December 2003

Big, Sweaty Sex Toys
Dear Jane,

I’m a forty-year-old healthy, obedient, feminine nice guy who needs your trusted, thoughtful advice.

I have an embarrassing confession: Over the past few years I have had an anal addiction. I plan for it, anticipate it, and enjoy it with an obsessive passion.

My daily routine is as natural as my morning coffee. My two showers per day involve a very long and hard toy ride that I’m sure my neighbors can hear. I look for unusual objects while shopping, wear one of my several plugs daily, and only wear thongs for a nice, snug fit. I’ve even used my toys attached to my electric drill. As I write, I’m wearing a plug I bought in October of 2002, when I discovered my first issue of Leg Show.

Also . . I’ve been straight so far, have been married, and have had several Leg-Show-quality girlfriends in years past. Please see my personal ad in the enclosed magazine. It may be of interest when you write back.

Jane, do I sound like a guy who needs help?

I hope you don’t mind my silly photo being enclosed also. I love modeling for the camera. Thank you for your understanding and any advice you may have.

Anally Addicted

Dear AA,

That word “obsessive” raises a red flag, but as long as your power drill’s not your only friend, you’re not hurting yourself, and you’re not at home shoving something up your ass when you should be at work, there’s nothing wrong with you. No, baby, on that score you don’t need help.

But there’s another, bigger question you pose between the lines: your sexual orientation. Sweetie, do you really expect to meet a woman by placing an ad in a rag featuring Mr. Gay Wisconsin? Or with your ad seeking a woman who’d like to see her “husband, boyfriend, or next door neighbor . . . pound me long and hard from behind” as she watches?

Really now. Do you want advice, darling, or do you want me to play guess-my-sexual-orientation with you? You’re not an inept heterosexual, but a sweet gay boy (maybe bi, but I doubt it) who’s in denial. And it’s not because of your desire for lots of anal pleasure that I say that. Plenty of het men adore the same thing. It’s the combination of things: you read gay magazines, place ads for women that are really for men, and take pin-up photos of your slender, hairless, suntanned, very pretty body. Yep, I rest my case. Sweet baby, give in to your desires. There’s no shame in being gay. Even in Wisconsin.

You’re yummy to look at and you’re horny—the prime qualifications you’ll need when you venture out from behind your shower curtain. Admit that you want a big ol’ sex toy that’s strong, sweaty, meaty, and will call you the day after. Look at the ads in the Mr. Gay Wisconsin rag and find one.

Ruler of the Pussy
Dear Jane,

Tell me the truth: Do guys with small dicks get laid less than guys who are normal-sized?

Shortchanged

Dear Short,

I have no doubt. But why has nothing to do with their size.

I spent a day at a clothing-optional hot springs in northern California recently. As I lay in the warm sun, I scrutinized every naked cock that dangled by. Why? Why—after never before caring—did I waste my time examining these bobbing symbols of manhood? Because of YOU, that’s why. You silly boys have brought up the question of penis size so often that I finally took note. You are so insecure, so paranoid, so focused on this one little thing (oops, excuse me) that you finally affected me. For the first time in my life, I looked. Worse, I judged.

Some dicks I saw were so small that all I could see of them was the head, flush up against the body. While most of the other men bounced as they strolled, these little stubs stayed squarely in place. I wondered how they peed; did their stream shoot straight out? Never before had I even thought about it, but now I pitied them, hoped for their sake they were not planning on getting into the cold plunge. The small ones are usually possessed by overweight men (remember, poundage gobbles up those manly inches).

Long schlongs were worn proudly by their owners. These “show-ers” verily strutted with confidence, giving credence to my theory that a big penis begets a big head. They smiled readily, approached women more easily.

And that’s why bigger ones see more action. Not because of their size, but because of their owners’ confidence.

However, knowing you’re average or even smaller than isn’t going to make it any bigger, so get over it. Little guys see plenty of pussy; if they didn’t, the gene for smaller ones would’ve died out eons ago in survival-of-the-fittest.

Instead of cock, let’s focus the true ruler of the pussy: the tongue. Why don’t you bad boys write to me about your tongues? How big are they, how good at giving exquisitely wet, intimate pleasure? It’s time to be hung up on something that actually matters to us women. You boys so consistently relate the amount of pussy you get to your dick size . . . when you should be concerned with the facility of your tongue and the technique that lies therein. That, dear boy, is your secret weapon. For, he with the best tongue is he who actually gets laid most.

Stuck Between a Rock and a Hard Place
Sweet Jane,

Recently my wife of 27 years finally learned of my cross-dressing desires as a result of her finding some hot fiction I had downloaded. She loves me as always but said to me, “I want a real man.” I told her cross-dressing was an area of sexual arousal for me that helped me fulfill some needs unmet by her.

She is content with occasional sex. I basically told her I need to get off almost daily (not telling her it was really more often than even that). I told her I wasn’t going out cross-dressed (true) and that I satisfied myself with my inner fantasies (although I occasionally use phone sex lines like yours). She told me that the whole thing “disgusts” her.

The first time I tried to dress for her many years ago she was clearly turned off. I was wearing stockings and a nightie. Clearly that is not an avenue we will go down together. I guess she’s o.k. with my desires as long as she’s left blissfully unaware.

I would love to dress HER up really sexy and do her makeup (I just love makeup) and have suggested this in the past. I wonder if that avenue had been open years ago in our marriage that my own fetish would never have taken root. I also mentioned that she could just masturbate me and whisper a fantasy scenario in my ear, but that hasn’t ever happened, either.

So what is left? She does make both loving and occasionally cutting remarks about whether I have taken her clothes or ordered something from Victoria’s Secret—and that is better than it being hidden entirely. But I do long for dress-up games with a pretty woman (btw she is very attractive and men give her looks all the time).

I am stumped as to what, if anything, I can do. Any ideas?

Jim (Jenny)

Dear JJ,

First, take responsibility, JJ, for your sexual desires. To tell your wife that cross-dressing helps you “fulfill some needs unmet by her” is to imply that she is the cause of this predilection. No wife turns her husband into a cross-dresser. No matter whom you were married to or how she responded to it, no matter if she had let you dress her up so many years ago—no matter what—you’d want to dress in women’s clothes.

Women married to cross-dressers can be turned off for a variety of reasons, among them: because the idea of a man in a dress is socially taboo and therefore, to use your wife’s word, “disgusting.” Or because the wife feels in competition with him (we don’t like having our angora sweaters stretched out, so stop borrowing them). Or because their otherwise-wonderful husbands are so focused on their own cross-dressing needs that they abandon the needs of their wives. Or because—and your wife implies this when she says she wants a “real man”—she fears you’re homosexual.

You’ve lived 27 years of secrecy, indicating there’s not much feeling of safety in your marriage, perhaps on either side. In addition, having kept your cross-dressing a secret indicates that you yourself don’t feel entirely comfortable with it.

You’re stuck between a rock and a hard place, the “rock” being your wife and the “hard place” that bump inside your nylon panties. You’re asking “what, if anything” you can do.

Even if you never convince her to play makeup and dress-up with you, you can still enhance your relationship and it would behoove you to do so. This weekend start committing time to romancing her often. If you know what she finds romantic (and I hope that after 27 years you do), do it for her. Don’t ask for anything in return. Fantasize about dressing up if you need to, but focus on her. Even if she never plays dress-up with you, it’s a wonderful feeling to give your partner that light-headed feeling of sexual bliss. What you’ll get from giving to her in this way is a wife who’s more accepting of you and perhaps more patient with your proclivities.

Then, be realistic. You can’t engage someone who doesn’t want to. What if she wanted you to get excited by her dressing up like a chicken . . . ? Just because she loves you—and you her—doesn’t mean you’ll find your charge in the same activities. In the end, at the very least you’ll have a more loving partner.

Finally, don’t negate the power of fantasy—and a pretty frock—to fulfill your desires, precious. They’re always accessible and they know exactly how to please.

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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