Dear Jane: Advice For Boys Who Need It Bad
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June 2002

Advice for Boys Who Need it BadDear Jane,
I am 36 and my wife is 45. She has beautiful legs and size 6 feet. In fact, two of her photos have been in Leg Show. I have always had a fantasy of seeing her screw another man who is well-hung, like Ron Jeremy. When she has a few drinks I can almost get her to say yes to my fantasy, but when she’s sober she says she’d never do it. Is this a normal thing I want, or am I strange? Every time we go to Las Vegas she puts on a short dress and a pair of strappy sandals and a lot of guys whistle and stare at her. And she loves it. Let me know if I should convince her or just keep fantasizing.

Harry

Dear Harry,
You asked the most commonly asked question I receive: Am I normal? Of course, “normal’ is a subjective term, but I can tell you that yours is a fantasy shared by many men. And, certainly to a person who believes in the wonder of fantasy, like me, you are entirely normal. You’;re lucky to have a wife who appears to humor you, albeit when she’s tipsy.

In your case, precious, this is perhaps a fantasy best left in fantasyland. Why? For one thing, while you have a spirited wife, you don’t have a partner who’s given her consent. For another, the realization of some fantasies isn't as sexy or as fulfilling in the realm of reality as they are in imagination; sometimes, when acted out, they can be downright hurtful.

You actually are receiving the best this fantasy has to offer. When your wife dresses in short skirts and strappy sandals and wowing men in Vegas, she’s turning herself on at least as much as she is the men ogling her. And you’re the sole beneficiary of all her juice. It’s all part of the foreplay . . . she gets the attention, you get the fantasy, and, ultimately, you get laid.

Dear Jane,

I have been cross-dressing for over 30 years, but my wife only recently caught me in my wig and makeup, bra, garter belt, and high heels. After much duress we finally agreed I could wear panties when we make love, but I had to throw away my other girlie stuff.

My sexual performance has improved with the panties and my wife is fairly happy. She even bought me a pair of animal print thong panties for Valentine’s Day.

However, after a couple months under this arrangement, I knew I had to go back to dressing up all the way. I did enjoy my shopping spree for new women’s attire. Should I tell my wife that I can’t give up cross-dressing—and that I don’t want to? Or do I take my chances that she won’t catch me in the act again?

She told me if I couldn”t give it up we would have to go to counseling, but I know that I don”t want to give it up, even at the risk of our marriage.

Thanks,
Randa

P.S. I think you’re a wonderful and understanding woman, Jane, not to mention great-looking in pantyhose. I loved yours in the December issue, so silky and luxurious. Can you tell me what brand, color, and style they are? I want to try some, even if I won’t look as good in them as you.

Dear Randa,

You assume that going to counseling spells the end of your marriage. It does not. Choose a counselor who is familiar with cross-dressing and open to varied styles of sexual expression. Like you said, you clearly don’t want to give up your habit—you actually spend part of your letter asking after my own clothing (those pantyhose, by Frederick’s, are, sadly, no longer made). But, even if you wanted to, and even with a lifetime of therapy, I’m quite certain you wouldn’t be able to give up your love of dressing in women’s clothing. Go into therapy and, if you value your marriage, work to save it. That needn’t mean giving up your alter ego but it does mean being honest with your partner and yourself. Good luck. And, about the pantyhose . . . don’t be so sure you wouldn’t look good in them. I always notice how you cross-dressers seem to have amazing legs.

Dear Jane,

I’ve enjoyed your columns in Leg Show. Thank you. I need to share with someone a fetish that I have: women wearing leather. I just can’t get enough of it. It turns me on so much that I can’t contain myself. If I’m out at a bar or club and I see a woman in leather my dick gets hard right away and I make it a point to rub up against that woman just to feel the leather. The other evening, while taking a crowded train home, I spotted an attractive woman wearing a long black leather coat. I got myself in position so I was right behind her, so that when the train jostled around my ranging hard-on would be right up against her leather-covered ass.

I am also attracted to women older than me wearing leather. I am 35. I have a few other fetishes but I was wondering what you thought of this and what I might be able to do about it. Also, what’s your take on leather? Thanks for taking the time to read my letter.

Thomas

My Dear Thomas,

At 19, I took a trip to Mexico City. While there, I took a bus to see the Hermitage art exhibit. I wore a black leather coat. Even though the bus was crowded, I couldn’t help but take notice of a man standing especially near my right hip. The bus jostled and shimmied its way down the street. I heard the man take breaths that were increasingly full and deep. Naïve little girl that I was, I finally glanced down. And I saw that he was masturbating against my coat. The sheen of his pre-cum shone at the tip of his penis; he had worked himself into a nicely lubricated little groove in my coat just beneath my right butt cheek. At the next stop, I flew off the bus and ran down the street in tears. I share this memory and hope to the gods that in your enjoyment of this supple fabric you are keeping your pants zipped.

Having said this, and assuming you keep it in, not out, I appreciate your fondness for leather. I, too, find it a most sensuous fabric. Like the scent of sex, that of leather is like no other. Like skin—well, it is skin—leather is supple, pliable. And it’s symbolic too, of a rebel culture (as well as of a gay culture, but we won’t address that here). A man sees a woman in black leather and figures that she might be willing to take a walk on the wild side. And that might be true, if the girl wasn’t a 19-year-old from Colorado. I’m still partial to those glove-soft, black leather coats but I assure you that today I’d handle a fellow bus passenger such as I described quite differently.


Jane is the owner of X-traordinary Talk! and can be found on the Internet at www.xtratalk.com. Ask for Jane”s advice on any aspect of fetish sexuality by e-mailing her at jane@xtratalk.com. “Advice to Boys Who Need It Bad’ is a registered trademark of X-traordinary Talk! Please note that Jane”s advice is from the viewpoint of a caring, softly dominant woman; it is not intended to replace professional therapy. All questions are “real,’ although may be edited for length.

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