Dear Jane: Advice For Boys Who Need It Bad
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March 2004

Advice For Boys Who Need It BadDo-It-To-Yourself Domination
Dear Jane,

I am an otherwise normal guy and I have recently discovered a new way to explore self-humiliation and soft domination without a woman even knowing the pleasure she’s giving me.

My procedure is quite simple. I dress in my usual business suit and tie and go to a shopping mall by myself at lunchtime. A man usually receives instant attention in women’s boutiques. I am usually approached by attractive saleswomen inquiring whether I need assistance. Most of these women are quite helpful and undeniably curious. The looks I get when browsing racks of lacy underthings are priceless. Although I know my size, I sometimes ask whether a particular style of panty “runs large or small” or whether a particular thong might be comfortable.

Women have a particularly brutal weapon in their arsenal when it comes to humiliating men: their dismissive (and sadistic) giggle. I am often the target of that weapon when I boutique-shop for panties; I love it.

On one expedition, I dared to shop for a bikini swimsuit. I allowed the salesgirl to assist me in choosing a number of cute bikini styles. I asked her opinion on which suit was the cutest. She commented on the bandeau style top on one of the suits—which is when I interjected that I did not think I would be wearing the bandeau, just the bikini bottom. The shock on her face alone, when she realized the bikini was for me, was worth the price of the suit. I asked her whether I could try it on to check fit. She looked amused and pointed me to a dressing room crowded with young women. I could hear excited giggles and whispers as I changed into the tiny bikini bottom. It fit and I bought it.

I do not consider myself a cross-dresser. I do not want to become a woman or make love to a man. I enjoy the thrill of the hunt and the conquest of making a forbidden purchase on the turf of the opposite sex. I keep my purchases as trophies. What are your thoughts on this unusual kink? Can you suggest a means of making it even more fun?

Panty Purchaser

Dear PP,

Since you’re not asking for insight, bathing-suit beauty, I must resist the urge to unravel your “unusual kink.” For instance, I wonder whether you’re not in a relationship and need to be dominated and humiliated—by someone, somewhere. . . or whether you do have a partner but she’s not accepting, so you seek acknowledgement elsewhere; your true self needs to be known.

It doesn’t matter what the core of your kink, though, because you don’t present your activity as being a problem for you. Curiously, neither do you present it as a huge turn-on. On the face of it, you strut into lingerie stores and subject unassuming clerks to your stunts for no other reason than to satisfy your need to be the center of attention. It’s not a turn-on you seek but shock by the clerks. Such a cocky little panty boy you are, feeding an apparent self-infatuation with your little games.

Doll, you’re playing in the minor leagues. It may work for you to play with the naïve lingerie clerks at the mall, but, really now . . . You can’t think your letter—or your activity—could possibly elicit the same reaction from me. You know I’ve seen it all, bad boy—and then some. Next time you write, come up with a game of erotic self-humiliation that’s more worthy of my time and where the stakes for yourself are far higher. Say . . . a game with a woman you actually know.

Will Work For Permission to Cum
Hello Mistress Jane,

I’m a 21-year-old male in the UK. I’ve got quite a few questions about my cock and what I do with it.

I can’t stop wanking. I just want to keep doing it and doing it. I’m finding that just any sexy lady sometimes isn’t enough to get me hard. Does this mean I have been overwanking? Will I eventually run out of semen?

I like women with long sexy legs in stockings. This gets me rock hard. But mostly what I like is tease and denial, which is what brought me to your site. It’s a total turn-on, the idea of my cock in a sexy woman’s control, telling me what to do and when to do it. Since discovering this, as I sit in front of your site being teased, I’ve noticed that I begin to ooze something out from the tip of my cock. It’s clear and sticky but I know it’s not cum. Any idea what it is?

I find you very sexy and want to cum for you, but have not done so as I think you should permit me to do so. Can I please cum for your sexy body? I promise to bow under your conditions. And I hope you can answer my questions. Thank you.

Too much?

Dear Too Much,

No matter how much you are wanking, it’s not possible to masturbate too much. Besides feeling good, it’s a wonderful way to learn about how your body works sexually. Surveys on the web site www.jackinworld.com indicate that men your age, on average, masturbate 8 times a week. But, really, doll, even if you’re pulling on it 42 or more times a week, don’t sweat it. Some web sites ominously warn that you can “overmasturbate.” Never mind these; they just want to sell their worthless products. The only “cure” for horniness is, of course, sex itself—as a couple or solo. And, as you’ve seen, even that’s no more than a temporary solution to a problem that is, well, not a problem at all but one of life’s pleasures.

A problem can arise not from the activity itself but from the place it occupies if we are furtively engaging in it instead of showing up for our life. For example, if you’re compulsively jerking off when you should be getting to work or a date you’ve made, you might examine your, umm, hobby.

For long-term wanking pleasure, use lubricant so you don’t rub yourself raw. The skin on the penis is some of the thinnest skin on your body; hence, it’s delicate. Your cock is good to you; return the favor.

Will you run out of semen? No more than you’ll run out of saliva by spitting. Men have a semen-producing factory that works 24/7. Of course, the more often you jerk off, the less semen will have been built up for your next session. Since most men equate orgasmic pleasure with quantity of semen ejaculated, you might want to delay orgasm before ejaculation . . . indicating that tease-and-denial is not only enjoyable but productive as well.

The bit of drool oozing from your cock is pre-ejaculatory fluid secreted by your Cowper’s glands—pre-cum. This clear fluid neutralizes any acids from urine that may remain in the urethra, paving the way for sperm to pass safely when it’s ready to shoot. Pre-cum also lubricates the end of your penis for penetration. Some men have more of it, some less. Either way, it’s entirely normal.

Will I grant you permission? Of course, sweet boy. But you’ll have to work for it; remember, good things cum to those who wait. First, live 24 hours of your life without touching your willful cock. Good and horny? Oh, most certainly; I like that. Now, lubricate your hungry cock for me and stroke yourself to hardness. Listen carefully, bad boy: I said to stroke yourself to hardness, not to conclusion. You may not cum until you first demonstrate to me that you have the control necessary to make yourself stiff without coming. Do this three times. Each time you’re hard, take a swipe of your pre-cum and lick it off your fingers. Good. Now let your sweet cock deflate; show me how soft and compliant you can make it for me. Good boy. OK. Now you’ve earned it. Tug and pull your lubricated member again. Look down at your big, fat glistening cock in your hand, sweetie. Yum. Now have your cute little squirt, doll. And, as you have it, naughty boy, thank me for allowing it.

Single Man Seeks Single Woman in Pantyhose
Dear Jane,

For as long as I can remember (I’m 37), I’ve had a thing for pantyhose, stockings, and high heels. As a teen-ager, I would raid my mother’s dresser drawers and masturbate with these things. Many times I asked myself whether I was gay. I have no attraction to men, just a love for the feeling of silkiness against my skin.

In college I lost my virginity to a slightly older woman who taught me the joy of caressing nylon-encased leg and smelling the heat that is held in by pantyhose.

I married at 20; I let my wife in on my love of legs, hose, and heels. She was understanding and let me buy her all kinds of lingerie, pantyhose, stockings, heels, and would wear them frequently and indulge my fetish during sex. We watched porn together and I introduced toys to our lovemaking.

Sometimes when we made love she’d whisper to me how much she would like to watch me suck another man’s cock after it slid in and out of her. We’d enact this by having me suck her juices off of a dildo. . . This is just one of our many kinky scenarios. Sadly, we divorced last year (not because of our sex life, which was great for both of us).

Realistically, Jane, how many women out there are accommodating to the leg, hose, and heel fetish? Might I ever find one who would be into making love to me while I, too, was wearing a pair of pantyhose? The latter being less important to me. Jane, understand I need and desire much more than a woman who’s into wearing high heels and hose for me. I’m not that simple. Do you think my ex-wife was a rare find?

Looking But Not Finding

Dear Looking,

I know it’s terribly difficult to find a worthy mate at all, let alone one who walks on the wild side—the same wild side—as any one of us kinksters. Still, to make a point, I want you to do a little homework for me. Go visit the largest dating web site on the Net, www.match.com. It boasts millions of men and women of all ages and types looking to hook up. Not kinky enough for you? Then go to the alternative lifestyle personals site, www.alt.com. Over a million active members are seeking a partner to play with.

Between them these sites have enough singles to populate a medium-sized state. And still you won’t find one woman seeking a man who wears pantyhose while he makes love to her. Not one! You won’t even find a woman who says she has a “thing” for men who love high heels and hose.

Does that mean that your cause is lost, you should give up and attend the next Shriners’ convention because at least there you’ll get to see some people actually different from the norm? Of course not.

It means you’re clueless to the female mindset. We don’t have fetishes the same way some men do. We actually have something even better. That is, those of us who are blessed with this think it’s better than your one-trick pony of a fetish, and we know the magic it works in sex: open-mindedness. Sadly, as with most things in life, open-mindedness is relative. A woman who seems closed may surprise you with creative antics in the bedroom if you show her you value her. Another may seem open at the outset but close up if she feels you are not addressing her needs. Make sure to find out what turns her on and not focus entirely on whether you think this one will be The One who’ll make your high heel dreams come true.

To find this special woman is to find a partner who will amaze you. She’ll take your desire to wear pantyhose to bed with her and elaborate on it, maybe cut holes in certain spots, or wiggle you into two pairs of pantyhose, or, or, or. She’ll take your tune and make a symphony out of it.

To find her, do the things in life you love to do, sweet lonely man, and ever be friendly and kind to women all around you. And when you find your dream woman, precious, give her your best self and treasure the abundance she gives back.


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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