Advice: The Benefits of Dipping Your Toes into Cuckolding

Cuckolding is one of the few kinks where the couple has to invite another person into the bedroom, and that’s a significant part of what makes it so difficult to integrate into a relationship. Suddenly, your twosome expands to a threesome, even if it’s just for one night. Things can get complicated with remarkable swiftness, especially since good sex and the relationship building that sometimes precedes it can lead to unexpected feelings and desires that might not be compatible with a healthy marriage (or long term relationship).

That’s why, when I’m asked, I almost always recommend dipping your toes into cuckolding before you fully commit as a couple. I know some people are really impatient to just get to the real thing, but it’s my belief that your transition to the real thing will be a lot easier if you’ve had a little bit of practice beforehand. I’m not saying every couple has to adhere to this advice (that’s why I also advise lots and lots of communication since every couple is different), but in general I think it can be exceptionally helpful.

There are a handful of ways I can think of to dip your toe into cuckolding that don’t involve inviting another man into your bedroom. You could:

• Read Dirty Stories Together – I actually have experience with this one. My husband and I used to read Penthouse Letters to each other. We stumbled upon a book of them at the bookstore, bought it on the spot, and started reading that night. I don’t remember any outright cuckolding stories, but there was plenty of hotwife-style content that we both found enormously sexy. I clearly remember how turned on he used to get, which is why I ended up getting into writing erotica in the first place. I’d recommend choosing stories that run a lot closer to the hotwife dynamic, at least at first. They’re almost always about the wife having mind-blowing sex with another man, and as you know, a good cuckold puts his wife’s needs first because he knows that’s how he gets his needs met.
• Use a Toy on Her – It’s nowhere near watching her have sex with another guy, but you might find it quite pleasurable to use a lifelike dildo on your wife (it also doesn’t have to be lifelike if she’s not into that). You might also find it pleasurable to watch her use one on herself. Please keep in mind that dildo penetration is usually not enough to make someone cum, so she’ll need clitoral stimulation as well. You can manage that though, right? Use your tongue or your fingers while you slowly, gently fuck her (go faster if it’s what she wants) and give her an orgasm while commenting on how hot it looks to see the toy slide in and out of her. She might get the hint and be willing to put on a show for you where she fucks herself while you watch and masturbate. Perhaps she’ll even be willing to segue into fantasy play and talk dirty about fucking a guy while she uses the toy.
• Have Her Tell You an Ex-Boyfriend Story – If your wife/girlfriend has been with other men there’s a chance she has a memorable sex story to tell you. She’ll need to have some understanding of your cuckold fantasy to be into this, but if she does, it should be thrilling for both of you. If she’s comfortable, she should be able to get turned on while she tells the story and you both masturbate. You can also do it while having sex. Please take care not to get too lost in your quest for an orgasm. You want to make sure that she’s enjoying herself too. The way you go from fantasy play to becoming an actual cuckold is to make sure she’s having almost as much fun as you are.
• Online Flirting – This one is a step further, but it’s also pretty easy to do some online flirting and dirty talking with another guy and it’s possible to be entirely anonymous. You can use the /r/dirtypenpals subreddit to find likeminded people to write with. You can sign up for a Fetlife account to chat with kinksters. You can use a dating app for some flirty fun. You could also just browse profiles and talk to each other about how much fun it would be for her to fuck one of the guys without ever getting in touch.
• Mutual Fantasy Play – You can concoct a fantasy together. This works best if you’re both turned on and playing with yourselves (or each other). Once you’re worked up, you can start building a fantasy together. Talk about where she’d meet the guy and what he’d look like (Are you on vacation? Is she on a business trip?). Talk about how they flirt. Talk about how they’d have sex. Talk about whether or not you’re watching. There’s a chance she won’t be into that sort of thing, but if she is, you’re that much closer to your cuckold fantasy becoming a reality.

I’m sure there are other ways of accomplishing the same goal, but you get the idea. Instead of jumping right into cuckolding, you’re giving both you and your wife a chance to get comfortable with the idea and to explore that there’s real pleasure to be found in it.

I can’t promise that this will work, but I do believe it’s a far more acceptable way of introducing the idea of cuckolding to your partner. You’re not asking her to go out and fuck someone else. You’re simply asking her to consider the idea of your fantasy and to give you a little bit of pleasure while receiving plenty of her own.

Don’t try and force it, though. Listen to her if she says she’s not interested. Try and find out how you could make her interested. Make sure you’re always putting her pleasure first as that’s a great way to show her that you’re not being selfish and that you’re actually interested in both of you enjoying your fantasy. Also, ask if she has any fantasies. Perhaps you’ll be surprised.