Cuckold Challenge

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Cuckold Challenge
Home - Cuckold Guides - The Ultimate Hotwife Dares/Challenges
Jack and I have made something very special for you. We figured it would be a great idea to make the ultimate list of challenges for budding hotwives and their cucks. We wanted to create a list that would include everyone, no matter how submerged into the lifestyle you are. The aim of this list is to allow you to grow, open up your relationship and sex life in new ways, and really discover new kinks and turns on for the both of you.
The great thing about this challenge is that even if you have done some of these things before it allows you to explore from the beginning, opening you up to forgotten experiences and making new memories for you. We made this challenge and yet we have found fun in going back to the easy challenges that we had forgotten about and originally brushed past, so no matter where you are in your hotwife journey, there’s something in this challenge to please everyone and make new sexy memories for us all.
There are three ways you can play our challenge, which one you choose is up to you. Think about it before you make an instant decision because this list will change the way you and your partner operates if you choose to partake.
This is your first option, the challenges start off quite easy and get harder as they go along. With this first challenge, you have 30 days to complete as many of the tasks on this list as you possibly can. This could mean you are throwing away your inhibitions and going all out for one month or it could mean you are choosing carefully but deciding to do these carefully chosen tasks every single day without a break.
The second way you can complete this hotwife challenge is to pick 15 (or write down every single challenge you like) and write the dares on a piece of paper, tear them into little squares, mix them up and randomly pick one from the box whenever you feel like it and whichever you choose at random, you have to do. This raffle makes the challenge last a lot longer but it’s great to spice up the bedroom and for something to look forward too.
This challenge works the same as the first except you have 7 full days to complete as many of the challenges as possible. You can pick and choose the tasks you wish to do before you start but you must remember you are on a time limit of 7 days, no more and no less. Doing this option allows you to come back and do 7 more whenever you feel like it.
Once you have completed the hotwife challenge, no matter which option you choose, make sure to leave your results down below along with your findings and how it went for you or simply send a message in. We are so intrigued and excited about this challenge, we hope you have the best fun. Also, if there is a task you have already tried that is on our challenge be sure to let us know that in the comments down below too, we want to see how many of you are as kinky as you make out!
Warning: Do these challenges/dares at your own risk.
This is just a bit of fun, please only do the challenges you are comfortable with and do them at your own risk.
We decided to pull out something new from our homemade raffle whenever we were feeling frisky and just try it out, whether we had done it or not and let me tell you, it was so much fun and we have had so much great sex that we have just kept our raffle going and we try something new from the list and then put it back into the bucket so that we may be able to do it again.
We choose from our raffle bucket so often that we get so excited to do it, it has brought us so much satisfaction and fun.
At the very end of this article, I have included a printable checklist with every challenge on it for you to tick off, that way you can have every challenge all in one place ready for you.
Here we go! These are the hotwife challenges and dares for all of you kinky couples embarking on this adventure. We wish you luck, lots of fun, and an extremely rewarding ride! We can’t wait to see your results of how many you did and what you found from this challenge in the comments below (or send them in!), let’s go!
You are going to need : Yourself, your partner, some time and maybe some paper depending on which of the three options you choose from above. That’s it, now go have fun some fun!
#1 – Go out in public a short skirt with no underwear
This challenge is pretty easy, not wearing any underwear with a short skirt as you venture into the outside world. Can you do it?
#2 – Accidentally Flash Your Boobs To A Stranger or Male Acquaintance
This could be at the beach, in a changing room, your shirt becoming unbuttoned, as you answer the door in a towel, etc. Get creative and get flashing.
#3 – Take your panties off in public
Wear a skirt to make this easier but whip them off in public. This could be in your car, a parking lot, a public bathroom, etc. Just get them off and leave them off.
#4 – Do an old.mojoupgrade.com or BDSMTest.org sex test (see what kinks you have in common)
old.mojoupgrade.com or bdsmtest.org are both great tools if you are both unsure about your kinks and desires in the bedroom, it will allow to see if you’re both on the same page and it will open up new avenues for your sex life.
So, both take the tests above and compair your results and see if you’re a match and if you unlock any new fantasies you’d both like to try.
#5 – When you go out smile at every guy you think is hot, see where it takes you.
This can be with your partner or not, but make it obvious. Make him jealous if that’s how you both work and enjoy the flirtation.
#6 – Find a hotwife video/story that turns you on and show your partner
It doesn’t how they’re going to react, you need to show them a story or video that really gets you wet between the legs and show it to them.
#7 – Make yourself cum while thinking of another guy
Bonus if you tell your partner who you are thinking of when you are getting off.
#8 – Forget to wear your bra in a lose fitting top
Some of you may already do this but it’s definitely a challenge for some of us. Be confident and go out there with your nipples and breats out and proud.
#9 – Expose Your Tits in a large shop
Wether you turn to flash your partner or you have an outfit ‘fail’, it’s up to you but get it done to cross it off.
#10 – Time how quick your hubby cums when you talk about :
This task takes a little longer than some of the others but it’s fun. You can practice your dirty talk and your erotic story-telling skills, just don’t forget the timer. Write down your results too, we would love to see how long he lasted, you may both even find a new kink!
#11 – Give A Handjob while you describe sex with an ex partner
Tricky for some if you have not yet explored cuckolding/hotwifing to a its full extend but lots of fun and let’s just all agree that it’s very kinky.
#12 – Talk to one of his friends/acquaintances/random male or family members on the phone whilst you ride a dildo (or use a vibrator)
The key is not to moan, not to make a noise, and continue the conversation as normal. Make your partner watch, put on a show. This is way more difficult than it seems.
#13 – Show your husband sexy pictures you’ve sent ex partners
If you haven’t got any that you have sent to an ex, make some and then show them to your husband, make them dirty, and way worse than what you would send to him.
#14 – Have Your hubby wear your panties as your jerk him off
Pick the most feminine pair you have and make him wear them and then soak them with his cum.
#15 – Show your hubby how you would suck his dick if we was hung
Emphasize how it would be if he had a bigger penis, show him your best moves, blow his mind and act in despair that he just doesn’t have the dick for it.
#16 – Make your husband watch you masturbate and cum and not allow him to touch himself
Make him sit and watch like a good cuck.
#17 – Show your hubby your big dick sucking skills on a dildo
Get a dildo and make your husband watch as you blow it, go down it, be enthusiastic, try out any move you have ever seen, even let out little moans.
#18 – Point out men you would like to sleep with
Head to a park or a restaurant and pick out men you find attractive and ones you would be happy to sleep with. Make your hubby see your taste and make him feel like a bit of a cuck.
#19 – Simulate a threesome using a suction cup dildo/sex machine and your hubby
Incorporate a sex machine or a suction cup dildo into your bedroom life and simulate having a threesome with your husband. The idea is that you have one in your mouth and one in your pussy. It’s kinky and it is a lot of fun. It’s also great if a real threesome is something you are intrigued about.
Same idea as the task above, but this time you use a butt plug/ double ended dildo to simulate a foursome as well as your hubby, a dildo or a sex-machine.
#21 – Accidently show someone you find hot a nude while showing them something on your phone
This is done pretty easily, just go to show them a picture of something they might enjoy such as scenery, your pet, an event, etc and swipe the wrong way, revealing a nude picture to them. Preferably do this infront of your husband.
#22 – Slut Training Challenge (Hard)
You are not allowed to cum until you work your way up to a 10– inch dildo, you must also stretch out your butt using different sized butt plugs to get ready for anal sex, Buy some slutty crotchless panties, Find a cute revealing summer dress, stop wearing your bra in public, Learn to swallow cum and Get a hotwife anklet. Once you have done all of this you have completed the slut training task.
#23 – Play naughty truth and dare with a group of friends (let your inner slut out)
This must be with a group of friends that you trust. Ask intimate questions, reveal sexual secrets and let your honest flow out of you.
There are so many around, you just need to perform a quick search and see what comes up. If you aren’t comfortable with a sex club in your area wait until you next go on vacation and try one out in a different city to your own.
#25 – See how many guys you can flirt with in the sex club
You don’t need to sleep with anyone but flirting didn’t hurt anyone, work your way around the club and flirt with as many as possible. Bonus if they are hotter than your husband.
#26 – Have your hubby make his dick big with a penis extender and roleplay that he is a bull
Make your husband wear a penis extender and get off on how much bigger he feels, roleplay him being your bull, tell him how much better he is compared to your ‘husband’ and really roleplay your way into this one.
#27 – Tell your husband which of his friends you find attractive
Go through his friends and decide which ones you would be with, which you would fuck, which you would make out with, and so on and so forth. It’s a lot of fun and may reveal a lot about those fantasies you had locked up.
#28 – Show your partner any pictures you have of your exs cocks (If he is smaller than them, let him know)
If you don’t have any improvise and find some online that look very similar.
#29 – Go to a club and dance with another man while your husband watches
Have some fun, let your hair loose and dance all whilst your husband stands back and observes.
#30 – Find your ideal cock size by using some dildos
Buy a few, try them out and distinguish which size is your favorite and be sure to do it all infront of your husband.
#31 – Wear a wireless vibrator in public
These are easy to get ahold of just pass the remote to your husband and have him control your pleasure levels.
#32 – Go to a nudist beach and spend the day naked
If you don’t want to go to one local to you wait until you are next heading on vacation and scout one out in the area. For bonus points use the remote control vibrator on the beach.
#33 – Only let your hubby cum at the thought of you with another man
Whether it’s you jerking him off and giving him dirty talk about another man or talking about a cuckolding fantasy, only let him cum when he has heard enough.
#34 – Go on Adult Friend Finder and find someone to have cam sex with (while your hubby watches)
This is sometimes the first step a lot of hotwives and cucks take and whether you’ve done it before or not, having cam sex with someone new is always exciting and there’s this whole guide here on how to have safe cam sex .
#35 – Don’t let your hubby cum till he gives you full permission to be shared
Tease him, bring him to orgasm again and again until he fully submits to you and you wishes.
#36 – On a girls night out send your husband pictures of you flirting and having fun with other men
Drive him wild with your flirtatious nature, tell him about all of the fun and fabulous things you are getting up too.
Order room service or get a takeout to your hotel room and open the door doing any of these things:
#38 – Reinstall Tinder on your phone and let your hubby have control of it
Let him pick a man for you, let him talk to someone on your behalf and set you up with someone.
#39 – Have a dirty text conversation with a stranger (use Tinder or adult friend finder)
Either with the person, he has selected or someone you have chosen, have a conversation get sexual with this stranger, once you’re done, show your husband.
#40 – Get a guy to send you a dick pic
This can be with the person your husband found on Tinder or with someone you found, once you have the dick pic, the task is complete.
#41 – ‘Sext’ a guy, make him cum with your words (ask for proof)
Again, this can be the same Tinder guy or another one. Engage in some sexting, enjoy it and maybe you could even cum too?
#42 – Suck another guys cock infront of your significant other
How you do this is between you two but it’s on the hotwife challenege for a reason, no matter how deep you are into this lifestyle.
#43 – Learn to deep throat your bulls cock
Deepthroating takes some skill and so learn how to do it but not on your hubby, on your bull.
#44 – Have a guy you like clone his cock using ‘clone a willy’ (use it in front of your husband)
This can be a big ask but it’s very frustrating for your husband to see you getting off on another guy’s cock when he is right there.
#45 – Wear your sluttiest clothes when his friends are over
This could be your shortest skirt, a low-cut top, no panties, or even just a towel.
#46 – Tell your husband about the men in your life (work, friends) that you would love to fuck
Tell him everything, all about them and their lives, and how you would fuck them.
Be sure you trust this man but once you have selecred the right man, send him a naked pictire of yourself and let your husband know of course.
#48 – Have a professional photographer take nude pictures of yourself and show your hubby after
There are plenty of photographers out there who are willing to do this.
#49 – Have your husband show a sexy/nude picture of you to one or more of his friends (ask them for their feedback)
He has to trust his friends to be able to do this and if it’s something he isn’t sure if he could do, have him show them something else on his phone and then accidentally swipe to a picture of you.
#50 – Use a vibrator while watching big dick porn while your husband masturbates in the corner of the room
Make him feel like a little cuckold.
#51 – Wear a remote control vibrator to a bar/club
This is lots of fun and it’s up to you if you or your husband controls the vibrations or you could even have your partner watch you from a distance and control it.
#52 – Share a faceless sexy selfie for people to rate online
There’s lots of places you can do this and it’s thrilling to have other people rate your naked body. We even have a place on this blog where you can rate a wife and we also have it in our membership, for people who want more privacy, but still want the thrill.
You can also go to any of these Reddits to share your nudes for feedback:
#53 – Go on a solo date (tinder is a good place to start)
Make some rules and then go on a date whilst your husband stays at home.
Tinder is probably the best place to find a date, but here’s some other amazing hotwife dating sites that we use.
#54 – Wear a micro bikini to the beach/pool
If micro bikinis are not your thing find the smallest bikini you can that leaves very little to the imagination.
Have a kiss with your date, tongues, just lips, whatever you feel most comfortable with.
#56 – Touch a guys dick through his pants
Preferably the guy you decide to go on a date with, feel his crotch and tell your hubby all about it.
In the back of his car? Back at his place? In a nightclub?
#58 – Have a date give you a hickey
Make sure it’s somewhere your husband will see, this could be your neck, breast, stomach or even thigh.
#59 – After a date give have your hubby fuck you slowly while you tell him all about it
Go into detail about how thrilling it was, what a great guy he is and how hot he is too.
#60 – Give someone who is not your hubby a blowjob
#61 – Have your hubby be your sloppy seconds
Either blowjob sloppy seconds or more extremely sex sloppy seconds.
This guide explains everything about having fun with sex leftovers .
#62 – Have your hubbys and your boytoy cum on your body at the same time
This could be your hubby and your bull, your hubby and your new date, whoeever it is, ensure they time their orgasm so that you are covered in both of their cum.
#63 – Swap nudes with another couple
Find a couple you like and trust and swap your nudes with them.
That’s it! Wear a blindfold and be fucked. A nice twist is to have your hubby blindfold you and arrange a guy to meet you at your hotel room and fuck you without having you say a word, just like what happened in this story .
#65 – Leave your husband on the phone line while you get fucked
You could leave on facetime so that he can watch or just don’t hang up when you speak to him so that he can hear you banging.
#66 – Have your hubby practice cleaning up cum
Have him cum on/in you and clean you up.
#67 – Have another man cum on/in you and have your hubby on clean up duties
Practice makes perfect and once he is used to his own cum, somebody else’s will be a walk in the park.
You can gain some more ideas, by reading this story from one of our friends about her husband’s clean up duties .
#68 – Take a selfie with another guys cock that isn’t your husbands
Even better if the guy is hard and bigger than your husband.
#69 – Fuck someone 10 years older than you
Find some who is 10 years older than you and fuck them.
#70 – Go on a date with a remote control vibrator or a butt plug inside you
Control it yourself if its a vibrator and keep the butt plug in on the date. Text your husband all about it and even tell your date about if they know about it.
#71 – See if your Stag cums at the idea of cleaning up your bulls cock
Talk to your hubby about cleaning up your bulls cock as you jerk him off or fuck him, see how he reacts and try and make him cum as you talk about it.
#72 – Measure your cucks and your bulls cock
See the size difference and even if your hubby is bigger, make out that your bull is far superior down there.
#73 – Have your bull and hubby compare cocks in real life
Make them both hard and then have them compare their sizes together.
#74 – Come home with cum stained clothes
After a meeting with your bull or date go home with cum somewhere on your clothes. It could be on your lingerie, your shirt, jeans, or skirt, just somewhere noticeable.
#75 – Shove your cum stained item of clothing in your cucks mouth while you give him a blowjob/handjob/sex
Have your bull cum over an item of clothing and bring cum stained item to your hubby and have him clean it up while you give a blowjob, handjob or have sex.
#76 – Peg your hubby
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