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January 4, 2022, by Marcy Sugar and Kathy Mitchell

Dear Annie: I am a 20-year-old male in a rather unusual situation. I have been intrigued by crossdressing since I was 12 and, as a result, took to “borrowing” a few things from my mother, mainly underwear.

I still live at home, and this interest of mine has caused me much embarrassment. My father has found the borrowed clothing several times and mentioned it once, telling me to stay out of other people’s things. And I know my mother found a pair of her underwear one time.

I don’t know what to do. I feel ashamed and embarrassed taking these things but do not want to stop. I don’t feel as if I am hurting anyone. In fact, I’ve seriously thought about letting Mom catch me in the process of stealing her things so I wouldn’t feel so guilty doing it behind her back.

A couple of years ago, I never thought I could bear talking about crossdressing, but now I think it might be helpful to discuss it with my mother. However, I’m afraid it could go badly and I’ll never again be able to look her in the eyes. This is troubling me to the point where I am losing sleep. Please help. — Confused

Dear Confused: Crossdressing is not like putting on a costume because you’re in a glam rock band. The behavior is more compulsive, but you can curb aspects of it so you are not out of control.

Most crossdressers are heterosexual, often married, and find comfort in crossdressing. There is sometimes a sexual element to it, but not always. It would be helpful if you could discuss this with your mother, and she might be more receptive than you think, since she likely is already aware that you are taking her clothes. Until then, you can find information and support through The Society for the Second Self Inc. (tri-ess.org), P.O. Box 980638, Houston, TX 77098-0638.

Dear Annie: I am 14 years old and have one problem — my mom. Besides this one thing, she’s great, and I love her.

Whenever I have friends over, Mom butts into the conversation or makes jokes that aren’t funny and might even be offensive to my friends. If we are on the computer, she comes and sits and watches what we are doing.

I’ve confronted her about this, and she says that she has every right to talk to my friends and be involved. I don’t mean to exclude her. I just want a little privacy. I’m out of ideas for what to do about this, so I just don’t have friends over anymore. I’m scared if I bring new friends to my house, they will get the wrong impression of me because of Mom. Can you help? — No Friends Because of Mom

Dear No Friends: Don’t assume your friends will think less of you because of your mother. They are smart enough to know you are separate individuals. Parents need to supervise, but they don’t always know how to do it without being intrusive. Walking by the room while you are on the computer is sufficient to check out the sites. Periodically asking your friends if they want a snack is enough conversation. Also, some parents want to be “pals” with their kids and try to be one of the gang. This never works unless Mom is specifically invited to chat. If explaining it to Mom doesn’t help, show her this letter, and tell her you wrote it.

Dear Annie: Every day during my commute, I see car passengers with their feet up in the windows of the vehicles I pass. I would like to warn them that this is not a good idea. During an accident, there is no time to move their feet out of the way when the airbag deploys. They could break their legs. Please tell them. — Waynesboro, Pa.

Dear Waynesboro: You did, and quite succinctly. Thank you.

“Annie’s Mailbox” is written by Kathy Mitchell and Marcy Sugar. This column was originally published in 2017. To find out more about Classic Annie’s Mailbox and read features by other Creators Syndicate writers and cartoonists, visit Creators Syndicate at www.creators.com.

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