Honestly, to begin with I’d go to Fetlife or something and ask this to active cuckolds and hot wives. How did people start? What challenges have come up? Do they feel secure in their relationships? Any stories where it went horribly wrong? That kind of thing - anything to get a peek at what this kind of thing is like IRL.

Next, take a hard, unsexy look at your fantasy. What are things that would make this unpleasant for you? Some dudes like being verbally humilated during this stuff - would that be you, or would that hurt? What is your connection with the guy - have y’all had a grownup talk about what everyone wants? Is it just some random guy at the resort? What if you find they are texting after your vacation - is this hot, or traumatic? What if she wants you to do something with the guy (pretty common) - down, or no way? What if she wants to fuck him and you’re not present - cool, or no? And so on.

Once you’ve got this sorted, in terms of approaching the conversation, common pitfalls to be acknowledged, and your hard and soft limits, then talk to your wife. Say you’ve had this fantasy, and want to know if it’s something she would be interested in. What concerns does she have? If she’d otherwise be game, how do you manage those? Talk it out so that a) you both can determine if it’s something you want to pursue, and b) in such a way that everyone feels super turned on and excited about the activities, with any risks to folks’ feelings controlled for to the best of your ability.

It’s not for everyone, but if you think it through, communicate consistently and honestly with your partner, and respect each others limits, it is for some.