Molly's BDSM Tips | Should I Take My Cuckold Fantasy Further?

Stuck on how to take cuckolding to the next level? This week, our BDSM advice columnist Molly helps out one of our members who'd like to take his cuckold fantasy from bedroom role play with his wife into a real-life adventure.

Dear Molly,
My wife and I like to role play that I'm a cuckold. This is my fetish and fantasy that I talked her into doing, and she's been OK with it. We role play this regularly, and she is very, very good at describing sexual encounters, what she would do with a man as I watched. She is very fluent in verbal ***, and I love it.

My question is, should I seek to carry out my cuckold fantasy in real-life? If so, how should I approach her? She has in the past said she could never see herself actually doing it. For one, I believe she sees it as being unfaithful, and for two, she has self-confidence issues. She says that she doesn't find anyone else attractive and views me as her one and only. She also doesn't feel she's attractive even though she obviously is. So, do you think she would ever be convinced to try a real-life cuckolding adventure?
Cuck Desires

Dear Cuck Desires,
How wonderful that you've been able to share your cuckold fantasy with your wife, and that she has embraced it as a form of role play. This is a positive step for you both, and I can understand how you're now thinking of taking the cuckold fantasy further - and how you might achieve it.

Should a cuckold fantasy stay a fantasy?

The big question is, should you turn your fantasy into a reality? The answer to that is not a simple one, in my opinion, and really depends on what your fantasy is. Clearly, some fantasies are not practical to make a reality, for example, having sex with a tentacled beast is probably not something that can be recreated. Yet, tentacle dildos exist so that some elements of this fantasy can be explored. However, engaging in an actual cuckold scene is obviously something that with the right people would be fairly obtainable.

I think wanting to explore cuckolding for real is entirely understandable and doable. But, only if your wife feels the same way because it's not a kink you can explore on your own. The fact that your wife has been so open in exploring your cuckold fantasy is a hopeful sign. In time, she may be open to turning it into a real-life experience. Clearly, there are also issues with regard to her self-confidence and of potentially taking on the role of cuckoldress. The key is for you to build up her confidence and make her feel like she is the one who is in control.

Talk your cuckolding fantasy through

Be honest with her. Tell your wife that the idea of exploring this kink in some form is a huge turn-on for you. But, make sure that you acknowledge the issues she has with that idea and perhaps it's something in time you could work towards doing. Also, take some time to find out about her fantasies and desires not just in respect of cuckolding but in general.

You give the impression that she's doing this for you - and there's absolutely nothing wrong with that. Wanting to please your partner and help them explore their fantasies forms part of a healthy sex life. But it also makes me curious about what she might be fantasising about.

Try to create an open environment for discussion and encourage her to share her desires with you - as you have done with her. Maybe they will overlap and perhaps they won't, but they'll definitely give you more sexy things to explore together. I suggest that you find hot stories you both like and swap them. It's a great way to leave space for a partner to share what it is they find sexy, without saying the words. You can then spend time discussing the stories afterwards and ask what worked for her.

Introduce the idea of cuckolding slowly

One thing you want to do is think of ways you can help build your wife's confidence. This way, she'll hopefully be able to try out for your cuckolding fantasy for real with you. Perhaps suggest using porn as a type of 'stud'. Rather than watching her fucking another guy, instead she could watch porn that she finds exciting and masturbate herself to orgasm while you sit and watch. In that scenario, she could indulge in the verbal *** you enjoy and talk about how she wishes the guy on the screen was fucking her etc.

If she enjoys that, then why not suggest visiting a local swingers club? They're all friendly, relaxed places and happy for people to come along and just watch. Suggest you go for an evening but with the rule that you won't do anything the first time. Just observe, relax and chat with people. It could be a naughty little adventure for you to share together. Perhaps meeting other people and seeing them play will help her realise that if both parties consent, then it's not cheating. This could also help to boost her confidence.

What if cuckolding just isn't for her?

I think you should find a way to help your partner get to a place where both of you can indulge in a wonderfully sexy cuckold scene with someone. But, I also think you need to be prepared for the fact that she just might not be willing (or able) to take that leap.

If it turns out to be the case, then you'll have to decide if you're happy for your cuckolding fantasy to remain just that, or consider opening up your relationship so you could potentially find another partner with whom you could explore cuckolding with.

However, that's definitely something for down the line when you've exhausted all other avenues. I really think that with some time and space to grow your wife's confidence and learn her value as a very sexy woman in your life, then I am fairly hopeful that you can turn this fantasy into a beautiful reality for you both.
Good luck!
Molly x

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