Hey Emma,
So, I have a dilemma and need your advice. I’ve been dating my boyfriend for almost a year now and he’s literally perfect in every way and even though we are new I can definitely see us getting married at some point. We’ve done a couple threesomes before, but during one, he got all nervous and had trouble staying hard. He said it was because he was worried about losing me, especially since the guy was hung and he got all insecure.
But here’s the thing – I absolutely LOVED the way he was possessive over me during that whole thing. It really turned me on to see how insecure he got about us, how much he cares and wants me and is afraid to lose me. It is addicting and I can’t stop thinking about cuckolding him. The idea of another man with me while he watches and shows me that deep emotional side of him…it’s just so hot to me.
I think he’d be into it, but I know he hides his jealousy because he thinks I’ll find it to be unattractive. But honestly, I love the idea of him being jealous in a way, like seeing his desire for me turn into jealousy as someone else gets to have me and he doesn’t. I just don’t know how to bring it up. I want to talk about it, but I’m not sure how to do it without making him feel insecure or uncomfortable.
Any advice on how to approach this conversation would be amazing!
Thanks so much,
Nadia
Hey Nadia!
First of all, I love how open and honest you’re being with your thoughts and desires—it’s so empowering to see that kind of self-awareness and excitement about your relationship. The fact that you’re looking to explore cuckolding with your boyfriend is really about tapping into something deeper than just physical intimacy. It’s about peeling back the emotional layers that come with vulnerability, and that’s where it gets really interesting.
When it comes to cuckolding, one of the most beautiful aspects is exactly what you’re describing—seeing your partner’s vulnerability and allowing them to experience a whole spectrum of emotions. That vulnerability is a gift, because it shows that your connection has depth and that there’s trust between you. You’re inviting him into a space where he can not only witness his feelings of jealousy, possessiveness, and desire, but also experience something very human—his own weaknesses, which is incredibly powerful. And as someone who likely values a deeper emotional connection, I’m sure you’re aware that seeing him in these moments of intense vulnerability makes him even more attractive to you.
Now, the big question is whether this is a direction he actually wants to go. It sounds like there’s a real emotional dynamic at play, and he may be opposed or he may find the cuckold threesome situation freeing in some ways—there’s less pressure to “perform,” so he can just be in the moment without worrying about any potential feelings of inadequacy. But it’s important to recognize that while you’re craving the intensity of that dynamic, it’s equally important to gauge whether he’s ready to share this part of himself with you. Is this something he’s genuinely interested in exploring, or is it just something that excites you and might make him uncomfortable or distant?
The good news is that you already have a foundation of trust, and I think if you approach the conversation from a place of compassion and understanding—reassuring him that the very traits he might fear the most (his moments of weakness, jealousy, vulnerability) are actually the ones you find most endearing—he’ll likely respond favorably. When you tell him that his emotional responses make him more desirable to you, that’s going to open up the door for a much deeper, more honest conversation. It will give him the chance to lean into his feelings instead of pushing them away, and that’s where the magic of emotional intimacy happens.
Also, remember that the cuckolding dynamic doesn’t just have to be about what you want, but about how it can enhance both of your experiences. You’re inviting him into something that allows him to experience an entire rainbow of emotions—pride, jealousy, desire, vulnerability—all of which are incredibly powerful and humanizing.
Kev and I have had our share of incredible experiences exploring cuckolding, but there were moments when he would have a less emotional response, and that started to spoil the dynamic for me. I realized that his emotional responses—whether they were jealousy, desire, or even discomfort—were a huge part of what fueled my attraction to cuckolding and deepened my desire for him. When he would shut down or become too neutral, it felt like something essential was missing. The rawness of his reaction, especially in the moments of vulnerability, is what makes cuckolding so intense and meaningful for me. It’s not just about the physical act; it’s about the intense emotional journey that we both take together.
We had an honest conversation about it, and I told him that seeing his emotions and reactions is what really drives me and heightens my arousal. He said that he gets accustomed to things and they don’t enact the same response so we brought in some light humiliation, a language between us that is undeniable. When I need more emotion from him, I can ask for it through humiliation, whether in a more gentle or a stronger and more direct way. It’s a tool I use to get the response I need, and he’s come to understand how it deepens our connection. Selecting partners with traits that I find attractive often align with traits where he has a thread of insecurity. Height, penis size, muscle definition, wealth; all of these things are ideas for selecting partners that may instigate the response you are craving. Through this, we get the emotional intensity we are truly looking for, and it lets us explore our dynamic in a way that feels both empowering and thrilling for both of us.
An obvious thing to consider is whether you’re both aligned in wanting this for your relationship. If he sees this as a way to connect with you more deeply, then you’re on the right track. But if he’s not yet comfortable with this idea, that’s okay too—it’s all about creating a space where you both feel safe to express and explore your desires.
I think this conversation is going to bring you both even closer, and if you approach it from a place of love and empathy, I believe you’ll see your boyfriend respond with an open heart. Don’t be afraid of him being uncomfortable or insecure during the conversation, emotions are a very deep part of intimacy and the best conversations in life will include some very real and uncomfortable feelings and the most vulnerable moments in relationships are the ones that bond us the most. Men are deeply wired to want to please you and you’ve already gone down the road of threesomes so you have the edge of knowing what to expect. If things don’t go as planned, consider some other relationship dynamics which might bring forth some of the excitement and emotion you crave without including a third in your bedroom. Male chastity, pegging or even role playing are great ways to experience a new level of sexuality together.
Good luck, and remember to be gentle and patient with each other.
With love,
Emma
