Cross-dressing man eager for Halloween opportunity

Published 9:04 am Monday, October 23, 2023

DEAR ABBY: I’m a cross-dresser who is able to enjoy wearing women’s clothes in private at home. With Halloween around the corner, I want nothing more than to be fully dressed as a woman and go outside to experience how it feels. I want to wear a nice dress, high heels, pantyhose, wig, makeup, etc.
My wife knows I enjoy dressing up and tolerates it. But she’s unwilling to let me express myself out of the house or help me with the process. How can I get her to help me get dolled up and experience being a woman for one night? I feel so deprived not being able to be who I want to be. – DRESSED AND READY

DEAR DRESSED: Halloween is the one night of the year when many people, yourself included, can decide to dress up and become who they really are (or would like to be). Because your wife won’t assist you, consider visiting a makeup counter and asking one of the salespeople to help with your makeup that night. And, if nothing in your closet suits the real you, rent or buy an outfit for the occasion. You do not need anyone’s “permission.”
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DEAR ABBY: A very good friend and neighbor sold a Taylor Swift ticket to my 15-year-old daughter for $900. I should mention, my daughter would have given her right arm for the chance to go to the show. The original ticket was purchased for $300, including fees. Initially, my friend wanted to sell it for $1,000, but she offered a “discount” because my daughter’s 16th birthday was coming up.
I can appreciate the value of the hottest ticket in town and that it comes with an inflated price tag. However, from my point of view, it was merely a transaction meant for my friend to make a handsome profit off of my kid. I’m extremely disappointed at the price gouging, and now I think of the woman differently. I have been avoiding her because she will likely become defensive. Am I wrong in thinking her actions were not that of a good friend after all? — FEELING SWINDLED IN THE WEST

DEAR FEELING SWINDLED: Because your neighbor sold the ticket to your daughter at three times what she paid for it, I would have to agree; she acted more like a ticket broker than a good friend. I see no reason why you should cut her off completely, but now you know she’s a shark when it comes to “business,” so keep your eyes open. On the upside, your daughter got to live her dream that night, and many of the fans who saw Taylor Swift in action have said it was the best show of their lives.
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DEAR ABBY: What’s the best way to tell your siblings you think it’s time to stop exchanging Christmas gifts? We’re all in our 60s, and, frankly, I don’t feel they are ever very enthused about what we get them. It just seems like it’s time, anyway. – DONE IN NEW YORK

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DEAR DONE: The best way to convey that message would be verbally, so you can explain that you are all long past childhood and feel a cheery Christmas greeting would suffice. And the best TIME to give them the news would be well before the Christmas holidays.
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Dear Abby is written by Abigail Van Buren, also known as Jeanne Phillips, and was founded by her mother, Pauline Phillips. Contact Dear Abby at www.DearAbby.com or P.O. Box 69440, Los Angeles, CA 90069.
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