Dear Jane: Advice For Boys Who Need It Bad
Deflowered in Vegas
Dear Jane,
I'm Ted and I wrote you about being 35 and still a virgin. I wanted to report to you on my Vegas vacation where I hired an escort.
First, let me say I had sticker shock at the cost. The ad said the escort would cost $250. When I called to confirm my appointment, I asked about tipping the girl. The response: That's up to the girl so I'm thinking $100-$150. As the escort said to me, "Honey, you don't know anything about this business, do you?" She said the $250 was all agency money and that she didn't see any of it. Her fee was $400 for a strip show, massage, and playing with herself. Anything else was extra. So it came out to be an additional $600 for what I asked (I wanted to learn how to give a good massage, work a woman's breast, and give good oral sex).
The thing is this woman gave me such a high school day's erection and I wanted her so much that I would have paid anything. It was worth it. First she explained the techniques of what to do, then she'd perform it on me (god, she sucked my nipple to the point I was moaning). Then she'd have me do it to her. All the while she would talk me through it. She was literally the hooker with the heart of gold.
As I mentioned, she gave me an erection the likes of which I haven't felt in years. She was a solid gal with three kids; she seemed almost the mother next door you always wanted to fuck.
She also took me in her arms and held me as I suckled her breast. I never felt so happy and safe. I'm sure there's a psychological term for that pleasure . . . but I don't care what it is because that was a feeling I'd been without forever and had been looking for all my life.
She was good at communicating if I was doing something wrong or right. I finally got to taste a woman, although it was through a condom spread over her pussy. I took to it like the finest taste I ever had in my mouth. I sucked, caressed, and tongue-fucked that pussy with pure passion. By the end my tongue was sore from keeping it hard while I was down there and I loved every minute of it.
Another positive of the experience was that I was erect the whole time—over 30 minutes. Even when she performed oral on me, I didn't lose my load for at least a few minutes. Remember how worried I was about staying hard or cumming too fast? Well, I answered my question about those things . . .
Aside from the part of paying so much, the only bad part was two phone calls that interrupted our session; they were from the agency checking on her. Also, as soon as we were finished, she was out the door. She did give me her personal page and cell phone numbers to use the next time so I could skip the agency fee.
After she had gone, I laid there a few minutes, thought about the whole thing, grabbed a shower, and went to the bar for a drink and more reflection.
It was an intense session, Jane, but ultimately sort of hollow, since when business was done she was out the door, probably for another appointment. I think that since I've gotten my confidence I won't need this type of session, but will try one of the mistresses sometime to see if they can help me with a fantasy (or three) when I'm ready.
Your Faithful & Devoted Non-Virgin,
Ted
Hi Ted,
Clearly, you were screwed more way than one, sweet baby. I am appalled that you had to spend $850 for 30 minutes of deflowering—with interruptions yet! But, like real estate in San Francisco, there's no price too high for bliss; the sexual confidence you gleaned from your heart-of-gold girl was worth every penny.
Now it's time to start connecting with "real" women. The happiness and safety you felt in your Las Vegas lady's arms is nothing compared with the feelings you will have in the arms of a woman who truly loves you.
Did He Go Bad Because She X-Dressed Him?
Dear Jane,
I am a 45-year-old woman and up until now have always loved sex and fantasy. I am struggling to understand my ex-boyfriend of four years . . . I loved him dearly but ultimately I could not satisfy his needs in regard to his sex addiction or whatever it is that he has.
When I met my ex he was two years out of a failed marriage in which he was still very bitter as he claimed that she had cheated on him with another man. I felt so sorry for his pain.
Shortly after we began our relationship he shyly confessed that he liked to x-dress and had been doing it since he was a young boy. I did not have a problem with his desires. I encouraged him to dress up with me. We would go shopping together for lingerie and I bought him stick-on nails and make-up. I even occasionally used a strap-on to please him.
After a year of dating we moved in together. He then confided in me that he had actually cheated on his wife, not the other way around. He said that he had several hotel rendezvous with men he had sourced out on the Internet who wanted to have sex with a x-dresser. I was gob smacked. His excuse for betraying his wife was that she had completely turned off sex and that he just was so horny he had to get sex this way. From that point in our relationship everything spiraled downhill.
He started pestering me to invite strange men off the net to have sex with me in front of him so he could watch me getting it "over and over," as he put it.
I didn't want to enact this fantasy . . . now I blame myself for not satisfying him. I mistakenly thought that I could satisfy him with a little spoken and role-play fantasy (like I've seen you suggest to others) sex talk, dress-up, etc. But he made it patently clear that this wasn't enough. He started telling me I was boring, sexless, and inhibited.
Of course, that's just what I became: boring, sexless, and inhibited. I started putting on weight. I was getting paranoid of having oral sex with him and wanted to use condoms for protection. I used to love kissing and sucking him—I loved his penis—but now he was saying that if I didn't swallow I was no good and if I didn't let him have anal sex I was no good.
He said that if I dressed up more like a tarty slut then he wouldn't have to dress up. He told me if I didn't want to let a fit young guy have sex with me then I was just too boring for him.
I still don't understand what happened to him. Did I do something wrong by allowing him to verbalize his fantasies? Did I inflame him by accepting and helping him in his x-dressing? In a way, I wonder if I had a hand in creating this demanding, insatiable man . . . And why was he so adamant that I had to do the other-man thing in order for him to be satisfied? Why wasn't fantasy in this department enough for him?
My torment has been exacerbated by my foolish sentimental visit to his website only to discover that he had taken a beautiful woman on a South Pacific cruise. They looked so in love it made me want to vomit.
What amazed me was that in his website photo his legs were completely hairy. Is it possible that he has decided to not x-dress anymore? Is it possible this woman is not going to have to endure the abuse that I did? What did I do wrong? Am I just a boring prude or was I out of my depth? Please help me to understand what I was dealing with here and how I should have protected myself better emotionally.
Perhaps I am just too naive. I am so shell shocked from all this I have not been able to date another man let alone have sex—which I used to love so much. Jane, you are "the antenna that receives the music" only my music is a bit melancholic these days. I am determined to recover, though; my motto is the old Chinese proverb: "Fall down seven times, get up eight."
Miss UK
Dear Miss Treated,
Such a big long letter and not a peep about the mind-blowing sex he gave you, the creative ways he fulfilled your fantasies, the understanding and love he heaped on you when you disclosed your secrets. Heavens, child, you were more likely to get an STD than anything worth having. Hmmm . . . if only we women could tell true love from false love as we can tell mushrooms from toadstools.
Your only fault in this relationship is that you were all grown up and allowed a little boy to call the shots. Your relationship ended not because you were too "boring and inhibited" to have sex with strange men while he watched; it ended because he was unable and unwilling to show up as a mate to you. And, frankly, a man who doesn't show up doesn't measure up.
A man who measures up is one who takes responsibility for his actions and respects his partner's limits. Your Don Juan claimed that if you dressed more as a tart then he "wouldn't have to." You should have seen that one coming when he told you that he "had" to meet men in hotels for sex while cross-dressed because his wife wasn't interested. This guy's playing a child's game, sweetheart.
There's nothing wrong with his desire to watch while you have sex with other men. Likewise, there's nothing wrong in your not wanting to. What's wrong is his verbal abuse when you declined. What's also wrong is his insistence that it's everybody else's fault when he doesn't get his way.
If he only knew how many men would give their right testicle to simply be able to TELL the woman in their lives their true fantasies. Your man not only could tell you his every fantasy, he could count on you to cherish him no matter what they were—and even to provide what you could to attempt satisfaction.
Instead of treasuring you for all you gave emotionally and sexually, he was the bratty 2-year-old crying, "It's not enough." And—believe me—if you had had sex with strange men to satisfy him, it wouldn't have been enough. Spoiled children never feel they get enough. You no longer have your Lothario, but at least you have your self-respect.
You ask whether you unleashed his ever-changing sexual appetite by encouraging his cross-dressing. No, you didn't. It's not cross-dressing—or your doing it with him—that made him a horse's ass; he just is one. Plus, hairy legs or not in the photo, he will never give up his desires to cross-dress; it's not his choice to do so; it's as much a part of him as the penis you loved to tuck inside his frilly panties.
Who said that love is the sweetest joy and wildest woe? Forgive yourself for loving a man who is not mate material. And know that it's the most damaged who inflict pain on others, sweetheart.
I predict that your story will have a happy ending. And it will be with a man who'll be grateful to be with a woman who's all the passionate woman you are. One who will treasure you . . . because, next time, darling, having healed from this one, I do hope you won't have it any other way.
Older Women Float This Boy's Boat
Dear Jane,
I'm 23 and am attracted only to older women; I have been with older women and those experiences were the most fulfilling in my life; they could never be repeated or imitated. I have been worried that I wasn't attracted to young blonde playthings—aren't all hot-blooded men supposed to be? For me, nothing could be more of a turn-off.
My first encounter was when I was much younger and a paperboy in the neighborhood. She was pretty, 35-40, had long brown hair with a clip or small bow in it. I arrived at her house at 3 each afternoon with her paper; as I approached her steps, she could see me from her living room.
One day I walked up the steps as usual but noticed she was wearing a nightgown. I was excited (but confused) about the feelings I was having. Like I shouldn't be getting horny over her. I felt wrong or bad. I quickly left the paper on the step but that night I masturbated furiously over her, thinking of her inviting me inside, teasing me with her walk and her nightgown, telling me I was a very good paperboy, and that she liked me. Her teasing me with her words was what really got me excited.
The next week, she waved and smiled when she saw me coming up the steps. This time, her hair was pinned up in a very nice way, but what I really noticed was what she was wearing. Under her housecoat she had on stockings with little fasteners at the top, a very short lingerie babydoll gown. I could see her breasts were pushed forward.
I had an erection immediately. She came to the door; I was terrified. I did not want to be there, but she looked so pretty. She opened the door and invited me in. She gave me a reassuring smile the entire time. I felt so at ease; I even wondered if I loved her?!
She sat me down and there was this strange exchange going on . . . now as an adult I understand it better. Without saying anything she was saying, "I know you notice me, I know you like me, I know you are excited, I know you don't know what to do." She was so sure of everything.
I couldn't help myself. I blurted out, "I like you." She placed my hands on her waist. I could feel her panties underneath; her breasts were right in front of me. I felt like I was going to ejaculate just from this. I sort of grabbed her breasts, not realizing how soft they'd be. She said that it was okay. She let me explore; I know my motions were too quick.
She asked me if I was okay with everything. I said yes. She reached over and rubbed the outside of my jeans and pulled down the zipper. I let her release me and she started to stroke me. It was all too much as I started to feel my orgasm building. I motioned to lay on top of her, trying to push myself into her groin. How did I know what I was doing? She said I could rub against her and cum on her panties so I started to do this; she let me in between her legs (I'll never forget this) and I came almost immediately onto her panties. The whole time she patted my back and told me she was excited, too. She smiled and said that was great and that she really liked me. She helped me clean up and get dressed. I left the house within 30 minutes of getting there.
Nothing ever happened again, but she made me feel so good, talking to me with a warm, friendly way, like I'd been her adult lover. Four months later, she and her husband moved away.
The next encounter was when I was 20; I as at a friend's mom's house and she was supposed to help me with my tax forms. She was probably 42-45, black hair, and slim. When I got there, she changed into something "more casual," and when she came back she had on a tiny little blouse and tight short-shorts. I was hard right away.
Well, nothing happened, but she sure enjoyed teasing me. I could smell her perfume, could see the outline of her panties. She would bend over and push up against me. I wasn't sure if I should reach out and touch; she seemed satisfied just to tease.
I was so excited that I excused myself to masturbate in her bathroom. I was tempted to visit again but never did.
It was with my next encounter with an older woman that I finally had intercourse and it was with her that I knew for sure that older is better. Guiding and teasing, so sure and sexy. Whispering sweet words, mothering and nurturing. Not like those young women who try too hard and go to the gym 5 days a week and have implants. Just a sexy older woman in stockings or girdle, tight panties, or playful lingerie.
Can I ask you . . . Do you like younger men? What is it about them you like? I've never shared any of these experiences with anyone, but I feel so good with you—you're both sexual and sensitive. I would like to know that if my desires are not normal, what do they mean? I still enjoy masturbating to the fantasy of being with an older woman and even bought some panties to help with the ending. As an adult, is this acceptable sexual behavior?
Alone in Canada
Dear Canadian Cutie,
You are normal in every way, sweetheart. Your desire for older women is a preference . . . just as another man might have a preference for large breasts or blonde hair or strippers or librarians. It's difficult not to feel alone when our particular preference isn't popular enough to warrant its own magazine. (Except I think yours is; I doubt that the Over 40, Over 50, and Over 60 magazines are read exclusively by senior citizens.)
Of course, our preferences have a root; they come from someplace inside us. From the description of your early experiences it appears you really love both the sexual confidence and the nurturing an older lover can give. You might be too old for a paper route, but I hope you put yourself into situations where you'll meet older women, sweetheart.
Also, please don't exclude younger women's capacity for both sexual confidence and nurturing sex, honey. Love is difficult enough to find; cast a wide net. Also, explore D&S as a sexual dynamic; you might really enjoy some loving direction and control from a dominant lover (of any age).
Please read, if you haven't, John Irving's novel, A Widow for One Year. The sex and love between the character Marion and her 16-year-old lover is hot, tender, and enduring. The novel captures so well your own experiences and feelings, sweet young Canadian.
Do I like younger men? To be honest, younger men are not my cup of tea. I find younger men attracted to me, though, sometimes desperately so. But I don't care to assume the teacher role in a relationship. However, if I were single, I would never say never . . . and you . . . well, you sound like a perfectly sexy little angel boy. Maybe I'd let you bring me my paper.
Mini-Blind Exhibitionism
Dear Jane,
I'm a 38-year-old male and I like to dress up sexy and drive around or open my mini-blinds and let people look in and see me. I like to tease, usually dressed up in black mini-skirt, fishnet stockings, high heels, and a tight blouse with a 36C stuffed bra.
I am shaved completely. I love smooth, soft skin. I have a lot of clothes for dressing. Is there something wrong with me or not? I've always wished I could find a female who would enjoy it or maybe play dress-up with me.
Oklahoma
Sweet Kinky Okie,
Please, darling, stay out of the window. You see, flaunting yourself through the blinds is not a consensual sexual expression and your neighbors might complain about your behavior to the local police. Driving in your car while dressed is a bit safer in that it affords you some anonymity.
No, sweetheart, there's nothing wrong with you and there's nothing wrong with your wanting (and needing) to satisfy yourself sexually—which you derive not just from cross-dressing, but from exhibitionism as well.
I hear loneliness in your letter and I feel for you. I wish I could conjure up a partner for you. It's scary to get out there and find someone, but I'm a firm believer that there's a lid for every pot. Try meeting women through other activities you like and then, once you get to know and feel safe with a special woman, gently and gradually share your sexual proclivities with her. Until then, sexy doll, please keep your blinds closed.
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 fiancée 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 we 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.