We have a good relationship and great sex
Ask Anna is a sex column. Because of the nature of the topic, some columns contain language some readers may find graphic.
My wife and I have been together for nine years. I’ve always thought it would be hot to see my wife sleep with another man. I found out early on in our relationship (months in) that she was still hooking up with her ex and found that super hot. Up until now we have only talked about it during sex but I told her I wanted her to find someone, have sex and then come home to me and tell me about it.
Well, apparently she knows this guy at work and they have been sexting. My wife is ready to sleep with him, which would satisfy my fantasy, except that I’m having trouble with it now that it’s becoming a reality.
Are safer sex barriers important?
I always thought if we did it, it would be a stranger and she wouldn’t see him again. And I’m also not sure if I’d like to keep it in the realm of fantasy or if I’m just nervous because it’s the first time.
Also, what if I ever met him? I’m going to feel uncomfortable because he won’t know I know, nor do I want him to because I find that more awkward, and what if he tells people she works with? Then I’d become the guy whose wife is cheating on him even though I would know. I’d almost want to watch (maybe).
For people who do this or have done this, was the first time horrible? Did they regret it? Did it ruin their relationship? — Looking For Advice
You’re entering uncharted relationship waters, so it makes sense that you have lots of questions, fears and concerns. There’s always an amount of risk when we invite new people into the bedroom (whether cuckolding is involved or not). And while a lot of your questions can’t be answered until and unless you try it out, there are many ways you can feel safer about this with your partner and to assuage some of those fears and concerns.
The first is to tell your partner your fears and concerns — have you? You’ve told her what makes you hard. Now tell her what makes you soft. There is nothing wrong with asking for reassurance from her and telling her exactly what you told me. This kind of vulnerability and honesty is what enables open relationships to retain a solid grounding, even as you leave the nest to explore other environs. (The bird metaphor is intentional, because the word “cuckold” comes from “cuckoo,” those sneaky birds that leave their eggs in others’ nests to raise on their behalf.)
I guess my concerns are that she actually really likes this guy and what that might do to our relationship
My second bit of advice is for your wife tell this guy what’s really going on. This will save you potential awkwardness if you do ever meet, alleviate any guilt or weird feelings that might come up with her or him, and makes it so your wife doesn’t have to lie, etc. Full disclosure is really best in these kinds of situations. Plus! If it goes well and you do decide to watch at some point, it’ll make that easier, too.
Third: Get 
really clear on your needs and express them to your wife. Are there certain intimate acts you’d prefer she not indulge in? How do you feel about sleepovers? PDAs? What kinds of care do you need to reconnect when she gets home — affection? Sex? A hot play-by-play? Assurance that she loves you? A stiff drink and a cuddle? Discuss and explore these things with your wife before the deed.
Fourth: You may very well experience jealousy. That is, after all, part of what makes this hot in the first place — the taboo, the breaking of those ingrained societal beliefs about what a marriage can look like. Jealousy is normal and natural in any relationship, and open relationships are no exception. Own it, talk about it, ride it out. Check in before, during (if it’s possible), and after the event. Ask her how she’s doing. Tell her how you’re doing. It’s basic stuff, but we can sometimes forget to check in when in the throes of newness and passion.
Fifth: You might try this out and find that you do not enjoy it in actuality. In which case, you don’t have to keep doing it. You can tuck it back into the realm of fantasy, knowing you gave it a go, and patting yourself on the back for being game to try. Which is way more than most people allow themselves to do.