December 2005

This Lifelong Pantyhose-Wearer is Feeling the Squeeze
Dear Jane,

I have enjoyed wearing Pantyhose since I was a child. I’m 43 now and have been divorced for 10 years. At the start of our marriage, my wife liked the idea of my wearing Pantyhose but when someone in her family discovered this about me she totally turned off and I could never wear them anymore around her.

My fiancée of 2.5 years knows I like to wear Pantyhose. At first she was thrilled with it and even bought me all kinds of Pantyhose to wear. She even let me wear her shoes and we enjoyed sex while I was dressed this way.

On our first Halloween together she asked me if I wanted to dress up as a woman. I did, and, well, I loved wearing Pantyhose in public and being all dolled up. Afterwards, I asked her to go to gay clubs with me so we could hang out as girlfriends, which we did.

I don’t want to be a woman; I just like to dress up for fun and be a lady for an evening. Unfortunately, my fiancee was jealous of how I looked; she told me I looked too good for someone who hasn’t dressed as a woman before. So after awhile she no longer wanted to go out and was also no longer open-minded about me dressing up or wearing Pantyhose, even around the house like I used to, as pajamas. (A few months ago I started to wear them again around the house and she didn’t say anything.)

We haven’t discussed anything about the Pantyhose or dressing for over a year now. How do I tell her that I want to dress up again and go out? How do I tell her I want to wear Pantyhose around the house?

P.S. I have attached a pic of me dressed up. My girl name is Iceiss because on Halloween she said I looked like the mighty Isis, the princess warrior. Please give me your expert opinion on how I look.

Dear Pantyhose Princess,

Wow, you know a guy loves his fetish when he capitalizes it as though it were a member of the family, or a pet.

Hey, princess warrior, you don’t think your relationship issues—with your ex-wife or with your current fiancée—are about pantyhose, do you? Believe me, like a pair of run stockings, your focus on pantyhose is useless; you’re on to hard-core issues—like, say, negotiating a relationship you and your partner can live with. Also, given the chilly conditions of your conjugal life at present, why would you consider marriage to someone you don’t talk about issues with for a year at a time? Believing that a legal bond will resolve anything is like believing Saddam Hussein had weapons of mass destruction.

If she’s willing, go with your lady to a therapist for a round of couple’s therapy. Take the gloves off (pantyhose, too, so you can think straight) and get honest with each other. I can understand a woman in a relationship wanting to be the pretty one; when I looked at gorgeous you in the photo you sent, I could imagine that a less-pretty-but-real woman might have a big problem going out socially with you. Besides which, she might want a boyfriend and not another girlfriend. Particularly a “girl” friend men prefer.

Of course, you don’t know for sure that this is even the core issue because you’re focused on silly power struggles like whether you get to wear pantyhose as pj’s. This is why you need to scoot your clueless butt into an open-minded therapist’s office and find out. And, for goodness’ sake, don’t get married in the meantime. For if you do, your entanglement will end up pinching far worse than a tight waistband on a pair of ill-fitting pantyhose.

Being “One of the Girls” Won’t Get Him Laid
Dear Jane,

In the last couple of years I have really gotten into exploring my feminine side. Although I am exclusively heterosexual, I usually wear panties under my conservative business suits. I have allowed the women at my nail salon to give me a makeup makeover with lipstick, foundation and eye makeup. I enjoy sleeping in a baby-doll nightie on sensuous satin sheets and I occasionally shop for women’s clothes, especially sexy low rise jeans at the local mall. I am discrete about my penchant for feminine things in order to appear “normal.”

Here is my problem: I enjoy sex with women and can’t seem to get laid. I have quite a number of beautiful female friends. I am invited to their girlie gatherings at local bars and restaurants. They seem to really enjoy my company; I am always on the A-List of those who are invited. We discuss the usual things that women talk about: their boyfriends. I am often the guy that they run to for advice and comfort when one of their macho boyfriends lies, dumps or cheats on them. I am even asked to accompany my girlfriends to weddings and out of town trips where we share a hotel room. They even casually dress and undress in front of me—but I get no action.

Apparently I have become “one of the girls,” despite the fact that I am in good shape, a successful attorney, and at least as attractive as my male competition. In a way, I’m not complaining. I love the company of beautiful women. The downside is that I am actually having less sex than when I acted like a he-man jerk.

As a woman (and a beautiful one at that) who enjoys the feminine aspects of men, can you suggest a plan to seduce one or more of these beautiful women and show her just how sexy and satisfying a feminized man can be? I will do anything short of wearing Brut stick deodorant.

In Touch With My Feminine Side

Dear Women Need to Know You Have a Dick,

Doll, you have metrosexualized your way right out of nookie. You’re right that women like men who possess some characteristics we think of as feminine such as compassion. We do not, however, like men who spend more time at nail salons than we do.

You need to relate to women as a man, not one of the girls. Being girly with women is what gay men do. What heterosexual men who get laid do is sit at the other end of the bar—alone or with guys—and send a round of drinks to the table of attractive ladies on the other side of the room.

You seem surprised that women you’re escorting to out-of-town events undress in front of you and yet show no interest in having sex with you. Believe me, honey, there is no surer sign than this that a woman does not—and never will—be interested in you sexually. A woman who’s hot for a guy is concerned about the lighting, careful about the angle at which he sees her behind, well-rehearsed in how to best drape her bathrobe for an advantageous glimpse of her breasts, aware of the condition of her pedicure, and on and on. We never, ever casually undress for a man we’re crazy for. We only do that with other women and our overweight gay male friends whom think shouldn’t cast stones.

Get out of the girls’ social group and go drinking with guys. When you talk with women, do not give sensitive counsel about how they might handle other men in their lives. Flirt with them, talk about women in your life, and make a pass. Absolutely never, ever talk about how you, too, adore shopping for sexy clothes or relate an amusing adventure you had at your hairdresser’s when your hair was being blown.

You don’t need to be a “he-man” or a jerk for women to see you as a member of the opposite sex. Once you find the special woman you’ve been waiting for, THEN share your intimate shopping and grooming habits. She might prefer you save these rituals for your erotic life together and not your everyday life, but being open about this special part of yourself could add to the fun you two will have. Just don’t use this stuff to woo women.

If you don’t heed my counsel, pretty angel, women will continue to consider you essentially dickless. And that’s a shame because you clearly have a dick that could use some TLC.

He’s Not Sure Whether He Prefers Women . . . or Trannies
Dear Jane,

Well, let me tell you that you are doing a very good job and that everybody out here loves what you are doing. My problem is this: In my past I was involved with a tranny for about a year. It started out by me wanting to try out something new and crazy. I can’t look at a normal man and say he looks good or I wanna suck his cock. but when it comes to trannys I do everything with that nice hot big hard cock.

About a year ago, the tranny and I broke up. Now I’ve got a female girlfriend who knows about my past because I was honest and stupid. Whenever we get in to verbal fights she ALWAYS tells me that I’m gay (am I?) and she always tells me to go with HIM. (Is the tranny a him?)

Am I just messed up in my thinking that just because she has nice firm tits it’s a woman when he/she is not? I’ve been with this girlfriend for about eight months now; she is 29 and I am 24. I still crave the anal sex I had with the tranny. My girlfriend and I tried out a strap-on but it just did not feel like the real thing. By the way, I do love every aspect of the female body: feet, pussy, toes, and tits. Help me, Jane.

Loves All Parts

Dear Equal-Opportunity Lover,

Where “out here” is it that “everybody” loves me, darling—Transsexual, Transylvania?

Speaking of sweet transvestites, I’m not clear whether by the term “tranny” you are referring to transvestites or pre-operative transsexuals. If taking female hormones, transsexuals would be the group to have the “firm tits” you refer to, but rarely can a transsexual who’s taking breast-inducing hormones get an erection worth writing home about. Perhaps your tranny had breast implants and is not taking hormones and so can get hard . . . And maybe I’m splitting hairs. The point is that you were with a sexual being that is, to many of us, the best of all worlds: womanly enough to be feminine and a man when it counts.

Liking TVs and/or transsexuals does not mean you’re gay, sweetheart, but does it matter if it did? You obviously like women, too . . . Maybe you’re bi. Or maybe you’re just a sexy, horny guy who wants it all. I also find TVs and pre-op transsexuals hugely sexy—some of my best friends are trannys. Does this mean I’m gay? After all, they LOOK like women . . . but I sure love that big hard cock underneath their skirts! I’m not sure it “means” anything . . . I actually would rather spend my time enjoying myself than worrying about myself.

I’m sorry your honesty came back to bite you. By letting her know you, you, in turn, learned she fights dirty. And that, in my book, is a far bigger deal than your having had a tranny as a lover.

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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