November 13, 2001

Dear Jane,
I find myself in a peculiar situation that in one respect could be the answer to my dreams, but also potentially harmful. A year ago I interviewed a forty-year-old married women for office help in my business. Kim is well mannered, very pretty with dark hair and a lovely figure. Because she was very familiar with our accounting system, and had a nice disposition, I hired her.

At a recent office party, Kim ditched her husband as she cornered me and began to freely talk about sex. She then admitted to me that she liked the days that I wore my Polo jeans to work, saying, “I love a guy’s butt when it’s high and tight.” Since that party she has elaborated on everything from enjoying porn movies to making her own fem-dom themed videos with her husband. Best of all (from my point of view), she says she’s dying to “spank the boss.” I haven’t told Kim that she’s pushing all of my buttons; in fact, I give her the brush-off, although admittedly half-heartedly. Truth is, I want to tell Kim all of my secrets—and I would, if she were single and not working in my office.

Is it wise, Jane, to allow Kim to fan the flames of desire with all this teasing sex talk? It would be the first time my fantasies have been played out—actually, a dream come true. On the other hand, she is married and an affair could ruin both her marriage and things in the office.

Morally Challenged in Boston

Dear Challenged
Oooh, how I feel for you, dear boy. An attractive, playful, bewitching soul who adores a high, tight butt and would love nothing more than to spank the boss’s decidedly naughty behind. You say she doesn’t know how much her talk turns you on, but of course she truly does, clueless boy. This woman is quite aware of her power over you; trust me on this. As tempting as “well-mannered” and nicely disposed Kim might be, she’s trouble. Take the flattery and run. Better yet, help her find another job. We cannot toss decency and decorum to the wind just because it’s difficult to find a partner to play out our fetish fantasies. Be happy to know there are actual women out there in the world who share your particular fantasies. Anyway, Kim has far too much bravado. A truly sexual woman sends her signals quietly; she doesn’t brag about making videos with her husband. My money’s on Kim being a dud in the bedroom but a star witness in a legal action against you. Zip up your Polos, bad boy, and take your cute butt elsewhere.

Dear Jane,
Ever since my early teens I’ve occasionally bound my genitals. I usually do this by pushing my testicles up into my body and then pulling my organ way back between my legs and securing it with several layers of an elastic bandage. Sometimes I put on panties to increase the humiliation and sense of emasculation, and I imagine a woman forcing me to do all of this. I have worried a lot about this and I have some questions that I thought you might know the answers to, considering your expertise: Can this cause any long-term damage to my testicles or my wiener? Will it cause permanent stretching that would make things sag? Can this cause impotence? Also I wondered if you know of a way to make my wiener stay back without using the bandage (it looks bad)? These aren’t the kind of questions I can ask my doctor. Please let me know if you have any information or instructions to give me. Someday I’ll get up the nerve to order a pair of your worn panties.

Thank you,
Kevin

Dear Kevin,
First the bad news, sweet boy. Your play could be hazardous to your cock’s health. I contacted the knowledgeable folks at www.sfsi.org (also 415-989-7374) for some help in answering your questions (for questions on any aspect of sexuality, one can contact them for free, accurate, and nonjudgmental information). What you’re doing is called “testicular tortion,” and, unfortunately, the more severe the action, the more the damage. Yes, you can cause permanent stretching and sagging. You can cause bruising. You can rupture blood vessels. You probably won’t become impotent, but by tucking your testicles up close to your body, you are in danger of reducing sperm count and possibly becoming sterile. If you get carried away, you can even cause something called “testicular necrosis,” and I think we both can guess what that is. If you continue this form of bondage, try not to stay bound longer than 15 or 20 minutes; blood flow needs to occur to keep yourself randy. Now the good news, dear Kevin, and I know you could use some right about now. I have two suggestions. Yours happens to be one of my favorite forms of play. Instead of tight and unattractive elastic bandages, tuck your willful cock back between your legs and slip on a stretchy, too-small pair of panties. It’s the bulge there in the panties that is so very erotic and it is the bulge that reminds you that, no matter how much you try to pretend you’re something else, you’re just a horny boy in girls’ panties trying to hide his willful cocklet. If you’re committed to the bondage aspect of your play, get a gaffe (a device used by TVs to hide their cocks). A site called www.thefantasygirl.com has some good choices. One even has a pocket for your cock and a nice, feminine bush. Now, that’s sexy. And you’ll have a healthy cock to play with for a long time to cum.

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