Given the delicate nature of cuckolding, it’s something best done together, to be honest. Every cuckold couple is different and has varying needs that should be met. Before you can consider being with another man, you have to find out what your husband wants out of the experience and consider if you can meet his needs.
It should be more than one conversation. If he says something like “I just want you to be with someone else, that’s it,” there’s probably more to his fantasy. It’s okay that he doesn’t want to reveal it all (a man needs to be very comfortable with vulnerability to explain his cuckold fantasy to his wife or girlfriend), but you’ll want to know more before you actually sleep with someone else.
One of the problems with making any sexual fantasy a reality is that it’s hard to make the real thing as hot as what happens in a guy’s (or girl’s) mind. What if he hates the idea of you kissing someone else but wants you to have sex with someone else. That might be a deal breaker. These are things you should know before diving in.
That’s why I recommend taking it slow. Maybe you have your husband watch from across a coffee place as you go on a first date with a guy. Maybe he gets to see you share a few kisses with the guy. If that turns you both on, then you can take it to the next step.
If you’re really going to work cuckolding into your marriage, you have years, probably decades, to get it right, so there’s no harm in taking your time and having as much fun with it as possible. Remember, despite what you’ve read online, each couple is different and there’s no step by step way to approach cuckolding. You need to figure it out together. There will almost certainly be bumps and setbacks along the way, but if it’s right for your marriage you won’t regret it.