Dear Jane: Advice For Boys Who Need It Bad
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October 2005

Advice For Boys Who Need It BadHe Jerks Off in His Step-Mum’s Panties
Dear Jane,

I am 17 and recently started wearing my step-mum’s and stepsister’s panties and little skirts and suspenders. My curiosity about women’s lingerie started when I was about eight; I remember looking about my mum’s room and, when I found certain things, becoming very excited when I thought about what they were. Then I started looking in her drawer for knickers and because they were so soft, etc., I gradually started wearing them and masturbating in them.

I don’t think I can stop myself from doing what I do. I feel guilty after I’ve finished, but the thrill of wearing these things the next time I get the urge overrides my guilt and I do it again.

I masturbate while wearing their clean panties but actually prefer them worn if I can get them because of their feminine stains and smells. I have had to throw away some of their lingerie when I stain them. In fact, they recently have noticed some of their intimate stuff has disappeared. What can I do? I don’t know how to wash clothes properly and even if I did my step-mum and stepsister would see their things hanging wet and wonder about me. So that’s out. Maybe you could tell me how I can still steal their panties to jerk off in but not get caught.

Don’t Want to Get Caught

Dear Little Panty Thief,

I understand the lure of those pretty under-things . . it’s as strong as the lure of a lawn boy to a desperate housewife. Because scoring the panties itself probably contributes to the thrill, you won’t like what I’m going to say: accept that you’re a die-hard panty lover and buy your own panties and garter belts (find worn panties on the Internet). If you don’t have a job, get one or stand on a corner with a sign saying, “Will work for panties.” Point is, get self-sufficient in the world of panties. You might even find purchasing panties as thrilling as pinching them.

Is—let’s call it borrowing—lingerie a bad thing? Well, it won’t land you in San Quentin, baby boy, but you are defiling something of value to someone else . . . you’re messing around in other people’s private areas without their consent. Of course, in your case, these “other people” are your step-mum and stepsister. Which is a letter in itself.

This Bad Boy Wants to Get Caught
Dear Jane,

On the subject of male nudity in front of clothed women: I think there are two types of men when it comes to being bare-naked for your eyes. First, muscular men and strippers who are NOT embarrassed or humiliated. Second, slender, boyish, shy, submissive men, like me, who ARE!

Young, pretty women always intimidate me, even when I’m dressed. Therefore, for me to be naked before their beautiful and superior eyes and have to dance—or worse—have to play with myself . . . in my fantasies, YES! In reality? I don’t know if I could.

You see, when I was a kid, being naked outside your room or bathroom was considered dirty and shameful, even animalistic. Especially if girls saw your wiener and balls. They would giggle excitedly . . . I’d just die, red-faced.

When I was ten, 12, even 15, I would go to the park for a hike and strip naked in dense areas and walk exposed and vulnerable, playing with myself with the thrilling fear of being caught. When I did this, I was in a sexual trance. Eventually I would run in fear back to my clothes and nervously get dressed. It was a naughty, dangerous thrill for me.

Once, on a hot, sunny day in the woods, a group of girls in their late teens came awfully close to catching me walk bare-naked down a trail when I was hiking in the high grass and bushes. I heard them talking and caught a glimpse of them. They hadn’t seen me—I ran like a rabbit and got dressed, in total fear.

Now I’m 49 and these memories still excite me and I jerk off to them. What if those girls HAD caught me masturbating, in all my naked glory, on that hike in the woods? Girls can be cruel to boys. They may have confronted me, especially since I was in a disadvantaged state, bare-assed, squirming up on my toes, pulling my boner . . . giggling, whistling, embarrassing me with lewd remarks, amused by my shock and shame. They’d call me a ridiculous, perverted, wiener-milker. Would they tell on me? Make me stay and keep going? Use my act to blackmail me to return again and again so they could watch my little shows? Become their slave to orally serve them? My imagination runs wild! Am I sick?

Jane, I adore and worship pretty women and believe in female superiority, I get excited by fantasies of being of use to women and being humiliated and hurt by them, even tortured. I realize I am a submissive and a masochist around attractive women. I’ll never change. Your thoughts? Any women friends who would find me interesting?

Naked in Ohio

Dear Wiener-Milker,

I don’t think you’re terribly concerned with the “am I sick” part of your question since in the next paragraph you’re hitting on my friends . . . to go on a hike with, no doubt.

Your fantasy is not uncommon and—you’re right—you’ll never change. Nor does it appear you want to. You’re right again that it’s a fantasy of submission and, in your case, with desires to be tortured, masochism as well. You’re wrong, though, about the “type” of man who would or would not be erotically humiliated by being naked in front of pretty women.

I’ve known handsome, muscular men who crave this sort of titillation . . . teased about being vulnerably naked, or about having a small penis, etc. It’s not the nudity that’s key to this fantasy; it’s the teasing by the women. The same man who’s confident enough to appear on a beach in a string bikini would “just die,” as you say, if ordered by a group of giggling women to pull down his bikini and show them what he has.

My thoughts? Get on the Internet, look for Clothed Women, Naked Men sites and find fulfillment to your fantasy, either in person or in cyberspace. Even in Ohio there are probably women who would find it amusing to get together to tease you as you get naked and jerk off for them in a little show. Hmm . . . think of it: in two generations Girls Night Out has evolved from women getting excited over Tupperware to getting excited over humiliating men.

Women who do this might think they’re evening the score with all the men who’ve objectified women through the years. But they’re not; they’re giving you naughty little show-offs exactly the sort of humiliation that gives the extra inch to their exposed, embarrassed, and very charged dick.

He Loves Fondling Big, Sexy Breasts—His
Dear Jane,

I love your column and I love you. I’m 30 and my last girlfriend was 54 . . . I have a fetish for women’s lingerie. Not so much the fancy stuff, but the bras, panties, slips, pantyhose, that women wear every day. I especially like bras.

I love to masturbate while wearing a bra. The feeling of the soft, silky satin and lace makes me so hard. At the end of the day, I’ll put on one of my bras and some panties and stroke my hard cock while fondling myself in the bra and looking at pictures of naked women with large breasts. I imagine I’m fondling their breasts and soon I’m cumming like a fountain. I’ve been doing this since puberty and I love it. I feel so sexy wearing women’s underwear.

When I’m in a relationship with a woman I feel the uncontrollable urge to get her dirty bras and panties out of the laundry, put them on, and jerk off in them when she’s not around. Sometimes I’ll put the bra on and sniff her panties while I jerk my cock.

My last girlfriend let me do this from time to time but when we had sex she would only let me wear the panties, not the bra. I really want to find a woman who will dress me up in her underthings and have sex with me while I wear them, feeling so sexy and desirable. I want her to fondle my “breasts” and tell me how sexy I am. Am I weird to want this?

I don’t want to stop wearing bras and things. I don’t wear any of these items in public, just while I jerk off. The bras I wear are tight; I like that because when I squeeze into a 36D bra I have so much fleshy tit to caress and play with and fondle. I’ve even thought of buying some breast forms to put in my bra while I masturbate so I’ll have more breast to cup in my hand and squeeze and bounce.

I think I might like dressing completely in women’s clothes—no make-up though. I like being a man; I know I’m not gay. I just get really turned on while wearing women’s lingerie and having my titties played with in my bras. Is there something wrong with me? Should I not be doing this? How can I find a woman who will understand and join me in enjoying this fetish of mine, if that’s what it is?

Your Sexy Bra Boy

Dear 36D,

Are you weird for being turned on by what turns you on? Of course not. That’s like being weird for being 6-foot-2. It’s something you can’t help; it just is. Besides, breast fetishism is so widespread in our culture—and women are so eager to contribute by getting implants—that we don’t even regard it as a fetish.

Since you love breasts, it makes sense that you’d want to be close to them by squeezing your chest to “make” breasts out of your own flesh. What I want to know is why your lover was all right with you in panties but drew the line at bras. This I find quite strange. What’s the difference? Why such an arbitrary distinction between what’s acceptable sexual attire and what’s not? She’s already accepting one item that she perhaps finds threatening to her idea of a man; what’s the big deal if he wants a matching set?

I say, if you love it, indulge yourself. Go to the Frederick’s of Hollywood site www.fredericks.com and order the Full Breast Enhancers. At $259, they’re pricey, but they are amazingly life-like in weight and jiggle; they even warm to your body’s temperature as you wear them—and they have a sexy, squeeze-able nipple for you to play with.

To show off your pretty new bust-line, also buy yourself Frederick’s sheer bra (in white or black) and a matching panty. The breast forms look fantastically sexy in this sheer bra. Slip your pretty self into these things and I promise, Bra Boy, you’ll find yourself so scrumptious and irresistible that you won’t leave home for at least a day.

As for finding a partner to play with: As I’ve said a jillion times, sweet baby, find a woman you like and really connect with outside of your sexual desires. You have your best shot at really good, kinky sex when 1) you yourself accept your own desires and 2) you have a relationship of trust and caring with a woman you like.

In the meantime, enjoy your sexy breasts and turn yourself inside out with orgasms inspired by your sexy bras and pinchable titties.

No Bulge for This Boy, But Is It Safe?
Dear Jane,

I have adored pantyhose for many years. After I pull on my pantyhose, I tuck my penis between my legs and put on a tight girdle to keep it there. I love the tightness and I adore the total female look—no bulges. But I find even the simple act of walking with my penis tucked down there crazy-sexy. It’s the stimulation of movement and the tightness and the gusset of the pantyhose stimulating me with every step that makes me orgasm beyond mind-blowing. Will this cause any damage to me?

Tight Kevin

Dear Tight,

Only if you smoke or do drugs at the same time.

Seriously, kinky Kevin, if you pull your penis down between your legs and force it to stay there for hours on end by using the vice of a girdle, you could restrict blood flow. At the very least, restricting blood flow inhibits your erection.

However, I’m not worried about you. You’re so excited by the stimulation of your pantyhose, heightened by the tightness of your girdle, that you feel an almost immediate need to release. Which saves your poor cock from death-by-squishing. I’m assuming, of course, that, if you’re having your little accident there inside the confines of your pantyhose and girdle, you allow your friend to come out and catch his breath afterward. If not, I would recommend it. We need to take good care of our playthings or they won’t work for very long.


Jane Vargas holds a Ph.D. in Human Sexuality 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@xtrattalk.com or writing to her at Leg Show. “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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