees and suck him just like that.

68) Another oral challenge. Of all the friends, coworkers and random guys numbers you have, see how many different cocks you can suck in a week, a month, all summer (or whatever season). A an added bonus, see how many cocks you can suck in one day. They all have to be different, and they all have to be separate encounters, no blow bangs. *( Bonus)- Kisses for your husband/bf after each one, or at least a picture of the "evidence."

69) Pick out a food delivery place and driver. Make it one who you can ask for by name. After the preliminaries of teasing him the first time, every time after you greet him naked and take care of his cock either with your mouth or your pussy, bent over our couch. Leave the blinds open in the entry hall, so nosy neighbors might catch you doing it. * (Extra bonus) If you find someone who you really dig doing it with, ask him if he has a friend he can bring.

70) Text the ex who you had the best sex with, out of the blue. (If he is single and/or willing) and just say, "I miss your big cock" and add a sad face emoji, if he asks for it, whatever it is, you give it to him, even if it means getting right up and meeting him. (Extra bonus*) after wearing you out, you offer him "fuck buddy" privileges and if he asks about your bf, you just giggle and say, "he doesn't have to know, does he?"

71) Ask the techiest, nerdiest guy at work if he can help you with a "special" project. Explain to him you want a sex website of you, let him set it up. As payment, you let him video you giving him the fuck of his life. Then, you let him post it on your site, allowing him to block his face, but not yours. (Extra bonus)* Give the same deal to any of the other nerds that help after hearing from him.

72) Have sexy pictures taken. If the photographer suggests live sex pictures, allow him to fuck you in every position while he takes pictures of it. (extra bonus*), have the photographer be someone you and your guy know, like a friend or coworker that's into photography. If it progresses to sex, suggest the photographer make it a "video" session. (Extra extra bonus*) tell the photographer it's ok to share the pictures and video with his friends (especially dirty if it's someone you two know).