Can cheating ever lead to healthy cuckolding?

It’s not a good start. Cut your losses now.

Agree with needburr that cheating is not the best way to start a marriage. You do not say whether her boss is married with a family. If he is it is less likely that you are just a placeholder until she lands him.

I hear how tough this situation is for you, and I’m sorry you’re feeling humiliated and ashamed. The number one thing in a marriage is mutual respect and admiration between partners. Cuckolding can be a fulfilling lifestyle, but it has to be for both people in the relationship. If one partner feels unhappy, disrespected, or pressured—like you do with this ultimatum—it’s a red flag that could lead to resentment down the road.

Your love for your fiancée is clear, but her actions, like not showing remorse and expecting her boss at the wedding, seem to disregard your feelings. A healthy cuckold dynamic thrives on open communication, consent, and mutual excitement. If you’re feeling ashamed rather than excited, it’s crucial to talk to her openly about your emotions and work toward a mutual agreement that respects both of your needs. Without that, it’s hard to see this leading to a healthy relationship long-term.

For context, my wife Priya works in corporate and has been intimate with multiple bosses. Early on, she’d tell me beforehand, like, “Honey, my boss invited me to a hotel, I’ll be late.” I’d kiss her and say, “I’ll be waiting to hear all about it.” Over time, she started meeting them spontaneously without telling me first, but I was okay with it—I was actually impressed and proud of her confidence. What makes it work is that she always respects me, includes me in every step, and shares every detail, which strengthens our bond. Sometimes, she even brings home intimate moments, like when her bosses would cream-pie her she would come home take me to the bedroom make me lie down on the floor sit on my face slide her panty to the right and spat all the cum right into my mouth the sweet nectar flowing from her pussy was her love for me letting me taste her after her encounters, which feels like an expression of her love and our shared journey.

Your situation sounds different because you’re not on board with her actions, and that’s okay. My advice: have an honest conversation with her about how this makes you feel. If she’s unwilling to meet you halfway, it might be worth reflecting on whether this dynamic can work for you without building resentment. A marriage should lift both partners up, not leave one feeling humiliated. Wishing you strength