So you’ve recently discovered an attraction to cuckolding, and want some inspiration for turning your fantasy into reality.
Well my sweet chastity cuck, you’re in the right place.
Here you’ll find cuckold challenges and hotwife dares that will help you explore this fetish as a couple without needing a third (or fourth) person. We’ll help you gently progress towards the more familiar image of modern-day cuckolding: the chastity cuck sat in the corner of the room, looking on helplessly as his partner is lost in the throes of pleasure with a bull.
Feeling excited and ready to play? Glad to hear it. But first let’s make sure you know what you’re getting yourself into, and discuss how to keep cuckolding play fun and consensual.
Cuckolding: An Overview
‘Cuckold’ is the name given to the husband of an adulterous wife who’s unaware of her extra-marital antics. The bull is the other man, the one who’s diddling the hubby’s wife.
Or at least that’s what the term used to mean. These days it means something completely different.
Today, cuckolding is a fetish. It’s the act of consensually watching your partner lay with another. Because let’s face it: For us voyeurs, the cuckolding of yesteryear wouldn’t be any good. Where’s the fun in your lover having sex with someone else if we can’t watch (or at least hear about it)?
Modern cuckolding is:
- A consensual affair.
- Not always a husband offering his wife to another man.
- Playing with bulls of any gender.
But the cucking of today does have one thing in common with the cucking of yesteryear. It’s a fetish steeped in humiliation play, as Charlie Nyx explains in the guide to cuckolding and open relationships.
Today, cuckolding is considered a fetish. It’s the act of consensually watching your partner lay with another and getting off on it.
Keeping the Cuckolding Challenge Fun
I’d be an irresponsible Mistress if I didn’t highlight the emotional and physical safety considerations attached to many of these chastity cuck challenges. So here they are. (I’ve kept it as succinct as possible because I can sense you’re ready for play.)
- Talk about the fetish. This is the best way to be sure you and your partner are into the idea, and to establish any limits and boundaries.
- Make those limits and boundaries clear. Write them down if you need to. If there’s something you know you won’t be comfortable with (e.g. seeing your partner kiss someone else, hearing your partner wants to screw your best friend, etc)—then make that known before play begins.
- Also make them clear for anyone else involved. If you’re inviting other people to play, you need to get their consent and understand their boundaries as well–especially if they’re a one-night stand. You should also take the necessary safe sex precautions, such as STI tests for everyone involved beforehand (for peace of mind), and prophylactics during the session.
- Be considerate. If the challenge involves others who don’t know about your games, or they’re being done in public, consider how others may feel or react before going ahead with the challenge. These are supposed to be fun, safe, and consensual challenges. If you think someone may react badly or feel embarrassed, don’t do it. Save the challenge for a more appropriate time, place, and social situation. And always be aware of local laws.
- Have a safe word at the ready. You may not know how you feel about a fetish until you’re in the thick of it. So come up with a safe word before play begins, and agree that anyone involved can use it.
Now that we’ve covered the rules of engagement, let’s get into the fun stuff.
15 Hotwife and Cuckolding Challenges
I’ve put these challenges in order of ‘difficulty’. The list starts with fairly simple scenarios (for the newly initiated) and progresses to harder, deeper cuckolding play scenes. But you can start with any challenge and complete them in whatever order you like.
Explore them at your own pace. And remember: Enjoying this fantasy doesn’t necessarily mean inviting another person into the bedroom.
Challenge #1: The Hotties You’d Love to Handle
Hotwife, your mission is to compile a list of fantasy fucks (famous people and/or people you know IRL), and then text or email them to your chastity cuck. If you can, include images so your partner can imagine you with them.
Challenge #2: Exhibit Ohh
Encourage others to look on with admiration at your hotwife donning a skimpier-than-usual bikini to the beach, or a revealing outfit next time you go for lunch or dinner.
Enjoy the feeling of being an exhibitionist, hotwife? How about answering the door in nothing more than a robe or towel? Just be mindful of who’s at the door when you answer it. Your state of undress may not be a pleasant surprise to them. (Remember: They’re not a knowingly consensual party to your games.)
Challenge #3: Look but Don’t Touch
Hotwife, have your cuck sit and watch you get yourself off with your favorite sex toy. They’re not allowed to touch you as you play, and to make it even harder they’re not allowed to touch themselves. For Femdoms, this challenge is especially satisfying when your partner is locked in his male chastity cage.
Challenge #4: What’s Your Name Again?
Probe feelings of humiliation and inadequacy by refusing to get your cuck’s name right during sex. Depending on your pre-agreed boundaries, you may ‘accidentally’ call him by his mate’s name, or shout out the name of his boss as you climax. If naming people you know is too close to home, use some of the famous names on your list from the first challenge.
Challenge #5: I Spy Someone I’d Like to Shag
Let your partner know when you see someone you think is sexy. So what if you’re out on an intimate date? If you spy someone you’d like to be with, or you’d like to see your wife with, tell them. Explain why you find them hot so you each get a feel for what you find attractive in others.
Challenge #6: Share a Cuckolding Bedtime Story
Write out your ultimate cuckolding fantasy, and read it to your partner at bedtime. If you’re not a writer, or you’re stuck for inspiration, you might enjoy retelling one of the many cuckolding stories by Girl On The Net.
Challenge #7: Simulate a Threesome or Moresome
Stock up on realistic sex toys—dildos, masturbators, oral sex simulators, even a sex doll—and use them as your bull (or bulls). Having extra toys to play with lets you explore different positions and sensations, such as double penetration.
If your chastity cuck is male, they may feel more comfortable exploring any bisexual tendencies they’re feeling with a realistic dildo or anal-shaped masturbator rather than diving straight into bed with another guy.
Chastity femdom tip: This challenge lends itself perfectly to ruined orgasm play, should you feel your cuck doesn’t deserve a satisfying end to the dare.
Challenge #8: Tips From Partners Past
Listen up, cuck. Your hotwife is going to tell you about the time another lover gave her amazing orgasms and had sex so good she’s never forgotten it. All while jerking you off.
Challenge #9: Shameless Flirting
There are two ways to approach this challenge.
The first is for the hotwife to flirt with someone while the cuck watches from a distance. She can do it somewhere physical, such as in a bar or nightclub. Or she could be text flirting with someone.
The second approach is IRL only, and involves both of you flirting with someone you desire. But only the hotwife gets to enjoy anything physical from this encounter (strokes of the leg or arm, a hug, a kiss, or more).
Challenge #10: A Kiss From Another
Some people find kissing extremely intimate, and keep it as a sacred sign of affection between them and their partner. But if you don’t feel this way, here’s where you can crank the cuckolding fantasy up a notch. Passionately kiss someone other than your chastity cuck. The cuck may or may not be present. If they’re not around, tell them about your kissing affair during your next intimate moment.
Challenge #11: Back in the Dating Game
If you’ve been together for a long time, then going on a date with someone new may feel both nerve-wracking and extremely exciting. I mean, dating has changed a lot in recent years. (Thanks, Tinder et al.)
Approach this challenge together. Look on dating and hookup sites for an ideal match. If possible, be upfront about not wanting anything long-term. (We’re not here to mess with other people’s emotions.) Tell them you just want a change of scenery for an evening, or a short-term, non-committed arrangement.
Hotwife, go on the date alone. It doesn’t necessarily have to end in sex. But don’t spare your cuck any of the details when it comes to how you felt being in a romantic situation with someone other than them.
Challenge #12: I Cam, I Saw, I Climaxed
Hotwife, log onto a cam site and engage in some online sex. Depending on the rules you’ve set, you can let your cuck watch you. If you do let them, tease them with a glimpse of who you’re playing with online. Prefer some alone time? Channel your inner Femdom and banish them from the room until you’ve finished.
Challenge #13: Get into the Swing of Things
Taking your cuckold fetish play out of the privacy of the bedroom and into a club is a big step. (It’s why this challenge appears so far down the list.) But going to a swingers event or sex club is a great way to meet like-minded people and explore the fetish further. So find an event in your area you like the sound of and head out to play.
Challenge #14: Find a Regular Bull
Get into a regular arrangement with a bull, and start to explore cuckolding with or without your long-term cuck in attendance.
Challenge #15: From Cuck to Cuckee
A final challenge, with a twist that encourages you to explore the role of the other person. In this hotwife dare, the wife becomes the cuckquean, and the bull dominates the sissy cuck. To turn them into the perfect toy for your bull (and to remind them of their subservience and humiliation in all of this) fit the Fufu Chastity Training Clip to their so-called manhood.
At the End of Each Challenge
Once the play has ended, spend time with your partner discussing what you thought and felt about the dare or challenge you just completed. Aftercare can be an important and very useful part of fetish and BDSM play for most couples. It’s a simple way to keep the lines of communication open as you get deeper into exploring your sexual turn-ons.
Which Cuckold Challenge Will You Start With?
These dares and challenges are designed to inspire you, and give you simple ways to start to explore the cuckolding fetish if you and your partner are new to it. Tell us which challenge you plan on starting with. And if you have some imaginative ideas of your own, we’d love to hear them. Share your cuckold challenge story.
