Dear Jane: Advice For Boys Who Need It Bad
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March 2006

Advice For Boys Who Need It BadDarlings,

The letter below is one I received by e-mail. Like many letters, this one piqued me in its intense fusion of bewilderment, desperation, need for assurance, and eroticism. Also, like almost everyone who writes me, this gentle soul is both imprisoned and unleashed by his sexual desires.

When I first heard from “Wet Blonde Pussy,” it wasn’t the question you see below, but rather a quick e-mail with a sort of desperate cry: “I can’t stop wearing panties.” Between the lines I recognized the familiar questions born of guilt and shame: “Is what I do normal? Am I normal?” (Such letters usually arrive after their writers have masturbated to conclusion; never are they written in the heat of excitement.) I wrote this young pup back asking for more information . . . his history with his obsession, how he currently satisfies himself, his feelings about his panty penchant, and so on.

Thus began a correspondence between us that occurred in real time, almost as though we were talking on the phone for two hours instead of burning up our keyboards. The resulting letter is a blending of his words to me, excluding information he asked me not to publish. It wouldn’t be fair to present myself as only an impartial party dispensing wisdom gleaned through education and experience. In fact, I was taken with this shy guy. I found him sweet and sexy. He turned me on, although I wonder whether he had the sexual confidence or sophistication to realize that. He is, after all, just 24 and barely out of his lingerie closet.

Confirmed repeatedly in letters I receive is that sexuality is a hot spot unlike any other in our lives. Nothing causes as much self-doubt as who we think we are (or might be) in the private recesses of our sexuality. It’s no wonder we doubt ourselves. . . Sex for pleasure has been considered sinful off and on (more on than off) since Biblical times. Indeed, we have barely recovered from the masturbation-causes-insanity Victorian mindset, but at least boys are no longer sent to bed clamped into penis cages. Imagine if, instead, the Kama Sutra, a how-to manual of the erotic arts of the Hindus, had taken root? What if John Ashcroft was concerned not with covering nude statues but commissioning more of them? We’d live in a Kama Sutra world in which sexuality was an art form, a discipline to be mastered. Where sexuality was deemed not only worthy of respect but divinely inspired. If that world existed, Wet Blonde Pussy would be writing me not to express doubt about himself, but to boast of his sexual creativity.

With that, I give you . . .

Driven to Distraction by His Holey Panties
Dear Jane,

I can’t stop wearing panties around the house. I think I’m different from other men who write you about this; for me, it’s not an option anymore. I feel as if a part of me has changed permanently. I cannot go a day without wearing a silk thong or g-string. I even threw away all of my boxers and briefs. That was freedom!! Should have done it long ago. Now when I leave the house, I wear no underwear at all. But at home . . .

I don’t know what it is but I just feel “right” when I dress in my sexy panties, and yet the other half of me always thinks I’m crazy when I do because most of the time I am very much a man. Do you think all of this could be caused by not having a girlfriend for a very long period of time? I have been rejected by a lot of women in my life. Women don’t understand me. They rarely return my phone calls. I sure can’t tell them about my fetishes.

I’m 24 years old. I had wanted to wear panties even when I was a boy, but didn’t buy my first pair until I was 19. Before that, even when I was a kid, I cut my underwear into a thong panty shape; I hid them in my room.

I’ll never forget when I bought my first lace thong. It was a snug size 5. Two women were in the store when I bought it. They could see that my face was red, and they both gave me a wicked smile, like they knew the thong was for me. I will never forget going home and ripping my clothes off. I shaved my pubic hair and hair on my butt cheeks clean off. I took a shower and cleaned the panties before wearing them. Oh I will never forget putting on that thong. It was one of my greatest experiences.

For some reason I have developed little B-cup breasts. Weird, but they are actually kind of perky. Too many hormones from milk, I guess (I drink a lot of milk). It is kind of embarrassing sometimes, but when I’m at home I love to pull on my nipples, I love to squeeze them a lot. I was even thinking of getting a breast pump, or some nipple clamps.

Excuse me, Jane, I’m going to change into my best pink silk thong while I finish writing to you. . . .

My little clit is popping out of my panties, it hurts so bad, I think I need to stroke it to make it feel better. But I won’t yet. Did I tell you I cut a hole in every thong I buy? So that my pussy-cock can stick out and bob around . . turns me on. But right now I’m not bobbing; I’m very, very stiff. When I look down I see my smooth, hard cock surrounded by the pink silk. I want to grip it and make myself feel better. But I won’t, yet. Both hands on the keyboard . . .

You are the first woman I’ve talked to about all this. Would you go out with me, Jane? I need you to turn me into your little girl. I can imagine getting a spanking from you. I have been a very naughty little girl; I should be punished for wanting to stroke my cock as it stands straight out through the hole in my silk panties; you would consider the sight of it offensive and obscene. And my balls—do you want them hidden away inside my thong, or hanging free so that you can spank them as well? Jane, is it wrong to adore myself in these pink panties.

You would like my pretty body . . . I always make sure my body is clean shaven, I would like to get all of my pubic hair, except for a landing strip, permanently removed.

Today I went to the lingerie shop around the corner from where I live. I am now a regular there, and they know the panties I buy are for me. It was quite embarrassing at first but I think a couple of the girls there are open to me. I think I’m finally open with myself. I love the thought that the women know I wear the thong panties that I buy from their shop. I even used their dressing room a while back.

I am thinking about going to the pool in a white thong panty, just to see what it’s like. Do you think that is ok?

I have always wanted a mistress to tell me what to do. I am looking for a girlfriend who will dominate me. Do you have any advice about where I could go to meet a dominant woman? My ex-girlfriend was going to dress me up to be her little girl, but we didn’t get a chance to do that. I was very disappointed.

Do you wear thong panties? I don’t know how you women take it, but that silk thong riding up my sexy butt cheeks is such a thrill. Do you think it’s okay that I want to wear this stuff?

I have had girls tell me that they can tell that I don’t wear underwear. Should I wear my panties instead? Can you tell if a man is wearing panties, by his clothes?

I’m not touching it at all. It hurts so bad holding back. Can I give myself a spanking before I jerk off?

I don’t think I’m gay, but I have lodged a vibrator inside a very tight thong, and I got off huge. I guess I’ve always imagined a women strapping on a small, thin vibrator and then doing me. That doesn’t mean I’m gay does it? I am not attracted to men at all, nor would I ever have sex with a man. I sometimes do wish I were a lesbian though. My favorite erotica is about two women together, either bisexual women or lesbians. The idea of strap-on sex is a total turn-on. I would go on my back for you, Jane. I would spread my knees wide, and hold myself open for you to fill me. I love you women so much. I just haven’t been with a woman sexually for a long time. I guess it’s because I’m too submissive, passive, and shy and I get turned on by seeing my hard pussy-cock stick out of my thong panties—what woman would find that sexy?

I’m thankful I can be my natural sexual self with you, Jane, with nothing held back and be accepted just the way I am. One last request, please . . . Would you take me to the pool, please? If you like, I’ll wear a pussy pink thong-bikini of your choice...I’ll put my hard pussy in a cock ring, if you want it to bulge out, or even wear a thong with an anal ring built in, if that’s what it takes for you to go to the pool with me, and if we go at night. Or, in the daytime, maybe I could wear the white thong panties I mentioned earlier. Maybe you’d tell me to get into the pool and get my already-sheer white panties wet . . . Would you? I need to sign off . . . I’m going to stroke my pussy cock for you now . . .Please, Jane, what’s wrong with me?

Wet Blonde Pussy

Darling Puss in Panties,

You, my precious, are your own best lover. You’ve tapped so much into the female aspect of yourself that, in your sex, you hardly need a woman at all. Which is great when you’re bobbing in your thong. But less great when what you crave is an emotional connection with a partner.

You ask whether I think it’s okay to adore yourself as you lounge around your home in holey panties. Well, you’re asking Dear Jane, not Dear Abby, and, of course, I find masturbatory self-pleasure acceptable in all its creative forms. (Actually, to her credit, I bet Dear Abby does, too.)

You also wonder whether your private activities are a result of having so few private activities with women. No. Even if you had been the most popular boy in elementary school, you still would have been cutting thongs out of your tighty whities after school. You appear to be submissive by nature, Puss, but some of your submission is the result of having had less luck with women than you’d like; wanting a dominant woman to take you by the hand would make everything so much easier, wouldn’t it? Too bad the world isn’t so simple. You’re going to actually have to put yourself out in the world, doll, to find a mate, as well as a playmate (how convenient it would be if you could get both in the same woman).

I’ve said it here before, sweet angel: men wanting and craving to be penetrated anally is not “gay.” Due to the many nerve endings and the love the prostate has for massage, it’s oh so very nice to have one’s back orifice filled. In the case of a submissive guy like you, there’s also the added thrill of being “taken.”

You say women tell you they notice when you go out commando; you wonder whether wearing panties would also be noticed beneath your trousers. Well, duh, darling . . . With your precious penis wagging through its porthole in your panties, you might want to check the mirror before you parading out and about.

Unless, of course, you’re an exhibitionist. Which, given your sheer-white-thong pool invitation, you may be. I appreciate that you’d like the world to adore your pretty self as much as you do, angel. However, the world has not consented to the viewing, and so I encourage you to think hard about taking said swim. Unless, of course, you take a dip in a private pool . . . in which case, I encourage you to dress as provocatively as you can stand. Aahh, sweet Puss, I thank you for the tempting invitation.


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@xtratalk.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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