Dr. Tracy's Advice Column

Cartoon Kiss


In Love With a Cross-dresser
Heís a Mommaís Boy
His Email From Another Woman

In Love With a Cross-dresser

Dear Dr. Tracy,

I am a 36 year old widow. I was widowed at 30 and left with 4 kids to raise. After 5 years and two failed relationships, I was blessed with a wonderful man. He's 31 and has no kids. He is 6 ft 3in and 180 lbs, so he's very manly. We have a great relationship. We laugh and talk and reveal all the things we hold deeply inside. I respect everything that's he's divulged to me and would never try to make him feel less than a man for anything he has told and shown to me.

He is a cross-dresser. He likes to wear thigh high pantyhose and a garter, high heels, lingerie, and feather boas. He's even mentioned wanting to wear make-up and a wig. To some degree I find this alluring, well if the truth be told for the most part I enjoy it but, there are times when I feel particularly uncomfortable. He is not gay he says and I believe him because he really LOVES women. I'm so afraid to tell him when I'm feeling uncomfortable because I don't want him to think I don't accept it, because I have. I love him dearly and the depth of our intimacy is amazing, so how can I tell him without hurting him? This man is an industrial roofer so no one would ever guess (much less believe me if I told them) about his fetish yet he's the most gentle and sensitive man I know.

Am I being blind, is he gay but hasn't come to terms with it, or does he just like soft, frilly things? Hey, who am I to judge? I'm a woman and I love to wear jeans, t-shirt, and boots.

Just Wondering in IN.

Dear Wondering,

Having a cross-dressing fetish doesnít mean a man is gay. It just means that heís turned on by wearing womenís clothing. It definitely doesnít mean that he doesnít love women. Perhaps it simply means that he loves women and their clothing more than the average guy. There are social taboos against men wearing womenís clothing. Breaking these taboos is part of the thrill.

Some men were accidentally turned on for the first time by the touch of an auntís silk stocking. They never forgot that original arousal and began to look for more and more chances to be close to the source of their pleasure. The bad news is that your guy may want to cross-dress more and more in the future. The good news is that if you are tolerant and accepting of his behavior, heíll be bound to you in a very special way.

Itís not easy for a man who cross-dresses to find a woman who will allow him to cross-dress without being repulsed or seriously upset. However, if you are slightly uncomfortable from time to time, you should talk to him about your feelings. Donít give him the false impression that itís full-speed ahead and anything goes with you if thatís not the way it is. Itís important that you be able to communicate with him about your feelings in general, and especially on this subject.

Since you have some discomfort with his cross-dressing and since you have young children, you probably want to set some limits on when itís okay for him to be wearing heels and when heíll wear boots. You might also want to make it clear that cross-dressing is okay once in a while, but not every day, night or weekend, depending on your willingness to indulge him.

In a national sex survey I once conducted, I was surprised at how many cross-dressing husbands there are out there. Also, in many cases, the wives participated in the cross-dressing activities by helping to shop for clothes and also to make-up and dress their husbands.

Good luck,

Dr. Tracy

Heís a Mommaís Boy

Dear Dr. Tracy,

My boyfriend and I are both 24 years old and have been dating for almost 4 years. A good portion of that time was spent apart, however, due to us being at different colleges and living in different cities. Recently, I left my job in Maryland in order to move back to Pittsburgh so that we could be together. I had asked my boyfriend to move to Maryland, but he made it clear that he would only live in Pittsburgh so that he could be near his family. I decided to move back in order to "give" to the relationship.

He has always been a "momma's boy", but I truly thought it was a phase that he would "graduate" from when he got his degree and entered the real world. However, now we are living together in Pittsburgh and nothing has changed. He still takes his laundry to his mother's house, and she washes and irons all of his clothes on a weekly basis. She sends over both boxed and prepared food, and even trades him vehicles so that she can get his oil changed for him. His parents also still give him "spending money".

The relationship he has with his family drives me crazy. He and I come from very different upbringings, with me being independent and working hard for everything that I have, and with him having everything handed to him. I feel as if his behavior is preventing us from establishing an adult relationship together. I also feel that everything that I do for him is constantly being overshadowed by what his mother does. No meal that I make can ever be special, because he has had "the best" his whole life.

I have talked to my boyfriend about my feelings, but his actions remain the same. He says that he has to let his mother cook and do his laundry because it is "all that she has to do". She was a housewife who never worked and needs to feel like she is needed.

I wish that his commitment to me was even half of his commitment to his family. Am I with a lost cause here, or is it possible that he will grow out of this dependence stage????

Dear Overshadowed,

You feel overshadowed by his momma because you are. She doesnít want to let go of her little boy and he doesnít want her to let go of him Ė even for you. Heís already told you he doesnít want to live anywhere else but Pittsburgh so he could stay near his family. Doesnít that give you a hint?

He has no plan whatsoever for cutting the umbilical cord. He wants to stay attached. He doesnít want you to come between him and his family, especially his mother. If he has to make a choice, it will probably be mom. So if youíre not the type who can become a part of his family and accept mom, youíd better think about moving on.

Being an independent person yourself, you probably think it's natural that he will grow out of this dependence phase, but that's not necessarily true. At the beginning of mankind, a Cro-Magnon man would go to another tribe and bring a wife back to his cave. The wife was expected to adjust and become a part of his tribe. Sheíd have to live with his mother and adapt to momís ways of doing things. In some parts of the world, this is still the way things are done, and maybe Pittsburghís one.

In any case, you and your guy have very different values. He values family first and being given things, not working for them, and that's not likely to change. This situation is already driving you crazy. If itís bothering you now, itíll bother you more in the future. Mom wonít be around forever, but until sheís gone, heís let you know she comes first. For now, you better figure that theyíre a package deal -- mom comes with whether you like it or not.

Marry him, and you marry mom too.

Good luck,

Dr. Tracy

His Email From Another Woman

Dear Dr. Tracy,

My boyfriend and I have been dating 2 years. I am a widow (49), he is a widower (44). We've known each other for about 8 years...and have both been widowed about the same amount of time, between 8-7 years. We became close friends during that time, as we both shared the same types of challenges and experiences getting through our grief. He had a good marriage, as did I. The pain has been replaced by a deep love and caring for each other. I have no doubt that he loves me and cares for me. And, I take every opportunity to shower him with love, attention and caring. He is a wonderful man, caring, sensitive, attentive and sexy. I'm sure that he would say the same for me.

I am now at a point where I want a more permanent relationship...i.e., marriage. He seems to want the same, however, he still has a daughter at home. And, he has implied that when his last one has flown the nest, he will then have time for "his" life. He has 3 daughters, 21, 19 & 17. I am proud to say that I have a good relationship with all three. They are lovely girls, and I try to nurture them and guide them as I do my own.

I have two children, a son (21), daughter (19). My son lives in another city, is doing very well, and is building a nice life for himself. He will probably be engaged soon. My daughter is friends with his 19 yr. old, (they attend the same college), however, she doesn't feel the same way about his 21 yr. old. I could go on and on here...but, the truth of the matter is that my daughter isn't ecstatic about my relationship with dad. As you can imagine...there are lots of people in this relationship. Sometimes it can be a bit crowded...but, I feel that it is worth the effort and time. And, with work, I can see a future with more happiness than I ever dreamed possible.

So...why am I writing you??? I can handle (with his help) the issues surrounding the merging of two families...BUT, here's my problem...

It appears that my BF has an emotional attachment to a lady he works with. She was a source of support for him in his early grief years, and they worked very closely on a day-to-day basis, although she lives in another state. And...she was married at the time. This past year she announced that she was getting a divorce and wanted to move to our city. He told me he wasn't encouraging her to move, and she hasn't moved...however, the big problem is that he hasn't told her about us, although he talks with her on a daily basis. Today, I was at his house...went to use the computer to print something, and there was an email from her stating that she was listening to some music that reminded her of him. I wanted to discuss the message with him...ask him what it was all about...but, I changed my mind after he arrived home. He had a busy day...and wasn't feeling that great physically. I decided to table the discussion. He saw the message from her...and didn't say a word about it.

Now, I'm wondering if I should bring it up at all. He has known this woman for many years, and, I have also been in a similar situation with an old friend. He has never questioned me or my friendships. Am I just suffering from a case of jealousy? Overreacting? I have a tendency to let my imagination run away...especially when I feel insecure in our relationship. On the surface, I appear confident...pretty, sexy, smart...but, inside I wonder if I'm just his second (or) third choice!

What a dilemma! Please Dr. Tracy...tell me I'm overreacting!

Insecure Widow dating a Widower

Dear Insecure Widow,

First of all, if you canít stop worrying about the ďother woman,Ē maybe you should stop reading his emails. Next best is to keep your mouth shut and your eyes and ears open. That way, you have a chance of finding out if thereís really something going on. Bring it up and heíll become defensive and learn to hide. Also, youíll make yourself seem insecure and jealous, which belittles you.

So donít bring it up. Donít say a word. Donít question him. Instead, work on making every day together wonderful. This will deepen your relationship and cement your position with him. Part of that position is to gradually establish that his friends should become your friends, and vice versa. That way, if the other woman ever does move to your city, she'll be out in the open where you can keep your eye on her.

As for his promise to ďliveĒ when his oldest leaves home, Iíve heard those words before. But in this case, you donít have long to wait to see if he means marrying you when he talks about building a life for himself when the youngest flies away from the nest.

As for your daughterís likes and dislikes, thatís her problem. Try not to let it get in the way of your relationship. Explain to her that itís important to your happiness that everyone get along.

Donít react to insecurity and jealousy and even if your imagination is running wild, keep it under wraps. Donít let him see you sweat the other woman.

Good luck,

Dr. Tracy

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(Featured art from cover of Letting Go, by Zev Wanderer and Tracy Cabot, published by "Bitan" Publishers, Tel-Aviv, Israel)
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