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Tell wife about cross-dressing

Dear Annie: My wife and I have been happily married for more than 25 years. We both work, but I run my own business out of our home. Several times a week I like to cross-dress. I’m talking clothes, wig, makeup, the works. I find the feel of women’s clothing enjoyable and stimulating. I am very discreet about it, and my wife doesn’t know.

However, my wife will be retiring soon, which means she will be home all day. I hate to give up something I enjoy so much, but I worry if I tell her, it could mean the end of our marriage. Your thoughts? – Sometime She-Male

Dear Sometime: The urge to cross-dress can be very powerful, and unless you are certain you can stop doing it, your wife will eventually find out. It’s better to discuss it with her rather than risk her coming across your size 12 high heels. Such a surprise will only add a sense of betrayal to her confusion. A lot of women fear cross-dressing means Hubby is gay. This is generally not the case. Your wife needs reassurance of your love and fidelity. Please contact The Society for the Second Self (, P.O. Box 980638, Houston, TX 77098-0638, for information and help.

Dear Annie: I was happy to hear that my cousin and her family were in town for an extended stay, so I invited them over for a cookout and an afternoon swim in our pool. Before this, however, we attended another such get-together and got an eyeful of her pre-teen kids. Boisterous, I can understand. But bullying and disrespectful, I cannot. Worst of all, my cousin’s husband mocked her while she was correcting their children.

I now dread their upcoming visit. How can I correct my cousin’s children without alienating the parents? I do have a spine. I’m just not sure how to use it. Is it appropriate for me to ask the bullying child to leave the pool to “cool off,” if the parents refuse to do it? – Spineful Up North

Dear Spine: Absolutely. You determine the rules on your property. Tell the parents what they are in advance, and if there is inappropriate behavior, give them the opportunity to deal with it. If they refuse to take action, by all means, calmly and authoritatively step in and ask the child to leave the area. If the parents don’t like it, too bad. Having a spine means sometimes facing unpleasantness about your decisions. We feel sorry for kids whose parents are afraid to discipline them or teach proper behavior in public. They will be unwelcome everywhere.

Kathy Mitchell and Marcy Sugar write for Creators Synsdicate. Please e-mail your questions to, or write to: Annie’s Mailbox, P.O. Box 118190, Chicago, IL 60611. To find out more about Annie’s Mailbox, visit


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