I’m thinking of hiring an escort to surprise my husband; I know he’d love it, but I’m not sure how I would react to it. Any advice?
It’s a lovely idea, and the fact that you’re even considering it puts you in the class of cool, laid-back and sensible wives. However, there’s often a gap between the spirit and the flesh, so there are several factors you ought to consider before actually going through with it. First, you need to consider how jealous you might be deep down; though the very fact you’re thinking about this shows you aren’t sexually insecure, jealousy is a visceral reaction and it could surprise you. Have you ever felt a twinge of it when you’ve seen your husband dancing with, flirting with or talking to another woman, or when he discusses old girlfriends? Because if you have, you need to think about how you might react to watching him actually fuck another woman in front of you. Even if it’s just a subtle discomfort, it could mar your enjoyment of the experience and even affect the way you feel about him immediately afterward. As I always tell couples before we start, we’re there to give both of you an exciting evening, not to cause trouble between you. So do think about how you might feel, and if you have a unexpectedly-negative reaction during the date you need to be honest about it rather than trying to bury it.
Another important factor is your relative level of bisexuality. You didn’t mention what exactly your husband has said about three-ways in the past; do you think he just wants two women working on him, or would he like to see you making love to another woman? Because lesbian contact between the women is an integral part of many men’s fantasies about this subject, you should be prepared for that; if you’re bisexual or strongly bi-curious this is a moot point, but if you’re neither it would be a good idea to think about how you would feel about kissing another woman, or having her go down on you. I think it would be an excellent idea for you to read my two-part “Couples” column, which goes into depth about couple calls from the escort’s point of view; the second part compares one that went really badly with one that went really well, and I think the differences may be instructive for you. If you decide you do want to try, here’s my advice on finding a good sex worker for the job. Good luck, and have fun!