January 2002

Dear Most Captivating Jane,
You are exquisitely beautiful. Imagining what your elegant and intimate private wardrobe must be like inflames my feelings of passion and desire; manifest now by a rather full and tormenting engorgement. I love your advice. I need some now, since I find myself in the most peculiar quandary.

I have been with a very talented professional dominatrix several times now. I know that I am totally submissive and I’m fine with that. I was perhaps surprised though to discover (what I will call for lack of a better term) my inner slut. The domme took me in places and to places that I hadn’t quite expected. No apologies needed, I had a great, droolingly submissive time of it.

Here’s my problem though. While the experiences were satisfying in any number of different ways, they were distinctly lacking in any sort of soft, seductive teasing. There was no subtle interplay or insightful psychological manipulation of a submissive’s anticipations or hidden desires.

Am I doing something wrong as a submissive? Am I simply expecting too much? Now that I’ve discovered my inner slut, how do I keep “her” satisfied? Rather than finding my submissive self, it now seems like I’ve discovered many of them. Please advise. Sending my most gracious thanks and devoted enthrallment.

Samuel

Dear Samuel,
In your letter you have eloquently captured the dynamic between dominant and submissive that I myself find so exquisitely erotic: an engagement of minds. Once this is achieved with a lover, it requires nary more than a raised eyebrow to take a man to that place where his eyes glaze over, part of him is as hard as a diesel engine, and the rest of him is putty in my hand. Ahhh . . . bliss! When you find a woman able to crawl inside your mind and act on desires you haven’t even thought of yet, you will know the nirvana of sex.

And this can happen to you, sweet Samuel. But perhaps not in a professional setting. You need to be clear on expectations so that the inner slut crying for release will be satisfied. Many dominatrices do exactly what they’ve been asked by the client to do. Yet men are not, in their own minds, clear about what it is they want and so they’re left oddly unsatisfied, even though she did what he asked. There’s only so much a professional dominatrix—many taking credit cards and charging for 50-minute hours—can do. And many are clueless that what their clients want is a transporting of his mind, not just a spanking or bondage session. They fail to understand that simply doing to a man, while pleasurable, is often not truly what a man wants.

And what does he want? I may be no more knowledgeable than Freud was about women, but I can give it a shot; your letter gives clues Freud never had. What I believe you want, above all else, is to be understood. You want your partner to teasingly tempt and erotically bewitch you into going to the same mutually-satisfying place sexually. Ultimately—brace yourself—your letter tells me you want a relationship. And it’s more difficult to cultivate a relationship in three-hour paid sessions with a professional than it is with a woman with whom you go on walks, have ice cream, and talk about matters of the day. That’s why, I think, I receive more letters asking for help in getting wives and girlfriends to participate in their particular brand of kink than requesting the name of a professional. Because they know, at least on a subliminal level, that the place they need to go in their sex is one that requires safety, intimacy, and a true knowledge of one another, in and out of the bedroom.

Be true to thyself, sexy Samuel, and enjoy your “very talented” dominatrix for what she has to offer. Then ask another woman you know and like out for coffee. And hold out hope that you will be the catalyst to bring her latent “dominatrix” to the surface.

Jane

Dear Jane,
I have been a cross-dresser for the last thirty years or so. It cost me my first marriage. She knew that I dressed, but never could accept it. We simply grew apart, and I swore I would never let my fetish affect me like that again.

I am now remarried, and my new bride loves the fact that I wear panties every day under my business suits. In fact, she often shops with me to buy scanties we can share. She adores my female side, and encourages me to let it out. I think she’d like to be my lesbian lover.

The problem, however, is that she doesn’t want me to go all the way, and dress completely like I used to. I once put on a bra during lovemaking, and she asked me to take it off. It doesn’t turn her on.

What can I do to encourage her to allow the real female in me out? I would love to be able to dress up and be her “best friend,” as well as her lover. But, I’m worried that she will think it’s too much, and leave me, like my first wife. I need the time I used to have as a female, but I love her dearly and don’t want to lose her. What can I do?

Perplexed

Dear Perplexed,
First of all, dear one, I laud you for having apparently let your new bride know before marriage that you like to dress in women’s clothing. I recently conducted a survey of my clients and found that a scant 10.5 percent disclosed this important detail prior to nuptials. Keeping an aspect of ourselves as integral as our sexuality secret from the person closest to us is a recipe for a life marked by shame, guilt, and loneliness.

You say your beloved embraces your “female side”. She celebrates your wearing panties under your suits. You say you think she’d like to be your lesbian lover. Well, lucky boy, you’ve hit the lottery: it appears you have found a partner who is playful, open, and willing.

However, there’s something about fantasy that you must understand, precious girlyboy. And that is that one person’s fantasy may not be his partner’s and may never be, as much as both parties may want to go there. As open as your blushing bride is, she may not be able to cross the line between panty-wearing and full cross-dressing. If she crawled into bed wearing a shirt and tie and boxer shorts expecting you to be turned on, you might understand.

This is not to say that there’s no hope in engaging her interest. You have a woman in your life as playful as any man can hope for. Why don’t you invite your muse for an evening of play devoted to a lesbian fantasy. If she’s actually involved in transforming you into her female lover—and witnessing your excitement along the way—her own panties may dampen far more readily than they did when you simply showed up in bed wearing a bra. Let her play with you. And if she still doesn’t go for it, then value all she does give you—which is a lot—and stop focusing on what she doesn’t. After all, you always have your old girlfriend to turn to when the need arises, right under the surface of your own skin.

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