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

Dear JaneMistress Jane,

I thoroughly enjoy your column, Leg Show, and X-traodinary Talk! You’re my fairy godmother: intelligent, sensual, and understanding. And I have a question for you.

I have a teenie weenie peenie (cocklet, cockette, or clit). To contextualize for you . .my itty bitty clitty measures between 3.5 and 4 inches erect and lacks girth. While most men are afraid that they don’t measure up, I am greatly turned on when teased about not being able to satisfy a lusty woman due to my lack of “stature.” I first noticed that I was small down there when I “hit the showers” in high school with the other guys after playing football and basketball. The fact that I have this particular fondness is made all the more humorous by the fact that I hold an important position at a worldwide firm and am six feet tall and weigh 235 (mostly muscle).

I have fantasies of being a pantied, cuckolded sissy slave serving in role of French maid or servant, while the “Lady of the House” is being satisfied by a true stud or the Lady demonstrating what a real cock is with a gigantic strap-on. What is especially thrilling to me is the teasing and erotic humiliation of this fantasy.

I have recently begun dating someone. She is an assertive and intelligent lawyer. Recently, we were watching a basketball game with some of her friends. I left the room to get more beer. From the kitchen, I overheard the ladies talking crudely about how well hung a certain seven-foot, 300-pound Laker basketball player must be. I peered through the kitchen and I saw the ladies demonstrating how wide they thought their mouths would have to be opened to be able to perform fellatio on the basketball player. They continued to talk about how they wouldn’t be able to walk for days after an assault from such a stud.

Lastly, each of the ladies took to asking each other whether their significant other had such equipment. I heard responses such as “Joe is not that big” or “Not that big.” My lady answered an emphatic “No way, but he’s my stud . . .” I was positively aroused by that.

The conversation stopped when I re-entered the room. I had a positively raging hard-on (by my standards; one of the benefits of a teenie-peenie is that it is easy to camouflage). I fantasized about being made to prance into the room in panties and pulling my panties down to reveal my shame. (This fantasy caused me to excuse myself to the bathroom to take matters into my own hands.) I have not introduced her to my fetish, but would love to. I would love your insight into why I am aroused by my small-cock teasing?

Sammy

Dear Sammy,

You’ve heard the one about the man who has a small penis, haven’t you, Sammy? When he placed his cock in her hand during their first intimate encounter in the dark, his girlfriend said, “Thanks for offering, but I don’t smoke.”

Why the turn-on? It may or may not have begun as a response to having been teased about your cock as a youngster. It could, in fact, be a subconscious means to get what you want . . . to play the submissive role as well as to express your female-maid fantasies. Behind both of these is your fundamental drive to be submissive. What stands in your way of this is your maleness; the cock is the universal symbol of power. The more you can enter your fantasy, playing the role of a submissive—indeed, a submissive woman—the better. What better way to do this than to be a man of small cock.

Also, a small cock gets you off the hook for having to perform in the bedroom. Even before you get naked the first time with a woman, you know that your teenie-peenie can’t possibly satisfy. The recent scenario you recount about the basketball players suggests that you feel absolved of having to perform adequately from the get-go. Since you can’t possibly be a “real stud,” you may as well get into a maid’s outfit and be teased—right, little one?

Also, having this complex of a diminutive cock could be a device for getting attention from women. Just as a football player gets sexual attention for being a large man, you get the attention you crave from being a tiny one.

To sum it up: You want to be submissive, to get attention, and to be freed from the anxiety to perform. In just four inches, you accomplish all of this! What a wonderful world!

Understanding what brought this about is less important than accepting the joy it gives you. You are clearly in the enjoyment mode; it’s clear you celebrate your passion. I personally find it erotic to tease a man who wants to believe he’s small; to do so provides an immediate and effective vehicle to take a lover to that glorious submissive place. Sexuality is about enjoyment, after all. . . We are wonderfully weird and complex creatures.

I do need to mention one thing, though, dear Sammy. Not to burst your fantasy bubble or anything, but you may not be as small as you think (and hope) you are . . . . Cocks that are fairly large in the flaccid state may not differ that much, upon erection, from small flaccid cocks. In high school you compared yourself with limp dicks, hardly a scientific measure. In addition, self-measurement of cocks is notoriously unreliable; you could be shorting yourself on the goods you really do have. Finally, cocks appear smaller when a man carries extra weight. I’m sure you’re right, precious, that your 235 pounds is “mostly muscles,” but some of that “muscle” may be encroaching on some of the real estate that is rightfully your cock’s. Your precious penis could take on new heights with the loss of a few pounds. Not that you want that . . . In fact, I can hear you right now ordering donuts up to your office.

Hi, Jane,

I am a 31-year-old single male who has finally decided to come to terms with some questions about my sexual orientation. I have always dated women and enjoyed sex with them. I like the smell, hairless body, smooth skin, breasts, and a flat stomach. I can really only become aroused by a very attractive woman. On a scale of 1 to 10, they need to be at least a 7.

On the other hand, I am very attracted to transsexuals who look extremely passable. However, on a scale, I would be more aroused by a less-attractive TS than I would be a less-attractive woman. I have been with a few transsexuals, and when I relax and get past the guilt I have enjoyed it more than my sexual encounters with women. My very best sexual partner was a TS; a very attractive girl was a close second.

I have only engaged in the TS thing over the last four years. I didn’t even know they existed before that. I had always been curious about other men’s cocks, but never did more than some phone sex, fantasy, and masturbation thinking about them.

A real turn-on has been hearing my girlfriends’ experiences, in detail, about their time spent with other guys. I am always very interested in hearing about the past boyfriends’ cocks. I do like to suck cock, I really do. I feel like I am worshipping the cock and feel very submissive; I am normally very aggressive and in control in life in general. I don’t really like anything else about a man other than his cock. I mainly just want to suck it, and rub mine against his. I could only be turned on by a hairless, thin, ripped-stomach guy. A big dick would be a big plus. I have also always dreamed of a threesome with a girl and a guy.

So that is basically my sexual dilemma. I want to be married and have a family some day, but before I do, I want to come to terms with these desires. I am afraid if I don’t understand them, that I will always have question marks.

Can I live in a totally “het” sexual relationship without repressing my other desires? Am I normal? The more I let go, the more I realize I enjoy dick more than I thought and pussy less. Lastly, am I just kidding myself, because I like cock so much, that I’ll be able to limit myself to women? Am I bisexual or gay because I like cock even though I am not attracted to 90 percent of all men? How can I love women, but also love dick? I just wonder if these are all signs of someone being gay, but repressing it. Please help me, Jane!

Steel

Dear Steel,

Think about sexual identity as existing along a spectrum, from “completely straight” at one end, to “completely homosexual” at the end. Most of us fall somewhere along this spectrum; very few of us lie at one end or the other. Also remember that sexuality is fluid; our tastes and even orientation can vary over time. You might prefer women at some points in your life and men other times.

You ask if I think you are normal. I think that all consensual sex is “normal” . . . if “normal” even exists. I am learning that everyone has his or her own particular take on sexuality and that even Jesse Helms wouldn’t be able to adequately define the term. I also believe all fantasies are normal. They’re just fodder for the mind, that great sex organ between our ears.

But, in the end, it really doesn’t matter whether I think you’re normal, Steel—or what society thinks. The real question is how you feel about yourself and whether your fantasies and (consensual) behavior are a problem for you. Take playing the role of a heterosexual lover when you don’t honestly feel that way. Society may look from the outside and see “normalcy.” But if it’s causing you a lot of pain, for you, it’s not at all normal.

Accept yourself despite what others may think of your fantasies or behavior. I heard sex therapist and author Marty Klein speak recently and he talked about the need for self-acceptance when we’re feeling the worst about ourselves, not the best. You want to grow to the point, he said, where you’re empowered to run your own life, sexually and otherwise. Ultimately, he said, good sex stems from self-acceptance, not genital function or “normality.”

Your transsexual lovers offer a bit of both ends of the spectrum, don’t they . . . You say you’re “not attracted to 90 percent of all men,” but it sounds as though you’re likewise not attracted to about 90 percent of all women, either. You also say you’ve only experimented with TS’s for the past four years, but you’ve only known about the existence of these sublime chicks-with-dicks for that long; you didn’t waste any time seeking them out, did you? You also clearly have a great passion for cock. So, to me, dear one, your letter suggests that at this time in your life you want to explore the more-gay end of the spectrum. So what? Perhaps you’re gay, Steel. Perhaps you’re bisexual. Perhaps you’re straight. Perhaps more experimentation is in order. Lucky you.

Dear Jane,

From one lingerie lover to another, does wearing a special bra or panty, say, from Lise Charmel, feel different than wearing one from Victoria’s Secret? Or does all pretty, frothy, delicate lingerie have the same power in the way one feels?

I have a girlfriend who refuses to wear lingerie any longer because her husband enjoys her the most when she’s all draped in sexy stocking and garters and slips, the whole shebang. But she feels that he’s only becoming aroused from the lingerie and not from her and so she stopped wearing it totally. Can you imagine?! I was astounded when she told me this.

Does one ever tire of wearing lingerie? I hope not! Thanks . . . and have a lingerie-lounging kind of evening,

E

Dear E,

You don’t say whether you’re male or female, but what does that matter when speaking of one of the private delights of this world. First, with regard to your misguided friend . . . . Tsk. Tsk. Really now. She’s worried it’s the lingerie and not her that is her husband’s turn-on? If there were no lingerie involved and she felt her husband was aroused only by the act of sex, would she withhold that, too, because, in her soured little mind, it was the sex he loved, not her? I hope she comes to understand that lingerie is just part of a package, a prop, all part of foreplay. He probably adores “opening the package” as well as the tease that lingerie provides. If she thought more broadly about what this frothy (great word, E.) stuff symbolizes, she’d understand the power it gives her in her sexual dynamic with her husband. Wearing it, and teasing her husband with it, she’s saying, “You can have me, but only a little bit at a time.” Poor wifey; she’s cheating not only her hubby, but herself, of mutually shared pleasure.

As far as the good stuff and the really good stuff goes . . . Well, I must confess to preferring the latter. Why? Eighty-five dollar panties do the same job as $10 tighty whities. But the sublime little nothings that I put on every morning—my favorites are Lise Charmel, Aubaude, and Chantal Thomas (from France), La Perla (Italy), and Agent Provocateur (England)—creates a subtext in my life that reminds me that the sheer act of living—with all its hidden unknowns and adventures about to occur—is a sensual experience. Life, wouldn’t you agree, is about style at least as much as about function. Ultimately, exquisite lingerie, to me, is like fine chocolate. I’ll eat a Hershey’s kiss without grumbling too much. But give me a creamy Swiss dark chocolate and I’m halfway to heaven. And, my friends, the panty gods know that a new Lise Charmel garter belt does far more than any chocolate could ever aspire to . . . .


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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