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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.
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.
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. -- Jane Dear Jane: I am writing today to ask for your advice. I have an uncontrollable urge to wear women's clothing, especially pantyhose. As I am typing this I am wearing two pairs of black sheer-to-the-waist pantyhose, a small black and white checkered dress that buttons up the front, and a nice pair of black patent leather pumps.
-- Your Pantyhose Boy Dear PB: Gosh, pretty boy, why would you ever want to? Even I haven't had a heart-through-the-chest experience such as you describe, not since the day my partner presented me with red spanking panties, effectively and splendidly turning the tables on me.
You've found something that really excites you; explore the boundaries of your fantasies. Embrace your longings as you embrace your bared clitty-cock through the torn opening of your pantyhose. Now . . . grease it up for me, my pet, and put your trembling hands to good use. -- Jane
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