September 2005

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.

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.

Audio Fantasies | Videos | Short Video Squirts | Books | Dear Jane | About X-tratalk! | Links | Sylvia's Page | Meet Our Models | What's New? | X-tratalk Forums!
Anal Play | Bondage | Cross-dressing | Foot, Leg & Shoe | Masturbation Lessons | Getting Caught | Panties | Pantyhose | Spanking | Upskirt | Cocktease | Strict Punishment | Role Play

©2008 X-traordinary Talk!
site designed by The Carolingian Empire