Dear Dan —
I am a straight, 45-year-old, monoga-mous male. I am married for the second time, to a wonderful 42-year-old woman. The few times I shared fantasies with my first wife, she used them as weapons in the many battles we fought over the years. She also betrayed my trust by sharing these fantasies with others. Fast-forward to wife number two. She is fabulous. We can talk about anything. She is respectful of my trust issues and has helped me immensely in getting over much of it. When she says, "I'll think about it," she really does. I never feel dismissed. And the sex has been amazing. We have explored things I only dreamed about. Anal sex, public sex, sex toys, and video cameras are all part of our routine now. She asks me for things, and I try them. I ask her for things, and she tries them.
So what is the problem? I can't bring myself to ask her for two things that are more than bucket-list issues to me. I am a closet crossdresser. I want to make love to her in stockings and a teddy. I made this request to my ex, and it resulted in humiliation. She even shared it with my son out of spite. And I want us to try watersports. When this came up during marriage counseling with my first wife, the counselor blew up at me and accused me of degrading my marriage.
So how do I screw up the courage to ask wife number two, the good guy in bed who always listens and never judges, to let me dress up in women's underwear and make love to her and then have her pee on me? Just writing about it is making my stomach twist, but when I look into her eyes and feel the trust, I almost blurt it out. I won't die if these wishes go unfulfilled, but I would die if my second wife stopped respecting me.
Pretty Under Normal Things
You love your new wife, she loves you, you're both GGG—it all sounds so good, so functional, especially compared to your nightmarish first marriage. Congrats. But you held your two biggest kinks back from the new woman in your life, PUNT, and now you're sweating the reveal because the stakes are so high. This is precisely why I urge people to lay those kink cards on the table early. The longer you wait, the more emotionally invested you become in the relationship, the higher the stakes. Because what if your kinks aren't just things your second wife isn't interested in exploring, PUNT, but attraction-killers?
My advice: Instead of having an open and honest here-are-two-things-I-wanna-do conversation, PUNT, go with an indirect here-are-two-things-some-people-do conversation. Find a way to broach the topics of crossdressing and piss play without having to admit that they turn you on, e.g., go see a drag show (drag isn't crossdressing, of course, but it will allow you to broach the men-in-dresses subject generally) and find a porn film with one brief, not-too-hardcore piss scene in it and watch it together. Pay attention to her response. If she reacts in a neutral or positive way to men in dresses and/or piss play, lay those last two kink cards on the table. If she reacts negatively, you might just die with those wishes unfulfilled.
Pro tip: Nervous kinksters can screw up indirect here-are-two-things-some-people-do conversations by telegraph-ing disgust. Someone who's into rubber says, "Isn't it weird how some people get off on wearing rubber clothes and gas masks?" The non-kinky partner picks up on the word "weird" and responds with, "Yeah, that rubber stuff is fucked up." If you set a negative tone, your wife is likely to pick up on that. So keep your reactions—at the drag club, during the porn—as neutral as possible.
This week on the Savage Lovecast, Dan chats with the amazing Mistress Matisse about where kink comes from, fantasy BDSM versus nonconsensual abuse, and how to meet a kinky mate. All at savagelovecast.com.
My newest book—American Savage: Insights, Slights, and Fights on Faith, Sex, Love, and Politics — has been called one of the best books of May by Amazon.com, and Publishers Weekly says it's one of the best books of the summer. And it comes out this week. Look for American Savage in bookstores now!